I was really impressed with the story that Charlie wrote about his first kink experience, so I asked him to write up the experience he had when he lost his virginity. Enjoy!
I lost my virginity to a friend of mine when I was a teenager. A bit of background information; when I was younger, I played a fair bit of basketball for a local district team. The guy’s name was Jared, and while he was relatively attractive, he was very plain looking, with dark brown eyes, dark hair, and few distinguishing physical features making it difficult for him to stand out. Where he did separate himself from the pack was with his sporting ability. Captain of the cricket team, best and fairest winner for the football team, star of the basketball team; the guy was talented. We went to school together, and after we were put in the same district basketball team we became pretty good mates.
The team was pretty strong, and we were able to qualify for a tournament in Melbourne. The team stayed together in a motel, two players to each room. Naturally, Jared and I chose to stay in the same room. After a few days, we were eliminated from the competition, ultimately finishing fifth. Following our elimination, the players decided to have a little bit of a celebration back at the motel. Obviously there was some drinking involved, and by the time we headed back to our room Jared and I were both rather drunk.
In the motel rooms, rather than two single beds, as would probably be expected, there was a single double bed. When we got back to the room, we got into a bit of a stupid argument, and, as drunk people often do, we decided to solve it with a friendly wrestle. It ended up with me lying face down on the bed, him victoriously sitting on top of me pinning my arms behind my back. Curiously, I could feel his fully-hard cock poking into my ass, as he sat on top of me. This was surprising to me, as I was pretty sure he was straight, and he had had multiple girlfriends in the time that I had known him.
As if suddenly realising how hard he was as well, he tentatively began to move my hand down to his cock. I was soon pulling down his shorts, groping his cock through his underwear. He quickly got off my back and took off the rest of his clothes, eventually standing in front of me completely naked, his 7 inch cock standing proudly in the air. The vast amounts of sport he had played had left him with an impressive body, with quite clearly defined muscles running across his chest. He was hairier than I had expected, as he had quite a large amount of chest hair flowing from the bottom of his neck down to his cock.
I went down to my knees and began to suck on his cock. This was the first cock I had ever sucked, and I was surprised at how sweet the precum oozing out was. He used his hands to push my head further down his cock, and I gagged as it reached the back of my throat. He began to roughly fuck my mouth, and I could hear soft moans creeping out of his own mouth. After a few minutes of this, he pulled out, went over to his bag, and whipped a condom and a bottle of lube onto the bed.
By this point I was incredibly turned on, as I had never been fucked before, but there was also a bit of nervousness. As I was too young to be able to buy toys of my own, the only ass play experience I had was using my fingers. A couple of times a week I would attempt to finger fuck myself, and I was able to get in three or four fingers before it got a bit too painful for me. I didn’t really have anything lying around suitable to stretching my ass out with (like a bowling pin) and I was reluctant to use stereotypical vegetables like cucumbers or carrots, in the fear that I would go too far and lose them, resulting in a mildly embarrassing trip to the ER. Despite this, my excitement easily overcame my fear, and I pulled my pants and underwear off and hopped onto the bed on my hands and knees, sticking my ass into the air for easy access.
He popped on the condom, lubed up his cock, and slowly placed it inside my hole. It wasn’t nearly as painful as I thought it would be, presumably because the alcohol had relaxed me somewhat. He fucked me quite slowly in that position for a while, before he flipped me onto my back, pushed my legs up into the air and began to fuck me in that position. He began to pump much harder and faster now, and it was incredibly hot to see his face change and contort as he fucked my tight hole with his cock. He began to jerk me off, slowly at first, but getting faster and faster as he progressed. In only a matter of minutes, I shot my load, sending large amounts of cum up onto my chest. Seeing this only served to excite him more, as he began to pump even harder, fucking me with much more gusto than he had before. He wasn’t able to hold out for much longer, eventually shooting his own load.
He quickly pulled out, and we had quick shower together and went to bed. I remember that my hole was quite sore from the rough fucking, and the following day my coach asked me why I was limping slightly as I walked to the plan, to which Jared smirked as I stammered some excuse about being sore from the game. Jared and I met up a few more times, eventually exploring more stuff, before he got another girlfriend, and eventually moved to America. Still, it was a fun couple of months.