MY first dating experience was when I was 19 and I dated this guy Ken for about 3 months before he dumped me for another guy. I don't really count him as a boyfriend since we were only dating a few months, but I still call him my ex. Or first date started in the middle of the night. He picked me up and we drove around, parked for a bit and made out for a while. Then we went back to his place and fooled around. We only kissed and sucked each other, but he was the first guy to actually let me shoot my load in his mouth and then he swallowed it.

We didn't really share much except a good sex life, but when we fucked, it was with condoms. I almost always fucked him. He was the one to take my ass cherry. I really wanted to get fucked, and he was willing, so one day we were at his place and he broke my cherry with his condom covered cock. It got cut kinda short because he noticed I was bleeding. I was kinda freaked out and it put me off bottoming for a while, but eventually I got to the point where I was totally versatile several years later.

I ran into him about 10 year later at Pride and we talked a bit and caught up. He was being really flirty and said something about hooking up. I told him I was down so we ended up going back to my place which was only a short walk away. At my place we wasted no time kissing and getting naked. It felt amazing to have my cock in his mouth again. He sucked me for quite a while, then asked if I wanted to fuck him. I said yes and asked if he wanted me to use a condom, and he said it was okay if I wanted to fuck him bareback. I lubed up my cock and started pushing it into his hole. It was like fucking him for the first time.

I slowly slid my bare cock in and out of his hole, building up speed. I put his legs up on my shoulders and started driving my cock deep in his ass. He moaned in pleasure, not even jerking himself off. I only lasted a couple minutes before I sank my bare cock deep in his ass and finally shot my load inside him. He kinda giggled and said wow, that was awesome. He hadn't cum yet, so I asked him if he wanted to shoot a load in me as well. He said yes, so I lubed his cock up and then straddled him and sat down on his 5 and half inch cock bareback. I rode him up and down for a minute before letting him take over, thrusting his bare cock into me. He only lasted about a minute before he said he was gonna shoot. He thrust a few more times as his load filled my ass.

As I kissed him I pulled off his cock, and I felt his load dribble out of my ass onto his stomach. There was no blood this time, only semen.