Where it happened: Motel room
Langauge: English
Sex: Male
Rating: 6
Category: Straight
I was never one of the popular kids in school. I was severely overweight and never even had a date until I was 18 and had lost over 100 pounds. After that, I had a few chances at sex, but always backed out. I was just plain scared and didn’t know what to do. The farthest I had ever gotten was fingering an ex-girlfriend. But early 96, I finally had my first experience, and with an older stripper no less! I had went with a couple friends to a local nightclub to see a friends band play. I was standing against a wall shortly after they had finished their set when this woman walks by, starring at me. I can’t remember exactly, but I think she stopped, walked up to me and introduced herself. She was about 5’8″, long blonde hair, 150 pounds (not fat, just a bit chunky), C-cup, and I think she said she was 28. Anyway, I remember her asking me to have a drink with her, which I did. Then another, then another, ect. Anyway we talk for awhile and keep drinking. She tells me she’s a stripper at a popular local stripclub, and I’m tripping. Can’t say I’ve ever had a stripper come on to me up until that point, (and haven’t since). Then she brings up the fact that she has a room rented at a nearby motel because she didn’t want to drive drunk. I was planning on just getting her number and going home. But my friends told me to go for it. So I just said fuck it and went with her. We get there and I learn that her brother and his girlfriend are also sharing the room. They’ve got a full 12 pack there, and we start drinking some more. Then we start kissing, and the clothes start comming off her. We get under the covers and I begin fingering her. And somewhere during this time, her brother and his girlfriend (who have a seperate bed) start fucking. Keep in mind that I am on the verge of my first sexual experience, and I have to perform in front of her brother and his girlfriend! I was freaking out almost to the point of shaking. But I kept my cool and kept going. Anyway, I fingered her for what seemed to be forever. Her brother and his girlfriend finished up and went to sleep, because she wanted to wait until they were asleep. Then I finally got undressed and she started stroking my cock and told me she wanted me inside her. We had the covers over us, and not being able to see exactly where her opening was, it actually took me a couple tries to finally get it inside. I remember she was soaking wet once I actually entered her. I can still remember being supprised at just how wet and hot that pussy was. I remember I was laying on my side in a real uncomfortable position for the whole time. And I remember looking over and seeing her brother’s girlfriend watching! I actually thought I would be intimidated having sex with a stranger in front of two other strangers. But it actually turned me on something fierce, watching her watch me pound this chick for all I was worth. Needless to say, I lasted all of a good two minutes before I came. I couldn’t hold out! Obviously she wasn’t impressed. I gave her my number and she gave me hers and I went home. I called her a couple of times, but we never got together again. Great memory though! Thanks for reading!
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