My First Time
The First Time I Was Paid for Sex
"A lot of sex workers talk about this feeling of crossing a boundary, the first time you’re paid for sex. It’s a transgression—once you’ve done it, you can’t go back. You’re marked by society for life."
Clown Sex and Toxic Threesomes: Five Stories of 'First Times'
This year, we launched our first podcast, "My First Time," focusing on all the "firsts" we encounter in our sex lives. Catch up on all our past episodes here.
The First Time I Had Sex After Transitioning
After Charlie Craggs started presenting as a woman full-time, she began having sex with straight guys—and came to realize firsthand how little they care about women's pleasure.
The First Time I Got Spanked and Realized My Fetish for Watching Men Get Hard
"But, even though I'd fantasized about getting spanked, the pain came as a surprise. Like, whoa, shit, that does actually hurt a lot."
The First Time I Had Sex With Someone While Dressed As A Clown
"When I was inside him he was looking at me, and he said, 'You know, I think this is the first time I’ve ever been pegged by someone in clown makeup.'"
The First Time I Had Sex with a Woman and Realized I Was Bisexual
"I started feeling this rush when I was around her and I didn't know how to pinpoint the way it made me feel. I'd look at her lips and think, I feel something."
I Had a Threesome with My Boyfriend and the Girl He Was Cheating on Me with
She looks at me and says, “Is it okay if I kiss your boyfriend now?” My gut is twisting, and I can’t really look, but I also have to look.