Anyone out there have any regrets about “missed opportunities” to enjoy a sexual encounter? For example. I was visiting a friend and we ended up naked in their outdoor hot tub one evening in the middle of a light snowstorm when my buddy’s wife said, “oh, I almost grabbed you by mistake”. Turns out she wanted to play with both of our manhoods at the same time. My friend asked me what I thought about that and I was so flustered, I mumbled something about not wanting to do anything that would hurt our friendship and things moved on. That was then, this is now and I regret passing that opportunity by. Another example, many years ago now, I was having dinner with my boss and his wife who casually mentioned they were swingers and on the lookout for willing participants in a MMF. I was young, stupid and passed that opportunity by. Looking back, I wish I hadn’t. How about you? Any regrets?
There was a bloke I met in the street. I wanted to give me his number to hook up, no pressure, and I said no. It felt dangerous. I do regret it though. Would have been no harm taking a number, though, and I may well have been able to work out how to do something safely. After all, how is meeting someone on a street any different from meeting them in a club? With hindsight, it is probably no more dangerous. I do regret that.
I also regret staying with no hope boyfriends for too long, although I suppose I can’t regret it too much as it is how I ended up with my husband.
I regret ever going with my first boyfriend. Believe its that relationship that gave me trust issues around men although having said that my instincts have saved me a few times so i suppose i learned an important lesson. I dont trust people in general as in my experience they want something from me normally money or sex. So if someone was to be genuinely just being friendly i can appear to be standoffish with them.
@HoneyBadger1 Might have been a bit awkward with the boss and his wife, do something wrong and your out of a job so was probably for the best.
A bit off topic but I regret not having the balls to tell my wife what I would like sexualy 
Texting makes this easier.
If you are ever away and jusy chatting over text just tell her you are craving her. Then she might ask what would you like to do to her and you can open up a bit.
I done this years ago and it definitely opened the doors. Now I just tell her what I like.
Samantha here. About 5 years ago when I split with my ex i was meeting guys from tinder and just going abit wild if im honest. 1 guy used to go to swingers clubs etc. He invited me to a party one night with a male friend of his. The plan was for me to try dp for the 1st time as he knew it was my fantasy. The date was set for a couple weeks time.
I ended up backing out of it. I had only slept with him twice before and the other guy was a stranger. There was no trust there. Sometimes I think back and wish id just done it. 
I’m pretty sure there’s been many an opportunity I’ve missed out on but then I’ve always seen them as 50/50 in that would I enjoyed it or just got murdered by a stranger 
When I was younger I was always too scared to make the first move. There were women that I was interested in but never even told them out of fear of rejection. Years later I would find out that some of them were interested in me too and I wasn’t picking up their subtle clues 
The joys of neurodivergence.
I actually think most of my regrets revolve around being too shy to just make conversation with lovely lassies when I was younger! Always remember a lovely lass who used to travel on the same train as me, got as far as exchanging smiles and regretted opportunities to speak to her - didn’t even pluck up the courage to pass comment on late trains quite often shared with other passengers!!! The only other regret was not flirting with an attractive neighbour who was telling me about the short skirt she was wearing on a night out she’d been on - not that it would have led anywhere but would have fuelled my early 20s fantasies!!! 
@jasonmax, you hit on something there. I recall looking back at my old high school yearbooks not to long ago (major geek alert here) and going through all the written comments I’d collected in them from fellow school mates. There were several - over years - from a woman one grade below who as I read them now, clearly showed an interest in becoming more than just school mates. Missed the less than subtle hints completely. Made me wonder how many other times I missed and/or didn’t act on similar situations. Ah yes - the joys of hindsight.
Not getting fitter in my teen years to pick up girls, only did this in college.
Not cheating with a 30 year old when I was early 20s. My gf at the time left me for someone else, so having a time machine I wouldn’t feel bad.
Early 20s, a 40 year old woman winking and smiling at me in a bar with her friend. I freaked out and ignored her. Regret that one, it was a proper summers evening as well so it would have made for a great golden memory.
Had an ex who would have been into sharing, should have experimented with that.
All sexual regrets of course 
What sort of things would you like? Are you worried she might reject your desires?
I had the same problem when I was younger.
I was totally oblivious to people flirting with me when I was younger and looking back with older eyes I realized a lot of boys tried to ask me on dates and it completely went over my head. One guy used to work at an ice cream shop I would go to some afternoons and I would order the same thing. After a while he would have my order ready waiting for me, plus slip me a box of free donuts and ask me about my day/what I was doing later. I thought he was just being nice. I need people to verbally tell me that they like me, and even then I don’t believe them. (neurodivergent)
I have so many fantasy’s to try with her but my confidence level to even try and start a conversation is -1000 so I just Berry them and don’t even try
Maybe you could make a list of things, and decide on one that seems pretty simple and bring it up to her? She might be more interested than you realize 
There was someone I was sleeping with for a while, and it was working really well. It was purely just sex for the two of us and we explored some really kinky stuff together and had plans for much more. I ended up stopping that because there was a lass I’d been flirting with and felt like it might go somewhere.
Turns out the person I’d been flirting with who’d made some pretty emotionally overt comments to me just liked the attention and didn’t actually want me, and just wanted me to make her feel good
I’m happily married now and wouldn’t swap this for the world, but I do regret not having a chance to explore a few of the things we’d not yet done with this fuck buddy, as I know they’re things my wife isn’t in to or doesn’t want to try. Yes I know this is incredibly selfish, so this is an entirely sexual regret and nothing else.
After meeting a random guy in a pub and going to his to play PS3 (a while back now) he started to grope me and i didnt stop him as id gone a few years without any action and had had a few drinks. Wasnt long until he had me naked, sucking my cock and running his hands all over me.
I was so nervous that once i came i just got dressed and headed off. Always regretted not doing more. Not long after that i was married but split from wife a few years back, but instead of trying to experiment when single i instantly got with another girl who im still with now!
She knows about my guy experience and herself loves gay/bi mmf porn which we watch together talking filth to each other about how that would be us. She knows id love a bi mmf 3 way with her but she said its never happening and for her its only a fantasy…..
I was 18, still a virgin, and was at a friends 21st birthday. I was having a slow dance with his girlfriend, she was wearing a wrap aroud fairly short dress, and she somehow got her leg in-between mine pushing up and stimulating me whilst semi wrapping her other leg around my leg and rubbing her pussy on my thigh. She was moist and hot and she could obviously tell I was aroused she whispered in my ear she wanted to take me outside and Fuck me. I shit my self , said no and broke away from the dance. To this day 45 years on I still deeply regret my decision. Although when I got home I did have an amazing Wank thinking about her and what could have been.