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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.

We're looking for stories about the first time you had sex. Email with 500-1000 words. (Don't worry, we won't print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.
FIRST TIMES
"I wasn't ready, but that seemed like a ridiculous thing for a teenaged boy to say..."
"I drove us to my dentist's office, where there was a vacant parking lot..."
"Of course the story he told everyone was sexier than what actually happened..."

Comments ( 10 )

This doesn't seem real.

CS commented on Oct 27 09 at 12:34 pm

This does sound completely fake.

SS commented on Oct 27 09 at 1:38 pm

Ugh. This doesn't happen in HS. Kids are way too insecure and high school is way too strict. I don't buy it.

RD commented on Oct 28 09 at 1:58 pm

I don't know what high schools are like everywhere, but this could have easily happened in mine. Because, what mbp said.

EKA commented on Oct 28 09 at 2:40 pm

wow i really wish my girlfriend was into that but alas* :( she dosen't swing both ways

CJ commented on Oct 28 09 at 7:17 pm

Rejected by Penthouse Forum apparently, and just had to put it somewhere.

KPS commented on Oct 29 09 at 1:03 am

Lay off you kill-joy cynics. Ive been in a very similar situation, altho i was 20 at the time, not 16, but its totally possible this story is legit. Even if it's not, its a fun read.

JB commented on Oct 29 09 at 1:36 am

some people did NOT enjoy their teens and must negate others experiences... when youre drunk, fun things can happen especially @ 16 when EVERY touch is tripled in sensation...

DMT commented on Oct 30 09 at 10:35 am

I have to believe it. People think this kind of thing doesn't happen in places like WI but I'm sure it does. I was an introvert but I knew many peers in HS that where going crazy. I was always jealous. I wish we all could so brave at such a young age. The courage does not change much as we get older I fear - except for a chosen few....

KS commented on Nov 01 09 at 8:50 am

i just don't understand the level of skepticism about this. this kind of thing happened at my high school all the time. teenagers are horny and reckless, remember?

tmp commented on Nov 02 09 at 5:25 pm