Going back in time/missed opportunities

Sex Tips & Talk
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Does anyone have any missed opportunities in the past which they would fulfill if they had the chance to go back in time? Here’s a few of mine…

The first one was with my first ever sexual partner, a confident curvy young lady with a voracious appetite. Early on she said her biggest fantasy was to have a threesome with two guys. At such an early stage in my sex life this was a bit much for me but would love to go back in time and have helped her fulfill this. Also she used to wind up her gay friend telling him ‘theres a naked man’ here, when I was (hurriedly) getting dressed. Going back in time though I’d have taken my time dressing and given him something to see.

Next one, another missed threesome opportunity. A few years later a friend of mine delighted in telling me about a v adventurous girl he was seeing casually who wanted a threesome with 2 guys. She was attractive and apparently thought I was fairly cute but at the time even though I was single I was besotted with someone else and foolishly passed up the opportunity - silly me.

Another time was with an older woman who was v keen on anal play (on me). It took me a bit by surprise and I moved her hand away. Fast forward a few years and this is something I’m really interested in so would definitely go back in time to relive that and also relive being with a 40 year old whilst I was in my early 20s!

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The only thing I regret sexually was not finding out till my late 60’s about male chastity which enabled me to discover that I am submissive, enjoy pain and love extreme anal play.

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There was one guy I regretted not hooking up with. He pulled his car over in the street (caused a massive traffic jam) and gave me his number. I was with someone (a loser) so I did nothing with it. I often wonder…

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There have been numerous opportunities in the past almost five decades that I passed up due to my built in moral compass . There has always been two that I lived by and one was to never fuck a friend’s girlfriend and the other to never cheat on my wife . I had a number of friends that told me their wife would like to screw my brains out and that was OK with them . And then there were chance meetings with several extremely sensual ladies that invited me over to christen their new luxury condos . Funny how during the almost 9 years between wives and when I was peaked at body building I had similar things happen , the memory faded . But several of the offers I turned down can still haunt me today . However several are fuel for sexual fantasies during self play . But I still stand by my decisions .

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Those are both amazing qualities in a man and you should be proud.

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@Alurkingnewbie

i guess we all have things like that

I kinda wished i was a little more outgoing in my early 20’s, i was really focused on my career but wished when i was at my “peak” physically i did some wild things on girls holidays or just hooked up with more people

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Sounds like you past on some very big opportunities but yet maybe this doesn’t mean they won’t come again as a possibility to partake in a threesome :slightly_smiling_face:
Many believe things happen for a reason even though that reason isn’t as clear until it happens lol

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I haven’t got any missed experiences to fulfill. The only thing I might possibly change would be ending my marriage earlier that would’ve given me more opportunity for depravity.
But I think thats come at a time when I’m able for it.

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Personally I am very happy in my life (both sexually and otherwise) so I wouldn’t risk changing anything.
Sure there are things that I wonder how they may have played out if I’d made different choices but not at the risk of changing what I have.
I count myself very fortunate to have had a very adventurous life early on before I got old and boring. By the time I was 30 I had lived on 4 different continents, visited almost 40 countries, had partners in most of them :wink: .

I settled for a while in the USA, worked in Hollywood and dated a movie star / singer / model, I guess that’s the biggest one for me. It’s not so much a regret or anything I’d change as I am nearly 20 years happily married, but I do sometimes wonder how things would have gone and where my life would be if that had stayed the course - especially when I see her in an article or on the screen. I’d like a peek into that parallel universe for a moment.

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Oh my. The list is long. A lot involved being extremely work oriented and not paying enough attention to one of my wives.
Another was being really stupid about missing the opportunity 58 years ago to have a long time relationship with the gal I’m with now after reconnecting after my last wife died. Back then it was because I liked slim women and she is not. Really, really dumb.
Then there are pure sex related missed opportunities. Not finding out I like anal play on myself until much later. None of this extreme pegging etc. but just rimming and gentle finger playing.
Another, and I run the risk of getting crap over this but I dated a couple of African American gals (actually one was I think Jamaican) who had fabulous bodies and would fuck my socks off. But I love giving oral and couldn’t take their bushes. Brillo pads was a term used back them.
Then recently I had a fun time reminiscing with my nephew who has been with many women. I mentioned this and he said OMG uncle, I feel as you but have had a couple of black partners who gladly shaved. They understand this, all you had to do was ask!
So from serious relationship situations to particular sex acts. My most recurring thought is the composite image i create in.my head of all the women I’ve known. Oh well, you can’t have it all.

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I kinda wish I would just say yes to this person that has been asking me out for about 4 yrs but I can’t get over the fact it might be a one off or difficult relationship. Overthinking holding me back

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I had a dry spell in my early 20’s. I had always been a little bit bicurious, but hadn’t really explored it. To cut a long story short, I made friends with a guy, there was no sexual intent, but after about 6 months of chatting, things turned sexual and we watched each other masturbate on webcam.

We did that a few times, and then decided to meet up and try it out for real. It was awkward at first, mostly because neither of us had ever tried anything with another guy and wanted it to stay as private as possible.

We met up 6 times in total. Always at his house when his parents were out. We gave each other blowjobs and fingered each other.

My regret comes from the last time that we met up.
We were doing our usual thing and he said “oh man, I kind of want to do more.” By this point I knew I at least wanted to try receiving anal, even if there was no romantic attraction. At the same time, I was scared about people finding out that I’d done some ‘gay’ stuff because I couldn’t really see myself wanting to date a man. I ended up cumming not long after and post nut clarity meant that any desire I had to bottom was gone.

When I talked to him a few days after, wanting to plan another meet up, he told me that his cousin had read through some of our messages and because I was in his phone under a pseudonym, he was able to convince him that I was a girl. But now he was scared of being found out. Like me, he didn’t see himself wanting to date men, just experimenting, having fun and giving it a try. And even though he enjoyed it, he didn’t want to see rumours of him being gay at his all boy catholic school.

I never tried anything with a guy again. I did try, but never met anyone that I felt comfortable with. I figured out that it wasn’t guys that I liked, but I was interested in their cock. To this day I still wish I would have had gone that extra step and let him fuck me. Given where my life is right now, I don’t think it’s something I’ll have the chance to do again, and even though I still don’t find myself romantically attracted to men, it’s something I would have liked to have experienced, just so I knew if I liked it or not.