My first simultaneous orgasm, and the first time I tried anal [MF]

Five years ago, I was in the unfortunate situation of having broken up with my girlfriend, but still living out the lease together. Yikes, I know. So I did my best to get out of the house as often as I could. One prong of this approach was to post and respond on the r4r subreddits: /r/dirtyr4r, /r/BaltimoreAndDCr4r, even /r/Troll4Troll. Yes, there is such a subreddit, which I only found through using the somehow then-working search function and looking for “f4m” and “VA” or “DC”. It was there that I found the (long since deleted) post that described a 27 year old woman who was traveling for work and would be in town for a week and was looking for a date. I messaged her and described myself, a 25 year old 5’10 athletic guy with brown hair and a beard, a lot of chest hair, and some tattoos. I included a picture and listed a few interests, but didn’t get my hopes up– internet personals aren’t known for their high response rate.

My friend brought me to her rooftop overlooking the city to ask me a favor [mf]

This takes place a couple years ago, but I met Lisa about a year before that. I was dating another woman at the time and we posted on reddit looking for a third to join us in the bedroom. Lisa (not her real name) responded to our ad and expressed an extreme interest in exploring her bi side. We traded pictures, talked about bedroom stuff, yadda yadda… but by the time the day of our date rolled around, she had to cancel because she had just started seeing someone. So I was bummed, but no big deal. We kept in touch and I sent her sfw snaps occasionally.

Several months later, we reconnected, and eventually did see her in the context of a threesome, but that’s a story for another time. After said threesome, she decided that women weren’t really for her, so again, no biggie, We stayed in touch and I even went rock climbing a few times with her. It was apparent, however, that there was still chemistry between us. And at the time, my partner and I were in an open relationship, so while I wasn’t sure what Lisa wanted exactly, I was definitely open to something sexual.

I met a hedonist on reddit who let me hone my massage skills [mf]

A couple years ago, under an old account, I posted on the local DC subreddit and raomd soliciting for, well, muff diving. More specifically, I extolled the virtues of my massage skills. I’ve never had any training, but I’ve watched a lot of videos, learned by experience, have tons of enthusiasm, and strong fingers thanks to rock climbing. As most m4f posts do, I got only a few responses. One stood out to me.

She described herself as 30, blonde, average height, in above average shape, and living in a neighborhood adjacent to mine. She admitted that she hadn’t been physical with a guy in longer than she’d like to divulge, but that her hormones were driving her nuts. She missed having a man touch her, massage her, and go down on her, and that she’d gladly verify herself off of reddit. We moved to kik and she sent me pictures… jesus. She was in peak shape. She had visible abs and a killer ass. She admitted to hitting the gym quite a bit, and I could tell. Her pictures didn’t include her face, as she wasn’t comfortable sharing that because of her job, but that she was conventionally attractive. I gave her the benefit of the doubt– she was honest about her being in shape, after all.

My friend at the gym had me fuck his fiancee [mf] [hotwife] [cuckold]

Before quarantine, I went rock climbing a lot. Every day, if I could. I’d spend three or four hours at the gym, take a yoga class, read between routes, etc. I even subbed as a yoga instructor a couple of times, just for fun and because they needed a fill-in. I wasn’t really there to meet people, but I did get to know a few of the regulars over time. Matt and Alli were the couple that I saw the most. Matt struck up conversation after noticing a few of my Zelda tattoos, which were on display in any of the tank tops I’d wear. I wasn’t *trying* to show off– I’m just hairy and tanks have always felt more comfortable– but I can’t say I didn’t enjoy people being able to see my body. Average height, but in the best shape of my life at 30, and some women dig the tattoos and the beard.

I went to a festival and took molly with a stranger [mf]

Bad idea, I know, but hear me out.

(Disclaimer– I realize this is pretty long but I always like reading the meet cutes and flirty bits in these posts. I marked where sexytime starts if that’s your jam, though.)

It was the Landmark Festival in DC, back in 2015. I was really only interested in the Sunday lineup, but my friend wanted to see Saturday too and it wasn’t that much more expensive to get the two day pass, so I caved. My friend, Billy, ended up getting wayyy too drunk, so I ended up sorta taking care of him via frequent trips to the stalls and concessions for water. I tried to lobby for going home, but he was a mess and got stubborn in that way that drunk people do, so I relented and started dicking around on my phone.

So after one of these futile arguments, I noticed someone in my peripheral looking at me and sorta smiling. She said, “What can you do?” I wasn’t paying attention, so I kinda just nodded and laughed, but she added, “My friend does that all the time. She’s booting right now, actually.” Something about her tone got a more genuine laugh out of me and I replied that we should introduce them. She laughed too, and I turned to face her, and with her face lit up like that, I really noticed her.