Let me start this off by saying I am not super experienced in dating at all and have never actually had a cougar/cub relationship in person.

I’m male, in my mid twenties, and have pretty much been focusing on school/work since I had my only serious relationship as a teenager. I’ve done nothing as an adult. For recreation I usually travel, I make plenty of money and work in tech and always thought I would start dating when I was ready to settle down, which I just decided I was ready for at the end of last year.

I think I’m a pretty handsome guy, over six feet, athletic, make good money, and when I started asking out a few girls and going on some dating apps at the beginning of this year I had no trouble with the ladies.

The more I looked though the more I realized that I was really interested in trying an age gap relationship, as that was what got me the most excited for some reason. The thing is I’m way more nervous to approach older ladies in person, and don’t want to use dating apps because I’m terrified of matching with somebody who knows my parents. I live in a SF so it’s a pretty big city but it seems like they know everybody. I decided to use Tinder passport mode and search in Thailand, since I had an upcoming vacation there anyway.

I matched with this pretty attractive 48 year old lady, and we hit it off super quick. I think it was really fun for her to have a romantic relationship with a young good looking American guy, and I was loving how much fun she was having with it. Like I said I hadn’t dated for about 7 years, and I’m not somebody who sleeps around, so physical intimacy/sexting was super new and exciting for me (still is tbh). We started doing that after a couple weeks because we just didn’t want to wait until we could meet in person.

One day we were just talking naughty and she asked if I wanted to get on a video call, and I said sure. She encouraged me to take my clothes off and show everything to her, and I did, and as soon as I was in that compromising position, she passed her phone to a friend! I was very shocked at first, but my adrenaline was pumping like crazy and I didn’t want to be that guy who chickened out, so I just kept going. It turns out there were five of them there and they all passed the phone around, some of them laughed and they all just watched me. It was nerve wracking, kind of humiliating, but also the best intimate experience of my life.

I wound up having to cancel my trip to Thailand, and I didn’t want to keep talking to her anyway because I was nervous she was screen recording or something, but six months later and I have not been able to stop thinking about it. I sort of stopped trying to date because everything just feels dull after that video call lol. I want to find something like that which could turn into a real physical relationship with a woman (or women) close to home, but I still have the same problems as before. Any advice from anybody? Is it a pipe dream? Once in a lifetime, something I can never find again?