Roommates Ch. 04bymichaeliam©
Jackson drove home in silence, but his brain was working overtime. The past forty-eight hours had taken him into an unexpected world that both excited him and scared the shit out of him at the same time. His ass hurt, but as he thought about why it hurt his cock began to stir. As he thought about Donald standing behind him, taking him in the shower as the water pelted them both, his cock stiffened uncomfortably in his pants. As he drove closer to his place, he slipped a hand down his pants and straightened out his cock and it immediately came to a full erection. He removed his hand from inside his pants and gently rubbed his crotch as he continued down the road. Would he tell Derek? Would Derek even be home? Maybe he'd be home and asleep. Jackson quickly checked the clock on the dash board and saw that it was approaching midnight. There was a chance he could quietly slip in and go straight to bed. Absentmindedly, his hand returned to rubbing his crotch. His hard cock felt good to his touch and he found himself alternately thinking of Derek's cock and Donald's cock. Before he knew it, he was home.
As quietly as possible, he slipped the key in the lock and opened the door. As he stepped through, he saw a dim light coming from Derek's room and he heard Derek call out, "It that you, roomie? You alone?"
"Yes," Jackson responded; "I'm alone." He walked over to Derek's room and poked his head through the door and was momentarily startled to see Derek lying on his bed, naked, looking at his girly magazines, with a raging hard-on.
Involuntarily, he licked his lips, a gesture that was not missed by Derek.
Derek smiled and reached down and grabbed is cock and waved it at Jackson, "Did you miss me?"
Jackson couldn't help but smile as he pushed through the door saying in a light-hearted manner, "Fuck you." His easy manner encouraged Derek.
"Aw, come on.... Kiss the baby," chided Derek as he continued to wave his cock in Jackson's direction.
Jackson sat on the bed next to Derek and grabbed the magazine out of his hands and started flipping through the pages, looking but not looking. Smiling, he glanced down at Derek's cock and then at Derek, who continued talking in a high pitched voice, pretending to be his cock speaking to Jackson, "Where have you been so late? Baby was beginning to think you don't like me. Don't you think I need a 'goodnight kiss' before I go to bed?"
Jackson dropped the magazine on the floor and hesitated only a moment before leaning down and taking Derek's cock into his mouth. Derek released his cock with a moan and Jackson grasped the hard cock with his hand and pushed his mouth down over the head. His fingers released the hot shaft and moved down to cup Derek's balls as he took more and more of Derek's cock into his mouth. Derek rested his hand on Jackson's head and moaned softly as Jackson sucked up and down on his pole. Jackson grabbed Derek's cock with his left hand and squeezed it gently while continuing to suck and slurp the head and shaft. His right hand caressed the supple balls, while the forefinger pushed its way between Derek's legs toward his asshole.
"YES," cried Derek as he let his hand fall beside him while opening his legs farther apart, granting Jackson easier access to his hole. Jackson took advantage of the extra space and quickly his forefinger found its mark, wiggling into the tight spot. Derek pushed his ass toward Jackson's finger while alternately pushing his cock toward Jackson's mouth. A rhythm was quickly established as Derek fucked Jackson's mouth while Jackson's finger fucked Derek's ass. "I'm going to cum! I'm going to cum!" Derek cried, warning Jackson. But Jackson wanted this moment. He increased his tempo as Derek continued his warnings. Soon Jackson felt Derek's cock expand, his balls tighten, and with a final push into Derek's ass, Derek's cock exploded into Jackson's hungry mouth. Jackson relished in receiving Derek's load as he felt Derek's dick pulse and release one, then two then three strong spurts of hot cum. He milked Derek's cock while fingering his hole until Derek pushed him away. "No more; no more. O shit; that was fucking fantastic. Damn man, you're a cock sucking monster!"
Jackson released Derek's cock and removed his finger and leaned back, watching his roommate pant and regain composure. His own cock was throbbing in his pants, and he knew just where he wanted to put it. He thought of Donald taking him, and he remembered that Derek had a dildo and a vibrator in his drawer. Tonight, he would fuck Derek's ass like there was no tomorrow.
While Derek composed himself, Jackson stood and removed his shirt. Next, he undid his belt and unbuttoned his pants and let them fall to the floor. His underwear followed and in moments, he was naked, his hard cock pointing out proudly. He grabbed his cock and stroked it a few times as he walked to the side table, where a tube of lube sat. Derek continued to breathe heavily, recovering from his orgasm, but watched his roommate move about. Jackson grabbed the lube, looked at Derek and said, "Roll over."
Derek's eyes opened wide. "Are you going to fuck me?"
Jackson smile, "Roll over and stick that cherry ass up in the air"
Obediently, Derek rolled over and tucked his knees up under him and stuck his ass up in the air, resting his head on his pillow. He reached around and grabbed his ass cheeks and pulled them apart, exposing his brown hole to his roommate. Jackson climbed on the bed behind Derek and opened the lube and drizzled a liberal amount on his cock and on Derek's ass. Tossing the lube aside, he began with a finger, probing the hole before him. Derek sighed. Positioning his cock toward the target, Jackson moved in until his cock came in contact with Derek's ass. He ran the tip of his dick up and down the crack as Derek continued to moan in a whisper, "Fuck me, dude. Fuck my ass."
As if on command, Jackson pressed his dick against the hole and slowly pushed his cock. Reluctantly, Derek's ass began opening to receive Jackson's cock. Jackson grunted as his cock slid into the tight hole until his hips rested against Derek's ass cheeks. "Oh fuck," Derek cried; "Oh fuck, that hurts so good!" He pushed himself back toward Jackson loving the feeling of his roommate filling his ass. Jackson paused for a moment, feeling his cock throb as Derek's ass clasped it tightly. He knew he wasn't going to last very long, so he wanted to enjoy every moment. Slowly, he began to withdraw his dick, pulling out until just his tip was buried, and he drove hard back in until his hips slapped Derek's ass. "YES!" cried Derek, "AGAIN." Jackson complied and slowly withdrew again, only to ram his cock back inside Derek's hot little ass.
Derek met each thrust with a groan of delight as Jackson pounded his ass. After a few minutes, Jackson began feeling that familiar sensation growing in his cock, telling him he was about to cum. He increased his tempo, thrusting harder and harder as Derek moaned and encouraged him on. He felt his cock began to expand and his balls tighten, and with one last mighty thrust, he pushed himself into Derek and his cock exploded. He pumped his cum into Derek's ass with several more thrusts and Derek met each one with enthusiasm. Reluctantly, Jackson withdrew his cock, slapped Derek playfully on the ass and got off the bed. Derek remained in position, with his ass in the air and watched his roommate gather his clothes and head to the shower. Jackson looked back and smiled at him, "See you in the morning, roomie." Derek smiled back and only nodded.
Jackson lay in his bed reviewing his evening. Donald was amazing. Derek was fun. Though he was exhausted, emotionally and physically, he could not deny enjoying this new aspect of his sexuality. He moved his hand toward his cock and begin lightly fondling it, enjoying the feeling both in his hand and on his dick. It was a little soar, as was his ass. He smiled to himself and drifted off to sleep, dreaming of hard cocks and tight asses.
The next thing Jackson knew he was having a wonderful dream in which he was making passionate love to his girlfriend. It all seemed so real as he felt her mouth on his hard cock. She never let him cum in her mouth, so when he got closer, he said "I'm going to blow!" It was then he began to transition from dreaming to consciousness and realized that his cock wasn't in his girlfriend's mouth, but in Derek's! He felt is body tense then he rammed his cock into Derek's mouth and filled it with is cum. Derek took it all in eagerly, milking and sucking Jackson's cock until it began to soften. "Damn, boy; what a great way to be awakened in the morning."
Derek smiled. "I've wanted to do that for a long time." An hour earlier, Derek had awakened and decided that this would be the day he fulfilled one of his fantasies.... He entered Jackson's room and found him sleeping soundly. Gently, he pulled back the covers exposing Jackson's hard body. He was delighted to see that Jackson was sleeping in the buff. By the soft light of the early morning, Derek gently began gently caressing the flacid cock watching as Jackson came to a full erection. He let his fingers lightly dance along the shaft down to the balls enjoying himself fully. Finally, he leaned closer and took a long, slow lick from the base to the tip of Jackson's cock. When a drip of precum oozed out of the tip, he gently covered the slit with his mouth and sucked out the human nectar. Jackson moaned but did not awaken.
Derek lifted his roommate's cock and pointed it at his mouth. He closed his eyes and lowered his mouth over hard dick and began sucking as he slowly moved his hand up and down the length of Jackson's shaft. He wondered if Jackson were dreaming as subtle moans escaped his lips. Derek took his time, exploring each area of Jackson's cock, the helmet, the soft ridge and the smooth long shaft. As he sucked and licked his friend's dick, he thought back over the last two days... was it just the night before last that he had put his plan into action? He was somewhat surprised at how willingly Jackson had been last night to suck his cock, and totally shocked at the iniation Jackson took when he fucked Derek's ass. He had deliberately woken up early yesterday morning so as not to have to talk to Jackson after the previous evening's activities, but when it was approaching midnight and Jackson hadn't returned, he feared the worst. The sound of the key in the door caused him to sigh....
Jackson's stirring brought him back around to the present as he felt Jackson's hand upon his head. He quickened his pace and began sucking and jacking Jackson's cock knowing he had to be close to cumming. He heard him cry out, "I'm going to blow!" Then the first load of cum filled his mouth, then the second, as he greedily sucked and milked his friend's cock dry as Jackson commented on how nice it was to wake up with his dick in someone's mouth. He noted the contented look on Jackson's face and leaned back on the bed.
"So, Roomie, where did you go last night after work? I was starting to get worried I'd scared you off."
Jackson smiled to himself. He had been deliberating on how much to tell Derek about the previous evening. His ass still hurt a bit, but thinking about it was making his cock stir..."A guy I work with invited me for to his house for a drink after work and I went. We ended up talking most of the night, tossing an easy dinner together with leftovers from his fridge." Jackson hoped that would be the end of the conversation, but Derek continued.
"Really? And what did you talk about?" Derek probed, sensing that there was more to the story than Jackson was letting on. Jackson's whole manner last night suggested more. The relaxed way he had sat on the bed, casually flipping through the magazine and his quick response in sucking Derek's dick suggested to Derek that Jackson's evening had been eventful. Now, he wanted to know about those events. After some gentle coaxing, Jackson began to recount his troubled day and Don's awareness of his plight. He told him about the scotch, the Jacuzzi (including the intentional jet pointed right at his cock). Derek made a comment about wanting to sit in that spot, but Jackson let it pass without comment. He went on to talk about the shower and the bed afterward. As he told his story to his roommate, Jackson noticed Derek's hand disappear into his boxers. He thought it was an absentminded gesture in response to Jackson's story. It was not. Derek was a bit of a voyeur and was getting more turned on by the fact that he was masturbating in front of his roommate than he was in hearing what happened to Jackson the night before.
Jackson was only mildly distracted by his roommate's hand, but clearly Derek had gone from lightly caressing his cock to jacking off. As he finished up his description of the previous evening, Derek pulled his cock out in the open and moved his hand deliberately up and down his shaft as Jackson watched. "I've always wanted to take a shower with you, Rommie," Derek said. "What do you say?"
Jackson smiled and said, "Let's." He got off his bed and headed toward the bathroom. Derek followed, never releasing his cock. Without further comment, Jackson turned on the water and adjusted the temperature, watching his roommate slowly masturbate. It was a familiar and unfamiliar all at the same time. Jackson had jacked off many times, but had never watched anyone else do it. He was intrigued by the way Derek used his forefinger to smear the precum on the head, something he would try the next time he jacked off.
Once the temperature was just right, Jackson climbed in and let the water flow over his head, face and chest. He waited, but not for long. Soon he felt Derek's body lightly pressing against his. He prepared himself for Derek's cock in his ass, but Derek was in no hurry. He had waited a long time for this and was in no hurry. Jackson felt Derek's cock pressing against his ass cheeks like a hotdog in a bun. Then Derek's right hand reached around and started gently caressing Jackson's nipples. The sensation sent electricity through his body. At that moment, Derek's left hand came around and lightly caressed Jackson's stomach, slowly drifting down to his cock. Jackson inhaled quickly at Derek's hand came in contact with his cock, but rather than grab it, like Don had done, Derek slowly brushed the length down to his balls and then back to the tip over and over again. A guttural moan escaped Jackson's lips as he gently leaned back against his roommate.
Derek leaned in and began to lightly kiss Jackson's neck. Jackson was initially startled. Up to this point, it had been just sex. This was sensual. It was a line he wasn't sure he wanted to cross, but the combination of Derek's hands brushing his cock and caressing his nipples melted his resolve and he gave himself fully to his roommate. Sensing the shift in his roommate's resolve, Derek continued kissing and licking Jackson's neck while opening his right hand and cupping Jackson's balls. He rubbed down between Jackson's legs as he tweaked Jackson's nipples with his other hand. Jackson continued to moan softly.
Derek stepped back and turned Jackson around and leaned in and lightly kissed him on the lips. Seeing no resistance, Derek pulled Jackson to himself letting their cock's mash together, sliding his hands down to Jackson's ass cheeks. He kissing him deeply as their bodies grinded together. Jackson abandoned himself to the moment, never realizing how alive his body could be. Derek's finger gently found and probed Jackson's ass as they kissed. Derek pulled away, looked into Jackson's eyes and said, "I want to fuck you." He punctuated his comment by inserting his finger farther into Jackson's asshole. Jackson felt his knees weaken.
He turned around facing the wall of the shower and spread his legs. He reached around, feeling for Derek's cock, and pulled Derek closer. Derek grabbed the soap and lathered up Jackson's ass using his fingers -- first one, then two. Jackson wiggled his ass against Derek's fingers, enjoying this much more than he had the night before. Derek removed his fingers and placed the tip of his cock against Jackson's hole, and pressed ever so slightly, just letting Jackson know what was coming. Derek whispered into Jackson's ear, "Here it comes, my love, nice and easy." True to his word, Derek slowly penetrated Jackson's ass while reaching around and tweaking Jackson's nipples. Derek eased his cock past the restricting muscles as Jackson relaxed, allowing the penetration.
"Oh fuck!" Jackson said, as he felt Derek's cock enter his ass. Instinctively, he pressed back against Derek's cock allowing his roommate's cock to fill his ass. The feeling was exquisite. Not at all like the night before. Jackson felt like his own cock had never been harder, never more ready to explode. As if on cue, Derek's hand dropped to Jackson's cock as he pulled out and pushed in again slowly and gently. He had just grabbed Jackson's cock and started stroking it when Jackson clamped his ass around Derek's cock and his own cock began to erupt. "Oh Shit!" Jackson cried as he bucked against Derek's cock. Derek knew Jackson was cumming so he quickened his pace and soon was pumping his own cum deep into Jackson's ass.
Jackson pushed Derek's hand away from his cock and heaved deep breaths has he tried to regain himself. He could feel Derek's cock expanding and contracting so he squeezed his ass muscles tighter, milking Derek's cock as he finished his orgasm. Derek leaned against his roommate, letting the water cascade over the two of them for several minutes before reluctantly withdrawing his cock from Jackson's ass. He grabbed the soap and gently washed Jackson's ass and his own cock. They rinsed off and got out of the shower. Jackson said, "I never knew my body could be so alive."
Derek responded with a smile. "When do I get to meet Don?"