u/WorriedBoysenberry2

Her Hookup Era Chapter 4 [F30/M32] [Curvy] [Casual Sex] [Reverse Cowgirl] [Squirting]

Chapter 1 Chapter 2 Chapter 3

It was a bright and warm Saturday morning, the balmy weather tempered by a slight breeze. The patio around her buzzed with activity as Shay tilted her face toward the sun. She grabbed her glass of iced coffee, the condensation gently beading on to her palm, and took a long sip.

“So,” Dani asked, stabbing a piece of lemon ricotta pancake onto her fork, “how many times have you seen Truck Guy now?”

Shay sputtered slightly but managed to swallow her iced coffee rather than accidentally spraying it all over the table.

“Dani,” she pleaded, “can you please stop calling him that?”

Beside her, Anna laughed. “I actually think it works. Remember that guy I was seeing who worked at a liquor store?”

“Liquor Store Guy,” Dani supplied automatically.

“He has a name,” Shay announced to no one in particular.

“Julian,” Dani replied. “Yes, we know. But Truck Guy has a nice ring to it.”

Shay rolled her eyes good naturedly, taking another long sip of her iced coffee.

Anna squinted at her friend. “So, how long has it been? Two weeks?”

Shay shrugged. “Roughly. I mean, I like being around him. We're keeping it casual. We text. We meet up. Sometimes we get dinner.”

“And have insane sex,” Dani added around another mouthful of pancake.

Shay dropped her fork. “Jesus, Dani,” she hissed.

Her friend shrugged non-committally. “I call ‘em like I see ‘em. Besides, I know it must be nothing short of phenomenal, with that look that comes over your face whenever someone so much as mentions him. Not to mention you're more relaxed than I've seen you in a long time.” She paused, chewing another bite of pancake. “Actually, I haven't seen you this relaxed since before you were with James.”

Shay didn't say anything, just nodded sagely. She couldn't exactly disagree with anything Dani was saying.

“Wait,” Anna said, brow furrowed. “Do you think that this thing you have…well, that it might become something more?”

Shay didn't respond right away, but when she did, her words were thoughtful. “You know, I'm not really sure. We both got out of emotionally exhausting relationships around the same time and what we've agreed on for now is to stay casual. I like spending time with him, but I'm still healing from years with the wrong guy.”

Anna and Dani nodded in recognition.

Shay continued after taking a bite of her omelet. “I don't exactly have a crystal ball, but right now I'm honestly really happy with what we have going on.” She leaned forward slightly, voice lowered. “And yes, the sex is insane. In a good way.”

Dani squealed with delight. “I knew it!”

Later that afternoon, Shay felt accomplished. After brunch, she had done several errands and was now relaxing at home. Placing her e-reader on the coffee table, she realized she was curious about something. Most of her closet was full of skirts and dresses, and that was naturally what she had worn every time she had met up with Julian. She grabbed her phone and began to create a voice note.

“Question for you,” she started out simply. “Is there anything women wear that really drives you crazy?” She sent the message, curiosity blooming at what Julian might say.

A few minutes passed, and then her phone vibrated insistently against the smooth wood of the coffee table. Julian had responded to her voice note with one of his own. She quickly tapped it and his deep voice began to fill her living room.

“Leggings,” he said. “You know, those high-waisted athletic ones? I really like them in black, though I'm not exactly picky.” He paused, and his voice practically dropped an octave, as though he was picturing Shay in the very garment he was describing. “I don't know what it is. They just look incredible.”

Shay laughed out loud and began to respond with another voice note. “Well, Julian, you're in luck. My closet is full of leggings, mostly black ones.” Her voice was lightly teasing as she continued. “Who knows, maybe I'll wear some tomorrow.”

His texted reply was quick. “Yes, please.”

Another voice note popped up and Julian's voice rumbled through the air once again. “I could ask you the same question. Is there anything men wear that you really like?” His tone was lightly teasing. “I know you go a little bit wild when you peel my shirt off and I'm standing in front of you in just jeans while you work at my belt, but I'm talking about clothes.”

Shay didn't even have to think before she responded. “Well, you were right about the jeans. The more worn, the better. With a Henley, the sleeves rolled up. The color doesn't matter just so long as the sleeves are rolled up.”

His response was immediate. “Noted,” followed by a winking emoji.

The next night, Shay stood in front of her mirror wearing a pair of leggings from her absolute favorite brand. The fabric was buttery soft and the inky black, high-waisted silhouette hugged every curve from the smallest part of her waist to the tops of her ankles. A slightly oversized, olive-colored sweater, a white strappy bralette from the same brand that made the leggings, and shiny black slip-on sneakers completed the look.

Twenty minutes later, she walked toward his house, where they were planning to meet before heading out for some Mexican food. Julian answered the door at her knock and it was not lost on her that he was wearing a henley with his boots and faded jeans. He had indeed rolled up the sleeves of his black henley to his elbows, and the rest of the fabric strained across his broad shoulders and chest. Shay immediately felt the heat rushing south.

Her clothing apparently had a very similar effect on him, because his heated gaze swept over her as soon as he opened the door, lingering on her lower body. As he stepped aside, Shay walked into the entryway as Julian closed the door behind them.

“Jesus Christ,” he muttered, eyes locked on her hips and thighs.

One corner of Shay’s mouth quirked up in a teasing smile. Spontaneously, she did a little spin so he could get the full view. “These old things?”

Julian didn't respond with words. In one motion, he had stepped forward, pressing his body against Shay's. His kiss was hungry, more insistent than usual. She smiled softly into his lips as his hands drifted immediately to her ass. He groped and squeezed her, massaging her through the buttery soft fabric of her leggings while pulling her snugly against his pelvis. Shay snaked one hand between them and gently rubbed the front of his jeans, delighting in the thick ridge she felt there. As they continued to make out, Julian’s hands repeatedly traveled from the lower part of her ass up to her waist and back again.

She had no idea how much time had passed when Julian finally pulled back, his eyes meeting hers, hands still resting on her waist.

“We should probably try to make our reservation,” he said. His voice was rougher than usual, a sound Shay had come to know well. Earlier that week, they had both decided they wanted to try this new restaurant, which was within walking distance of Julian's house.

“Probably,” Shay replied, although she made no move to step away from him. “We can always have some fun later.”

After another lingering kiss, she bent down to grab her crossbody bag from where it had fallen from her shoulder pretty much immediately upon walking in.

Their booth was tucked near the back of the restaurant, and Julian looked ruggedly handsome beneath the hanging lights that lined the perimeter of the room.

“You know,” Shay said as they waited for their margaritas to arrive, “you kind of undersold the whole leggings thing.”

Julian glanced at her mischievously. “Did I?”

“When I asked you about clothing last night and your answer was leggings, I thought you meant you found them slightly more attractive than other articles of clothing,” she replied. “Not that you were going to look at me like you were about to lose your mind.”

His laugh rumbled from his throat. “In my defense, I didn’t realize how good you were going to look wearing them until you walked up to my door.”

Heat crept into Shay’s cheeks as she met Julian's gaze. Just then, their waiter appeared with frosty margarita glasses. She quickly took a sip of her drink, as though the cold tequila sliding down her throat might help tamp down the arousal still lingering from the intense scene in Julian's foyer. They drank and chatted amiably between bites of chips and salsa. Wanting to steer the conversation into something more appropriate for a public place, Shay asked, “So, how long have you had your truck?”

“Since high school,” Julian responded. “It’s an ‘84. Wasn't even running when I first got it. My dad gave me the truck and a how-to manual for car repairs on my sixteenth birthday.” He smiled. “Some kids get a brand new car, but not in my family.”

“You completely restored a truck just by reading a book?” Shay asked, jaw dropping slightly.

Julian shrugged, taking another sip of his margarita. “Took me forever. My dad helped if something was too complicated.”

“That’s kind of hot. Actually, not kind of. It IS hot.”

He laughed softly. “You think everything I do is hot.”

Shay grinned, raising both hands in mock defense. “You're not wrong.”

A second round of margaritas came at some point during the meal, and they continued talking and laughing. By the time they left the restaurant and began their walk back to Julian's house, the streetlights were on.

The front door had barely closed behind them and Shay had only just taken her shoes off when he grabbed her hand. She instantly shivered at the feeling of his rough palm against her soft skin.

“I'm taking you to bed,” he said simply.

Shay didn't protest.

They walked down the hallway to his bedroom, her hand still in his as he slowly traced circles on her palm with his thumb. She had been to his simple, ranch-style home one other time before tonight and immediately felt comfortable. His bedroom was simple yet tidy, with dark blinds covering the windows and a large bed flanked by a heavy wood headboard.

As they reached his bedroom, Shay gently pulled her hand from Julian's and walked over to the low nightstand, bending over just enough to switch on the flameless candles he kept there. She heard him make a low, satisfied noise, smiling to herself as she turned on the last candle.

When she straightened and turned around, he was on her instantly, his large hands once again finding her ass as their mouths crashed together. Soon, he moved his hands to the hem of her sweater and began to push it up. She let go of his shoulders and raised her arms. He tugged the sweater off the rest of the way and let the light fabric fall to his bedroom floor.

Shay stood in front of him in only her soft white bralette and the now famous black leggings. “I…I should have worn something a little sexier,” she confided, gesturing to the simple bralette.

Julian shook his head. “Now don't get me wrong, I love when you wear lingerie. But this?” He groaned softly, his eyes sweeping down her body once again. “This look gives anything lacy a run for its money.”

She laughed, stepping forward and reaching for the hem of Julian's shirt. Just as she had done, he raised his arms to assist her as she quickly peeled it off. After his shirt had been tossed on the floor, she hooked her thumbs into the thick waistband of her leggings, a question in her eyes.

Closing the distance between them, he rested his hands on her hips and nudged her toward the bed. He swept the quilt back with one hand before beginning to give her gentle orders.

“Keep them on for now,” he said, his familiar, gruffly aroused tone unmistakably returning. “Can I massage you?”

“You don’t have to twist my arm,” Shay joked, turning around and climbing onto the bed on all fours before settling down flat on her stomach, folding her arms and resting her head on them.

She could see Julian from the corner of her eye as he knelt between the V of her still legging-covered legs. Shay sighed, content, as he began to knead her curves. His broad hands charted a slow, intense path over her hips and thighs.

“Jesus,” he muttered. “I swear these leggings were invented specifically to torture me.”

Shay laughed, the sound muffled by her folded arms. “Maybe so.”

His hands lingered over the generous curve of her ass. “You work out,” he observed casually.

“A few times a week,” she admitted. “I walk a lot too. And I do a ton of squats and lunges.”

Julian groaned. “I can tell. You’ve got a great body. Soft and strong in all the right places.”

Shay squirmed, realizing how wet she was. It was beyond arousing to be desired so openly.

Julian apparently registered the slight wiggle of her hips. “Impatient, are we?” he murmured.

She raised her head. “This feels fantastic, but…”

“Tell me what you want, Shay.”

She smiled mischievously. “First, I want you to take your shirt off. After that, I want you to make me feel good. Then I want you inside me.”

The sound that issued from Julian's lips was a half-moan, half-grunt as he rose up. Shay flipped over and looked at his tan form appreciatively from her position. She had barely had a chance to ogle him properly when he planted his lips on hers, giving her one long, devastatingly slow kiss before moving down to kiss her neck. She felt his fervent neck kisses everywhere, but especially in her pussy.

Julian began to nudge the soft cups of Shay's bralette aside so he could lavish attention on one nipple, then the other, alternating hard sucking with slow licks. Her moans began to fill the room and she shamelessly ground her hips against his jean-clad erection.

"Could you…bite them?” Her voice came out more breathless than she had anticipated. “Not hard or anything. I just like having them softly bitten.”

Julian didn't reply verbally, just began scraping his teeth over her right nipple as he rolled the left between two rough fingers.

“Oh, fuck,” Shay moaned. “Fuck, Julian.” Pleasure had overtaken her so thoroughly that she knew she had probably soaked through not only her lace thong, but also her leggings. She was fully bucking her hips against his by this point, and it was as though her heartbeat existed solely in her clit.

Julian raised his head, face flushed, a fire in his eyes. “Will you ride me? In reverse cowgirl?”

The sudden question made Shay smile. It was not lost on her that they hadn't yet tried that position. “I will absolutely ride you. Actually, I brought a couple toys along with some extra condoms. They're in my bag, which I'm pretty sure I left in the front hall. I should go grab-”

Before she could finish the sentence, Julian had gone down the hall to retrieve her bag, handing it to her after striding back across the bedroom. She took it, unzipping it to take out two small drawstring bags and the condoms.

Julian pushed his jeans and boxer briefs down his hips and let them fall to the floor before laying down on his white sheets, a condom in hand. Eyes squarely on Shay, he began to issue orders in a low voice.

“Take off the rest of your clothes. Grab your toy. And then come here.”

Turning around, Shay pulled off her bralette, letting it dangle in her hand for a couple seconds before tossing it to the floor. Then she hooked both thumbs in the waistband of her leggings, arching her back as she began lowering the fabric down over her hips at a torturously slow pace. She was especially teasing as she pushed the soft garment over her ass, back still arched, bending over toward the ground as her leggings finally made their way over her thighs and calves. Still bent over, she stepped out of them fully, now clad in only her red lace thong.

Shay stood and turned, smiling seductively at him as she took one of her toys from its small silk bag and placed it on the bed. He got up off the bed, and, pulling her thong to the side with one hand, first ran a finger over her clit, and then further down.

“Goddamn,” he choked out. “You're always wet for me, but I don't think you've ever been this wet before.”

Speech had left Shay as she panted against his insistent touch. After several more delicious seconds, she suddenly couldn't wait any longer.

“Julian,” she implored breathlessly, “put on a condom and let me ride you.”

He did exactly as she asked and lay back down on the bed as Shay impatiently ripped her underwear off. She mounted him, swinging one leg over his muscular thighs and hovering just above his straining cock. Grasping him with one hand, she guided Julian's crown to her entrance and he began to part her lips.

As she sank fully down onto him, she had the distinct feeling of being impaled, but in the best possible way. Raising her hips, Shay slowly began to bounce up and down on his thick cock.

“Fuck, Shay,” Julian grunted. She felt his hands drift to her hips, clearly needing to both look and touch. They stayed like this for several minutes, with Shay alternating between bouncing and grinding. It was almost like a sexy, hands-on experiment to find out which motion felt the best in this new position.

Shay began bouncing again, and as Julian's cock stroked every part of her, she started to feel an unfamiliar sensation. It wasn't unpleasant, but it was full and sharp. It felt nothing like things usually did when she was getting close to orgasm. Instead, it felt more intense. Her rhythm faltered.

She twisted her head so she could look directly at Julian. Concern immediately crossed his features. “What's wrong?”

Shay bit her lip. “I'm okay. It actually feels really good. It's just…” She swallowed hard. “It suddenly feels like I have to pee.”

Julian gazed at her, a knowing expression on his face.

“Shay,” he said slowly, “I don’t think that’s what’s happening. But we can stop if you want to.”

Shay considered his words, and instead of answering, she turned her head and started riding Julian once again. Before long, that same intense feeling had overtaken her, and instead of pausing again, she simply speared herself on his cock over and over. Her hips picked up speed and her ass bounced as her pleasure climbed higher and higher.

As she rode Julian with the perfect rhythm, it seemed as though all the muscles of her lower body were tensing at once, like a spring coiling tighter. She raised her hips, and as she lowered on his cock once again, a tidal wave of pleasure crashed over her. Thighs shaking, she threw her head back, powerless to do anything but moan through this completely new type of orgasm that she had never felt before. She gradually became aware that in the midst of this incredible feeling, a gigantic gush of liquid had shot out of her pussy and soaked them both.

Once her trembling muscles stilled, she slowly rose off of Julian, rotating around so that she was laying down. She draped one arm over her eyes in embarrassment.

“That hasn't ever happened before,” she said, still in shock. “You might need to change the sheets.” At this, she buried her face in both hands, not looking at Julian.

He softly took one of her wrists, pulling one hand away from her face so that she could see him. He was grinning broadly.

“That…that was one of the hottest things I've ever heard or seen.”

“Seriously?” Shay asked incredulously.

“Seriously. You were so worked up that you squirted all over me, not to mention for the first time ever. How could that not be hot?”

She smiled slyly. “I'm glad you liked what you saw.”

“Shay,” he continued, “that was the kind of thing that I'll probably think about for the rest of my life.”

Letting her eyes flutter closed, she shifted on to one side and pressed her lips to his. This time, she was the one to nudge his mouth open with her tongue. Flames kindled between them once again as Julian swiftly rolled her over, lips still firmly on hers, his cock insistently rigid against her soft inner thigh. They stayed like that for a while, and then he slowly broke the kiss.

“Want to go again?” he murmured into her ear.

“Hell yes.”

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u/WorriedBoysenberry2 — 1 day ago

Her Hookup Era Chapter 3 [F30/M32] [Sex Toy] [Teasing] [Dirty Talk] [Simultaneous Orgasm] [Begging] [Doggy Style]

Chapter 1

Chapter 2

Julian’s hand skimmed Shay’s hip and waist as they lay facing each other, still kissing. She loved how his hands felt on her soft skin, so rough and calloused. The sandpaper-like texture rasping against her sensitive flesh made her whole body sing.

Despite her continued arousal, Shay’s mind began to wander. How should she bring up her favorite toy, the one that lay mere inches away in the top drawer of the bedside table, ensconced in a small bag? Or maybe the better question was whether she should even mention it at all.

Julian must have noticed something shift. He gently unsealed his lips from hers and tilted her chin ever so slightly with his thumb, nudging her to meet his gaze.

"You okay?" he asked.

Shay spoke. “So…I have something I wanted to ask you about. It might be a little awkward.”

He smiled. “After the last half hour, I think we might be past awkward.”

His blue eyes were gentle. Shay took a deep breath. “Okay. I’m just going to say it. The sex we’ve had so far is really hot, but I need really intense, consistent clitoral stimulation to finish. As much as I love penetration, the clitoral stimulation is what pushes me over the edge.”

To her immense surprise, Julian looked curious and open upon hearing this statement. He didn’t look offended. Sulking didn't appear to be imminent.

Emboldened, Shay twisted, opening the drawer and taking out the small silk bag that contained her favorite clitoral suction toy. She wordlessly handed it to Julian. He sat up against the pillows, then hooked a finger into the drawstring at the top and nudged the bag open. He reached inside and pulled out the small pink toy, turning it over once before gazing back down at Shay, that familiar hunger rising in his eyes.

“So,” he asked, “how do you like to use it?”

“Well,” she began, “I’ve mostly used it for,” she paused, as though the words didn’t want to leave her throat, “solo…uh…pleasure.”

Shay didn’t need a mirror to know that her cheeks were flaming. Despite the fact that they had their mouths all over each other that evening, and Julian had been inside her a mere ten minutes before, showing off her toy and then openly admitting to masturbating felt strangely intimate.

Julian chuckled softly. “I assumed that.” He turned the toy over in his hand again, running his thumb over the smooth surface. “But I’m guessing you’re showing it to me because you want to use it together? Incorporate it into sex somehow?”

His tone was even. There wasn’t a hint of insecurity or mocking as he waited for Shay’s answer.

She met his gaze unflinchingly. “Do you really want to hear how I’ve fantasized about using it ever since we first started talking?”

Julian’s reply came out in a low rumble. “Yes, Shay.”

Despite the fact that she was still blushing, she knew she had to share this with Julian. “I want to get on all fours with a couple pillows propping up my chest and hips. I’ll begin using my toy, and you’ll watch for a couple minutes. Then you’ll put a condom on, get on the bed with me, and fuck me senseless from behind while I continue to toy my clit until I cum, screaming, all over your big cock.”

For several seconds, Julian simply stared at her, unblinking. When he finally spoke, his voice was lower, rougher.

“Jesus, Shay,” he said quietly. “Do you have any idea how hot it is when you tell me exactly what you want?” He set the toy carefully beside him on the bed before fisting his cock with one hand.

“Look,” he said, tipping his chin toward his arousal. “I’m dripping precum just from hearing that fantasy.”

“Really?” Shay asked incredulously.

“Shay,” he murmured, “I’m interested in hearing about anything that makes you feel good. And I love it when you talk dirty.”

Shay sat up, smiling impishly as she grabbed two of the pillows that had been under her head seconds before. “In that case, Julian…” she knelt near the end of the bed, sliding the pillows under her chest and hips as she grabbed her toy, looking seductively back at him. Once in position, she arched her back, sliding the toy into place with one hand and pushing the on button. She wiggled it around, working to find the perfect spot. A strangled moan escaped her throat as she fastened it over her aching clit, the suction already pleasantly caressing the tight bud. She moaned again as the toy began to stimulate the exact right spot on her clit.

Groaning, Julian got up from the bed and walked over to the condoms on the dresser, sheathing himself again. She watched him as she continued to use her toy, her breathing growing more heavy as pleasure built. The mattress dipped as he climbed back onto the bed. Shay’s breath caught as he positioned himself behind her, strong hands bracketing her hips. There was the barest brush of his cock ghosting against her entrance before he pulled back.

Julian lowered his mouth to her ear. “Tell me what you want again,” he rasped. “I want to hear you say it.”

Shay’s left hand fisted the sheets beneath her as her right hand continued holding the toy against her clit. The low, teasing suck of the toy combined with Julian’s voice in her ear and his rough, warm hands on her hips made her head spin.

“Right this moment?” she gasped. “I want you to keep talking.”

“I fucking love watching you play with yourself,” Julian whispered back. “You look incredible. And this perfect ass...” He began to move his hands inward from her hips, kneading her ass with his big hands, as he continued to lavish her with compliments and dirty words.

Her arousal ratcheted higher as his rough hands caressed her lush ass cheeks over and over. Despite how sublime everything felt, she suddenly became aware of how utterly empty her pussy was, clenching around nothing. Shay glanced back over her shoulder, her hazel eyes meeting his blue ones.

“Julian,” she demanded softly. “I need you inside me.”

She felt the tip of his cock graze her entrance as he began to thrust inside her, agonizingly slowly. She could have sworn that he was even harder than the first time. Shay whimpered at his slow pace, a high-pitched moan conveying her frustration.

“What’s wrong?” he asked, his voice sounding almost strangled.

“I…” she said, still whimpering. “I don’t want it soft or slow this time. Julian, I want to be fucked.”

Suddenly, her pussy was empty again. Frustrated, she twisted around again, inadvertently staring daggers at him.

“Well?” she implored, impatience saturating the single word.

He knelt just behind her, fisting his cock with one hand. A wicked grin crept over his lips.

“It’s kind of a turn-on when you’re bossy like this, you know,” he said playfully. “Shay the Dom.”

“It would be even more of a turn-on if you would just take me from behind,” she grumbled.

Suddenly, she felt Julian move behind her, his hands settling on her hips once again.

“You really want me to fuck you hard?” he implored, still teasing her entrance with his cock. “You want it hard and fast?”

“YES!” Shay cried. “Yes! Julian, I need you to fuck me. Hard.” The words tumbled out before she could stop them, and she realized she would say anything she needed to. “I’m begging. I want to feel it tomorrow. I don’t care if I have to ice my pussy. Just please give it to me. Fuck, I don’t know what else to say. I just need you to fuck me. Please, Julian!”

He chuckled darkly and she let out another noise in response, this one a high-pitched whine.

“Okay,” he replied. “Since you asked so nicely.”

Shay was dimly aware that the neighbors could probably hear her cry out as Julian entered her with one long, brutal thrust. Actually, there was no maybe or probably. They had definitely heard that.

But the pleasure from suddenly getting what she wanted was so thoroughly consuming that she didn’t care. She could practically feel Julian's length in her stomach as her toy continued to hum and suck at her clit. His balls slapped against her as he set an almost punishing pace, pleasuring her exactly the way she had asked and driving into her pussy so hard that she knew without a doubt that she would feel it tomorrow. Speech gave way to moans and cries as Shay took everything Julian was giving.

Several minutes passed just like this. Suddenly, Julian changed motion, still fucking her as intensely as she had asked, or rather, begged for. But now he began dragging his cock almost all the way out of Shay's dripping pussy before slamming back in, and pausing ever so slightly before deliciously repeating the motion over and over and over. “Fuck, Julian,” she moaned appreciatively. A few thrusts like this were causing the tension inside her to build to a crescendo.

“Don't stop,” she choked out. “Just like that.” In response, Julian didn't change a thing about his thrusts or his pace. She felt herself beginning to tighten even more around his cock.

“Julian, I…” She found she could barely get the words out.

“Yes, Shay?” he asked, almost innocently. She had no idea how he could sound so composed when she was practically unraveling with each long, brutal stroke of his magnificent cock.

“I’m close,” she rasped. “I’m so fucking close.” She pressed another button on her toy, kicking the suction up even higher.

That little bit of extra suction was all she needed. “Oh, fuck!” she moaned. “Fuck, Julian, I’m going to cum!”

Julian didn’t speak, but the sound he made sounded like a growl. Shay began to unravel as waves of white hot pleasure cloaked her mind and body. Her pussy began to rhythmically squeeze Julian’s cock as her clit pulsed in ecstasy, her internal muscles grabbing onto him so intensely that his thrusts abruptly slowed. She continued crying out in pleasure through her orgasm and the aftershocks. Through the haze of one of the most intense orgasms she had ever experienced, she was dimly aware of Julian’s grip tightening on her hips and his cock pulsing as he roared, orgasming along with her, filling the condom.

Turning off her toy, she placed it to the side before falling forward on the pillows, no longer able to stay upright fully upright. Julian pulled out of her, gripping the base of the condom, as he collapsed alongside her.

Their bodies were both slick with sweat. Neither of them spoke as they both attempted to catch their breath and their bearings. As Julian gradually moved to dispose of the condom, Shay grabbed the pillows that had been propping her up moments before and moved them back to the head of the bed. She lay down on her side, and Julian stretched out behind her, draping one arm over her hip.

“I think,” he announced, his voice slightly muffled by her hair, “you’re trying to kill me.”

Shay laughed brightly. “No, I just want to come all over you.”

Turning her head slightly, she glanced behind her at his mussed hair and the thin sheen of sweat he wore. She also couldn't help but notice that his neck and chest were still flushed with arousal. Before Shay could get too caught up in how sexy Julian looked, her stomach rumbled loudly, clearly audible in the quiet room.

The silence that followed her protesting stomach lasted approximately half a second before Julian laughed.

“Ugh!” Shay groaned, turning and burying her face in the pillow.

“Someone’s hungry,” he teased.

“Maybe not so much hungry as humiliated.”

“You shouldn't be embarrassed.” He pushed himself up on one arm, smiling down at her. “Sex like what we just had tends to burn a lot of calories.”

Julian got off the bed and bent down, reaching for his jeans and boxer briefs where they lay discarded on the floor. Shay shamelessly and openly ogled his perfect ass before he began to put his boxer briefs back on.

Before she could get too lost in this reverie, she jerked her gaze from Julian's broad, muscular back and made her way over to the ensuite bathroom. “Be right back,” she called before closing the door softly behind her. Although she was still currently in a kind of sex haze, she didn't want to get a UTI.

When she was done, she walked back into the bedroom and toward the lounge chair in the corner. Rifling through a small pile of clothes draped over the back of it, she found the oversized linen button-down she had been looking for. Despite how tall she was, the hem reached mid thigh, and she didn't bother with underwear. Thinking quickly, she grabbed her phone from the bedside table and tapped out a rapid fire text to both of her friends, letting them know how well the evening was going, before following Julian and his now jean-clad form out of her bedroom.

He headed straight for the kitchen island, where the abandoned takeout bag sat. She took a seat on one of the tall bar stools flanking the kitchen island as Julian opened the bag and began to take out wrapped tacos, small containers of salsa, and bags of tortilla chips. A few minutes later, they were both chewing happily as music from a small speaker hummed gently in the background. Shay tucked one leg beneath herself as she perched on the bar stool, eyeing Julian's shirtless form across from her. The muscles in his tan forearms bunched and fanned as he lifted a taco to his mouth.

She was suddenly very happy that he had only put his jeans back on. Who needed shirts, especially when you looked like him?

Just then, Julian looked up, his eyes meeting hers.

“What?” she asked slyly.

“Oh, nothing,” he replied. “You just look really sexy."

“Funny you should say that. You do too."

He laughed, the hearty sound filling the room.

After a moment, he continued. “You have no idea how hard it was to focus on anything from the second you met me at my truck.” His voice may have been softer, but his eyes practically burned as he gazed at Shay.

“And then when you led me to the bedroom and slowly started taking off your clothes, and I saw what you had really worn for me…well, I was done for. It's truly a miracle I lasted as long as I did that first round.”

At this, Shay felt tendrils of arousal blooming in her belly for the third time that night.

Julian took a breath, as though composing himself. “And the second time? Watching you use your toy to make yourself feel good? The way you begged for what you wanted? Those sounds you made? The feeling of you coming apart around my cock?”

She felt like she had been running and was gasping for air, even though she was still just sitting there on the bar stool.

“Julian…” she said breathlessly.

He stood up, rounding the kitchen island and standing squarely in front of her bar stool. Shay instinctively rotated around in her seat, facing him. Standing between her knees, he took her head in his hands and bent down to kiss Shay deeply.

She sighed into his mouth with a mix of contentment and arousal. It was going to be a long night.

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u/WorriedBoysenberry2 — 8 days ago

Her Hookup Era Chapter 2 [F30/M32] [Casual Sex] [Oral] [Dirty Talk] [Cum on Body] [First Time Together] [Lingerie] [Missionary]

Chapter 1

Shay stood in front of her heavy wooden dresser, surveying the neat stacks of lingerie in the top drawer. Most of this drawer consisted of rather plain bras and panties, mostly in shades of black, blue, and nude. However, the right side of the drawer was home to her more risque choices and she knew she would find her attire for tomorrow over here, among the lace, mesh, and silk.

She rifled through the soft fabrics, glancing at each garment, with colors ranging from magenta and light blue to black and even white. Feeling inspired, she picked up a black push-up bra with fishnet detailing across the cups, then rooted through the drawer again until she found the perfect match, a high-waisted black lace thong. Black lingerie always made her feel sexy and it had the added bonus of suiting her pale skin and chestnut hair very well. She placed both on top of the dresser and smiled, anticipation thrumming within her whole body.

Shay had let two of her close friends know what was going to happen with Julian tomorrow night. They both had seen the tumultuous end of her relationship and difficult breakup firsthand, and they each seemed happy for her that she was pursuing something fun and pleasurable. She also felt safe around Julian already, but one could never be too careful, and so she wanted her friends to know about this new man in her life and had also promised to check in with them tomorrow night.

Later that evening, Shay lay sprawled on her couch with an icy glass of sparkling water and her phone. A small smile played across her lips as she and Julian exchanged messages.

They had continued sexting since their pizza lunch, but the sexy messages were also interspersed with simple questions about the other person's day. It was obvious that neither of them viewed the other as just a warm body, despite their casual arrangement.

Suddenly, her phone pinged with a voice note from him and Shay quickly tapped play, wondering what he had to say. Julian's deep voice proceeded to rumble through her phone speakers.

“So, I know I told you that I've been separated for a while and am getting divorced,” he began. “Even before the separation, we were more like roommates. It was effectively a dead bedroom for a long time, so I haven't had sex in close to a year. I probably won't last very long the first time.” He paused, taking a breath. “I just wanted to ask for your patience and give you a heads up.”

After it was over, Shay listened to the voice note a second time. She felt completely unfazed by everything Julian had shared. In fact, until receiving this voice note, she had seen him as a man who was almost unfairly handsome, not to mention supremely confident. What he had shared with her made him seem a little more human, and that was downright hot.

“Thank you for telling me,” she texted him. “And honestly? There's always round two.” She followed this last sentence with a winking emoji.

“You better believe there will definitely be at least two rounds,” Julian texted back.

The next day, Shay could barely keep her mind on work. As she sent emails and sat through virtual meetings, her mind kept wandering to Julian's arrival. After work was done for the day, she took a quick shower, washing off the day with vanilla-scented body wash. After toweling off, she applied some body oil to her arms and legs. After adding some quick makeup, she walked into her bedroom and began to put on her lingerie. Since she had to meet Julian in the visitor area of the apartment parking lot, she also put on a soft magenta-colored skirt that came to mid-thigh, with a silky black sleeveless top tucked into it. Sliding on a pair of sandals, she glanced at the time on her phone and realized he was nearly due at her apartment.

Julian had told her the night before that he would bring takeout and condoms. Shay appreciated the gesture of him picking up some dinner for them both, but she also had to admit that her mind wasn't exactly on food.

What she was most hungry for was Julian, and she had a feeling that multiple condoms would be used before either of them so much as looked at the food containers.

Shay strode outside toward visitor parking, spotting Julian's truck right away. He hopped down from the cab, a plastic bag in hand, as he waved at her. When they reached each other, he hugged her with his free arm, briefly pressing her against his body. She returned the hug, relishing the warmth of his skin through his soft t-shirt.

He smiled broadly, slightly lifting the bag. “I come bearing tacos. And responsible decisions.”

Shay chuckled lightly, thanking him.

As they began the walk to her apartment, she continued. “I have to be honest. I've been looking forward to this all day. Actually, all week.”

He smiled at her, his look friendly but with an undeniable heat in his eyes. “Believe me, I have too.”

Julian and Shay made their way through the parking lot and toward her unit, and she noticed the heavy sound of his boots on the sidewalk. He smelled wonderful, like soap and a hint of cedar. She guessed that he had showered after work, just like she had. His arm brushed hers once or twice, and she felt a jolt go through her.

The pair reached Shay's apartment door, and she quickly unlocked it, stepping aside to let him in. Julian took a couple steps toward the kitchen island and set the bag down as she closed and locked the door behind them.

Neither of them said a word.

Suddenly, it was as though they had been catapulted at each other. Julian grasped Shay's face in his big hands as he sealed his mouth to hers. As their tongues danced, she noticed that he tasted like mint. She snaked her arms over his shoulders, the warmth of his body radiating through his shirt as her hands rested behind his broad back.

As they kissed like their lives depended on it, Julian pressed his pelvis against Shay’s. Their bodies melded together, and she couldn't help but notice the thick bulge in his jeans. She couldn't be 100% sure with that layer of denim in the way, but she was pretty sure he was already fully hard.

Although it almost pained her to do so, Shay pulled her lips from Julian's. When she spoke, her voice came out with a much higher pitch than she expected. “Do you want to go to the bedroom?”

“Yes,” he answered simply, voice rough. Reaching down, he toed his boots off, the movements almost awkward in their haste. Then he reached into the bag on the kitchen island and grabbed the box of condoms. Shay’s core clenched in anticipation at the mere sight of this box as she slid her sandals off, leaving them next to Julian's boots before turning and leading the way down the hall to her bedroom.

She had closed the curtains and put fresh sheets on the bed in anticipation of tonight. The sheets were black, which felt far more appropriate for the occasion than her usual gray cotton. The room was lit by a single lamp on the bedside table, casting the space in a soft amber glow.

As the two entered the bedroom, Shay turned to face Julian, taking two steps back. He placed the condoms on the dresser before remaining rooted to the spot. Maintaining eye contact, she tugged the hem of her black silky top free of her skirt, gently pulling it over her head before dropping it to the floor. She then hooked both thumbs in the waistband of her skirt, pushing it down over her hips and letting it pool at her feet. Her eyes didn't leave Julian's the entire time and she could see the unrestrained lust flaring in his gaze. Shay knew that the thong she wore framed her hips and waist perfectly, and her generous breasts strained against the silky black fabric of the bra.

Julian took two steps forward and pulled Shay to him, searing his lips to hers once again as his hands immediately found the lush globes of her ass. He palmed her flesh in his hands as their kissing intensified. Shay realized she was grinding her hips against Julian's without even thinking about it. Suddenly, a moan vibrated from deep within her, shattering the silence of the room.

At the sound of Shay’s throaty moan, it was as though Julian's remaining composure snapped. He broke the kiss, gently walking Shay back toward the king size bed until the backs of her legs collided with it. She laid down, her knees hanging off the edge. Julian knelt down in front of her, still fully clothed. In what felt like one motion, he hooked her thong aside with one finger, then began a heated trail of kisses down the swell of her stomach before swirling his tongue around Shay's swollen clit. Immediately, she began moaning and whimpering against Julian's insistent mouth.

He briefly raised his head, his eyes meeting Shay's. “You're soaked for me. So fucking hot.” He lowered his tongue to her clit once again, alternating between deliciously slow sucking and faster swirling.

With these dirty words, she couldn't stand it anymore. Julian's oral skills were clearly amazing, but Shay was overcome by a desperate need. "This feels amazing and you have a magic tongue," she moaned, "but I need your cock."

Julian stood up, a wicked grin spreading across his chiseled features as he peeled off his shirt and tossed it aside, exposing the tan, solid expanse of his torso. Shay’s eyes snagged on a small thatch of hair over his sternum and then a second, smaller trail that disappeared into his jeans. She couldn’t get too distracted by his sexy body hair, however, because he then made quick work of his belt before pushing his jeans and boxers down in one motion.

Shay’s eyes grew wide as Julian’s cock bounced out of his pants as though it was on a spring. As her brain caught up with her eyes, she realized that the Snapchat pictures he had sent simply didn't do him justice. His cock jutted out toward her, long, girthy, and hard as stone.

Sitting up, Shay moved closer to him, grasping his thick shaft in one hand as she lowered her mouth over the tip, tasting the salty precum that had collected there. Within a few seconds, she realized that his girth required two hands as she slowly began to stroke him while still sucking the head of his cock. She kept her eyes on his the whole time.

Julian moaned, the deep sounds almost guttural. After a couple minutes, he gently pulled his cock from Shay's lips as he spoke. “That feels incredible, but I don't want to come yet.” She pushed the comforter down toward the foot of the bed and lay back on the satin sheets, propped up against the pillows. Her eyes appreciatively drifted down to Julian's firm ass as he turned toward the dresser, grabbing a condom from the box and tearing the gold foil open before rolling it over his straining cock. His hurried movements betrayed just how eager he was to join Shay on the bed. As he worked, Shay pushed her thong down her legs, then tossed it to the side. She did the same with her bra, reaching behind her back to undo the hooks and sliding it down her arms before putting it beside her discarded underwear.

Julian's blue eyes locked on to Shay's, and they widened as he registered that she was now fully naked. He was on the bed in what seemed like two strides. She spread her knees as he lowered himself on top of her, his sheathed cock resting against her soft belly as their mouths crashed together once again. Shay reached for his cock, pulling her lips from his.

“Can I?” she asked, grasping his cock with one hand. It was not lost on her that her fingers didn't wrap all the way around. His eyes practically seared hers as he nodded, almost gravely. Shay guided Julian's tip to the seam of her pussy, and he bucked his hips forward slightly so that he could give them what they both wanted so badly.

They each moaned loudly as he thrust into Shay, one agonizingly slow inch at a time. It almost felt like Julian’s cock was splitting her open, stretching her pussy as far as it could possibly go. As he worked his way inside her, she knew that his cock was the biggest she had ever had, and she felt herself getting even wetter. Soon, he was inside her to the hilt, his pubic bone against her clit. He buried his face in her neck as he sucked and kissed the sensitive skin there. Shay began to softly buck her hips, but Julian remained still.

“I need a minute,” he said gruffly. Shay stilled her hips, enjoying the sensation of Julian's mouth on her neck. She wasn't sure how much time had passed before he began to move, slowly at first, fucking Shay with languorous thrusts. Moans and frantic cries bubbled up from deep within, but she was too lost in the pleasure to know or care exactly what she was saying.

Abruptly, Julian's thrusts began to slow and Shay suddenly felt incredibly empty as he slid out of her, kneeling on the bed, grasping the base of his cock firmly. She whimpered in protest.

Julian smiled down at her. “Honestly, Shay? You're so fucking tight,” he said. “I know I told you that the first time probably wouldn't last too long, but I also don't want to utterly humiliate myself.”

She smiled back, pussy pulsing and clenching as though he was still inside her. “You don’t need to worry,” she said gently. “I’m enjoying myself. And I want you to enjoy yourself as well.” She reached out, grasping his wrist while meeting his eyes. “Now come here. I’m not done with you yet.”

After several more seconds, Julian settled back on top of her, bracketing her spread thighs with his knees, as he lowered his mouth to hers. Just like a few minutes before, she reached for his condom-covered cock to guide him inside her, and he took his time burying himself deep inside her throbbing pussy for the second time. He made a strangled sound as he began to work himself in and out of her. As he gained a steady rhythm, she raised her hips to meet his, beginning to rotate her pelvis in small circles.

Julian let out what sounded like a strangled wail. “Shay,” he ground out. “I’m getting close.” At this, she began to move faster, wanting him to feel the same pleasure he was currently giving her.

Suddenly, Julian pulled his cock free of Shay’s pussy once again, yanking the condom off in one lightning-quick movement before leaning forward and roughly stroking his cock once, twice, then three times. At the beginning of the fourth stroke, his cock began to erupt, his eyes fluttering closed as ropes of his cum landed on her soft belly. Her mouth opened slightly at the wonder of this erotic sight, and she glanced down at his swollen cock then back up at his face, his eyes still half-closed in pleasure.

Julian moved to Shay’s right before collapsing beside her, still breathing heavily. She grabbed a tissue from the bedside table and gingerly wiped his cum off her belly, then dropped it into the small trash can next to the bed. Shay turned on her side to face Julian, sealing her lips to his. Facing each other, it was as though their bodies were drawn like magnets and they were soon pressed fully against each other. Disbelief entered Shay’s mind as she realized that Julian’s still-hard cock was jutting, rather insistently, into her belly. Pulling her hips back slightly, she briefly gazed down at his erection, and then back up into his eyes, her mouth open in surprise.

“How are you still hard after an orgasm like that?” she asked incredulously.

Julian’s laugh rumbled into her ear as the faintest blush stained his cheeks.

“We did allude to the fact that there might be two rounds,” he said slyly. With that, he leaned in and kissed her.

Shay's eyes slowly fluttered closed as she once again became utterly lost in pleasure.

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u/WorriedBoysenberry2 — 9 days ago
▲ 23 r/Erotica

Her Hookup Era Chapter 1 [F30/M32] [FWB] [Making Out] [Big Dick] [Sexual Exploration] [Sexting]

Shay had been single for three months.

Breaking up with her ex had been, by far, one of the best decisions she had ever made. Her life was peaceful now. She didn't have to deal with constant arguments or fighting well into the early morning hours. His tantrums and yelling would now be a thing of the past. For good.

She also didn't have to deal with his erectile dysfunction any longer. Shay knew that this was something many men struggled with. She never would have dreamed of shaming him for it. But the fact remained that her ex had been in denial. He had absolutely refused to see a doctor. Instead of seeking real solutions, he would blame her quite openly, claiming that he didn't need medical care and that if Shay would simply try harder to emulate the actresses in his favorite porn movies, the problem would vanish.

Shay shook her head, still in utter disbelief at her ex's rationalizations, as she made an account on a popular dating app known for hookups. She didn't really know why it had taken her so long. She had been on exactly two dates since the breakup but there hadn't really been a connection with either man. Today, she was finally being honest with herself.

What Shay really wanted was to be fucked. Preferably on a consistent basis and ideally by a guy with a nice, big cock.

She posted a few pictures, inviting and sensual but not so extreme as to get her banned from the app. The pictures were ones that clearly revealed her body in all its glory. She was tall and thick, with long legs, wide hips, a round ass, and large breasts. She was active and went to the gym regularly, but her body had always naturally been more curvy, and no one could ever accurately describe her as thin. It was important to her that she find a casual partner who not only appreciated her body just the way it was, but liked thick women specifically.

She kept her profile simple, stating plainly about being recently single and wanting some casual fun with someone open-minded and hung. She hesitated a bit before adding the last line, but then typed it with purpose.

I have HSV-2. Looking for someone either also with HSV-2 or who is negative, but educated and accepting.

Though this diagnosis had been relatively minor in Shay's life over the last five years, she found herself wanting to be completely transparent about it, especially when looking for a casual sex partner. She knew it was a dealbreaker for some, and this last line of her profile would serve as a way to filter out those particular folks.

Soon, Shay had more messages than she could possibly respond to. She scrolled through them, deciding who might merit a reply, when she saw a message that contained more than the usual "hey."

"I know you're probably getting a ton of messages right now, but I liked your photos and wanted to reach out. I'm going through a divorce and am interested in finding an FWB. My size is decent and I love giving oral. Oh, and I also have HSV-2."

Shay didn't waste any time and immediately opened his profile. His name was Julian and he was 32 years old to her 30. He was blond and blue-eyed, with a chiseled jaw and tan skin. Most of his photos were outdoors and he wore an easy, laidback smile in most of them that instantly drew her in.

Intrigued, she quickly tapped out a reply, and before long, the two were quickly messaging back and forth. After some small talk, Julian asked Shay if she wanted to exchange Snapchats. She agreed immediately and, once on Snapchat, their messages quickly grew more carnal. She was already excited about this new connection, but when Julian asked her if she would like to see his cock, she didn't need to think twice. As soon as she opened the picture, she saw that her new potential casual partner had been very modest indeed when he described his cock size as "decent." The cock she saw on her phone screen was enormous. He looked to be around 8 or 9 inches, thick, and crowned with a deliciously bulbous head. Shay felt herself growing aroused and she was relieved she had chosen well by responding to his message.

Shay already wanted this man, but she also knew she had to vet Julian in person first. She suggested meeting for lunch and he enthusiastically agreed. They decided on a pizza place convenient to both of them and picked a day and time.

That afternoon, Shay was both excited and nervous as she changed into a pencil skirt and flowy black top that nicely emphasized her figure. She slid on some low heels and grabbed her bag before she could let her nerves get the better of her.

As soon as she walked into the pizza restaurant, she saw him. Julian's blond hair curled out from under the edges of his baseball cap, which he removed as she walked toward the table. He wore a T-shirt and jeans that fitted him perfectly, his clothes showing off strength and muscles that likely hadn't come from a gym, but from working with his hands. Worn work boots completed the outfit, and she felt a zing of arousal at how down to earth he looked. Most of her exes had white collar jobs, and she suddenly realized there was something very sexy about a man who was a welder.

As she walked toward him, his eyes traveled all the way from her long, shiny brown hair down to her heels, and she was pretty sure that she wasn't imagining an appreciative look in his eyes that immediately indicated he liked what he saw.

"Hi," he said simply, smiling at her.

"Hi," she responded brightly, anticipation and the first hints of arousal swirling together in her stomach.

After briefly glancing at their menus, Shay and Julian decided to share a pepperoni pizza, and they kept their conversation appropriate for a public place as they made more small talk. Nevertheless, she could feel the unspoken sexual tension growing deliciously between them.

The two finished eating, and the waitress walked by, placing the check on the table. Shay reached for her purse on the chair beside her but Julian gave her a small smile and shook his head.

"Your money's no good here," he joked as he took out his credit card. She blushed a little bit, pleased. Her ex always insisted that they split the bill. Julian's chivalry was not going to go unnoticed.

After he paid, they stood up and slowly made their way out to the parking lot. As they walked, he rested a hand gently on her lower back, and Shay shivered with delight. It turned out they had parked near each other, and they stood for a couple minutes near both of their cars, talking more.

Suddenly, Julian stopped, his gaze dropping down to Shay's plush, glossy lips. Her heart pounded as she stared at his handsome face. Wordlessly, she took one step toward him, closing any distance left. Silently, they looked into each other's eyes for several long seconds before Julian leaned forward, wrapped his hand around the back of Shay's head, and crushed his mouth to hers, his tongue instantly nudging her soft lips open.

She instantly regretted her choice of low heels as her knees wobbled. Their tongues battled as each kiss became deeper and more intense. His lips were full and insistent as he continued kissing her passionately, neither caring that they were in the middle of a parking lot in broad daylight. Julian's hand drifted from the back of her head, skimming her spine, before resting on her lower back. He lightly pressed his hips against hers, and she could feel his gigantic erection straining against his faded jeans.

Shay could feel that her black lace panties were already damp. If she was this wet from a simple parking lot makeout, what would it be like when she was actually in bed with him?

Suddenly, voices drifted across the parking lot, coming from the direction of the restaurant, and they pulled apart as if synchronized. They were both breathing hard, lips swollen. Julian's blue eyes were wild and he subtly reached down, adjusting himself discreetly.

Shay sighed. "I wish I could take you home with me right now. But I have to get back to work."

"I do too," Julian agreed. "But let's meet up again soon. Real soon."

Half an hour hadn't even passed after their lunch date when Julian and Shay began texting about how much they enjoyed lunch and were incredibly turned on by each other. Julian also sent her another Snapchat photo that he had taken shortly after they had parted ways, so she could see exactly what their little makeout session had done to him. They didn't want to waste any time and decided to meet two days later.

Shay couldn't wait.

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u/WorriedBoysenberry2 — 10 days ago