r/cdstoriesgonewild

So this happened when I was 24. By this time I was already well versed in sissyhood.

I had a collection of outfits, lingerie, wigs. I kept my body shaved when I was able to (mainly in the colder months since I would wear pants more often in my day to day).

While my normal weekdays didn't deviate from my life too bad (mainly some minor dressing and teasing online). The weekends were my playtime.

Normally Friday after work I would go home, get changed into a cute outfit I picked out the night before and spend time solo.

Saturdays were the days I went out. Sometimes it was to a CD friendly gay bar. Those nights normally ended in me blowing a guy in his car or being bent over his truck. Sometimes I went to an ABS after hours. More than a few times I would spend the day on Grindr to arrange some nighttime fun.

There I was still sitting in my boy clothes at like 2pm. Just checking out my profile, seeing who was looking good. Eventually I get chatting with a nice looking guy. Early 40s, BWC (least 7 inches), hairy and tall (I average around 5 '7 in flats, 5' 10 in heels) he was at least 6 '2. (He will be referred to as James going forward)

We start chatting, im being playful by sending him photos and a little teasing. He responds by saying he wants to meet at his place later that night. I agree and show him a few outfits and ask what he wants me to wear. I believe it was between a school girl outfit (blouse, skirt, stockings,heels) a housewife getup ( 50s style dress, leggings, a little more makeup) or a “slut” outfit (miniskirt, fishnets, pumps). He ask for the housewife (my personal favorite). He send me his address (about 15 min away) and we set the arrival for a little after dark around 830.

I start getting everything ready around 6pm. Gives me 2 hours to get decent. I just hop out of the bath when I see a message from James. Asking me if I mind a change. He was going to have a buddy stop by for a bit tonight. His buddy, and him, are on the DL ( I learned after arriving that he was MARRIED with KIDS). He said we can reschedule OR when he arrives I can sneak off to another room since it will only be a few minutes. At this point Im already prepping and horny that I dont want cancel. I agree to hide, IF he knows what time he was going to arrive. He said he was going to arrive around 9 so we will pause then.

Perfect!

By the time I finish everything, I am sliding on my black heels and fixed a perfect red head wig (think a MUCH SMALLER version of PAM from Married with Children). Even added a little bandana to complete the illusion. I wrap a coat around myself and get into my car.

I arrive at a nice little suburban house and I see porch lights. It's 8: 30 and I text him saying I'm outside. He said the door is unlocked to just come in. So after taking a deep breath I walk up and open the door.

THE FUN:

I get there and he greets me at the door. He says I look lovely and I do a little spin and a curtsey.

I put my purse down (filled with lube and condoms in case he wasn't clean) and came over to him. I put my arms around him. Telling him it feels good to come home to a big strong man.

He offers me some wine and I sit on the couch in my best “knees together good girl” position. After taking a few sips I ask him what he wants to do?

He leans over and starts making out on top of me and I am just going with it. I feel him grope my breast (padding) as my hands slowly make thier way down his pants.

Eventually I get to the bulge and it feels so HUGE!. I ask if he wants me to take care of this? He backs off a bit and undoes his belt. I slide to my knees and fish out one of the biggest WHITE dicks ive seen. I make sure my hair isnt in the way. Give it few tugs and a lick for good measure. I do my best to take it as deep as possible and I see his head lean back and his hand goes on my head. I take that as my sign he likes it.

I am about 10 min in and was gonna end it soon (i came for this in my ass) then…We both shoot up as we hear the door. We lost track of time and when we looked at the clock it was 9:10. In walks his buddy (“Mark)”. About as tall as him, little darker skin, not bad looking.

He came in saying “Hey man, sorry im late, I just wanted to see if you had…” There was at leas 15 seconds of silence as I sit there with James’ cock in my hand. He starts laughing asking if he was interrupting. James plays it off saying that I was just a sissy (clearly not his first). Then he does something that would normally be a turn off, but I went with it.

“ You want a go at her?”

There he was, a man I just met offering me up. I should of been mad…but I was just turned on. I let go of James and put my knees together and in my best femme voice “Id be happy to help you”

Mark gets over to me and slides his pants down. His cock is roughly the same size of James and,unlike him, not as gentle. As soon as the pants are off he guides me to his cock and I swallow it like I'm expected to. I spend a good 5 mins getting throat fucked, All while James is jacking off.

James gets up and starts pawing my ass a bit. I extend it out to let him and he ask if im ok with sharing. I nod and Mark lets me breath.

I get my arms up on the couch and extend my ass. I tell them there is lube in my purse. Before I know it, the shirts are off and I have 2 naked men in front of me. James lubes himself and is generous. I slide off my black thong and he applies it to me. At this point I'm all in “Yes daddy, I need your married cock inside me!”

Suddenly he enters me and after a few seconds to adjust, starts going hard. I start moaning, all while my cage is clicking against me. Mark gets on the couch and places his dick right in front of me. I go off instinct and take it.

“Let me see those titties!” He undoes the buttons on the top of my dress to expose my bra, rips of my bandana on my hair, all while I'm getting railed.

I'm lost the moment I don't look at his face. I did not see him take his phone out. He starts recording it.

They are both laughing, im getting some light smacks on my ass and face and start talking dirty.

“Whos our good little girl?” “I am! I am daddy, fuck your little girl!!!”

They both pull out and guide me back on my knees. THey start jerking it in front of me and I know what to do. I open my mouth and start begging for it. Before I know it 2 hot loads of thick cum are draping down my face and clothes.

When they finish I jerk them both a bit for good measure as they sit on the couch. After a little rest, I get my shoes, bandana and purse. I tell them I need my beauty sleep and I had a lot of fun. James gets up and walks me to the door. He said he feels stupid for not checking the time. I tell him it was fine and I had fun. Mark ask if he can have my number for the future. I agree and sign it Jenny with a little heart.

I tell them both I had fun and would love to repeat this.

I button my top up a bit and walk to my car.

When I get home I basically pass out as soon I get to my bed, still in my dress covered in cum.

Only after did I remember the video. I decide its not worth making a snuff over since no one knows who I am. But its probably still out there. Maybe online? Shared between his friends? I never did see them again so who knows.

Fun to think one day my wife (married years later) may find it lol

Tom had spent the last three weeks observing Randy with a predatory, calculating hunger. From behind the mahogany desk of his executive office, he watched the way the young man moved, the slight, tentative sway of his hips, the way his oversized dress shirts draped over a frame that was delicately thin, and those wide, twinkling blue eyes that radiated a naive innocence. Randy was a masterpiece waiting to be sculpted. At twenty-two, with a waist that looked like Tom could snap it with one hand and a cute, pert little butt that strained against his slacks, Randy was the perfect candidate for Tom’s specific brand of domestic molding.

The business trip to Chicago was the perfect catalyst. While Randy had been preoccupied with finalizing the presentation slides, Tom had executed a silent, surgical strike. He had swapped Randy’s modest suitcase for an identical one, meticulously packed with silk slips, lace panties, tight skirts, and sheer stockings. Tom didn't just want a quick fuck; he wanted to cultivate something deeper. He wanted to break the shell of Randy's masculinity and reveal the submissive, feminine creature he knew was hiding underneath, molding him into a devoted boy-wife who belonged solely to him.

The tension reached a breaking point the moment they entered their hotel suite. Randy dropped his bag on the plush carpet, glancing around the room. His blue eyes widened as he realized there was only one king-sized bed, the linens crisp and white, dominating the space.

"One bed, Mr. Sterling?" Randy asked, his voice soft and trembling slightly. "I... I thought there would be two."

Tom didn't answer immediately. He shed his suit jacket, revealing the muscular breadth of his shoulders and the power in his chest, filling the room with a heavy, masculine presence. He leaned against the dresser, a small, enigmatic smile playing on his lips as he watched Randy unzip the suitcase.

The silence that followed was deafening. Randy stared down at the contents of the bag—a flurry of pinks, creams, and black lace. He reached in, pulling out a sheer, floral-patterned dress and a pair of thigh-high stockings. His face flushed a deep crimson, his breath hitching in his throat. He looked small, vulnerable, and utterly confused.

"What... what is this? My clothes... they're gone," Randy whispered, clutching the silk fabric to his chest, his voice bordering on panic.

Tom stepped closer, his expression shifting into one of faux concern, though his eyes remained sharp and hungry. He didn't seize control with a command; instead, he played the part of the helpful mentor.

"What on earth?" Tom murmured, leaning over to peer into the bag. He let out a soft, theatrical sigh. "Good god, Randy. It looks like there's been a massive mix-up at the luggage handling or perhaps with the bags. This is completely wrong."

Randy looked up, his blue eyes shimmering with uncertainty. "I don't understand. How could this happen?"

Tom reached out, his large hand gently brushing against Randy’s shoulder, a touch that felt supportive yet possessive. "It's a nightmare, truly. But we're in the heart of the city and it's late. Getting a replacement suitcase or finding a store open now is out of the question. We have a meeting tomorrow morning, and we can't have you appearing unprofessional."

He paused, his gaze drifting down to Randy’s slender waist and the soft curve of his hips. "Look at you, Randy. You're so slight... honestly, some of these pieces might actually fit you. It's absurd, I know, but until we can sort this out tomorrow, you'll have to make do."

Randy shivered, a strange, electric thrill racing down his spine. He should have been outraged, should have demanded a solution, but the way Tom was looking at him—with a mixture of pity and a hidden, simmering heat—was intoxicating. He felt a hidden part of himself, a side he had never dared to acknowledge, stirring in response to the suggestion.

"I can't... I can't wear these," Randy whimpered, though he didn't pull away from Tom's touch.

"It's just for tonight and tomorrow morning, Randy. A temporary necessity," Tom countered, his voice a low, soothing rumble that brooked no real argument. "Besides, you have a softness to you, a delicacy that might actually suit these fabrics. Why don't you try that slip on? Just to see if it works. I'll help you figure out what's wearable."

Tom stepped back, crossing his arms over his chest, his eyes scanning Randy’s skinny frame with an appetite that made the boy’s knees weak. "Go on. Strip down. Let's see what we can make work with this 'mistake'."

Trembling, Randy’s fingers went to the buttons of his shirt. He felt exposed, his heart hammering against his ribs like a trapped bird, but as he peeled away his masculine facade, he found himself glancing at Tom, desperate for the approval of the man who was slowly, carefully claiming him.

Hi everyone. I've shared a couple of my first time stories here before about my sexual awakenings when I was younger. You can read them on my profile. Here is one about my first time going through with actually taking a cock in my mouth. Hope you enjoy it!

This was a few weeks after I first experienced a porn theater at my local porn shop. My head was still wrapping around the memories of that day. The thrill of being lingerie clad, and exposed in the theater while two guys jerked and came on me like their personal cumrag, was amazing. It was so much masturbatory material that I hadn't even looked at porn for a couple of weeks.

I was home alone again on a Saturday night, still living with my parents in my early 20s. They had left for the night for a party and I had the house to myself, so naturally I threw on my lingerie as I always did and hit the interwebs. Exhausting the available porn sites as usual, without anything getting me off, I started fantasizing about the theater again, and how I wished I had gone further. I decided to hop on the yahoo chat room again and see if there was anyone local, or even if Bill was there.

After lurking a bit, a conversation was started by a man, I'll call Luke. He was looking for someone into wearing panties and looking to be his little cum slut. He was 47, over twice my age, and hosting.

I dwelled on it for a second and grabbed a bottle of vodka, and downed a couple of shots quickly, before replying. I said, "I know I could sure use a nice load on my face!"

He private messaged me not even 10seconds later.

"Hi there, my little cumslut. Where are you located," he asked.

I responded by telling him my rough location in South Bend, Indiana. Telling him I'm not able to host, but willing to come to him if he was willing to cum on me.

"Sounds perfect," he said. "How soon can you get here? I live about 5 minutes there."

"I just need to throw some clothes on over my naughties and I can be there in about 10 mins." I typed furiously.

He sent me the address and told me to come in the side door. I threw a zip up hoodie on and some sweatpants, grabbed my keys and bolted to the car. The vodka was just hitting my mind when I pulled onto his street. I parked a few houses down from his place, so that he couldn't see the car I was driving. Although it was late November and dark out already. I walked through the cold night air to his driveway and found the side door he asked me to go to.

As I approached the door he was already waiting inside. He open the screen door and invited me in.

As I walked into the kitchen, I saw a 47 year old daddy type. Dad bod, nothing spectacular, standing there in boxer briefs and nothing else. There was an outline of a huge cock in the underwear. I mean FUCKING HUGE! It was point up and almost around his left hip.

"Are you ready for this, my little cumslut," he asked, as he pulled his boxers down and let his hard massive member fold and flop out.

I didn't say a word or nod as I saw his, what had to have been 8" or bigger cock, fall out of his underwear. I immediately took my hoodie off exposing my black satin bra. I then turned around and bent over as I pulled my sweatpants down, exposing my black satin panty clad ass and fishnet stockings to his monster rod. I hadn't noticed that my own cock was falling out of my panties until I turned to face him. I noticed he saw it, and I looked down to tuck it back into my panties.

"Sorry about that, I said."

"No big deal. I didn't expect a real woman, when I asked you over, he said, as he walked toward me. He placed his hands on my shoulders and guided me down to my knees, where the head of his cock rested hanging down towards my chest.

I grabbed the long meaty shaft and pulled it upright towards me face so I could gaze and look upon it with marvel. I placed my right hand under he swollen cumsac and started stroking the shaft slowly with my left hand. He moaned with delight as I stroked and stroked.

"Spit on it, make it nice and wet babe," he demanded.

I conjured up a nice dollop of spit and drooled it out onto his shaft as I jerked. I then began jerking it with both hands as there was so much real estate to work with. As I jerked him with both hands I began pulling him closer to me, the head of his cock inching closer to my face with everyone pull and tug. It was within inches of my mouth and at this point I couldn't take it anymore. I opened my mouth and guided the swollen, pulsating head in between my drooling wet lips, and closed them around it. I moved it further into my mouth, feeling the head glide along my moistened saliva covered tongue, until it reached my uvula. I rested it in my mouth for a few seconds as my hands jerked every inch of the exposed shaft. I then felt and tasted my first taste of precum. I knew he was enjoying himself and getting closer.

As I continued to suck his head while jerking the shaft,Luke began thrusting in and out of my mouth. Pulling out just enough to pull strands of saliva out with the shaft, before sliding back into my gaping mouth. He had pushed a bit too far a couple of times, testing my gag reflex, which was not accustomed to a cock knocking on its door. I pulled back gasping for air, and spitting out a blob of saliva in the process, before grabbing his cock and engulfing it once more. I became ravenous for his cock. Furiously jerking and sucking it, now.

He moaned again, "Here it cums baby! Take it all slut!"

I pulled it out just as he let out a loud groan, and his cock let loose a huge shot into my face, impacting on the left lens of my glasses. Another shot had grazed my cheek and went past my head hitting the refrigerator door behind me.Then next few shots landed firmly on my lips, and the power left the load. The final drop drizzled down onto my chest as the cum on my lips began to drip off my chin onto my knees.

After Luke caught his breath, he thanked me, and grabbed me a towel to clean up. "No thanks," I said. " I want to savor the his moment." I let the cumsicles fall onto my bra from my face and stood up. I put my sweatpants on and my hoodie. "Thank you so much, daddy." I turned to the door without saying another word as he slapped me on my ass. I opened the door and giggled as I walked back out into the crisp air and headed back to my car. This was not the last time I'd run into Luke, luckily. 😜

Hope you enjoyed this memory as much as I do. I'll hopefully have more to tell again soon. Thanks for reading.

So many of you ask me for the second part of my story from the other day so here it is hope you enjoy! 😊

For three months I tried to kill Becky.

After that first video call with Brandon I felt so much shame it scared me. I deleted the Snapchat. I stopped checking the crossdressing subreddits. I threw myself into work and into being the perfect boyfriend when my girlfriend got back from Europe. I told myself it was just a one-time thing, a weird phase, something that happened because I was home alone and he was being so nice. I even started feeling proud of myself for getting it under control.

Then one random Tuesday night I was scrolling Instagram and I saw her.

A girl in this beautiful white floral maxi dress. It was strapless and sleeveless, light fabric flowing down with delicate pink and yellow flowers, a high slit showing just enough leg. She looked so soft and feminine and free. Something in my chest cracked open so hard I actually put my phone down and walked away from it for a minute.

I lasted maybe twenty minutes.

I went back to my laptop and ordered the dress right then. It was going to arrive in a few days and my girlfriend was heading out of town that weekend to visit her old college roommate. I told myself I was only going to dress up for me. No reaching out to Brandon. This was just my private hobby again.

The next few days were a rollercoaster. I spent hours watching YouTube makeup tutorials, practicing looks, going back and forth between guilt and excitement. One minute I felt shameful for even thinking about it. The next I was imagining how the dress would feel on my skin. I kept telling myself it was okay. I was only going to dress up for myself this weekend. Nothing more.

Saturday morning my girlfriend left for her trip. The house was quiet again. As soon as her car pulled away I put on some Sabrina Carpenter and Ariana Grande, letting the music fill the rooms. I went into the bathroom and took a long shower, shaving every part of me that had grown out over the past three months. The warm water felt good on my skin. When I stepped out and dried off I felt smooth and sensitive all over.

I put my blonde wig on but tied it up because I love doing my makeup with the wig already on. I sat down at the vanity and started. The familiar scents of foundation and powder hit me. I blended the base until my skin looked flawless and glowy. I did soft smoky eyes that made them look bigger and more inviting. Rosy blush on my cheeks. Glossy pink lips that tasted sweet. Every brush stroke made me feel more feminine and pretty. For a second I thought about Brandon and the gift cards he had sent me before. No. This is just me and my hobby. That was just a weird little phase.

I took off my robe and put on a super soft light pink lace thong and matching bra. The lace felt delicate against my smooth skin. I felt so euphoric and sexy at this point but I decided not to look in the mirror until the full look was done.

I grabbed the new white floral maxi dress and white heels. I slipped the dress on. It felt incredible, the fabric cool and flowy against my legs, the way it hugged my waist and fell to the floor with that perfect slit. I stepped into the heels.

I finally walked in front of the full-length mirror.

The rush hit me all at once. Nervousness. Excitement. Joy. Shame. I looked like Becky again. Really like her. The dress made me feel graceful and pretty in a way nothing else did. My heart was pounding.

As soon as I saw myself something took over. I grabbed my phone, redownloaded Snapchat, added Brandon, and sent him a cute mirror photo.

Me: "Hey… it’s me. Becky. I’m really sorry I ghosted you. I got scared and tried to put this away for a while. I feel so confused and ashamed but I also really miss this. I’m sorry."

Twenty minutes went by while I did a little photo shoot in the dress, daydreaming about going out in public like this, maybe even with some other girls like me. Then my phone buzzed.

Brandon: "Hey princess. I was wondering when I’d hear from you again. You don’t have to apologize. I figured you needed some space. That picture you sent… damn. You look glowing and happy. How are you feeling right now?"

We ended up on a long video call. I told him everything. How hard I tried to stop. How guilty I felt. How much I loved feeling pretty like this. How right now I was daydreaming about going out of town as Becky in public with some other girls like me.

He was so encouraging. "It’s okay to be part-time, Becky. You don’t have to choose. Tell me more about that daydream. Where would you go? What would you wear?"

I opened up more. "It would be fun to go somewhere like Vegas. Get a nice hotel room at the Bellagio or the Cosmopolitan. Girls brunch, shopping, pool time, dinner, maybe dancing or a show. Just a girls weekend."

He kept asking questions, getting me to describe everything. For brunch I said I would wear something casual but feminine and flirty like a cute white top with a denim mini skirt and brown boots. For shopping the same flirty look. For the pool I would wear a pink bikini with a pink crochet cover-up, a big feminine white hat, and cute white cork wedges. For nighttime I had a hard time choosing between the black lace dress with puff sleeves and tights or the black lace jumpsuit.

He listened to every detail and gave his thoughts.

"That white floral maxi you have on right now would be perfect for a romantic dinner," he said. "I can see you walking into the restaurant looking so elegant. For the pool the pink cover-up would look adorable on you. And for nighttime… I love the black lace dress with the puff sleeves. You’d look so sexy and confident in that. Hair up, bold red lips. That’s the one I’d want to see you in when we go out dancing."

The conversation kept building, getting flirty. He told me how much he loved the thought of me dressed up like that. How it made sense because he wanted me to be his part-time little secret girlfriend. How he wanted me to embrace it.

Next thing I knew he video called me. He was in his bathroom, phone propped up, standing there in a towel after working out. He looked strong and handsome. He started convincing me how nice it is to just do what Daddy says. He made me pose for him, all fours looking back, on my knees looking up, cross-legged. He made me show him my feminine dancing moves. Then he told me to grab my dildo and put on something sexy.

I rushed off camera, took off the dress, and changed into the light pink see-through baby doll lingerie with the matching pink thong and bra. I kept on the white heels and touched up my makeup.

When I got back on camera I moved slow and feminine. It felt so good. He made me pose on the bed in different ways, asking me how good it felt to be this pretty, to be Daddy’s girl, how it felt having a man watching him stroke his big cock.

We went back and forth. It got hotter. He made me end up begging for him to come and be his girl.

After he came he told me not to. He wanted to pay for a trip to Vegas for me and two other online girlfriends of mine that are crossdressers. "Becky deserves to be seen."

I asked if he was serious.

He said yes. "How about these dates?"

I got nervous but said yes.
…

True story

Over the last three years I have had fun servicing a local coach from the high school. Usually we meet in his backyard shed and I suck his cock. I don’t know his name, but I know his cum is extremely creamy and I alway swallow his seed. I have let him fuck my pussy a few times and on some occasions, he has filled my cunt after my other friend has already been there. Recently, I contacted him for cock and he told me to meet him by the baseball field. I quickly got ready, put on my bra, shirt, plug, sandals and a skort I like. When I got to the field, he led me up the stairs to the press box. We went inside and it was a larger room with a couch at the back. I could look across to the football practice field and there was football practice going on. I don’t know if anyone could see us, but I pulled his coaches shorts down and began sucking his cock and balls. After a few minutes of that, his cock was erect and my pussy was throbbing, so I pulled my plug out, got on my knees on the coaches couch and he slid his hot, aching cock into my sloppy pussy. He had his hands on my hips and rode me for about 10 minutes. He moaned as he shot his load into my hot cunt. He rested on my back for a minute going soft. slowly, he pulled out of me, and I popped the plug back in. I then got on my knees and sucked the remaining seed off his dirty cock like the good little cock slut I am. Once he had used me, he had no further use for me and I went home. Once there, I pulled out my plug and lovingly tasted his creamy cum from the plug and from my fingers as it oozed out of my cunt while I rubbed myself all over remembering how sexy it was in the press box. I can’t wait for another trip to the press box.

Some background, I have been meeting this guy for a while probably 20+ over the past two years, I met him when I was 20 and he was 58 and he knows how to treat me like a real sissy 🫦

I parked a little down the street from daddy’s house just after 11:30, killed the engine, and slipped through the side gate like I had done every other time. The back door was already unlocked for me. Inside, the house was dark except for a faint strip of light coming from upstairs. On the kitchen counter sat the surprise he had left for me, a brand-new pair of sheer black fishnets still folded neatly and some suspenders.

I kicked off my shorts right there on the tiles, peeled down my panties just enough to step out of them, and worked the fishnets up my legs. The tight nylon hugged every inch, the diamond pattern stretching across my ass and framing my cock in the front. I slipped back into my panties and left my clothes in a pile and climbed the stairs.

The bedroom door stood open. He was already in bed, propped against the pillows in nothing but a pair of loose shorts, the outline of his cock already thick and heavy against the fabric. The second I stepped inside he sat up straighter, eyes raking over the fishnets.

"Fuck, look at you," he said "My pretty little sissy in fishnets. Come here and show Daddy what that slutty ass can do."

I climbed onto the bed, turned around, and straddled him in reverse cowgirl. The nylon rasped softly against his shorts as I ground down, rolling my hips so my cheeks dragged along the rigid line of his cock. I could feel how hard he already was, twitching every time I pressed my hole against him through the thin layers. I wrap both my cheeks around his cock as I was grinding and I could tell he liked it especially when he slapped my ass in the fishnets.

After a minute of that slow, filthy grind I reached back, hooked my fingers in his waistband, and tugged the shorts down. His cock sprang free, leaking at the tip, harder than I had ever felt previously. I wrapped my fingers around the base and gave it a slow stroke, then leaned forward and dragged my tongue from balls to head in one long, wet lick.

"That's it, slut," he murmured, one hand resting on my fishnet-covered thigh. "Such a good little sissy for Daddy. Look how eager you are."

I licked him again, swirling my tongue around the head, tasting the first salty bead of precum before I opened wide and took him all the way down. My nose pressed into his pelvis, lips stretched around the root, balls resting warm against my chin. I held it for a second, throat fluttering, then pulled off with a wet pop only to sink straight back down. I repeated the motion three more times, each time forcing myself deeper until my eyes watered.

He started to move. His hips lifted, pushing his cock into my throat in short, steady thrusts. The gag reflex hit hard, so I wrapped one hand around the base to control the depth while he fucked my mouth. Spit poured out around my lips, soaking his cock, his balls, and the sheets beneath him, I was spluttering all over his cock like the filthy sissy whore I am, Every thrust made a thick, obscene sound, wet choking, gurgling, the constant drip of saliva running down his shaft.

I tasted more precum, warm and slick on my tongue, and it only made me hungrier. My own cock strained painfully inside the fishnets, a wet spot forming at the front. The sloppy noises I was making grew louder, messier, and every time I gagged around him I felt my own orgasm creep closer.

He was breathing harder now, hips snapping up faster. I switched to the two-handed twist, both fists working the spit-slick shaft while my mouth stayed locked around the head, tongue flicking the underside. The choking sounds turned constant and wet, desperate and rhythmic.

"Gonna cum down that sissy throat," he warned, voice tight. His hands clamped on either side of my head and he drove upward, burying himself to the hilt as the first thick pulse hit the back of my throat. I swallowed around him, taking every spurt while he kept thrusting through it, pumping load after load straight into my stomach. I didn’t pull off until he finally let go, cock still twitching against my tongue.

When I sat up my chin and chest were shiny with spit. I peeled the soaked fishnets down my legs, thanked him in a hoarse whisper, and slipped back downstairs. By the time I reached my car my own cock was rock-hard again, throbbing with every step. The drive home was five long minutes of aching need, the taste of his cum still on my tongue.

I hope you guys enjoyed, I should be meeting him again Wednesday he has just bought me a red plug and red fishnets to use and I can’t wait 😘

This is my second story. Writing about how it started from the very beginning. I'm keeping it short and brief. Every story coming from me is absolutely Real.

I was a teenager. No facial hair or body hair.  Under matured for my age. Tiny dick and had just learnt to masturbate. The person who opened me up to this new journey a Swim coach was in his late 30s or early 40s. Good physique. 7 when hard and dark complexion.

It was summer holidays. I went swimming every day after noon in a nearby swimming camp. They had several batches of 1 hour every day until evening. I usually went to noon batches. It was a huge pool with enough shower and changing rooms.. but then since it were holidays the pool would be crowded and few wud need to change near tall walls or trees.. which I kinda liked. I had found a place behind 2 water pump rooms where no one could see me change. I wanted a very secluded place because I didn't want anyone to see my tiny dick. So after my swim i'd take a quick shower and rush to that place. I would get fully nude. Then towel dry my hair and body. Wear clothes and leave.. this went on for many days until one day when I was drying my body standing naked i heard sounds from above the room and noticed one of the coaches or guards was on the top of that room plucking jamun fruits from the nearby tree branches. And he was looking at me.. out of panic i immediately wrapped my towel around and acted normal. When I looked back to him he was still looking at me and showed signs with his hands to remove my towel and show him my naked body.. at tat moment my heart rate doubled and don't know why but I did what he asked me to. I stood there naked for few seconds.. he signalled me to turn.. so I did and gave him a proper view of my back as well. Then I wore my clothes and left.. this continued for couple more days until he came to me and said - "come morning this Sunday. The pool will be closed for public and I'll teach you few techniques to swim easier". I knew wat this meant and I was very excited and couldn't wait.. During this waiting period i thought how all this happened and where it can lead to. He must have watched me don't know how many times and I'm sure he liked my slim hairless fair body with a tiny dick. I could not stop thinking what might occur this weekend. Finally wait was over and it was weekend. I showered and left. Reached the pool but the gate was locked. I asked the security guard there if the coach had come as he had called for weekend practice. To my luck he said the coach was inside and opened the gate for me. Don't know why but the guard gave me a weird look. Anyway.. I walked in.. the whole campus was empty. I couldn't spot him soon. Then saw him inside the pool swimming. He waved at me and asked me to get in.. I wore my trunks.. with a buldge as I was rock hard. And jumped in. He came near me and whispered in my ear, No one will disturb us now remove ur trunks and feel free. It was happening quickly.. he was rubbing against my thighs and I noticed he's fully naked.. woww.. I got naked too.. he humped me for a while caressing pressing my chest and ass.. he grabbed my dick and said.. it's so cute.. though it was tiny.  He guided my hand towards his dick.. he was hard and a real big one.. I loved it to hold and press his dick in my hands.. After sometime we got off of pool and he took me to his coaches room.. I immediately held his dick again and told him it's so big and nice. He said yes and that it was clean now to kiss it . I hesitated a bit but gave it a kiss.. He said- that's enough for you? Did u not like it? I replied yes and started to lick it.  Then as he said I sucked him.. then his balls too.. he then slowly throated me along side pressing my dick and balls.. he was about to cum.. he pulled it out and came on the floor. We got dressed and left.. no further talk. . Wow.. I wondered if I did something wrong.. anyway the stalking of me continued and we met again the very next weekend.. Everything was similar except we did few extra things.. He fingered me and inserted just the tip of his dick.  He sucked me like for 10 seconds.. it was heaven .. this time he fucked my mouth and came inside my mouth.. How this progressed into a Daddy sub relation is a story for another time.

This is something Ive never told a single person but I need to get it off my chest. Im a bigger guy and for years now Ive been secretly wearing womens panties and lingerie pretty much every day. It started back in college and just never stopped.
My mom has always been the type to hit up outlet stores and buy whatever is dirt cheap in bulk. Shed send me boxes of stuff thinking I could flip it for extra money for school. For a long stretch it was womens swimsuits then it switched to panties and lingerie. I was selling most of it but one night I got pretty drunk and on a whim decided to try a set on.
I honestly expected it to feel ridiculous. Instead it felt amazing. The fabric the way it fit how it looked on me even as a bigger dude just hit different. I stood in front of the mirror way longer than I care to admit. That drunk experiment turned into something I kept doing just once in a while which very quickly became every chance I got.
Fast forward to now and I havent stopped. I wear them under my regular clothes to work when Im running errands pretty much everywhere its safe to do so. I love how they feel. I love feeling sexy in them. I dont think Im trans. I dont identify as a sissy or anything like that. Im just a guy who discovered he really really likes dressing in womens lingerie because it makes me feel good and confident in a way nothing else does.
Ive only ever hooked up with a couple guys while dressed up and those experiences were intense to say the least. But even without that the lingerie itself is the main thing for me.
No one in my life knows. Not friends not family not past partners.

I’ve been a member of this same 24-hour gym for about 3 years. I’m currently 5’6”, 145 lbs, smooth from the eyes down, and I always wear tight panty like compression shorts under my regular gym shorts because I love how they hug and lift my fat ass, making it look plump, round, and fuckable. There’s this older, muscular black guy easily 6’3”, 240 lbs of solid, veiny muscle who’s been a regular longer than me. He usually works out late at night, just like I do, I’ve caught him looking at me or my ass more times than I can count, prob because the gym is more empty and there's less people around we see each other easily. But nothing prepared me for the time several weeks ago when I walked into the locker room one night.  My workout lasted a little longer than usual that night, when I finished up I headed to the locker room to take progress pics. I walked in and saw him standing there completely naked, drying off. His cock was soft and still hung heavy between his thick thighs, easily 6 inches even soft, thick, veiny, and shiny under the locker room’s lights with a fat, dark mushroom head. I froze in the doorway for a split second staring. Then tried to continue like it was nothing new to me. He caught me staring and just smirked, slowly turning so I could see the full length and weight of it swinging from my locker. As I tried to ignore him and take my pics in the mirror I kept stealing side eye looks at his monster snake. That image has lived rent-free in my head every single day since. I would vibrate my caged clitty while fucking my ass thinking about it at night, imagining what it would feel like stretching me open, owning me, breeding me, ruining me for anyone else. After weeks of fantasizing I finally stopped pretending. I went to the gym extra late, around 11:30pm, hoping it would be practically empty. I was right, there were only two other people there along with the BBC stud. I did my usual glute-focused workout — hip thrusts, sumo squats, cable kickbacks — arching my back extra hard on every rep like the desperate attention whore I am. I wore my sluttiest pair of white compression shorts that ride up between my cheeks, making my ass look extra juicy and inviting, along with a g-string and inverted chastity cage that I always wear. By the time I finished, the gym was completely empty. My heart was hammering as I walked into the locker room. He was already there. The room was dead silent except for us. He was standing by his locker in just a pair of gym shorts, no shirt, sweat still glistening on his dark skin. When I walked in, he looked up and gave me that same knowing smirk that made my knees weak. I smiled back and tried to act normal. I opened my locker and started stripping for him. I never change when at the gym but It was his turn to see my naked body. When I pulled my compression shorts down showing off the string buried in my cheeks and my little pink chastity cage popping out, I heard him let out a deep, mocking chuckle. he was on me instantly. He came up behind me so quickly and grabbed me by the throat with one big hand and slammed me against the lockers so hard it knocked the wind out of me. “You’ve been teasing me with that fat white ass for months, you little fucking cocktease,” he growled, his voice low and dangerous. “Tonight you’re not leaving until I wreck that hole.” I tried to say something but he interrupted me with: “Look at that pathetic little thing,” he said, voice low and rough. “All this time shaking that fat white ass in my face during squats and you’ve been locked up like a desperate sissy faggot the whole time.” My face burned with shame, but my caged clitty twitched hard inside its pink prison. I think at that point I started leaking. I just kept looking at his massive bulge. He reached over with one hand onto my cheeks and with the other flicked my cage with one thick finger. “You’ve been teasing me for months, bitch. Prancing around in those tight shorts, bending over in front of me, showing off that juicy ass. You knew exactly what you were doing. Time to stop pretending and take what you’ve been begging for.” Before I could even respond, He forced me down to my knees on the cold tile. His shorts dropped and that massive cock slapped me in the face. It was already rock hard, it had grown to 9 thick inches. It was musky smelling, and was coated in sweat like oil that made it shine like the last time. His big black cock smell hypnotized me, turning me into an obedient slut. “Open your fucking mouth.” I hesitated for a split second, he slapped me across the face and caught me off guard making me open my mouth involuntarily. He then shoved his big cock straight down my throat. I gagged violently as he started face-fucking me making me take it deep down my throat without mercy, balls slapping my chin, using my throat like a fleshlight. “Choke on it, you worthless white sissy. This is what you get for teasing me.” Tears streamed down my face. Spit poured out of my mouth as he brutally fucked my throat, holding my head in place against the lockers so I couldn’t pull away. I was coughing and gasping for air but he didn’t care. Pulling out for a quick second, the smell hit me like a drug, strong, masculine musk mixed with musky sweat from his workout. My eyes rolled back a little. He grabbed my hair and rubbed his heavy, oily balls across my face. “Lick them, bitch. Worship them.” I obeyed instantly, running my tongue over his smooth, heavy sack, tasting the salty sweat. I sucked one ball into my mouth, then the other, moaning softly as I did it. The smell and taste were driving me insane. I was whimpering like a slut. He pulled back and slapped his thick cock against my face a few more times, smearing pre-cum across my cheeks and lips, then shoved the fat head past my lips. I took him  back into my mouth, stretching my lips wide around his girth. He was so thick my jaw was aching immediately. He grabbed the back of my head with both hands and started face-fucking me again, pushing deeper and deeper until I was gagging and drooling uncontrollably. Nonstop pounding the back of my throat, spit poured down my chin onto my chest. Every time I tried to pull back for air he allowed me to breathe in then quickly pushed harder, forcing me to take more of his thick black cock down my throat. “Fuck yes… choke on this black dick, you little bitch. This is what you’ve been craving, isn’t it?” Tears were streaming down my face but I kept sucking, desperately. The smell of his musk, the taste of his pre-cum, the way he used my throat like a cheap fleshlight it was everything I had fantasized about for weeks. After about 20 minutes he pulled out, allowing me to catch my breath, then one last plunge in for a big deep throat. He pulled out quickly and surprised me. strings of thick spit connecting my swollen lips to his glistening cock. After what felt like an hour, he yanked me up by my hair, spun me around, and bent me over the bench. He reached into my crack and pulled my string to the side, then spit on my hole once and forced his fat cockhead against it. I whimpered, “Wait… please…” “Shut the fuck up.” He pushed in hard. Since his cock was so slick with all my saliva it easily breached my asspussy. The stretch was brutal, I cried out as he forced every thick inch into me in one savage thrust, not stopping until his heavy balls were smashed against me. “Fuck… that’s a tight little pussy,” he groaned. Then he started raping me. He pounded me mercilessly, hips slamming into my ass with loud, violent slaps. Every brutal thrust slammed into my prostate massaging my spot from within and made my caged clitty leak all over the floor. I was moaning and crying at the same time, completely overwhelmed. He grabbed my throat from behind and growled in my ear: “Take that dick, you little white bitch. This is what you’ve been begging for.” He fucked me harder, pulling almost all the way out before slamming back in, destroying my hole. The pain mixed with intense  pleasure until I couldn’t tell which was which. I was pushing back against him even as I whimpered “too big… please…” He laughed and fucked me even harder. His BBC was rubbing past my p-spot in a perfect rhythm making me drip insane amounts of clear sissy juices from my cage.  After some time he pulled out and i felt my hole convulsing and twitching rapidly. He spit on my hole some more, rubbed the fat head of his cock against my twitching swollen ass lips, and pushed. The stretch was insanely pleasurable. I gasped loudly as the thick head popped back inside me. He didn’t wait. He kept pushing, forcing every thick inch into my tight ass until his heavy balls were pressed tight against me. At first I was squirming around as my hole was adjusting to his massive pole but he held me in place firmly. At this point I was his motionless sex toy, taking every deep thrust he wanted to give me like a good slut.  “God damn… your pussy is gripping me so fucking tight,” he groaned and began unloading his cum into me. I could feel his BBC twitching and pumping my guts with his seed as he rested balls deep for like 15 seconds. But soon after he continued fucking me like he hated me. He pounded me mercilessly from behind, hips slamming into my ass with loud, slimy slaps that echoed through the empty locker room. Thankfully the only employee that works there at those late night hours just sits on their phone by the front desk, practically hating their job... Every brutal thrust slammed directly into my p-spot, sending electric waves of intense pleasure through my entire body. I could feel an orgasm building that I could no longer hold back, I was far from any control. My locked clitty was dripping streams onto the floor beneath me in long, clear strings. I was moaning like a bitch, unable to stay quiet no matter how hard I tried. “All that time showing off your ass… you were begging to get turned into my personal cum dump.” He fucked me harder, pulling almost all the way out before slamming back in, making me feel every single inch. The burn mixed with overwhelming pleasure. The pain turned to pleasure and i found myself pushing my ass back into him like a desperate slut, desperate for more. He flipped me onto my back, threw my legs over his shoulders, and railed me even deeper. I could see his thick black cock stretching me obscenely as he pounded me. I started having a shaking, uncontrollable sissygasm — my locked clitty erupting in weak, pathetic dribbles while my hole clenched and spasmed around him. He didn’t stop. He kept destroying me through my orgasm, making it more intense dribbling more useless sissy cum. It was insanely hot and humiliating. This position let him go impossibly deep, paired with his creampie and my sissy cum as his lube. I could see his thick black cock covered in a white cream ring stretching my hole wide open with every powerful stroke. The wet, obscene sounds of him destroying my ass filled the room. “Tell me what you are,” he demanded, pounding me relentlessly. At first I couldn’t even comprehend he gave me an order and kept moaning, then he slapped my face and repeated himself. “I’m… I’m your bitch,” I cried out, lost in the sauce. Cant even focus on anything other than my hole getting destroyed. “Louder, faggot.” and slapped me again. “I’m your fucking bitch! Fuck me! Fuck me! Please!” He laughed darkly and fucked me even harder, the bench creaking under us. He kept this up for what felt like forever. fueling another intense sissygasm which didnt subside until switching positions. He stood me up, turned me around, and fucked me standing doggy against the lockers, one hand around my thigh holding it up because I was so weak at that point, while the other slapped my ass red. I could feel all of his 9 inches leaving and entering impossibly quickly. He was like a jackhammer or a piston ravaging my hole. Soon after he turned me on my back then he lifted me like I weighed nothing, pinned against the wall, and continued railing me while holding me up, my legs wrapped around him. I felt so small and powerless. He was having his way with me like I was a toy. He had me in any position he wanted, he laid down and had me ride him reverse cowgirl on the bench, slapping my ass and calling me his white bitch while I bounced desperately on his thick cock. When he came the first time, he buried himself balls-deep and unloaded. I could feel every powerful spurt flooding my guts. He stayed deep, grinding, holding me in place making sure it stayed inside me. As a man would do to impregnate his woman. I became his woman. But he wasn’t done. Not even close. He made me suck him clean, then got hard again in minutes. He fucked me in almost every position that night, breeding me 2 times twice deep in my ass and once down my throat while I was on my knees like a good cum slut. By the end I was a complete wreck. My hole was gaping wide open, cum leaking steadily down my thighs in thick globs. I lapped up whatever I could get onto my hands, but my face and chest were still covered in his spunk. I was shaking, moaning, completely broken and owned. He looked down at me, smirked, and said “Good bitch. See you tomorrow night.” Then he casually walked off to shower like he hadn’t just destroyed me. I sat there on the bench for a while recouping, cum still slowly dripping out of my ruined asshole and down my body, feeling completely ruined. After a few minutes I got up and collected my clothes and left. In the car ride home, I remember sitting in a small pool of his cum at one point, Which felt so yummy. It didn't really strike me as to what just happened until I saw my car seat the next day. my cotton seat was stained with a dark wet circle (which was a bitch to remove lol). I got home and changed out of my cummy clothes, and fell asleep almost instantly. I was shy to see him the next day, but I did go back to the gym a few days later and had some more fun with him. I can write about that another time. The end. ;)

My grandparents have a cabin that they let any family member use. I decided to take my GF up for a little get away this week. There's all kinds of fun to have there; hiking, scenic drives, swimming, and best of all they have a very nice hot tub! My GF was very onboard with this and we went up. I told her how much I love the hot tub and how nice it would be especially for how chilly the mountains get in the evening. Well we get there and on night 1 she says she's got 3 swimsuits for me.

Night 1: We matched this evening! It was a simple black bikini with tied halter top and side tie bottoms! This bikini came with a tiny crop top that said "Yes, Daddy"! We kept talking about how fun it would be to share a Man!

Night 2: I guess she was feeling patriotic because I wore a USA printed 2 piece bikini! The triangle cups had the stars and the bottoms were the stripes. She made me hike these up a good bit as she grabbed my ass a lot this evening!

Night 3: Basically lingerie. It was a TINY pink stripe too and side tie bottoms. We didn't even make it to the hot tub... once I tried it on it led to the hottest sex on the floor. Ofcourse it stayed on!

True story on how an admire made me rethink my entire life. I enjoyed writing this may do more in the future :)

My girlfriend had been gone for three days. She left for Europe with her family and they really wanted me to come along. I told her work was too crazy right now and I needed some quiet time to catch up. That was partly true. The deeper truth I never said out loud was that I wanted the house completely to myself.

I have been crossdressing in secret since I was little. It started with quiet little moments sneaking into my moms closet. The soft brush of fabric against my skin always made something warm bloom in my chest. It stayed hidden for years. Then lockdown hit. Working from home gave me hours alone every single day. That is when Becky really came alive. I bought my first pair of heels. I spent late nights watching makeup tutorials. I learned how to blend eyeshadow until my eyes looked bigger and softer. I learned how to line my lips just right. It was not just the clothes anymore. It was the whole ritual. The sweet powdery smell of foundation. The soft click of heels on the floor. The way a dress made my skinny frame feel graceful instead of awkward. I fell in love with putting outfits together and feeling pretty.

But no one knew. Not my girlfriend. Not my friends. Not my family. Becky was my private world.

Until Reddit.

I posted a safe mirror pic in a crossdressing subreddit one night when the urge got too strong. Brandon commented. He was 48 and worked high up in a construction company. He was married but very discreet. His messages were kind and patient. He asked real questions like what I loved most about being Becky and how it made me feel when I was all done up. We chatted for days. I told him straight up I was not into guys. He respected it completely. Then he asked for my email and surprised me with gift cards. Five hundred to Fashion Nova then Amazon then Ulta. Just because he said he loved seeing me happy and pretty.

Something deep inside me cracked open after that.

I started flirting back in the texts. I told him how sweet he was and how his words made me feel soft and dainty and seen. I even opened up about being in a long term relationship and that Becky was only part time. He was so understanding. "You deserve to explore this side safely, princess. No pressure at all."

That morning with the entire house empty and quiet he sent another thousand dollar gift card.

"Go to the mall today since you are home alone," he wrote. "Buy whatever makes Becky feel beautiful. I would love to chat while you shop if you are comfortable."

My heart was already racing as I stood in front of the mirror.

I went full Becky first. I shaved everything smooth. I lotioned my skin until it smelled like warm vanilla and felt like silk under my fingers. I did my makeup carefully. Soft smoky eyes that made them look bigger and more inviting. Rosy blush on my cheeks. Glossy pink lips that tasted sweet when I pressed them together. I slipped on my favorite blonde wig and styled it into loose waves. Then I put on a cute long sleeve top and skirt just for the mirror. I felt so pretty so dainty so alive.

I took several Snapchat selfies. Mirror poses with my hand on my hip. A soft smile. One where I turned slightly so the fabric flowed. I sent them to Brandon.

Me: "Feeling extra pretty this morning because of you. Heading to the mall soon."

Brandon: "Fuck princess. You look absolutely stunning. Those eyes. That smile. You are going to turn heads even in boy mode. Send me everything you try on."

The compliment made heat bloom low in my stomach. I changed into baggy sweatpants and a hoodie over the cute lace bra and panties. I wiped off the visible makeup but left the smooth skin and secret lingerie underneath. I felt the lace brushing against me with every step as I drove to the mall.

The first store had racks of long sleeve dresses. My safety net. They hid my arms and tattoos and made me feel softer and more feminine. I pulled out a flowy floral maxi with delicate sleeves. A leopard print mini and midi set. Several skirts and tops. I snapped pictures from the rack and sent them.

Brandon: "The leopard one. You would look so fucking sexy in that. I can already picture taking you out to dinner. My hand sliding up your thigh under the table while everyone else thinks you are just my elegant date."

I tried the floral maxi in the fitting room. The fabric whispered cool and silky against my freshly shaved legs when I turned. It flowed beautifully. I stood there staring at myself in the mirror. Cheeks flushed. Heart pounding.

Me: "Trying this one on. It feels so pretty on my skin."

Brandon: "Good girl. I bet it makes you feel like a real princess. Spin for me next time you are brave."

We went through four or five outfits like that. Each time he described exactly how he would take me out in them. Holding my hand. Pulling me close in the car. Whispering how beautiful I looked. Every message made the euphoria build higher. My hands shook when I paid.

The makeup store was next. The sweet powdery scent of lipsticks and foundations wrapped around me the second I walked in. I tested shades on my wrist. Feeling the smooth glide of gloss. Brandon kept texting.

Brandon: "You are so cute when you get excited about this stuff. Tell me what you are buying princess. I love how feminine you sound right now."

I bought new glosses. Blush. And mascara. His words made me blush hard in the middle of the store. Why does his approval feel this good? I am not even supposed to be into guys.

Then the shoe section. I found thigh high suede boots and strappy heels. I sent him pictures.

Brandon: "The thigh highs with the leopard dress. I want to see my pretty girl in them."

By the time I got back to the car my arms were full of bags and my head was spinning. The leather seat felt cool against the back of my thighs. I texted him I was heading home.

Then my phone rang. Snapchat call. Brandon.

I stared at the screen. Heart hammering so hard I could feel it in my throat. I had never used my feminine voice with anyone before. But something in me answered.

"Hey..." My voice came out higher. Breathier. Softer. It felt strangely natural.

"Hey princess," Brandons deep warm husky voice filled the car. "You made it through the mall okay? You sounded so excited in your texts."

"Yeah I did," I said softly. My feminine voice steady even though my hands were shaking on the wheel. "I got a lot of stuff. Thank you again. I cant believe you did that for me."

He chuckled. The low sound sent a confusing shiver down my spine. "You deserve it Becky. Hearing how happy you got picking everything out made my whole day. Tell me what you are most looking forward to wearing for me first."

I drove the rest of the way home lost in that deep voice and the way it made me feel small and pretty.

Back in the bedroom I laid everything out and started trying things on again. This time fully dolled up. I sent him cute pictures and videos. Posing with one hand on my hip. Turning so the fabric moved. Looking over my shoulder. I felt like I was flirting. The realization hit me like a wave. I am actually flirting with a guy right now. And it feels exciting.

He sent pictures back. One in a sharp suit with friends. Tall. Broad. Confident silver fox. Then one in a bathing suit. He was ripped. Strong. Muscular. Powerful but not bulky. Dark hair with hints of grey. My breath caught.

Oh my god. He is really attractive.

The confusion and nervousness mixed with a rush I could not deny.

Something in me snapped. I changed into the long sleeve leopard bodycon mini dress. Black tights. And the thigh high suede boots. I retouched my makeup. Smoky eyes. Glossy lips. I looked in the mirror and felt it click.

I video called him.

He answered immediately. His handsome face filled the screen. Warm smile. Those intense eyes.

"Princess. You look incredible," he said. Voice dropping lower.

We talked. Laughed. Flirted. Then I whispered. "It would be funny would not it? Being your part time girlfriend. You flying me out. Showing me off. And maybe one day earning my trust enough to be the first man to kiss me."

The words hung in the air. Heat flooded my body.

Brandons voice turned dominant and smooth. "Oh you really are good at being a girl. I wish I was there right now. I would put my hand gently on your neck. Tilt your face up. And kiss you slow while you looked up at me all submissive like that."

I moaned softly before I could stop myself.

"Oh my God. Daddy."

The word slipped out so naturally it scared me.

From there it escalated. I slowly stripped down to just the delicate lace lingerie while he watched. Telling me exactly how to pose. Hands on my hips. Looking up submissively. Turning so he could see everything. He praised me constantly. How pretty I looked. How feminine. How much he wanted to take me and make me his woman.

I was breathing hard. Touching myself. Moaning. "I need it Daddy. I need you to make me your woman. I need a real man to take me."

When he came he told me to finger my bussy until I did too. I did. Hard. Shaking. Moaning his name.

The post nut clarity hit like ice water. Shame crashed over me in heavy waves. I sat on the edge of the bed in just my panties. Staring at the floor. Heart pounding. What the fuck did I just do? I have a girlfriend. I am not supposed to want this. I am not supposed to like men when I am dressed up.

Thirty minutes to an hour later my phone buzzed.

Brandon: "I am excited for you to be my secret little part time girlfriend princess. You were so beautiful today. Can not wait to do this again."

I stared at the message for a long time. Shame and that warm confusing glow fighting inside my chest.

I did not know what this meant yet.

But something inside me had awakened for the first time. And I knew it was not going back to sleep.

A brief introduction: I’m a married, closeted sissy. I’ve never been to in-person meetups or tried real cock—only dildos. Lately, I’ve been challenged to do small things, like going to the store in a cock cage, wearing panties to work, and so on.

This happened when I was going on a three-day business trip; my Mistress had tasked me with wearing a flat cage and panties for the entire duration. Since I was mostly on my own, things had gone smoothly—except for the fact that I was incredibly horny.

I arrived at the airport a bit early and had plenty of time. I went into the restroom and chose the first available stall; there weren't many people around, and there was plenty of space. Since I was wearing a cage, the safest option was to pee sitting down. I had leaked quite a bit of pre-cum into my panties—walking around in public like that was a huge turn-on, and I was already very aroused to begin with. So, I was touching myself a little and licking up some of the pre-cum when the stall door suddenly opened—I had forgotten to lock it.

Time stood still for what felt like hours—though it was likely only a couple of seconds—before the man who had opened the door popped inside, locked it, and held a finger to his lips in a "hush" gesture. I was stunned by the situation and sat completely still on the toilet, utterly bewildered. The man leaned down and whispered in my ear, "Be completely quiet now and a good little sissy, and you’ll get to taste real cock. It’ll be our little secret." Then he unzipped his trousers and pulled out a semi-hard cock, about six inches long.

I was still in shock and said nothing; the man grabbed my hair and guided my head toward his cock. "Open your mouth, sissy, and get your prize," he whispered. I opened up and he slid his cock in slowly; it felt amazing to have a real cock in my mouth, not just rubber. My inner sissy took over, and I grew increasingly aroused. I sucked him deep into my throat, and it took only a couple of minutes before he shot a load into my mouth. I had to swallow to avoid spilling it on my clothes. He buttoned up his trousers and whispered, "Thanks—I know where you work, sissy; maybe we'll run into each other again." Then he walked out, and I locked the stall door...

My roommate found out that I used to dress in women's clothes, it turned out that I didn't know before that he likes femboys, needless to say, he was excited, he hadn't been with a girl in a long time, so his dick got really hard when he saw me

Picture this, Im in college, 21 years old, not social at all, only 1 'actual' friend and hes going to a different college on the other side of the country. Never had a girlfriend, never even kissed to begin with. Most of the time I spent behind my computer playing games and chilling with some 'online' friends on discord ect...

I basically started this femboy/cd thing in lockdown as a JOKE, ordering thigh high socks, fishnets and chokers, eventually tried shaving, loved the feeling of smooth skin, started taking pics and posting to 4chan and reddit, started getting some freaky captions and texts in my dm's and it slowly worked on my mind. Next thing I know, I ordered a dildo, looked at guides on how to clean ect... Loved the feeling of riding dildos so it got to the point where I struggled getting hard without a dildo in my ass lol.

And when dildos couldn't satisfy me I turned to hook up sites and started looking for the real thing, got an insane amount of messages but almost nobody was serious enough to actually meet up. Well until a guy started typing how badly he needs a hole to fuck so he can relief some work stress. Not gonna lie it sounded hot as fuck and he looked normal enough and not like a serial killer in his 50-60s, so I gave it a shot.

He gave me his location and I went to his place that same night. He opened the door, pulled me in, pointed me to the bathroom and told me not to come out until im fully ready. So I went in, got some fancy new lingerie from amazon (lol), trusty old pair of black stilettos and black stockings, wig and the most basic make up.

Opened the bathroom door, he looked at me, says 'oh fuck come here', I almost trip trying to walk to him and hes already grabbing my ass and kissing me up and down. That was probably the first time in a long time that I got hard without touching myself first. He started stroking me slowly while kissing and I could feel my legs shaking already. He grabs my shoulders, forces me to crouch and pulls down his pants. Bam, his dick right on my forehead lol. I start sucking it and its kinda freaking me out how fast its going. Before I know it, hes flipping me around and lubing up my ass.

It goes in and all i felt was pure bliss. First few thrusts he was gentle and then he flipped his switch. Grabbed me by the shoulder while in doggy and started fucking me rough like we were dogs let loose. He was stretching me out so good and I couldn't tell if it was pain or pleasure. He was all over me.

Wasn't long until he completely laid down on top of me and fucking me pronebone. There I was, laying on my stomach while this guy was pumping his stress away into my hole lol. I had a moment of realization and for some reason I didn't care. I legit got fucked in the ass before I fucked a girl and I didn't care about it. Aaaand he came. He shot his load on my back, smacked my ass a couple of times until it turned red and told me that its the best pussy hes had in a while.

I laid there next to the used condom and kept thinking about what happened. It probably helped that I didn't cum so I didn't hit the 'post nut clarity' vibe. He allowed me to shower at his place so I cleaned myself there and went back home. He already left me a few texts saying we need to meet again and we did. We repeated this probably like 15 times before he ended up getting a 'girl friend' and he threw me to the side :(

All that was going on while I was just that loner shy guy in my college class. lol.

The Real Dairies of Sissy!

Upon a muggy, sticky , summers night I found myself home alone for the evening. In fact , the rest of my family had left for a vacation. A vacation that I opted to stay home and skip it. I was 18 years old and I was secretly dealing with an identity issues. So I was so happy to have 7 days straight by myself. It was going to be a glorious week and I was excited. I had gotten serious about being a girl. After all, I had always felt like one. And I planned on living out every day of those seven days ,as a girl. My older sister was an absolute clothes addict. She had a walk-in wardrobe full of different outfits. We were very close in size and the fact that some clothes were a little tight on me, looked even better. And even though she took a lot of her clothes on vacation, she had so many outfits that it left me with enough to pick and choose. So as soon as they left, I ran to my sisters room. I Rummaged through her closet, put together an outfit ,and put some others aside as well.
For this evening I choose a short black mini dress , with back heals to match. I had recently bought myself a good supply of panties and I picked out a pair of black thongs . I also had purchased a cute pink chastity from a novelty shop and I couldn’t wait to try it. I had been dildoing my smooth young shaved pink pussy for about a year at this point. I enjoyed making my dick, as I always referred to it, as my clit , leak as I put pressure on my Gspot.

So I squirted a good amount of strawberry scented lubricant up my pussy for my plug. A few days prior, I just bought a new larger size plug. It certainly was a challenge to get it in due to the fact that I wasn’t use to it. As I inserted it into my pussy, a good amount of precum leaked down my leg.I even covered my chastity with slightly larger jar to collect any cum that leaked out. I never wanted to waste any of it. I had been eating own Cum for a long time. It was exhilarating to eat and Taste it. I grew to love the smell and the taste. I developed a secret obsession with Sperm. I consistently fantasized about tasting another mans spunk. I wondered how it feel having a real cock cum on my mouth. I yearned to find out. However, I was taught by society and my peers that being a fag was a bad thing. But that fact, made it even more alluring to me. And loved feeling of my pussy ( asshole) being penetrated. It instantly made me feel like a girl. Knowing that I can cum from getting fucked like a girl, called to me constantly. So the only thing better than a toys , was the real thing.

As for that night, I wanted the real thing. I wanted a cock. A mans cock. I wanted to be a girl for a man and feel what’s it was like to be a submissive. I had been planning this for weeks. I bought a 8 ball of coke earlier in the week from a dealer at school and couldn’t wait to start getting in that. I had recently discovered that cocaine fueled my sexual urges. I know it literally turns me into a depraved dirty slut with no inhibitions. I needed it to go through with my plan. I wanted to go all the way. I have been practicing my sucking skills on a 9 inch dildo everyday for a year. Used porn as my tutor to instruct me to do it properly. I conditioned myself to be completely feminine when sucking my dildos, just like how girls give head. And practiced my deep throating skills. I became very capable of taking a great measured cock down my throat.

Finally, I showered, shaved , cleaned my pussy with an enema, painted nails and applied moisturizer. I reapplied the scented lube up my pussy and put my plug back in . Locked up my clit and it would not be opened til the vaca was over. Then, I began to apply make up and transform. I had been growing my hair out for almost a year and it was just above my shoulders. I was proud of my hair. It was brunette, wavy and slightly layered. It looked very feminine when I wanted it to. So when I put the black dress on, everything came together. The dress fit perfectly. It showed my butt off , really well. I was so turned on I couldn’t wait to leave.

I knew exactly where I was going. There is a rest stop off of the highway about six miles from my house. About two weeks earlier I found out that it’s a cruising spot for gay men. I went twice before and I just couldn’t get enough nerve to do anything . I knew , I had to go there as a girl. I fantasized about it constantly, as the days counted down for my parents to leave. And now, the day came. I was a bit nervous with excitement as I got into the car. I drove the 10 mile ride and my heart was pounding as I made me way off the highway and pulled around the long curves exit for the rest area. I notice that the place was pretty busy. Cars where parked all though out the parking lot. I felt nervous as I found a spot to park in the upper parking area . As I pulled in, I shut my car off and rolled down the windows. It was very warm that night. It was mid July and during a heat wave . Inside my car was quiet. But outside I can hear the cars and trucks speeding along on the highway. I was still very nervous until I set up a big choker line of coke. I was barely able to snort it all in one swoop. There was still some left and I quickly snorted it. I lick my finger and stuck in the bag. There was a good amount on my finger and rubbed my teeth with it and swallowed it . I brought knees to my chest and legs went spread eagle in my front seat. I reached between my legs , and pulled out my plug. I then licked my finger again, stuck it in the bag and got a very large pile of coke and began shoving it in my pussy. I finger myself as the Cocaine took ahold of me. I was no longer nervous, my inhibitions were gone. I finger fucked myself for a good while. Until a car pulled up next to me. I put legs down, but the plug wasn’t all the way in. It was almost in as I wiggled my ass on my seat, and it gave much resistance as it went deep into my now numb pussy. Suddenly it broke through and pressed hard against my G-Spot .
I was squeezing my plug with the muscle of my hole. I could feel Cummies dripping out. The guy in the car was looking at me. I kept my focus on my cocaine loaded pussy and he waved me at me . I smile and looked away . He got out of his car and walked by the front of my car. Then he proceeded to walk across a grass divider, that’s was in front of where I was parked , to another parking lot for campers and smaller trucks. He then turn and stood facing me, in the wood line just about 50 yards away. At that moment, I was leaking so much that I thought I was going to fill the “ cummie jar” right there. I was so lost in a state of bliss as was grinding the plug against my prostate. I had to gain composure as I located him in my line sight. He was an older white man. Probably in his 60s. He had salt and pepper hair , def more salt than paper. He had on a white t-shirt and blue jeans. As he stood in the wood line I notice he was stroking his cock. Instantly I knew that it was my chance, and I knew I wanted it. Instead of waking over to him , I drove. I pulled about 20 feet up from him and got out. My throat was numb from the massive line I took. I wanted nothing more than to put his dick in my mouth . I walked right up to him and got directly on my knees.

There it was. Another mans cock right in front of me.

He ask me if I was a girl and, I looked up at him , and replied
“I wish “

“ You sure look like one. I couldn’t even tell. You even sound like one” he replied

I was on my knees in a wide open place. I knew that mostly anyone can see us if they just looked our way. But I didn’t care. I only cared about sucking this strangers cock.

He ask
“You want to make me cum ? Huh? You want to suck on this cock ? I’ve been edging all day. You sure you can handle it”

From down on my knees , and looking directly at his cock. I was only a few inches away from it. My mouth, though numb from the cocaine, was watering. I could smell his dick. It was the first time I had ever gotten the chance to know what a mans cock smelled like. The aroma was intoxicating. It captivated my sense and formed a mental imprint of how cock smells. I knew I loved it before I even did anything . As I was merely inches from his erect I could l see a good bit of it in the dim light.

Finally I nodded

But I couldn’t really formulate any words. I froze for a moment as a moment of panic set in. Just then I had felt my nose start to run. so I quickly snort it back up. To my delightful surprise it was a bunch of cocaine that must of been in my nasal passage. It Brought me back to what I was seeking.

He said “ Go ahead . Make it cum .” He said, as he grab his cock and slowly stoked it.
He had an average size cock. about 6 or 7 inches. It wasn’t particularly thick, however , but it had a nice mushroom head. And it curved up. His pee hole glistened with precum when it caught the reflection of surrounding light. There was a good amount of it too..He was hard and ready. My heart was speeding as I knew it was time. I had trained for this and I was set to do it right. I pressed my two lips against the tip and kissed it. His cock twitch up and quickly back down. His precum smeared my lips. I pulled away as I licked my lips. I got a good taste of it and it was delicious. The flavor of his pre-cum send me over my heals. I again kiss his cock, and this time I didn’t pull away I slide my pretty pink lips over his head and stopped there . I sucked as much of his precum as I could . I kept very high suction around his Cum cover head. I used my tongue to swipe over his pee hole and then circling his cock head. I could feel the pronounced ridge of his swollen mushroom head with my tongue. The sensation of a real one, was different from its synthetic counter part. And it felt so right.

He let out a moan

He said “ Oh you are something else kid. And You are a very pretty girl.”

I was too busy to reply. I was sucking his precum like it was the most tasty dessert I ever had. I then swallowed , and went for his balls like I learn from the porn movie. I pressed my face into this strange old mans ball sack. I began lightly licking underneath them. I reached up with my left hand and gripped his throbbing cock. I sucked one of his balls in my mouth and I lightly moaned.

“ Oh yeah ! Suck my balls.” He said in a half moan

I suck on his balls for a tiny but more. I was very surprised and relieved that he was freshly washed. He tasted yummy as I pressed my lips to the bottom of his shaft and I stuck my tongue on it . I lick up from his balls to the top of his cock head. He had gathered more precum from his pee hole as it was about to dripped down his shaft. Once again I slide my lips over his cock head and began go suck all of his precum. Precum taste so good to a “Cum Goon” like me and I wanted more. I pulled slowly off his cock head and kiss it again. I kiss it as I swallowed this strange old mans Spunk. I then wrap my lip around the the tip of his cock and I slowly work my way down his shaft. I made sure that kept constant strong suction as I slid down his cock. I was half way down his cock when I stop and slowly reverse my lips back towards the tip. Then again I slide down his cock. I would go a little Further down each time. As I slide down the last time I was able to press my lips hard against him as I had his entire cock in my mouth. I just stayed there I pressed hard into him. I was swiping my tongue at the base his shaft. His cock pulsated twice as I could feel him get harder.

He abruptly said

“ Damn it, you can suck a cock. You’re gonna make me shoot my load in no time”

At the moment needed a breath and I pulled off and immediately went right back down . I slammed my forehead and Lips against his body as he bottomed out. I repeated this 4 more times and then I pulled off, took as deep breath and went all the way down again.

The stranger grab the back of my head and began trying to force his cock in deeper .

“ Oh yeah. Take that dick in your throat. That’s a good girl”
He encouraged

At this point I gagged and pulled off. I had an immense amount of salvia and I spit on his cock and began sucking him all the way down again and back up repetitively. I try really hard to keep suction but it hard to do when your bobbing your head back and forth in such a speed. I pulled slightly down on his cock and gave it some resistance. It must of gave the stranger alittle more sensation, because his cock tighten up..I didn’t stop sucking like that. I would stop every once in a while at the base of his cock, deep throating him.

Suddenly he said “ oh I’m gonna shoot”
So I pulled back a little bit and began mouth stroking him over his swollen cock head.
I felt his cock harden , and twitch .
Suddenly he let out a groan like a wild animal

“ Ohhh yeah !!! “ He yelled
And I felt and endless jet of cum hit my the back of my throat. It was powerful and thick. After that one huge blast, I felt him pulsate a couple times.
He still groaning and moaning as he emptied himself completely. My mouth was absolutely full . I was leaking a good amount of spunk as he blew his old man sperm into my mouth. It was intense to feel a man lose control to an orgasm from my doing. After he settle down I continued to clean his cock and suck as much I as I could out.
He stepped back, and put his cock back in his pants.
“ I hope to see you again “ he remarked , as he walk in the direction of his car

There was so much cum In my mouth , it was dripping out of the Corners .

I walk to my car and spit the mouthful out into a jar I bought with me to save Cum. I look at his cum in under the light and I smelled it. I took a sip and swallowed some. It smelled sweet and clean. It tasted a bit sweet. I was in a different world. I couldn’t believe I had gone through with it. I was completely buzz from the sexual high . Not to mention the coke. I kept playing his powerful cum shot over and over again. Feeling his cock tense up, pulsate and then slam my throat and mouth with a thick load was better than I ever imagined. I knew, at the moment, that his cock was just the beginning.
Jillian Jordan

April was passing quickly, and anticipation for May was steadily building inside me. The last time we were together would have been New Year's Eve when we spent the night in a secluded spot parked in his car. He had mentioned that he would be done with his freshman year of college on the second Thursday of the month.

'Would you want me to come down and help you get moved out?' I texted him.

'I'd love that, but don't you have to work?' He replied.

'I'll just request it off, it's been slow anyways and there aren't any signs of it picking back up before then.' I typed.

'I mean, I want to see your, but I don't want to make you feel like you have to.' He replied.

'I think you'll make it worth my while ;)' I messaged back, hoping that we were on the same page.

'I'll certainly try :P' He sent back.

A few minutes later another message came through; 'I want to ask something, but I worry about what you will say.'

'Ask me :)' I replied, trying to seem open and positive to whatever he was going to ask.

'I wanted to try something but I got too shy to ask at Christmas, and if you don't want to I completely understand...' his message read.

'What do you have to be shy about?' Just ask :)' i replied.

'I was wondering if you would be opposed to dressing like a girl? Sorry, I just think it would be so hot to see you all dressed up, and makeup and hair done. If it's too much, no worries at all :)'

'We'll see :)' I replied. The thought of it was foreign, but arousing at the same time. Later that night I got on my laptop and shopped around for some things to fulfill his fantasy. Although I had no idea what to get, I wanted to surprise him, so asking his thoughts on anything was out of the question.

After a while I bought a simple matching lace bralette and panties, and a sundress. The day finally arrived, and I could feel my heart beating faster and faster as I got my new outfit on, did my makeup and hair as best as I could and left home to go see him. I had barely left town and I could feel that my panties were already soaked. As I drove, I gently rubbed my cock, thinking to myself about how hot it felt to be doing this for him. I let myself daydream about everything I was going to do to him as the miles flew by. Five hours went by quick and I texted him that I was just coming into town. He sent me the address to his dorm and said 'I don't have much stuff to bring back. I cant wait to see you :)'

'I can't wait to see you either :).' I replied.

When I pulled up to him I saw a look of disbelief and surprise. He quickly put a few bags in the back and climbed into the passenger seat.

'I didn't expect you like this.' He said, smiling.

'I hope you like it.' I said as I softly leaned over and kissed him.

'I love it. Were we not in such a public place I'd take you right here.' He whispered as he kissed down my neck.

'That will have to wait until we find somewhere more suitable.' I whispered back as my hand moved onto his thigh and then up towards his cock.

'What did you have in mind?' He asked as I could feel him getting hard through his pants.

'Hotel room? Unless you'd rather wait until we got home.' I replied.

'I don't think I can wait.' He whispered.

'I don't think I can either.' I whispered back to him as our lips touched again.

We left his campus and drove straight to the nearest hotel. We quickly checked in and briskly walked to the room. The door had barely clicked closed when we started making out and running our hands all over each other. He turned me around quickly and pulled up my dress, rubbing my ass as he kissed down my neck. I moaned softly as his lips and hands rediscovered my body, and my hand moved down his body onto his cock. I felt his bulge growing, and I could feel myself soaking my panties again. I felt his hand move down my back, slowly sliding in my panties. I leaned towards the wall, pushing my ass out and moving my legs apart. I felt his finger touch my asshole and moaned a little louder.

'Mmmm do you like that babe.' He whispered.

'God yes.' I moaned as he continued to rub me.

'Don't move.' He said, slowly pulling my panties down around my thighs and kneeling down behind me. I felt his hands move up my legs and gently spready my ass apart. I closed my eyes as I felt his tongue run over my asshole.

'Oh babe that feels so amazing.' I moaned. I looked at our reflection in the mirror and thought how amazing and hot his fantasy was turning out to be, and wishing he had asked to do it much sooner. As he continued to eat me out, I let myself get lost in the feelings of ecstasy he was giving me, and I couldn't wait to return the favor. After a few more minutes I pulled him up and gently pushed him against the wall. I pulled my panties off and threw them on the floor and then looked at him.

'My turn.' I whispered, then kissed him and knelt down before him. I rubbed his cock over his pants a little then undid his belt, unbuttoned his pants and pulled them down with his underwear. His cock stood straight out inches from my face as I wrapped my hand around it and ran my tongue on the underside of it. He moaned softly as I continued to tease him with my lips and tongue. He put his hand on the back of my head and softly guided me towards it. I parted my lips and put the head of his cock on my tongue and took it inside my mouth until I felt it hit the back of my throat. I started to move my head back and forth, massaging it with my mouth and tongue while my hands felt all over his body. As I continued to deepthroat him, I could taste his precum and felt a mix of it and saliva starting to drip down my face and neck. I looked up into his eyes as he moaned my name. As he looked down at me, I wrapped one hand around the base of his cock and with the other rubbed the tip of my cock which was dripping precum as well. I reached behind me and massaged my asshole with my precum soaked fingers.

'Let me finger your ass babe.' He moaned, pulling me up and then leading me to the bed. He laid me on my side and positioned himself so that he could finger me while I continued to suck him. He spit on his fingers and massaged me as I took him back in my mouth, and then started to gently push his finger inside me. I softly moaned while moving my head back and forth.

'God you're so good at that babe.' He moaned.

I took his cock out of my mouth for a second and whispered 'Only because your dick tastes so good'. I started sucking him again as he kept fingering me. He let me continue for a few more minutes and then pulled me up and kissed me. I let him massage my tongue with his for a bit as we felt each other's bodies some more. I wanted him inside me so badly.

'I want you to fuck my ass babe.' I softly moaned in his ear as I pulled his pants down around his ankles. He stepped out of them and walked over to his backpack and got a bottle of lube out of it.

As he walked back over to me I turned around on the bed and bent over. I felt him drizzle the lube on my ass and I rubbed it all over myself as he spread it on his cock. I felt him rubbing the tip of his cock on my asshole and slowly trying to push it inside me. I felt it finally got in and felt a wave of warmth rush over me. As he got it all the way in I gasped. He paused for a minute and I could feel it throbbing inside me. He pulled my torso up towards his and wrapped his arms around me. I turned my head towards him and we kissed again.

'Your cock feels amazing babe.' I moaned. 'Fuck me like the slut I am.'

He began to pull it out of me and put his hands on my hips, kissing my neck as he pushed it back in. I closed my eyes and moaned his name as I felt his cock sliding back inside me. He began to start his rhythm as our moans comingled with the steady sound of his hips and thighs slapping against my ass. I could feel my own precum dripping onto my legs as he kept fucking me. He slowly lowered me down onto my hands as he continued to thrust and started to moan louder. After another minute or so he pulled his cock out of me.

'I need you to get on top for a bit babe.' He said as he laid down on the bed. I got up and straddled him and sat back down on his cock, slowly pulling my sundress over my head and throwing it on the floor. I started to grind my hips back and forth on him, feeling his cock throb in my ass. I could feel him hitting my g-spot every time I went back and looked down and saw that I had already covered his stomach with pre-cum.

'Mmmm you're really wet.' He moaned. 'Are you gonna cum for me?.' He asked.

'Of course babe.' I moaned, switching from grinding on his hips to bouncing on his cock. 'After you cum in my ass.'

I leaned back onto my hands as I continued to ride him, focusing on the feeling of his cock going in and out. Each time I got to the bottom I felt it pressuring my g-spot. I could feel my body shaking as I felt my body get tighter and tighter. His stomach was slippery from my pre-cum, and when I looked down again I noticed that my cock had started to drip cum. I kept moaning his name as I felt us both getting closer and closer to cumming. I moved my hips up and down faster and faster as everything got tighter and tighter. His hands had moved to my hips and everything felt so amazing that it was making it hard to breathe.

'Oh my god babe your cock feels so good.' I moaned. I leaned back supporting myself with my arms as I kept trying to make us both cum. Every time I got to the bottom of the movement I we moaned, both desperate for release. I started grinding my hips against his faster and faster when the tension finally broke in my body and I came all over his stomach and my thighs, trying to keep going so I could make him cum.

'Don't stop baby I'm so close.' He moaned.

'God I love riding your dick so much.' I moaned.

As I got to the base of his cock, he moaned really loudly and I felt the warmth of his cum inside me. We both moaned in relief as I laid on top of him, his cock still throbbing inside my ass.

'Oh my God babe.' I sighed as he kissed my neck.

'You're incredible, thank you for dressing up for me.' He smiled.

'Of course, I'd love to do it again for you. It was so hot.' I whispered before kissing him on the lips. He pulled out of me as we continued to kiss and feel each other's bodies while we waited for each other to be ready again.

The first time I met with him, it was on a beach near my house, but this time I finally let him inside. My room it was asleep so we had to be quiet, but I snuck him into my room and he helped my mouth shut and I proceeded to suck him dry and he went 10 inches deep in me for over an hour until it was too painful for me and then I sucked his dick until he was about to come, and I made him come inside my ass and then I put my butt plug in to keep the cum inside my ass. How much of a slut am I?

I’ll post some more detail, but it just happened that I have to be quiet, but oh my God, one of the best experiences of my life

I was pretty horny, got dressed up and went for a walk..

Then à coo car goest by but it was kinda far, but they slowed down more and more White I was ALONE.

I think to myself that they were joking like "look is rhis a sissy ?"

Then they went and I met them again later ! They were in front of a pub, sorting things out.. I think they didnt saw me the 2nd time

Gonna post the video because luckily I got thid on tap :3

One night, my ex and I had gotten into an argument. A lot of it centered around me crossdressing. There are plenty of stories on here of me dressing with her, but her support of it came and went. Anyway, she decided to go see her sister and stay the night there. Which left me with a chance to get all dolled up.

I drove about an hour away, found a rest area, and started getting ready. I threw on a tight little burgundy dress, 4” pumps, some lace panties and a matching bra, and did my hair and makeup. I rode around for a few hours, flirted with some strangers, and took some photos.

After a little bit she started blowing up my phone wondering where I was. She’d gotten home and started drinking wine. I was honest about where I went and she freaked. She told me to come home right now or else. I don’t like confrontation so I just told her I should wait until we both cool down and I’d be back in a bit.

About an hour goes by and she sends me 4-5 pictures. They’re screenshots of a video of me getting railed by a stranger in a hotel. A couple were of me with a cock in my mouth, one was me smiling up at the camera, and a couple were of me getting fucked from behind. “Which one do you like best?” She asked. I asked her what she was talking about and why she was asking. “They’re the thumbnail for your big debut” she said.

Then she sent me screenshots of profiles from multiple different porn sites. She’d made me a full on profile full of face pics and info about me and the video of me getting fucked was in the drafts just waiting to be posted. This was before any of the ID verification or anything on a lot of these sites so she was just making profiles anywhere she could.

I begged her not to post them. She told me she’d started uploading them but if I was home before they finished she’d delete them. I was an hour and some change away. There’s no way I could get there. Then she stopped replying. I raced home and found her passed out with her laptop next to her. All the tabs were open and all the videos had been uploaded. I worked as fast as I could to delete them, but they’d all had several views. By the time I got done with the last one it had over 500 views (including some downloads).

The next day she apologized. She said she thinks I deleted them all but she couldn’t remember where all she’d posted them. Anyway, if you have my videos please don’t expose me 😅

I'm 32 and have been curious about dressing for years. I've only ever been with women but that changed last year. I finally bought myself a pair of women's boots and then clothes followed soon after.

I dressed most evenings in private and started posting pics on Reddit. I loved the compliments from both women and men. After that I started going into Grindr and chatting with men, especially older. I hit it off with one man, he's 61 and a week later we met up for a coffee. Things went fast from there.

He lived alone and provided a space I could dress more regularly and dress for someone in person too. This turned into a regular meet 2-3 times a week and still continues now!! I absolutely love dressing for a man and getting sexual too. I love exploring and sucking cock. It turns me on so much.