Jack and Oliver Ch. 02

Story Info
The boys take it to the next level.
2.6k words
4.67
39.5k
13
Story does not have any tags

Part 2 of the 2 part series

Updated 10/07/2022
Created 08/26/2006
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Jack lost his balance and fell back onto the floor as Oliver shot up off the couch, tossing his shirt into his laundry basket and tucking his dick back into his pants. Pulling a fresh shirt from the closet and slipping it on, he waited until he had shut the door almost completely behind him before turning and muttering, "I'll be back later, man, don't wait up."

Oliver took off in a quick walk down the hallway, not looking to see if Jack was following him. As he exited the residence hall, he saw one of Jack's friends, a short brunette wearing denim overalls, coming toward him. Planting a hand on his chest, she stopped him with a knowing smile that had him breaking out into a sweat.

"Hey, Oliver. Have you seen Jack around?" Gesturing toward the building vaguely, he pushed past her and walked out into the park-like area that separated the residence halls from the rest of campus. He found a fat tree and sat down in its huge shadow. His breath escaped shakily from his lungs. His cock was still hard, thinking about Jack and his moans and the sexy face he made when he came. It was dangerous territory, this Jack thing. He liked his roommate so much, and didn't want anything to spoil it all.

Caroline knocked on Jack's door tentatively, and heard the muttered "Come in." She sat in, and took in the scene. The television was on, although the DVD player had been turned off. Jack's shoes sat beside the couch, and Jack himself, hair attractively mussed, was sitting dejectedly at his computer desk holding a piece of blue cloth in his hands that he was trying to squish into the smallest ball possible. After a few seconds, he stuffed the cloth into a desk drawer, and then turned around to her.

"Oh, it's you Caroline."

"What goes on here? First your roomie nearly knocks me over, and then I don't even get a hello?"

"It's nothing. We just had a little...thing."

"Seems like a pretty big thing if you're this upset about it. Did something happen?"

"Nothing I really want to talk about, if that's what you mean."

"Well, did you two..." she trailed off, leaving it a question, unasked. Jack only shrugged. "Do you want me to sit with you or anything?" Jack shrugged again, but gave his head one short nod. "Okay." Caroline sat on the couch and grabbed a book out of her bag. She read and Jack listlessly surfed the net in companionable silence. "Just tell me if you want to talk." Jack nodded.

When Oliver turned the knob to get into his room, he found Jack's bedside lamp still on, although the light was very dim. The door snicked closed behind him and he kicked off his shoes. He saw Caroline laying on the couch with her head back, snoring lightly. He wondered idly if Jack and Caroline had a sexual relationship as well as a friendly one, but doubted it. Looking finally across the room, he saw that Jack's bed, usually under the window, was empty. Had Jack gone out looking for him?

Then, a slight movement caught his eye as he was removing his clothes and pulling on a pair of pajama pants. Turning, he saw that Jack was curled up in his bed, clutching something. Leaning down, he noticed the shirt that he had been wearing earlier that afternoon in Jack's hands. He glanced at the clock. 2:00a.m. He had been outside for nearly four hours, just sitting in the dark and thinking. It was too late to wake Jack and move him, so Oliver did the only thing that made sense.

Walking over to Jack's bed, he took in the rumpled black sheets and blanket. He ran his hands through his hair and then shrugged, climbing into Jack's bed. Instantly, his roommate's scent filled his nose. Not just the dark, smoky cologne he wore, but the deeper muskier scent of his skin and of his sweat. Oliver's cock hardened a little as he pushed his nose into Jack's pillow, smelling the shampoo and the scent of Jack. Ignoring it, he fell asleep.

Jack awoke suddenly at 9a.m. the next morning, clutching Oliver's shirt to his chest and cuddling in the sheets and blankets that held Oliver's scent. He had waited until Caroline was snoring on the couch before he made the overly sentimental move to lay in Oliver's bed, but had never meant to fall asleep in it. Glancing over at his own bed, he saw Oliver, head back with a peaceful smile on his face. His roommate's chest was bare, and one hand cradled his semi-hardness through his pajama pants unconsciously. Glancing around nervously, he pulled his cock out of his pajamas and started stroking himself with Oliver's shirt.

He watched Oliver sleep, felt himself get harder and harder underneath the covers. Then, suddenly, Caroline stopped snoring, rolled over, and fell off of the couch and onto the floor with a loud bang. Jack stuffed his cock back into his pants and tossed Oliver's shirt back onto the bed. Stepping over to Caroline, he saw her stretching on the floor as if after a good night's sleep. On the other side of Caroline was Oliver, one hand extended to help her up.

As Caroline sat back onto the couch, Jack and Oliver looked at each other. Both had sleep-tousled hair and drowsy expressions on their faces. Jack knew Oliver's body would still be warm from sleep, and made a half step forward to close the gap between them, when Oliver turned and went around the couch to get to his stuff.

"I'm gonna go grab a shower. See you for breakfast?" Fixing Jack with a slightly shy smile, Oliver left the room.

It was well after nine by the time Jack finally was alone in the room with Oliver. He was pissed, too. Oliver had danced around the subject all day long, and always accepting invitations to go hang out with some of his other friends, leaving Jack behind and promising to see him "later." Every time they met that day, Oliver let his eyes wander over Jack and then give him a hot, piercing gaze that Jack was unsure how to interpret. If he didn't know better, he would have thought that Oliver was flirting with him. No one seemed to noticed anything strange, except for Caroline, who had danced about with amusement in her eyes as if she knew something he didn't.

As a matter of fact, she did. She wasn't really asleep when Oliver came into the room the night before, but had wanted to see what he'd do. Going to sleep in Jack's bed wasn't the thing she would have expected. If it had been her roommate, she'd have kicked them awake and made them go sleep in their own bed. Early the next day, she cornered Oliver just before they met Jack for breakfast.

"Listen to me, Oliver. I have known Jack for ten years. In that time, he has never so much as hinted at being gay, he has had relationships with girls. I believe he has a thing for you. But I don't think you should give in right away. Make him stew for a little. You need to make sure it's something he'll really be committed to doing. I don't want to pick up those pieces."

Finally, Caroline left, a few moments before Oliver came in. He locked the door behind him, matter-of-factly, and had hardly turned around before Jack was less than a foot away. He could feel the heat of Jack's anger pouring off him, could nearly seeing him vibrating with it.

"What the fuck is up with you?" he spat out at Oliver.

"What do you mean?" Oliver returned coolly.

"I mean...fucking going off with all these other people and ignoring me all damn day!"

"I wasn't ignoring you. I saw you a couple of different times, but you seemed busy." It was true that Jack had been going to great lengths to look busy every time he saw Oliver, so that he wouldn't look desperate, wouldn't look like he was waiting.

"Fuck that. You said you were going to meet me for dinner. Where were you?" This time, Oliver did feel a little guilty, but he didn't want to give that away...yet.

"I was out with some friends. I didn't really have a way to call you. It's not like we're dating, man," he said, acting like the previous night they hadn't been jerking each other off.

"Fuck that!" Jack shoved Oliver against the door, a bit harder than he intended. Oliver's eyes widened slightly, and Jack had that same forbidden thought that he'd had before. He wanted to kiss Oliver. He grabbed a handful of Oliver's hair, more gently, and yanked their mouths together, capturing his in a kiss. He pressed their lips together firmly, and then traced the line of Oliver's lips with his tongue. When Oliver's mouth opened to let his tongue inside, he slid it in and tangled with Oliver's tongue. Jack couldn't believe how fast his cock hardened; he'd never gotten hard from just kissing a girl before.

Oliver pushed Jack away slightly, giving him an odd look, before sliding away from the door and walking over to Jack's bed, where he sat and gave Jack a clearly inviting look. Jack pushed him into a lying position and then got on top of him, pressing his hips into the bed, rubbing their jean-clad cocks together. Jack sucked on Oliver's earlobe and then whispered into it, "You're not getting away from me this time." Oliver only nodded, breathless.

Jack sat up a little to take his shirt off, and then took off Oliver's as well. Moving back down, he pinned Oliver's arms over his head. He watched Oliver's pupils dilate with interest and felt his hips arch up in protest, although he was silent. Jack captured his mouth again and felt rather than heard Oliver's soft moans. He trailed kisses all the way down Oliver's neck to his nipples, sucking one in and biting it gently. When Oliver cried out, he bit down harder.

More kisses, and then Jack was finally at the waistband of Oliver's pants. Looking up, he saw the heated desire in Oliver's eyes. He unbuttoned Oliver's jeans and slid them down and off. He was suddenly confronted with Oliver's hard cock, this time an inch in front of his face. He did the only thing he could do; he sucked the tip into his mouth and ran his tongue around it. Oliver's cock jerked in his mouth.

"It's...it's okay if you don't want to..." Oliver trailed off in a moan as Jack slid his mouth as far down Oliver's cock as he could comfortably, which was about halfway. Jack began sliding his mouth up and down on Oliver's cock, nestling Oliver's balls neatly in his palm. Jack let Oliver's cock out of his mouth with a slight pop and regarded him with a sheepish look on his face.

"Um, do you usually...you know, how do you usually...I mean, which..." Jack blushed.

Delighted, Oliver grinned. "I usually bottom. Thanks for asking." He winked, making Jack feel instantly more at ease. He pushed Oliver's legs apart and began licking his balls slowly, up one side and down the other. Oliver moaned and pushed his hips down towards Jack, who took the cue to start licking farther and farther south. He finally reached Oliver's hole and started licking around it tentatively. When Oliver gasped in surprise, Jack wiggled his tongue into Oliver's hole and started pushing it in and out. "Please, Jack. Please..."

Jack sat up with a cat-got-the-cream grin, asking, "Please what?"

"Please fuck me." Grinning like a little kid, Jack went to go find Oliver's lubricant, and returned with the bottle. He doffed his jeans and boxers and then went to go kneel on the bed, where he found Oliver kneeling, with his head resting on his arms on Jack's pillow. Jack touched Oliver's lower back lightly.

"Hey, turn over." Oliver turned over and lay on his back, looking surprised.

"Ryan didn't like to take me this way. Only the other way."

Smiling, Jack touched Oliver's cheek. "Well it's your face that I fell for, not your ass. I mean, not that you don't have a very nice ass," he added quickly. Oliver smiled and Jack had to lean down and plant another kiss on his lips.

He squeezed some lube onto his fingers and rubbed them together, warming it slightly before sliding his fingers over Oliver's anus, where he pushed slightly, feeling his two fingers sliding in. When Oliver groaned, he looked down in concern at Oliver's slightly flushing face and closed eyes.

"Is it okay? Do I need to stop?"

"No, please don't stop." Feeling Oliver's ass loosen a little around his fingers, Jack pulled his fingers back out and lubed up his cock, then pressed it gently against Oliver's ass. "Go on, it's okay. Just give it to me." Oliver grinned up at him, and he pushed forward. He felt his cock being slowly enveloped in something warmer and tighter than he'd ever felt. Oliver let out a breath when Jack's hips touched against his and he felt completely full.

Jack took a breath, looking down at where he and Oliver joined. He saw Oliver's hand reaching for his cock, and Jack brushed away the hand. He squeezed some lube into his own hand and wrapped it around Oliver's cock. "Let me take care of that," he said in a voice deepened by desire.

Jack began rocking his hips, fucking Oliver slowly and stroking him at the same pace. Both men groaned each time that Jack slid in completely. Jack lowered himself slowly over Oliver until he felt Oliver's cock touch his belly. He touched his lips down to Oliver's, peppering his face and neck with gentle kisses while fucking him steadily. As he arched his hips to adjust his position, he thrust back in and Oliver closed his eyes and grunted, "Oh, fuck." Jack started fucking faster, each time being sure to hit that same spot inside of Oliver.

Oliver fisted the bedsheets, feeling his cock being rubbed between their bodies and still squeezed occasionally by Jack. Jack's cock was hitting just exactly the right spot, and Oliver began to moan, quietly, "Fuck...fuck...fuck..." over and over again. When Jack leaned down to kiss Oliver's neck, Oliver bit his earlobe and whispered, "Fuck me harder...please. I want to feel your cum in me." Jack felt a twinge in his balls and started hammering into Oliver.

When Oliver came, he moaned so loudly that Jack was sure that their dorm mates heard him. That said, his balls were slapping against Oliver pretty loudly as well, but all thoughts of getting caught melted as Jack felt Oliver's cum spurting up between their bodies. As he felt Oliver's ass contracting on his cock, the pleasure was too much and he bit down on Oliver's lower lip.

"I'm gonna cum in you Oliver. Fuck..." Jack kissed Oliver and moaned into his mouth as he pushed his hips all the way forward in one final thrust, filling Oliver's ass with his cum. "Shit, that was...that was something else," he mumbled as he collapsed on the bed next to Oliver, his cock sliding out of Oliver's ass. He touched the pool of cum on his belly and placed his hand on Oliver's cock. Oliver's hips jerked from sensitivity, but Jack just smoothed the cum all over Oliver. When Oliver's cock began twitching and hardening again, Jack just grinned. "You just don't stop, do you?"

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
Sunnydaze361Sunnydaze361about 1 year ago

Roommates and lovers sometimes it doesn’t work but Oliver and Jack are super hot!

LifeDreamsBigLifeDreamsBigalmost 12 years ago

This story just gets hotter every time I read it(:

AkshunLoveAkshunLoveover 13 years ago
Very sexy

Keep going :) it's hot.

AnonymousAnonymousover 14 years ago
wow

please keep going! its really good!

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Not His Type All the ways to a happy ending.in Gay Male
Sam Roommate & friend lose a game and confess his love.in Gay Male
Be Mine Adrian comes out for the love of his life.in Gay Male
Blind Faith Love is blind, or you can be blind to love.in Gay Male
We're Not Gay Two guys discover their orientation isn't what they thought.in Gay Male
More Stories