Derek
Age 37. Partnered. Gay.

Age 11
First Kiss
My friend Ari was leaving my house and kissed me goodbye on the lips. It didn’t feel right.
Age 14
First Kiss (With A Boy)
I kissed a boy on the lips. It felt right. He was my best friend at the time, so it also felt wrong. We blew each other one and a half times, but didn’t think it was gay because we wore blindfolds.
Age 18
The Bottoming Era
My boyfriend at the time designated me "the bottom" in the relationship. I didn’t like to bottom, but he was not very well endowed, so it wasn’t a big leap. God bless.
Age 25
Meet You At The Top
I met him at a juice bar, and we were together for six months. Our sex life was horrible. But then one day, I realized I was a top, and I enjoyed sex for the first time.
Age 27
The Messy Breakup
I got dumped by the biggest loser and went abroad to visit with my best friend. I was a mess. We were at a pub when a woman approached me and told me she selected me to fuck her husband. We tried to have sex in the stairwell, but it didn’t work.
Age 28
South Park
This insanely hot country boy closet-case came to my house for a hookup. He sounded like Cartman from South Park. He wanted me to choke him. I didn’t want to. He was very dissapointed.
Age 33
Basement Irish Boyfriend
At the start of the pandemic, I lived with my boyfriend in a basement apartment because dreams can come true. I think he was Irish - he pronounced “potatoes” weird, so I just kind of assumed.
Disclaimer: All names and identifiable details have been modified to protect the reputions of our contributors in the eyes of their partners, colleagues, and parents.





