Illustration by Thomas Pitilli
Male • 19 years old • Alabama
Sophomore year in college, I had a girlfriend whom I'd been dating for a year. She didn't want to have sex until marriage. I respected that, but as a teenage boy who'd never had sex, I felt pressure building.
One weekend, I went on a "team building" trip in the mountains, away from my girlfriend. It was full of new freshmen, one a girl named Lisa who was extremely friendly towards me. She'd tease me by taking my papers, smile at me, and sit next to me when she could. I knew she was crushing on me.
The first night of the trip, I was staying in a lodge with four other guys. We were just hanging out in our room; Lisa found me and came in to hang with us. When the time came to go to bed, I invited her to stay the night in my bed, on the bottom bunk, while four other guys were sleeping around us. Bold, huh?
She agreed. I had no intention of anything sexual happening — I had a girlfriend. But then our bodies began to rub and our pelvises began to grind. She made moaning sounds, and I didn't want her to disturb the guys sleeping around us, so I kissed her. I was sleepy so I wasn't thinking straight. She apparently liked it, and we started making out. Our hands wandered. Hers went into my pants, mine under her bra. Eventually, she gave me a hand job, and I came on her stomach. I could tell it wasn't her first time giving one. That was the end of the night's activities.
Once we returned from the trip, I had no idea what I was going to do. Could I really try to have two girlfriends at once? What if one of them wanted to be in a relationship on Facebook? About a week later, my original girlfriend was staying in my dorm room and Lisa called. I didn't know it was her until I picked up, and she said she was out front and needed me to let her into the building. Being nice, I did. She came in. I introduced Lisa to my girlfriend as "my friend," and that was when things got tense. Lisa wanted to stay the night. My girlfriend was already in her pajamas planning to stay the night. They obviously couldn't both stay.
Taking Lisa out into the hall, I explained, "My parents don't want me to have a girlfriend. They want me to focus on studying." I also said that my friend in my room was having a bad day and I was taking care of her. I was in essence breaking up with Lisa; she cried, but said she was okay. I walked her back to her dorm room across campus, and she wanted to "kiss goodbye." Our kiss turned into a makeout session which then turned into the question, "Do you want to have sex?"
We agreed we would, and the clothes came off. I raided her roommate's condom stash, and lay on top of her. When I entered her, she said, "Slowly!" I began thrusting, kissing her. She moaned. But because I had to pee, I was extra sensitive, so I came in about a minute and pulled out. Lisa didn't really seem to mind. We cleaned up, and I kissed her goodbye, saying that we would stay friends. I was embarrassed about my performance, but I had to get back to my girlfriend waiting in my room before she got suspicious.
Returning to my room, I told my girlfriend that Lisa was a girl who liked me, and that she'd been crying in the hall because I'd told her that I already had a girlfriend. My girlfriend accepted the story, and we went to fool around in bed with my body still covered in another girl's sweat. So my first time was cheating on my girlfriend with a girl I'd known for about a week and had just broken up with — and it lasted for only sixty seconds. I am a horrible person.