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Darksider
Darksider
293 Followers

Tony winced, "And the other is going to have to take it up the ass..."

Greg frowned "Yeah..."

"Well he'll I'll suck you off I ain't having my poor virgin hole invaded!" Tony protested.

"Well screw that! I don't want it in my ass either!" Greg decided.

"One of us has to... that shit head Selser won't take anything less!"

"We'll have to rock paper scissors for it, best of three." Greg said.

Tony shook his head in disbelief, "Rock paper scissors and loser gets it in the asshole... I never thought I'd be playing for that!"

Greg just shook his head in agreement, and put out his fist. Tony puts his fist out as well, and in unison they raise and lowered them four times, on the fourth time Greg put out scissors and Tony paper.

"Shit!" Tony cursed.

On the second round Greg threw scissors again and this time Tony threw rock. Cursing under his breath Greg readied for the final round and decided to throw scissors for a third time in a row. Tony again threw rock.

"fuck..." Greg muttered.

"Well that's settled than!" Tony stated, sighing with relief.

"Lets get this over with."

Ten minutes later the boys had the camera set up on a tri-pod with the best view of Greg's bed available. Greg nervously took one last look through the viewfinder of the camera to see that the shot was good, and then went to his bed sitting on it in position. Tony stood waiting behind the camera.

"Woah woah wait a minute! Let's clarify a couple things before I press record!" Tony said holding up a hand. "I'm putting my dick in your ass... so, you're clean up there right? I ain't gonna get all-"

"I took a nice shit a half hour ago and wiped myself nice and clean with a wet towel afterwards if that's what you're getting at... I'm cleaned out." Greg said, frowning, and then wincing inwardly at the thought of what's to come.

"Okay... and, how big are you anyway? I'll be able to... well you know, get it in my mouth right?" Tony asked, awkwardly and avoiding eye contact.

Greg rolled his eyes. "You've seen me in the locker room Tony!"

"I never paid much attention... and well, you were never hard!"

"I'm 8 and a half inches." Greg revealed.

"Oh... jeez! Don't gag me or nothing buddy!"

He rolled his eyes again. "I won't! But wait a minute! How big are you? I'm the one that has to get it up the ass!"

"Well, I'm no 8 and a half inches... maybe 7, but I'm thick..." Tony explained. Greg looked worried. "Don't worry buddy, I'll be gentle." Tony said with an effeminate tone in his voice.

Greg cracked a smile, "asshole..."

"I'm gonna start recording, You ready?" Tony asked.

"Oh... Wait!" Greg said, and pulled his sleeveless t-shirt off his back, exposing his hairless muscled upper body. He then picked his ass off the bed long enough to pull his gym shorts off, leaving him in navy blue boxer briefs, the bulge of his softy making an impression in the front of the clinging cotton. He grabbed the hardcore porn magazine off his nightstand and leaned back on his bed, opening up to a pictorial of a big-dicked hunk giving it to a buxom blonde, anal style. For once, he felt the woman's pain. "Okay... I guess I'm ready."

"Time to get this over with, I'm gonna press record..." announced Tony. As Tony's finger readied to press record, Greg began forcing himself to ignore the camera and his watching roommate and focus completely on the dirty magazine in front of him (a magazine that would have already given him a hard-on had he been alone with it in the bathroom sitting on the toilet). Greg stared directly at the images of the woman being penetrated in every position imaginable as Tony pressed record. Greg snaked his own hand down his firm chest and rippled abs. Rubbing all the way down to the bulge contained in the front of his jockey shorts. A few slow rotations of his fingers over his covered package began to cause expansion in his drawers. Greg turned the small circling of his hand to a long calculated rub of his open palm up and down the entire area of his growing bulge. He let out an almost inaudible groan with the exhale of his breath, continuing to rub over his briefs in all the right places. The growing bulge grew bigger with each rub, until a full-grown tent had pitched in the navy blue underpants. His cock aching to break right through the cotton, Greg continued focusing on the porn magazine, not even noticing the single wet spot of pre-cum that had already soaked through the material.

Tony could not believe what he was watching from behind the camera. He never in a million years thought about watching another man masturbating, much less his good friend, team mate, and roommate. What's more, Tony couldn't believe the response he was feeling in his own crotch. He hadn't gotten an aching hard-on, but his cock twitched every so often, and was not entirely soft any longer as he watched. He watched as Greg finally decided to set his painful erection free, pulling his right hand away from the tower formed in his jockeys just long enough to yank the briefs down by the elastic waist band. He tugged the front down just enough to get caught around his hairless ball sack. As Greg quickly wrapped his palm around his exposed cock and slowly stoked upwards, squeezing out another single drop of pre-cum, Tony found himself so enthralled that he almost forgot this was his cue to come on camera.

Stroking himself methodically, completely engaged with the magazine in front of his face, Greg had shut out his surroundings. He was half-legitimately startled to hear Tony's voice interrupting his masturbation session, until he realized this is what they went over before hand.

"What's goin' on in here budd- Oh!" Tony said, stepping on camera and looking down at his roommate pleasuring himself on his bed. Tony was trying his best to act surprised, instead of nervous and camera-shy like he felt.

Greg looked up, acting surprised as well. He combined the embarrassment he felt over the whole situation, with an acted embarrassment and flug the magazine down to cover up his towering erection.

For a moment Tony forgot his line, and dreaded what would come after he remembered the line. He swallowed hard, and then it came to him. "Woah! Buddy... why didn't you just tell me you were horny, I could help you take care of that." He said, trying his best to sound genuine, despite his horrible acting skills.

Greg just lay there unable to come up with a reasonable reaction. Instead, he waited as Tony came closer to the bed, sat on the edge of it next to Greg's spread out lower half. He reached out and pulled the magazine off of Greg's hard-on.

For a moment Tony hesitated, trying to get over the fact that he was about to grab a hold of another guys stiff cock. Finally he reached out and wrapped a hand around it, feeling his roommate tense up at his touch. He took a deep breath, hesitated again, opened his mouth and slowly lowered his head down towards Greg's cock. Not wanting to see what he was getting himself into, Tony closed his eyes on descent, and ended up feeling the mushroom head of Greg's cock push into the area between his upper-lip and nostrils. Cursing to himself he backed up a bit and tried again, feeling the cock slip to the side and rubbing against his left cheek. Finally he had to open his eyes, point the rigid cock in the right direction with his grip, and guide it between his wide-open mouth.

Greg let out a sigh of relief. 'he's got it in his mouth!' he thought. Then he thought about making the video realistic and hot for the sick bastard. "Oh yeah suck my dick Tony." He said out loud, realizing afterwards that it sounded mechanical and flat. Then Tony's lips closed around him just under the head, and Tony began swirling his tongue around the tip in his mouth, and then down to the area of the underside of his cock just below the head. He didn't know what Tony was thinking, but the next thing out of his mouth was completely genuine, "Ooooooooh, yeah!" He breathed.

Tony had devised a plan of attack. He was going to use every thing that he liked when a girl blew him, as well as every he would have liked a girl to do. After doing the tongue swirling trick a few more times, and feeling his roommate squirm every time he flicked his tongue on the spot just under the cock head, Tony dared to venture a little further down his buddy's shaft. About halfway down Tony realized that Greg really did have a long cock. He was pretty sure the tip would hit his throat at any moment and cause a gag reflex, so he stopped moving his mouth down and began bringing it back up. Taking the cock completely out of his mouth, and turning his head sideways, he ran his wet lips down one side of the cock and all the way back. All the while slowly but smoothly running the hand around Greg's cock up and down, twisting it slightly as he neared the top. As he dived back in for a second go-round inside his mouth, he brought his free hand down to pull Greg's underwear completely out of the way. Greg lifted his ass up just enough for Tony to pull them down his legs allowing Greg to kick them off. With Greg's testicles now free from holding the jockeys out of the way, Tony was able to use his free hand to fondle the balls between his fingers and rub them gently. Tony went back to bobbing his head up and down, lips wrapped tightly around Greg's member. Tony began gradually increasing his speed, and began twisting his head slightly on the way down. All the while Tony was working up as much spit in his mouth as possible, completely lathering the length of Greg's cock, creating a slippery and wet situation in Greg's crotch. Tony hoped this was looking good for the damn camera, because there would be no retakes! Also, he wondered if all these things he thought he'd like were working well for Greg.

Greg had no clue what Tony was doing down there, but it was driving his cock crazy. No chick he'd ever been with had been able to keep his cock this slick, jack him off and blow him, and give attention to his boys in the sack all at the same time. Not to mention make it feel this damn good. It was head he could only wish girls knew how to give. Closing his eyes and leaning his head back, Greg tried to block out the camera, tried to block out the whole fucked up situation and focus solely on how amazing it all felt. But the one thing he couldn't get out of his mind was that he was receiving this hot pleasure from his equally straight roommate and friend, and he could care less. Letting his mouth hang open, Greg released a long, slow guttural groan. His eyes shot open as Tony seemed to respond to the groan by doubling the pace of his oral assault. "Awe yeah, Holy shit!" He let out without even realizing he'd said it. He couldn't suppress his need to respond any longer, and reaching out with both hands, he placed them on Tony's head, grabbing at his spiked sweaty hair he tried to push him down even further.

Tony knew he was doing something right, because as he began moving faster and faster Greg began lifting his hips up off the bed as if he were trying to push himself inside his mouth further and experience more pleasure. When Greg put his hands on the back of his head, Tony knew things were going better than expected. Then Greg started rocking his hips faster and more dramatically, and Tony had to be careful not to let Greg force his entire length in his mouth and down his throat. Greg began to seem possessed with pleasure as he pushed harder on the back of Tony's head, Tony felt the wet cock slide farther and farther in his mouth, until he felt it at the back of his mouth at his tonsils, with still a lot of room for more. Before Tony knew what was happening, Greg was forcing himself past his tonsils with every thrust of his hips. Tony thought he might gag as Greg's long cock slid further down his throat until Tony finally found his nose pressed firmly against Greg's sweaty skin right where his pubic hair would be.

Greg couldn't control himself any longer and began fully fucking Tony's face. Each ram of his cock down the throat of his roommate sent a shiver of pleasure up his entire spine that brought him closer and closer to an explosion. Finally, he felt it building deep in his groin and began thrusting into Tony's poor mouth furiously. "OH SHIT YEAH! FUCK YEAH! OH FUCK YEAH!" Greg was ready to blow his load.

Tony couldn't stand it any longer and decided to abort mission. Pulling back with enough force to push away from Greg's hands on his head, Tony withdrew Greg's slippery dick from his throat and mouth. Immediately he felt himself gagging and coughing. He suppressed urge in his throat and used an arm to wipe the tears out of the corners of his eyes. He looked up at his roommate to find an apologetic but disappointed look on his face. 'You wanna play rough?' he thought, and then out loud announced "My turn!"

Greg wasn't sure he was comfortable with the look on Tony's face as he stood up off the bed. The look seemed to Greg to say Tony was fully ready to take control, and wasn't going to be easy on him. Suddenly Greg wished he hadn't gotten over zealous in the midst of the fantastic blow job he'd been receiving. With no turning back now, Greg slid up the bed a bit and propped himself up on his elbows, leaning his head back on the headboard. He watched as Tony first removed his sleeveless t-shirt revealing his tan and toned upper body. A small patch of dark hair ran from his belly button down what lay under his shorts and underwear. Tony grabbed the bottle of lube waiting on the nightstand and tossed it Greg's way.

"Get your asshole nice and slippery." Tony ordered, and found himself surprised at his own directness. As he watched Greg nervously unscrew the cap and squeeze out some of the slippery substance out into his left hand, Tony pulled off his shorts and briefs, kicking them aside revealing a cock that he himself was surprised to find erect and waiting. A cock with a small nicely trimmed patch of dark hair at it's base.

Greg wondered if his eyes had visibly bugged out of his head for a second. Tony was right, his dick certainly wasn't as long as his own, however it was definitely one of the fattest cocks Greg had ever seen. 'That's supposed to fit in my ass?!' Greg thought to himself. "Better lube yourself up too, Tony." He decided as he tossed the bottle back at his roommate. As Tony began squeezing some out onto his hand, Greg brought his lube filled hand down between his legs, spreading them wide. As his open hand found its mark, Greg rubbed the lube in circles all around the outside of his puckered asshole. The liquid felt surprisingly warm as it touched his ass. Greg looked up to see that Tony had completely slicked up his fat cock and was climbing back onto the bed, this time up on his knees.

Slick and ready, Tony tried to look as natural as he could for the camera as he pondered how exactly he was going to go about starting this. He decided to treat it as if he were fucking some slut college girl, instead of his male roommate. Crawling between Greg's open legs, Tony realized how little help Greg was going to give. Greg looked dumbfounded and more than a little worried. Tony tried to ignore Greg's look of worry and focus at the task at hand; stuffing his fat cock into Greg's tiny asshole. He wrapped an arm under each of Greg's toned thighs and lifted up as he moved even closer towards where Greg's spread legs met. Tony brought Greg's legs higher off the bed until his target finally came into view. Everything between Greg's parted cheeks was glistening wet from all the lube, especially around the area of one small puckered hole. It was Tony's turn to look worried. Of all the college tail Tony had scored since the beginning of the fall semester, he'd never done anal with any of the chicks, and looking at Greg's tiny hole, he questioned the physical possibility of this working.

Greg's anxiety was not eased as he watched Tony's expression change at first glimpse between his cheeks. But Greg watched as Tony quickly hid his expression and released his hold on one of Greg's thighs to reach down and bring his rocket in for the landing. Greg shut his eyes as he felt the tip of Tony's dick touch the outside of his rear entryway. Greg felt Tony apply the slightest bit of pressure, and despite all the lube, there was no penetration.

"Here I go." Tony warned.

Greg squeezed his eyes shut and clenched his teeth as he felt Tony increase the pressure, and still nothing gave. But Tony didn't let up on his pressure and Greg was beginning to feel the stinging pains of his efforts. Quickly Greg tried to recall any and all the information he knew about anal sex. Somewhere in the recesses of his mind he recalled an interview he'd read with a porn star on some web site, who was asked how she took so much in her ass. Greg remembered her response: 'relax, breathe out, and when someone is penetrating me, I push out like I'm taking a dump'. Stinging pain growing, Greg quickly switched tactics. He opened his eyes and unclenched his teeth, slowly exhaling, he pushed his bowel muscles and to his amazement he felt the pain ease and Tony's fat cock head slip into his anus.

For a moment Tony thought all his fear had come true and there was no way he was getting in Greg's ass. Suddenly however, he slid past the opening and his cock head was being engulfed by his roommates tight virgin ass. With all the lube involved, Tony easily slid about half the length of his cock into Greg's ass, letting out a sigh of satisfaction at the intense pleasure Greg's squeezing ass muscles had on his cock. The ass was warm, wet, and inviting, no matter who it belonged to, and Tony closed his eyes and let out a soft moan as he pulled his cock almost out of Greg's hole and slowly slid it back in again.

As the relief subsided and Greg had a chance to think about what was happening he realized that being fucked in the ass was not the worst thing in the world. The stretching/full feeling was intriguing and as Tony slowly rocked in and out his cock created a not at all unpleasant feeling as it brushed past nerve endings just inside Greg's asshole.

Tony wondered why he had never enticed a chick to do anal before. The ass was tighter and warmer than any vagina he'd ever dived into and all the lube made it every bit as wet. Pretty soon Tony had worked into a slow but steady rhythm of in and out with his hips, and when he finally looked down to meet eyes with Greg, he saw that his roommate didn't seem to be hating this. In that case, he decided to turn it up a notch.

Greg was starting to get into the rhythm of the slow steady fuck he was receiving when he noticed Tony begin to go increase his speed slightly and push in a little further. The trend continued until Greg felt Tony's patch of pubic hair brushing against his ass cheeks with each thrust. Before long Tony was grunting and groaning as he piston humped in and out of Greg's ass, Greg was alarmed as he realized that he was enjoying it. Greg attempted to determine why he was taking to the ass pounding he was getting, and was able to pinpoint a specific area of pleasure. For a brief moment just as Tony had jammed the length of his cock into his ass, Greg felt a slight jolt of pleasure as the upside of Tony's dick head brushed against a certain area at the top Greg's anal wall. The problem was, Tony's cock was only lightly brushing up against this unknown sweet spot, and Greg needed more. "Come on! Harder! Fuck me harder Tony!" He demanded.

Surprised and delighted by Greg's request, Tony obliged and began utterly slamming his cock into Greg's tight wet hole. Through clenched teeth Tony grunted and let out a continuing string of "Fuck yeah" as his balls made an audible slap against Greg's ass cheeks. Tony had never felt anything so utterly pleasurable in his life as ramming his roommate's sweaty ass.

Darksider
Darksider
293 Followers