I wrote up this story for PMs with some people I’ve been chatting with and got good feedback, so I thought I’d share it here :)
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So my first girlfriend broke up with me in my third year of college, about eleven years ago now when I was 21. I’d known for years that I was bisexual but never acted on it in any way so after that I decided it would be a good time to start experimenting & I started looking online. This was still the relatively early days of internet dating so I had a few false starts there (some weirdos out there), but eventually I got talking to this guy a year or two younger than me who seemed cool so we agreed to meet up. He was gay but not out, I told him I thought I was bisexual but hadn’t been with a guy before. I was a little old-fashioned about it I guess because we went to see a movie first. He was a cute, 5’6″ asian guy with a nice smile and a great body (he did some modeling a little later actually, which I’m pretty proud of!) I knew right away I was attracted to him but the whole experience was still so new to me I didn’t really have any clue how to make a move. It was kind of a thrill walking around town with him though, looking to everyone else like just a couple of college guys hanging out, when really we wanted to fuck each other. Anyway we were chatting about movies and I asked if he wanted to come back to my room to watch a DVD. A little clumsy but he said sure so we went back to my place. At that time I had a college apartment with a couple of other (straight) guys, neither of whom I was particularly close with, so I was a little worried about what they were going to think, but neither of them were there when we came in thankfully. The door to my room was pretty solid & had a lock on it so I felt a little more comfortable once we got inside. I put the movie in & we watched about 10 minutes of it before I couldn’t wait any longer to make my move. I was still so nervous because I’d never done this before, I still considered myself just ‘curious’ so I had no idea how I was going to feel if I went for it. What if I saw him naked and suddenly found I wasn’t interested at all? Finally I just put my hand on his thigh and started gently caressing. It felt like I was being so awkward but as soon as he turned and looked at me I could see he was into it so I reached forward and kissed him. I’d kissed a guy before as a high school dare so it wasn’t a completely unfamiliar experience but never anything like this: instantly we went into full on passionate making out like we’d been lovers for years. With a thrill I realized it was really happening and I was about to have sex with a man, and I felt myself get hard in seconds. He started touching my chest over my shirt and I knew I wanted to see his body so I reached over and pulled off his shirt. He was in great shape so I spent a wonderful few minutes running my hands over his body. It was incredible experiencing the difference between a woman’s body and a man’s this way for the first time, feeling his strong firm pecs and hard abs where before I was only used to feeling softness, with him still kissing me gently the whole time. We hadn’t discussed who would be the top or anything like that beforehand, but I got the feeling he wanted me to lead so I pushed him down onto the bed and leaned over him to begin kissing his stomach, licking his nipples, feeling the muscles of his shoulders, and just exploring his whole body. Finally I reached down and felt his hardness through his jeans. Before I even met him I had had the burning desire, if I was going to have any experience with a man, to feel a cock in my mouth. So I couldn’t wait any longer and unzipped his pants, he pulled them off for me and there was his pretty little hard dick. He was only probably 4 inches or so but I didn’t mind, for my first time; I would have been a little intimidated to start out with a monster cock! I moved down and took him into my mouth. I didn’t know what to expect – would dick taste weird? – but he just tasted like good clean firm skin. I ran my tongue up and down his shaft and began gently sucking him. He stretched out on the bed, totally relaxed and I kept working his cock, listening to his quiet moans. Feeling him run his hands through my hair and gently push my head up and down was intensely hot. I felt like I was just starting to get into it when suddenly I felt my mouth filling – at first I thought I was just feeling my own saliva before I realized he was cumming in my mouth. I stayed on and took his whole cock in my mouth and sucked down his whole warm salty load while he stretched out and shuddered. After that I slowly licked his dick up and down for a few minutes until he was soft again. I sat back, not sure what the etiquette was here – I had a hard rod about to bust out of my pants and I desperately wanted to fuck him, but did I have to wait a little until he was ready? Fortunately for me he didn’t want to wait at all, he moved over and took my pants off and started returning the favor. My dick is a lot bigger than his was (about 7″ and pretty thick) but he didn’t hesitate; I lay back and he started jerking me and teasing the head with the tip of his tongue. I had actually never had a blowjob before (first girlfriend didn’t do that, boo!) so this was a new experience for me and although it was hot and he kept me rock hard, it kind of tickled and I didn’t think I was going to be able to cum from it. So instead I looked him in the eye and said “I want to fuck you.” He looked back and said “Ok” and turned over to lay face down, ass up. He had an absolute peach of an ass, great firm ass cheeks and nice strong thighs. I put a condom on my cock and lubed it up, put some lube on my fingers and started probing his asshole. His ass took my fingers with no trouble at all so I just moved over and went for it. I was so excited I thought my heart was going to stop as stood over his legs and lowered myself to guide the tip of my cock to his asshole, and I slowly eased it in. He took the tip with a little moan and I pushed my whole length into him, letting out my own low groans as I began slowly sliding my cock in and out of his ass. Nothing had ever felt so good or so tight. I wasn’t sure how hard and fast to go at first, I didn’t want to hurt him but between moans I heard him say “fuck me”, “fuck me harder” and I began thrusting into him again and again. In a minute sweat was dripping down my chest and I was in ecstasy slamming my cock into his tight asshole, slapping my thighs against his cheeks. I remember even in the midst of all that, realizing “It’s official. You’re a fag now”. In another minute I could feel myself ready to burst and I pushed myself all the way in, balls deep in his ass, and blew a huge load with one of the longest, most intense orgasms of my life. Afterwards, that was that and it was getting late so he headed home. I walked out onto the street outside the apartment, and I couldn’t see anyone around so I got a thrill from giving him a quick kiss and a squeeze on the ass as he walked away. We tried a couple other times to make plans to meet up again but it never came off, but I still think about that night all the time.