See my intro post in r/sexstories. This sub has more people so I’m jumping over here. This first one isn’t great, but important if you want to read my future posts with the good stuff. Also this post is mostly gay. More straight stuff in the future.
I was in 10th grade. I had no game basically with women (or at least women that were ready to have sex). I had had a girlfriend a year before that we had given oral to each other, but not very often and it wasn’t that great (ow, her teeth). But I was ready to try a guy.
Years earlier I had found my dads respectable magazine collection. It had almost the entire 80s and the first few years of the 90s of playboys. He also had a good smattering of Hustler, Penthouse, Maxim, and several others. It was great. My parents weren’t home a lot so I got to explore them fairly early.
At one point there was one magazine, I think penthouse, where there was a guy in a shoot with a girl. I was very interested by his cock. It was probably 8″ and thick. Also around this time I found my mothers dildo. I experimented with it in my ass. It hurt mostly. But I enjoyed the intensification of my orgasms. That wasn’t very often though, it was too much trouble and cleanup to mess with. Besides… I’m not gay. I dont like guys.
So some years go by and I was in high school.
I knew one gay dude. We had gone to school together for years. He was a year older and very fem and definitely gay. One night I messaged him on AIM. It started harmless enough, I asked him to buy me cigarettes and we planned to meet up the next morning before school. Yeah, I did want some cigarettes, but i also was interested in some dick. As we talked I opened up. I confirmed that he was gay and revealed I was curious. He was very interested. We made additional plans for him to come over after school the next day.
The next day we met and smoked cigarettes at the subway by the school. I was so nervous. He was almost too gay for me lol. He wore a very strong gay cologne, or perhaps his car just smelled of it. The tension built and he agreed to follow me home later on. My parents weren’t home for about 2 hours after I got home in the afternoon so it was perfect.
I was so horny all day, precumming in my jeans and hiding my raging hardons. Finally it was over and we were off. I wasn’t out yet, so we had an eye contact and discreetly left at the same time and he followed me.
On the way home my dad called. My grandmother was on her way with food that HAD to go in the freezer or it would be ruined. Dammit. We got to my house and I informed him of the situation. He kept starting to make out with me in my bedroom while we waited and touching my crotch.
I was so hard but nervous because my grandma was coming. I couldn’t be hard when I answered the door and didn’t want to redress either. He kept trying to get in my pants but I stopped him. I felt the stubble of his lips on mine. Yep, I was definitely kissing a guy. I wasn’t super into it I guess. I mean, I wasn’t really tryna have a full gay experience. I dont know what I wanted but making out hadn’t crossed my mind. For a fem, he was very dom. He was hungry for me. He wanted my cock so bad. I wanted his too but it wasn’t time yet.
Anyways, she finally came and went. I went back to my room and it was time. With more kissing and rubbing, our pants were soon off. He had a really nice cock. It was about as big as my 8″ dick, but curved upwards instead of being straight out. Thats hotter now than it was then. At the time it was kind of weird. If I was in that situation now, I would have wanted to 69 because the upcurve deep throats easier.
Anyways, he began sucking my cock and it was great. Then it was my turn. Hell I didn’t know what I was doing but I tried. I think I enjoyed it. Except it had a taste. The taste of dick. I was pretty sure that was the taste of dick. Yep. That definitely tastes like a dick. I didn’t really like it. Soon he was sucking me again. I probably wasn’t very good at it.
He then said “you’ll get off faster if you fuck me.” Okay. Yeah. Let’s do it I guess. ( I later found out he was mostly a bottom) He laid on my bed and pulled his knees up exposing his hair ass. and I fucked him. It wasn’t long before he exploded all over his TMNT shirt. I kept slipping out and it was awkward. He kept pulling me down and kissing me. Ah… yeah im kissing a guy…. thats pretty gay… uh.
Anyways, after a few minutes he announced he was going to cum and shot thick ropes all over his shirt.
That was pretty much it. It was awkward, I was nervous, didn’t cum, and then he pretty much left. I was left at home alone. Still horny but feeling gross. I hopped in the shower and scrubbed the gay off me. There wasn’t poop on my dick or anything but my dick had been in an ass where poop is found. Gross. Of course I finished myself then.
It was interesting. Not great. Very gay. I wish he hadn’t been so forceful. I wish it had gone slower. Maybe we could have tried making out first for longer. Hmm, no I was too aware he was a man. Maybe if we had just done oral? Who knows, but it was too much too fast and idk. Plus it was unfinished so I just… wasn’t sure about it. Oh and not to mention the fact I had just lost my virginity *to a guy*. Fuck. Did that mean I’m gay? No, I wasn’t attracted to men. Like at all. I was just horny basically.
That would be a thought process that would happen many times as time went on. Not gay, so why be sexual with guys? Because they’re so easy? Like when you can’t find any weed in September before the harvest so you end up buying alcohol even though you don’t like to drink? Pretty much.
Anyways I wasn’t sure. I didn’t know what I was. I had just had gay sex but that didn’t mean I was gay. Id have to experiment more…. unfortunately many times with men were not fun for me, yet I continued. Maybe it was just that particular guy. Maybe a different guy would be different. Who knows?
Later that night we texted and i expressed interest in trying again sometime. He was wanting to be my boyfriend. I was nowhere ready to come out of the closet yet and declined. Sometimes I wish I had agreed to be secret fuck buddies for awhile.
However, we met up again on several other occasions. Im not sure when the next time was. But a few times stand out.
One was important. It was his birthday and he wanted to hang out with another chick we were in band with. She was a tall skinny big tiddy goth girl. We went somewhere and parked to smoke some weed. Somehow it got to “this dude wants either a blow job or sex because its his birthday.” However there was also kind of the question asked “which of us would you rather fuck?” I think it was more trying to see about my sexuality….
Of course I wanted to fuck her! I was still a Virginia with women. And I was actually into girls. And she was pretty hot, although I’d probably never date her or anything because she was kinda goth and I was kinda preppy/nerdy. So she climbs back there with me and sits in my cock. It was great, but only lasted a minute or so. She was too tall for us to fuck in the backseat in that position. Besides, birthday boy was sitting back there with us with a sour look on his face and his dick in his hand. iirc I sucked his cock for maybe a minute to soothe his ego. So no one came, I was taken back home and we all left horny. They didn’t fuck im sure because he was totally gay and they were friends.
Another time I came home from a church trip that took several hours. Somehow we ended up texting on the way home. This was my first case of blue balls. I was so horny. He wanted me to come spend the night and he would pick me up. I said I would ask my parents but didn’t. I was too scared to because they would ask too many questions about who this random person was. Again, I have often wondered what would have happened if I had? Maybe with all that time to explore and somewhere away from home it would be good? Alas, we did not.
On one occasion I went and picked him up. We found a spot to park and we were taking turns giving head while the other took a hit of weed. Eventually we moved further. This time he was going to fuck me. This would be confusing later when I wanted that but he was too much of a bottom.
We got in the backseat and he slid his cock into my ass and moaned. It hurt. But kind of felt good. Or something. My tight ass made him cum after only a few pumps and he blew his load deep inside me. I asked how I got it out of me and he told me I had to wait until I shit it out. I was mortified and grossed out. I haven’t been interested in anal very much since then. The idea of some dudes cum inside me…. no thanks. Then he insisted he had to get home suddenly and wouldn’t finish me. Two strikes for this dude, right? (This will become important in a future post).
I took him home and dropped him off, totally grossed out. Of course I eventually shit it out, but not quick enough. And also of course I would have more anal in the future with other guys. Again, maybe it’ll be different, right?
Then there was another memorable time. This was pretty much it. He nd his roommate picked me up and we went to a really good spot. Some of the details are blurry but ill do my best. The three of us did some dick sucking. His roommate also had a cock comparable to ours, but more straight like mine. Long story short we ran a train on him in the back of his roommates car. We took turns fucking his ass or mouth for perhaps 20 or 30 minutes. Eventually his roommate came in his ass. Right after that I also came in his ass. I made sure to blow it deep (payback, bitch!)
He was exhausted and flopped over on his back and said he wouldn’t be able to walk the next day. Afterwards they took me home.
There were several other minor interactions with him but nothing too crazy. I tried to seduce his roommate once but it didn’t go anywhere. His big dick was too big for my tight little ass and we couldn’t do it, and I have never wanted to suck a cock after it was in my ass, so we didn’t finish. We just quickly jerked off basically. This experience is also important to remember in my future posts. I wanted to experiment fully, right? Unfortunately I’m a total pussy and can’t take a dick in the ass. Too painful. Plus I dont want cum in there. Plus then its a shitty dick that I dont want to suck.
Anyways those dudes were so gay it was off-putting. I mean I’m not super masculine but you would never think I was gay or whatever. I was going to have to look elsewhere…. And elsewhere I looked.
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Afterword: just so you know, not all of my stories are like this. It was an awkward first time/partner, perhaps awkward like yours. In the future the stories will be much hotter and I’d like to think you could even fap to them. Also as stated in my intro post, there will also be stories where I’m with women. Those are all mostly hot. Stay tuned folks…
Source: reddit.com/r/eroticliterature/comments/us5vky/my_experiences_part_i_first_time