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Written by: boiboi7473 Category: True Story Tag(s): Boy / Boy, First Time, Gay, Young So! The point of this story is one thing and one thing only. To chronicle my sexual adventures as a promiscuous student in NYC (which are TRUE and still going on!)! I'll have to catch up on the first few stories, but once I'm done with that, hopefully each encounter will be recorded in detail ;) I hope all of you readers enjoy! I'll warn you guys in advance. This post is nothing more than an insufficient account of the events that led me to having sex with guys. Don't worry, the sex should come in by the next post! If anyone has any questions, or wants to know the nitty gritty dirty details, let me know! When I was a freshman in high school, I was definitely straight. The thought of even TOUCHING another guy pretty much made me want to throw up! I had told myself repeatedly that I would only date girls, simply because virtually no one my high school in southern Delaware is gay. Sometime in March when I was 14, I was jerking off to some straight porn, until I accidentally stumbled upon a picture of two guys going at it. I guess some sort of switch was flipped in my mind. I was so attracted to it for some reason. I kept thinking "Holy shit. This is just wrong," as I unconsciously searched for more. Needless to say, the habit grew on me, and eventually I would watch nothing but gay porn. Personally, I just found two guys having sex to be more aesthetic than a guy with a girl. The chiseled to slim features, the ability to switch roles, two loads instead of one, various types of men (I absolutely adore twinks!) everything about gay sex seemed so hot! But I still told myself I was nothing less than straight. I started to visit gay teen chat rooms when I was 15, hoping I would find someone else to talk to. Little did I know, I would just be dealing with idiots who wanted nothing more than kiddie porn and roleplaying over the phone or IM. My sexuality did straighten out for a while once I got a girlfriend. I stopped the porn, the sexual thoughts about men, and the stupid conversations with those ridiculous gay teens because I fell in love for a good while. Unfortunately, our relationship didn't last very long, and I ended up leaving Delaware to go to New York City for college. After not having done anything sexual for a while, my attraction to men increased. I had this burning desire to try having sex with a guy at least once. And so, I ended up discovering Craigslist and Adam4Adam. For a boy who was surrounded by nothing but straight men, I was pretty satisfied that there were at least a couple of services to allow men to meet men for sex. I was pretty scared when I actually posted my first Craigslist Ad. Being a complete virgin (besides a couple of blowjobs), I had ridiculously high standards. He had to look cute, he had to be white, and he had to have a place to stay. I eventually managed to find someone who fit my criteria to lose my virginity to, and boy was I surprised at who I found... For the sake of his privacy, I'll just refer to this guy as M. He was blond. He was white. He was ridiculously cute. He was polite. And best of all, he responded to my Craiglist ad! At the time, I was moving in some sort of emotional state between excited and apprehensive. I was worried that he'd turn out to be an axe murderer in an alleyway, or perhaps some old fat guy sending me fake pictures - so I wanted proof. But of course, this guy was totally out in the open, and he agreed to Skype me! The moment I looked into his eyes over the screen, I knew he'd be my first. He gave me directions to his apartment, and I left my room as my legs began to shake. I practically flew over to his apartment, anxious to know what sex feels like. Along the way, I was plagued with thoughts like "What if he has HIV?" and "What if he hurts you?" I could care less at the time. I had the drive. I had to know what gay sex was like. I arrived at his apartment door after running the entire 17 minute walk in under 10 minutes. I felt like puking while knocking on the door since I knew what was supposed to happen. The first thing I noted about the apartment was the excellent condition it was kept in. The bedroom walls were a beautiful deep red, and everything looked very clean and organized. I was extremely happy at the fact that it wasn't the same as the last place I had done anything sexual (a K-Mart bathroom). Once he opened the door, the butterflies in my stomach quickly went away. I felt comfortable within the first two seconds of seeing his face. I sat down on his couch, and we talked about how we both went to the same school for a little while. Since he was a junior, he gave me some advice on how to live by yourself and how to choose housing. After the minutes dragged on, I asked to use the bathroom - hoping it would be enough of a distraction to get the conversation to change pace a little. Thankfully, it worked. Once I came back, he leaned in. As soon as his tongue moved into my mouth, I quickly got into the swing of things. Our hands were flying all over each other as I straddled him on the couch and tore our shirts off. After making out for a bit, he suggested we move things to the bed. Bit by bit, the rest of our clothes were torn off as well. Once things were heated enough, I decided to be a little adventurous. I slowly kissed down the length of his body, all the way down to his perfectly sized dick. It wasn't small by any means, but I was thanking God that it wasn't the size of a grown man's arm! I gently licked the tip, and slowly moved down from there. I heard him moan a little bit, which turned me on even more. Then, I moved the lower half of my body to his face, and actually engaged in my first ever 69. I guessed that he had more experience since he started to go down extremely fast on me - almost making me cum. Of course, my major intention wasn't to do oral. I moved back over to him and kissed him a little bit more. Eventually, I could feel his cock pressing up against my ass. He laid down as I straddled him. I figured it was finally time! He slowly tried to push it in, and I could feel a slight burning sensation. As I moved down, I quickly realized that the pain was sharply increasing. Although I had never done this before, I knew what I needed. I whispered "Got any lube?" He directed me to the bottle on the nightstand next to us, and after a quick application, we tried again. The feeling was nothing short of incredible. I absolutely loved the feeling of him sliding into me. We started out in with me just getting used to the feel of a cock inside me for a couple of minutes. Afterwards, he asked if I wanted to try another position. It wasn't my intention to change my tone of voice, but I said "Missionary" with such childlike wonder that he couldn't help but smile and laugh at my naivety. Once we switched positions, he started to go all out. The speed started to rapidly increase as he drove down into me harder than expected. MY moans began to escalate to the point where he stopped and asked me if I was okay. I asked him to go a little bit easier. Fortunately, he complied. He lifted my left leg, and started pounding into me from a different angle at a gentler speed. Slowly, he moved faster and faster until he whispered "Wanna try doggystyle?" I could have died at that moment. I had always wanted to try doggy, so my excitement showed when I eagerly said "Sure!" I let out a little pant as he pulled out and pushed back into me during our repositioning, but quickly started feeling waves of pleasure as he started to pound me deep and hard. I had finally reached the point where there wasn't much pain anymore, and I could take a good, solid pounding from M. It was heavenly! I heard him moan a couple of times, as he started to shove into me a a little more slowly. Waves of pleasure and shock ran from my ass to my brain as I realized that M didn't have a condom on. I didn't really feel that much inside of me until he pulled out, when I could feel a couple drops of his cum leave my newly opened hole. As I cuddled next to him for a while, I was completely unaware of how NSA sex was supposed to work. I stayed a little too long and made it awkward as hell, but he was very nice about the whole ordeal. I haven't heard from him since then, but he was hot and polite enough to the point where I am glad he took my virginity! Immediately after, I started wanting more. I wanted to feel sex with a guy once again. So I went on Craigslist, Adam4Adam, and a couple of blogs to see how I can expand my sexual appetite. And that's how I became the cock-hungry teenager who wants nothing more than to enjoy himself with other men! Like it? Comment please :D Don't like it? Let me hear it! 1 You might like one of the following stories: Bicurious roommates Chapter 2 - An escalation(<10 minutes)Fiction - Blowjob, First Time, Gay, Masturbation The next morning, I awoke with a massive erection. Thoughts of the previous night’s “entertainment” made me excited but unfortunately there was no time to relieve myself. Bicurious roommates Chapter 1 - Yeah I told you was a pretty hot video(<10 minutes)Fiction - First Time, Gay, Masturbation So I got pretty unexpectedly hit by a long quarantine when all that trouble started. Unfortunate timing as it was during a work trip with a colleague. I won’t go over the boring details, but basically we had this studio apartment rented and we had to stay there for little over a month. BACKSTAGE PASS AT A ROCK CONCERT(15 minutes)Fiction - Blowjob, Cheating, Consensual Sex, Group Sex, Interracial, Male / Female I was wild in college. When my favorite band came to town one weekend, I decided to try to get backstage so I could fuck one of the band members. With my pretty face and big tits, I got noticed. I had to fuck the big, black security guard to get into the backstage party, but I ended up fucking the bass player of my favorite band, so it was worth it. Sexy BFFs Chapter 8(<10 minutes)Fantasy Jenny and Gracie go visit Griffith Observatory and meet a heavenly body. Sarahs Submission: Ch 03 - Bad Girls Get Punished(24 minutes)Fiction - Anal, Authoritarian, BDSM, Blackmail, Bondage, Dom / sub, Group Sex, Male Male / Teen Female, Pegging, Swallow, Teen Female / Teen Female, Threesome Sarah breaks his rules and he catches her red-handed. Sarah expects to get spanked again as punishment, but Mr. Michaels has a very different punishment in mind. She is forced to fuck the asshole school jock for Mr. Michael’s entertainment. | ||||