u/Beautiful_Demand897

Well, What Were You Expecting? (A sequel to “Wake Up, Babe”) [CD] [breeding] [pegging] [chastity] [plot twists] [slow burn]

Riley and June woke up simultaneously as the sun spilled through the window and onto their bed. It was the first morning in weeks that they had their apartment to themselves, and they soaked in the intimacy of the quiet stillness.

June’s friend Becky had been a perfectly pleasant and gracious houseguest for the two weeks she stayed with them. She was good company, fun to be around, and helpful around the kitchen. She held herself to the “campsite” ethos of leaving every place she stayed better than she found it. And yet, when she left them the night before to catch a flight back to Paris, all three of them—hosts and guest alike—felt the time was right.

Riley and June had passed their “newlywed” stage well before Becky’s arrival, and they had lived together for years before their wedding in any event. They could stand a couple dry weeks for the sake of a good friend. All the same, when their eyes met that morning, they felt the same immediate need to make up for lost time. 

Their bodies snapped together like puzzle pieces. Their arms and legs instantly intertwined and explored each other’s surfaces, and their lips quickly followed. Their mouths watered for each other. Their tongues lapped and swirled inside each other. Their torsos compressed like two bodies aiming to become one.

Riley pulled back first to take in the full beauty of his wife’s face. Her hazel eyes and brunette bob. She stared back into his green eyes and admired his brown, shoulder-length locks. A silent agreement passed between them, to take it slow and soak in every moment. He caressed her body from hips to shoulder and back again over her gray flannel pajamas. She rubbed his chest over his turquoise silk gown.

They’d decided before Becky arrived to let their little experiment continue through her visit. In fact, it was hardly a decision they had to make. Riley knew that June was at least as eager to showcase the results of her work to her closest friend in their PhD program as she was to complete her dissertation based on the same experiment. For his part, Riley didn’t mind at all being her prize possession, her trophy husband, hers to show off with pride.

And so, Becky was aware even before arriving that Riley had undergone hypnotic therapy designed and administered by June. She knew that, as a result, Riley had adopted an almost entirely feminine-presenting wardrobe in place of his (quote-unquote) men’s clothing. 

He was male-presenting whenever he left the apartment and a cis straight man in all other respects. But through June’s hypnotic suggestions, he had lost all apprehensions as a cis straight man over wearing (quote-unquote) women’s clothing. (“They’re not women’s clothes,” he said to Becky. “They’re my clothes.”) The experiment supported her dissertation on the arbitrary nature of gendered clothing and the potential for behavior modification through hypnosis. It also had other side effects that did not make it into her dissertation.

Riley had no hesitation about bringing Becky into the circle. She’d been a close friend of June’s for long enough to feel almost like family. However, June and Riley did agree that Becky (like family) didn’t need to know everything. They could leave out the side effects.

They agreed, for example, that she didn’t need to know that Riley had decided to wear a chastity cage through most of the experiment. And (they agreed) she didn’t need to know how June’s hypnotic suggestions also lowered certain inhibitions on Riley’s part. 

It was enough that she could see just how comfortable Riley was, how effectively June’s hypnotic treatments had subtly but distinctly rewired him. “You know, I was expecting something between Tootsie and To Wong Foo, real performative like,” Becky said to June the first night of her stay, “but he seems just the same. Just Riley in a skirt and blouse, dressing like that because that’s how he dresses.” June hit the table when she said that and yelled, “That’s the idea! Thank you!”

Now, Becky was gone, June had completed her dissertation, and there they were. Husband and wife.

“Just the two of us again,” Riley said, trippingly.

“Yep,” replied June with an extra pop on the “p.” “Well, for now at least…”

“Yeah, for now.” 

Around the time that Riley and June agreed to be exclusive, they had worked out a roadmap for their lives. The steps were laid out with deliberate intentions. Living together allowed them to share expenses and save for their wedding. That was Stage One. The wedding was timed to follow the defense of June’s dissertation while Riley found his stride at the advertising firm. Stage Two. Now, with the wedding behind them and certain professional steps taken, Stage Three was in sight.

“Think we’re ready?” Riley’s tone was whimsical, but the question was serious. “It is pretty nice to have a quiet apartment all to ourselves.”

“Yeah,” June said, meeting Riley where he was, “and a baby isn’t a houseguest. They tend to stick around for more than a couple of weeks.”

“There’s that, on the one hand. And on the other hand…” He finished his thought by putting his hands together near his chest, cradling an imaginary being. June mirrored his motions, and they said in unison: “Baby!”

They shared a moment of anticipation and trepidation until one of them said it, just as they’d been saying it whenever this particular topic came up.

“Just not yet,” said Riley this time.

“Yeah.” June let her inner conflict quiet itself as she returned her hands to the silk fabric covering her husband’s torso. A question had been hovering in the back of her mind, and since she couldn’t hold it back anymore, she decided the time must be right to let it out. “Riley, I was wondering…”

“Yeah?” The gleam in his eye and the little smile on his mouth when he spoke made her melt.

“…now that we’ve—or at least I’ve—gotten what I needed out of this whole, you know…” Riley nodded, following what she was saying. “Do you want me to … un-trigger you?”

“You mean, reverse the treatment? Reset me back to, I don’t want to say ‘normal,” but—"

“Yeah.” 

June didn’t like the word “normal” in this context either, or maybe in any context. It bumped up against her training as a psychologist (and her worldview in general).

Riley raised his eyebrows and turned over onto his back to stare at the ceiling and think. He looked down at the turquoise gown he’d taken to wearing most nights, and then he looked at his wife’s grayscale-toned flannel pajamas. Something he’d noticed over the past few months is that, as his wardrobe and preferences veered deeper into the feminine, June’s style seemed to veer into the masculine. He wondered how conscious that shift was on her part, or if he was imagining it.

“I don’t know if I want to undo anything,” he said, scratching his head in thought.

“Don’t think of it as ‘undoing.’ It’s not like I’d take anything away from you. I was just wondering if any part of your parenthood anxiety had to do with … you know.”

“Oh,” Riley propped himself up by his elbows to weigh the point. It wasn’t the first time he considered it, but it hit differently when she said it out loud. “I guess I have a few thoughts.” June propped herself up with deep interest. “On the one hand, it’s Portland. Our kid—our kids—will see every kind of gender presentation out there. I don’t think they’d see ‘daddy in a dress’ as the least bit weird. On the other hand, setting Becky aside, this has been a pretty private thing between you and me, and that doesn’t have to change even with kids. We can still have private time. And, well … it’s not like I can’t just, you know, dress however I want to dress. Sometimes this way, sometimes that.”

“Yeah, that’s true,” June said, nodding to every point he made.

“What do you think? Would it bother you if I dressed like this around the kids?”

“Oh, I don’t know,” June snapped in a theatrical rebuttal, “I only defended a thesis you could sum up with the line ‘clothes have no inherent gender, it’s all perception and programming.’”

Riley chuckled and smiled. He loved her energy and her attitude, even if he knew that life wasn’t always so simple beyond the borders of a university campus. Even in Portland. And he knew that she knew it, too. After all, he’d never left the house in anything but male-presenting clothes, and she never expected him to.

“I mean, it’s not like I have any other mental blocks, nothing I don’t know about, right? If I want to go back to my old wardrobe, I can just do it!” Riley jumped out of bed with the momentum of purpose, shaking his body to smooth and loosen his gown down to his ankles. “Your whole process ended a while ago. I’m aware of the triggers and their effects. So, I can make conscious choices for myself, right?”

“Sure,” June agreed, not entirely sure where her husband’s train of thought was leading.

Riley entered the closet and pulled out a dusty wardrobe box from the top shelf. He set the box down, opened the lid, and proceeded to remove his turquoise gown and red boyshort underwear.

“If you’re going to strip for me, at least do it to music!” June grabbed her phone from the bedside table to find a suitable song. “Oh, a text from Becky! It says, ‘Check the playlists in your music app.’” June unlocked her phone and opened the app as Becky’s text instructed. 

“Huh.”

“What’s there?” her naked husband asked.

“There’s … hold on … there’s a new playlist on my phone just titled ‘Play Me.’ Okay then.” She hit play, and the first track was an audio recording from Becky.

“Hey guys!” the recording said, “Just wanted to say it was an incredible two weeks, and I can’t thank you enough for putting me up and for putting up with me. Anyways, now you two need to catch up, and I hope this sets the mood right.”

As Becky’s recording played, Riley had pulled out and put on a pair of black and white-striped boxers and a gray men’s undershirt. He looked down and stood in an arms-out pose for June to see.

“Huh,” he said, sounding and feeling nondescript. “Is this normal?”

“I guess, yeah,” June agreed, both in tone and in sentiment.

The playlist continued, and the bedroom filled with the sound of Prince singing, “Here we are folks, the dream we all dream of… boys versus girls in the World Series of Love.”

The timeless groove of “U Got the Look” shifted the vibe of the room in an instant. They both felt a jolt through their body, and they could tell from the look in each other’s eyes that the feeling was mutual.

“Purple.” 

The word fell spontaneously out of June’s mouth. She wasn’t even sure why she said it, other than the obvious association with the Artist Formerly Known As. But the word unleashed something in her mind’s eye, and that something formed a clear picture. “Could you wear the purple set instead today. Just today, and we can decide another time if … you know.”

“Yeah,” Riley agreed, happy to throw off his old clothes, toss them back in the box, and shift over to his dresser. Pulling from the top and the fourth drawers, he retrieved a custom-fitted purple mesh balconette bra and a matching pair of purple mesh panties.

“The whole set,” June burst out, almost involuntarily. “Everything. The purple set.”

“The whole whole set? Everything that we—”

“YES!” June insisted, slapping the sheets with both hands to make herself clear. “EVERYTHING!” 

“Okay, everything that goes with it,” Riley replied with a compliant chuckle. The whole whole set involved pulling open another drawer and returning to their closet for another box, a special box tucked away out of sight on the floor. Riley stood behind the open closet door, just outside of June’s view for the final steps. But she could hear the clips and snaps of the ensemble coming together. When he was done, he turned around to give his wife what she demanded.

He stood upright, back straight and hands on his hips, in the middle of their shag carpet. The bra and panty set fit his curves perfectly. The matching garter held up the black thigh-high stockings that encased his smooth and well-toned legs. And completing the look, something else peaked out from the waistband of the panties and garter belt.

“Fuck, you look amazing,” June said as Sheena Easten agreed over the mobile phone speaker: “Sure enough to be cookin' in my book.”

“Well, what were you expecting?” Riley asked, cocksure and well aware that he had the look.

And right then, in that moment, something snapped inside of June. Her eyes fixed on Riley with a raw intensity that he wasn’t sure he’d ever seen before, not in his recently betrothed wife and not in any previous lover of his. 

The look in her eyes made him quiver. He almost flinched in a fight-or-flight reflex, but before he had the chance, she threw back the covers of their bed and leaped up to grab his face in both of her hands.

Her lips pressed into his with animalistic fury, nearly bumping teeth and pushing him backward. He pushed back with equal force, if only to avoid tumbling to the ground. Her hands reached around to his back and clawed downward from the top of his shoulder, over the band of his bra, to his hips. Her mouth moved around his face, kissing one cheek and then the other before moving to his ear. She sucked and nibbled his right earlobe, holding herself back from biting off a piece of his flesh.

“Take me.” Her words were pure passion but also a plea of sorts. She felt a desperate need in her gut that she couldn’t articulate. She could feel something inside of her, an emptiness that was also somehow a pressure. A bubble that could only be popped from the inside, by a forceful insertion through the nearest point of entry. 

“Now, take me now.”

She sunk her nails into his shoulder blades and pulled him toward her as she moved backward and fell onto their bed. He fell forward with her, breaking his fall with his hands on the mattress. He pulled down his panties to bring his equipment out in full. She frantically pulled at her own flannel pants and her full-cut briefs. He slithered down her body to assist her with the process, removing her bottom clothes and exposing her midsection. 

He was inches from her, and her aroma engulfed him like never before. The scent was different, stronger somehow. He tried to spread her thighs to taste her, but she grabbed him by the ears before his tongue could make contact.

“No, no. Inside me. Right now!” She was already panting, already spitting words out between breaths.

He obliged her, climbing back on top of her and sliding into her without effort. She had gushed to a degree he didn’t know was possible. She was a pool. At the same time, her muscles clenched around him as he entered, making each thrust a satisfying exercise in tension and release. Over and over again.

“Harder, faster!” she yelled. He grabbed her legs and slung one and the other over his two shoulders, bracing his feet to the ground and charging into her with the full force of his quadriceps. “Keep going, don’t stop!” He had no intention of stopping. He could do this all day, for as long as she could take it.

Soon, she used her arms to inch her body away from him and off of him, so that she could flip herself over into a downward-facing position, exposing herself to him with her legs spread wide.

“More, now!” she commanded, and he complied. As soon as his hands touched her hips to grab hold and position himself for reentry, she slammed her backside into him with all her strength. He held his position while she pounded her ass into his pelvis, alternating speeds at times but mostly going as fast as her muscles could stand. Sweat was beading down both of their bodies. Their exertion was also their aphrodisiac, a perfect circle of desire and exhaustion. He wondered briefly if they could do this forever.

At that same moment, June reached out in a desperate grab for the drawer of the nearest bedside table.

“Here,” Riley offered, stretching out his hand to see if he had a better chance of reaching the handle.

“No, no, stay there!”, June commanded. Her fingertips just barely reached the handle, and she yanked open the drawer. Reaching inside, she pulled out a silver bullet, deftly switched it on with one hand, and set the vibration to high. With one hand propping her up to continue her thrusts, her other hand reached between her legs, swirling and pressing the bullet to her clitoris.

The scream she let out was the sound of weeks of sexual desire pent up inside of her. Her orgasm continued until she ran out of breath, and then it continued some more until she collapsed forward, off the fixed piston that was her husband and into a puddle atop their sweat-soaked sheets.

“Fuck,” she muttered between panting breaths, “Fuck, fuck, fuck.”

“Wow.” Riley sat down next to her to stroke her arched back. “Where did that come from?”

The room was suddenly quiet again, except for the sounds of their lungs. The silence was brief. The playlist moved on to “When Doves Cry.” It seemed Becky had programmed a “greatest hits” for them.

“I don’t know,” June gasped, still catching her breath, “I had the sudden overwhelming sensation that I was … um … ovulating.” She said the last word softly, blushing as it stuttered out of her mouth.

“Oh,” Riley replied, taken aback and pondering for a moment. “You can feel that?”

“I don’t know.” June continued gasping. “Some women say they do? I’m not sure if that was it. I only know I needed you to fill me up, like right then and there.”

“Oh, well,” Riley said with a smirk, “I wasn’t going to do that. Fill you up that way, I mean. Not with this.” He held open his hands on either side of his hip, revealing the harness wrapped around his hips and the purple phallus positioned right above the black chastity cage that he wore over his penis.

“You had a strap-on?!?”

Riley’s face scrunched in sheer confusion, and he looked around the room as if he wasn’t sure who she was asking.

“You didn’t know?!?”

“NO!” June was mystified. “YOU WERE STILL CAGED?!?”

“You knew that! It was on all night!”

“I forgot!” June cried in shock, covering her face with her hands. “I… wasn’t thinking!”

 “Obviously!” Riley said with a laugh. “I mean, with your clit maybe!”

June flopped her head backward and let out a shameful groan.

“You said to put on the whole set. Everything that went with it. We bought all of this together, remember?!?” 

June sat back up, sneered at Riley, and threw a pillow at him. It was her tell that she knew he was right, that they were moving on, and that he must never rub it in her face.

“Well, at least we put it to good use!” she said, putting a cap on the morning’s strange sequence of events. He laughed in agreement and bounced onto the mattress next to her. 

“So do you want me to…?”

She didn’t need to complete the question. He shook his head, showing his appreciation for the offer on his face. But he was fully content in that moment to enjoy her enjoyment and absorb some of her afterglow. After a moment, he rolled off to remove the harness and set it on top of the box by the closet.

“I assume I won’t be needing that again,” he said in a self-satisfied tone. “But I think I’ll keep the rest of the set on. For today at least. I can work from home, and a set this nice deserves more than a wham-bam-thank-you-sir.”

June laughed and nodded. “Just be sure to give it the proper outerwear if you’re working from home.”

“Oh, so now it’s a formal dress work-from-home day? Okay, but that means you, too. I’m not going to be my office attire sitting on the couch next to you in last night’s PJs.”

“The green wrap dress is there,” said June, pointing helpfully towards the right side of the closet. 

“You have a preference, I take it?”

“It sets off your eyes nicely.”

“Noted. Any other suggestions?”

“The dress works well with the patent leather pumps.” She sat up in bed, legs crossed, with her chin on her hands, folded in front of her. “The black BOSS heels. They really show off your calves.”

“Duly noted, and I will take that into consideration,” Riley sighed in resignation, reaching towards the right end of the closet, adding, “And you know this calls for accessories.” June nodded with a goofy grin as he pulled open a jewelry box on a closet shelf to grab a necklace and a matching set of bracelets.

Completing the outfit with the aforementioned pumps, he presented himself for his stylist’s approval. She responded with a polite clapping of her hands, to which he gave a dignified bow. The exchange of appreciation was performed to the sounds of “Starfish and Coffee” off the Sign O’ The Times album.

“I’ll get breakfast started.”

“I’ll get dressed!”

As Riley stepped primly heel-to-toe towards the hallway, June leaned forward to follow his path with her eyes.

“You know, I hate to see you go, but I looooooove—”

“Alright, alright!” he yelled at this catcaller on his way to the kitchen. “Just get dressed!”

Breakfast consisted of toasted sourdough bread, scrambled eggs, and freshly squeezed orange juice. The meal was prepared to the sound of “Take Me With U”, sung this time as a duet between the High Priest of Pop and the woman of the house. 

The table was set, and Riley returned to the bedroom to interrupt the performance. There he found a certain sky-blue slim-fit suit of his hanging loosely off the frame of a certain hypnotherapist he knew. Her shoulders were hunched, her knees locked together, her feet spread in a rock-and-roll pose, and her head bent down over a hairbrush standing in for a microphone.

“Honey, take me with you! Woo-hoo-hoo!” 

Riley applauded, and June yelped as she spun around. 

“Jesus, you scared me!”

She had indeed assembled her own office attire for the day, consisting of his two-piece suit and a white button-up shirt loose at the collar. The belt didn’t quite hold the pants in place, and the arms of the suit dangled an inch past her wrists, giving her the overall appearance of a kid rummaging through her dad’s closet.

“Come on, Princess,” he said to her, “breakfast is waiting.”

Before she could take another step, the opening chords of “Purple Rain” burst out of her phone. The dulcet tones locked their bodies in place and their eyes on each other. They couldn’t leave the room if they wanted to, but there was only one direction either of them wanted to go.

By the time Prince sang, “I never meant to cause you any sorrow,” June’s arms were around Riley’s waist, and his arms were over her shoulders. They rocked and swayed around the room, just as they had in the last dance of their wedding night to this very song. Their bodies moved closer and closer with each step and sway to the beat. By the time Prince saw his object of devotion laughing, June’s head was on Riley’s chest.

“This is great,” June cooed. “Remind me to thank Becky for this.”

“Yeah,” Riley agreed. “Seems like this, ah, has you pretty excited.”

“Uh huh…” 

Riley felt a stiffness pressing against his pelvis, something hiding in the pants June had borrowed. Apparently, that wasn’t all she had borrowed from him. June lifted her mouth towards Riley’s ear and whispered, “When you’re looking that hot, what were you expecting?”

Her words set off a firecracker in his brain. Every nerve ending in Riley’s body activated simultaneously, every muscle froze in place, and his eyes dilated. He put his hands on June’s shoulders and nudged her backward a step away from him.

“You okay, babe?” 

For a moment, she worried that he was having a stroke. Then he suddenly fell to his knees in a single, graceful motion and lunged for the buckle of June’s belt. 

“Ooookay.” 

She was growing less concerned that it was a stroke and more intrigued to see where this was going. Meanwhile, Riley fumbled with the belt strap and the fly of his own pants with the manic energy of a teenage boy unclasping a bra on prom night. The bracelets on his wrists made a twinkling sound like a wind chime as they rattled.

“Do you need a hand with—okay, there you go!” 

He succeeded at last and yanked down both the pants and the black and white striped boxers she had pulled from the closet to reveal a familiar purple object that had become a third member of their marriage that morning. 

“Yeah, there it is,” she purred, reflecting the energy she felt vibrating off her husband.

Riley grabbed her attachment at the base and wrapped his lips around the head, bringing his mouth down on it until it hit his palate. To his delight, it tasted of June from their previous intercourse. He sucked as hard as he could to draw out her flavor while shifting his hand and his head to get the shaft as far into his mouth as possible.

“Okay, get it, boy,” June encouraged him, resting one hand on his shoulder and the other on the back of his head.  “Take it all, that’s right.”

His rhythmic motion and muffled groans made her body tingle and her blood shift around inside of her. She almost wondered if she felt a phantom limb between her legs, or if he had simply awakened her imagination into exciting new places. 

Either way, she swore she could feel his lips, the suction of his mouth, the wetness of his tongue as he worshipped her cock.

He went as far as he could with his hand on the shaft, so he moved his hands to grab her hips and pull her toward him and down his throat. When the head of her phallus hit the back of his throat, he gagged and recoiled.

“Oh, are you—” June got as far as saying before he dove back in and overcame his reflex. “Holy shit!” 

When his lips reached the harness, she felt both impressed and genuine pride in his accomplishment.

He pulled back again to catch his breath. Drool spilled out of his mouth at both ends, but he didn’t waste a second wiping it off. He lept to his feet instead, stepped past his wife to the bed, and bent over with his hands on the mattress.

“I need you to take me. Right now. Get the lube.” His voice was urgent, almost panicked.

“Oh! Okay!” June rushed to meet the moment, shuffling as fast as she could to the bedside drawer with her pants around her ankles. Meanwhile, Riley reached one hand down and under his wrap dress, searching for a place to hook his fingers to de-brief himself.

“Let me help you with that, dear,” she said softly as she lifted his dress up to reveal his mesh-covered ass. She pulled down his panties, and, retrieving the bottle from under her arm, she gave a generous pour to both her purple member and the fingers of her left hand. He gingerly stepped out of the panties so that he could spread his legs while she explored his opening with her lubricated fingers. 

One finger, slowly. And then two. And then—

“You’re good, I’m ready, just go!”

She obliged him, holding him still by the hip with one hand and positioning herself to enter him with the other. She started slow, letting his muscles relax and listening as his breaths grew slower and deeper. With each exhale, she pushed herself further into him. She recognized his rhythms. She could read every signal. She knew him, truly inside and out, and she knew just what he could take.

“Now, now, I’m ready,” he insisted. Sooner and faster than she expected. His legs twitched and his torso vibrated. She didn’t know if he really was as ready as he said, but she worried that teasing him any further would send him into seizures.

She knew what it felt like to need that release more than life itself. She was ready to give him what he needed, whatever the fallout.

She hooked her hands into his garter belt like a bridle and began thrusting, pounding into him. He moaned every time her pelvis hit his cheeks. The sound from his mouth was a perfect blend of pleasure and pain, punctuated with gasps of “Yes”, “Yes”, “There”, “Yes!”

At a certain point, right when June worried she might pass out from the aerobics, Riley dramatically arched his back, lifted his backside into the air, and pushed himself even harder onto her. He let out a groan as she hit a particular spot that he’d been seeking deep inside of him. Then, every muscle in his body simultaneously released and relaxed.

June instinctively grabbed onto his hips to hold him in place lest she exit him too quickly. Moving one hand to the tail of his spine to steady him, she pulled back slowly, slowly, and steadily, until she could feel his sphincter close over the tip of her.

Riley crashed forward onto the bed, his seamed-stocking legs bent at the knee and his patent leather pumps sticking straight up into the air, and his arms bent into a little teapot, short and stout. His head turned to one side, revealing a look of utter devastation and complete satisfaction.

Prince cooed and climaxed, and then the playlist came to an end. 

The room was quiet again.

“Let me guess,” June said, pulling her pants back up and positioning herself on the bed for the aftercare, “you—”

“I needed you inside of me like my goddamn life depended on it. And no matter how much you filled me up, it wasn’t enough.”

“Uh huh.”

“I … I think I wanted you to knock me up.”

“Huh. Interesting.” A theory was forming in her head. “So, can I assume you…?” June asked, half-joking but also eager for validation.

“We’ll need to dry clean a few things,” he answered her, panting with every word. “The sheets. The shag carpet. This elegant wrap dress you’re so fond of.”

“Or maybe I keep that one ‘as is” as a trophy,” she said as she slithered beside him and rubbed his back.

“Ooookay, wake up, babes.” Becky’s voice burst out of June’s phone. The playlist had one track left, another recording from their erstwhile guest. “If I timed this right, then your breakfast is probably getting cold right now. Join me in the kitchen.”

June and Riley looked at each other with identical expressions of shock. Eyebrows raised, eyes spiked open, and mouths gaping. “Oh shit!” they said in unison, and together they bounced from their bed into the kitchen.

There, in addition to the breakfast plates cooling on the table, they saw June’s iPad with a Post-It note on it that said in a familiar script, “Check your video files.” Riley turned on the device, looked in the video folder, and saw a file titled “Play Me… After.” 

They sat down at the table, propped the tablet against a fruit bowl, and hit play. There, as if sitting across the table from them, was Becky. From the lack of sunlight coming in through the kitchen window behind her, it must have been recorded before she left the night before.

“Wake up, babes! Now, the next time I say that, I will—” Becky snapped her fingers “—and that will bring it all back to you. You two were the most incredible hosts a person could hope for. There’s no way I could repay you for the last two weeks. So, instead of trying with something silly like money, I left you with a gift. Before I explain, let me just say one more time how grateful I am to be invited into your little circle. Thank you for sharing Riley’s incredible journey and June’s remarkable methods. Riley, you look incredible, and I can only hope to find a man who can pull off your looks and your confidence. June, you are a genius and a visionary. A revolutionary! I very much want you two to have as many babies as possible. Spread those genes! Which brings me to my gift…”

“Oh god,” Riley muttered, reaching for June’s hand as she did the same.

“Oh yeah,” she muttered in return. 

“…if you remember that second night after I arrived … the night that we got, well, preeeeetty—”

“High”, they said in unison.

“—yeah, that. Well, I think you shared a little more with me than you initially planned. That got the stoned-ass wheels in my mind a turnin’, and well, I think I figured out a solution to your baby-making anxieties. You had a mental block. Performance issues, you might say. You were—you are—both ready to take that step, but you’re both nervous. As any two sane adults bringing a new life into this world should be! But for fucks sake, people, the world needs you to breed!”

Riley and June turned to each other, each blushing a matching shade of red.

“So…. we agreed …” Suddenly, Becky’s hand reached out to grab the tablet, and the camera rotated until the recording included June and Riley from last night. “… that you needed a little help turning off your brain and letting your base instincts run wild.”

“Hi, us!” June-and-Riley-from-last-night yelled in unison and waved into the camera, greeting themselves sitting across the table from them in the present. “We are both fully on board, of sound mind and body, yadda yadda yadda.” 

“Hope we had fun!” June added, and the camera rotated again until it was just Becky in the frame.

“We made good use of the two weeks,” Becky continued, “and we hope you’re not sore, except in all the right ways.” An orange suddenly flew into the screen, presumably from June-from-last-night offscreen. “And if everything worked out, then maybe now you can guess at least one of the triggered words I planted…”

The couple turned to each other, each squinting as they thought about it, and each landing on the answer at the same time.

“Expecting!” they yelled in unison, together with Becky on screen.

“So, if everything went as planned, then all I have left to say is…” And together with a snap of her fingers, Becky repeated the words, “Wake up, babes!” The trigger worked. Their memories returned in full, and they turned to each other as if locking eyes for the first time that day. 

“Now, if you’ll excuse me, I’m going to go hypnotize myself into forgetting all the crazy shit you told me about your private time. Just kidding! Keep it weird, you sickos! Goodbye!”

The video ended, the silence returned, and they basked in all of the morning’s revelations. And when the moment passed, they reached the same conclusion, communicated with a gleam in their eyes and a twitch of their lips.

Their breakfast was going to get cold. Their bed was waiting. They were ready to begin.

reddit.com
u/Beautiful_Demand897 — 1 day ago
▲ 7 r/cdstoriesgonewild+1 crossposts

Well, What Were You Expecting? (A sequel to “Wake Up, Babe”) [CD] [breeding] [pegging] [chastity] [plot twists] [slow burn]

Riley and June woke up simultaneously as the sun spilled through the window and onto their bed. It was the first morning in weeks that they had their apartment to themselves, and they soaked in the intimacy of the quiet stillness.

June’s friend Becky had been a perfectly pleasant and gracious houseguest for the two weeks she stayed with them. She was good company, fun to be around, and helpful around the kitchen. She held herself to the “campsite” ethos of leaving every place she stayed better than she found it. And yet, when she left them the night before to catch a flight back to Paris, all three of them—hosts and guest alike—felt the time was right.

Riley and June had passed their “newlywed” stage well before Becky’s arrival, and they had lived together for years before their wedding in any event. They could stand a couple dry weeks for the sake of a good friend. All the same, when their eyes met that morning, they felt the same immediate need to make up for lost time. 

Their bodies snapped together like puzzle pieces. Their arms and legs instantly intertwined and explored each other’s surfaces, and their lips quickly followed. Their mouths watered for each other. Their tongues lapped and swirled inside each other. Their torsos compressed like two bodies aiming to become one.

Riley pulled back first to take in the full beauty of his wife’s face. Her hazel eyes and brunette bob. She stared back into his green eyes and admired his brown, shoulder-length locks. A silent agreement passed between them, to take it slow and soak in every moment. He caressed her body from hips to shoulder and back again over her gray flannel pajamas. She rubbed his chest over his turquoise silk gown.

They’d decided before Becky arrived to let their little experiment continue through her visit. In fact, it was hardly a decision they had to make. Riley knew that June was at least as eager to showcase the results of her work to her closest friend in their PhD program as she was to complete her dissertation based on the same experiment. For his part, Riley didn’t mind at all being her prize possession, her trophy husband, hers to show off with pride.

And so, Becky was aware even before arriving that Riley had undergone hypnotic therapy designed and administered by June. She knew that, as a result, Riley had adopted an almost entirely feminine-presenting wardrobe in place of his (quote-unquote) men’s clothing. 

He was male-presenting whenever he left the apartment and a cis straight man in all other respects. But through June’s hypnotic suggestions, he had lost all apprehensions as a cis straight man over wearing (quote-unquote) women’s clothing. (“They’re not women’s clothes,” he said to Becky. “They’re my clothes.”) The experiment supported her dissertation on the arbitrary nature of gendered clothing and the potential for behavior modification through hypnosis. It also had other side effects that did not make it into her dissertation.

Riley had no hesitation about bringing Becky into the circle. She’d been a close friend of June’s for long enough to feel almost like family. However, June and Riley did agree that Becky (like family) didn’t need to know everything. They could leave out the side effects.

They agreed, for example, that she didn’t need to know that Riley had decided to wear a chastity cage through most of the experiment. And (they agreed) she didn’t need to know how June’s hypnotic suggestions also lowered certain inhibitions on Riley’s part. 

It was enough that she could see just how comfortable Riley was, how effectively June’s hypnotic treatments had subtly but distinctly rewired him. “You know, I was expecting something between Tootsie and To Wong Foo, real performative like,” Becky said to June the first night of her stay, “but he seems just the same. Just Riley in a skirt and blouse, dressing like that because that’s how he dresses.” June hit the table when she said that and yelled, “That’s the idea! Thank you!”

Now, Becky was gone, June had completed her dissertation, and there they were. Husband and wife.

“Just the two of us again,” Riley said, trippingly.

“Yep,” replied June with an extra pop on the “p.” “Well, for now at least…”

“Yeah, for now.” 

Around the time that Riley and June agreed to be exclusive, they had worked out a roadmap for their lives. The steps were laid out with deliberate intentions. Living together allowed them to share expenses and save for their wedding. That was Stage One. The wedding was timed to follow the defense of June’s dissertation while Riley found his stride at the advertising firm. Stage Two. Now, with the wedding behind them and certain professional steps taken, Stage Three was in sight.

“Think we’re ready?” Riley’s tone was whimsical, but the question was serious. “It is pretty nice to have a quiet apartment all to ourselves.”

“Yeah,” June said, meeting Riley where he was, “and a baby isn’t a houseguest. They tend to stick around for more than a couple of weeks.”

“There’s that, on the one hand. And on the other hand…” He finished his thought by putting his hands together near his chest, cradling an imaginary being. June mirrored his motions, and they said in unison: “Baby!”

They shared a moment of anticipation and trepidation until one of them said it, just as they’d been saying it whenever this particular topic came up.

“Just not yet,” said Riley this time.

“Yeah.” June let her inner conflict quiet itself as she returned her hands to the silk fabric covering her husband’s torso. A question had been hovering in the back of her mind, and since she couldn’t hold it back anymore, she decided the time must be right to let it out. “Riley, I was wondering…”

“Yeah?” The gleam in his eye and the little smile on his mouth when he spoke made her melt.

“…now that we’ve—or at least I’ve—gotten what I needed out of this whole, you know…” Riley nodded, following what she was saying. “Do you want me to … un-trigger you?”

“You mean, reverse the treatment? Reset me back to, I don’t want to say ‘normal,” but—"

“Yeah.” 

June didn’t like the word “normal” in this context either, or maybe in any context. It bumped up against her training as a psychologist (and her worldview in general).

Riley raised his eyebrows and turned over onto his back to stare at the ceiling and think. He looked down at the turquoise gown he’d taken to wearing most nights, and then he looked at his wife’s grayscale-toned flannel pajamas. Something he’d noticed over the past few months is that, as his wardrobe and preferences veered deeper into the feminine, June’s style seemed to veer into the masculine. He wondered how conscious that shift was on her part, or if he was imagining it.

“I don’t know if I want to undo anything,” he said, scratching his head in thought.

“Don’t think of it as ‘undoing.’ It’s not like I’d take anything away from you. I was just wondering if any part of your parenthood anxiety had to do with … you know.”

“Oh,” Riley propped himself up by his elbows to weigh the point. It wasn’t the first time he considered it, but it hit differently when she said it out loud. “I guess I have a few thoughts.” June propped herself up with deep interest. “On the one hand, it’s Portland. Our kid—our kids—will see every kind of gender presentation out there. I don’t think they’d see ‘daddy in a dress’ as the least bit weird. On the other hand, setting Becky aside, this has been a pretty private thing between you and me, and that doesn’t have to change even with kids. We can still have private time. And, well … it’s not like I can’t just, you know, dress however I want to dress. Sometimes this way, sometimes that.”

“Yeah, that’s true,” June said, nodding to every point he made.

“What do you think? Would it bother you if I dressed like this around the kids?”

“Oh, I don’t know,” June snapped in a theatrical rebuttal, “I only defended a thesis you could sum up with the line ‘clothes have no inherent gender, it’s all perception and programming.’”

Riley chuckled and smiled. He loved her energy and her attitude, even if he knew that life wasn’t always so simple beyond the borders of a university campus. Even in Portland. And he knew that she knew it, too. After all, he’d never left the house in anything but male-presenting clothes, and she never expected him to.

“I mean, it’s not like I have any other mental blocks, nothing I don’t know about, right? If I want to go back to my old wardrobe, I can just do it!” Riley jumped out of bed with the momentum of purpose, shaking his body to smooth and loosen his gown down to his ankles. “Your whole process ended a while ago. I’m aware of the triggers and their effects. So, I can make conscious choices for myself, right?”

“Sure,” June agreed, not entirely sure where her husband’s train of thought was leading.

Riley entered the closet and pulled out a dusty wardrobe box from the top shelf. He set the box down, opened the lid, and proceeded to remove his turquoise gown and red boyshort underwear.

“If you’re going to strip for me, at least do it to music!” June grabbed her phone from the bedside table to find a suitable song. “Oh, a text from Becky! It says, ‘Check the playlists in your music app.’” June unlocked her phone and opened the app as Becky’s text instructed. 

“Huh.”

“What’s there?” her naked husband asked.

“There’s … hold on … there’s a new playlist on my phone just titled ‘Play Me.’ Okay then.” She hit play, and the first track was an audio recording from Becky.

“Hey guys!” the recording said, “Just wanted to say it was an incredible two weeks, and I can’t thank you enough for putting me up and for putting up with me. Anyways, now you two need to catch up, and I hope this sets the mood right.”

As Becky’s recording played, Riley had pulled out and put on a pair of black and white-striped boxers and a gray men’s undershirt. He looked down and stood in an arms-out pose for June to see.

“Huh,” he said, sounding and feeling nondescript. “Is this normal?”

“I guess, yeah,” June agreed, both in tone and in sentiment.

The playlist continued, and the bedroom filled with the sound of Prince singing, “Here we are folks, the dream we all dream of… boys versus girls in the World Series of Love.”

The timeless groove of “U Got the Look” shifted the vibe of the room in an instant. They both felt a jolt through their body, and they could tell from the look in each other’s eyes that the feeling was mutual.

“Purple.” 

The word fell spontaneously out of June’s mouth. She wasn’t even sure why she said it, other than the obvious association with the Artist Formerly Known As. But the word unleashed something in her mind’s eye, and that something formed a clear picture. “Could you wear the purple set instead today. Just today, and we can decide another time if … you know.”

“Yeah,” Riley agreed, happy to throw off his old clothes, toss them back in the box, and shift over to his dresser. Pulling from the top and the fourth drawers, he retrieved a custom-fitted purple mesh balconette bra and a matching pair of purple mesh panties.

“The whole set,” June burst out, almost involuntarily. “Everything. The purple set.”

“The whole whole set? Everything that we—”

“YES!” June insisted, slapping the sheets with both hands to make herself clear. “EVERYTHING!” 

“Okay, everything that goes with it,” Riley replied with a compliant chuckle. The whole whole set involved pulling open another drawer and returning to their closet for another box, a special box tucked away out of sight on the floor. Riley stood behind the open closet door, just outside of June’s view for the final steps. But she could hear the clips and snaps of the ensemble coming together. When he was done, he turned around to give his wife what she demanded.

He stood upright, back straight and hands on his hips, in the middle of their shag carpet. The bra and panty set fit his curves perfectly. The matching garter held up the black thigh-high stockings that encased his smooth and well-toned legs. And completing the look, something else peaked out from the waistband of the panties and garter belt.

“Fuck, you look amazing,” June said as Sheena Easten agreed over the mobile phone speaker: “Sure enough to be cookin' in my book.”

“Well, what were you expecting?” Riley asked, cocksure and well aware that he had the look.

And right then, in that moment, something snapped inside of June. Her eyes fixed on Riley with a raw intensity that he wasn’t sure he’d ever seen before, not in his recently betrothed wife and not in any previous lover of his. 

The look in her eyes made him quiver. He almost flinched in a fight-or-flight reflex, but before he had the chance, she threw back the covers of their bed and leaped up to grab his face in both of her hands.

Her lips pressed into his with animalistic fury, nearly bumping teeth and pushing him backward. He pushed back with equal force, if only to avoid tumbling to the ground. Her hands reached around to his back and clawed downward from the top of his shoulder, over the band of his bra, to his hips. Her mouth moved around his face, kissing one cheek and then the other before moving to his ear. She sucked and nibbled his right earlobe, holding herself back from biting off a piece of his flesh.

“Take me.” Her words were pure passion but also a plea of sorts. She felt a desperate need in her gut that she couldn’t articulate. She could feel something inside of her, an emptiness that was also somehow a pressure. A bubble that could only be popped from the inside, by a forceful insertion through the nearest point of entry. 

“Now, take me now.”

She sunk her nails into his shoulder blades and pulled him toward her as she moved backward and fell onto their bed. He fell forward with her, breaking his fall with his hands on the mattress. He pulled down his panties to bring his equipment out in full. She frantically pulled at her own flannel pants and her full-cut briefs. He slithered down her body to assist her with the process, removing her bottom clothes and exposing her midsection. 

He was inches from her, and her aroma engulfed him like never before. The scent was different, stronger somehow. He tried to spread her thighs to taste her, but she grabbed him by the ears before his tongue could make contact.

“No, no. Inside me. Right now!” She was already panting, already spitting words out between breaths.

He obliged her, climbing back on top of her and sliding into her without effort. She had gushed to a degree he didn’t know was possible. She was a pool. At the same time, her muscles clenched around him as he entered, making each thrust a satisfying exercise in tension and release. Over and over again.

“Harder, faster!” she yelled. He grabbed her legs and slung one and the other over his two shoulders, bracing his feet to the ground and charging into her with the full force of his quadriceps. “Keep going, don’t stop!” He had no intention of stopping. He could do this all day, for as long as she could take it.

Soon, she used her arms to inch her body away from him and off of him, so that she could flip herself over into a downward-facing position, exposing herself to him with her legs spread wide.

“More, now!” she commanded, and he complied. As soon as his hands touched her hips to grab hold and position himself for reentry, she slammed her backside into him with all her strength. He held his position while she pounded her ass into his pelvis, alternating speeds at times but mostly going as fast as her muscles could stand. Sweat was beading down both of their bodies. Their exertion was also their aphrodisiac, a perfect circle of desire and exhaustion. He wondered briefly if they could do this forever.

At that same moment, June reached out in a desperate grab for the drawer of the nearest bedside table.

“Here,” Riley offered, stretching out his hand to see if he had a better chance of reaching the handle.

“No, no, stay there!”, June commanded. Her fingertips just barely reached the handle, and she yanked open the drawer. Reaching inside, she pulled out a silver bullet, deftly switched it on with one hand, and set the vibration to high. With one hand propping her up to continue her thrusts, her other hand reached between her legs, swirling and pressing the bullet to her clitoris.

The scream she let out was the sound of weeks of sexual desire pent up inside of her. Her orgasm continued until she ran out of breath, and then it continued some more until she collapsed forward, off the fixed piston that was her husband and into a puddle atop their sweat-soaked sheets.

“Fuck,” she muttered between panting breaths, “Fuck, fuck, fuck.”

“Wow.” Riley sat down next to her to stroke her arched back. “Where did that come from?”

The room was suddenly quiet again, except for the sounds of their lungs. The silence was brief. The playlist moved on to “When Doves Cry.” It seemed Becky had programmed a “greatest hits” for them.

“I don’t know,” June gasped, still catching her breath, “I had the sudden overwhelming sensation that I was … um … ovulating.” She said the last word softly, blushing as it stuttered out of her mouth.

“Oh,” Riley replied, taken aback and pondering for a moment. “You can feel that?”

“I don’t know.” June continued gasping. “Some women say they do? I’m not sure if that was it. I only know I needed you to fill me up, like right then and there.”

“Oh, well,” Riley said with a smirk, “I wasn’t going to do that. Fill you up that way, I mean. Not with this.” He held open his hands on either side of his hip, revealing the harness wrapped around his hips and the purple phallus positioned right above the black chastity cage that he wore over his penis.

“You had a strap-on?!?”

Riley’s face scrunched in sheer confusion, and he looked around the room as if he wasn’t sure who she was asking.

“You didn’t know?!?”

“NO!” June was mystified. “YOU WERE STILL CAGED?!?”

“You knew that! It was on all night!”

“I forgot!” June cried in shock, covering her face with her hands. “I… wasn’t thinking!”

 “Obviously!” Riley said with a laugh. “I mean, with your clit maybe!”

June flopped her head backward and let out a shameful groan.

“You said to put on the whole set. Everything that went with it. We bought all of this together, remember?!?” 

June sat back up, sneered at Riley, and threw a pillow at him. It was her tell that she knew he was right, that they were moving on, and that he must never rub it in her face.

“Well, at least we put it to good use!” she said, putting a cap on the morning’s strange sequence of events. He laughed in agreement and bounced onto the mattress next to her. 

“So do you want me to…?”

She didn’t need to complete the question. He shook his head, showing his appreciation for the offer on his face. But he was fully content in that moment to enjoy her enjoyment and absorb some of her afterglow. After a moment, he rolled off to remove the harness and set it on top of the box by the closet.

“I assume I won’t be needing that again,” he said in a self-satisfied tone. “But I think I’ll keep the rest of the set on. For today at least. I can work from home, and a set this nice deserves more than a wham-bam-thank-you-sir.”

June laughed and nodded. “Just be sure to give it the proper outerwear if you’re working from home.”

“Oh, so now it’s a formal dress work-from-home day? Okay, but that means you, too. I’m not going to be my office attire sitting on the couch next to you in last night’s PJs.”

“The green wrap dress is there,” said June, pointing helpfully towards the right side of the closet. 

“You have a preference, I take it?”

“It sets off your eyes nicely.”

“Noted. Any other suggestions?”

“The dress works well with the patent leather pumps.” She sat up in bed, legs crossed, with her chin on her hands, folded in front of her. “The black BOSS heels. They really show off your calves.”

“Duly noted, and I will take that into consideration,” Riley sighed in resignation, reaching towards the right end of the closet, adding, “And you know this calls for accessories.” June nodded with a goofy grin as he pulled open a jewelry box on a closet shelf to grab a necklace and a matching set of bracelets.

Completing the outfit with the aforementioned pumps, he presented himself for his stylist’s approval. She responded with a polite clapping of her hands, to which he gave a dignified bow. The exchange of appreciation was performed to the sounds of “Starfish and Coffee” off the Sign O’ The Times album.

“I’ll get breakfast started.”

“I’ll get dressed!”

As Riley stepped primly heel-to-toe towards the hallway, June leaned forward to follow his path with her eyes.

“You know, I hate to see you go, but I looooooove—”

“Alright, alright!” he yelled at this catcaller on his way to the kitchen. “Just get dressed!”

Breakfast consisted of toasted sourdough bread, scrambled eggs, and freshly squeezed orange juice. The meal was prepared to the sound of “Take Me With U”, sung this time as a duet between the High Priest of Pop and the woman of the house. 

The table was set, and Riley returned to the bedroom to interrupt the performance. There he found a certain sky-blue slim-fit suit of his hanging loosely off the frame of a certain hypnotherapist he knew. Her shoulders were hunched, her knees locked together, her feet spread in a rock-and-roll pose, and her head bent down over a hairbrush standing in for a microphone.

“Honey, take me with you! Woo-hoo-hoo!” 

Riley applauded, and June yelped as she spun around. 

“Jesus, you scared me!”

She had indeed assembled her own office attire for the day, consisting of his two-piece suit and a white button-up shirt loose at the collar. The belt didn’t quite hold the pants in place, and the arms of the suit dangled an inch past her wrists, giving her the overall appearance of a kid rummaging through her dad’s closet.

“Come on, Princess,” he said to her, “breakfast is waiting.”

Before she could take another step, the opening chords of “Purple Rain” burst out of her phone. The dulcet tones locked their bodies in place and their eyes on each other. They couldn’t leave the room if they wanted to, but there was only one direction either of them wanted to go.

By the time Prince sang, “I never meant to cause you any sorrow,” June’s arms were around Riley’s waist, and his arms were over her shoulders. They rocked and swayed around the room, just as they had in the last dance of their wedding night to this very song. Their bodies moved closer and closer with each step and sway to the beat. By the time Prince saw his object of devotion laughing, June’s head was on Riley’s chest.

“This is great,” June cooed. “Remind me to thank Becky for this.”

“Yeah,” Riley agreed. “Seems like this, ah, has you pretty excited.”

“Uh huh…” 

Riley felt a stiffness pressing against his pelvis, something hiding in the pants June had borrowed. Apparently, that wasn’t all she had borrowed from him. June lifted her mouth towards Riley’s ear and whispered, “When you’re looking that hot, what were you expecting?”

Her words set off a firecracker in his brain. Every nerve ending in Riley’s body activated simultaneously, every muscle froze in place, and his eyes dilated. He put his hands on June’s shoulders and nudged her backward a step away from him.

“You okay, babe?” 

For a moment, she worried that he was having a stroke. Then he suddenly fell to his knees in a single, graceful motion and lunged for the buckle of June’s belt. 

“Ooookay.” 

She was growing less concerned that it was a stroke and more intrigued to see where this was going. Meanwhile, Riley fumbled with the belt strap and the fly of his own pants with the manic energy of a teenage boy unclasping a bra on prom night. The bracelets on his wrists made a twinkling sound like a wind chime as they rattled.

“Do you need a hand with—okay, there you go!” 

He succeeded at last and yanked down both the pants and the black and white striped boxers she had pulled from the closet to reveal a familiar purple object that had become a third member of their marriage that morning. 

“Yeah, there it is,” she purred, reflecting the energy she felt vibrating off her husband.

Riley grabbed her attachment at the base and wrapped his lips around the head, bringing his mouth down on it until it hit his palate. To his delight, it tasted of June from their previous intercourse. He sucked as hard as he could to draw out her flavor while shifting his hand and his head to get the shaft as far into his mouth as possible.

“Okay, get it, boy,” June encouraged him, resting one hand on his shoulder and the other on the back of his head.  “Take it all, that’s right.”

His rhythmic motion and muffled groans made her body tingle and her blood shift around inside of her. She almost wondered if she felt a phantom limb between her legs, or if he had simply awakened her imagination into exciting new places. 

Either way, she swore she could feel his lips, the suction of his mouth, the wetness of his tongue as he worshipped her cock.

He went as far as he could with his hand on the shaft, so he moved his hands to grab her hips and pull her toward him and down his throat. When the head of her phallus hit the back of his throat, he gagged and recoiled.

“Oh, are you—” June got as far as saying before he dove back in and overcame his reflex. “Holy shit!” 

When his lips reached the harness, she felt both impressed and genuine pride in his accomplishment.

He pulled back again to catch his breath. Drool spilled out of his mouth at both ends, but he didn’t waste a second wiping it off. He lept to his feet instead, stepped past his wife to the bed, and bent over with his hands on the mattress.

“I need you to take me. Right now. Get the lube.” His voice was urgent, almost panicked.

“Oh! Okay!” June rushed to meet the moment, shuffling as fast as she could to the bedside drawer with her pants around her ankles. Meanwhile, Riley reached one hand down and under his wrap dress, searching for a place to hook his fingers to de-brief himself.

“Let me help you with that, dear,” she said softly as she lifted his dress up to reveal his mesh-covered ass. She pulled down his panties, and, retrieving the bottle from under her arm, she gave a generous pour to both her purple member and the fingers of her left hand. He gingerly stepped out of the panties so that he could spread his legs while she explored his opening with her lubricated fingers. 

One finger, slowly. And then two. And then—

“You’re good, I’m ready, just go!”

She obliged him, holding him still by the hip with one hand and positioning herself to enter him with the other. She started slow, letting his muscles relax and listening as his breaths grew slower and deeper. With each exhale, she pushed herself further into him. She recognized his rhythms. She could read every signal. She knew him, truly inside and out, and she knew just what he could take.

“Now, now, I’m ready,” he insisted. Sooner and faster than she expected. His legs twitched and his torso vibrated. She didn’t know if he really was as ready as he said, but she worried that teasing him any further would send him into seizures.

She knew what it felt like to need that release more than life itself. She was ready to give him what he needed, whatever the fallout.

She hooked her hands into his garter belt like a bridle and began thrusting, pounding into him. He moaned every time her pelvis hit his cheeks. The sound from his mouth was a perfect blend of pleasure and pain, punctuated with gasps of “Yes”, “Yes”, “There”, “Yes!”

At a certain point, right when June worried she might pass out from the aerobics, Riley dramatically arched his back, lifted his backside into the air, and pushed himself even harder onto her. He let out a groan as she hit a particular spot that he’d been seeking deep inside of him. Then, every muscle in his body simultaneously released and relaxed.

June instinctively grabbed onto his hips to hold him in place lest she exit him too quickly. Moving one hand to the tail of his spine to steady him, she pulled back slowly, slowly, and steadily, until she could feel his sphincter close over the tip of her.

Riley crashed forward onto the bed, his seamed-stocking legs bent at the knee and his patent leather pumps sticking straight up into the air, and his arms bent into a little teapot, short and stout. His head turned to one side, revealing a look of utter devastation and complete satisfaction.

Prince cooed and climaxed, and then the playlist came to an end. 

The room was quiet again.

“Let me guess,” June said, pulling her pants back up and positioning herself on the bed for the aftercare, “you—”

“I needed you inside of me like my goddamn life depended on it. And no matter how much you filled me up, it wasn’t enough.”

“Uh huh.”

“I … I think I wanted you to knock me up.”

“Huh. Interesting.” A theory was forming in her head. “So, can I assume you…?” June asked, half-joking but also eager for validation.

“We’ll need to dry clean a few things,” he answered her, panting with every word. “The sheets. The shag carpet. This elegant wrap dress you’re so fond of.”

“Or maybe I keep that one ‘as is” as a trophy,” she said as she slithered beside him and rubbed his back.

“Ooookay, wake up, babes.” Becky’s voice burst out of June’s phone. The playlist had one track left, another recording from their erstwhile guest. “If I timed this right, then your breakfast is probably getting cold right now. Join me in the kitchen.”

June and Riley looked at each other with identical expressions of shock. Eyebrows raised, eyes spiked open, and mouths gaping. “Oh shit!” they said in unison, and together they bounced from their bed into the kitchen.

There, in addition to the breakfast plates cooling on the table, they saw June’s iPad with a Post-It note on it that said in a familiar script, “Check your video files.” Riley turned on the device, looked in the video folder, and saw a file titled “Play Me… After.” 

They sat down at the table, propped the tablet against a fruit bowl, and hit play. There, as if sitting across the table from them, was Becky. From the lack of sunlight coming in through the kitchen window behind her, it must have been recorded before she left the night before.

“Wake up, babes! Now, the next time I say that, I will—” Becky snapped her fingers “—and that will bring it all back to you. You two were the most incredible hosts a person could hope for. There’s no way I could repay you for the last two weeks. So, instead of trying with something silly like money, I left you with a gift. Before I explain, let me just say one more time how grateful I am to be invited into your little circle. Thank you for sharing Riley’s incredible journey and June’s remarkable methods. Riley, you look incredible, and I can only hope to find a man who can pull off your looks and your confidence. June, you are a genius and a visionary. A revolutionary! I very much want you two to have as many babies as possible. Spread those genes! Which brings me to my gift…”

“Oh god,” Riley muttered, reaching for June’s hand as she did the same.

“Oh yeah,” she muttered in return. 

“…if you remember that second night after I arrived … the night that we got, well, preeeeetty—”

“High”, they said in unison.

“—yeah, that. Well, I think you shared a little more with me than you initially planned. That got the stoned-ass wheels in my mind a turnin’, and well, I think I figured out a solution to your baby-making anxieties. You had a mental block. Performance issues, you might say. You were—you are—both ready to take that step, but you’re both nervous. As any two sane adults bringing a new life into this world should be! But for fucks sake, people, the world needs you to breed!”

Riley and June turned to each other, each blushing a matching shade of red.

“So…. we agreed …” Suddenly, Becky’s hand reached out to grab the tablet, and the camera rotated until the recording included June and Riley from last night. “… that you needed a little help turning off your brain and letting your base instincts run wild.”

“Hi, us!” June-and-Riley-from-last-night yelled in unison and waved into the camera, greeting themselves sitting across the table from them in the present. “We are both fully on board, of sound mind and body, yadda yadda yadda.” 

“Hope we had fun!” June added, and the camera rotated again until it was just Becky in the frame.

“We made good use of the two weeks,” Becky continued, “and we hope you’re not sore, except in all the right ways.” An orange suddenly flew into the screen, presumably from June-from-last-night offscreen. “And if everything worked out, then maybe now you can guess at least one of the triggered words I planted…”

The couple turned to each other, each squinting as they thought about it, and each landing on the answer at the same time.

“Expecting!” they yelled in unison, together with Becky on screen.

“So, if everything went as planned, then all I have left to say is…” And together with a snap of her fingers, Becky repeated the words, “Wake up, babes!” The trigger worked. Their memories returned in full, and they turned to each other as if locking eyes for the first time that day. 

“Now, if you’ll excuse me, I’m going to go hypnotize myself into forgetting all the crazy shit you told me about your private time. Just kidding! Keep it weird, you sickos! Goodbye!”

The video ended, the silence returned, and they basked in all of the morning’s revelations. And when the moment passed, they reached the same conclusion, communicated with a gleam in their eyes and a twitch of their lips.

Their breakfast was going to get cold. Their bed was waiting. They were ready to begin.

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u/Beautiful_Demand897 — 1 day ago

Well, What Were You Expecting? (A sequel to “Wake Up, Babe”) [M20sF20s] [CD] [breeding] [pegging] [chastity] [plot twists] [slow burn]

Riley and June woke up simultaneously as the sun spilled through the window and onto their bed. It was the first morning in weeks that they had their apartment to themselves, and they soaked in the intimacy of the quiet stillness.

June’s friend Becky had been a perfectly pleasant and gracious houseguest for the two weeks she stayed with them. She was good company, fun to be around, and helpful around the kitchen. She held herself to the “campsite” ethos of leaving every place she stayed better than she found it. And yet, when she left them the night before to catch a flight back to Paris, all three of them—hosts and guest alike—felt the time was right.

Riley and June had passed their “newlywed” stage well before Becky’s arrival, and they had lived together for years before their wedding in any event. They could stand a couple dry weeks for the sake of a good friend. All the same, when their eyes met that morning, they felt the same immediate need to make up for lost time. 

Their bodies snapped together like puzzle pieces. Their arms and legs instantly intertwined and explored each other’s surfaces, and their lips quickly followed. Their mouths watered for each other. Their tongues lapped and swirled inside each other. Their torsos compressed like two bodies aiming to become one.

Riley pulled back first to take in the full beauty of his wife’s face. Her hazel eyes and brunette bob. She stared back into his green eyes and admired his brown, shoulder-length locks. A silent agreement passed between them, to take it slow and soak in every moment. He caressed her body from hips to shoulder and back again over her gray flannel pajamas. She rubbed his chest over his turquoise silk gown.

They’d decided before Becky arrived to let their little experiment continue through her visit. In fact, it was hardly a decision they had to make. Riley knew that June was at least as eager to showcase the results of her work to her closest friend in their PhD program as she was to complete her dissertation based on the same experiment. For his part, Riley didn’t mind at all being her prize possession, her trophy husband, hers to show off with pride.

And so, Becky was aware even before arriving that Riley had undergone hypnotic therapy designed and administered by June. She knew that, as a result, Riley had adopted an almost entirely feminine-presenting wardrobe in place of his (quote-unquote) men’s clothing. 

He was male-presenting whenever he left the apartment and a cis straight man in all other respects. But through June’s hypnotic suggestions, he had lost all apprehensions as a cis straight man over wearing (quote-unquote) women’s clothing. (“They’re not women’s clothes,” he said to Becky. “They’re my clothes.”) The experiment supported her dissertation on the arbitrary nature of gendered clothing and the potential for behavior modification through hypnosis. It also had other side effects that did not make it into her dissertation.

Riley had no hesitation about bringing Becky into the circle. She’d been a close friend of June’s for long enough to feel almost like family. However, June and Riley did agree that Becky (like family) didn’t need to know everything. They could leave out the side effects.

They agreed, for example, that she didn’t need to know that Riley had decided to wear a chastity cage through most of the experiment. And (they agreed) she didn’t need to know how June’s hypnotic suggestions also lowered certain inhibitions on Riley’s part. 

It was enough that she could see just how comfortable Riley was, how effectively June’s hypnotic treatments had subtly but distinctly rewired him. “You know, I was expecting something between Tootsie and To Wong Foo, real performative like,” Becky said to June the first night of her stay, “but he seems just the same. Just Riley in a skirt and blouse, dressing like that because that’s how he dresses.” June hit the table when she said that and yelled, “That’s the idea! Thank you!”

Now, Becky was gone, June had completed her dissertation, and there they were. Husband and wife.

“Just the two of us again,” Riley said, trippingly.

“Yep,” replied June with an extra pop on the “p.” “Well, for now at least…”

“Yeah, for now.” 

Around the time that Riley and June agreed to be exclusive, they had worked out a roadmap for their lives. The steps were laid out with deliberate intentions. Living together allowed them to share expenses and save for their wedding. That was Stage One. The wedding was timed to follow the defense of June’s dissertation while Riley found his stride at the advertising firm. Stage Two. Now, with the wedding behind them and certain professional steps taken, Stage Three was in sight.

“Think we’re ready?” Riley’s tone was whimsical, but the question was serious. “It is pretty nice to have a quiet apartment all to ourselves.”

“Yeah,” June said, meeting Riley where he was, “and a baby isn’t a houseguest. They tend to stick around for more than a couple of weeks.”

“There’s that, on the one hand. And on the other hand…” He finished his thought by putting his hands together near his chest, cradling an imaginary being. June mirrored his motions, and they said in unison: “Baby!”

They shared a moment of anticipation and trepidation until one of them said it, just as they’d been saying it whenever this particular topic came up.

“Just not yet,” said Riley this time.

“Yeah.” June let her inner conflict quiet itself as she returned her hands to the silk fabric covering her husband’s torso. A question had been hovering in the back of her mind, and since she couldn’t hold it back anymore, she decided the time must be right to let it out. “Riley, I was wondering…”

“Yeah?” The gleam in his eye and the little smile on his mouth when he spoke made her melt.

“…now that we’ve—or at least I’ve—gotten what I needed out of this whole, you know…” Riley nodded, following what she was saying. “Do you want me to … un-trigger you?”

“You mean, reverse the treatment? Reset me back to, I don’t want to say ‘normal,” but—"

“Yeah.” 

June didn’t like the word “normal” in this context either, or maybe in any context. It bumped up against her training as a psychologist (and her worldview in general).

Riley raised his eyebrows and turned over onto his back to stare at the ceiling and think. He looked down at the turquoise gown he’d taken to wearing most nights, and then he looked at his wife’s grayscale-toned flannel pajamas. Something he’d noticed over the past few months is that, as his wardrobe and preferences veered deeper into the feminine, June’s style seemed to veer into the masculine. He wondered how conscious that shift was on her part, or if he was imagining it.

“I don’t know if I want to undo anything,” he said, scratching his head in thought.

“Don’t think of it as ‘undoing.’ It’s not like I’d take anything away from you. I was just wondering if any part of your parenthood anxiety had to do with … you know.”

“Oh,” Riley propped himself up by his elbows to weigh the point. It wasn’t the first time he considered it, but it hit differently when she said it out loud. “I guess I have a few thoughts.” June propped herself up with deep interest. “On the one hand, it’s Portland. Our kid—our kids—will see every kind of gender presentation out there. I don’t think they’d see ‘daddy in a dress’ as the least bit weird. On the other hand, setting Becky aside, this has been a pretty private thing between you and me, and that doesn’t have to change even with kids. We can still have private time. And, well … it’s not like I can’t just, you know, dress however I want to dress. Sometimes this way, sometimes that.”

“Yeah, that’s true,” June said, nodding to every point he made.

“What do you think? Would it bother you if I dressed like this around the kids?”

“Oh, I don’t know,” June snapped in a theatrical rebuttal, “I only defended a thesis you could sum up with the line ‘clothes have no inherent gender, it’s all perception and programming.’”

Riley chuckled and smiled. He loved her energy and her attitude, even if he knew that life wasn’t always so simple beyond the borders of a university campus. Even in Portland. And he knew that she knew it, too. After all, he’d never left the house in anything but male-presenting clothes, and she never expected him to.

“I mean, it’s not like I have any other mental blocks, nothing I don’t know about, right? If I want to go back to my old wardrobe, I can just do it!” Riley jumped out of bed with the momentum of purpose, shaking his body to smooth and loosen his gown down to his ankles. “Your whole process ended a while ago. I’m aware of the triggers and their effects. So, I can make conscious choices for myself, right?”

“Sure,” June agreed, not entirely sure where her husband’s train of thought was leading.

Riley entered the closet and pulled out a dusty wardrobe box from the top shelf. He set the box down, opened the lid, and proceeded to remove his turquoise gown and red boyshort underwear.

“If you’re going to strip for me, at least do it to music!” June grabbed her phone from the bedside table to find a suitable song. “Oh, a text from Becky! It says, ‘Check the playlists in your music app.’” June unlocked her phone and opened the app as Becky’s text instructed. 

“Huh.”

“What’s there?” her naked husband asked.

“There’s … hold on … there’s a new playlist on my phone just titled ‘Play Me.’ Okay then.” She hit play, and the first track was an audio recording from Becky.

“Hey guys!” the recording said, “Just wanted to say it was an incredible two weeks, and I can’t thank you enough for putting me up and for putting up with me. Anyways, now you two need to catch up, and I hope this sets the mood right.”

As Becky’s recording played, Riley had pulled out and put on a pair of black and white-striped boxers and a gray men’s undershirt. He looked down and stood in an arms-out pose for June to see.

“Huh,” he said, sounding and feeling nondescript. “Is this normal?”

“I guess, yeah,” June agreed, both in tone and in sentiment.

The playlist continued, and the bedroom filled with the sound of Prince singing, “Here we are folks, the dream we all dream of… boys versus girls in the World Series of Love.”

The timeless groove of “U Got the Look” shifted the vibe of the room in an instant. They both felt a jolt through their body, and they could tell from the look in each other’s eyes that the feeling was mutual.

“Purple.” 

The word fell spontaneously out of June’s mouth. She wasn’t even sure why she said it, other than the obvious association with the Artist Formerly Known As. But the word unleashed something in her mind’s eye, and that something formed a clear picture. “Could you wear the purple set instead today. Just today, and we can decide another time if … you know.”

“Yeah,” Riley agreed, happy to throw off his old clothes, toss them back in the box, and shift over to his dresser. Pulling from the top and the fourth drawers, he retrieved a custom-fitted purple mesh balconette bra and a matching pair of purple mesh panties.

“The whole set,” June burst out, almost involuntarily. “Everything. The purple set.”

“The whole whole set? Everything that we—”

“YES!” June insisted, slapping the sheets with both hands to make herself clear. “EVERYTHING!” 

“Okay, everything that goes with it,” Riley replied with a compliant chuckle. The whole whole set involved pulling open another drawer and returning to their closet for another box, a special box tucked away out of sight on the floor. Riley stood behind the open closet door, just outside of June’s view for the final steps. But she could hear the clips and snaps of the ensemble coming together. When he was done, he turned around to give his wife what she demanded.

He stood upright, back straight and hands on his hips, in the middle of their shag carpet. The bra and panty set fit his curves perfectly. The matching garter held up the black thigh-high stockings that encased his smooth and well-toned legs. And completing the look, something else peaked out from the waistband of the panties and garter belt.

“Fuck, you look amazing,” June said as Sheena Easten agreed over the mobile phone speaker: “Sure enough to be cookin' in my book.”

“Well, what were you expecting?” Riley asked, cocksure and well aware that he had the look.

And right then, in that moment, something snapped inside of June. Her eyes fixed on Riley with a raw intensity that he wasn’t sure he’d ever seen before, not in his recently betrothed wife and not in any previous lover of his. 

The look in her eyes made him quiver. He almost flinched in a fight-or-flight reflex, but before he had the chance, she threw back the covers of their bed and leaped up to grab his face in both of her hands.

Her lips pressed into his with animalistic fury, nearly bumping teeth and pushing him backward. He pushed back with equal force, if only to avoid tumbling to the ground. Her hands reached around to his back and clawed downward from the top of his shoulder, over the band of his bra, to his hips. Her mouth moved around his face, kissing one cheek and then the other before moving to his ear. She sucked and nibbled his right earlobe, holding herself back from biting off a piece of his flesh.

“Take me.” Her words were pure passion but also a plea of sorts. She felt a desperate need in her gut that she couldn’t articulate. She could feel something inside of her, an emptiness that was also somehow a pressure. A bubble that could only be popped from the inside, by a forceful insertion through the nearest point of entry. 

“Now, take me now.”

She sunk her nails into his shoulder blades and pulled him toward her as she moved backward and fell onto their bed. He fell forward with her, breaking his fall with his hands on the mattress. He pulled down his panties to bring his equipment out in full. She frantically pulled at her own flannel pants and her full-cut briefs. He slithered down her body to assist her with the process, removing her bottom clothes and exposing her midsection. 

He was inches from her, and her aroma engulfed him like never before. The scent was different, stronger somehow. He tried to spread her thighs to taste her, but she grabbed him by the ears before his tongue could make contact.

“No, no. Inside me. Right now!” She was already panting, already spitting words out between breaths.

He obliged her, climbing back on top of her and sliding into her without effort. She had gushed to a degree he didn’t know was possible. She was a pool. At the same time, her muscles clenched around him as he entered, making each thrust a satisfying exercise in tension and release. Over and over again.

“Harder, faster!” she yelled. He grabbed her legs and slung one and the other over his two shoulders, bracing his feet to the ground and charging into her with the full force of his quadriceps. “Keep going, don’t stop!” He had no intention of stopping. He could do this all day, for as long as she could take it.

Soon, she used her arms to inch her body away from him and off of him, so that she could flip herself over into a downward-facing position, exposing herself to him with her legs spread wide.

“More, now!” she commanded, and he complied. As soon as his hands touched her hips to grab hold and position himself for reentry, she slammed her backside into him with all her strength. He held his position while she pounded her ass into his pelvis, alternating speeds at times but mostly going as fast as her muscles could stand. Sweat was beading down both of their bodies. Their exertion was also their aphrodisiac, a perfect circle of desire and exhaustion. He wondered briefly if they could do this forever.

At that same moment, June reached out in a desperate grab for the drawer of the nearest bedside table.

“Here,” Riley offered, stretching out his hand to see if he had a better chance of reaching the handle.

“No, no, stay there!”, June commanded. Her fingertips just barely reached the handle, and she yanked open the drawer. Reaching inside, she pulled out a silver bullet, deftly switched it on with one hand, and set the vibration to high. With one hand propping her up to continue her thrusts, her other hand reached between her legs, swirling and pressing the bullet to her clitoris.

The scream she let out was the sound of weeks of sexual desire pent up inside of her. Her orgasm continued until she ran out of breath, and then it continued some more until she collapsed forward, off the fixed piston that was her husband and into a puddle atop their sweat-soaked sheets.

“Fuck,” she muttered between panting breaths, “Fuck, fuck, fuck.”

“Wow.” Riley sat down next to her to stroke her arched back. “Where did that come from?”

The room was suddenly quiet again, except for the sounds of their lungs. The silence was brief. The playlist moved on to “When Doves Cry.” It seemed Becky had programmed a “greatest hits” for them.

“I don’t know,” June gasped, still catching her breath, “I had the sudden overwhelming sensation that I was … um … ovulating.” She said the last word softly, blushing as it stuttered out of her mouth.

“Oh,” Riley replied, taken aback and pondering for a moment. “You can feel that?”

“I don’t know.” June continued gasping. “Some women say they do? I’m not sure if that was it. I only know I needed you to fill me up, like right then and there.”

“Oh, well,” Riley said with a smirk, “I wasn’t going to do that. Fill you up that way, I mean. Not with this.” He held open his hands on either side of his hip, revealing the harness wrapped around his hips and the purple phallus positioned right above the black chastity cage that he wore over his penis.

“You had a strap-on?!?”

Riley’s face scrunched in sheer confusion, and he looked around the room as if he wasn’t sure who she was asking.

“You didn’t know?!?”

“NO!” June was mystified. “YOU WERE STILL CAGED?!?”

“You knew that! It was on all night!”

“I forgot!” June cried in shock, covering her face with her hands. “I… wasn’t thinking!”

 “Obviously!” Riley said with a laugh. “I mean, with your clit maybe!”

June flopped her head backward and let out a shameful groan.

“You said to put on the whole set. Everything that went with it. We bought all of this together, remember?!?” 

June sat back up, sneered at Riley, and threw a pillow at him. It was her tell that she knew he was right, that they were moving on, and that he must never rub it in her face.

“Well, at least we put it to good use!” she said, putting a cap on the morning’s strange sequence of events. He laughed in agreement and bounced onto the mattress next to her. 

“So do you want me to…?”

She didn’t need to complete the question. He shook his head, showing his appreciation for the offer on his face. But he was fully content in that moment to enjoy her enjoyment and absorb some of her afterglow. After a moment, he rolled off to remove the harness and set it on top of the box by the closet.

“I assume I won’t be needing that again,” he said in a self-satisfied tone. “But I think I’ll keep the rest of the set on. For today at least. I can work from home, and a set this nice deserves more than a wham-bam-thank-you-sir.”

June laughed and nodded. “Just be sure to give it the proper outerwear if you’re working from home.”

“Oh, so now it’s a formal dress work-from-home day? Okay, but that means you, too. I’m not going to be my office attire sitting on the couch next to you in last night’s PJs.”

“The green wrap dress is there,” said June, pointing helpfully towards the right side of the closet. 

“You have a preference, I take it?”

“It sets off your eyes nicely.”

“Noted. Any other suggestions?”

“The dress works well with the patent leather pumps.” She sat up in bed, legs crossed, with her chin on her hands, folded in front of her. “The black BOSS heels. They really show off your calves.”

“Duly noted, and I will take that into consideration,” Riley sighed in resignation, reaching towards the right end of the closet, adding, “And you know this calls for accessories.” June nodded with a goofy grin as he pulled open a jewelry box on a closet shelf to grab a necklace and a matching set of bracelets.

Completing the outfit with the aforementioned pumps, he presented himself for his stylist’s approval. She responded with a polite clapping of her hands, to which he gave a dignified bow. The exchange of appreciation was performed to the sounds of “Starfish and Coffee” off the Sign O’ The Times album.

“I’ll get breakfast started.”

“I’ll get dressed!”

As Riley stepped primly heel-to-toe towards the hallway, June leaned forward to follow his path with her eyes.

“You know, I hate to see you go, but I looooooove—”

“Alright, alright!” he yelled at this catcaller on his way to the kitchen. “Just get dressed!”

Breakfast consisted of toasted sourdough bread, scrambled eggs, and freshly squeezed orange juice. The meal was prepared to the sound of “Take Me With U”, sung this time as a duet between the High Priest of Pop and the woman of the house. 

The table was set, and Riley returned to the bedroom to interrupt the performance. There he found a certain sky-blue slim-fit suit of his hanging loosely off the frame of a certain hypnotherapist he knew. Her shoulders were hunched, her knees locked together, her feet spread in a rock-and-roll pose, and her head bent down over a hairbrush standing in for a microphone.

“Honey, take me with you! Woo-hoo-hoo!” 

Riley applauded, and June yelped as she spun around. 

“Jesus, you scared me!”

She had indeed assembled her own office attire for the day, consisting of his two-piece suit and a white button-up shirt loose at the collar. The belt didn’t quite hold the pants in place, and the arms of the suit dangled an inch past her wrists, giving her the overall appearance of a kid rummaging through her dad’s closet.

“Come on, Princess,” he said to her, “breakfast is waiting.”

Before she could take another step, the opening chords of “Purple Rain” burst out of her phone. The dulcet tones locked their bodies in place and their eyes on each other. They couldn’t leave the room if they wanted to, but there was only one direction either of them wanted to go.

By the time Prince sang, “I never meant to cause you any sorrow,” June’s arms were around Riley’s waist, and his arms were over her shoulders. They rocked and swayed around the room, just as they had in the last dance of their wedding night to this very song. Their bodies moved closer and closer with each step and sway to the beat. By the time Prince saw his object of devotion laughing, June’s head was on Riley’s chest.

“This is great,” June cooed. “Remind me to thank Becky for this.”

“Yeah,” Riley agreed. “Seems like this, ah, has you pretty excited.”

“Uh huh…” 

Riley felt a stiffness pressing against his pelvis, something hiding in the pants June had borrowed. Apparently, that wasn’t all she had borrowed from him. June lifted her mouth towards Riley’s ear and whispered, “When you’re looking that hot, what were you expecting?”

Her words set off a firecracker in his brain. Every nerve ending in Riley’s body activated simultaneously, every muscle froze in place, and his eyes dilated. He put his hands on June’s shoulders and nudged her backward a step away from him.

“You okay, babe?” 

For a moment, she worried that he was having a stroke. Then he suddenly fell to his knees in a single, graceful motion and lunged for the buckle of June’s belt. 

“Ooookay.” 

She was growing less concerned that it was a stroke and more intrigued to see where this was going. Meanwhile, Riley fumbled with the belt strap and the fly of his own pants with the manic energy of a teenage boy unclasping a bra on prom night. The bracelets on his wrists made a twinkling sound like a wind chime as they rattled.

“Do you need a hand with—okay, there you go!” 

He succeeded at last and yanked down both the pants and the black and white striped boxers she had pulled from the closet to reveal a familiar purple object that had become a third member of their marriage that morning. 

“Yeah, there it is,” she purred, reflecting the energy she felt vibrating off her husband.

Riley grabbed her attachment at the base and wrapped his lips around the head, bringing his mouth down on it until it hit his palate. To his delight, it tasted of June from their previous intercourse. He sucked as hard as he could to draw out her flavor while shifting his hand and his head to get the shaft as far into his mouth as possible.

“Okay, get it, boy,” June encouraged him, resting one hand on his shoulder and the other on the back of his head.  “Take it all, that’s right.”

His rhythmic motion and muffled groans made her body tingle and her blood shift around inside of her. She almost wondered if she felt a phantom limb between her legs, or if he had simply awakened her imagination into exciting new places. 

Either way, she swore she could feel his lips, the suction of his mouth, the wetness of his tongue as he worshipped her cock.

He went as far as he could with his hand on the shaft, so he moved his hands to grab her hips and pull her toward him and down his throat. When the head of her phallus hit the back of his throat, he gagged and recoiled.

“Oh, are you—” June got as far as saying before he dove back in and overcame his reflex. “Holy shit!” 

When his lips reached the harness, she felt both impressed and genuine pride in his accomplishment.

He pulled back again to catch his breath. Drool spilled out of his mouth at both ends, but he didn’t waste a second wiping it off. He lept to his feet instead, stepped past his wife to the bed, and bent over with his hands on the mattress.

“I need you to take me. Right now. Get the lube.” His voice was urgent, almost panicked.

“Oh! Okay!” June rushed to meet the moment, shuffling as fast as she could to the bedside drawer with her pants around her ankles. Meanwhile, Riley reached one hand down and under his wrap dress, searching for a place to hook his fingers to de-brief himself.

“Let me help you with that, dear,” she said softly as she lifted his dress up to reveal his mesh-covered ass. She pulled down his panties, and, retrieving the bottle from under her arm, she gave a generous pour to both her purple member and the fingers of her left hand. He gingerly stepped out of the panties so that he could spread his legs while she explored his opening with her lubricated fingers. 

One finger, slowly. And then two. And then—

“You’re good, I’m ready, just go!”

She obliged him, holding him still by the hip with one hand and positioning herself to enter him with the other. She started slow, letting his muscles relax and listening as his breaths grew slower and deeper. With each exhale, she pushed herself further into him. She recognized his rhythms. She could read every signal. She knew him, truly inside and out, and she knew just what he could take.

“Now, now, I’m ready,” he insisted. Sooner and faster than she expected. His legs twitched and his torso vibrated. She didn’t know if he really was as ready as he said, but she worried that teasing him any further would send him into seizures.

She knew what it felt like to need that release more than life itself. She was ready to give him what he needed, whatever the fallout.

She hooked her hands into his garter belt like a bridle and began thrusting, pounding into him. He moaned every time her pelvis hit his cheeks. The sound from his mouth was a perfect blend of pleasure and pain, punctuated with gasps of “Yes”, “Yes”, “There”, “Yes!”

At a certain point, right when June worried she might pass out from the aerobics, Riley dramatically arched his back, lifted his backside into the air, and pushed himself even harder onto her. He let out a groan as she hit a particular spot that he’d been seeking deep inside of him. Then, every muscle in his body simultaneously released and relaxed.

June instinctively grabbed onto his hips to hold him in place lest she exit him too quickly. Moving one hand to the tail of his spine to steady him, she pulled back slowly, slowly, and steadily, until she could feel his sphincter close over the tip of her.

Riley crashed forward onto the bed, his seamed-stocking legs bent at the knee and his patent leather pumps sticking straight up into the air, and his arms bent into a little teapot, short and stout. His head turned to one side, revealing a look of utter devastation and complete satisfaction.

Prince cooed and climaxed, and then the playlist came to an end. 

The room was quiet again.

“Let me guess,” June said, pulling her pants back up and positioning herself on the bed for the aftercare, “you—”

“I needed you inside of me like my goddamn life depended on it. And no matter how much you filled me up, it wasn’t enough.”

“Uh huh.”

“I … I think I wanted you to knock me up.”

“Huh. Interesting.” A theory was forming in her head. “So, can I assume you…?” June asked, half-joking but also eager for validation.

“We’ll need to dry clean a few things,” he answered her, panting with every word. “The sheets. The shag carpet. This elegant wrap dress you’re so fond of.”

“Or maybe I keep that one ‘as is” as a trophy,” she said as she slithered beside him and rubbed his back.

“Ooookay, wake up, babes.” Becky’s voice burst out of June’s phone. The playlist had one track left, another recording from their erstwhile guest. “If I timed this right, then your breakfast is probably getting cold right now. Join me in the kitchen.”

June and Riley looked at each other with identical expressions of shock. Eyebrows raised, eyes spiked open, and mouths gaping. “Oh shit!” they said in unison, and together they bounced from their bed into the kitchen.

There, in addition to the breakfast plates cooling on the table, they saw June’s iPad with a Post-It note on it that said in a familiar script, “Check your video files.” Riley turned on the device, looked in the video folder, and saw a file titled “Play Me… After.” 

They sat down at the table, propped the tablet against a fruit bowl, and hit play. There, as if sitting across the table from them, was Becky. From the lack of sunlight coming in through the kitchen window behind her, it must have been recorded before she left the night before.

“Wake up, babes! Now, the next time I say that, I will—” Becky snapped her fingers “—and that will bring it all back to you. You two were the most incredible hosts a person could hope for. There’s no way I could repay you for the last two weeks. So, instead of trying with something silly like money, I left you with a gift. Before I explain, let me just say one more time how grateful I am to be invited into your little circle. Thank you for sharing Riley’s incredible journey and June’s remarkable methods. Riley, you look incredible, and I can only hope to find a man who can pull off your looks and your confidence. June, you are a genius and a visionary. A revolutionary! I very much want you two to have as many babies as possible. Spread those genes! Which brings me to my gift…”

“Oh god,” Riley muttered, reaching for June’s hand as she did the same.

“Oh yeah,” she muttered in return. 

“…if you remember that second night after I arrived … the night that we got, well, preeeeetty—”

“High”, they said in unison.

“—yeah, that. Well, I think you shared a little more with me than you initially planned. That got the stoned-ass wheels in my mind a turnin’, and well, I think I figured out a solution to your baby-making anxieties. You had a mental block. Performance issues, you might say. You were—you are—both ready to take that step, but you’re both nervous. As any two sane adults bringing a new life into this world should be! But for fucks sake, people, the world needs you to breed!”

Riley and June turned to each other, each blushing a matching shade of red.

“So…. we agreed …” Suddenly, Becky’s hand reached out to grab the tablet, and the camera rotated until the recording included June and Riley from last night. “… that you needed a little help turning off your brain and letting your base instincts run wild.”

“Hi, us!” June-and-Riley-from-last-night yelled in unison and waved into the camera, greeting themselves sitting across the table from them in the present. “We are both fully on board, of sound mind and body, yadda yadda yadda.” 

“Hope we had fun!” June added, and the camera rotated again until it was just Becky in the frame.

“We made good use of the two weeks,” Becky continued, “and we hope you’re not sore, except in all the right ways.” An orange suddenly flew into the screen, presumably from June-from-last-night offscreen. “And if everything worked out, then maybe now you can guess at least one of the triggered words I planted…”

The couple turned to each other, each squinting as they thought about it, and each landing on the answer at the same time.

“Expecting!” they yelled in unison, together with Becky on screen.

“So, if everything went as planned, then all I have left to say is…” And together with a snap of her fingers, Becky repeated the words, “Wake up, babes!” The trigger worked. Their memories returned in full, and they turned to each other as if locking eyes for the first time that day. 

“Now, if you’ll excuse me, I’m going to go hypnotize myself into forgetting all the crazy shit you told me about your private time. Just kidding! Keep it weird, you sickos! Goodbye!”

The video ended, the silence returned, and they basked in all of the morning’s revelations. And when the moment passed, they reached the same conclusion, communicated with a gleam in their eyes and a twitch of their lips.

Their breakfast was going to get cold. Their bed was waiting. They were ready to begin.

reddit.com
u/Beautiful_Demand897 — 1 day ago

Wake Up, Babe [M20sF20s] [CD] [oral] [prostate play] [plot twists] [slow burn]

Riley woke up in a haze to a half-empty bed. He slept in later than usual. Not by a lot, but his morning routine had been fixed for so long that seeing the sun at a different point in the sky was disorienting by itself.

The extra space on the queen-size mattress also threw him off, but not as much as realizing that he was naked under the sheets. He couldn’t remember the last time he’d slept completely naked. But then, he also couldn’t remember much about the night before. He couldn’t quite put his finger on when he crawled into bed, what he was up to beforehand, and whether June was there at the time. It’s not that he always went to bed and woke up at the exact same time as his fiancée. But he usually knew when they were on different schedules, whether that was due to his work hours or her PhD studies.

The bedroom was silent except for the sounds that seeped in through the closed window and the door. Intermixed with the sounds of traffic from the street three floors below, Riley could just barely make out June’s muted voice. He couldn’t hear what she was saying, but her tone and cadence suggested a casual conversation with an acquaintance. There wasn’t a second voice, just gaps when June was silent. That suggested June was on a phone call, which led Riley to recall that her fellow PhD candidate and best friend Becky had gone to Paris for the summer. He calculated the time zone conversion from 7:30am in Portland to 4:30pmin Paris, and the sequence of events that led him to wake up later than usual to an empty bed suddenly fell into place.

He rolled out of bed, feeling an odd tingle up and down his legs as he did. He chalked it up to his bare skin sliding over their silk sheets without the usual intermediary of his flannel pajamas. Why his pants were missing remained a mystery. He planted his feet on the shag carpet of their bedroom and felt another odd sensation. This time, it was his calf muscles, which felt unexpectedly (almost painfully) stretched by lying flat on the ground. He’d woken up to a Charley horse in his legs before. This was not that. This was another morning mystery.

He opened the top drawer of his dresser and absent-mindedly pulled out the first pair of underwear with one hand while the other rubbed the sleep out of his eyes. He slipped his feet in one leg at a time, pulled the underwear into place, and switched drawers to grab a pair of socks. This time, he noticed that his hand landed on something unexpected. Where he expected to find a rolled-up pair of blue dress socks, his left hand instead grabbed a folded-up bunch of beige nylon. Not a pair of socks but pantyhose. He paused and scanned the rest of the drawer, only to find that it was filled almost entirely with hosiery—pantyhose, tights, and stockings. 

He was thrown by what he saw, but not quite because of what he saw. What threw him off is that it didn’t surprise him. He had the odd sensation that the drawer had exactly what it should, that whatever he used to find there—his dress socks, casual socks, and gym socks—had been moved. But he couldn’t recall where. We must have reorganized everything, he thought to himself. But when? Were we high? Did I get black-out drunk last night, right around the time we decided to switch dressers?

He didn’t feel hungover, and he didn’t see any empty bottles or roaches on the bedside tables.

Before he could test this theory further by checking June’s dresser on the other side of their bedroom, he felt a compulsion, an impulse. His left hand grabbed hold of the pantyhose and lifted them up from the drawer. The two legs unfurled before him, and he could tell immediately that these were not June’s. He hadn’t committed her size to memory, but he could tell that the legs were far too long for her 5’4” frame. When he held the dangling pair against his own waist, though, the length appeared to be just right. 

A word suddenly manifested in his head. It flashed like a theater marquee, like a billboard in his mind, and it wouldn’t go away.

“Mine.”

No, he thought, this isn’t mine. But that thought was overwhelmed by the sheer force of the insistent word.

“Mine.”

The word had a force that compelled his right hand to grab the opposite end of the waistband and compelled his feet to shift over to the empty bed. He sat down, feeling almost like his muscles and joints were on rails. The movements of his hands were mindless, driven by pure muscle memory like tying his shoelaces or signing his name. 

His hands rolled up one leg of the pantyhose until he reached the reinforced toe. Then his leg rose to position for his foot to enter and be encased. He could only pause the motion of his body through conscious will. 

It wasn’t the first time he’d put on a pair of hosiery like this. He’d tried it once in high school, acting on a dare from his girlfriend for her amusement. He was clumsy and yanked them up like gym socks, tearing a run from top to bottom that made her girlfriend howl and hit him in a fake rage.

This time, his hands weren’t clumsy. They were delicate and intentional. The instant he stopped willing his hands to stop, they continued to roll the first leg up, gliding over his smooth, hairless leg, before moving to the second and repeating the process.

Smooth. Hairless. Legs. Another mystery!

In a flash, the hose were rolled up to his thighs, and without thinking, he stood up to pull the waistband over his underwear. It happened so fast and effortlessly that he barely had time to process his latest discovery. That’s why the sheets felt different, he realized. 

He sat back down and ran his hands up and down over his nylon-encased legs as he tried to pinpoint exactly when and why he (or someone else?) had shaved his legs. The feeling was electric. He couldn’t recall anything like it. Every nerve ending from his hip to his ankle responded to his hands rubbing over them, coming alive to their touch.

He was addicted immediately. He couldn’t stop sliding his hands up and down and back again. The sensation captured him so much that he didn’t hear June’s cadence switch. He didn’t notice that her conversation was winding down. He didn’t catch the footfalls or the sound of her hand on the bedroom doorknob.

“Hey, babe!” 

June froze at the doorstep and locked eyes on Riley, who looked up at her like a deer right before a collision.

“Hi!” His voice snapped out of him like a triggered mousetrap.

She studied his eyes and his pose, his two hands frozen above his left knee. 

“Everything okay?”

He didn’t know how to answer. One part of his brain wanted to say that nothing about the morning had been “okay.” That voice was overruled by the rest of his brain, which—much to his surprise and confusion—felt very much “okay” with the situation despite it all.

He settled on a response that felt objectively true, even if his mind debated exactly why it was so: “I’m sure this looks strange.” 

June nodded with a smirk. “Yeah, you could say that.”

“I found, um, this,” he said with his hands open to display his legs, “in my dresser, and it just sort of happened.”

“Yeah, okay,” she replied flatly, leaving Riley to wonder if she even noticed that her fiancé was sitting on their bed wearing nothing but a pair of pantyhose over shaved legs.

“It just felt…” He paused to consider the right word. Like the word “Mine”, one word quickly manifested itself and took over his brain. “Natural. It felt natural.”

“Well …,” June said and paused, causing a sudden panic in Riley that she might say nothing more but instead just pack up and leave him. But her pause was brief, and the next word that came out of her mouth was a softly spoken “yeah.”

“Yeah?”, he asked, more baffled than relieved by her answer and her tone.

He could see her processing. He’d seen that furrowed brow on her face plenty of times before, usually hovering over a keyboard or a table full of notes and research. It was the focused intensity of her PhD-powered brain working something out. 

Her face and voice shifted to a tenor he’d seen come out of her whenever she had to teach an undergraduate course or mentor a younger student. She sat down next to him, laid a hand on his nylon-encased thigh, looked into his eyes with cool confidence, and said, “Tell me what’s been happening.”

“Well…” Riley walked through the last half hour of the morning, beat by beat. He spoke with the anxious precision of a student in the principal’s office. He didn’t think he’d done anything wrong. Not exactly. But he didn’t understand what was happening, and so his guard was up. “And then you came in.”

“Does anything else feel odd or unusual this morning?”

Now it was his turn to furrow his brow. That question implied that what he’d just described—waking up naked with short-term amnesia and crossdressing on autopilot—wasn’t enough.  That all of that might just be the tip of some even crazier iceberg he had yet to hit.

“I guess that my ankles also feel weird. I think I just slept on them wrong.”

“Like a cramp? A Charley horse?”

“Like that, but also no, not like that. My calves just feel tense.”

“All the time?

“When I stand up.”

“Show me.”

Now, Riley felt like a laboratory test subject. He suddenly stopped seeing June as his fiancée and started to see her as a lab technician. He stood up as requested and planted his feet flat on the ground.

June looked down with interest, looked back up at Riley, shrugged, and said, “Well, sure.”

“Sure, what!??” The more June seemed nonplussed, the more confused he grew.

“That’s going to happen to your legs after—wait just a second…” June abruptly shifted gears mid-sentence, suddenly stood up, and walked down the hall. Riley’s mind felt unmoored to a brand-new degree. He could feel reality shifting around him, and he began to wonder if he even knew where he was, or if he had maybe slipped into an alternate universe.

June returned to the room holding a pair of blue closed-toe block heels. She set them down in front of Riley, with the heels facing him and the toes facing away. She held out her hands to present them to him as if no further explanation was needed.

“You want me to—” She immediately nodded in response, with her eyes opened wide as if the answer was obvious. He performatively popped his eyebrow and vocalized a sigh as if to say, Well, why not? The day’s been weird enough already, so might as well keep going.

His feet slipped easily into the shoes. The size was just right, and the insides had noticeably molded to the specific shape of his feet. The lift of the heels took away the discomfort in his calves, and to his surprise, he felt perfectly balanced and (that word again) natural.

“Better?”

“Yeah.” He was genuinely surprised, but again, mostly by how little surprised the better part of his body and mind felt.

“When you’re in heels most of the time, the calves start to adjust until standing and walking without heels will actually feel uncomfortable.”

Her explanation made perfect sense. And yet, simultaneously, he felt like a bomb had just exploded in the room.

“Most of the time!?”

June’s eyes opened wide, and she mouthed a silent “Wow!” Her brow furrowed again as her mind returned to processing mode. She disappeared from the room briefly to grab a notepad and pen from the study room next door.

“Okay, sit down. We need to dig into this.” Riley did as she asked, sitting next to her on the bed as she scribbled into her notepad. He was equal parts nervous and excited, feeding off of the buzz radiating all around her.

“So,” she said with the tone of a Special Announcement, “we’ve been engaged in an experiment. You and I. With your full consent, I have been practicing hypnosis on you as research for my thesis.”

“Um, okay.” Every word she spoke had a ring of truth to it, but nothing she said conjured any specific memories in his head. She must have sensed his reservation because she disappeared again into the other room to grab an iPad.

“Here,” she said, pulling up a video on the tablet. The video showed Riley and June sitting next to each other at their dining room table (the iPad must have been propped up on the other side of the table). 

In the video, June looked back and forth from Riley to the camera as she spoke. 

“So, Riley Johnson, do you understand the project as I’ve described it, can you summarize it for us, and do I have your full consent, confirmed this Tuesday, January 5, 2022, at 4:35pm, in Portland, Oregon?”

Video Riley burst out laughing along with June. He also darted his eyes back and forth between her and the camera and replied, “Yes, I, Riley Milhouse Johnson, do hereby consent, fully… mind, body, and soul… to participate in a hypnosis experiment to switch my entire wardrobe from masculine, um…”

“Masculine-presenting,” June completed for him.

“Masculine-presenting,” Riley continued, “to feminine-presenting. The goal and purpose will be to change my perception of these clothes—”

“And your related behavior,” June added.

“—and my behavior to the point that I do not recognize that a change has occurred, but I will be going into this project with full knowledge and awareness, with consent to alter my perception, and waiving any liability that I may have against you, my soon-to-be wife—”

“—okay, stop, stop!”

The couple in the video laughed, and a moment later the video stopped. Riley stared at the paused image of himself and his fiancée, laughing and wrestling. Then he looked down again at his shaved and shimmering legs.

“Okay,” he said with acceptance. “So, okay. Here we are. So, was my amnesia or whatever it was this morning… was that also part of the process? Is that how I wake up every morning?”

“No, not at all,” June said, with a hint of concern in her voice. “I don’t understand why that happened. This is the first time you’ve had any kind of memory loss, and we’re a couple of months into the process.”

Riley’s eyes widened. He thought back and tried to recall how the last couple of months had gone. He could remember sporadic moments of their lives, working remotely, going to dinner, seeing friends… but every memory was foggy and the specific details felt just out of reach. When he tried to recall exactly what he was doing at any given time, how he felt, or what he was wearing, the moment slipped through his mind.

“So, have I been going out like this?  On Zoom calls? Out with friends or shopping?”

“You’ve been, well, the term is ‘underdressing’ whenever we’re out in public or you’re live on camera. That means you’ve had, you know, your old boy clothes on. But underneath it’s been—”

“This,” Riley finished.

June shrugged and smiled.

“I think I’d remember shaving my legs, though,” he said, poking at the story and also testing his own choppy memory.

“How much do you remember shaving? I mean, in general, not just recently?”

“Well, I know I shave my face. About once or twice a week.” He raised his hand to feel his cheek, noticing as he did that his nails were smoothly filed and painted teal.

“But if you think about shaving, do you remember specifics, like exactly when you shaved, for how long, what time of day?”

He studied his hands as he pondered her question. “I guess I don’t. I just have the vague recollection that it’s something I regularly do. Just like, um…”

“Just like caring for your nails,” she offered.

“Yeah.”

June reached out to hold his right hand with her own well-manicured hands and looked softly into his eyes. “You were changing your routine in ways you didn’t really notice. It folded into the background of your day-to-day routine. It was like washing your hands or folding laundry. Shaving your legs and painting your nails became routine, something you wouldn’t even notice or bother remembering.”

Riley considered everything she said. It all made intuitive sense, and yet it still felt like something was missing. They were still left with the mystery of why this morning was different.

“Maybe you can tell me more about how this works, then. I mean, you’ve told me about clinical hypnosis for therapeutic purposes before. But I’ve never seen you do it.” He realized how funny that was for him to say, since he’d obviously been seeing it first-hand for months now. They gave each other a knowing look and laughed.

“Yeah, so, it’s a combination of things,” June said, amused at the novelty of explaining to her fiancé-slash-patient the very thing he’s been witnessing her do for so long now. “We’ve had regular sessions, which take about 30-60 minutes of continuous hypnotic treatment. Out of that process, you’ve developed a few triggers. Some of them are conscious, some are unconscious. It’s mostly a matter of repeating patterns and keeping things consistent. Positive reinforcement, small rewards here and there. Eventually, though, I needed to reinforce your triggers less and less, and all of the reinforced behaviors faded from your conscious mind and became part of your natural perspective.”

That word again. Natural.

“So, what are the triggers?”

“Some triggers are words or phrases. Some are not. Like—” June demonstrated by casually lifting the pointer finger of her right hand towards Riley. Her finger softly landed on his right shoulder and slid down to his nipple. Then she repeated the motion on the other side of his body, starting again from his left shoulder down to the other nipple.

Riley’s eyes twitched immediately, and in a nearly involuntary reaction, his arms crisscrossed over his body.

“How do you feel?”, June asked clinically.

“I feel naked,” he answered immediately.

“Well, you are naked. Do you feel more naked now than you were a moment ago?”

“I feel…” A word popped into his mind. He struggled to find another word, but he realized that it was the only word that felt right. “Topless.”

“Well, you can fix that,” June suggested, nodding her head towards his dresser.

Riley nodded and walked over to pull open the third drawer from the top. Inside, he saw a row of shirts. He grabbed the first one he saw, a grey V-neck undershirt, and he slipped it on. The soft fabric felt comfortable but also somehow incomplete.

“How do you feel now?”

Riley thought about it. He listened to his body. He gave the only answer he could. “I feel less naked, but I don’t feel … dressed.”

“What would make you feel dressed?” Her questions were clearly leading him, and he knew it. But he also felt in his bones that she was asking him the right questions, and each question only had one right answer.

He pulled off the shirt, dropped it to the ground, and turned back to the dresser to close the third drawer and open the fourth. In that drawer, he found exactly what he expected to find. He pulled out a pink, wireless, soft-cup bra and slipped it over his arms. As he did, the word “Mine!” screamed again in his brain. His hands met behind his back, and with ease, his fingers grabbed the two back-ends of the bra and clipped the hooks into place. Switching back from the fourth drawer to the third drawer, he pulled out a silk blouse patterned with blue and white stripes. He slipped it on, and it fell naturally on top of his bra, the A-cups giving subtle curves to his otherwise flat torso.

“And now?” June asked.

“Now, I feel dressed. Well, half-dressed,” he said, looking down at his legs and giving them both a laugh. “Tights may be pants but—”

“No, pantyhose definitely are not,” June agreed and laughed again. 

She smiled softly at her half-naked fiancé and nodded towards their bedroom closet door. Riley walked over to the closet, feeling again like he was on rails as he opened the door, reached directly for a particular hanger in the middle of the closet, and removed a sky-blue pleated midi skirt. With deft motions, he held the waistband of the skirt with both hands while he stepped gingerly into the garment. He remained perfectly balanced on one leg and then the other, and when he was done, the outfit was complete.

Riley closed the closet door and gave himself a good look in the full-length mirror on the other side. Every article fit his body and even complemented his body shape. It was jarring seeing himself like that but also—again, that word returned to his mind—"natural.”

“I take it we weren’t going for ‘drag queen.’”

“No, not at all. Your style has been very conservative, perfectly office appropriate.”

“Okay, so…” He thought carefully about the question rolling around in his head. “What was the goal exactly?”

June blushed. It was the first time that morning he’d seen her react that way. Until then, she hadn’t been even the slightest bit shy seeing her man in full women’s garb. What had suddenly made her so nervous?

“Do you want me to become a woman?” Everything up to that point had felt in some way normal to Riley, despite it all. But that question felt like he had taken a step off the rails.

“Oh no,” she replied right away, “I mean, if you were trans, we could figure that out. I’d support you. We’d make it work. But we always knew you were cis, straight and all that.”

“Okay, right,” he said, agreeing with her and believing everything she said. “Was this just to see if you could do it, for the sake of your PhD thesis?”

“It’s … yeah, the thesis concerns fluid gender identities and whether we can break down barriers between the sexes. Is there anything intrinsically quote-unquote male about pants and quote-unquote female about a skirt, for example? And why shouldn’t a man wear a bra if it makes him comfortable and accentuates his body’s curves? And—”

“Why me, though?” Riley could tell she was avoiding something. He knew her every verbal tick and tell.

Her cheeks blushed even harder and she turned her eyes down. Slowly, carefully, she said, “You had your own motives.”

Riley tilted his head toward her and held out his hand in an open gesture.

“You had this hang up…”

And suddenly, he knew exactly what she meant. “Oh.”

“Yeah, so, you were always nervous about, you know—”

“Going down on you.”

She nodded, her cheeks still red. “We unpacked that, you know. Your hyper-masculine dad and your brothers, the frat atmosphere, the—let’s just say it—toxic swirl of homophobia and misogyny you grew up surrounded by. Telling you that going down on someone, even a guy going down on a girl was…”

“Effeminate.” Riley completed her thought, nodding as another piece fell into place.

“We figured, since I was looking for a test subject anyways—”

“We figured, let’s see if giving me a new perspective on gender helped to strip away my apprehensions.”

June nodded enthusiastically, and another portion of Riley’s memory came back into focus. “And it worked,” he said, and June nodded even harder and faster. “Well,” he added with a Cheshire Cat smile, “let’s not interrupt the experiment in that case.”

June’s face beamed, switching in a heartbeat from self-conscious to ecstatic. Riley moved over to where she sat on the bed and, with the pointer finger of his right hand, pushed her gently backward onto the bed. He dropped to his knees, nudged each of her legs apart from the other, and unzipped the zipper of her grey dress pants. With his fingers looped into the belt loops, he pulled her pants down to her ankles. He did the same with her yellow panties, so that her ankles met and her legs bent to form a rectangle.

Riley leaned into the space between her thighs and discovered that his hang-ups around cunnilingus had been purged entirely from his mind. He dove in without hesitation, letting his tongue explore every fold of her. He could feel her muscles tense and her body writhe. He could tell her hands were gripping the sheets and her teeth were biting her bottom lip. His mouth settled on top of her clit, which was like a small, engorged pebble, slick and covered in the mixture of her fluids and his saliva. He alternated between sucking and licking, letting her fill his mouth with her sweetness, swallowing some of her and letting the rest spill back out as lubricant.

He remembered an old trick he’d heard once, to spell words with his tongue over her clit and labia. The trick served him well. After spelling her name and then his, the words that continued to pop into his mind made it out of his mouth and onto her body: “Mine.” “Natural.”

On the last letter of the last word, her body finally surged. Every muscle in her body seemed to contract and spasm at once and in waves. Her mouth opened, her teeth releasing her lips and letting out a scream that must have been heard two floors in either direction from their apartment. And then her body collapsed.

“Get up here,” she managed to say between panting breaths. He obliged, climbing up to meet her face. With the last of her strength, she lifted herself enough to meet his lips, kissing and lapping up the remnants of her around his mouth. “You must be ready for a go yourself.” 

She wasn’t wrong, but he suddenly noticed that something felt different. His blood had risen along with his passions. He wanted—he needed a release. And yet, something felt different. It felt (yes, again) natural, and yet, still, different.

Riley stood up over her and, unsure as to what felt different, tried to deflect.

“I can give you a striptease, but it might be funny when I go from all of this down to my plain old boxer briefs.”

June, still panting, tilted his head and looked up at him with a peculiar expression. Unsure of what he meant, she circled her fingers in the air in a wordless gesture of “let’s go, get on with it!”

Now it was Riley’s turn to blush. He couldn’t explain it, but something between his legs felt off. He worried that, in all of the hypnotic shenanigans, maybe his libido had been impacted. He pulled off his blouse, slid his skirt down to the ground, stepped out of his heels, and pulled his pantyhose off one leg at a time.

And there he stood, down to his underwear. Pink panties that matched his pink bra.

“Riley, those aren’t boxers.”

“No, they aren’t!” he yelped in genuine surprise.  He hadn’t even looked in the drawer when he had pulled them out and slipped them on. He was on autopilot the entire time.

“You didn’t notice when you put them on?”

“I didn’t, I just assumed they were—”

“Did you think, ‘Mine?’” The word sent a shiver down his body. “Did you think it was ‘natural’?” His body shivered again.

“Oh, my god.” His entire body tingled. He felt light as a feather. He felt jolts of electricity running throughout his body in every direction.

“Did you even notice…?” June trailed off and gestured with her right hand toward the mound in his panties.

He brought a hand down on top of it and felt, for the first time, that his member was encased within a plastic sheath and that sheath had a ring that went around the base of his genitals. He was wearing a chastity cage, and he didn’t even realize it.

“Natural,” June said again, causing his testicles to contract and his penis to press desperately against the downward pressing sheath. She lifted her head up and propped herself up by her elbows. “You thought it would help with remolding your mindset. But don’t worry, we have ways of relieving you.”

Sitting up so her head was level with his hips, she pulled his panties down to the ground and exposed the black cage. With one hand, she grabbed his balls and gently rolled them around in her fingers while he moaned.

“Now, lie down on your back,” she purred to him. “I’ll take what’s mine.

He complied immediately, without the slightest hint of resistance. He was back in bed, just as he’d begun but with a completely clear mind. He was also, once again, completely naked, although not as naked as he had thought he was when he first woke. June poked into the closet, just past his field of vision, although he could hear her rummage. She joined him in bed, setting herself up so that she could access his midsection. She gently spread his legs apart, and after a generous squeeze from a bottle she’d brought from the closet, she introduced a single finger into his backside. Gently working herself inside of him, sliding in and out slowly but steadily, she massaged his muscles into relaxing enough to welcome a second, well-lubricated finger.

As her fingers worked their way to his prostate, she positioned her other hand on the other side of his body. In her hand was a small device, pink and shaped like a large tadpole. The device sprang to life with the push of a button and vibrated quietly and—at first—gently. She slowly moved the vibrator from the tip of the cage down to the base, exploring one side of the shaft and then the other. Now it was Riley’s turn to grip the sheets and suppress a moan.

June knew he was hers to mold and manipulate. She could make him shake and quiver with a word, and she knew where every button was on his body. She took her time with him, slowing the vibrations down and then speeding them up, pressing his prostate down hard and then soft, flicking to tease and then taking him completely.

When she was ready, as she heard the word “please” escape from his clenched throat, she gave him everything. His body quaked, nearly shaking her off of him as he convulsed and his semen spurt from his cage over the sheets, off of the bed and onto the carpet.

And then his body collapsed, and he said to her, “Come here.”

They lay in each other’s arms, each feeling at once completely empty and completely full. June’s eyes fluttered as sleep threatened to befall her. She forced herself up to avoid passing out.

“Riley, we can’t both go back to sleep. You have work, and I have a report to complete. Besides, I already lost part of the morning to … oh … shit, that’s it!”

“What’s ‘it’?” Riley propped himself up, eager to hear what his fiancée had realized.

“That’s what happened today! I got up early to catch my friend Becky on Paris time.”

“Yeah?”

“And so I wasn’t there when you woke up! I always start the day by saying…” June turned to Riley and gently caressed his face with her hand, “Wake up, babe.”

That phrase. It was the most powerful trigger she had installed in him. It reset his mindset in a flash and brought his world into focus like prescription glasses. Like a switch, his muscles instantly relaxed, the fog lifted from his memory, and he knew who he was with fresh clarity.

He tilted his head towards his woman, caressed her face in return, and said to her in his softest, sweetest voice, “Good morning, babe. I’m here. Now, where are my clothes?”

reddit.com
u/Beautiful_Demand897 — 4 days ago
▲ 9 r/cdstoriesgonewild+1 crossposts

Wake Up, Babe [crossdressing] [oral] [gentle femdom] [plot twists]

Riley woke up in a haze to a half-empty bed. He had slept in later than usual. Not by a lot, but his morning routine had been fixed for so long that seeing the sun at a different point in the sky was disorienting by itself.

The extra space on the queen-size mattress also threw him off, but not as much as realizing that he was naked under the sheets. He couldn’t remember the last time he’d slept completely naked. But then, he also couldn’t remember much about the night before. He couldn’t quite put his finger on when he crawled into bed, what he was up to beforehand, and whether June was there at the time. It’s not that he always went to bed and woke up at the exact same time as his fiancée. But he usually knew when they were on different schedules, whether that was due to his work hours or her PhD studies.

The bedroom was silent except for the sounds that seeped in through the closed window and the door. Intermixed with the sounds of traffic from the street three floors below, Riley could just barely make out June’s muted voice. He couldn’t hear what she was saying, but her tone and cadence suggested a casual conversation with an acquaintance. There wasn’t a second voice, just gaps when June was silent. That suggested June was on a phone call, which led Riley to recall that her fellow PhD candidate and best friend Becky had gone to Paris for the summer. He calculated the time zone conversion from 7:30am in Portland to 4:30pmin Paris, and the sequence of events that led him to wake up later than usual to an empty bed suddenly fell into place.

He rolled out of bed, feeling an odd tingle up and down his legs as he did. He chalked it up to his bare skin sliding over their silk sheets without the usual intermediary of his flannel pajamas. Why his pants were missing remained a mystery. He planted his feet on the shag carpet of their bedroom and felt another odd sensation. This time, it was his calf muscles, which felt unexpectedly (almost painfully) stretched by lying flat on the ground. He’d woken up to a Charley horse in his legs before. This was not that. This was another morning mystery.

He opened the top drawer of his dresser and absent-mindedly pulled out the first pair of underwear with one hand while the other rubbed the sleep out of his eyes. He slipped his feet in one leg at a time, pulled the underwear into place, and switched drawers to grab a pair of socks. This time, he noticed that his hand landed on something unexpected. Where he expected to find a rolled-up pair of blue dress socks, his left hand instead grabbed a folded-up bunch of beige nylon. Not a pair of socks but pantyhose. He paused and scanned the rest of the drawer, only to find that it was filled almost entirely with hosiery—pantyhose, tights, and stockings. 

He was thrown by what he saw, but not quite because of what he saw. What threw him off is that it didn’t surprise him. He had the odd sensation that the drawer had exactly what it should, that whatever he used to find there—his dress socks, casual socks, and gym socks—had been moved. But he couldn’t recall where. We must have reorganized everything, he thought to himself. But when? Were we high? Did I get black-out drunk last night, right around the time we decided to switch dressers?

He didn’t feel hungover, and he didn’t see any empty bottles or roaches on the bedside tables.

Before he could test this theory further by checking June’s dresser on the other side of their bedroom, he felt a compulsion, an impulse. His left hand grabbed hold of the pantyhose and lifted them up from the drawer. The two legs unfurled before him, and he could tell immediately that these were not June’s. He hadn’t committed her size to memory, but he could tell that the legs were far too long for her 5’4” frame. When he held the dangling pair against his own waist, though, the length appeared to be just right. 

A word suddenly manifested in his head. It flashed like a theater marquee, like a billboard in his mind, and it wouldn’t go away.

“Mine.”

No, he thought, this isn’t mine. But that thought was overwhelmed by the sheer force of the insistent word.

“Mine.”

The word had a force that compelled his right hand to grab the opposite end of the waistband and compelled his feet to shift over to the empty bed. He sat down, feeling almost like his muscles and joints were on rails. The movements of his hands were mindless, driven by pure muscle memory like tying his shoelaces or signing his name. 

His hands rolled up one leg of the pantyhose until he reached the reinforced toe. Then his leg rose to position for his foot to enter and be encased. He could only pause the motion of his body through conscious will. 

It wasn’t the first time he’d put on a pair of hosiery like this. He’d tried it once in high school, acting on a dare from his girlfriend for her amusement. He was clumsy and yanked them up like gym socks, tearing a run from top to bottom that made her girlfriend howl and hit him in a fake rage.

This time, his hands weren’t clumsy. They were delicate and intentional. The instant he stopped willing his hands to stop, they continued to roll the first leg up, gliding over his smooth, hairless leg, before moving to the second and repeating the process.

Smooth. Hairless. Legs. Another mystery!

In a flash, the hose were rolled up to his thighs, and without thinking, he stood up to pull the waistband over his underwear. It happened so fast and effortlessly that he barely had time to process his latest discovery. That’s why the sheets felt different, he realized. 

He sat back down and ran his hands up and down over his nylon-encased legs as he tried to pinpoint exactly when and why he (or someone else?) had shaved his legs. The feeling was electric. He couldn’t recall anything like it. Every nerve ending from his hip to his ankle responded to his hands rubbing over them, coming alive to their touch.

He was addicted immediately. He couldn’t stop sliding his hands up and down and back again. The sensation captured him so much that he didn’t hear June’s cadence switch. He didn’t notice that her conversation was winding down. He didn’t catch the footfalls or the sound of her hand on the bedroom doorknob.

“Hey, babe!” 

June froze at the doorstep and locked eyes on Riley, who looked up at her like a deer right before a collision.

“Hi!” His voice snapped out of him like a triggered mousetrap.

She studied his eyes and his pose, his two hands frozen above his left knee. 

“Everything okay?”

He didn’t know how to answer. One part of his brain wanted to say that nothing about the morning had been “okay.” That voice was overruled by the rest of his brain, which—much to his surprise and confusion—felt very much “okay” with the situation despite it all.

He settled on a response that felt objectively true, even if his mind debated exactly why it was so: “I’m sure this looks strange.” 

June nodded with a smirk. “Yeah, you could say that.”

“I found, um, this,” he said with his hands open to display his legs, “in my dresser, and it just sort of happened.”

“Yeah, okay,” she replied flatly, leaving Riley to wonder if she even noticed that her fiancé was sitting on their bed wearing nothing but a pair of pantyhose over shaved legs.

“It just felt…” He paused to consider the right word. Like the word “Mine”, one word quickly manifested itself and took over his brain. “Natural. It felt natural.”

“Well …,” June said and paused, causing a sudden panic in Riley that she might say nothing more but instead just pack up and leave him. But her pause was brief, and the next word that came out of her mouth was a softly spoken “yeah.”

“Yeah?”, he asked, more baffled than relieved by her answer and her tone.

He could see her processing. He’d seen that furrowed brow on her face plenty of times before, usually hovering over a keyboard or a table full of notes and research. It was the focused intensity of her PhD-powered brain working something out. 

Her face and voice shifted to a tenor he’d seen come out of her whenever she had to teach an undergraduate course or mentor a younger student. She sat down next to him, laid a hand on his nylon-encased thigh, looked into his eyes with cool confidence, and said, “Tell me what’s been happening.”

“Well…” Riley walked through the last half hour of the morning, beat by beat. He spoke with the anxious precision of a student in the principal’s office. He didn’t think he’d done anything wrong. Not exactly. But he didn’t understand what was happening, and so his guard was up. “And then you came in.”

“Does anything else feel odd or unusual this morning?”

Now it was his turn to furrow his brow. That question implied that what he’d just described—waking up naked with short-term amnesia and crossdressing on autopilot—wasn’t enough.  That all of that might just be the tip of some even crazier iceberg he had yet to hit.

“I guess that my ankles also feel weird. I think I just slept on them wrong.”

“Like a cramp? A Charley horse?”

“Like that, but also no, not like that. My calves just feel tense.”

“All the time?

“When I stand up.”

“Show me.”

Now, Riley felt like a laboratory test subject. He suddenly stopped seeing June as his fiancée and started to see her as a lab technician. He stood up as requested and planted his feet flat on the ground.

June looked down with interest, looked back up at Riley, shrugged, and said, “Well, sure.”

“Sure, what!??” The more June seemed nonplussed, the more confused he grew.

“That’s going to happen to your legs after—wait just a second…” June abruptly shifted gears mid-sentence, suddenly stood up, and walked down the hall. Riley’s mind felt unmoored to a brand-new degree. He could feel reality shifting around him, and he began to wonder if he even knew where he was, or if he had maybe slipped into an alternate universe.

June returned to the room holding a pair of blue closed-toe block heels. She set them down in front of Riley, with the heels facing him and the toes facing away. She held out her hands to present them to him as if no further explanation was needed.

“You want me to—” She immediately nodded in response, with her eyes opened wide as if the answer was obvious. He performatively popped his eyebrow and vocalized a sigh as if to say, Well, why not? The day’s been weird enough already, so might as well keep going.

His feet slipped easily into the shoes. The size was just right, and the insides had noticeably molded to the specific shape of his feet. The lift of the heels took away the discomfort in his calves, and to his surprise, he felt perfectly balanced and (that word again) natural.

“Better?”

“Yeah.” He was genuinely surprised, but again, mostly by how little surprised the better part of his body and mind felt.

“When you’re in heels most of the time, the calves start to adjust until standing and walking without heels will actually feel uncomfortable.”

Her explanation made perfect sense. And yet, simultaneously, he felt like a bomb had just exploded in the room.

“Most of the time!?”

June’s eyes opened wide, and she mouthed a silent “Wow!” Her brow furrowed again as her mind returned to processing mode. She disappeared from the room briefly to grab a notepad and pen from the study room next door.

“Okay, sit down. We need to dig into this.” Riley did as she asked, sitting next to her on the bed as she scribbled into her notepad. He was equal parts nervous and excited, feeding off of the buzz radiating all around her.

“So,” she said with the tone of a Special Announcement, “we’ve been engaged in an experiment. You and I. With your full consent, I have been practicing hypnosis on you as research for my thesis.”

“Um, okay.” Every word she spoke had a ring of truth to it, but nothing she said conjured any specific memories in his head. She must have sensed his reservation because she disappeared again into the other room to grab an iPad.

“Here,” she said, pulling up a video on the tablet. The video showed Riley and June sitting next to each other at their dining room table (the iPad must have been propped up on the other side of the table). 

In the video, June looked back and forth from Riley to the camera as she spoke. 

“So, Riley Johnson, do you understand the project as I’ve described it, can you summarize it for us, and do I have your full consent, confirmed this Tuesday, January 5, 2022, at 4:35pm, in Portland, Oregon?”

Video Riley burst out laughing along with June. He also darted his eyes back and forth between her and the camera and replied, “Yes, I, Riley Milhouse Johnson, do hereby consent, fully… mind, body, and soul… to participate in a hypnosis experiment to switch my entire wardrobe from masculine, um…”

“Masculine-presenting,” June completed for him.

“Masculine-presenting,” Riley continued, “to feminine-presenting. The goal and purpose will be to change my perception of these clothes—”

“And your related behavior,” June added.

“—and my behavior to the point that I do not recognize that a change has occurred, but I will be going into this project with full knowledge and awareness, with consent to alter my perception, and waiving any liability that I may have against you, my soon-to-be wife—”

“—okay, stop, stop!”

The couple in the video laughed, and a moment later the video stopped. Riley stared at the paused image of himself and his fiancée, laughing and wrestling. Then he looked down again at his shaved and shimmering legs.

“Okay,” he said with acceptance. “So, okay. Here we are. So, was my amnesia or whatever it was this morning… was that also part of the process? Is that how I wake up every morning?”

“No, not at all,” June said, with a hint of concern in her voice. “I don’t understand why that happened. This is the first time you’ve had any kind of memory loss, and we’re a couple of months into the process.”

Riley’s eyes widened. He thought back and tried to recall how the last couple of months had gone. He could remember sporadic moments of their lives, working remotely, going to dinner, seeing friends… but every memory was foggy and the specific details felt just out of reach. When he tried to recall exactly what he was doing at any given time, how he felt, or what he was wearing, the moment slipped through his mind.

“So, have I been going out like this?  On Zoom calls? Out with friends or shopping?”

“You’ve been, well, the term is ‘underdressing’ whenever we’re out in public or you’re live on camera. That means you’ve had, you know, your old boy clothes on. But underneath it’s been—”

“This,” Riley finished.

June shrugged and smiled.

“I think I’d remember shaving my legs, though,” he said, poking at the story and also testing his own choppy memory.

“How much do you remember shaving? I mean, in general, not just recently?”

“Well, I know I shave my face. About once or twice a week.” He raised his hand to feel his cheek, noticing as he did that his nails were smoothly filed and painted teal.

“But if you think about shaving, do you remember specifics, like exactly when you shaved, for how long, what time of day?”

He studied his hands as he pondered her question. “I guess I don’t. I just have the vague recollection that it’s something I regularly do. Just like, um…”

“Just like caring for your nails,” she offered.

“Yeah.”

June reached out to hold his right hand with her own well-manicured hands and looked softly into his eyes. “You were changing your routine in ways you didn’t really notice. It folded into the background of your day-to-day routine. It was like washing your hands or folding laundry. Shaving your legs and painting your nails became routine, something you wouldn’t even notice or bother remembering.”

Riley considered everything she said. It all made intuitive sense, and yet it still felt like something was missing. They were still left with the mystery of why this morning was different.

“Maybe you can tell me more about how this works, then. I mean, you’ve told me about clinical hypnosis for therapeutic purposes before. But I’ve never seen you do it.” He realized how funny that was for him to say, since he’d obviously been seeing it first-hand for months now. They gave each other a knowing look and laughed.

“Yeah, so, it’s a combination of things,” June said, amused at the novelty of explaining to her fiancé-slash-patient the very thing he’s been witnessing her do for so long now. “We’ve had regular sessions, which take about 30-60 minutes of continuous hypnotic treatment. Out of that process, you’ve developed a few triggers. Some of them are conscious, some are unconscious. It’s mostly a matter of repeating patterns and keeping things consistent. Positive reinforcement, small rewards here and there. Eventually, though, I needed to reinforce your triggers less and less, and all of the reinforced behaviors faded from your conscious mind and became part of your natural perspective.”

That word again. Natural.

“So, what are the triggers?”

“Some triggers are words or phrases. Some are not. Like—” June demonstrated by casually lifting the pointer finger of her right hand towards Riley. Her finger softly landed on his right shoulder and slid down to his nipple. Then she repeated the motion on the other side of his body, starting again from his left shoulder down to the other nipple.

Riley’s eyes twitched immediately, and in a nearly involuntary reaction, his arms crisscrossed over his body.

“How do you feel?”, June asked clinically.

“I feel naked,” he answered immediately.

“Well, you are naked. Do you feel more naked now than you were a moment ago?”

“I feel…” A word popped into his mind. He struggled to find another word, but he realized that it was the only word that felt right. “Topless.”

“Well, you can fix that,” June suggested, nodding her head towards his dresser.

Riley nodded and walked over to pull open the third drawer from the top. Inside, he saw a row of shirts. He grabbed the first one he saw, a grey V-neck undershirt, and he slipped it on. The soft fabric felt comfortable but also somehow incomplete.

“How do you feel now?”

Riley thought about it. He listened to his body. He gave the only answer he could. “I feel less naked, but I don’t feel … dressed.”

“What would make you feel dressed?” Her questions were clearly leading him, and he knew it. But he also felt in his bones that she was asking him the right questions, and each question only had one right answer.

He pulled off the shirt, dropped it to the ground, and turned back to the dresser to close the third drawer and open the fourth. In that drawer, he found exactly what he expected to find. He pulled out a pink, wireless, soft-cup bra and slipped it over his arms. As he did, the word “Mine!” screamed again in his brain. His hands met behind his back, and with ease, his fingers grabbed the two back-ends of the bra and clipped the hooks into place. Switching back from the fourth drawer to the third drawer, he pulled out a silk blouse patterned with blue and white stripes. He slipped it on, and it fell naturally on top of his bra, the A-cups giving subtle curves to his otherwise flat torso.

“And now?” June asked.

“Now, I feel dressed. Well, half-dressed,” he said, looking down at his legs and giving them both a laugh. “Tights may be pants but—”

“No, pantyhose definitely are not,” June agreed and laughed again. 

She smiled softly at her half-naked fiancé and nodded towards their bedroom closet door. Riley walked over to the closet, feeling again like he was on rails as he opened the door, reached directly for a particular hanger in the middle of the closet, and removed a sky-blue pleated midi skirt. With deft motions, he held the waistband of the skirt with both hands while he stepped gingerly into the garment. He remained perfectly balanced on one leg and then the other, and when he was done, the outfit was complete.

Riley closed the closet door and gave himself a good look in the full-length mirror on the other side. Every article fit his body and even complemented his body shape. It was jarring seeing himself like that but also—again, that word returned to his mind—"natural.”

“I take it we weren’t going for ‘drag queen.’”

“No, not at all. Your style has been very conservative, perfectly office appropriate.”

“Okay, so…” He thought carefully about the question rolling around in his head. “What was the goal exactly?”

June blushed. It was the first time that morning he’d seen her react that way. Until then, she hadn’t been even the slightest bit shy seeing her man in full women’s garb. What had suddenly made her so nervous?

“Do you want me to become a woman?” Everything up to that point had felt in some way normal to Riley, despite it all. But that question felt like he had taken a step off the rails.

“Oh no,” she replied right away, “I mean, if you were trans, we could figure that out. I’d support you. We’d make it work. But we always knew you were cis, straight and all that.”

“Okay, right,” he said, agreeing with her and believing everything she said. “Was this just to see if you could do it, for the sake of your PhD thesis?”

“It’s … yeah, the thesis concerns fluid gender identities and whether we can break down barriers between the sexes. Is there anything intrinsically quote-unquote male about pants and quote-unquote female about a skirt, for example? And why shouldn’t a man wear a bra if it makes him comfortable and accentuates his body’s curves? And—”

“Why me, though?” Riley could tell she was avoiding something. He knew her every verbal tick and tell.

Her cheeks blushed even harder and she turned her eyes down. Slowly, carefully, she said, “You had your own motives.”

Riley tilted his head toward her and held out his hand in an open gesture.

“You had this hang up…”

And suddenly, he knew exactly what she meant. “Oh.”

“Yeah, so, you were always nervous about, you know—”

“Going down on you.”

She nodded, her cheeks still red. “We unpacked that, you know. Your hyper-masculine dad and your brothers, the frat atmosphere, the—let’s just say it—toxic swirl of homophobia and misogyny you grew up surrounded by. Telling you that going down on someone, even a guy going down on a girl was…”

“Effeminate.” Riley completed her thought, nodding as another piece fell into place.

“We figured, since I was looking for a test subject anyways—”

“We figured, let’s see if giving me a new perspective on gender helped to strip away my apprehensions.”

June nodded enthusiastically, and another portion of Riley’s memory came back into focus. “And it worked,” he said, and June nodded even harder and faster. “Well,” he added with a Cheshire Cat smile, “let’s not interrupt the experiment in that case.”

June’s face beamed, switching in a heartbeat from self-conscious to ecstatic. Riley moved over to where she sat on the bed and, with the pointer finger of his right hand, pushed her gently backward onto the bed. He dropped to his knees, nudged each of her legs apart from the other, and unzipped the zipper of her grey dress pants. With his fingers looped into the belt loops, he pulled her pants down to her ankles. He did the same with her yellow panties, so that her ankles met and her legs bent to form a rectangle.

Riley leaned into the space between her thighs and discovered that his hang-ups around cunnilingus had been purged entirely from his mind. He dove in without hesitation, letting his tongue explore every fold of her. He could feel her muscles tense and her body writhe. He could tell her hands were gripping the sheets and her teeth were biting her bottom lip. His mouth settled on top of her clit, which was like a small, engorged pebble, slick and covered in the mixture of her fluids and his saliva. He alternated between sucking and licking, letting her fill his mouth with her sweetness, swallowing some of her and letting the rest spill back out as lubricant.

He remembered an old trick he’d heard once, to spell words with his tongue over her clit and labia. The trick served him well. After spelling her name and then his, the words that continued to pop into his mind made it out of his mouth and onto her body: “Mine.” “Natural.”

On the last letter of the last word, her body finally surged. Every muscle in her body seemed to contract and spasm at once and in waves. Her mouth opened, her teeth releasing her lips and letting out a scream that must have been heard two floors in either direction from their apartment. And then her body collapsed.

“Get up here,” she managed to say between panting breaths. He obliged, climbing up to meet her face. With the last of her strength, she lifted herself enough to meet his lips, kissing and lapping up the remnants of her around his mouth. “You must be ready for a go yourself.” 

She wasn’t wrong, but he suddenly noticed that something felt different. His blood had risen along with his passions. He wanted—he needed a release. And yet, something felt different. It felt (yes, again) natural, and yet, still, different.

Riley stood up over her and, unsure as to what felt different, tried to deflect.

“I can give you a striptease, but it might be funny when I go from all of this down to my plain old boxer briefs.”

June, still panting, tilted his head and looked up at him with a peculiar expression. Unsure of what he meant, she circled her fingers in the air in a wordless gesture of “let’s go, get on with it!”

Now it was Riley’s turn to blush. He couldn’t explain it, but something between his legs felt off. He worried that, in all of the hypnotic shenanigans, maybe his libido had been impacted. He pulled off his blouse, slid his skirt down to the ground, stepped out of his heels, and pulled his pantyhose off one leg at a time.

And there he stood, down to his underwear. Pink panties that matched his pink bra.

“Riley, those aren’t boxers.”

“No, they aren’t!” he yelped in genuine surprise.  He hadn’t even looked in the drawer when he had pulled them out and slipped them on. He was on autopilot the entire time.

“You didn’t notice when you put them on?”

“I didn’t, I just assumed they were—”

“Did you think, ‘Mine?’” The word sent a shiver down his body. “Did you think it was ‘natural’?” His body shivered again.

“Oh, my god.” His entire body tingled. He felt light as a feather. He felt jolts of electricity running throughout his body in every direction.

“Did you even notice…?” June trailed off and gestured with her right hand toward the mound in his panties.

He brought a hand down on top of it and felt, for the first time, that his member was encased within a plastic sheath and that sheath had a ring that went around the base of his genitals. He was wearing a chastity cage, and he didn’t even realize it.

“Natural,” June said again, causing his testicles to contract and his penis to press desperately against the downward pressing sheath. She lifted her head up and propped herself up by her elbows. “You thought it would help with remolding your mindset. But don’t worry, we have ways of relieving you.”

Sitting up so her head was level with his hips, she pulled his panties down to the ground and exposed the black cage. With one hand, she grabbed his balls and gently rolled them around in her fingers while he moaned.

“Now, lie down on your back,” she purred to him. “I’ll take what’s mine.

He complied immediately, without the slightest hint of resistance. He was back in bed, just as he’d begun but with a completely clear mind. He was also, once again, completely naked, although not as naked as he had thought he was when he first woke. June poked into the closet, just past his field of vision, although he could hear her rummage. She joined him in bed, setting herself up so that she could access his midsection. She gently spread his legs apart, and after a generous squeeze from a bottle she’d brought from the closet, she introduced a single finger into his backside. Gently working herself inside of him, sliding in and out slowly but steadily, she massaged his muscles into relaxing enough to welcome a second, well-lubricated finger.

As her fingers worked their way to his prostate, she positioned her other hand on the other side of his body. In her hand was a small device, pink and shaped like a large tadpole. The device sprang to life with the push of a button and vibrated quietly and—at first—gently. She slowly moved the vibrator from the tip of the cage down to the base, exploring one side of the shaft and then the other. Now it was Riley’s turn to grip the sheets and suppress a moan.

June knew he was hers to mold and manipulate. She could make him shake and quiver with a word, and she knew where every button was on his body. She took her time with him, slowing the vibrations down and then speeding them up, pressing his prostate down hard and then soft, flicking to tease and then taking him completely.

When she was ready, as she heard the word “please” escape from his clenched throat, she gave him everything. His body quaked, nearly shaking her off of him as he convulsed and his semen spurt from his cage over the sheets, off of the bed and onto the carpet.

And then his body collapsed, and he said to her, “Come here.”

They lay in each other’s arms, each feeling at once completely empty and completely full. June’s eyes fluttered as sleep threatened to befall her. She forced herself up to avoid passing out.

“Riley, we can’t both go back to sleep. You have work, and I have a report to complete. Besides, I already lost part of the morning to … oh … shit, that’s it!”

“What’s ‘it’?” Riley propped himself up, eager to hear what his fiancée had realized.

“That’s what happened today! I got up early to catch my friend Becky on Paris time.”

“Yeah?”

“And so I wasn’t there when you woke up! I always start the day by saying…” June turned to Riley and gently caressed his face with her hand, “Wake up, babe.”

That phrase. It was the most powerful trigger she had installed in him. It reset his mindset in a flash and brought his world into focus like prescription glasses. Like a switch, his muscles instantly relaxed, the fog lifted from his memory, and he knew who he was with fresh clarity.

He tilted his head towards his woman, caressed her face in return, and said to her in his softest, sweetest voice, “Good morning, babe. I’m here. Now, where are my clothes?”

reddit.com
u/Beautiful_Demand897 — 4 days ago

Wake Up, Babe [crossdressing] [oral] [plot twists]

Riley woke up in a haze to a half-empty bed. He had slept in later than usual. Not by a lot, but his morning routine had been fixed for so long that seeing the sun at a different point in the sky was disorienting by itself.

The extra space on the queen-size mattress also threw him off, but not as much as realizing that he was naked under the sheets. He couldn’t remember the last time he’d slept completely naked. But then, he also couldn’t remember much about the night before. He couldn’t quite put his finger on when he crawled into bed, what he was up to beforehand, and whether June was there at the time. It’s not that he always went to bed and woke up at the exact same time as his fiancée. But he usually knew when they were on different schedules, whether that was due to his work hours or her PhD studies.

The bedroom was silent except for the sounds that seeped in through the closed window and the door. Intermixed with the sounds of traffic from the street three floors below, Riley could just barely make out June’s muted voice. He couldn’t hear what she was saying, but her tone and cadence suggested a casual conversation with an acquaintance. There wasn’t a second voice, just gaps when June was silent. That suggested June was on a phone call, which led Riley to recall that her fellow PhD candidate and best friend Becky had gone to Paris for the summer. He calculated the time zone conversion from 7:30am in Portland to 4:30pmin Paris, and the sequence of events that led him to wake up later than usual to an empty bed suddenly fell into place.

He rolled out of bed, feeling an odd tingle up and down his legs as he did. He chalked it up to his bare skin sliding over their silk sheets without the usual intermediary of his flannel pajamas. Why his pants were missing remained a mystery. He planted his feet on the shag carpet of their bedroom and felt another odd sensation. This time, it was his calf muscles, which felt unexpectedly (almost painfully) stretched by lying flat on the ground. He’d woken up to a Charley horse in his legs before. This was not that. This was another morning mystery.

He opened the top drawer of his dresser and absent-mindedly pulled out the first pair of underwear with one hand while the other rubbed the sleep out of his eyes. He slipped his feet in one leg at a time, pulled the underwear into place, and switched drawers to grab a pair of socks. This time, he noticed that his hand landed on something unexpected. Where he expected to find a rolled-up pair of blue dress socks, his left hand instead grabbed a folded-up bunch of beige nylon. Not a pair of socks but pantyhose. He paused and scanned the rest of the drawer, only to find that it was filled almost entirely with hosiery—pantyhose, tights, and stockings. 

He was thrown by what he saw, but not quite because of what he saw. What threw him off is that it didn’t surprise him. He had the odd sensation that the drawer had exactly what it should, that whatever he used to find there—his dress socks, casual socks, and gym socks—had been moved. But he couldn’t recall where. We must have reorganized everything, he thought to himself. But when? Were we high? Did I get black-out drunk last night, right around the time we decided to switch dressers?

He didn’t feel hungover, and he didn’t see any empty bottles or roaches on the bedside tables.

Before he could test this theory further by checking June’s dresser on the other side of their bedroom, he felt a compulsion, an impulse. His left hand grabbed hold of the pantyhose and lifted them up from the drawer. The two legs unfurled before him, and he could tell immediately that these were not June’s. He hadn’t committed her size to memory, but he could tell that the legs were far too long for her 5’4” frame. When he held the dangling pair against his own waist, though, the length appeared to be just right. 

A word suddenly manifested in his head. It flashed like a theater marquee, like a billboard in his mind, and it wouldn’t go away.

“Mine.”

No, he thought, this isn’t mine. But that thought was overwhelmed by the sheer force of the insistent word.

“Mine.”

The word had a force that compelled his right hand to grab the opposite end of the waistband and compelled his feet to shift over to the empty bed. He sat down, feeling almost like his muscles and joints were on rails. The movements of his hands were mindless, driven by pure muscle memory like tying his shoelaces or signing his name. 

His hands rolled up one leg of the pantyhose until he reached the reinforced toe. Then his leg rose to position for his foot to enter and be encased. He could only pause the motion of his body through conscious will. 

It wasn’t the first time he’d put on a pair of hosiery like this. He’d tried it once in high school, acting on a dare from his girlfriend for her amusement. He was clumsy and yanked them up like gym socks, tearing a run from top to bottom that made her girlfriend howl and hit him in a fake rage.

This time, his hands weren’t clumsy. They were delicate and intentional. The instant he stopped willing his hands to stop, they continued to roll the first leg up, gliding over his smooth, hairless leg, before moving to the second and repeating the process.

Smooth. Hairless. Legs. Another mystery!

In a flash, the hose were rolled up to his thighs, and without thinking, he stood up to pull the waistband over his underwear. It happened so fast and effortlessly that he barely had time to process his latest discovery. That’s why the sheets felt different, he realized. 

He sat back down and ran his hands up and down over his nylon-encased legs as he tried to pinpoint exactly when and why he (or someone else?) had shaved his legs. The feeling was electric. He couldn’t recall anything like it. Every nerve ending from his hip to his ankle responded to his hands rubbing over them, coming alive to their touch.

He was addicted immediately. He couldn’t stop sliding his hands up and down and back again. The sensation captured him so much that he didn’t hear June’s cadence switch. He didn’t notice that her conversation was winding down. He didn’t catch the footfalls or the sound of her hand on the bedroom doorknob.

“Hey, babe!” 

June froze at the doorstep and locked eyes on Riley, who looked up at her like a deer right before a collision.

“Hi!” His voice snapped out of him like a triggered mousetrap.

She studied his eyes and his pose, his two hands frozen above his left knee. 

“Everything okay?”

He didn’t know how to answer. One part of his brain wanted to say that nothing about the morning had been “okay.” That voice was overruled by the rest of his brain, which—much to his surprise and confusion—felt very much “okay” with the situation despite it all.

He settled on a response that felt objectively true, even if his mind debated exactly why it was so: “I’m sure this looks strange.” 

June nodded with a smirk. “Yeah, you could say that.”

“I found, um, this,” he said with his hands open to display his legs, “in my dresser, and it just sort of happened.”

“Yeah, okay,” she replied flatly, leaving Riley to wonder if she even noticed that her fiancé was sitting on their bed wearing nothing but a pair of pantyhose over shaved legs.

“It just felt…” He paused to consider the right word. Like the word “Mine”, one word quickly manifested itself and took over his brain. “Natural. It felt natural.”

“Well …,” June said and paused, causing a sudden panic in Riley that she might say nothing more but instead just pack up and leave him. But her pause was brief, and the next word that came out of her mouth was a softly spoken “yeah.”

“Yeah?”, he asked, more baffled than relieved by her answer and her tone.

He could see her processing. He’d seen that furrowed brow on her face plenty of times before, usually hovering over a keyboard or a table full of notes and research. It was the focused intensity of her PhD-powered brain working something out. 

Her face and voice shifted to a tenor he’d seen come out of her whenever she had to teach an undergraduate course or mentor a younger student. She sat down next to him, laid a hand on his nylon-encased thigh, looked into his eyes with cool confidence, and said, “Tell me what’s been happening.”

“Well…” Riley walked through the last half hour of the morning, beat by beat. He spoke with the anxious precision of a student in the principal’s office. He didn’t think he’d done anything wrong. Not exactly. But he didn’t understand what was happening, and so his guard was up. “And then you came in.”

“Does anything else feel odd or unusual this morning?”

Now it was his turn to furrow his brow. That question implied that what he’d just described—waking up naked with short-term amnesia and crossdressing on autopilot—wasn’t enough.  That all of that might just be the tip of some even crazier iceberg he had yet to hit.

“I guess that my ankles also feel weird. I think I just slept on them wrong.”

“Like a cramp? A Charley horse?”

“Like that, but also no, not like that. My calves just feel tense.”

“All the time?

“When I stand up.”

“Show me.”

Now, Riley felt like a laboratory test subject. He suddenly stopped seeing June as his fiancée and started to see her as a lab technician. He stood up as requested and planted his feet flat on the ground.

June looked down with interest, looked back up at Riley, shrugged, and said, “Well, sure.”

“Sure, what!??” The more June seemed nonplussed, the more confused he grew.

“That’s going to happen to your legs after—wait just a second…” June abruptly shifted gears mid-sentence, suddenly stood up, and walked down the hall. Riley’s mind felt unmoored to a brand-new degree. He could feel reality shifting around him, and he began to wonder if he even knew where he was, or if he had maybe slipped into an alternate universe.

June returned to the room holding a pair of blue closed-toe block heels. She set them down in front of Riley, with the heels facing him and the toes facing away. She held out her hands to present them to him as if no further explanation was needed.

“You want me to—” She immediately nodded in response, with her eyes opened wide as if the answer was obvious. He performatively popped his eyebrow and vocalized a sigh as if to say, Well, why not? The day’s been weird enough already, so might as well keep going.

His feet slipped easily into the shoes. The size was just right, and the insides had noticeably molded to the specific shape of his feet. The lift of the heels took away the discomfort in his calves, and to his surprise, he felt perfectly balanced and (that word again) natural.

“Better?”

“Yeah.” He was genuinely surprised, but again, mostly by how little surprised the better part of his body and mind felt.

“When you’re in heels most of the time, the calves start to adjust until standing and walking without heels will actually feel uncomfortable.”

Her explanation made perfect sense. And yet, simultaneously, he felt like a bomb had just exploded in the room.

“Most of the time!?”

June’s eyes opened wide, and she mouthed a silent “Wow!” Her brow furrowed again as her mind returned to processing mode. She disappeared from the room briefly to grab a notepad and pen from the study room next door.

“Okay, sit down. We need to dig into this.” Riley did as she asked, sitting next to her on the bed as she scribbled into her notepad. He was equal parts nervous and excited, feeding off of the buzz radiating all around her.

“So,” she said with the tone of a Special Announcement, “we’ve been engaged in an experiment. You and I. With your full consent, I have been practicing hypnosis on you as research for my thesis.”

“Um, okay.” Every word she spoke had a ring of truth to it, but nothing she said conjured any specific memories in his head. She must have sensed his reservation because she disappeared again into the other room to grab an iPad.

“Here,” she said, pulling up a video on the tablet. The video showed Riley and June sitting next to each other at their dining room table (the iPad must have been propped up on the other side of the table). 

In the video, June looked back and forth from Riley to the camera as she spoke. 

“So, Riley Johnson, do you understand the project as I’ve described it, can you summarize it for us, and do I have your full consent, confirmed this Tuesday, January 5, 2022, at 4:35pm, in Portland, Oregon?”

Video Riley burst out laughing along with June. He also darted his eyes back and forth between her and the camera and replied, “Yes, I, Riley Milhouse Johnson, do hereby consent, fully… mind, body, and soul… to participate in a hypnosis experiment to switch my entire wardrobe from masculine, um…”

“Masculine-presenting,” June completed for him.

“Masculine-presenting,” Riley continued, “to feminine-presenting. The goal and purpose will be to change my perception of these clothes—”

“And your related behavior,” June added.

“—and my behavior to the point that I do not recognize that a change has occurred, but I will be going into this project with full knowledge and awareness, with consent to alter my perception, and waiving any liability that I may have against you, my soon-to-be wife—”

“—okay, stop, stop!”

The couple in the video laughed, and a moment later the video stopped. Riley stared at the paused image of himself and his fiancée, laughing and wrestling. Then he looked down again at his shaved and shimmering legs.

“Okay,” he said with acceptance. “So, okay. Here we are. So, was my amnesia or whatever it was this morning… was that also part of the process? Is that how I wake up every morning?”

“No, not at all,” June said, with a hint of concern in her voice. “I don’t understand why that happened. This is the first time you’ve had any kind of memory loss, and we’re a couple of months into the process.”

Riley’s eyes widened. He thought back and tried to recall how the last couple of months had gone. He could remember sporadic moments of their lives, working remotely, going to dinner, seeing friends… but every memory was foggy and the specific details felt just out of reach. When he tried to recall exactly what he was doing at any given time, how he felt, or what he was wearing, the moment slipped through his mind.

“So, have I been going out like this?  On Zoom calls? Out with friends or shopping?”

“You’ve been, well, the term is ‘underdressing’ whenever we’re out in public or you’re live on camera. That means you’ve had, you know, your old boy clothes on. But underneath it’s been—”

“This,” Riley finished.

June shrugged and smiled.

“I think I’d remember shaving my legs, though,” he said, poking at the story and also testing his own choppy memory.

“How much do you remember shaving? I mean, in general, not just recently?”

“Well, I know I shave my face. About once or twice a week.” He raised his hand to feel his cheek, noticing as he did that his nails were smoothly filed and painted teal.

“But if you think about shaving, do you remember specifics, like exactly when you shaved, for how long, what time of day?”

He studied his hands as he pondered her question. “I guess I don’t. I just have the vague recollection that it’s something I regularly do. Just like, um…”

“Just like caring for your nails,” she offered.

“Yeah.”

June reached out to hold his right hand with her own well-manicured hands and looked softly into his eyes. “You were changing your routine in ways you didn’t really notice. It folded into the background of your day-to-day routine. It was like washing your hands or folding laundry. Shaving your legs and painting your nails became routine, something you wouldn’t even notice or bother remembering.”

Riley considered everything she said. It all made intuitive sense, and yet it still felt like something was missing. They were still left with the mystery of why this morning was different.

“Maybe you can tell me more about how this works, then. I mean, you’ve told me about clinical hypnosis for therapeutic purposes before. But I’ve never seen you do it.” He realized how funny that was for him to say, since he’d obviously been seeing it first-hand for months now. They gave each other a knowing look and laughed.

“Yeah, so, it’s a combination of things,” June said, amused at the novelty of explaining to her fiancé-slash-patient the very thing he’s been witnessing her do for so long now. “We’ve had regular sessions, which take about 30-60 minutes of continuous hypnotic treatment. Out of that process, you’ve developed a few triggers. Some of them are conscious, some are unconscious. It’s mostly a matter of repeating patterns and keeping things consistent. Positive reinforcement, small rewards here and there. Eventually, though, I needed to reinforce your triggers less and less, and all of the reinforced behaviors faded from your conscious mind and became part of your natural perspective.”

That word again. Natural.

“So, what are the triggers?”

“Some triggers are words or phrases. Some are not. Like—” June demonstrated by casually lifting the pointer finger of her right hand towards Riley. Her finger softly landed on his right shoulder and slid down to his nipple. Then she repeated the motion on the other side of his body, starting again from his left shoulder down to the other nipple.

Riley’s eyes twitched immediately, and in a nearly involuntary reaction, his arms crisscrossed over his body.

“How do you feel?”, June asked clinically.

“I feel naked,” he answered immediately.

“Well, you are naked. Do you feel more naked now than you were a moment ago?”

“I feel…” A word popped into his mind. He struggled to find another word, but he realized that it was the only word that felt right. “Topless.”

“Well, you can fix that,” June suggested, nodding her head towards his dresser.

Riley nodded and walked over to pull open the third drawer from the top. Inside, he saw a row of shirts. He grabbed the first one he saw, a grey V-neck undershirt, and he slipped it on. The soft fabric felt comfortable but also somehow incomplete.

“How do you feel now?”

Riley thought about it. He listened to his body. He gave the only answer he could. “I feel less naked, but I don’t feel … dressed.”

“What would make you feel dressed?” Her questions were clearly leading him, and he knew it. But he also felt in his bones that she was asking him the right questions, and each question only had one right answer.

He pulled off the shirt, dropped it to the ground, and turned back to the dresser to close the third drawer and open the fourth. In that drawer, he found exactly what he expected to find. He pulled out a pink, wireless, soft-cup bra and slipped it over his arms. As he did, the word “Mine!” screamed again in his brain. His hands met behind his back, and with ease, his fingers grabbed the two back-ends of the bra and clipped the hooks into place. Switching back from the fourth drawer to the third drawer, he pulled out a silk blouse patterned with blue and white stripes. He slipped it on, and it fell naturally on top of his bra, the A-cups giving subtle curves to his otherwise flat torso.

“And now?” June asked.

“Now, I feel dressed. Well, half-dressed,” he said, looking down at his legs and giving them both a laugh. “Tights may be pants but—”

“No, pantyhose definitely are not,” June agreed and laughed again. 

She smiled softly at her half-naked fiancé and nodded towards their bedroom closet door. Riley walked over to the closet, feeling again like he was on rails as he opened the door, reached directly for a particular hanger in the middle of the closet, and removed a sky-blue pleated midi skirt. With deft motions, he held the waistband of the skirt with both hands while he stepped gingerly into the garment. He remained perfectly balanced on one leg and then the other, and when he was done, the outfit was complete.

Riley closed the closet door and gave himself a good look in the full-length mirror on the other side. Every article fit his body and even complemented his body shape. It was jarring seeing himself like that but also—again, that word returned to his mind—"natural.”

“I take it we weren’t going for ‘drag queen.’”

“No, not at all. Your style has been very conservative, perfectly office appropriate.”

“Okay, so…” He thought carefully about the question rolling around in his head. “What was the goal exactly?”

June blushed. It was the first time that morning he’d seen her react that way. Until then, she hadn’t been even the slightest bit shy seeing her man in full women’s garb. What had suddenly made her so nervous?

“Do you want me to become a woman?” Everything up to that point had felt in some way normal to Riley, despite it all. But that question felt like he had taken a step off the rails.

“Oh no,” she replied right away, “I mean, if you were trans, we could figure that out. I’d support you. We’d make it work. But we always knew you were cis, straight and all that.”

“Okay, right,” he said, agreeing with her and believing everything she said. “Was this just to see if you could do it, for the sake of your PhD thesis?”

“It’s … yeah, the thesis concerns fluid gender identities and whether we can break down barriers between the sexes. Is there anything intrinsically quote-unquote male about pants and quote-unquote female about a skirt, for example? And why shouldn’t a man wear a bra if it makes him comfortable and accentuates his body’s curves? And—”

“Why me, though?” Riley could tell she was avoiding something. He knew her every verbal tick and tell.

Her cheeks blushed even harder and she turned her eyes down. Slowly, carefully, she said, “You had your own motives.”

Riley tilted his head toward her and held out his hand in an open gesture.

“You had this hang up…”

And suddenly, he knew exactly what she meant. “Oh.”

“Yeah, so, you were always nervous about, you know—”

“Going down on you.”

She nodded, her cheeks still red. “We unpacked that, you know. Your hyper-masculine dad and your brothers, the frat atmosphere, the—let’s just say it—toxic swirl of homophobia and misogyny you grew up surrounded by. Telling you that going down on someone, even a guy going down on a girl was…”

“Effeminate.” Riley completed her thought, nodding as another piece fell into place.

“We figured, since I was looking for a test subject anyways—”

“We figured, let’s see if giving me a new perspective on gender helped to strip away my apprehensions.”

June nodded enthusiastically, and another portion of Riley’s memory came back into focus. “And it worked,” he said, and June nodded even harder and faster. “Well,” he added with a Cheshire Cat smile, “let’s not interrupt the experiment in that case.”

June’s face beamed, switching in a heartbeat from self-conscious to ecstatic. Riley moved over to where she sat on the bed and, with the pointer finger of his right hand, pushed her gently backward onto the bed. He dropped to his knees, nudged each of her legs apart from the other, and unzipped the zipper of her grey dress pants. With his fingers looped into the belt loops, he pulled her pants down to her ankles. He did the same with her yellow panties, so that her ankles met and her legs bent to form a rectangle.

Riley leaned into the space between her thighs and discovered that his hang-ups around cunnilingus had been purged entirely from his mind. He dove in without hesitation, letting his tongue explore every fold of her. He could feel her muscles tense and her body writhe. He could tell her hands were gripping the sheets and her teeth were biting her bottom lip. His mouth settled on top of her clit, which was like a small, engorged pebble, slick and covered in the mixture of her fluids and his saliva. He alternated between sucking and licking, letting her fill his mouth with her sweetness, swallowing some of her and letting the rest spill back out as lubricant.

He remembered an old trick he’d heard once, to spell words with his tongue over her clit and labia. The trick served him well. After spelling her name and then his, the words that continued to pop into his mind made it out of his mouth and onto her body: “Mine.” “Natural.”

On the last letter of the last word, her body finally surged. Every muscle in her body seemed to contract and spasm at once and in waves. Her mouth opened, her teeth releasing her lips and letting out a scream that must have been heard two floors in either direction from their apartment. And then her body collapsed.

“Get up here,” she managed to say between panting breaths. He obliged, climbing up to meet her face. With the last of her strength, she lifted herself enough to meet his lips, kissing and lapping up the remnants of her around his mouth. “You must be ready for a go yourself.” 

She wasn’t wrong, but he suddenly noticed that something felt different. His blood had risen along with his passions. He wanted—he needed a release. And yet, something felt different. It felt (yes, again) natural, and yet, still, different.

Riley stood up over her and, unsure as to what felt different, tried to deflect.

“I can give you a striptease, but it might be funny when I go from all of this down to my plain old boxer briefs.”

June, still panting, tilted his head and looked up at him with a peculiar expression. Unsure of what he meant, she circled her fingers in the air in a wordless gesture of “let’s go, get on with it!”

Now it was Riley’s turn to blush. He couldn’t explain it, but something between his legs felt off. He worried that, in all of the hypnotic shenanigans, maybe his libido had been impacted. He pulled off his blouse, slid his skirt down to the ground, stepped out of his heels, and pulled his pantyhose off one leg at a time.

And there he stood, down to his underwear. Pink panties that matched his pink bra.

“Riley, those aren’t boxers.”

“No, they aren’t!” he yelped in genuine surprise.  He hadn’t even looked in the drawer when he had pulled them out and slipped them on. He was on autopilot the entire time.

“You didn’t notice when you put them on?”

“I didn’t, I just assumed they were—”

“Did you think, ‘Mine?’” The word sent a shiver down his body. “Did you think it was ‘natural’?” His body shivered again.

“Oh, my god.” His entire body tingled. He felt light as a feather. He felt jolts of electricity running throughout his body in every direction.

“Did you even notice…?” June trailed off and gestured with her right hand toward the mound in his panties.

He brought a hand down on top of it and felt, for the first time, that his member was encased within a plastic sheath and that sheath had a ring that went around the base of his genitals. He was wearing a chastity cage, and he didn’t even realize it.

“Natural,” June said again, causing his testicles to contract and his penis to press desperately against the downward pressing sheath. She lifted her head up and propped herself up by her elbows. “You thought it would help with remolding your mindset. But don’t worry, we have ways of relieving you.”

Sitting up so her head was level with his hips, she pulled his panties down to the ground and exposed the black cage. With one hand, she grabbed his balls and gently rolled them around in her fingers while he moaned.

“Now, lie down on your back,” she purred to him. “I’ll take what’s mine.

He complied immediately, without the slightest hint of resistance. He was back in bed, just as he’d begun but with a completely clear mind. He was also, once again, completely naked, although not as naked as he had thought he was when he first woke. June poked into the closet, just past his field of vision, although he could hear her rummage. She joined him in bed, setting herself up so that she could access his midsection. She gently spread his legs apart, and after a generous squeeze from a bottle she’d brought from the closet, she introduced a single finger into his backside. Gently working herself inside of him, sliding in and out slowly but steadily, she massaged his muscles into relaxing enough to welcome a second, well-lubricated finger.

As her fingers worked their way to his prostate, she positioned her other hand on the other side of his body. In her hand was a small device, pink and shaped like a large tadpole. The device sprang to life with the push of a button and vibrated quietly and—at first—gently. She slowly moved the vibrator from the tip of the cage down to the base, exploring one side of the shaft and then the other. Now it was Riley’s turn to grip the sheets and suppress a moan.

June knew he was hers to mold and manipulate. She could make him shake and quiver with a word, and she knew where every button was on his body. She took her time with him, slowing the vibrations down and then speeding them up, pressing his prostate down hard and then soft, flicking to tease and then taking him completely.

When she was ready, as she heard the word “please” escape from his clenched throat, she gave him everything. His body quaked, nearly shaking her off of him as he convulsed and his semen spurt from his cage over the sheets, off of the bed and onto the carpet.

And then his body collapsed, and he said to her, “Come here.”

They lay in each other’s arms, each feeling at once completely empty and completely full. June’s eyes fluttered as sleep threatened to befall her. She forced herself up to avoid passing out.

“Riley, we can’t both go back to sleep. You have work, and I have a report to complete. Besides, I already lost part of the morning to … oh … shit, that’s it!”

“What’s ‘it’?” Riley propped himself up, eager to hear what his fiancée had realized.

“That’s what happened today! I got up early to catch my friend Becky on Paris time.”

“Yeah?”

“And so I wasn’t there when you woke up! I always start the day by saying…” June turned to Riley and gently caressed his face with her hand, “Wake up, babe.”

That phrase. It was the most powerful trigger she had installed in him. It reset his mindset in a flash and brought his world into focus like prescription glasses. Like a switch, his muscles instantly relaxed, the fog lifted from his memory, and he knew who he was with fresh clarity.

He tilted his head towards his woman, caressed her face in return, and said to her in his softest, sweetest voice, “Good morning, babe. I’m here. Now, where are my clothes?”

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u/Beautiful_Demand897 — 5 days ago