Sorry it has been so long since the last installment. Thank you to all of you who wrote to see how I was and if more stories were coming. I hope to hear from anyone who likes this newest one. I had a busy year with some ups and downs, and got out of the habit of writing. Hopefully more to come, I got plenty of stories to tell. Enjoy.
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.
The Townie
All through grad school on and off I fucked a young townie. He was hot as anything, but dumb as a rock. I often wondered if he even knew how to use his phone. I met him the same way I met most of the dudes whose cherries I busted during school, on the internet. I had posted one of my 'Looking to Try it out with a guy?' craigslist posts and he replied. Said he had looked at guys in the locker room for years and really thought he wanted to try some stuff. We talked on email and text for a few days, and then one day he texted me and told me to come over immediately! I was kind of curious why he wanted to meet up so suddenly, but later learned his schedule was a bit difficult.
I hopped in the car and headed to his address. I later learned from reading the paper and from my job that it was the nastiest apartment complex in town, and it sure seemed like it. Once I knew the address, I saw it all the time in the paper and elsewhere, usually for a murder or a meth lab or domestic violence. Not a nice place. I found his door and knocked. His name was Mark, and his pics had been either blurry or too far away to make out, but when he opened the door, I was stunned, and my cock twitched in my shorts. His email address had something to do with basketball, but I then realized he must have played at least in high school if not at a higher level. Mark was pretty darn tall, well over 6 feet, and had those aw shucks all American looks with overgrown blond hair. I tried to make some small talk, but he said he had been dreaming about sucking dick, and almost pushed me onto the sofa as he pulled my shorts down. He had big pillowy lips on his cute dumb face, and they were soon wrapped around my hard cock. I instantly believed he had never done anything with another dude. He had no technique at all, but like most first timers, made up for it with eagerness.
He was just wearing some basketball shorts, showing off a nice upper body with good abs etc. He was feasting on my cock, sucking it with such force it was like having a vacuum nozzle attached to it. He was on the floor between my legs, and being so tall, there was no way I could reach his ass or cock to play with. In any case, I knew it wasn't going to be long. He was sucking it so hard and so fast, I could feel the cum rising almost immediately, and it was a challenge to hold out for ten or 15 minutes or however long I did. He was gently squeezing my balls as he sucked my dick, and dropped down a few times to give them a nice few licks, and even down to my taint once. When I couldn't hold out any longer, I grabbed his ears and really started fucking his mouth, and he kept up the pace as well. I didn't figure I needed to warn him, and finally moaned and let out a huge load spread over about ten shots into his still-sucking mouth. He kept going for it even after I blew my load, and I had to ease him off my dick since I get pretty sensitive after cumming sometimes. Mark got up on the sofa next to me as I leaned back to enjoy my post-orgasm. He pulled his tank top back on and sat back next to me.
I reached down to his shiny nylon shorts and felt around for his cock. I am not that selfish, I'll still jerk a dude off after a great BJ like that! What I found in his shorts reached over past his hip. I traced it back to where his penis should begin, and sure enough, it was like a baseball bat in there. I don't remember what I said, but I started jerking that huge penis through the school-colors fabric. I was just trying to fish the monster out of his shorts when a baby started crying. That really caught me by surprise. Mark got up and went into a back room, probably to see to the kid. The crying stopped and he came back. I said I probably should go, but he said to hang out, his girlfriend would be gone at least another hour. I of course came to find out that the kid was his, he had knocked his girlfriend up when they were both 16 or so, and now he was 19, done with school, and had a shitty job in a warehouse, a girlfriend he hated, and their kid to take care of. It kinda weirded me out that there was a baby in the house, but Mark was hot, and sexy as hell. Plus, when a dude is that enthusiastic as a virgin to guys, good lord!
Mark leaned over and started sucking my dick again. I was still half boned and immediately got hard again as he worked my meat. Like before, he was sucking like he was trying to get a really thick milkshake through a too-small straw. Since he was beside me, I started playing with his dick again, and finally managed to get the monster out of his shorts, no small feat since I basically had to take his shorts off to get it out. Apart from one totally straight buddy, it probably was the largest penis I had ever seen in person, and would have been an internet phenomenon. Probably it was bigger than my friend's, since although he loved to show his cock off, he'd only ever let you get a quick glimpse of it, hard or soft. Mark's cock was no shit at least 10 or 11 inches. It had a big angry looking red head the size of a small apple half covered by a foreskin. It was impossibly big. No wonder he'd knocked his girlfriend up, he was shooting his jizz straight into her uterus.
Mark was bobbing up and down on my dick, even quicker and more enthusiastically than before. I was surprisingly starting to feel the tingle, this dude was about to make me squirt again so soon! After a few minutes he stopped and said "Fuck me. I really want it. I've been so horny thinking about it." That kind of caught me by surprise. We had talked about that a little in our emails and texts, but it was always something in the future, something to work up to.
"Are you sure dude?" I asked. "We don't have to rush things, we are going to meet up again."
"Yeah, I really want it bad."
"But you've never gotten fucked before, right? Are you sure?"
"No but I've been thinking about it so bad."
"I don't have a rubber," I said, thinking that would cool him down.
"I don't care. I don't want one anyway."
That kind of set me back. At this point, at the beginning of school, I had never fucked a dude without a condom. Well except for my buddy in high school, but that was the only dude I had fucked until the end of undergrad. I had fucked plenty if not most of the girls of my career without rubbers, but that's not the same as anal sex with a guy I just met. But then I realized he had probably never worn a rubber in his life, given what was sleeping in the back room. I believed he had never done anything with a guy, he had said so, and it sure seemed that way. He had probably only ever had sex with the girl he got pregnant, and probably not much with her either.
I leaned over and stroked his dick a few times. It seemed to have gotten bigger, and was leaking like crazy. My hand was covered in pre, and I started slopping it down below his giant balls onto his hole. As he felt his puss get slippery, and my finger running around it and into it, he was shaking and moaning. I let a few big gobs of spit onto my hand as he brought his huge feet up onto the sofa, giving me better access to his hole. He had a few pubes, and some fine blond hairs on his calves, but the rest was smooth and white, with a tiny darkly-colored butthole that seemed too small for the rest of his long frame. I used some more spit and got a finger nice and deep in him, making his cock burp out even more precum, or maybe a little orgasm. I stood up and grabbed his ankles, lifting them up and apart, hiking up his butt and opening his cheeks. That huge dick was just bouncing around on his abs leaving a trail wherever it went.
I began to rub my cock around his hole, and occasionally apply a little pressure. Like any virgin, he automatically tensed up feeling the pushing on his entrance, but after a short time, I could feel his muscles relax, and his hole started opening. Once my head popped in, he let out a low growl and said pretty authoritatively to 'fuck me'. So I just kept pushing and apart from the initial entrance, there was no more resistance, just a burning hot tight tunnel squeezing my dick as it pushed in all the way, aided by a little spit. When I quickly reached bottom, I stopped and let him get used to it for a second, but he thrust back on my cock and said 'c'mon, fuck me'. I began some long in and outs, sometimes taking it all the way out, rubbing it around his hole, and pushing all the way in as hard as I could. He didn't seem to like me taking it out, and made a little frown when I did, so I gave that up and set my mind to some hard pumping.
I honestly don't remember all the details of that first fuck, it was some time ago. I remember it was pretty damn hot in that apartment, and I was dripping sweat onto his chest and face as I nailed his tight twat. It always worries me with really tall guys that my dick is relatively shorter, that all the important parts are further up there since they're so tall, but I don't know if that's the case, cause most of them seem to enjoy my pretty average cock quite a bit. It makes sense though, if a dude is 6'6, wouldn't his prostate be like twice as far up? Who knows. Anyway, Mark seemed to be enjoying himself. He was sweating a lot too, and thrashing around on the sofa. I pushed his legs far back and pushed myself down on his chest to give him a kiss, but he turned away. Oh well, not every guy likes kissing, especially not the first time. I was getting pretty close. Hitting a girl's pussy without a condom isn't like hitting a tight guyhole. Hell, some pussies are so loose it's tough to even cum with a condom on. But, I could feel it coming. I slowed down a bit to regain some composure but that earned me a disappointed sigh and some more thrusting on Mark's part.
I soon realized why he didn't want me to slow down...he was right on the edge. He hadn't touched his cock at all, but reached down and sort of pinched the head, the immediately shot a huge load on his eye, chin, and chest. I was trying to get a free hand off one of his ankles to do my favorite thing-feed him his own goo, but he beat me to it and started scooping up his own load and sucking it off his fingers. His orgasm strangled my cock, and as I pounded into him as fast and hard as I could, I felt it coming. He must have had some good core strength and strong ass muscles, because as he squirted, it felt like his ass was forcing my dick out, no matter how hard I pushed in. I was kind of on autopilot, and if I had thought about it, I would have pulled out and shot on his face or chest, but it was too late, and I flooded his chute with what felt like a giant load again. I immediately apologized, but was cut off by Mark saying it felt so good.
I kind of flopped onto the sofa next to him, and lightly stroked his cummy cock, but he sort of pushed my hand away. Either he was feeling bashful or awkward, or got sensitive after squirting like I do sometimes. I let my hand fall down to his balls, and rubbed those big egg-sized things for a moment before reaching down to his hole. I put a finger on it and it sort of slipped right in. It closed around my finger, and I could feel his heart beat through my finger. I could also feel an awful lot of sperm! Mark suddenly got up, and I gave him a little spank, but he kept moving over to where he picked up a towel out of a pile of clothes and toys, and headed toward the bathroom, which was just feet from the sofa. "I gotta get cleaned up," he said, giving me my cue to leave, "that was awesome, see you later." I left back out into the hot steamy afternoon. I was a little deflated since it had been such awesome sex to have such an abrupt end, but it was his first time, he wasn't the brightest bulb on the tree, and he may have had mixed feelings. Anyway, I went home and texted him that it was awesome, and that we should hang out again soon.
That proved tougher than anticipated. Mark worked two shitty jobs, didn't have a car, and had a gf and baby. His girlfriend/baby momma apparently had some job, but just for a few hours a week when he was of course expected to look after the kid. Not ideal. But, we did manage to meet up again pretty soon. He texted me one day and said to come over. Luckily I was in the car and actually on that side of town, so I said I'd be there in five. When I got there, it turned out the girlfriend had just gone to the supermarket, so she would be back soon. I got this information as he was closing the door; my shorts were at my ankles one second later and my cock was in his mouth with his big lips pressed against my pubes. I couldn't argue with that, but eventually got weak-kneed and had to move to the sofa. He was sucking with the force of a shop vac and moving up and down my pole so fast it was like a machine. I hadn't even jerked off in several days, so I knew this wouldn't be a long visit. Sure enough, after probably only ten minutes, I was pumping a big load down his throat as he kept sucking like there was more to come. I tried to persuade him to at least let me jerk him off, he was hard as a nail, but he declined. I left quickly, praying not to meet his girlfriend at the door.
We started to talk more, but even that was tough. He was terrible at emails, when he replied, which was unusual, they didn't make too much sense. Texting was better, but he had one of those shitty 7-11 phones that only worked half the time, and only then if he had money to put credit on. We talked on the phone sometimes, he could call during breaks or lunch. His work schedule always changed and was hard to keep up with, and he often didn't know his schedule till the day before, so making a plan was impossible. However, maybe a month later he texted and said he was home alone for a few hours. The baby momma had taken the kid somewhere. I headed over there as soon as I could.
When I got there he was in the same old university-colors bball shorts and a T. He looked happy, maybe cause baby momma was gone for a while, and he looked good, hotter than I remembered for some reason. Maybe his mischievous grin was because of what happened next. He went for my cock, and I stroked his, which was already about to rip his shorts. I eased his shorts down and immediately saw he was wearing a tiny pair of pink thong panties, with his cock sticking out the side and across his thigh! I had of course seen that sort of thing on the internet, but had never seen a dude in person in sexy panties. Much less a six and a half foot tall toned basketball jock. It made me incredibly horny and my dick got even harder if possible. Mark was beaming, and asked me if I liked them. "Hell yeah! SO hot" I told him, truthfully. I was rubbing his firm ass and feeling up the thong strap. I loved the look of his comically-big penis sticking out of those little panties and leaking all over his leg. This dude may be kinkier than I thought! I didn't think that a small town working class kid like him would have those type of kinky ideas, but I was happy to play along.
Mark started to kneel, but I stopped him when his head was close to mine and gave him a kiss. Maybe because he was in girls' frilly fuck-me panties he responded, and we actually had a pretty tender kiss before he continued to his knees and got my cock in his mouth. After a few minutes, he pulled off my cock and whispered "are you gonna fuck me in my panties?"
"Hell yeah!" I said, "whatever baby wants." I didn't know it at that time, but for the rest of the time I knew Mark, he always wanted me to call him babe or baby.
I guess he really did want it, because he hopped up right then and knelt on the couch, pushing his ass back as far and high as he could, while sort of burying his face in the back of the cushions. I was amazed he could get into that position being so tall, but he was a little diagonal, and it was a big couch. His ass was spread wide, and he reached back and spread it wider. I could see his hole under the thong strap, and swear it was already pulsing and winking at me. I actually had a condom and lube in my pocket this time, but decided what the hell, I've already tapped this puss without one. I was going to use lube, but decided to try spit first. Nowadays I would have rimmed the hell out of the hot panty-covered ass in front of me, but back at that point, I wasn't too into giving rim jobs, and certainly only right after a long shower with a lot of soapy fingers up that puss. I lifted the thong strap and let it snap Mark's hole a few times, making him moan. I circled his hole with my finger, and let several big loogeys drop right onto his pussy opening, working them in with a finger, and then probing around his chute with my cock.
Mark was wiggling his ass around and trying to push back, although it was tough in his position. I got the message, and this time, without warning, moved the strap aside, lined it up, and pushed until I was all the way in. I grabbed his hips and really started pounding it out, making Mark moan down into the sofa cushions. It was making me hot watching my dick go in and out, rubbing along the thong, which was now soaked in spit and ass juice. I really don't recall anything too specific about that. I was going to flip him over for the big finish, but after pounding that ass hard for a while, I had to cum all of a sudden, and grabbed his hips hard, gave a few final thrusts as strong as I could muster, and dumped about 10 volleys deep in his puss. Mark got some toilet paper to clean up the wads of cum he'd left all over the sofa cushion.
After we caught our breath Mark actually started talking. Maybe the comfort in knowing baby momma was gone for several more hours made him want to hang out. I teased him a bit about the panties, and he blushed but said he'd been wearing them for weeks and he loved them. I never figured out where he got the panties, or how he hid it from the lady, but it was hot to me. My best guess is that he took her dirty ones, wore them, and then put them back in the laundry. The next several times we met up, he was always wearing some frilly sexy panties, and always wanted to get fucked in them. The craziest part of the panties was what he told me a couple months later when we were talking on the phone one time. He said guys at work had noticed his panties when his shorts or jeans were riding low. One guy at the warehouse had said something, but Mark didn't seem to mind the guys at work knowing. I would have thought a young guy like him with a kid in a fairly small town would be worried, but he didn't seem so. Maybe my stereotypes of young guys who work in warehouses is too homophobic. But the thing that I didn't believe at first but that made me rock hard was when Mark told me that one day, a co-worker had come up next to him at the urinal and reached down the back of his shorts and rubbed his panty covered ass, then placed Mark's hand on his erection. Apparently a few days later the same guy came up to him in the bathroom again, and this time got his hand inside the panties and actually fingered Mark's ass for a while!
The next time we met up I asked Mark more about this. Was this dude who fingered him fucking him too? He assured me not, just said a couple of the guys liked to feel him up in his panties and tease him like a little slut. I was wondering what kind of warehouse this was, but I believed him it was just relatively good natured fun. As time went by we would meet up sometimes more or less, but it was always hot and always fun. It was tough because he never got a car, moved in with his mom for a while, then back to that nasty apartment. It was tough to ever make a plan with him, although I always wanted him to come to my place where we could have some real privacy!
The last time I saw Mark was a good one. Like usual, I fucked him almost as soon as I got there, over the arm of the sofa. For some reason, he didn't have panties on that time, and I gave him a hard, but not super fast fuck with him bent over the arm, his long slim legs spread wide. With his monster cock hard and in easy reach, I slowly squeezed and stroked it as I fucked him. He was making as much pre as always, and his cock felt like it was lubed. I could feel his dick swell, and I reached to catch his load, with a half dozen hard spurts cupping in my hand. I let most of it drop down his ass crack where it slid down to where my cock was sliding in and out of his hole, pulling a little bit of his ass lining out each time I pulled out. I came all the way out as his sperm reached his hole, and pushed the glob in with my dick, lubing him up with his own juice. I pulled him by his shaggy hair so his head was off the side of the pillow and stuck my hand in his mouth and he dutifully licked my hand clean. I remember that orgasm as being one of those ones so hard it gives me a headache, and my head was kind of spinning as I pulled my slimy dick out of him.
I suggested a shower, which I think we had done once before and he liked. As we got in the tiny bathroom, I told him to bend over. I wanted to look at his ass, I always like doing that and he was usually too rushed after we fucked for me to play with it. He bent over, with his hands in the tub. His ass was shiny and red and hanging a little open with both of our sperm dribbling out. I pushed two and then three fingers into his loosened chute and pulled out a blob of juices. I was going to wipe it on his back, but then leant down and pushed my hand into his mouth again, which he eagerly began sucking and licking for quite a while, as I dug up his pussy with my other hand. By this time, I was painfully hard again, and pushed his ass down so his knees were bent and his ass was level with my still slippery dick. I pushed it in hard, making him lose his balance a little bit. Fucking a guy that tall over a tub in a little bathroom was tricky, but I nailed him hard and fast till he was sort of crushed down in the tub with his ass bent over the edge of the tub. It was a tough angle for me, but a fast and furious fuck. I heard him making his usual cumming noises after a while, and felt the vise-like grip of his butt tube massaging my pecker. For a second fuck in a row, it was quick for me, but I shot a good number of jets up his ricker and helped him up out of the tub.
If I remember right, that was just before exams, and then Christmas break. By the time I got back to town, his phone was cut off (Mark had had about five or six different numbers since I'd met him). He finally emailed me, and we talked on and off about meeting, but it never happened as I got busier and busier towards the end of school, finishing thesis and exams and etc. I am sure I'll never see him again, but it was hot for me to meet someone I wouldn't usually meet, and show him a new world. I know some would call him rough trade or whatever it is to fuck a social and economic inferior, but he was really a sweet guy who had his moments, and seemed to be doing well given a tough situation.