Ollie & Owen: Straight to Gay College Roommates (MM Dorm Romance)

by Jack Woolf

  "What was that?" Owen asked, pulling his mouth off his dick.

  "I want to cum," Oliver said, louder and more forceful but unable to make it sound like he wanted.

  "Good. I want to drink your cum," Owen said before taking him back in his mouth.

  Owen stroked him faster, sucking him as far as his mouth would go. Unable to help himself, Oliver started thrusting into Owen's mouth. Owen helped him control his speed, his free hand on Oliver's hips. When Oliver could finally feel himself reach the edge, Owen mumbled something with his head still in his mouth. It was enough to make him come, spilling himself inside of Owen's mouth.

  Owen swallowed everything, his throat bobbing up and down. He made sure to suck Oliver clean too, before pulling away.

  "How was that?" he asked and Oliver just stared at him in a daze.

  "That was wow," Oliver managed to say, a little breathless. He closed his eyes but then opened them again when he noticed the tent in Owen's boxers. "What about you?" He gestured to Owen's cock and Owen laughed.

  "I can take care of myself," he paused for a while and then smiled at Oliver. "Unless you want to help?"

  Oliver had never touched a dick that wasn't his own before, but he figured if Owen could suck him off, he could too. He didn't trust himself to speak so he nodded. Owen smiled and leaned back on the bed, pulling Oliver in between his legs.

  "All I need you to do is jerk me off with your hand and that'll be good enough for now," he said. Oliver nodded, but he was glad when Owen took the initiative, pushing off his shorts and directing Oliver's hands to his dick.

  Owen was hard, and it sent tingles down his spine when Oliver thought that he did that. The glide was rough, with his hand being dry and so was Owen's dick. Spitting on his hand and on Owen's cock, Oliver was glad when it made it easier to stroke Owen.

  "Yeah, just like that," Owen muttered, eyes dark and steady on his movements. Oliver found it hot how Owen couldn't look away. "I like it fast, by the way," Owen said, urging Oliver to stroke faster. Oliver willingly complied. It was the least he could do after Owen gave him the best blowjob of his life.

  He smiled and focused on stroking Owen, adding more spit when it became dry. Owen groaned and moaned, muttering things that spurred Oliver on. Oliver was quickly realizing how talkative Owen would be during sex, and it thrilled him.

  "Do it, faster, yeah, that's good." Owen moaned. "You're so good. That's perfect." Owen kept praising him and it made Oliver want to do better. He wasn't ready to suck Owen off, but he decided a short kiss wouldn't hurt.

  It felt odd to be kissing someone else's dick but it wasn't too bad. It proved to be effective as Owen twitched in his hands and Oliver took that as a sign to stroke faster. His eyes went up to look at Owen. He was straining so hard to keep his eyes open and Oliver found himself desperate for Owen to come.

  He cupped Owen's length with both hands and tightened his grip. Owen growled and muttered something, more things Oliver couldn't understand but pushed him to go faster. When Owen came, it was almost as if Oliver could feel it as well.

  "Fuck, Oliver!" was all Owen said when he came, body tightening and freezing before he spilled himself all over Oliver's hand. Oliver couldn't take his eyes away from Owen, his muscles flexed and he groaned continuously as Oliver milked him.

  Owen dropped back on the bed when he'd calmed down, sighing. "How was that?" he asked without looking at Oliver.

  "That was good," Oliver said honestly, wiping his hand on his shirt. "Now you just gotta teach me how to do everything else."

  Owen chuckled at that, pulling Oliver to plant a short kiss on his lips. "I'd be happy to teach you."

  "Looking forward to it."

  Oliver and Owen spent the rest of the week getting to know each other, going out on dates and sharing parts of themselves they usually wouldn't with other people. Oliver found it easy to open up to Owen, as did Owen, confiding in Oliver some of his fears now that university days were upon them.

  It didn't feel any different from the kind of friendship they had started, but it was definitely better. When no words would pass between them, sometimes only emotions that could be felt through a kiss and a touch would occupy their time. It gave their relationship a spark of color that touched all the grey areas in their life, painting in vivid reds, blues and yellows.

  Oliver didn't think it could feel this good to be going out with a guy, but Owen was a good friend and a sweet lover. He was patient when it came to Oliver, waited for him to feel comfortable before pushing him past one boundary to the other. He always asked Oliver's permission before trying to pass one limitation to the other. They both knew it was necessary in their relationship, to open up the world to Oliver little by little, ease him into it. Owen did such a good job, that by the time classes begun, Oliver felt a little sad to be spending hours away from his boyfriend.

  However, the beginning of the newest chapter in their lives proved to provide a good balance in their relationship. It gave them enough distance from each other to crave their partners but gave them time to bond with other people, become more than just each other's lovers. They hung out in different circles sometimes, but eventually discovered one common group of friends. It gave their relationship stability and foundation.

  It also inspired Oliver to do his own research instead of just relying on Owen's knowledge. With some of his free time, Oliver would find himself searching the internet for tips on how to have anal sex, from tips and tricks from different people to suggestions and much more. At first, Oliver felt so intimidated that he almost threw his laptop away, but he braved through the forums and read on. The more he read, the stronger the urge to feel and experience it for his own grew.

  When he had enough of research, Oliver opened up the possibility to Owen, making sure to lock their door so none of their friends could disturb them. Oliver stressed that he was willing to have sex with Owen, but needed time to prepare—that he didn't want it now, but soon.

  "So," Owen started. "What do you want to do about it?"

  "Are you a top or a bottom?"

  Owen shrugged. "I can do both, so up to you. Pick one."

  Oliver bit his lip. "I don't want to pick. You pick."

  Owen looked Oliver up and down. “Fine,” he said, breaking into a wolfish grin. “I’m going to fuck that sweet ass of yours.”

  Oliver’s face flushed red. He felt butterflies in his stomach. He was desperately curious to experience Owen’s rock-hard cock filling him up, but fear crowded his sexual desire.

  “Just promise me it won't hurt when we do it,” Oliver said.

  Owen smiled and pulled Oliver in for a kiss. "Promise," he whispered when he pulled away. “I’ll break you in gently before I have my way with you.”

  VIII.

  Now that Owen and Oliver settled who was topping and bottoming, Oliver set out to buy the necessary things for preparation. He bought the best lube, some condoms, one vibrator, one butt plug and one average-sized dildo.

  "Isn't that a bit much?" Owen asked with a chuckle as he studied the toys that came to their room just a week after they'd agreed who was who.

  Oliver shrugged. "I'm pretty sure we'll end up using all of these anyway."

  Owen nodded, realizing the truth in it.

  Once they got the tools, Oliver and Owen agreed to use the remaining week to get Oliver used to the sensation of having something inside of him. They started with fingers, Owen's fingers stretching Oliver as much as they can, scissoring until Oliver could take in three fingers at a time. They used the vibrator to distract Oliver from the pain and to help him discover the pleasure of having his prostate stimulated.

  The butt plug and dildo got Oliver accustomed to having something inside him for long periods of time. Once, Oliver wore the butt plug to all of his morning classes before begging Owen to suck him off. Luckily, Owen's afternoon classes got canceled and Oliver's next class wasn't until some hours later.

  Once the week had passed, Oliver knew he was ready. He
could feel it in the way his entrance could handle the dildo, such an easier and smoother glide than when they first started. That day also marked their first-month anniversary.

  They weren't much for celebrating, but they needed an excuse to buy two slices of cake and expensive coffee, as well as celebratory sex. It was worth it, they both said to each other. "To celebrate."

  They brought all the food back to their dorm, where they drank fancy coffee while making out. They smeared whipped cream on their lips but that only made their kisses sweeter, more tempting. When the coffees were drunk and the whipped cream licked off of lips, they turned to the cake.

  At first they fed each other the pieces before Owen realized how much better they would taste if he licked them off of Oliver's body. Oliver agreed if he could the same to Owen. He wasn't one to protest, just eagerly taking off their shirts so they could be naked again. Owen cut up small pieces of the cakes and left them on top of Oliver's nipples, one on his belly button and another one on the middle dip of his abs.

  Owen took his time lapping up the pastry, licking and sucking, leaving purplish marks on Oliver's skin. He left the ones on Oliver's nipples for last, but by then, Oliver could feel that they were already hard and ready. Owen didn't seem to mind when he got to them, sucking and nibbling on the hard nubs. Oliver groaned and canted his hips forward.

  "Your turn," Owen said, leaving his boyfriend's nipples hard and cold. Oliver groaned before pulling off his shorts. They'd barely bothered with clothes when they bought their celebratory snacks, too desperate to be all over each other.

  "My turn indeed," he whispered, pushing Owen back, pulling his shorts low on his hips. He placed a small piece by the edge of Owen's shorts, starting a trail from there until he placed the last one on Owen's lips. "Don't think about opening your mouth to eat the cake." Owen smiled in obedience and Oliver began his ascent over Owen's body.

  He started with the one by the edge of Owen's pants, almost on top of the hair. He smirked when one by one he ate the cake, opening his mouth to place open-mouthed kisses along the trail. He detoured around Owen's neck, placing sticky kisses and sucking his skin.

  Owen moaned through closed lips and they sounded like a plea to Oliver's ears. He decided to tease Owen a little more before finally eating the piece of cake on Owen's lips. Mouth opened wide, he swiped the cake into his mouth and kissed Owen, coaxing his lips open. Owen eagerly returned the kiss and pushed Oliver back to the bed so he was lying on top of him.

  Oliver didn't mind and let Owen do what he wanted; he loved the feeling of his lips on his after all. Owen kissed like he always wanted Oliver, always needed their lips locked in a dance that left them breathless. Oliver moaned when Owen's tongue stroked his own, twirling around the soft muscle until Owen was sucking it into his own mouth.

  Oliver rocked his hips against Owen's, the friction like fireworks shooting up his already hard cock. He needed more, needed skin-to-skin contact, needed to feel Owen's lips and hands all over his body. He made quick work of Owen's shorts, fingers trembling and messing up when Owen's kisses distracted him. Eventually, he managed to pull the fabric down, dragging Owen's boxers along the way. Owen quickly pulled away to kick off his shorts while Oliver lazily stroked his cock, waiting.

  When their bodies touched, finally bare, Oliver sighed and kissed Owen once more, a peck on his lips and then up his jaw, until his lips were touching Owen's ear.

  "I need you to fuck me," he whispered.

  "God, yes," Owen cried out. After grabbing the lube from the bedside table, Owen poured a good amount on his cock, already hard from all the teasing they'd done earlier that. He coated his cock with a good amount and smiled at Oliver's plugged-up hole.

  He gently pulled on the dildo, relishing the way it made Oliver's cock twitch. When it was finally gone, he took the time to admire Oliver's winking hole, tempting him to just thrust in. But he couldn't do that because Oliver wasn't used to his girth yet. Owen bit his lip and carefully positioned his cock against Oliver's entrance.

  "Relax," Owen reminded Oliver. Oliver nodded and took a deep breath. Slowly, Owen pushed in and Oliver closed his eyes at the sensation. Owen was bigger than the dildo they used to practice, but it made the stretch and burn much more bearable. It confused Oliver; he didn't know if it was pleasure or pain he was feeling. He just knew that he liked it.

  Owen grit his teeth as he pushed in deeper. Oliver was tight and he felt so good that he had to chant to himself repeatedly to take it slow. To distract him and Oliver, he started stroking Oliver's cock, just loose strokes that would bring pleasure to Oliver. Oliver moaned and started tightening up, pulling more and more of Owen into him.

  "Fuck," Owen said when he was finally balls deep into Oliver. He fell to lean his forehead against Oliver's. "I love you."

  It shocked Oliver and it made him tighten up before he smiled and pulled Owen in for a kiss. "I love you too," he whispered after pulling away. "Now fuck me properly."

  "Gladly!" Owen pulled out slow and then pushed in fast and deep.

  "Fuck!" they both said.

  Owen started out slow, muttering how good and perfect Oliver felt. He increased his speed gradually, giving in to Oliver's demands when he begged him to go faster. When Owen finally started hitting his prostate, Oliver's mouth fell open, silent moans and screams being pulled out of him. Owen kept his pace to a fast and brutal thrust, driving Oliver mad with pleasure.

  Oliver loved the feeling of Owen's cock inside of him, hot and hard, throbbing whenever Oliver tightened up and he couldn't help it when he pushed back against Owen. He needed him deeper and faster. Owen complied, his hips moving like crazy.

  When Owen started stroking his cock, Oliver cried out, incoherent at first until, "I'm gonna come, gonna come, gonna come—"

  He kept chanting until he could feel himself standing on the edge, needing that one push.

  On a particularly deep thrust and well-timed stroke, Oliver came, spilling himself all over his chest and sheets. Owen pulled out, stroking the both of them with his hands. Oliver watched, dazed before helping Owen out, watching him come all over their hands moments after he sprayed his own seed.

  Owen collapsed on top of him and panted, "We need to shower."

  Oliver just laughed. "Pretty sure you just wrecked my ass, jerk, so it's either you carry me to the shower or you wipe us off for the afternoon."

  "You know I'd be willing to do both,” Owen replied. “Honestly, though, I'd rather just fuck you again. But first let’s rest."

  "Sounds like a plan to me,” Oliver said.

  Owen held Oliver in his arms, and nothing had ever felt so right.

  Thank you for reading Ollie and Owen by Jack Woolf. Please consider leaving a review of this book to help other readers decide whether they might like reading Ollie and Owen’s story almost as much as I enjoyed writing it. To receive a free copy of my sexy short work Taboo Graduation Night, please sign up for my author email list at http://eepurl.com/bj9pKL

  Also by Jack Woolf …

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ok with friends