Sorry for the long hiatus. There has been a lot going on. Thanks again to all of those who have written, and those who have been bothering me for a new story. This is a good one from last semester. Back to the true, no more fantasy like the last one for a while. Please keep writing.
These stories are about some of my exploits since going back to school for a masters degree. I have been bi since I was in college, but arriving to a huge Midwestern campus with an endless supply of hot boys has put a spike in my sex life. All the stories are true, some details and of course the names are changed. In a few cases, I have added a detail from another event for dramatic purposes, like putting something from a subsequent encounter into the first encounter I describe. I welcome feedback, and particularly would like to hear from guys in school. Of course standard disclaimer: if this type of story offends you or is illegal where you are, hit the back button. Enjoy.
Straight Boy
This is a story I have been looking forward to writing, but some of the others seemed sexier, or something happened to make them fresh in my mind. This was perhaps the only truly straight guy I have been with, and I was proud to be what may be his only gay encounter ever. Frat boy may be in the same category, we'll see. The difference between them is I think frat boy already knew what he wanted, it was just a question of finding an opportunity and letting it happen. This other guy, Jason, was unsure about whether he wanted to do anything at all.
He had answered one of the craigslist ads I had put up early last semester. It was one basically looking for str8/curious or inexperienced dudes who wanted to meet a bi guy with a little more experience to learn some stuff. Jason emailed me a couple weeks after I had posted it, which told me either he was searching craigslist, or had been screwing up the courage to email me. Anyway, it started off really slow. Pretty soon we were IM'ng and talking about all kinds of stuff. He basically was curious, had just gotten out of a long term relationship, and being new at grad school, wanted to see if he was into guys at all. He had had some suspicions, and had looked at some gay porn, but didn't know if it was just a fascination, or something he would like. I could tell he was scared that he would like it.
I talked him into taking some pics of himself, which he did. He had an awesome body. I found out he had played varsity soccer at his undergrad, so that was just the year before. He still played on a semi- pro team in the big city an hour or so away. I sent him pics, and we talked every day, often for a long time. He finally sent a face pic, and was a very handsome/cute guy. We graduated to talking on the phone, and he seemed like a really good, sensitive yet cocky guy. He loved to talk about his conquests of women. I do too, as well as my conquests of guys. I told him there was nothing to worry about. Liking sex with guys doesn't mean you like it less with women, it's a totally different thing. I would describe hot guy sex, and all kinds of things he probably hadn't thought of. As you can tell, I am good at describing sex, and he would freely admit to cumming once or twice during one of these phone calls.
Finally, we were IM'ing and texting one night and he said he had to come over. I actually didn't want him to because I had had some drinks with friends earlier in the evening and was pretty tired. I also worried my dick would be a bit problematic since that does happen to me sometimes when drinking. I wish I was 18 or 22 again when no amount of alcohol would affect an erection. Sadly, a few years later, that is not the case. I reluctantly agreed, and he showed up within 10 minutes. He was even prettier and hotter than his already awesome pics had suggested. He had a sort of wicked but shy smile, and very classic American heartland good looks. He was slender but very toned, and had a sort of jocky walk with his chest puffed out a bit. It was still warmish out at this point in the year, and he just had on shorts and a T with a light sweatshirt. He was visibly nervous, but we had talked enough that conversation started easily.
We sat on the couch and talked about this and that. Despite my worries, after seeing him, my cock was at full mast in my sweats. We chatted about school and etc and whatever else you talk about. To my surprise, within a few minutes, his hand had snaked onto my thigh and then crotch. I really shouldn't have been surprised, it was he after all who had insisted on coming over! He must've just gotten himself worked into a lather thinking about cock, and was here now to get it. I grabbed his crotch too and should have known by the prominent pointing bulge that he wasn't wearing undies under his silky shorts. He pulled my dick out of the waistband and took a tender then tight hold of it. I assumed this petting would go on for a while. Usually with a virgin you will paw at each other's dicks for an hour or more before anything else happens. Not this time. Without warning, Jason leaned over and took the head of my dick in his mouth and began sucking on it viciously, while trying to wedge his lips further down the shaft.
I was surprised to say the least, but got into it immediately. For the speed with which he started sucking on it, the hard and fast treatment Jason was giving my dick, and the fact he had never sucked a penis before, I was amazed at how good it was and that I hadn't felt a single tooth! I started encouraging him. "Fuck yeah! That's so good! You wanted that bad, huh!? That dick taste good? Feel good!? Hell yeah!" I started massaging his head and ears as he slurped on my cock. After a couple minutes, I eased him down onto the floor, and got my sweats off at the same time. He was now feeling my muscular thigh with one hand, working my nuts with the other, and eagerly working my cock like a pro. I was certain this was his first time, but goddam, he was good at this! I could feel his tongue all over the bottom of my dick, especially when it was mostly out of his mouth with just the head in. When he went back down on it, he was taking almost the whole thing, and I could feel my piss slit bumping on his throat hole. This guy had been really repressed! He must have been thinking about this moment for years. And now here he was, on his knees trying to suck my cock right off. I actually felt the signal I was getting close, and knew I had to change things up a bit. "Let's go get comfy," I said, lifting him up by his arm. It was like he didn't want to let my dick go, and gave it a last few desperate sucks.
We went back to my bed. Standing next to it, I brought him in for a long kiss, with one hand behind his head pulling his lips in tight, and the other one exploring his rock hard tight little soccer butt. I pushed my hand in his waistband and grabbed one if his cheeks, making him moan. I let my fingers roam into his crack, and lightly traced it as low as I could reach. I turned Jason around and hugged him close to me. I pushed his shorts down and laughed when his dick broke free and slapped against his belly loudly. I let my dick rest in his crack and rubbed his chest lightly, making him shiver. I tickled his nips making him jerk, and slowly worked my hands down his six pack, tracing his abs to just above his cock. Jason was breathing heavy. I slowly pushed one hand down the top of his dick, bending it down, until I caught his plump head in my hand. My other hand sneaked down and took a firm hold of his plump balls in their big loose sack. I rolled the big nuts around in my fingers as I twisted my other hand on his head. He was really leaking buckets now, lubing up his own dick nicely.
I worked his cock and balls good for a minute, then backed away, and took my hand massaging his nuts and pushed it between his legs, grabbing the balls firmly from behind, and pushing my hand up into the prominent firm lump under his sack. Jason moaned loudly and went a bit weak in the knees. I continued to massage his balls with my fingers while I jacked his dick and let my thumb run over his head and pee slit, now super slimy with his pre. I let my other thumb range around under his nutsac. Jason really did have a very prominent taint, with an almost sharp ridge to it. My thumb worked across his hole a few times, dropping into the deep little depression there. I was getting pretty worked up too by this point. I pushed Jason over onto the bed and flopped down next to him. There was only one thing on his mind though! As soon as I released him onto the bed, he immediately hopped down between my legs and started sucking my dick again. He was on a mission!
I figured now I better just let him have what he wanted. He had probably been imagining that huge creamy explosion for years months and days. That's probably why he invited himself over: he finally worked up the nerve to suck a cock until it shot its hot load in his mouth. Jason had probably watched this exact thing on the internet a thousand times, and was now going to make it happen. I let him go to work. He was bobbing up and down as fast as before, and still amazingly keeping up some pretty damn good suction. I toyed with his ears a bit and started thrusting into his mouth a bit. He was taking it pretty deep, but I was pushing it a bit deeper now and then, making him gag a little bit, but resulting in some more enthusiastic sucking each time. I was in heaven, looking down at his cute face and twinkling eyes. Despite being a college grad, it still looked like he didn't shave, maybe just a bit above the lip and the sideburns. Jason was looking right at me with his bright blue eyes. It was a look of lust, but also approval, the 'am I doing ok coach?' look. I knew I was getting close. He had probably sucked me on the bed for at least 15 minutes, never losing his pace or enthusiasm. I didn't know what to do about my cum. He had told me many times how much he wanted to suck a dick, feel it in his mouth, etc, but had never mentioned where the sperm went in his fantasies! I decided I'd warn him.
"Dude, that's so awesome! So awesome. You sure you haven't done this before!? (laugh laugh). Dude, you're going to make me cum!" With that, Jason picked up the pace, and his hand went up to knead my balls. I could feel it coming pretty quickly. "Dude, I am going to cum!!" I said, a little before it was actually going to happen. To my delight, but not surprise, he went even crazier on my dick. He wanted that hot goo bad! I didn't disappoint: when I felt the cum rising up from my nuts, I arched my back, let out a cry, and tried to make sure just my head was in his mouth. The first jet felt big and strong, and made him flinch a bit when it probably hit him hard right in the tonsil! It was followed by about four equally strong pulses of man mustard, and probably six or so little ones. I didn't know what to expect from Jason, I hoped he wouldn't be freaked out. I shouldn't have worried. He went back to sucking as soon as I was done cumming. I could actually feel him swallowing with my dick. Now, I am really sensitive after cumming, and don't usually like my dick touched for a minute, but I wasn't going to burst his bubble. He was still going strong, and my dick was still hard. He was sucking as hard as I have ever felt, like he was trying to get more juice out of it.
I finally eased my dick out of his mouth. I pulled him up next to me and hugged him close. "That was so freakin awesome bro!" I said.
"Really?" Jason replied.
"Yeah dude, the best. I can't believe it. That was so awesome." His eyes lit up and he smiled. I reached down and found his dick. It was as hard as steel, and now a total mess of precum. I began jerking it slowly, making him close his eyes for a second and sigh. I had never seen anyone so horned and erect from giving a bj. He was about to pop! I hopped down the bed a bit. While I jerked his dick, I got my head between his smooth ripped thighs and began to lick his sac. I nudged his legs and he lifted them a bit. Now I saw close up his taint. It was like a small mountain beneath his sac. Smooth, with that sort of goose-skin texture, and a perfect line running down the center. I gave it a few licks, and sort of pushed on it with my mouth, making him moan again. The taint was so pronounced, that it made his hole like a little pit. His hole, that I now saw, was a smooth pink little circle down in that funnel-shaped depression. His whole ass and crack was totally smooth, as was his loose ballbag now smooshed on my forehead. Jason was writhing around and moaning and just saying all kinds of things, 'yes, oh, fuck, so good, damn'. He was in a horny dreamworld.
I pulled back up and let his legs down. There was so much pre on his cock, it felt like he had already cum, but I knew that was still a minute away. Using my last twisting motion on his dick to try to wipe away some of the slime, I replaced my hand on his dick with my mouth. Jason let out a long low moan and bucked his hips involuntarily. I knew this would only last a moment, so I went for it as much as I can on a pretty hefty-sized dick. I licked the head furiously, dug my tongue onto the piss slit, and went down on the fat cock as far as I could till I felt a little gag. I concentrated on the top few inches and went up and down as fast as I could. His leg was quivering and I knew he was close. I kept it up a few more seconds until I felt his cock swell in my mouth. I pulled off quickly, but not before the first little half squirt of sperm shot in my mouth. My hand was already on his dick and I jerked the next eight or so jets all over his smooth chest and neck. One even landed on his face. I didn't like getting cum in my mouth, but this was forgiven. Jason probably had no idea he was about to squirt and was so absorbed in horniness he probably couldn't have warned anyway.
I laid down next to him. He was panting and covered in a sheen of sweat. I scooped up some of the bigger globs on him with my finger, and put them to his lips. He lunged and took three of my fingers in his mouth and sucked them wildly. I fed him some more of his spooge as I held him. After a few minutes, Jason looked over at me and just said "fuck me. Now. Fuck me, I need it."
I laughed a little, but a few moments later he repeated himself. "Easy tiger," I said. "One thing at a time, take it slow!" He protested and said he really wanted to. He reached down and grabbed my dick, which had been very hard for a while. Jason was begging me to fuck him. "Dude. You want your first time to be special. Take it slow. I want your first to be awesome, and I am too tuckered out and it is too late to do it right!" Jason reluctantly agreed. He was still lightly stroking my dick and fondling my nuts. As if a flash had hit him, he jumped up out of my arms, and was between my legs in a heartbeat with his lips firmly around my dick. As I watched Jason eagerly work another load out of me, I smiled, not believing that this guy was such a horny devil! For a guy who took a month of daily talking to convince fooling around with a guy wasn't going to make him blind, he sure was a fast learner. I couldn't believe how hungrily he had taken my first load, or how he begged to get fucked. He had told me before that he would have to work up to getting a dick up his rear. So much for that! The BJ was longer and a little slower than the last one. I could tell he was working on his technique and tongue action, so I made sure to give little compliments when something felt really good. After a good while, I felt it building, and gave him no indication as my hot load began to shoot into his mouth. When I was done, Jason looked up at me, opened his mouth, and showed me his mouth full of cum. He then swallowed almost theatrically. Hot damn! He must have seen that in a porno or something. Fucking hot.
Jason left not too long afterwards, it was pretty damn late. I went right to sleep, happy and drained. The next day was Friday and in the afternoon Jason called. We talked for a bit and he said how much fun he had had, and how it was great to finally meet me in person. I told him all the same, and that he was such an interesting guy and hot stud. Obviously, he was over in about 15 minutes. This time when he walked in the door he virtually attacked me. He was just wearing shorts and a tank, which were on the floor in a few seconds. He was on his knees immediately, tugging my shorts down. When my almost hard dick sprang free, he started sucking on it frantically. My shorts fell down and I stepped out of them. Jason had one of my asscheeks in either hand, pulling himself harder onto my dick. After a while, I moved us back to my bed. Jason immediately dove for me dick again, and I didn't try to stop him! I couldn't believe this guy who had never done anything with a dude until yesterday was such a cock junkie.
Eventually, I got him swiveled around on the bed so his dick was up by me as he worked on my dick leaning down over me. It was a new angle for him, and my dick was going a little deeper than it had before. Meanwhile, I could play with his dick and balls from between his legs, and work a finger up towards his hole now and again. As I jerked him and tugged on his nuts, Jason was leaking like he had the day before, with strands of pre dripping off his dick. I worked his nuts pretty good, and pushed hard on his big taint, making him moan onto my dick as the pressure kinda forced him further down on it. After a while, I pulled one of his legs over my head so his balls were directly over my mouth. I started to lick and suck on them, and to nibble and lick his taint. This was driving him pretty crazy, and he was sucking my pole hard and fast. It seemed clean and soapy smelling down there, so after a bit, I reached up and grabbed him by his hard abs, and pushed him forward while pulling him down so his hidden little butthole was within reach.
I had my hands around his waist from below, and tugged him down a bit, letting my tongue range around his big smooth taint. Finally, I let my tongue drop off the back edge of that little mountain and into the deep little recess where his hole was. Because of the little round funnel shape around his rosebud, my tongue slipped in and automatically hit its target. Jason gasped and I could feel him moaning or saying something on my dick. At least the shock didn't make him bite my pecker! I licked all around his hole, and up the crack the other side. Returning to his hole, I tried to push my tongue deeper, but no matter how much pressure I used, that tight little vice-like hole wouldn't open a millimeter. Jason was still giving me incredible head, but had slowed a bit as he took in the new feelings coming from his rear.
After a good 15 minutes of this, I got out from under him and pushed him over onto his back and straddled his chest. With his head on the pillows and propped on the wall, I pushed my swollen red cock into his mouth as he looked up at me with a smile. He was trying to work my dick, but my facefucking was winning. I didn't go all the way in, but almost, and he was gagging a little with plenty of saliva coming out the corners of his mouth. I jerked his dick behind me, it was hard as a rod and leaking more than before, damn! I knew I was getting pretty close, and after a minute or two of really fucking his skull hard, I pulled out so my dick was resting on his bottom lip and began to fire huge gobs of sperm into his mouth while he worked the bottom of my head with that strong tongue. As I came, I was still jerking him, and before I was done squirting, I felt his dick get even harder, and a bit splash of cum hit my lower back. I had shot quite a bit straight down Jason's throat, but like before, he showed me my spooge in his mouth and swallowed it all. I got off of him and was kneeling next to him. He scooted around and began to lick his cum off my back and from the top of my ass crack where it had dripped.
We cleaned up a little, and Jason had to go, he actually had one more class or meeting or something that afternoon. He said he had a soccer game the next morning an hour or two away, but would try to hang out later. I had plans for that night, but would just be studying all day so sounded good to me. We had a nice long kiss by the door, with me working his ass good and getting in that nice crack. We were both boned again of course and our boners were wrestling through our shorts as we kissed. I went to the gym, my dick embarrassingly hard the whole time. I should have put on a jock! The next day I woke up a bit hungover, but got down to studying pretty quickly. Time somehow sped by, I got a lot done, and was just watching a movie, my dick hard of course. It was midafternoon sometime, when there was a knock at the door. I was surprised when I opened it to see Jason standing there in his soccer uniform. I had assumed he would call, but I guess he came straight from his game. He looked hot as could be! Hair mussed up, a bit of dirt on his legs, but his tight nylon shirt and shorts showed him off in all the right places. The shorts were tight enough that I am sure he had a good bulge during games, but of course now he had a lewd erection in them. I have talked about how I like dudes in sports uniforms. I had told Jason this too, about when I played soccer in high school and at the start of college that I could barely concentrate because of the hot guys in those smooth shiny uniforms. He probably did this on purpose!
Anyway, I got him inside and we started kissing. Well done my boy, he had found time to brush his teeth, good planning! I was groping him all over as he was trying to get my sweats down and get at my dick. His pert toned ass felt so good through those shorts, and finding his abs and six pack through that slinky material made my dick even harder. I pulled his shirt, still a bit damp with sweat, up over his head and revealed that smooth ripped chest and stomach. I gave his salty nips a few licks and nibbles, and moved up to kiss him again, while working his ass hard. I pulled his shorts off, and was happy to see some hot compression shorts, but truthfully a little disappointed he didn't wear a jock. No younger guys seem to anymore. "You need a shower dude!" I said. "I do too." I went in to the bathroom and turned the water on. It takes a good while to get hot, so I went back out and pulled his compression shorts off, giving his bare ass a few spanks. We kissed a bit more, and I tugged on his big loose nuts and gave his dick, leaking like a faucet of course, a few nice slow pulls.
You know my shower routine, but this one was hot because I knew it was going to be the first time Jason had ever been penetrated. We were joking and playing grab ass as we soaped each other up. It actually could have been in a gym shower in high school after a big win or something. After we were all soapy, I turned Jason around to face the wall away from the nozzle. I gave him sort of a sensual soaping on his back, and then reached around to his front, and traced his abdominal muscles and abs down to his dick. I reached between his legs and got his nuts and worked them roughly while I stroked his dick. I let my hand slide off his nuts again and again, tracing through his ass crack, circling his tight little hole, and coming up to his tailbone. Jason seemed to be getting weak in the knees and was moaning as I worked his nuts, cock, and crack. When I would circle his hole with a soapy finger, he would push back on it a little bit. Slut! One time as my soapy finger circled his tight little tunnel, I kept circling deeper until I was pressed right against the closed little hole. I wiggled it a little and pushed a bit harder as Jason pushed back a little. In a few seconds, my finger pushed in to the second knuckle, getting a gasp and moan out of Jason.
With one finger in and probing Jason's tight little chute, another was just a matter of time. Pretty soon Jason was leaned against the wall pushing back on two fingers while I jacked his dick. I replaced them with my thumb, which is my favorite because it hits the prostate perfectly at that angle from behind, and I can squeeze the taint with my fingers and lift up, making him feel like he is suspended from his butthole. Jason was going to be a grade-A fuck. From the very start he was taking it all and wanting more, and I could feel him working my fingers with his ass muscles. For such a toned guy, maybe he had good ass strength too! With my thumb on his prostate I could feel him buck a little and I thought he came, although it was difficult to tell with all the soap and precum on his dick. "Did you shoot dude!?" I asked.
"A little I think. Couldn't help it," Jason said almost apologetically.
"No worries dude! That's hot!" I thought it was a good sign Jason had orgasmed from having his hole worked. Maybe he really was desperate for it! He had after all begged me to fuck him that first night. I worked his hole a bit more and then pulled my thumb out. I gave him a surprise shocker with three fingers this time, but only for a few seconds. He had had his foot up on the side of the tub to give better access, but now I brought it back down, and got his hands up against the shower wall. I pulled his waist down so his knees were bent a bit. He was a couple inches taller than me and I had to get his ass level. His buttcrack was still a soapy mess, and I dove in with my dick, riding that deep narrow ass valley good. Every once in a while I would stop with my dickhead over his hole and give a little push. He would push back, but only once did my head slip in for a second. He was just too tight, even with all the finger fucking I gave him. We had probably been in the shower for more than a half hour, I was totally wrinkled. We rinsed off and got out, dried off and got in bed. Predictably, he went right for my dick and I let him suck it for a few minutes. Finally I rolled him on his tummy, and pulled his legs apart, bringing his pink little hole into view. I gave his crack a long lick from end to end and then dived onto his hole. Sucking, licking, nibbling, everything. With Jasons' hoop a little looser, my tongue could make a little progress in there. I ate his ass for a while till it was all wet with my spit.
I climbed onto his back and put my dick in his crack. I slid it up and down in his slippery ass valley, slowly running the length each time. After a while, I bent my dick down so that it would have pressure on his hole, and when I slid it, would slide down and hit his nutsac. I did this for a while until the spit dried up. I reached for the lube and squirted a dollop on his hole. Now, with more glide power, I could really work it up and down Jason's narrow crack. I turned him over on his back and lifted his legs. Same thing, just slowly and torturously working my dick in his valley, stopping over his hole each time. At one point when I was pushing on his hole a bit, he must have pushed down or relaxed or something, because half my head slipped inside him, drawing a little yelp from Jason and a look on his face of surprise. I wasn't planning on fucking him that day, but this was all very hot. I slid it around in his crack some more and then next time I pushed on his hole I felt him push down and even try to hop down the bed a little. Anyway, it worked, and the first couple inches of my dick disappeared in his tight chute. I left it there for a minute while I jerked his bright red dripping cock. Jason all of a sudden got breathless and was jerking around a bit. With no warning, his cock erupted, shooting big globs and ropes of cum all over his chest, some on his face, and on the pillows.
I scooped some up and fed it to him since I knew he liked this. As soon as he had had some of his own cum, he went straight for my dick again. Tired from my laborious teasing of his hole, I let him go for it, but asked if he wanted me to wash the lube off. He didn't care, and gave me an energetic and increasingly professional blowjob. Almost immediately I was trying to keep from cumming. His tongue seemed everywhere and he kept up good motion and suction the whole time. It probably wasn't more than ten minutes before I grabbed his ears and pumped a huge load into his mouth. We laid down and rested a bit. With my dick nestled in his still-lubed crack, he wiggled his ass and squeezed his cheeks every once in a while, keeping me perpetually hard. We rested and napped for an hour or so, and I must have fallen asleep, because I woke up to a nice bj. I rested on the pillow and watched Jason's adorable face as my dick disappeared again and again between his red puffy lips.
The next day was Sunday, and after brunch and a little Frisbee, it was time for homework. I worked all afternoon until the phone rang, it was Jason. I had figured he'd be tuckered out after meeting up three days in a row, but I was wrong. He said he was nearby and was obviously waiting for me to ask him over, which I did of course. Ok, enough homework for the day, I am going to pop a hot stud's cherry instead. Jason was over in just a few minutes as I was closing my computer and books. It was a bit chillier today than it had been and he was wearing sweats and a tight little soccer jacket in that stretchy material. We got to it immediately. Kissing and groping all over the place. I got my hands inside Jason's sweats and really started to work his tight buns. Pulling them apart, getting in between them, and my favorite, lifting him up by his parted cheeks into a hug, while my fingertips probe and poke his stretched and defenseless hole. I was so hard anticipating what was coming. Jason wanted it so bad, and I had used all my will power not to fuck that perfect cherry hole sooner. I knew the anticipation had built for him too.
While we attacked each other, I got his jacket and shirt off and his sweats to the ground, showing off a cute little pair of boxer briefs. I grabbed his big nuts and hard dick through the fabric. This was all heading one direction, so no need to delay the inevitable. I pulled him back to my bed, ripped his briefs off and we went down on the mattress, making out and grabbing each other's dicks. I got him on his back and went down and gave his hard leaky dick a few good sucks before lifting his legs up and working my way down to his nuts. Jason's hair had still been shower-wet when he arrived, so I figured everything was clean enough, so I dove down for a couple minutes of intense ass eating. He was moaning and writhing around. I stopped, and got up on my knees with his legs still up and back a bit. "You want me inside you? Want me to pop that ass cherry?" I said as huskily as I could.
"Yeah bro, fuck me hard," he replied, sort of pulling his legs further up and exposing his shiny pink hole some more. I grabbed the lube and put a dollop right on his hole, pushing some in with a finger. I greased my dick up and made contact with his opening.
"Relax dude, push out, I'll be gentle," I whispered. I bore down a bit watching my dickhead push his rosebud inward a bit. I let off and pushed a glob of lube into his hole as I repositioned my dick. With some mini thrusts and rubbing motion, along with more pressure, my head slid into Jason sharply, making him take a quick breath. "You ok babe?" I asked. He nodded and I continued my entry. With little strokes, I worked a few more inches in until I hit some barrier. This would be about as deep as my fingers had been, so we were entering uncharted territory. I asked him how he was doing, and he said great, so I figured I could go in a bit more. It took some good thrusting to get past this barrier, but once I did, the rest of my cock seemed to sink slowly but steadily right up his chute until I felt my pubes mashed into his balls. His ass was so hot and tight, I felt like cumming right then. I left my dick all the way in him for a minute and then slowly pulled out before pushing back in a little faster.
Jason was moaning as I long stroked him. His ass was so spongy and tight, I could feel it on all parts of my dick all the time. I pulled out and quickly put a rubber on, lubed it a bit, and shoved back in. I picked up the pace a little bit and started giving him a bit more force behind the pounding. With no protest after a few minutes, I started giving him a bit harder and faster fuck. I alternated between pushing his feet all the way down next to his head so I could kiss him, to holding his ankles high and as far apart as they would go to give him that stretching feeling and open his hole more.
I was sweating quite a bit and Jason was just moaning and talking a bit dirty once in a while. Mostly silly stuff like 'fuck me, pound my ass harder, use my pussy, fuck me, you like my ass?' Still, it worked for me! It had probably been a good 20 minutes and I had gotten close a few times. I pulled out and flipped Jason on his tummy like he had been the day before. I pushed back into him fast, and started hammering his ass with my arms around his shoulders and clasped behind his neck. I was really drilling him now and Jason was working his ass perfectly in rhythm. I should have known he was also fucking my mattress because all of a sudden he started to spasm, and was obviously shooting a load. I felt his ass tube go crazy on my dick as he ejaculated. I almost came right then.
I was getting pretty close anyway. I flipped him over on his back again, wrenched his legs back and apart, and speared his open hole in one hard thrust. The pause in fucking had made my orgasm subside for a bit, so I just concentrated on giving him a good hard screwing for a while. I build a good speed and rhythm up and Jason was just moaning with a big smile on his face. He had stopped working his ass muscles as much, maybe he couldn't anymore. I fucked him like this for another 10 or so minutes and then felt my cum returning. I got the backs of his knees with my shoulders, and really started a hard sprint of a fuck to the finish. I pounded him as deep and hard as I could, not quite as fast as before, but good forceful fucks. After a couple minutes I felt it rising, and gave a couple more hard bangs to the bottom of his hole as I felt the condom fill up deep inside Jason's guts. I left it in for a minute while we caught our breath and then pulled out. I dumped the big load onto his still-hard dick, and began to jerk him. With my other hand, I felt around his hole. It was still open a bit, but not much, and felt nice and puffy. He was starting to jerk again like he was going to cum. My cum-lube on his dick was getting all frothy, and I jerked him faster. I felt he was getting close, and shoved three fingers up his lubed hole. A moment later he bucked and shot another load all over his chest.
We got in the shower and washed each other, but with not too much playing around. The nice thing about apartment buildings is that the hot water lasts forever, and we stayed in for a while. After a bit, we were both hard again of course, and were playing with each other's boners. Jason got on his knees in the shower and started sucking me. It was heaven with the water going off my head and shoulders and Jason with a good grab on my butt cheeks for stability sucking away. After a few minutes, I pulled him up and told him to bend over. I wanted to look at his hole. It had mostly closed, but was still a bit puffy. When I pushed my finger to it, it swallowed it whole! Haha. With him still bent over, I soaped up his lower back and butt. Once his ass was all soapy, I rubbed my dick up his crack from his balls until it found its mark and pushed in. Jason let out a long low moan. I fucked him good for a while, as quickly as I could without losing my balance on the slippery shower floor. Surprisingly, I actually felt like I could cum after a little while. I wasn't going to spunk his ass after using a rubber to pop his cherry, so I pulled out, spun him around, and pushed him down again. He took my dick in his mouth and really went to town. A short bit later, I was filling his mouth with a nice load as the water ran down his forehead and into his mouth, mixing with my nut.
With that, we got out and dried off. He hadn't been there too long, but we were both knackered. We got dressed and I got some beers. We talked for a while, and it was nice. Since we met in person, it had been solid sex, and I had forgotten how easy he was to talk with, and how interesting and witty he was. We actually took a couple shots, and were having a good time with some more beers. Finally, after a couple hours it was time for him to go. He said he'd see me tomorrow, which I assumed he would! All next day, Monday, during classes, he was Im'ing and emailing me. Talking about how hot the day before had been and how his ass felt all tingly like it wanted more. And then some real dirty talk! He said he had been boned all day, and I made him take a pic in the bathroom and send it. I was in the library boned up myself and sent him a pic. I had a break in the late afternoon but a busy evening, so told him to come right over when he got out of class. He was there about 5 minutes after his class ended and came inside.
After the dirty talk all day, I wanted to give him a real fast hard one. When he got inside, we started making out as usual, but I broke it off and told him to strip. He did quickly and I grabbed him and started fingering around his hole. "Bend over, let me see your pussy," I said. He did, and I gave him a few spanks. I got out of my jeans and was hard. I went and grabbed a condom and lube off the nightstand and came back. I pushed him over the arm of the couch and squirted some lube onto his now-quivering hole. "Mmmm, that pussy's all tight again!" I hissed, "Like a virgin again." With that, I put my cock at his opening and pushed in all the way. Jason let out a moan for about ten seconds. I started nailing him pretty hard, and he was letting out little yelps and cries like 'fuck me! Break my pussy, cum in my asscunt'. He was such a nice wholesome guy, it was kind of shocking to hear him say this stuff, but hot. Nevertheless, to give him something new, I picked his briefs off the back of the couch and stuffed them in his mouth. Jason must have thought that was hot, cause he really started bucking and pushing back into my dick.
I fucked him hard over the arm for a while, then pulled him over onto the cushions and forced his legs back up almost behind his head so his ass was pointing up and hanging open. I pushed back in fast and hard, starting with my dickhead about six inches from his hole and ending with me balls deep and my pubes smashed into his crack. He was so cute with his bright eyes looking up at me, his briefs hanging out of his wide open mouth, and his nice big dick leaving pre all over his folded-up tummy. I was really nailing him hard now, and giving him some good hard spanks every once in a while. Every time I spanked him, he would jerk and his ass muscles tightened...it was a good little trick! After a while of this, his breathing grew heavy. I jerked his dick once or twice and was rewarded with a big load that shot all over his neck and face. The feeling, sight, and smell of Jason's big orgasm sent me into overdrive. I was basically hammer-fucking him back into the sofa cushions. It had probably only been 15 minutes since I first pushed into his tight hole, but it wasn't going to be much longer. I was losing traction with my bare feet on the carpet, so kinda crawled halfway onto him as I pounded away at his now well-used pussy. At one point, I don't know why, I pulled all the way out, leaving his hole winking open and closed, and dropped a big loogey that fell straight in. I mashed it in with my dick, and kept up the assault since the end was near. I leaned down to his head, mooshed down between the cushions, and gave him a big wet kiss while I jackhammered his asstube for the last 30 seconds. I usually like to fill up a hole so the dude can feel me cumming, but this time, with Jason's body crammed down into the sofa, I pulled out at the first spurt, ripped the rubber off, and came all over his body and face. The last two little spurts fell right on his hole.
We were both out of breath and sweaty. Jason sat up on the sofa, pulled his undies out of his mouth, and leaned over to take my dick. It was a bit cummy from the first shot inside the condom, and he expertly cleaned it off, and kept sucking for a few minutes. Finally he stopped and sat back. "Damn that was fuckin hot!" he finally said. He was going to the gym before he had to do some things in the evening, and I was already running late for a meeting. He didn't bother cleaning up and I teased him about guys smelling sex on him at the gym and maybe taking his ass for a spin too. As I sat in this meeting, and then another evening class, I thought about how awesome it was I had found Jason. He was cool, fun, interesting. A total hottie, and obviously a very horny guy. I was thinking if this keeps up every day, that's not the worst thing! I jerked off later than night thinking about breaking in Jason's previously impenetrable ass. I shot a huge load right as I was thinking about the first time I came up his rear.
But, it didn't end up turning out that way. I didn't hear from Jason the next day, which wasn't too odd, it was a busy class day for me too. I got an email from him the next day which said he had enjoyed every minute of the times we had together, but had thought about it and decided he was straight after all. I was pretty bummed. He had been so enthusiastic and horny to try everything. He may be something, but straight sure wasn't it. I emailed back and said I was sorry, was it something I had done? I was afraid maybe that last fuck had freaked him out, maybe I had gotten carried away. He said no, he liked me a lot, he just didn't think he was into guys. I figured I'd better let him think on it for a while. He was probably confused. That's unusual to go from never having been with a dude at all, to five days straight of hot sex. Might have worn him out! A week or so later, I called him to see how he was doing. He sounded happy to hear from me and we chatted. I finally brought it up: was he really not going to ever get with a guy again? He admitted he had boned up a hundred times thinking about what we did together, but was truly not into dudes, he had just wanted to try it out. I thought he probably was freaked out by how much he liked it. We didn't talk for another week or so until I saw him in the gym. We talked about this and that, and Jason said he wanted to have a beer that night. We met up at a place between our apartments and had quite a few drinks. He had said drinks only, no sex, but after a number of drinks, he was rubbing my leg under the table, and slipped his shoe off and put his foot in my crotch. We paid up and set out for my place. Jason kept grabbing my crotch and ass on the walk, and I did the same. Once the door closed, he was all over me in drunken kissing and groping. We were in my bed in a few minutes, and I gave him a nice long slow pounding on his stomach. The booze kept my orgasm at bay for a long time, and it really took some good long intense in-and-out before I finally pulled out and burped a huge load on the top of his ass crack. I scooped it and fed it to him, and we fell into a nice sleep with my slimy cock wedged between his cheeks. He woke up sometime in the middle of the night and got dressed and said so long.
After that I emailed him and said it was fun, and didn't he think he wanted to hang out regularly. Still not, he wasn't into guys. So that was kind of our relationship for the rest of the year. Every once in a while, we would meet up for "drinks" and I would fuck him. Never could figure that one out, but I was happy to get to use his hot body and tight hole once in a while. He was such an awesome and nice guy, I wished that one could have turned out differently. Oh well.