Back when I was 19 and identifying as just gay, not pan or bi,I got to examine the difference between an implant and a natural boob because of a luggage snafu that had me, another gay guy, and 2 girls sharing a hotel room for a night. The girls wanted us to see if we could tell the difference (we could not).

That's as close to a porn scenario I've ever been. And it didn't even lead to sex.

Yes there was this girl and me and then we were having sex.

I told both these stories on LemmyNSFW, but I'll retell them here

In college I worked pizza delivery. I was delivering one Friday night and a woman in a big house opened the door in a nightie and pulled the "Oh no, I just realized I don't have any money. Is there anyway else I could pay for this?" trick. I had a girlfriend at the time and I had multiple deliveries to make, so I was just like "Oh, don't worry about it, I'll cover it."

One of my exes was helping her mom out at a local church, so we were in the back organizing stuff. After a bit, everyone but the two of us left to go do other things, so it was just the two of us alone in the church. We looked at each other and were like "Want to sin a little?"

I have had some interesting moments.

One, I turned down. I had loaned a coworker some cash, and she suggested paying it back in trade. She did so while lifting her skirt to show her quite bare and wet pussy.

Another that I turned down was a neighbor that seemed to enjoy going without underwear while in the yard, bending over far more than necessary and watching for my reaction. She was under my acceptable age though. Legal, but I have firm standards about power dynamics.

One that I very much enjoyed accepting was when a friend of my mother's asked for some computer help. While not an expert, I knew more than anyone else she knew.

She had me open a folder "by mistake" that contained some very lovely pictures of her. She pretended to be embarrassed, apologizing. Then, as I was telling her not to worry, she asked if I had liked them. Then, when I said yes, she started undressing and said "then you'll love this." I did. I very much did. After a wonderful experience, she asked if I could actually fix her email. I did. That was much less fun, but as a reward, she knelt down under the desk while I worked and used her mouth to communicate her gratitude.

Landlord (company) was renovating the entire block, new pipes, bathrooms, and kitchen. The renovation company put a machine that let the workers unlock the doors to the flats.

A lot of people got temporary units to live in. I did not.

Saw one of the workers on Grindr. We hooked up, and after that word spread to a few of the other dudes.

So I got a health check up exam for work once and my regular doctor was out on maternity leave and there was this other super hot and busty doctor that filled in. She had to do that testicular cancer check and literally got down on her knees and pull my shorts down. I almost heard the pornhub snares lol. Nothing ended up happening but it was so odd the way it happened.

While I won't go into detail, in my younger days I partied some, which included sessions with a room full of people. Five or six at times.

The reason for no details is that it wouldn't be polite to discuss a partner's activity in that regard without express permission, and I have no way of getting said permission from most of them. And, tbh, I'm not asking the ones I am in contact with because it just seems rude.

Yup. Actually quite a few times now. My life has gotten unreal since hormones.

We've done a glory hole at an adult theatre in Amsterdam, that was a lot of fun most cocks I've ever had in a single night. I got to live out a fantasy of getting multiple facials and Husband got to live out the fantasy of fucking me with lots of cum on my face and then adding to it.

When I was in college, I did a scenario where a security guard “discovered” me in the bathroom as a trans guy. It was pretty fun - he let me into a botanical garden after hours which was a nice and scenic setting.

I've had sex at a college campus, but not in any dorms. Public spaces after hours.

I worked at a resort after HS and had sex with a few people staying there.

Nope never been that lucky

I lost my virginity in an ambush threesome.

Things have just gotten weirder since.

When I lost my virginity, she randomly showed up at my house in the middle of the night. I thought something was wrong. She was only wearing a coat and a bikini. She had me lay on my bed, got on top, and put me in, rode for a couple thrust, came, then left. Couple days later we broke up.