[MM]y first time getting fucked by a man. I called him Daddy, and we’re still in touch, 10 years later.

*Note: this is the account of my first time having M-M sex, lightly edited to accommodate the sub’s rules. I’d done some stuff before that, but can’t go into it here.*

I was one of the older kids in my class in high school, so I turned 18 the October of my senior year in high school. Our travel soccer team season was well underway at that point, and I was going with the team to games every weekend and 2-3x per week for practice.

Now that I’m a little older, I realize now that my travel team soccer coach had probably been waiting for my birthday to come around, because he asked me to report to his place one late Saturday morning before a game. Coach Jim was a pretty stern guy – mid-40s, sharp features, close-cropped hair, very hands-on and competitive. Very “coach” type. All the dads loved him. Coming to his place wasn’t that unusual – a bunch of us often assembled at his place and then carpooled to the game that weekend. But this time, it was just me, and it was like 3 hours before the game. My parents dropped me off and I went in.

Mostly straight, except for that time I was a slutty male prostitute for fun in college [MM]

So I’m an extremely normie suburban dad in my mid-30s. You’d probably call me a bro. Wife and two kids, the whole thing. She has no idea that, when I had just entered college, I was a male prostitute for a while.

At the time, I was an eighteen year old college freshman. Literally the first few days on campus. I’d had an experience or two before that (which I won’t elaborate on publicly, per reddit rules ?), but I was your pretty standard straight white fratty guy. Played HS football and liked to flirt with the cheerleaders, all that. I got this email from a guy near campus looking for students who were looking to make some money. The text sounded like he was looking for movers or landscapers or something – a couple other guys on our hall got the same thing. I was the only one who followed up on it, because it just so happened that I’d dinged my dad’s car over the summer and needed the cash to pay him back.

My FWB, the Mouth Slut [FM]

So a few months ago, I met this girl, Chloe, on tinder and we got a drink together. She’s cute, about two years out of college, your typical “working my first corporate job in the big city” type. She’s short, about 5’3, dyed dirty blonde hair, brown eyes, proportional and perky tits. I’m about ten years older than she is, and she admitted a preference for older men, which… hey, I certainly can’t complain about. We had fun but I didn’t see us dating, so afterward I sent her a message that it was fun hanging out but just wanted to be clear I didn’t see it going anywhere. She said she’d felt the same way, but she’d had fun meeting me. No big deal.

About two weeks later, I see her again at a bar. She’s out with some girlfriends and looking cute – short skirt, tight sweater. I buy her a drink to show her there are no hard feelings and she appreciates it. I go back to my friends.

[FM] My little sister (21F) sucked off six guys in a row in front of me, and now things between us are… interesting

I’m in my late 20s and my little sister (Julie – not her real name, but not far from it) is still in college. She and I have always been close. We weren’t close enough in age to really piss each other off, I guess, and she comes to me for advice now and stuff. We’re also pretty open about our sex lives. Nothing weird, but I know what she’s into, what kind of guys (sometimes girls) she’s into, and likewise, she gives me tips on girls. She’s even hooked me up with friends of hers in the past. It’s a good deal. She’s a good looking girl – curly dirty blonde hair, cute face, C-cup tits and a great ass. Yes, I notice this stuff, even though I’m her brother. Yes, I’ve jerked it thinking about her before. Whatever, don’t judge.

So a few weeks ago, Julie comes to me with this request. She wants to go try something, but wants me around as “backup.” I’m… unsure, but have her explain it to me. Basically, it goes like this: