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Unless stated otherwise, I write about real experiences. Some of the details have been slightly embellished to accommodate my wild imagination.
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There was this guy at work, a tall, fit South African guy (we'll call him MJ) who was liked by everyone. He was about 6'1" with short, floppy brown hair and brown eyes and flawless skin. MJ was quite private, but quite social and active, the kind of person who would talk to anyone and make you feel that you mattered. So I had a little crush on him, of course. We went to the same gym, but never at the same time, which was a pity because he liked swimming and I would have been able to see him in speedos.
After a few months, he announced he had to go back to South Africa because he couldn't extend his visa any longer. I barely knew MJ, yet it still made me sad (a crush is a crush). He was due to go back in a week, so they arranged a leaving do for him and he would go back to London the next day to see some friends and fly back from there, which was lucky for me because I was heading to London to see some family and could give him a lift. He wanted to leave early the next morning and asked if I'd stay over at his place so we could just get up and go - of course I said yes!
So the night went fine, with the usual drinking and prodding questions started and I was sitting near MJ and one of our other colleagues who was asking very personal questions of him. He was quite shy, but she managed to get it out of him that he was a virgin, apparently, and didn't masturbate either (I still don't know how guys don't masturbate, it seems unnatural). She stopped short of asking about blowjobs - I really wish she hadn't.
After dinner and the goodbyes, MJ and I set off to his house share so he could finish packing and get some sleep before the short trip to London. His housemates were in, but he said they would have been out partying so fast asleep in the room next door. Now this is where my imagination started running wild, but I thought I'd keep my comments to myself and not spook the guy I'm supposed to be sharing a room with and driving to London the next day.
He was really neat and had done most of the packing, there were just a few boxes left to pack and it wouldn't take long. I offered to help, so I got to pass him his underwear and swim gear, socks and some Summer clothes before the closet was empty. MJ's collection was nice, but very conservative of course and I knew that the evening would go different to the fantasy that started forming in my head. I asked if he slept in pj's because I couldn't see whether he kept any sleepwear out and, to my disappointment, he said he'd just sleep in the shorts and t-shirt he had already changed into.
"Did you bring anything to sleep in?", he asked, moving a bag into the corner. I was about to say something when he continued with "because I can lend you something if you like." Now my mind was racing, because I was going to say something else, but the thought of sleeping in his clothes was pretty interesting. Ok, it was a turn on, that's what it was. Instead, I said "I'm ok thanks, I brought shorts to sleep in, I usually sleep naked but I didn't want to scare you." The words were out of my mouth before I could stop myself and I could feel myself blushing as he looked at me! "Me too", said MJ, "but not when there's company, unless we're going to have sex of course" and then chuckled. So, that seemed to be that, because he didn't say any more about it. "Where's the bathroom please?" I asked, because I didn't want to change in front of him, for obvious reasons. "Second door down the hall, but you can change here, I can leave if you want me to?" he replied, busy with his backpack, with his back to me. "Nah, that's ok, I'll just change here", which I did quickly because I could feel a semi waking up. It was a warm night and he took off his shirt, still with his back to me and I didn't bother putting one on. I sat down on the bed to hide my, erm, interest as he carried on. He wasn't muscular, but he was beefy and reasonably well defined. I watched his swimmer's muscles move under his olive skin as he moved stuff about, lifted and shifted bags and boxes and got a nice view of his butt straining his shorts as he bent down (sometimes, not lifting with the knees is ok if the view is as good as this).
"Ok, done!" he declared and turned to face me, showing his defined torso (the boy had nice pecs) and it looked great with just that slight sheen of sweat covering it all. You can have the bed and I'll take the mattress. It was a single, in the corner, hidden under a large backpack and some boxes but cleared now. "Are you sure?" I asked him, disappointed somehow that we wouldn't be sharing the double. "I can take the mattress or we can share top and tail, I really don't mind" and of course I didn't expect things to go my way, but you never know. "Nah, it's ok, you're driving so you should get some rest and be comfortable." He took off his shorts, now just down to his loose fitting boxers. And that was it, bed time, me on the double bed with a thin sheet and him on the single, only covered with a thin sheet. When the lights went out, I glanced over to see if I could make out any interesting outlines, but there was nothing to say he was teasing.
He lay there on the mattress, the sheet pulled down to the top of his boxers, one hand behind his head and the other disappearing under the sheet, covering his crotch, probably in his shorts, holding his tackle. He had his face to the wall, so I didn't have to worry too much about him seeing me watching him (and being creeped out). From what I could make out in the faint light, he had very fine hair between his pecs and that fine line of hair from the navel down. One leg was also out of the sheet, so I could see he was pretty well defined, but not like some athletes. It was just nice, toned and flawless. I knew nothing was going to happen that night and there was no way I'd be able to have a wank or sneak out for one, meaning I'd just have to think unhappy thoughts and bear with it, which I did.
The next morning, he woke up before I did and brought me some coffee, still just wearing his boxers, but I could see more of him in the daylight and I wasn't disappointed. That didn't help with my morning wood problem, all I could do was gather up the sheets and hope he didn't notice. "I'm going to have a shower and we'll set off in an hour or so once you've had one, ok?", he said and disappeared out of the room with a towel slung across his shoulder. I thought of having a wank, but I had no idea how long I'd have, I couldn't hear the shower, the door was open and his house mates might wake up. Also, if I'd made a mess, there was nothing to clean up with. Just as well, because he didn't take long. MJ came back wearing the towel around his waist and told me that there wasn't much hot water, so I'd have to be quick - he looked very apologetic. "That's ok, I'll just have a quickie too", I responded and took the clean towel he offered me.
Another problem! I couldn't have a wank in here, have a shower before the water ran out and not get back without looking flustered. I just had a quick wash (and he wasn't wrong about the lack of hot water), dried off and went back to the room with the small towel barely wrapped around my waist, just managing to tuck in a corner. In my hurry, I forgot to bring the underwear and shorts I was going to wear for the drive, so I had no choice - fortunately the shower water was cool towards the end.
The door was slightly ajar and I just pushed my way in, then closed it behind me, trying to be quiet so I didn't wake the other people in the house. As I looked up, I realised he was totally naked and bent over, looking for something in his backpack. Stunned, I took a second to take it all in, the curve of his glutes, the light fuzz between those cheeks, the just visible ballsack hanging free and just the tip of his cock visible too, he was uncut. "Sorry!", I said, "I was trying to be quiet so we didn't wake your friends. I should've knocked to let you know I'm coming in", I think I was blushing again. "I'll just go get changed in the bathroom" now whispering and walking over to the bed where my clothes were spread out. "That's fine man, no need to leave", he said as he turned around. Now I could see all of him and it was a sight to behold. The light caught him on the side and the silhouette of his defined muscles made him look more buff than he was. He had that nice v-shape on his abdomen, he didn't have a lot of body hair but the light tufts he had were in the right places, showing off a young, masculine body. MJ had nothing to be shy about either because, resting on his ballsack, was a fairly chunky cock, totally flaccid. But it was thick and about 4 or so inches, with the puckered foreskin ending the display. I wondered how big it was when he was hard and almost asked.
He caught me looking, so all I could say was "nice cock dude!" and chuckle. "It's alright, I guess", he said and gave it a tug, "not huge is it?". "I don't know, I haven't seen it hard have I?" is what spilled out of my mouth before I could stop myself. "Yeah of course" he chuckled, shaking his head, "but I meant it's not big when it's like this", then gave it another tug absent-mindedly. Were we really having this conversation? So I pushed it a bit. "I think it's fairly average or above, right? I don't think I've seen any bigger than that when they're soft, but I don't remember ever seeing one as thick". He looked down and then looked at me, absent-mindedly tugging and pinching his foreskin, then said "so you've seen a lot of them then?", slightly cocking his head. Now I was flustered (and hard), "well, you know, a fair few, like my step brothers, school camps. I mean, they're literally everywhere right?". I didn't know if I got away with it. But it was the truth, I didn't have much experience with men, so my only sightings were usually brothers or camps. "I'm an only child and I never really looked when we had camps and sporting events, so I wouldn't know. I'm usually pretty shy to be honest, I don't have a lot of confidence, so I keep to myself usually".
He was still tugging absent-mindedly when he spoke, "I've seen a fair few over the years", then chuckled (it was a cute sound), "usually flopping around when guys are walking around locker rooms. But I can't remember seeing a hard one or showing my hardon to another guy, just never happens". He was smiling, he was also about an inch or so longer and now just cupping his balls playfully while looking down at his own crotch. "Have you?" he said, looking up at me and I was totally caught off guard, his gaze moved slowly from my face to my waist, where the slightly undersized towel was just about covering everything. I had it gripped tight at the corners, just above my hardon, hoping I was hiding it in the few folds. "Uh, yeah", I more or less stuttered and I'm sure I was blushing", then "oh wait, you're asking if I've seen them or shown mine?..." If I was trying to play it cool, I was doing a bad job. I'd have slapped my forehead if I wasn't now clutching the towel with both hands and slightly bent forward to try and hide the fact I was rock hard. But he laughed and I relaxed (and breathed a sigh of relief), before he stepped forward and grabbed my towel - he was fast and my grip wasn't as tight as I thought. Awkward. I didn't turn or try to hide it, I just said "morning wood, won't go away on it's own and not with this conversation!" Still awkward, but fuck it right?
He dropped the towel, looked at his cock (he was finally hard too) and then at mine, "you're cut, I haven't seen a cut dick before, you know", and pulled at his foreskin. "Wish I wasn't cut" is all that came out, "makes it harder to wank". Then, "I heard you telling that girl last night you don't masturbate?". He stood a bit closer, "well, she was getting personal and it's none of her business, so I just tried to throw her off and seem awkward so she'd stop. Don't get me wrong, I'm not experienced at all, but I've slept with a girl and I do wank, just don't talk about it". He was gently stroking his cock up, from his balls up to his head using alternate hands, it seemed totally relaxed and conversational, I was the only one being awkward. So I took mine in my right hand and did the same, but rounding my head over when I got to the top, "that's good to hear, I can't imagine not having a wank, it feels great, especially when you're stressed and helps me get to sleep sometimes". He looked me over and then, this is how the conversation went:
MJ: You had one last night?
Me: No way man, I was way to scared! (I laughed)
MJ: Why? I was a bit horny too, but same I guess.
Me: If I'd seen a hardon under your sheets, I might have said something.
MJ: It was there, all the time until I fell asleep. Didn't see one on you either, but I did notice you facing my way. (he chuckled again) But I couldn't tell if your eyes were open or closed.
Me: Um, they were open. I was going to bang one out when you fell asleep, but decided against it because I had nothing to clean up with. (I just shrugged).
MJ: So?
Me: So?
MJ: What now? (looking at our hard cocks in turn)
Me: Well, you up for wanking with another guy?
MJ: I don't think we have a choice dude, we've got this far and the boundaries are long gone! (he hopped on the bed with his back to the headboard and arranged the pillows)
Me: (grinning and crawling over to his side)
We sat at an angle, backs to the headboard, bodies touching. And it wasn't awkward anymore, but it wasn't sensual, if that makes sense. It was just two guys, laying there naked. I didn't get the vibe that he wanted to get to do too much exploring, but the naivety was exciting and I wasn't going to push it.
"We're both right-handed", he said as he gripped his cock with his elbow resting on my belly, "that's a bit awkward, should I move up?". "Nah, this is comfortable, as long as you don't mind potentially getting some cum on your elbow if I finish first". We were both stroking slowly now and I lightly brushed up against his elbow when I hit the top end of my stroke, my head just touching now and again. "I've already got some precum from you it looks like, so I think I'll survive" he chuckled again as he wiped it off on me, but went back to the same position. We were both stroking now, but not very fast. I thought we could push this a bit further, but before I could say anything, he said "your left arm is pinned, that can't be comfortable, do you want to swap?". I didn't, because I wanted that arm on my body. "Nope, I'm good, but if I slide my arm behind your neck, it's out of the way" (and, of course, he'd be closer and lower, so we'd make more contact). "Yeah, ok" he said, leaning forward. I slid my arm behind his neck and he moved his body down to be in a less awkward position. "You sure this is ok, you're comfortable? I feel a bit selfish here, I'm very cosy", more chuckling, but he didn't stop stroking. "Yup, it's actually fine, just ignore my roving hand beside your head, I'm not going to keep it straight", then I gently tapped the side of his head with my palm to make a point. "Built in headrest, nice! Oh, and if you think you're going to shoot first, think again" he said as he sped up his stroke, "loser has to clean up!". He turned his head slightly to the side, away from me and I could see his eyes were closed and he was biting lightly on his lip as he stroked away at a steady pace. His head was now resting, slightly pushing into my palm and his body was moving rhythmically against mine while he ground his hips slowly during the stroke. He might lose the bet, because this was hot as fuck.
So there I lay, holding his head, feeling his breath and hearing very faint moans and breath control, my cheek against his shoulder, our bodies moving slowly together, his arm on my torso, also moving, my cock head and fist deliberately pounding against his arm. I was slightly pulling him in as I was stroking (faster now) because the pressure just added to the great feeling. I grabbed his hair gently as I sped up, then he sped up and we just lay there, wanking. I was probably ready to cum way before him, but there was the promise of a loser cleaning up and I really wanted that job, so I tried my best to control it. "I'm close man", I whispered and tried to sound competitive, "you better get ready to clean this up and I don't mean wiping down with a towel like some loser. If you lose, you LOSE", I was just going to let him make of that what he wanted. He didn't miss a beat, "I hope you're thirsty, because I'M close and I haven't wanked for three days", chuckling again, he let go of his cock for a sec, looked over at me and slapped my hand off my dick. "Reset!", he whisper-shouted, we still had the roommates next door to think about. I just leaned over and grabbed his cock, then wanked him fast, "that's cheating, and cheating gets a beating!". He moved his body and head slightly toward me, so now I had the back of his head (and a handful of his hair) in my hand and his cock was pointing over my way, I had a great view. He let me do that for a while, I didn't know if he'd be shocked, but he closed his eyes and leaned back into my hand, letting me grip his hair gently and doing his strokes for him. "I wasn't expecting that, but it's ok. Also, if you're wanking me, then I win and you clean up, sucker!". He was right of course, but I didn't want him to know that's what I wanted. "Oh shit man, you're sneaky!" I said, then started stroking my own again, fast and furious, same position as before, leaning in a bit harder and at least making it look like I wanted the win. He was already stroking again and I could feel his breathing getting quicker, he was going for it full tilt. "Prepare", he said breathlessly, "to", again with the breathless whisper, straightening his body, "loooooose, ah!" and then his body tensed, his load shooting over his chest, most of it landing on him, some towards his shoulder and a bit hitting my shoulder. Then a second, smaller stream left his cock and landed just above his outie belly button (hot). "So close", I said as I pulled him closer, raised my right hip and shot my load. Not nearly as big or as impressive as his, but my aim was good and most of it landed on him. I flicked the second one over to him as well, just to rub it in.
He chuckled again, "you sly wanker, there's almost nothing on you!". "Well, there's this" and I licked the bit of cum he managed to get on my shoulder, "and this", I scooped up the small puddle on my stomach and rubbed it on his cheek, he just laughed. "Yuck man!" is all he said, but he didn't wipe it off. "Well, since I'm the loser and cleanup is my duty, you should get messy. What towel can I use?", I said, gripping his still hard, dripping cock, but I didn't get up. "Nah-ah, I think you said something about not using a towel dude, and I don't see anything else you can use. Guess you'll just have to suck it up, like literally." He shifted down and put his hands behind his head, closed his eyes and chuckled. I poked at the smear on his face, "ok, starting here then", I did a quick lick at the jizz and got a chuckle for my efforts. I moved from the top down, his right shoulder (clean), his left pec (clean), decided to take extra care at cleaning his nipple, "hurry up man, that jiz is going liquid and this isn't Basic Instinct", though he didn't open his eyes or move. I wasn't going to ruin this, so I eased up, continued down his abdomen, had to be thorough around the belly button (he's ticklish) and finally got everything off his body. "Done, clean as a whistle", I lay back and enjoyed the taste of our juices in my mouth. "Yours too?", he looked down at his body and back at me. "Yeah, a deal's a deal, had to clean it all up right?". "Yeah, but you missed a few spots man", he said and leaned forward, first tentatively licking at a spot on my belly, then giving it a good lick to finish, "salty, but ok, I've never tasted another guy's cum". "Well, lots of firsts today for us then. So where are the other spots I missed?". "Yeah, there's this", he said before grabbing my cock and licking the head once, "and this", he lay back and held his cock (still hard), pulling the foreskin back slightly. "I keep it clean, so you should too", he let go of it and put his hands behind his back again, straightened his legs and closed his eyes. So I took it in my right hand, gently pulled the foreskin back and put it in my mouth, then licked the skin clean, then licked the head clean, then ran my tongue around the inside of the skin - I had orders to be thorough and I wasn't going to disobey when I was given a free pass.
Remembering what he said before, I was about to let go and ask if we should get going, but I heard his breath was getting shallower and he started thrusting his hips slightly. I moved my head down when he thrust up and up when he went down, thinking he was either going to say it's time to move on, or let it run. He did the latter. I swallowed deeper and he thrust a bit faster, breathed a bit heavier, hands still behind his head. It didn't take long this time before he came again and I knew it was going to happen. He put one hand gently behind my head and said "easy cleanup second time around", then his body tensed and he squirted a single, small load right in my mouth. I swallowed and took him deeper, he tensed again, but less powerful and a smaller load got into my mouth, I swallowed again.
"Ok, so the winner gets to blow two loads hey?" I asked as I looked up at his face. MJ propped himself up on his elbows, he was grinning now, looking very satisfied. "Hey man, my first wank with a guy and my first blowjob from a guy, why not, I probably won't do this again, but you were cool, so fuck it. You're still hard", he nodded at my cock. I was sat upright, but on my knees with my legs folded under and one of his legs between my legs. My balls were just resting below his knee at this point. "Yeah, well that was horny and I could probably have another orgasm without trying too hard", it was my turn to chuckle as I said it. "Go for it then, but you're on your own, man, I'm spent", he lifted his leg and rubbed my balls slowly, then he pulled his leg in a bit, the top of his foot tapping on my butt, playfully. He dropped his leg, laying back down and slowly stroking his softening cock. He was still looking at me, kneeling, straddling his leg with my hardon, hand wrapped around my cock. "It's a bit of an odd feeling, just wanking here on my own facing you like this, makes me feel a bit pervy", I chuckled awkwardly, even though I didn't really care, I could happily wank again, sitting on his leg like that. "I know what you mean man, but I'm spent and I don't mind, sorry I orgasmed like that, it just felt too good and I wanted to know what it felt like - it was good by the way". He propped himself up again and it looked like he wanted to say something awkward, "How about I turn over and you can have a wank without feeling creepy, you can cum on my back if you want, as long as you clean up your own mess?". MJ didn't wait for a reply, he just turned over and pushed his other leg between my legs too. "Cum where you want, just remember you have to clean it. And no bum stuff, I've got to draw the line somewhere." So I moved up until the tip of my cock was just over his glutes. If I pulled them apart, I could get a glimpse of his hole, but he had drawn the line, I was just going to push it a bit and enjoy his relaxed attitude without blowing it.
"Is this position ok?", I asked and sat back a bit, now my tackle was resting just below his butt and my shaft on it. "Fine by me, but remember what I said, I really don't want to do butt stuff ok? And give me a massage while you're there, I'm feeling nice and relaxed". Fine by me, of course. And bonus! "Ok, but massage from this position means I'm going to be humping you a bit, just so you know.". "Worth it man, as long as my butt hole stays closed and I get a backrub, you knock yourself out". I put my hands just below his glutes and slowly ran them up and over his cheeks, my thumbs gently prising them apart. I had a free pass, so to speak, so I was going to make the most of it and not rush this gift! I ran my hands up, thumbs spreading his cheeks, then over his butt, to his lower back (my shaft now resting nicely between his cheeks), then up his back (my shaft pressing down harder and sliding forward a bit), and then right to the top (where my shaft had travelled upward between his cheeks, my balls resting over his hole and head and shaft squeezed between my stomach and his butt). I moved back down and repeated the movement up, back down, up, back down a few times until my breathing became heavier. It was a nice feeling and if this were a hookup, I would have slid my cock inside after a few strokes. I was thinking how good that would feel as I continued, wondering if he would change his mind (but I wasn't going to push it). "That's really nice, I like the pressure on my back and the long strokes, massages are usually a bit more clinical" and he was chuckling again, "how's your dick doing? I can feel it's still hard and not getting attention". "Oh, it's getting attention, don't worry about that. Probably more attention than it should. If I'm not careful, I might just blow doing this massage". I carried on, then he said, "well, same rules, but if you blow, you blow, just don't rush this massage because I'm enjoying it" and lifted his hips up as I was leaning forward, increasing the pressure between my crotch and his bubble butt. He did this a few times and synchronised with my forward strokes before he said, "just a little gift to your suffering dick, I hope it felt nice". He relaxed and let me carry on. I explored a bit more at the bottom of the stroke, eventually seeing his hole as I slowed down the start and parting his cheeks a bit more, but I kept the same process going, thinking I'd gone as far as he'd be comfortable with. And I was pretty satisfied myself, also leaking precum but not wanting to cum just yet. I carried on for a while, but I knew I was getting close. "I think I'm going to cum soon MJ, my cock can't take all this teasing any more", I said this playfully, without stopping my strokes and light grinding. "You're ok to stop massaging, I know it must be a cock tease, even I'm getting a semi again. Same rules, but do what you like to get your reward, I'll tell you if you cross the line."
I leaned forward and put my hand either side of his chest, almost in a pushup position, but with my tackle pressed against his butt, then slid up and down a few times. "This ok?", I asked while moving up and down. "Still good", he said as he pushed his hips upward, "I don't like butt stuff, but I think I can get to like this". That almost made me cum straight away. We got out of synch and instead of my shaft sliding up between the cheeks, my head poked right at his hole and it felt great. His body tensed and he stopped, "sorry, timing was out, your fault I think" I said apologetically and pulled away. He relaxed, "close call, I'll let you do the hard work then or I'll end up breaking my own rule. It wasn't awful by the way." Relieved and still horny, I carried on, I had permission after all. "Ok, I'm close man, I'm just going to go for it now. Anywhere I like right?". "Yup, you clean up your own mess though."
I didn't know how I wanted to do it. I could sit up, play with his butt and look at the prize while wanking, maybe cum over his butt. Or I could do what I was doing with the massage, and cum over his lower back, while my cock was sliding in his crack. But I thought I'd try something else. "Same rules, no entry", I said, "so don't freak out ok?". He was so casual about it, "I trust you man, don't make me regret it". I gathered some spit in my mouth and just let it drop from my mouth to the top of his crack, letting it run down. I did this twice and then ran my cock head between his cheeks, down past his hole and back up again. Then I leaned forward, pushed my cock back between his cheeks so when it pulled back towards my body, the tension would keep it between his cheeks and I was less likely to poke his hole. I slid my forearms under his shoulders so I was in a kind of plank position and started moving my hips backwards and forwards, so my shaft was riding between his cheeks. "Interesting move", is all he said. It felt incredible. My circumcised head ran up and down that warm channel, the fuzz scraping at my shaft and adding to the sensation. I was very close and he knew it because my breathing gave the game away. He started moving his hips and grinding a little. "Careful MJ, you're going to break your own rules. If you arch at the wrong time, I'm going to poke you right in the hole and there's enough spit down there to let it in this time", I said it playfully as he arched and I stopped as my tip hit the prize to prove my point. "See?", he dropped his hips and I carried on, getting closer. He did it again and I poked harder this time. "My rules, man, I'm bending them a bit because it feels nice. Just carry on grinding", he said and we carried on with near penetration. He did it a few more times, and every time the tip applied more pressure and he kept it there a bit longer before moving. After the next time he did it and I felt the tip opening him up slightly, but not taking the full head, I knew I wasn't going to last much longer. "If you keep doing that, you might end up taking a load MJ. My head is sensitive and that warm butthole of yours is better than a blowjob". "My rules, you're not doing anything I'm not allowing", is all he said. I carried on and he became a bit more daring every time. After a few more slow, intense thrusts it was too much to hold back. "I think...", I started, but didn't get to finish as his daring finally resulted in my entire head sliding in past that first puckered muscle and he held it there, rotating his hips slowly and whispering "fuuuuuuuck man". Then I orgasmed. My body tensed and my hips thrust forward and I slumped over his back. He pushed his hips backward and my whole cock was inside him now, pulsing and squirting. "Sorry, I couldn't stop it", I said. Still buried inside him, it was warm and felt good and his hips were still moving. And he was moaning and swearing very quietly, still kind of humping the bed. I could feel that muscle tightening and relaxing alternately around my shaft and knew he wasn't finished.
"You're ok?" I asked, still inside him, his hips still grinding. "My rules, I broke them, another first for me. Don't pull out yet". His body tensed and he held it, relaxed, then tensed again. Then a third time. And every time I felt his butt tighten and squeeze my shaft. He relaxed one final time and I pulled out, slowly. MJ pushed himself up on his knees (giving me a full view of the hole I just kind of fucked) and then turned over, pulling himself to an upright sitting position. He was hard and he'd made a mess, there was a puddle of cum where his cock had been pressing against the sheets, he had a third orgasm and he looked very pleased with himself. "First time?", I asked, moving up to him, still hard. He had his legs spread with his knees bent and ran a finger down to his hole. "Yes. First time wanking with a guy. First time cumming with another guy while wanking. First time tasting another guy's cum. First time having a guy lick cum off me. First blowjob with a guy. First time I blew a load in a guy's mouth. First time I let anyone near my butt hole. First time I let anyone in my butthole. First time I let a guy cum in my ass. First time I orgasmed while having a guy's cock in my ass. First time I let a guy fuck me while facing me". He saw the confusion on my face, so I asked "the last one doesn't make sense?". He slid down a little and parted his legs wider. "I don't know if I'll ever do this again and I'm comfortable with you. And you didn't actually get to fuck me. So, while you're still hard and I'm still up for some firsts, just fuck me." So I did. I shuffled forward on my knees, hooked his legs with my elbows and pulled him forward so his butt touched my stomach, then I lowered him and slid my cock up until I found his hole and slowly pushed it in. He was looking at me and it was pretty fucking intense, but I wasn't going to look away. We stared at each other while I fucked him like that, I started slow and deep, quickly picked up the pace and looked at his face until he dropped his head back and closed his eyes. He was wanking and we came together this time. I doubt I had any cum left, but I had three great waves of orgasm and with each one, I thrust in deep and held it. He came on the second deep thrust, just a little cum this time, but his body tensed and I knew he was having an orgasm. With my third thrust, he tensed too and I held my cock in there, just enjoying the sensation. He relaxed and tensed one last time, pulling me in even deeper and it felt like a party was going on down there.
I finally pulled out and smacked his pulsing hole with my cock head a few times. "Lots of firsts for me too, today. I don't think I'm ever going to beat this.". I lay back down and I was properly spent. "As experimenting goes, this was a good one, I'm glad we did this" he said, slapping my chest. "Another shower I think, then we've got to hit the road".
We left later than we intended to, but what a morning! I never saw him again, but I heard he had married a divorcee and they had a few kids from her previous marriage. I still think about that day and wonder if he does too.