Love & Sex

My First Time

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Female • 16 years old • Milwaukee, WI

When I was sixteen, I had a boyfriend who was eighteen and a best friend that I wanted to fuck who was seventeen. She and I regularly talked about sex together, compared techniques, curves, and positions, and one drunk October afternoon we admitted that we were actually attracted more to each other than to our boyfriends, and that we would probably have more fun fucking each other.

We made plans to get some sort of toy. Then we downed the rest of a bottle of Smirnoff and started making out on her living-room floor. As she bit my nipples, I fingered her for the first time. Forty minutes later, she called her boyfriend to come over,

Illustration by Thomas Pitilli

I think just because she felt guilty for physically cheating on him with me, and emotionally cheating with me for months. The strict rules of high-school dating didn't bend for same-sex affairs. He was short, shorter than both of us, and mildly grossed me out. "Having fun yet?" he asked, as he walked over to me and squeezed my tits.

I was drunk and stunned, and I didn't want this prick to ruin my first lesbian encounter. I wanted to play with this girl on the floor and watch shitty horror movies later. I wanted to stay drunk the whole afternoon and taste pussy for the first time. I wanted to blame this all on alcohol the next day, and think about it for the next month. I was about to put my shirt back on when she came up behind me and put her hand down my pants, whispered she wanted me to stay, and then put a bottle of Jack in front of us.

I obliged.

She asked me and her boyfriend to come to her room, and they kissed for a minute, before focusing their attention on me. I had been accustomed to one mouth and two hands touching, but when it's two mouths and four hands, it's overwhelming, wonderful, slutty, and a little greedy all at once. I felt a little used, like a toy they needed to get off, but they made sure I was enjoying myself.

"I can't believe this is happening," they both kept saying. I let them both kiss, lick, and touch as much as they wanted, before I ended up falling asleep in her bed, pants off, and a blurry afternoon melded into a confusing night. I awoke at seven p.m. with a headache, kissed my best friend goodbye, and walked home not sure about school on Monday.