A College Cuckolding - Part 1

"Do you masturbate?"

Chloe rolled onto her side and rested her hand on Owen's chest. She ran her fingers over the soft fabric of his t-shirt and stared for a few seconds until he turned towards her.

"Yes," she answered.

A look washed across his face. It was gone just as quickly as it had appeared, but Chloe was fairly certain it was just a touch of insecurity she'd seen. She wasn't entirely sure why her boyfriend would be threatened by something as innocent as her masturbating, but it seemed to be the case.

"Why do you ask?"

"I...I don't know," he said. "I was just wondering, I guess."

"Does it surprise you that I masturbate?" Chloe asked. She was Owen's first serious girlfriend - and the first girl he'd had sex with - so it wouldn't have surprised Chloe if he was, in fact, surprised that girls masturbated.

He looked a little embarrassed. "I...I guess if I'm being totally honest, yes, for some reason I do feel a little surprised."

Chloe couldn't help but smile, mostly at her boyfriend's naiveté when it came to women. They'd been together for nearly three months - they'd met during freshman orientation and hit it off right away - and yet he still always seemed amazed that she actually liked having sex.

"Girls are different than guys," she said, "but we still get horny. Maybe not as horny as you do, but some of us actually do get as horny as guys."

Owen looked at her with a mixture of excitement and wonder in his eyes. "Are you one of those girls?"

Chloe smiled and nodded. "Given how often we have sex, does that surprise you?"

He shook his head. "No. I guess that's why I was surprised you masturbate, though. I mean, I don't really masturbate anymore because we have sex so often."

It was Chloe's turn to be surprised. "Really?"

"Yeah, really. Maybe once every two weeks. I suppose having roommates makes it a little harder, though, and you have the benefit of being in a single room," he said.

She smiled and kissed his neck softly. "You benefit from that too, don't you?"

They almost always had sex in Chloe's room. Owen was in a triple, which meant one of his roommates was almost always there and it was so much easier just to go to her dorm instead of negotiating with his roommates for a little private time in the room.

"You're right, I do benefit from that," he replied with a smile.

Chloe's hand moved down his chest and between his legs. She massaged her boyfriend's cock through his pants and moaned softly while showering his neck in tender kisses. He got hard almost immediately, a fact that bolstered her confidence and put a smile on her face.

"How often do you masturbate?" he asked.

Chloe was surprised at the annoyance she felt. She thought she was being rather obvious about what she wanted, but it seemed that Owen had other things in mind.

"Well, I don't have a set schedule, but four or five times a week, I'd say. Sometimes more, sometimes less," she answered.

Owen's eyes went wide. She'd clearly surprised him.

Chloe suddenly felt defensive. "Is that a problem?"

He shook his head. "No, no, not at all. It's, it was just surprising, that's all."

It seemed like it was more than surprising, at least based on the look on his face. "Are you sure that's it? Because it seems like there's something else."

"No, really, it was just kind of surprising."

Chloe probably should have let it go, but a mild sense of annoyance had overtaken her and she wasn't in the mood to just let it pass. "It's pretty clear that you're bothered by something, Owen. So what is it? Do you think I'm some kind of freak for masturbating that often?"

"No, no, it's not that at all. It really isn't. It's not about you. It's just...I just...okay, honestly, I'm really sorry, but I just kind of got a little sidetracked in wondering if there's something about me or the sex we have that makes it so you need to masturbate. You know, like, am I not satisfying you?"

Chloe's annoyance washed away as Owen displayed a kind of vulnerability few college freshmen - at least based on Chloe's limited experience and the experience of her friends - were willing to show.

"Oh, no, it's not about that," she said. "I've just always had a really high sex drive. From the first time I had an orgasm it was like I was off and running. I honestly can't remember the last time I went more than two days without an orgasm, and I usually don't go more than a day, and if I'm being honest, there are lots of days where I cum more than once."

Chloe was surprised that she found Owen so utterly adorable - almost irresistibly so - as he got caught up in his insecurity. She got on top of him, leaned down, and kissed him softly. She parted her lips and though it took a moment, Owen eventually did the same. She moved her hips back and forth over his crotch and slipped her tongue into his mouth. Owen's hands moved down her back and grabbed Chloe's ass, squeezing it tightly as she moaned, in part because it felt good and in part because she loved that his dick well on its way to a full, throbbing erection.

"I always cum when we fuck, Owen," she explained softly. "Always. You know I do. I've never faked an orgasm with you. I'm not that kind of girl."

He scanned her face like he was searching for signs of deception on her part and then said, "I know. I believe you. I do. I just...I don't know, I just want to be good at...well, to be good at fucking you."

Chloe sat up and laughed. "You are, Owen. I promise. You are. Why would I still be with you if you weren't? There are tons of guys at this school. Like, there are literally thousands of guys to choose from. I get asked out all the time, in fact, so it's not like I'm just staying with you because there are no better options out there."

Chloe instantly regretted mentioning the fact that other guys asked her out, especially given Owen's mild insecurities. She expected her slip of the tongue would only deepen those feelings, but instead something else happened. A look of intense lust briefly flashed across Owen's face and his hips pushed upwards his cock had expressed an involuntary desire to be inside her.

The look of insecurity came immediately after the lust, leaving Chloe a little confused as she sat astride her boyfriend. For a few seconds Owen said nothing at all and he couldn't bring himself to look at her. It wasn't anger or annoyance or even insecurity that seemed to keep his gaze away from hers, though. Instead, Chloe was certain her boyfriend was embarrassed.

"What's wrong?" she asked.

He shook his head. "Nothing. Nothing's wrong. I just didn't...I mean, it's not like you can control other guys asking you out and it's not like I should actually care about that since I know you turn them down."

"I do. Each and every time," she replied.

"But I didn't know that other guys were so interested in you," he continued. "And it feels...well, I don't really know how it feels. Weird, I guess."

He still struggled to look at her for more than a few moments, furthering Chloe's belief that Owen was struggling with his feelings and perhaps experiencing an unexpected sense of embarrassment.

Though some part of her knew that it was wise to just move on from the topic, Chloe couldn't help but want to explore the lust she'd seen on Owen's face. It felt like an irresistible mystery and her sense of intrigue made it impossible to do the smart thing and refuse to tug at that particular thread.

"Someone asked me out today," she said.

Owen looked at her for a moment and his eyes went wide before he looked away. Chloe saw the briefest flash of lust, though. He was turned on. It wasn't the only thing he felt, but there was no question Owen was turned on.

"He's on the football team, actually," she continued. "He was walking with some of his teammates and he broke away from them to talk to me. I figured he'd be the typical meathead type and act like it was an absolute privilege to go on a date with him, but he was actually a lot sweeter than I expected."

Owen kept glancing at her, but he refused to make eye contact for more than a few moments as Chloe relayed her story. The lust was there, though. It was joined by what looked like anxiety and a touch of that same embarrassment, and though Chloe knew it was potentially unkind to keep pushing, something inside her refused to relent.

"He talked to me the entire way to my class," she continued. "Though I guess it's more accurate to say that he was flirting with me. He was good at it, too. He found a handful of ways to tell me I was beautiful without actually using the word and not once did he act like he was god's gift to women."

The mention of flirting elicited a moan that Owen tried his best to choke off. Chloe felt his hips move subtly, too, like they were trying to thrust and Owen was trying his best to control them. She responded by resting her hands on his chest, smiling, and slowly grinding her crotch over his.

"It wasn't until we got to my class that he actually asked me out," she said. "He said he and his friends were going to a frat party this weekend and he'd love it if I'd join him, that he guaranteed I'd have a good time."

Owen was hard as a rock and his complete unwillingness to look up at Chloe seemingly confirmed that he was both uncomfortable and more than a little embarrassed at his erection. He didn't move to stop her from dry humping him, though, and the growing heat of arousal between her legs meant that Chloe had little interest in ceasing the exploration of her newfound - and surprisingly erotic - fascination.

"It happens almost every day, you know," Chloe continued. "I guess I'm approachable. I don't know. It seems like guys just can't help themselves. They just want to go out with me, Owen."

She took her t-shirt off and tossed it on the floor. Owen stared at her breasts as Chloe reached back to unhook her bra. It fell to the floor just like her shirt and she took his hands and placed them on her soft, perky flesh.

"Does it turn you on to think about other guys asking me out, Owen?" she asked.

He shook his head but his cock remained stiff and he continued to play with her tits in a manner that felt magnificent. Chloe placed her hands over his, closed her eyes, and unleashed a long, low moan while moving her hips even faster over his crotch.

"It's okay if it does," she said. "I promise, I won't think it's weird. I really won't. There's something kind of...I don't know, exciting about it, if I'm being honest."

"Really?"

Chloe opened her eyes and looked down at her boyfriend. She saw the vulnerability in his eyes. She saw the desire, too, but it wasn't lust. It was a desire to share with her, to open up, to be completely honest.

Chloe took her hands from his breasts, leaned down, and kissed him softly. "I'm turned on, Owen. My pussy is wet. My nipples are hard. I'm excited by your excitement, assuming I'm right about what you're feeling."

"I...I don't understand it," he said.

Chloe kissed his neck and moaned. "You don't have to," she whispered. "Who cares about understanding it? Why not just enjoy it?"

She crawled back until she was between Owen's legs and removed his pants and underwear, freeing his stiff cock. Chloe wrapped her fingers around it and stroked him slowly as she leaned down to kiss his thighs. She let her lips linger against his flesh and used her tongue to provide a little extra pleasure while his dick throbbed in her hand.

"Fuck, that feels so good," he said.

Chloe sat up with a smile and took her pants off. Her panties followed and she crawled into her bed once more. She straddled her boyfriend and took him inside her. Owen's eyes went wide and she smiled.

"Can you feel how wet I am?" she asked.

He nodded vigorously and smiled.

"I don't understand it either," she said. "But I don't really care about understanding it. I just want to pursue it, Owen. Whatever this is, it feels good, and I want more of that."

"Me too," he admitted.

Chloe rested her hands on Owen's chest and slowly moved her pussy back and forth over his crotch. She watched the pleasure wash over his face and felt her clit's delight as it rubbed against his pubic bone.

"You like that guys ask me out, don't you?" she asked.

Owen nodded.

"It turned you on when I first said it, didn't it?"

"Yes," he admitted.

"You liked that the football player flirted with me today, didn't you?" Chloe asked as her pussy tingled with pleasure. "You liked thinking about me walking to class with him. You liked thinking about him trying to convince me to go to that frat party with him, didn't you?"

Chloe saw the anxiety and the embarrassment on Owen's face. It was there for just a moment, though, and was seemingly dispatched by a far more powerful sensation of pleasure that resulted in a low moan escaping his lips. Owen couldn't bring himself to answer her, though. Chloe took that as a challenge.

"Maybe I should go with him," she said with a smile. "Maybe I should accept his offer of a date."

Owen closed his eyes and groaned. He got a little more aggressive with Chloe's tits, too, though his rougher touch turned her on.

"A guy like him probably expects a kiss at the end of the night, though," she continued. "He might even expect to get his hand under my sweater, Owen. He might want to feel my tongue in his mouth while he plays with my tits through that thin, delicate little pink lace bra of mine that you love so much."

Owen's hands moved to Chloe's hips and he lifted her off his cock and set her in the bed next to him. She panicked at the notion that she'd pushed him too far, that she'd misread his face and he hadn't actually been aroused.

Then Owen sat up, pushed her legs open, and moved between them. He smiled, slipped his cock into her pussy, and lowered his body on top of hers. Chloe wrapped her legs around him as Owen began to fuck her with hard, deep thrusts, creating explosions of pleasure each time his cock bottomed out inside her and his pelvis slammed into her clit.

"If he wanted to put his hand up your sweater, to play with your tits in that little lace bra, would you let him?" Owen asked.

Chloe closed her eyes and pictured the football player. She pictured his wavy hair, the way the veins popped in his muscled forearms, the way his biceps flexed as he slung his bag over his shoulder. It wasn't hard to imagine that it would feel good if his hand wandered under her sweater while they were kissing in a dark corner at a frat party. In fact, it felt far better than she expected to even imagine that sort of thing.

"Yes, I would," she answered. "Fuck...Owen...I would absolutely let him feel me up. I would let him play with my perky little tits while I sucked on his tongue."

"Oh...fuck..." Owen uttered.

"I'd let you play with them, too," she said. "After I got home from my date. I'd let you kiss me like he kissed me. I'd like you feel me up like he did. I'd let you strip me naked, too. I'd let you have my pussy, Owen. I'd let you fuck me like you're fucking me right now, but I bet you'd fuck me even harder after another man's hands were all over me, wouldn't you?"

Owen took one of Chloe's breasts in his hand and squeezed it hard as they kissed. She dug her fingernails into his back while sucking his tongue into her mouth, eliciting a wild moan from her boyfriend.

"Yes, I'd fuck you harder," he said. "Fuck...Chloe...fuck!"

"Cum inside me," she cried out. "Cum inside me, Owen!"

He did so right as Chloe's orgasm arrived. They came together as he collapsed on top of her. She kicked her legs open and felt her thighs tremble while she ran her hands up and down her boyfriend's back as his cock pulsed in her wet, thoroughly satisfied pussy.

Eventually, Owen pulled out and rolled off of her. The cool air hit Chloe's sweaty body and she closed her eyes and smiled as Owen's cum slowly began to drip out of her.

"Do you really get asked out all the time?" he asked.

"I do," she answered. "And a guy really did ask me to a frat party today."

Chloe turned her head and saw Owen staring at the ceiling. A few moments later, he turned his head and met her gaze.

"You should go with him to the party," he said.

The anxiety that had been there before seemed to be gone. In its place was an unexpected sense of confidence, as if Owen was completely on board with the words he'd just uttered.

"Are you sure?" she asked with genuine surprise in her voice.

"Yeah. I mean, only if you want to, of course. But I think it might be really...well, I don't know, really hot," he said.

Chloe stared at him for a few seconds before smiling and saying, "Okay. I'll go to the frat party with him. I'll make sure to wear that pink lace bra, too."

That put a smile on Owen's face. Chloe wasn't entirely sure it was a good idea for her to go to the frat party, but she couldn't deny a certain sense of excitement, maybe for no other reason that it was a truly wild thing to do, and college was the perfect time in her life to have a little wild fun.