Disclaimer: This story is about men having sex with men. If that's not your thing or you're too young to read it, please leave now. In the movie on which this story is based, "40 Days and 40 Nights," the character of Matt is played by Josh Hartnett, the character of Ryan (who narrates this story) is played by Paulo Constanzo, and the character of Chris is played by Glenn Fitzgerald. The author has no knowledge of these actors' sexualities, and has written this purely as a work of erotic fantasy fiction. Condoms aren't used here, but you should use them (duh!). Eat your vegetables. Register to vote. Recycle. Enjoy!
40 Days and 39 Nights
by Backlash29
backlash29@hotmail.com
If you've surfed the Web at all in the last six months, chances are you've heard about my would-be hetero stud roommate, Matt Sullivan. Matt became a local folk hero last spring when he swore himself off sex completely--even masturbation--for lent (the forty days leading up to Easter).
Why he did this is anyone's guess. He claims it was because he was devastated by his break-up with Nicole, this blond bitch he was dating who dumped him for some stuck-up finance prick. As Matt's friends, we all let him know we thought Nicole was evil and he should have said good-bye to her long before he did. Still, Matt was plenty upset, and I guess every time he tried to date women after that he got messed up in the head. So, he decided to give sex a rest for a while and see what would come of it. As it is, he made a few discoveries about sex that he wasn't prepared for, and much to my pleasant surprise, I even got to help.
My name is Ryan. I met Matt shortly after we both moved to San Francisco after college. He moved here to take some great job at a software company. I had other reasons, which I didn't bother to tell him about at first: the ready availability of sex with hot men.
When I was in a fraternity in southern California, I made the discovery that I was bisexual. I happened during pledge week, when I was forced to suck the cocks of two upperclassmen and they came in my mouth. For a few weeks after that, I found myself craving a repeat of that experience, and once I got up the nerve to approach my frat brothers on this issue, they were more than happy to comply. For the next three and a half years I sucked just about every cock in the frat, and I got my ass boned by more than a few hot studs along the way as well. All during this time, I continued dating women, and when I moved to San Francisco after graduation, I was determined to enjoy what I could of sex with both genders. But meeting Matt, who was straight and fucked women prolifically, I decided not to mention my bi side, and when he asked me to share an apartment with him, I figured the truth would come out eventually in its own time.
The truth is, I had quite a crush on Matt from the very beginning. He's a skinny guy, like me, but he was as cute as any dude from my former frat house, and his voice was so deep and sexy it made me want to just pounce on him and fuck his brains out every chance I got. Besides, I found his regular sexual liaisons with hot women to be incredibly distracting, and it made me horny just about 24/7. Starting the first week we lived together, I had to lie in my room at night and listen to the female moans coming from his bedroom most nights, and beat off thinking it was me instead of his girlfriend, riding up and down on his cock.
That's the other thing--Matt has this incredible cock. He was never shy about showing it off, and he frequently walked around our place wearing nothing, or else wearing his tight white underwear that showed the huge bulge in his package. His cock was long and fat: almost ten inches, and about as thick around as my wrist. I got to see it hard a few times early on, when he'd come to my room for condoms when he and his chick were in the heat of passion. No wonder all the girls moaned. It was truly a sight to behold.
To avoid any real confrontation with Matt about my varied sex life, I started having all of my male encounters outside the apartment. There were just one too many close calls, where a hot dude I'd met out drinking was ass-fucking me good and deep in my bedroom, and we had to be as quiet as possible because Matt was with his girl the next room, thinking I was either asleep or bedding down some girl myself. Besides, it was downright tricky to get those boys in and out of the apartment without Matt seeing what was going on. So, instead, I went to the parks, the bars, and the sex clubs--like the Power Station, where I regularly sucked dicks to my heart's content, or dropped my jeans and leaned into the concrete walls as some beautiful well-hung young man had his way with my eager ass. The Castro isn't that far from our apartment or where I work, so it was fairly easy to go out for happy hour, meet some stud, and then head back to his place for a hot blowjob or a quick fuck before catching the subway home.
So, around home, I kept up a good cover by dating and screwing only women, just like Matt did. Since the women in San Francisco were more attractive to me than the ones I'd met in L.A. this was an easy thing to do. On an average week-end, I'd bring a girl home on Friday night and we'd have our fun. Typically, Matt would bring home two or even three girls over the course of the week-end. On a good week, he would bring home women on the weekday evening as well, while I was in my room alone. Invariably I would then have to listen to them going at it, which both aroused and upset me most of the time. I was aroused because it was impossible not to think about that fat cock of Matt's whenever I heard some girl wailing like a banshee as he drilled it into her. And I was upset, and a little jealous, because in the back of my mind I wondered: If all Matt needs to do is get off all the time, why doesn't he take advantage of the hot, lusting mouth and ass of his roommate and best buddy, jerking himself off in the room next door?
It all changed when Matt took the vow. He told me about it before he told anyone else, and I swore he was crazy. I told him I knew him better than he knew himself, and there was no way he could tolerate six whole weeks without sperming himself or drilling it into some chick. But he insisted. I guess he had something he needed to prove to himself. I was against the whole thing, but I decided to take it in stride.
The real trouble started after his buddies at work got wind of what was going on. Evidently he let it slip to them about his vow he'd taken, and knowing Matt the same way I did, they understood immediately that Matt would fall prey to his own horny instincts before the forty days was up--it was just a matter of time. That's how the whole betting pool came about. And while it sounds like a corny idea now to bet on someone's sex life, I'm glad we did, because as a result of doing so, I got ten solid days of hot sex with none other than Matt, my would-be hetero stud roommate. And I owe it all to his gorgeous co-worker, Chris.
I'd met Chris a few times, when I joined Matt and his office buddies for drinks after work or on a week-end at the clubs. He was a sexy Brit, a few years older than us I guess, probably pushing thirty. He always had a cigarette tucked behind one ear, and when he talked, you got the feeling he was hiding something sly. I thought he was very cute, and I noticed that while other the other guys we hung out with obsessed about women, Chris never seemed to have much to say on the subject. A few times when I'd lock eyes with him, his would sparkle briefly and he'd flash me a quick smile. I wondered if this meant what I thought it meant.
During the first week of Matt's vow, I was at home alone, getting my work clothes off to take a shower, when the door buzzer rang. Dressed in just my shorts, I went to the door and opened it wide. There was Chris, looking as handsome and stylish as ever. His blond hair was trimmed short, and the trademark cigarette was visible over his left lobe. He wore dark pants, a dark sweater, and a black jacket. In one hand he held a leather pack. I don't think he'd been to our place before. He looked fuckin' great.
"Chris, buddy," I greeted him. "C'mon in, I was just going to hit the shower."
"Hey Ryan, mate. I was just in the neighborhood..."
He followed me inside and sat down. As I emerged from the bedroom, pulling on the 49'ers jersey I use for lounging around the apartment, I was aware that his eyes were focused on my body. Now, I'm skinny like Matt is, but we both work out regularly, and I was pretty proud of my bod at this point. The women I dated never seemed to have any objections to me, nor did the hot guys who fucked my mouth and ass, so I figured I had to be a decent-looking guy. Having Chris scope me out like this felt electric.
"So man..." I asked him "What's up?"
"Do you know?" he asked bluntly. "About your roommate's...situation?"
At first I didn't know what he was talking about. "His what?"
"Matt's vow," he said, impatient. "He's taken a vow of celibacy for the next forty days."
I laughed. "Oh, that. Yeah, we talk about it constantly. Matt's pretty obsessed." I flopped down next to Chris on the sofa. "It's only been a few days, but I don't think he's going to make it. I'm surprised he's gotten this far."
"Precisely," Chris agreed, and he proceeded to explain. It seems that the guys at the office had generated an office pool around betting on how soon Matt would break with his vow, and now several of them were in dead heat to see who would win the pot of money by choosing the correct day when Matt would slip.
All of this was very funny to me, and I howled with enjoyment as Chris continued to describe the situation. "Dude, that is SO cruel," I said. "But Matt deserves it. He made it everyone's problem already, with that skank he was dating who he now can't get over. Once he gets this out of his system, we'll all be better off."
Chris relaxed back into the sofa, but his eyes were still focused intently on me. He'd had a look of concern ever since I opened the door to find him standing there, sexy as ever in our hall. "Right," he agreed. "Still, there's a bit more to the story now. Neil--you know, the bloke we work with--he's putting together a Web site, and pretty soon people around the country and around the world are going to be betting on this thing. The pot is likely to grow quite huge."
This just made me laugh more. After a moment, the wonderful glint in his eye showed once more, and soon he was laughing with me. I finally asked him: "Alright, so what do you need from me?"
In response, Chris opened the leather pack he'd carried in with him. He pulled out a small device, which I figured out was a camera, attached by a short wire to a small black brick-like electronic box.
"Do you have a computer?" he asked. I nodded, and got up from the sofa. Chris followed me down the hall to my bedroom, and I pointed to the PC on my desk in the corner. "Perfect," he said. "This will work great. And Matt's bedroom is just beyond this wall?" He gestured to the wall that the computer desk was against.
"Yeah," I said. "So, what are we doing?"
"It's simple," Chris said, as he began connecting the black box attached to the camera to a port on the back of my computer using a different wire he pulled out of his bag. "Those of us who set up this little venture, we need some insurance that our Matty is behaving his fine self. And..." --he winked at me-- "those of us who bet on the pool, we will need some proof."
With that, I watched for the next ten minutes as Chris, who it seemed was some kind of perverted expert at surveillance, drilled a couple of simple holes in the wall between my bedroom and Matt's, then fiddled with some software on my computer until suddenly the whole area of Matt's bedroom was visible in a browser window on my computer screen!
"Voila," Chris said proudly. "You now have a view of all of Matt's activities, nocturnal and otherwise. And, as long as you keep this browser window open for the next few weeks, I'll be able to connect to this site and record what's happening on a day-by-day basis. Don't worry, I'm the only one who sees it besides you."
"Jesus," I said, whistling. "It's that simple?"
"It's that simple." Chris sat on my bed. "Doesn't bother you, does it?"
I blinked at him. "Well, yeah, it does, a little. I mean, shouldn't I respect my roommate's privacy?"
"You can if you want to," Chris said dismissively. "Just don't tune in to that window. But we need the camera to be active steadily, so that we'll know the exact moment that the pool is over."
Then, suddenly, everything changed. Chris leaned back a bit on his haunches, still smiling up at me. The crotch of his trendy dark pants tightened as his body moved backwards onto the bed, and provided a detailed outline of his considerable bulge. My eyes focused on it and I couldn't look away.
"Besides," Chris went on, using a softer voice now, "it could be very convenient for you in some ways..."
I swallowed hard. "What...what are you talking about?"
"Well, after this silly business is over, you'll get a chance to see our beauty-boy doing all those things he loves to do with women. And without him having to know it, you'll have a front-row seat."
I looked over at the screen, its still shot of the empty bedroom. Suddenly I pictured Matt on the bed, on his back, his milky chest muscles shining in the camera lens as he played with himself, or as some hot woman rode up and down on his cock. I would now have a visual to go with the endless nights I listened to Matt giving himself and his conquests so much pleasure. But how did Chris know...?
"I think you'll like having it," Chris purred seductively. "In fact, I think you'll like it quite a lot."
Nervously, I gazed at the computer screen a moment longer, and then dared myself to look back at Chris. He was as beautiful as ever, and as I watched him, his hand moved to his crotch, and he began gently stroking the bulge that was visible in the fabric of his pants.
I didn't know what to say, but it was clear to both of us what Chris wanted. So, in a trance, I stepped closer to him, and at the foot of the bed, I knelt and slowly pushed his legs apart. Chris reached down and patted my head, running his fingers lightly over my hair and then pulling me closer to his crotch.
"Yes-s-s-ss, Ryan," he groaned softly. "Do it for me now. It's always seemed like something you wanted."
I unbuttoned the pants and pulled them off him, exposing his muscular legs and a trendy pair of blue-grey briefs. He was right, I had wanted this. From the moment I'd met him I had wondered what it might be like to suck his cock. And on this night, I hadn't had sex with men in one week, so I was hungry for some dick.
I descended on his cock first through the underwear, running my tongue and teeth along the sexy outline of his growing erection, getting the cotton fabric wet and pliable with my mouth. This made Chris groan with pleasure, and his fingers stroking my hair began pulling me urgently toward him. After a few minutes, I finally let my fingers slip beneath the waistband and pull the underwear all the way down and off. He had a great cock, not as long and fat as Matt's but plenty big and a beautiful shape. Best of all, he was uncut. I licked all around his cockhead and foreskin, then put the whole thing into my mouth and began working my magic, sending long, luscious slurps the full length up and down the delicious hard cock.
"Oo-o-oh, Ryan...yes..." he moaned. "Yes, Ryan...that's perfect...that's so perfect..."
His cock tasted so fucking good. I wanted to just stay there on my knees and worship it forever. As I sucked him, he continued to make the cutest noises, groaning and muttering encouragements in that soft, Brit voice of his. Pretty soon I had my whole upper body into it: I gripped his turgid cock in my right fist, and used my left hand against his hairy, muscular thigh, pushing his hot legs wide open for easier access. I then sucked up and down using my face, my head, my neck, and my torso, making long strokes on his big cock with my mouth. He responded by groaning even louder and more urgently, and pressed his strong hands against the back of my head, egging me on.
After a few minutes of this, I could tell he was getting close to cumming, and as much as I loved giving him head I really wanted a shot at getting his cock inside my ass. When I pulled back to catch my breath and look up into his glazed-over, blissed-out face, I was instantly sure we both wanted the same thing.
"Get up, lover," he said to me. "Get on the bed with me. I want to fuck that sweet little ass."
He was right, I did have a sweet little ass. Most guys can't tell from the clothes I wear, but in addition to being relatively cute and having a decent upper body, I have a tight ass that I work out and keep in great shape. Since my favorite way to be fucked is doggy-style, I didn't even wait to take direction from Chris. I got on the bed next to him, on all fours, and craned my head back to watch him pull his shirt off so that he was fully naked. I then moaned as I watched him approach the bed, his big hard-on swinging ahead of him as he walked. Swooning, I reached into the nearby desk drawer and flung a bottle of lube onto the mattress.
"That is one hot ass, Ryan," he complimented me. "Does it like getting railed by big uncut cocks?"
"Fuck yeah," I purred. "Dude, I am so ready to get fucked. I want that big thing in me...now!"
I scooted back a little so that I was at the edge of the bed, and he could easily get started with me in a standing position. He put both hands on my waiting ass-cheeks, and slapped his hard uncut cock in my crack several times. When I felt impatient, I looked around at him again and wiggled my ass. "What's up?"
"Condoms?" he asked. "Or, do you like it...raw?"
"Up to you, stud," I told him. "I usually take it natural, but if you want to suit up to fuck me, it's all fine."
He picked up the bottle of lube and squirted a big puddle into one hand, then tossed the lube aside and began applying it directly to his throbbing limey schlong. "Raw it is," he said, and a second later I felt the bliss of his fat cock head prying between my ass globes, finding my hole, and plunging its way inside.
"OOH! FUCK!" I yelled, then gasped. "Yeah, fuck me! Oh man, do it Chris, that feels so fuckin' good!"
Encouraged, he paused for a moment, adjusted his double-handed grip on my hips, and then started in throttling my hot hole for all he was worth. I was in shock for the first few seconds, and then slowly, gradually, I just relaxed my whole body and collapsed forward, my upper body flat against the mattress, my whole being in a state of ecstasy, giving my ass fully to him, taking his hard, raunchy fuck.
"Ohhh...yeah...oh man...fuck me...do it...I love it...fuck me nice and hard..." I moaned.
"Fuck," he grunted, exerting himself ever harder with ever successive stroke into my willing ass. "Take my fuckin' cock, Ryan...you love it up your hole, don'tcha, you lousy boy-bitch...you've been wanting this dick in your tight little hole..."
I played along. "Yes! Oh yes...fuck me, stud...I've wanted this cock so bad...give it all to me, I need your big dick way up deep inside me...fuck em, Chris, I want your big cock!"
It wasn't long before he was ready to shoot. "You want my cum inside you, bitch?" he asked.
"Yes, please..." I barely had a chance to let the words escape when I felt the first volley of Chris' hot cum spray into my asshole, followed by a dozen more jets, all flooding my ass and covering my insides. After that came another dozen or so smaller spurts and jerks, and then finally he was at rest inside me.
He relaxed for a minute, then pulled out and rolled me over. My raging hard-on was still slapping against my flat stomach, painfully hard.
"Hey man, you gotta get off," he noted, his voice much kinder now than I could remember ever hearing. "Where do you want to put your load? In my mouth or in my ass?"
My eyes grew wide. I couldn't believe this stud was offering to let me fuck him!
He read my reaction and laughed. "Yeah, I can be quite the butt-ranger myself, Ryan laddie," he said, climbing over me on the bed and then gently lowering himself over my groin. "Truth is, I love your cock, and I always have wanted to get it in here."
Chris used some more of the lube on my cock, then lined-up my dickhead with his tight, brown hole and slid it all the way inside. I looked up to see this incredibly sexy man close his eyes and wince with pain and pleasure, then open them and look back down at me and smile again, my cock totally inside his hot ass.
"Fuck me, stud," he instructed, and proceeded to ride his tender butt cheeks slowly up and down over my cock. I responded by doing the most natural thing I knew how--I thrust as deeply into him as hard as I could. His ass felt heavenly wrapped around my aching erection, and once we got our movements coordinated it only took a few minutes worth of long, deep upward strokes before I lost control inside him, coating Chris' ass with sperm exactly as he'd done for me moments before.
When we were done, he collapsed forward on top of me, and rewarded me with a deep, sensuous kiss.
Suddenly, I looked at the clock. "Shit! It's after 6! Matt's going to be home any second..."
And then, I heard the voice that would change everything. It came not from Chris, but from the bedroom doorway, out of my line of vision because of the beautiful man on top of me who had just milked my load with his ass. It was a voice I recognized well, and hearing it sent a shiver all the way up my naked spine:
"Matt's already home, boys. I got here ten minutes ago, and you've got some explaining to do!"
Chris and I both scrambled to untangle ourselves and look up at the doorway. There stood Matt, looking very cute and puzzled and maybe (I thought) a little bit pissed off.
"Hey man, I can explain..." I began, but Matt put up his hand to stop me.
"We'll talk about it later," he said, and turned away from the doorway and headed down to his room.
Chris and I heard Matt's bedroom door shut, and we looked at each other in shock. Chris whispered to me: "Doesn't he know you're into guys?" to which I whispered in reply, "Fuck no! It never came up." Chris then paused thoughtfully, and whispered: "Me either. I guess he's probably quite freaked out..."
We stayed there, naked and motionless, for another few seconds, and then we both thought of the same idea at the same time. I lunged for the computer desk and jiggled the mouse to get rid of the screen saver. We were now looking directly into Matt's bedroom, and sure enough, Matt was on the bed. He seemed to be groping his crotch through his clothing, and muttering in a low tone. W both raced over and put out ears to the wall, and after a moment we could make out what he was saying:
"No, can't do it, that's not right. I shouldn't be turned on by this shit anyway. What the fuck..."
We looked back at the computer. Matt leapt off the bed, began pacing the room, and finally sat down at his desk, pulling out the latest in his collection of half-assembled miniature cars. Fitfully, he forced himself to concentrate on the task of readying the parts and supplies, and a moment later he was diligently at work with his hobby.
"That was a close one yesterday," Chris said to me when he called me at work the next day. After watching Matt return to his model cars, we had both gotten dressed and I had wordlessly and hastily ushered Chris out the door. Matt stayed in his room the rest of the evening, so we had yet to have our face-to-face confrontation about what he'd seen.
"Shit dude, I can't talk about this at work," I told him. "I'm on my lunch break, but I gotta get back in a few seconds."
"Oh. Well, alright. I just wanted to say...I had a really great time."
I felt touched by this, but also self-conscious. I didn't have very much privacy using our office phone. "Yeah, me too," I said. And then, when I realized that sounded lame, I added: "It was a really great time. I hope we do it again."
"We will," Chris promised in his sexiest voice. "OK, Matt's back. Don't worry, I won't bring any of this up."
"Later."
We rung off then, and for the rest of the day I felt a warm glow knowing Chris had called me back for no reason other than to say he had a good time when we were together. It felt like a high school crush. I tried to remember feeling so happy hearing from someone before, guy or girl, but no occasion came to mind.
That night, after work, Matt and I talked it out. He stopped by my bedroom as I was reading the latest Sporting Green.
"Jesus man, it's not like I don't listen to you having sex all the time," I told him, trying to play it off as just another roommate's tryst. "And I know you've heard it when I'm going at it, with my own dates in the past."
Matt rolled his eyes, incredulous. "Yeah, but man...those were GIRLS!" His eyes narrowed, and he looked at me, suspicious. "Weren't they?"
I laughed. "Yeah, it's just been girls for me before yesterday. At least around here. Well, lately."
"Around here?"
"Well...yeah. I've done it with plenty of guys before, I just don't ever bring them home any more, because I didn't want to freak you out. I used to do it sometimes, but now I haven't for over a year."
Matt pondered this. "So...where did you take them?"
I decided not to tell him about the parks, or the sex clubs, or my frat house experiences from the early days. "Their place," I said, shrugging.
"I see." Matt was silent for a moment. Then he paced the room for a few moments, and then he left the room altogether for about ten minutes. When he returned, he asked: "What about those girls from Tahoe?"
"What about them?"
"They were HOT, man! You said so yourself! And after mine walked out on me, I could hear you banging yours for most of the night!"
I put down my magazine and glared at him, impatient. "Of course they were hot, Matt. I like hot women. Sometimes. Well, most of the time. But...I really like, you know, this other stuff as well. Get it?"
He sighed, defeated. "I don't get it, no, not really. But it's your life." He paused. "And, you know, you're my good friend, and this is your place too, so...do whatever you want."
At that point, I softened somewhat. "That's cool, man. Thanks for being understanding."
I expected him to leave then, but when I looked up a few minutes later, he was still standing there, a few steps inside my doorway, at the foot of my bed.
"Yeah?" I asked.
"So I'm wondering...what DO you do? I mean...what I walked in on..."
I laughed again. "Matt--I don't think you really want to know that..."
"Why not?"
I set down my magazine and leaned forward on the bed. "One, you've got this fruity abstinence pledge going on, so I don't think you should be talking about sex with me, even if it is guy-guy cornholing type stuff. And two, why do you have to ask? If you were really standing there for ten or twenty minutes or whatever, I'm sure you had all your questions answered."
Matt blinked several times, rapidly. He does this whenever he has some emotion that he doesn't want to betray to whomever he's speaking to. In this case, I could tell he was recalling what he'd seen in this bed the previous day: his buddy and co-worker Chris, strapping and naked and aroused, fucking the hell out of me, his roommate, and then taking a ride on my fat, engorged cock until I blew my load inside his ass.
Then I glanced down. Matt's bulge had been showing for several days now, thanks to Mother Nature's response to the little no-sex game he was playing. But at this moment, he appeared to be as erect as I'd ever seen him. His hard dick made a tent that stuck out six inches from his belly inside the baggy shorts he wore. Below the bulge, his soft, muscular legs looked as sexy and fine as ever. Instinctively, I licked my lips.
Matt caught this gesture, and realized where I was looking. With a whoop, he grabbed his crotch to flatten the tent that had formed, and wide-eyed, he stepped backward toward the bedroom door. I laughed at him, because it was one of the cutest things I'd seen him do since this whole vow thing started.
"I...I, uh...I gotta go..." he stammered.
"More time with your model cars, Matty?" I teased him.
"I...well, no...I, um...." he glanced in the direction of his room, clearly indecisive about what he was feeling and how he was going to respond. "No...I better, I better just go. I'm going. I'm going...out."
With that, he ran to his room, pulled on some jeans that would hide his bulging crotch slightly better, and exited the apartment in a flash.
"Day 33," Chris said to the group of us. I was hanging out with several of Matt's co-workers, all of whom were now involved with the betting pool. "Shit, I never should have put money down on this thing. The kid's got better resolve than any of us thought."
"Tell us about it," another co-worker lamented, gesturing to the friend next to him. "We had bet on Day 25, over a week ago. Do you think he's really going to make it?"
"Hell no," Candy spoke up. She was another co-worker who, with another girl at the office, had tried unsuccessfully to tempt Matt into seduction one day at work. "He'll break at some point. We just don't know when."
I took a swig of my beer, then looked at Chris. His gaze caught mine, and he flashed a smile that made my pulse flutter inside my chest. Ever since the day Matt had caught us a few weeks earlier, we had been meeting at either his place or my bedroom for our discreet trysts. We never again did it with Matt around, and Matt never mentioned it again to me or anyone else. So, our secret affair remained a secret, even among this tight-knit group of friends.
After beers, I said my good-byes to everyone and prepared to wander home. Chris met me in the alley for a quick kiss, followed by me groping his hot crotch. We made plans for him to stop over the next day (a Saturday) and plow my ass. I got a hard-on just thinking about it. He was such an unbelievably hot fuck.
When I got to the apartment, I was alone--or so I thought. I knocked on Matt's door a few times, but got no answer, so I figured he was out for a Friday night on the town. Thing is, ever since taking the vow, Matt wasn't much of a night-on-the-town type of guy. He was more intent on staying home and keeping out of trouble, meaning out of the path of temptation in the many forms it could take.
I entered my bedroom and flopped down on the bed. After a few minutes, I swore I could hear noises coming from the bedroom next door. Finally I realized I could look into the room using the secret camera Chris had installed. I used it to spy on Matt constantly, but because he was being so fastidious about his vow of celibacy, there was never anything juicy for me to look at: just Matt sleeping, or Matt working on models, or Matt talking on the phone to his wierdo priest brother, or Matt just reading a book.
Tonight, however was something different. I switched on the computer monitor, and sure enough, there he was on the bed. He was wearing only his white cotton briefs, along with his wireless stereo headphones, playing music I couldn't hear, which was the reason he hadn't heard me knocking. Most curious of all, he was splayed on the bed in a very erotic position, with his legs spread wide in a V-shape, his eyes closed, and the same bulge in his tighty-whities that I'd seen for the last several weeks.
As I puzzled over what he was doing, I realized I was getting hard. After a few moments, Matt slowly came out of that position and rolled into another one. This time, he was on all fours doing a sort of cat stretch, his excellent ass pushed enticingly out into the middle of the room. It was, I recalled fondly, the very same position in which Chris had power-fucked me that very first time on MY bed, with Matt watching.
I finally figured out what Matt was doing. It was some kind of yoga, transcendental whatever, I suppose to keep his mind off sex. But the positions he chose were so erotic to me that they gave me raging hard-on that wouldn't quit. After a few minutes of watching, I decided to yield to the opportunity that the situation provided. I opened my pants, fell backward on the bed, and as I watched my hot, celibate roommate stretch his tight body in multiple positions, I flogged my cock. It didn't take long before I started visualizing the things I would do to Matt if I were in that room with him. Finally, when he got in some position on his back where he hugged his knees close to his chest, I felt my orgasm swelling. I pictured what it would be like to be standing before him as he did that stretch, drilling my hard cock in and out of his straight-boy tail. And when I shot my load all over myself, I imagined I was filling my roommate's butt with jizz.
A minute later, after I'd come back down to earth, I realized something: As the weeks grew on, Matt was getting hornier and hornier. And his horniness was feeding my horniness, as well as the horniness of practically everyone around him. In particular, Chris and I had been fucking like rabbits ever since Matt had caught us in the act that first time. As it was, I had just shot off watching Matt do yoga--yoga, for Christ's sake--and the orgasm was twice as intense as I'd ever had while beating off in that same bed, listening to Matt fuck some girl in his room, and wishing that girl was me.
In that moment, I began formulating a plan...
"You want to what?"
"I want to convince him to tie himself up," I said to Chris the next day at his apartment. We had just shared a very intense and satisfying fuck, and were relaxing on his bed together in a puddle of sweat and cum.
"You're crazy. When? Why? Why would he do it?"
"On Day 39. Next week. He'll be so crazy with lust at that point, he'll do anything we say."
"If he makes it that far," Chris pointed out.
"Babe, you and I both know, he's determined to do this. I think he's going to take it all the way."
Chris considered this, then shrugged. "What the hell. I've already lost in this betting pool anyway."
Playfully, I started toying with Chris' deflated cock. "But that doesn't mean we can't still have fun."
He watched me, and gently stroked my hair. "What are you thinking, you evil little boy?"
I flashed him a wicked grin. "I'm thinking about how hot he's going to look, spread-eagle on his bed, with both wrists handcuffed to the bedposts."
"God yes," Chris moaned. "It's an enticing image, I'll give you that. I've wanted to put my meat inside that boy for a long time now. Just seeing him tied up like that would be heaven. Do you think he'll do it?"
"Of course he will. He'll be so tempted to touch himself that last night, he'll be delirious. It's the only way."
"And what will we do?"
Chris' cock was growing now, and I continued to play with it in my hand. "We'll film it, of course. Secretly. And when Erica, his new girlfriend, comes by at 12:01 to pay her respects, we will have some of the best live streaming porn the Internet has ever seen. We can sell the advertising for a thousand bucks a pop!"
And so a great enterprise was born, even bigger than the betting pool: Tune in live to see Matt, the abstinence god, shoot his first wad in forty days with the girl he met in the laundromat back on Day 2!
I felt a little guilty about it, but once again, Matt had asked for it, and all the publicity he got for his "vow" stunt deserved some other recognition in kind. So we set it up, got people to pay for access, found some advertisers, and upgraded the server Chris was using to host the live feed so that it could handle the extra bandwidth necessary for this one-time event. It would be bigger than Pamela Anderson and Tommy Lee!
Everything was going fine until the evening of Day 39. Matt totally went along with the handcuffs idea; as I had predicted, he was in a miserable state of deprivation and anticipation at that late point, and needed all the help he could get keeping his paws off his own cock. So, at 6pm, as soon as he got home from the office, Chris and I helped chain him to the bedposts, turned on the TV to his favorite sports station, and left the room.
Chris and I being the fuck-hungry newlyweds that we are, it was only about a half-hour later in the living room that we started getting frisky. I began by sucking Chris' cock on the sofa--it a rare treat to do this out in the open in my own apartment, because we both knew Matt wouldn't be interrupting us! Then, soon enough, Chris had bent me over one of the sofa arms and was starting to drill his fantastic cock up in my ass. I always moan loudly when he does this, but I must have moaned louder than usual, because we suddenly heard Matt shouting from the back bedroom:
"Holy fuck! Can you guys quit it! Jesus Christ, it's hard enough to focus without you guys going at it..."
We immediately stopped our sex, alarmed, and looked at each other. For a split second I actually felt pity for my undersexed roommate. But then, I began thinking about all the times the tables had been turned, and I had listened to him fuck girls in his bedroom, as I was left alone in mine, with just my own right hand. Poor Matty didn't even have his own right hand available!
Chris and I stared intently at each other, and slowly smiled, forming a silent plan together. We then stood up, pulling off what few clothes remained on our bodies, and ran wildly down the hall to Matt's bedroom.
"What the...? What the hell are you guys doing here!" Matt shouted from the bed. "Get out, get out!"
"No can do, Matt my lad," Chris said, and after positioning me directly in front of Matt's view, he dropped to his knees and started sucking my cock.
I moaned, making a show of it, groping my own body luxuriously, rubbing my nipples and caressing myself as Chris made oral love to my eager cock.
"Holy shit...c'mon, quit it, you guys, you can't do this...why are you doing this...stop it..."
But Matt's protests fell on deaf ears. In fact, now that we were fully involved with this little prank, the whole scenario became incredibly fun and freeing. It had only been a few weeks earlier that I had spent a whole day feeling guilty about having Matt catch me in the act with my new boyfriend. Now, the two of us were going at it directly in front of him, and unless he closed his eyes, he couldn't possibly look away.
After Chris had blown my cock for a little while, he stood up and positioned me the way he wanted me, with me on my feet bent-over the footboard of Matt's bed. As Matt watched intently, Chris filled-up my ass once again with his cock and started sawing in and out of me, just as he'd been doing on the living room sofa before we were so rudely interrupted.
I looked up--Matt's eyes indeed weren't closed, but rather were wide open and focused on the scene we were playing out before him. Breathless with satisfaction but ever wanting more, I looked directly into my roommate's eyes as I groaned to my lover behind me: "Oh yeah, fuck me Chris...it feels so good...I love having your whole big dick inside me, man...fuck me, fuck my hot hard little ass..."
Chris got into it also, pounding my ass for all he was worth, grunting and snarling in that masterful way of his: "Yes, take it you little cock-bitch, you live for my hot dick up inside that nasty little fuck-boy hole..."
Our groaning built to a crescendo, and at the last I lost focus on Matt and simply collapsed on the bedclothes, feeling the joy of yielding myself as a receptacle to my lover's powerful, unrelenting thrusts. Soon I felt his creamy load unload itself deep inside me, and moments later I reared up and hammered off a load of my own. It landed all over the bedspread, and some of the cum even hit Matt's legs. I felt dizzy just then, but as my moans died down, and Chris' did also, I was suddenly aware that a third voice had been moaning with us. My head darted up and scanned then room, but there was no one there besides us three.
Of course, it was none other than Matt himself, in the throes of climax, shooting a huge, seven-plus-week load of goo into his tighty-whities. He'd cum without touching himself! Neither Chris nor I was expecting that. We had only intended to taunt and torture Matt a little, to keep his enormous ego in check. We hadn't intended to make him break the vow.
"Jesus Matty, we're sorry," Chris said, genuinely apologetic. "We didn't think you'd..."
"Shut up, you fuckers," Matt interrupted, still breathless, in his deep sexy voice. "It was worth it."
Worth it? Chris and I looked at each other, then back at Matt.
"Watching you two fuck--I don't mean just now, I mean six weeks ago--was the single hottest sexual experience of my life. All of the time since then that I've been trying to keep away from sex, it hasn't been thoughts of girls that have been occupying me. It's that damned image of you two going at it."
Chris sat next to us on the bed. "What...? Man, are you being serious?"
"Totally serious," Matt said. He strained to adjust himself within the handcuffs and find a comfortable position on the bed. Evidently, shooting such a huge load had bent him slightly out of position. "The thing is, I don't know why I'm so turned on by it, but I am. I want to try all that stuff you guys are doing, and a lot more. There's a whole world of sex out there that I'm not getting!"
I grinned then. "That's the spirit. So, enough of this stupid vow shit, right?"
"Right," he agreed. "It taught me a lesson. I mean, it would have been nice to save myself for Erica, but once you guys started fucking right there in front of me...shit, you gave me something a lot better than I could ask for from anyone, guy OR girl. You guys looked HOT."
Chris reached over to Matt's crotch. The cum Matt shot had soaked through the underwear entirely, so Chris helped remove the shorts and tossed them onto the laundry pile in the corner of the room. Sure enough, Matt's exposed cock was already rock hard and ready for more action.
"Hey," Matt asked softly. "Are you guys going to let me out of these handcuffs?"
Chris flashed him an evil grin. "I don't see any reason to do that..."
Matt's wondrous cock lay there, a slab of hard flesh, between his sexy thighs. Wordlessly, as if in a trance, I slowly leaned forward and grabbed it. This was it, my roommate's mammoth dick, the one I had wanted for so long. I wrapped my fist around its impressive girth, and after another few seconds' admiration, I gobbled the whole thing into my mouth. From Matt's reaction, I thought he was going to blow a gasket. As it was, he blew another huge wad of cum, into my mouth, down my throat, about ten second later.
"Shit," I gurgled, laughing, as I pulled my mouth off and swallowed his pent-up load. "Take it easy, man. We've got five hours before midnight."
Chris frowned. "Ah, I almost forgot about that. So now what happens at midnight?"
I looked at both of them, and said in an even tone: "Same plan as before, of course. Erica gets here, you and I are gone, and we all pretend that none of this ever happened."
And so commenced five incredible hours of hot three-way sex. Matt remained cuffed to the bed, the passive sexual student, as Chris and I introduced him to all pleasures possible for a man to give another man.
For starters, we knelt at either side of Matt's face, and taught him how to get his face fucked. Matt sucked cock like a born natural, first twisting one way to slurp Chris' fine pole down to the root and back up for several pleasurable oral strokes, then twisting the other way to do the same to me. After a bit of this it was evident that Matt was going to cum again if we didn't do something about it, so Chris did the honors, lubing up his hot asshole and sliding it down onto Matt's huge, fat cock.
"OH man...it's heavenly," he purred. "Take it easy mate, let's make this last a while if we can. I've wanted this dick inside me since the first day we worked together, more than two years ago..."
He slowly humped his ass up and down on Matt's engorged dick, with a steady enough rhythm to give them both pleasure but not so fast as to waste my roommate's precious load. As Chris rode Matt's dick, Matt continued giving me a hands-free blow-job. Finally, after ten minutes or so, Matt couldn't hold back any more, and with a whoop, he spat out my cock and yelled as he shot into Chris' talented ass:
"OH FUCK! YES!" Matt screamed in ecstasy. "Oh, yess...Chrsi...man, take it...take that fuckin' load, that is so fine...god, I love shooting my cream in your hot ass...your asshole is so fuckin' sweet... "
I bent over and kissed Matt. He wasn't expecting this, but he instantly responded. "Yes," I agreed, whispering to him. "His ass is very sweet. I should know."
Chris continued bouncing, his own hard-on flapping prominently in front of him, slapping against Matt's hard, sexy belly. "Hey Ryan, love," he addressed me. "Why don't you show Matty here your favorite way to clean me after I've been fucked."
"Mmm, I'd be glad to," I replied, enthusiastic. Chris rose slightly to let Matt's cock escape his asshole, then leaned forward against Matt's powerful young body as I got behind his ass and moved my face into position. I always enjoyed rimming guy's asses, especially when they're filled with loads of fresh cum. I was a big hit in the frat house and at the sex clubs because of this particular fondness. And, I enjoyed eating out Chris' perfect buns just about as much as any ass I'd ever rimmed. But up to this point, I'd never licked any load out of Chris other than the ones I shot there myself. Matt's juicy cum tasted and smelled altogether different, and I savored the aroma for a few deep breaths before pushing my whole face in and sucking out his hole like there's no tomorrow.
"Oh, ah, mmm...yes, do it, rim me...lick my ass, lick my hole...oh fuck, Ryan, that's so good..."
I heard Matt speak next, incredulous but aroused. "Holy shit! Am I really seeing this?"
"Yes...you're seeing it, alright Matt my mate," Chris cooed. "Believe me, it's one of the best things there is."
And when I was done rimming Chris, we showed Matt what we meant. Chris dismounted my roommate's prostrate body, and joined me between Matt's sexy legs. I lifted one thigh high, while Chris lifted the other, and soon Matt's fleshy pucker came deliciously into view. I went first, giving it a few nibbles and licks, and we both laughed at the instant and sever response: Matt struggled almost violently on the bed, savoring the unexpected electric shock of pleasure that a tongue on his anus produced. Then Chris leaned in for a few licks, then I licked a bit more. Finally, when we thought he was ready, we both lowered our faces down there and dove in fully, pressing our tongues together and licking all around and inside the hole.
Matt, meanwhile, nearly screamed with ecstasy. "OH! FUCK! Man...yes, oh man...that's so good..."
We rimmed him until he was good and loose, and ready to be fucked. "I'm going first," I told my roommate, "because Chris here has got the bigger cock. Trust me, you'll have plenty of challenge taking mine inside you, but after you get used to it and I fuck you nice and hard...you're going to be begging for Chris' dick of death to take sloppy seconds. It's the best cock I've ever had up my ass!"
I positioned myself between his splayed legs, which Chris kept aloft as I worked in more spit as lubrication. Then I pointed the tip of my painfully hard dick at Matt's hot little hole, and punched it inside, just past his tight little lips. He winced and jostled his cuffs, but other than that, there was no resistance. So, I slowly pushed forward, and before I knew it, my whole cock was deep inside my roommate's male pussy.
Only after I had fully bottomed out inside him did I hear him utter a moan: "O-o-o-oh, my god, that's big."
I kept it there for a minute or two, letting him get used to it, and savoring the look on his face as he did. There are some things only get to see once in your life, and your straight roommate's facial expression when you first penetrate his virgin ass is definitely one of them. After squirming a bit, he finally relaxed, slightly out of breath, and then gave me a nod. That was my sign to fuck him.
So, fuck him I did. After all these months of wanting Matt to bang my ass the same way he banged the endless line of women to went in and out of our apartment, here I was with my own dick balls-deep inside his perfect, butch-tight butt. I was tempted to go easy on him but soon I decided: What the hell, he's got plenty of lube, and he seems to like it--and started fucking him in earnest right off the bat. After the initial shock, Matty took it like a real man. He responded to every thrust, pushing back against my cock for more. His own dick was rock hard and spitting pre-cum onto his hot belly, in spite of having sprayed three loads in the past half-hour, into his underwear, into my mouth, and deep inside his co-worker's willing ass.
For leverage, I grabbed both of Matt's legs and held them way up high, drilling his boy-cunt wheelbarrow-style. This left Chris free to pursue other avenues of pleasure. "Hey look," he said, crouching backward over Matt's face. "I think he liked watching you give me that rim-job, wouldn't you say? D'you think he's ready to try it out for himself?"
Not giving much choice in the matter, because of the way Matt's hands were shackled, nor much say in the matter, given the way he was now sitting backwards on top of Matt's face--Chris soon had the answer he was seeking. "Oh, baby, yes," he moaned. "He's doing it, Ryan. He's licking way up deep inside my hole."
Spurred on, I continued my assault on Matt's ass. His hole was so perfect, so accommodating, that it was almost like fucking an experienced bottom. I couldn't believe I was inside the roommate I had lusted after for so long. And soon--very soon, in fact--I was going to give him his first experience of having a hot load of cum shot way up deep inside of him.
The sight was incredible. Matt, beautiful young studly Matt, had his luscious long legs draped over my shoulders as I plowed deep an hard into his hot male pussy. Meanwhile, his arms were spread even wider than his legs and held open, rendering him helpless, as he loudly slurped and moaned in his deep, sexy voice with my hot new boyfriend's face covering his handsome features. This would-be straight stud had discovered his one true calling: Giving pleasure to other men. He gave his hot hole to my cock, and he used his mouth and tongue to give Chris so much pleasure up his ass that Chris' eyes practically rolled backwrd in his head. Wanting to kiss Chris, I continued pounding Matt's hole and slowly pulled his hairy legs open, wishbone-style, leaning forward as I did so to lock lips with my special partner. We made out passionately, tongue-kissing, sharing the flavor of all this sex, relishing every moment of this fantastic hot sexual event.
My orgasm built and built, and in a series of hard, pounding climactic thrusts, I delivered my juice to Matt's hungry asshole. I screamed and banged, and his willing, beautiful ass drank every drop from my pole.
Meanwhile, he was eating Chris' asshole like a man possessed. In a few short hours, we had made a total cum-pig out of my straight roommate, feeding him loads up his ass and ass in his face. In fact, as Matt snorted around inside Chris' asshole, it gave me pleasure to know he was tasting remnants of his own load which he had shot there, and of which I had lovingly rimmed out all but the last vestiges.
After a while, it was evident that even for all of his enthusiasm, Matt's position was a difficult one for rimming, and so Chris pulled off his face. "Is he ready for more?" Chris asked.
I grabbed Matt's unfailing hard-on. "Oh yeah. I'd say he has plenty more loads in here, ready to give us."
"Splendid," Chris said. "Let's get creative, shall we?"
'Getting creative' involved figuring out how many ways we could fuck Matt and each other over the next few hours, and in how many positions. First, I mounted Matt's raging cock, while Chris assumed my old position between Matt's splayed legs, feeding his fat log into Matt's asshole to create a fuck sandwich. This proved very effective, and caused Matt to spray his cum up in my asshole almost right away. So, I dismounted, and instead of feeding my load to Chris the way I usually did, I squatted over Matt's face just as Chris had done, and fed my ass and the hot fresh load it contained to Matt's eager, slurping, hungry face.
After that, we pretty much tag-team fucked Matt for the rest of the evening. One of us would bang his hole while the other held his legs wide open, or sat on his face to muffle the moans and screams. Whenever one of us was close to cumming, we would pull out and let the other one take his turn. Whenever Matt was close to cumming, whichever of us wasn't fucking him would sit down onto his cock and take his precious load way up deep inside us. Time after time, he managed to cum like a demon. In total, we got ten loads from Matt's undersexed cock that night: five in each of our asses. He would have given us even more, but it was getting close to midnight, and we wanted to save some of the fun for his new girlfriend, Erica.
So, at 11:15, we called it quits, at least for the time being. I got a warm washcloth and cleaned up the mess we'd made. I even changed all of the bedclothes, which was difficult without unlocking the handcuffs that secured our sexual prey. Then Chris and I got dressed, kissed Matt good-bye, and left the apartment, leaving the front door unlocked so that Erica could let herself in at the arranged time. We then headed down to Chris' office where the web servers were ready to stream Matt's and Erica's hot 12:01 sex video to our waiting pay-per-view subscribers.
Of course, if you've followed the news on the betting pool website, you know the rest of the story: At 11:30, Matt's vengeful ex-girlfriend, Nicole, having been freshly dumped by her prick of a fiancé, showed up at our apartment, let herself in because we'd left the door unlocked, and, upon finding Matt naked and bound on the bed, decided to have her way with him and ruin the vow he'd undertaken---literally in the eleventh hour. Of course, this interloping bitch had no idea Matt had broken the vow several hours earlier, and had then proceeded to have the best sex of his life in ways he'd never dreamed of before.
Worse than that, however, was the fact that when Erica showed up for her "date" with Matt at 12:01, she arrived just as Nicole was leaving. A bitchy exchange followed, and Erica walked out the door without ever even discovering our hero in the back bedroom. As a result, our would-be profit venture of beaming their steamy sex to a paying public was shot to hell. In the following days and weeks, we had to pay back the advertisers and refund the cash to all who subscribed.
The thing is, Chris and I didn't even care that our money-making scheme had gone awry. Why? Because the sex had made it worth it. The lesson my horny roommate, Matt, had taught both of us was this: If you deprive yourself of sex for even a little while, you stand the chance to reintroduce it in your life in new and exciting ways you never would have thought about before.
As we sat at Chris' place at 12:30 that evening, thinking about all that had transpired, it suddenly occurred to me that I had had sex in the very same room we had been filming all along.
"Chris, baby," I asked. "How long is the loop on that digital tape?"
"Six hours. Why?" Then his eyes grew wide. "Shit, we've got the whole thing on video!"
"Yep. Good thing we didn't tell subscribers to log in any earlier than they did."
Chris rewound to the 7 o'clock hour, when our three-way interlude with my studly roommate was just getting underway. "Damn," Chris said, whistling softly. "It's really too bad things didn't work out with Matt and that girl. You know, he's a good guy. He deserves to be happy."
"Happy? Fuck that," I snorted. "We made him as happy as he's ever been."
"True, true." Chris pondered this thoughtfully, then perked up. "Shit, and you know what? He's still cuffed to his bed back there. We better go let him get up."
I laughed. "You're right!" I slapped him playfully on the back as we headed for the exit and began walking up the street toward my apartment. "And once we uncuff him, there's a lot of new positions he can learn!"
"Right on!"
Our hunch was dead-on. After being released from his bonds, and taking time to stretch his sore muscles and put the unpleasantness with the two women out of his head, Matt was more than ready for sex...LOTS of sex. As much sex as we could give him, that night, and the next night, and several nights after that.
Sadly, on Day 50, Matt went back to Erica, and to his more-or-less hetero stud lifestyle--but with two significant differences. The first difference is that instead of many women in his life who were occupying his attention, there was only one. The other difference was that, his roommate now had a boyfriend: Chris.
Chris and I still fuck every chance we get. To this day, Matt hasn't joined us, but we know he can hear us every night through the wall. And some nights, I wonder if it makes him jealous at all. Do you think...?
What do you think? Feedback and suggestions? backlash29@hotmail.com
My other stories are "Ryan's Hole" in Gay/Celebrity, "Cup of Joe" in Gay/Authoritarian, and "Buttsex Junkie" in Bisexual/Beginnings