Daring missed opportunity(ies)
 

Have you had any situations where you could have done something daring or even played game, made a bet etc but didn't take it

Probably. I spend a lot of time alone at work, so have ample opportunity to do all sorts of things "naughty" with little risk of getting caught. I don't, however, have much social interaction, or go out much. Work... home... repeat... with occasional jaunts to the store. The "highlight" of my week is when I have time/money to visit the local kink club.

Long time lurker here but am a big fan of your questions Andrew so thought I'd share.

I usually not quite enough brave enough. I used to be a proper goody two shoes, but when I went to uni, I started to come out of my shell. Offered to play a strip card game with a very hot friend, which he started but he bottled it.

Since then, there are a couple of good friends I've got naked in front of, but I always hold my hands in front of my dick. There are time I wish I was a bit braver and gone the full monty, but something always holds me back.

I'd love to have to go through an initiation/hazing - never joined a rugby club or anything like that, and that's a big regret. Being told/forced to take my clothes off, almost certainly get hard in front of people - would love to do it. Never quite brave enough to reach out and do it online - or in person.

I'm sorry that this is so off topic and silly, but I'm sort of impressed by your lurker mojo! This was your first post ever - and you joined in 2015! May I have the (somewhat belated) honour of wishing you welcome?

:D:p

Well I dared myself to send a nude pic to the You've Been Shamed feature that used to be in Love It! magazine. I was wearing a Christmas hat, back to the camera, fully naked stood up with legs spread wide open. Butt fully on display. Face turned to the camera. They actually replied saying they wanted to use it in an upcoming issue. But I chickened out thinking people will see it that I know. A few years later, I submitted the same pic and the newer editor wanted to publish it in an issue. I regretted chickening out.

In my first year of uni we had an introduction weekend we had a game where a group of people would try to hang the most articles of clothing on someone as possible. One guy went full naked and I wish I had done that too, even if it would have been cold and embarrassing.

A few missed opportunities at clothing optional events to be the only one naked because I was too chicken to get naked before everyone else :(

I think about this a lot I was in high school before I realized I was trans and was a lot thinner with g cups that I hid under baggy clothing.
There was a tree near the school that I would climb. One time I was high up and one of my friends told me to take off my shirt and wave it above my head. I didn’t do it. I wish I did if I did I’d have realized I was an exibitionist then, and could have had a lot of fun.