Let me start by inroducing myself, I'm Tom, 30 years old and now consider myself bi. The following stories are an autobiography of my sexual activities which I have kept to myself going on 10 years. I will attempt to be as truthful as my memory allows.
during my teenage years, I never considered myself bi. In fact, even today, I am not physically attracted to men. I simply love being fucked, and I love cock.
My first experience outside of straight sex occured when I was 19. I was and still am a very horny person and would frequently go online to try to chat up women and look at porn. During one of my late-night masturbation sessions, I started chatting with a gay male online. I was curious about what it was like to be gay and have anal sex, and I was open-minded enough to chat openly with this guy. Our chat quickly became sexual and when I inquired about anal sex, he replied: "why don't you try it?" I was confused, but he quickly educated me. He instructed me to get some lube and start rubbing my asshole. I followed his instructions and started rubbing the outside of my ass with my finger. I was surprised at how good this felt. I wrote him that it was difficult for me to type while one hand was jerking off my cock and the other rubbing my asshole. He said it was ok and that he would just talk me through it.
Next, he said, stick one finger slowly into your ass. I pushed a finger in about an inch feeling my tight sphincter squeezing my finger. Again this felt great, and as I wiggled my finger around, I felt my ass relax and contract around it.
Then he told me to stick it in all the way, careful not to scratch myself with my nail and to feel the lump on the front wall of my rectum. I did this and all of a sudden an electric sensation coursed through my groin and my cock immediately became fully erect. I had discovered my prostate! I proceeded to follow the instructions and rub my finger in and out of my ass and push against the prostate, until I came like never before.
My experimentation increased over the next few months. I often fingered my ass while masturbating, but this made it difficult to surf the web while both hands were occupied, so I started using various kitchen utensils to stimulate my ass while I jerked off. I eventually bought my fist dildo off the internet, and had discovered a new friend.
Eventually, my chatting online became frustrating and I was looking for something more. I chatted with a few guys and checked out gay porn and became more and more curious. After a while, I met one guy around my age who wanted to meet in person. I can't believe I did this now, but I drove 90 miles to meet him. I was dissapointed by his physique. He was chubby and not very good looking, but I had driven all this way and was determined to have my first man on man experience.
We drove around for a while and chatted. I was very curious about his gay experiences, and he told me about the guys he had dated and how his family was cool with it. I knew my family would never understand and knew I would never reveal this side of myself to them or any of my friends.
He took us back to his place which was empty as his mom was at work. We proceeded to make out (something I haven’t enjoyed doing with a man since) He proceeded to stroke my cock through my jeans and I did the same for him. It was my first time touched someone else’s dick and I loved it. It was so thrilling to feel the hardness and warmth even through clothes. He got down on his knees and slowly pulled my pants down, then my boxers. He reached up and took my t-shirt off and started touching me all over. I admit I was trembling from nervousness and not fully enjoying myself. He stood up and took off his clothes. There in front of me was the first time I saw an aroused man naked. I quickly reached a trembling hand to his cock and felt the warmth of his skin directly on the palm of my hand. I started gently stroking him and saw some precum ooze out of the hole. He withdrew and got back on his knees and in one gulp took my cock into his mouth. Now at this point, I was not extremely sexually experienced, but I had been with a few girls and had received blowjobs before. Nothing like this! He swallowed my whole 6.5 inches and had such pressure that I was about to cum within a minute. But I hadn’t driven 90 miles to get a blowjob. I wanted to feel his cock, to experience what it was like to do the same things to him that he was doing to me. I pushed him away and bent forward towards his cock. I admired it from close and took in the scent of a man for the first time. His was not a gorgeous cock, but it would do for my first time. Besides I was so turned on by now that I would do anything. I started by licking the shaft, then the head, then before I knew it, I was sucking my first cock. I discovered something about myself right then and there: I was born to suck cock. I took him deep into my throat and loved the idea of giving him pleasure. Eventually, we moved into a 69 position and sucked each other’s dicks with pure heat. I wanted so bad to feel him cum and soon my wish was granted. He suddenly stiffened and his cock began to spurt hot thick semen into my mouth. I had wanted to watch him cum so I pulled his dick out and aimed it at my face feeling and watching it spurt all over my face. That was when I started to cum and he sucked my cock deep into his throat and swallowed every drop.
I quickly showered and drove home. I was feeling very conflicted about things and still do to this day whenever I am with a man. I never contacted him again despite his several emails to me. I had promised myself that it was just something I wanted to experiment with and that I wouldn’t do it again. Time would prove how wrong I was.