[MF] Giving my friend her “firsts” (Part 1)

Mary had been trying to flirt with me for over a year now. I had decided to play dumb instead of making an issue over it. It was easier to just pretend I didn’t get what she meant or deflect the topic entirely. I didn’t want to make things awkward. I’d known her when we were both much younger and we’d only reconnected a few years earlier. But she was good at flirting subtly, I’d learned since we started talking again. The subtlety made it easy to ignore.

But that changed one summer. I couldn’t just ignore it. She decided to me perfectly blunt with me, and I returned the favour. She told me that she’d had a crush on me for as long as she can remember. Even though we hadn’t spoken in many years, we ended up with a lot of the same interests and hobbies. I don’t know how much of that was natural or how much of it was trying to emulate me. Either way, that’s how it turned out.

I had explained to her that I didn’t feel the same way. There was a fair age gap between us and at the time that would make it impossible for us to be together.

[MM] My first experience with another guy

I had just broken up with my gf about a week before this. I know, a lot of stories start this way. I think I’d always known I was bi. I remember playing with another boys dick when I was really young and it always stuck with me. I had to try it for real now.

I set up an ad on some website that was popular in the early 00s and waited. And waited. And waited. No responses. It was a paid site so that’s no surprise. Then I started browsing ads that were on there and found one that stuck out. Someone, like me, recently single and inexperienced with guys. So I bought some credits and sent a message. Luckily I got a response pretty quickly. He was around my age, early 20s. We chatted for a couple nights about what we wanted to try, our reasons for doing it, and what we expected after. It was to be a one time thing since neither of us knew if we’d enjoy it or not. He didn’t live far away, it was almost on my way home from work. We set up a date and time about 2 days in advance. I was alternating from excited to nervously anxious the whole time. On the day of our meeting I spent my shift in a bit of a haze.