I was an introvert mostly throughout High School. I didn't go to many parties, nor did I have many friends, but for some reason I always found myself in situations in which I could potential hook up with a girl I liked.
Unfortunately, I had 0 skills on picking up girls even though I was trying really hard to get a girl.
In 11th grade there was a party around my school's christmas break, my closest friend at the time invited me to it. I was reluctant to go, but I eventually agreed.
I don't remember the exact date, but I went to the party and there was this girl that I'd seen before but couldn't really tell where. I still remembered her name though, Vanessa. She was pretty cute and I eventually convinced myself to make a move on her.
I stood there for a second, watching her, planning a way to get her to be interested in me. I couldn't come up with a plan, so I decided to just walk up to her and see what happens.
I walk up to her and say, "Hey." in the most seductive voice possible. She looks at me, smiles and says "hey" back. I decide to engage in conversation and the first thing that comes out of my mouth is, "Disneyland must have a lot of pedophiles, don't you think?"
Shit. I had said one of the strangest things my brain could think of. Vanessa stood there for a bit confused, but to my surprise Vanessa started laughing and said, "You're funny, I like funny guys."
I started saying more things.
She laughed even more.
I started getting excited, for the first time in my life I had gotten a girl. But then it dawned on me. I knew I recognized Vanessa from somewhere and I finally remembered where. A strip club. Vanessa was a stripper. Me and the close friend I mentioned earlier had snuck past bouncers about a year ago and got into a strip club which was pretty risky since we were under 18.
I got kind of sweaty for a moment as I realized not only was Vanessa a stripper, but she was also much older than me obviously. My little virgin self at the time could not take in these two thoughts at once. I began to get a little awkward, but still, she laughed at me and thought I was just funny.
After another few minutes of conversing she said to me, "Hey, I know the host of this party, do you want to get a room?"
Inside I was squealing with excitement, but on the outside I played it cool and just said, "Sure."
A few minutes later we were making out in a bedroom in the house. This was the first time I had ever actually made out with a girl, I had kissed girls before, but I'd never actually used tongue. I was ecstatic, I didn't know what to do but I guess I wasn't doing too bad since Vanessa seemed to be enjoying herself.
Then the most nervous moment of my life came.
"Do you have a condom?" Vanessa asked me.
I stuttered a bit and said no, she looked disappointed but got out her phone and called someone. A few minutes later we were interrupted in our make out session by the host of the party, who supplied us with condoms. I was so nervous/anxious that I could barely keep up the act of playing it cool on the outside.
The next part might get kind of graphic, so... yeah, just a fair warning.
In the next minute I had put on the condom and was starting to take off Vanessa's clothes. Finally, she was fully naked, as was I. She got up from laying down for a second and turned her back towards me, she wanted doggy style I guess.
Before I put my dick in her she said, "wait". Kind of annoyed by the sudden stop, I said, "What?" Without looking at me she said, "Put it in slowly, I'm actually a virgin." I couldn't believe it. This girl who was older than me, a stripper, and had been extremely aggressive was a virgin. I still can't believe it. I asked her if she was serious because I was in shock. She said she was serious, she was looking to lose it tonight and she didn't care whom she lost it to. I told her I was a virgin too and she said good. As I was putting it in she said, "Wait, I need one more thing.." "What do you need?" I asked.
"I need about tree fiddy." It was around this time I realized that Vanessa was 8 stories tall and a crustacean from the paleolithic era. "Damnit Loch Ness monster, I ain't givin' you no tree fiddy!" I said to her as she swam away into the distance.
Topic: Awkward Sexual Experiences (Read 464528 times)