**The first of many self-contained stories. Based on true events of exploring my own sexuality but embellished slightly.**
Chapter 1 -- The Roommate
I love sex.
And I'm pretty hot, so I get a lot of it.
Not to sound completely self-involved, but when I look in the mirror, I'm proud of what I see, and I'm totally satisfied with my sex life. It's weird because back in high school, I was not this way at all. I had zero self-confidence. I was probably about 40 pounds overweight and I couldn't imagine a scenario where I would ever lose my virginity.
That changed when I got to college. I hate sports, but I wanted to look good naked, so I started working out. I would run and lift weights. I was a complete amateur and really shy about it. I would casually spy on hot guys in the gym doing their routines and wonder if they knew more than I did, or if they were just as lost and just better at projecting confidence. I would see them working their arms, their chest, or their legs and copy their routine, thinking if they looked so good from doing those moves, maybe I could too. I worked hard and lost the extra pounds and even gained some good muscle definition. Of course, being a broke college student helped 'cause I was eating a lot less than when I was free-loading with my parents, and my college was in the middle of nowhere so there wasn't much else to do anyway.
It wasn't until I was twenty-one that I had enough confidence in myself to finally lose that fucking virginity. The dude's name was Tyler and he was pretty cute. At first glance he looked like a twink but he turned out to be more of an otter, totally my type. He was tall, six foot, and skinny but not bare bones. He had dark hair and eyes and super nerdy glasses and did I mention the fucking hair. Long soft fur from head to toe. He had beautiful stubble on his face and thick soft hair all over his chest leading to the perfect treasure trail and bush, and at the end of that treasure trail was a magnificent cock. Thick at the base, thicker in the middle and then a nice pointed tip with a fat mushroom head. It wasn't bigger than mine, but it was nice and big, just what I was looking for.
Too bad the sex was terrible.
I mean it wasn't terrible. We started slow, which I like, hands, then mouths, then we flip flopped, which was fun. I learned that I preferred to top but that I can tolerate bottoming which I was nervous for. He hurt more than a little the first time, but I got used to it and even came to enjoy parts of it. He usually came in about three seconds and I didn't. So he watched me jerk off for a little while and It wasn't until I got on my knees and grabbed his now-limp dick with my other hand that I finally came all over his chest.
He may have cum quick, but I beat him in every other regard. I cum a lot and I cum hard. It splashed all over his chest into that thick soft chest hair. I thought this was hot and so did he, but he didn't want to take too much time to enjoy it before he got dressed and we watched a movie.
Actually if I'm being honest, I think we watched cartoons. Sexy, right?
We dated for maybe three months, we were not soul mates, but I really liked his cock. Over this three-month time period he made me cum exactly zero times. It was a red flag. You hear guys talk unashamedly about cumming super-fast their first time, this was not my experience and I started to wonder why. Maybe it was because I waited longer than all my friends, or maybe it was because I jerked off so damn much. At LEAST twice a day since...well before I could cum. I was having dry orgasms for years before I had any clue what it meant. And maybe part of the trouble was I didn't stop while we were dating, I still jerked off a lot, so maybe it just hadn't had a chance to refill.
Maybe.
The second semester of my Sophomore year in college, Tyler and I had gone our separate ways, and my old roommate had dropped out. I had roomed with the same guy both years so far, we weren't best friends, all my best friends had moved into off-campus apartments that I couldn't afford. I worked, I just didn't have as much supplemental parental money as they did, plus university housing was cheaper. At twenty, I was still young and stupid enough that I didn't hate the dorms and even enjoyed things like the communal showers and the young and sexual energy of a bunch of college students under one roof.
I was also older than the fucking freshman and shit so I got to choose my room. So I chose a corner room on the 13th floor of the building. The tallest building in the little town in the middle of corn fields. But the energy of the room was about to change, the University sent me a notice that I was getting a new roommate of THEIR choosing.
What a nightmare, it was going to be like Freshman year all over again, trying not be disgusted with all their habits, or their probable stupidity.
It was January and my new roommate arrived on the coldest day of the year wearing a T-Shirt and athletic shorts.
We get it, you're straight.
"John" He introduced himself.
"Adam" I said, introducing myself.
He was a pretty typical twenty-one-year-old frat-type guy, except that he didn't join a frat. He said he was going to, but he was too lazy. That didn't stop him from doing frat-like things like drinking A LOT of beer and leaving the cans and bottle everywhere like they were trophies, or constantly going in for undeserved high fives, or just talking like he was the coolest guy in the world, when really, he had rarely ventured from his parent's basement somewhere in the suburban Midwest.
He was decent looking, a little doughy but not fat, maybe 5'9" with light brown hair and blue eyes. His complexion was a little strange, I remember always thinking that he looked sick, like there was a green tint to his skin or something. But still, in the few months that we lived together, he definitely got more girls to fuck him than I got guys to fuck me. Of course, it didn't occur to me that it was probably because we were in a small Midwestern town with almost-zero other gay guys around.
I was open with my sexuality and he was cool with it. For the most part, we left each other alone. He would play video games on his side of the room, and I would watch movies on mine. We both had plenty of other friends, so I would go out and hang at my friends off campus places and I assume he would go and hang out with his own friends. It was not as bad as I thought it would be.
"You know what I love about gaming online?" He asked one night. It was late, probably like two or three in the morning. I had finished a paper a little while ago and was now watching TV trying to make myself tired. "You can, like, have conversations with people from all over the world. Like I've been talking to this guy from Minnesota who's pretty cool, but you can talk to people from anywhere."
"Uh huh." I responded trying to ignore the fact that he was trying to make whatever online game he was playing sound like some interesting worldly activity.
"He was talking to me about all the threesomes he's had. It was fucking sick." He spouted. Taking off his giant noise-cancelling headphones. "He even said he had a guy guy girl threesome, would you ever do that?"
Was this guy asking me about sex? That was a topic the two of us hadn't breached before. "Uhhh..." I responded. "Would you?" I asked trying to avoid the question.
"I mean probably not, but maybe if we didn't touch. But yeah, I guess if there was a super hot girl who wanted to fuck with two guys at once. The thing is he said he's not gay though, but he and other dude still touched and shit. Would you do a threesome with a girl even though you're gay?"
