Where it happened: Hotel Room
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My first sexual experience was when I first started to masturbate. I has just finished 4th grade and had turned 9 a couple months earlier. I was on a camping trip with my uncle and we came across a stream and he encouraged me to go skinny dipping with him. While swimming the talk turned to a sexual nature and he told me about masturbation. Later that night when I was alone, I went to the top bunk in the cabin we were staying in and started stroking my cock. I had an orgasm but I was too young for anything to come out; I didn’t even have any hair at this point. Over the next several years, until I was around 16 we occasionally would fool around. We would skinny dip and sometimes suck each other off. We almost tried anal sex once but we didn’t have any lube and couldn’t get it in.
During my teens and early twenties I knew I was physically attracted to men. I also like women, but I liked men a little more. I had always been very shy and ever dated or had the opportunity to fool around with anyone of either sex. I also lacked self confidence which was in due to a large part that my cock was small, only about 4 inches.
Once when I was 19 I got up the courage to meet a guy I met in a chat room for a one night stand. We tried to do some oral but we didn’t really click. I tried fucking him in the ass, but I had trouble getting it in with my small cock. I ended up leaving without much really happening.
When I was 23 and living on my own I got up the courage to go to a gay bath house. After a while I met a guy who was interested and we sucked each other off. I came pretty quickly. I was planning to go back and try to have some anal sex and lose my virginity but it never happened.
When I was 24, I figured enough was enough of this damn virginity and I decided to lose it. I decided I wanted to lose it to a girl first. Although I had sucked a few cocks in my life, I never did anything at all with a girl, even kissing. So I decided to get a prostitute. I had roommates at the time so I decided to get a hotel room for the night and have her meet me there. I went out and bought a new pair of briefs for the occasion and got the room.
Although I am white and would prefer a white girl for my first time, this girl was black, which was fine too. She was damn good looking and I knew I could never get a girl like this normally. So I took off my clothes and she started sucking my cock. It felt good but I was just pretty anxious to get rid of this damn virginity I’ve held onto for 24 years. I always envisioned me on top in a missionary position but because my dick was small I couldn’t quite get it in, so I let her get on top which was easier.
She lowered herself onto my cock and it felt pretty good, but she was pretty loose and being small it didn’t make it the best combination. But it was still pretty good. I don’t think I lasted longer than a minute or two but boy I was sure happy not to be a virgin anymore.
That was about 6 months ago and I haven’t done anything with anyone since. I am thinking about trying to have sex with another man, so I look forward to writing about that.
Processing your request, Please wait....
