For all my bluster and bravado, it was last august, right after I turned 18.
I went to a really small high school, with basically no dating pool. I had never dated anyone during high school.
After I graduated, my brother started rushing me for his fraternity.
At the first fraternity party, my brother brought his girlfriend, and she brought two friends of hers from work.
The older of the two friends started coming on to me, and we ended up making out on the dance floor.
At first I was so nervous about what I KNEW was going to happen that I tried to ditch her. Jake wouldn’t let me. Thanks, Jake.
I was really drunk by the end of the night, so the younger of the two sisters drove us back to my brother’s apartment. He stopped me in the hallway and handed me a condom.
After we got into my brother’s roommate’s room (he was gone for the weekend), there was knock on the door. I opened the door, and my brother’s girlfriend handed me two more condoms, and said “Just in case…”
We ended up having sex on the floor because the bed was a waterbed, and I was a virgin, so it was going to be hard enough as it was.
We had sex twice, and I was trying to fall asleep, as I had a job interview at 9:30 the next morning and it was nearly 2 am already. She wouldn’t quiet down and sleep, she kept rubbing herself and trying to give me a handjob.
Finally, she rolled over and said “Do you Americans like it… how do you say… doggy style?” I was back in action.
Finally, around 3 am, we finally went to bed.
I got the job.
My brother’s girlfriend called me a few days later, and said Isabel wanted to thank me, because she had decided from that to break up with her fiancee.
Isabel turned 22 the next week.
I never saw her again.
–Tim