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Biggest Sexual Regret?

Second regret was a buddy of mine had another friend who needed help with his truck. So we went to help him out and after all day we had if fixed. My buddy said he would stay there for the night and invited me to stay as well. We talked and all the while they both were hinting I should shower and stay. The hints bounced of my head I guess, and they got more obvious they both wanted me to "shower up there, and stay". It didn't dawn on me fully until I was backing put the drive way, but I thought ,dang, I think I already was rude to leave. Looking back, maybe should had seen where it lead.
 
LeeKee said:
Second regret was a buddy of mine had another friend who needed help with his truck. So we went to help him out and after all day we had if fixed. My buddy said he would stay there for the night and invited me to stay as well. We talked and all the while they both were hinting I should shower and stay. The hints bounced of my head I guess, and they got more obvious they both wanted me to "shower up there, and stay". It didn't dawn on me fully until I was backing put the drive way, but I thought ,dang, I think I already was rude to leave. Looking back, maybe should had seen where it lead.
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Three guys in the shower? What a hot start to an all male 3some.
 
easyoff said:
It wasn't too late for me, we played after they were married.
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You're lucky. I would have loved to have my girlfriend watch me enjoy a cock. My wife has some gay friends who I would love to suck and fuck. Bonus points if she would watch. Double bonus points if she could be persuaded to eat pussy while I watch while enjoying a cock or 2
 
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There are things I wish I hadn’t done, and some I wish I had. My biggest regret is not coming to terms with my sexuality until to late to enjoy it. I was already married for many years before I admitted to myself that I’m bi. Way too many missed opportunities to explore what that meant to me.
 
Not knowing how to talk about sex with my girlfriend when I was in my late teens. I think she was ready to lose her virginity to me and I to her, just didn’t know how to discuss my issues with taking that step.
 
I wish I would have continued to have sex with my ex wife towards the very end of our divorce. She was very dishonest and manipulative, so I ceased all contact with her. She would call and text about fulfilling my wildest fantasies. Tempting me. I wish I would have given in. On a few occasions she called me to come over to reclaim her freshly used pussy. I wish I would have. I miss how slutty she was, but unfortunately she was not a good person.
 
That I missed the opportunity with my first boss. She found out I was a virgin and kept saying things like "you wouldn't even know what to do with a woman" and "you need someone to teach you a few things before you get a girlfriend" looking back, pretty sure she was hinting that she wanted to be that one, and was hinting at it fairly obviously, but I was embarrassed and oblivious
 
I was involved in a MFF threesome in which the girls didn’t play with one another. Therefore that fantasy remains unfulfilled.
 
First: not taking more advantage of a FWB relationship with a college girlfriend. In the end she turned out to be a freak; kinky, bi, and loving sex. We remain good friends but the could have, should have regrets are there.

Second being a totally shy dweeb. Not knowing or picking up on signals from woman or potential partners. Still am lame when it comes to it. I know I missed lots of opportunities to enjoy sex.
 
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My wife and I dated almost 8 years. During her first two college years, she had a lot of sex with others, but I was waiting until we were married. She even asked me to have sex with her, but I wouldn't do it. I regret that. I should have been fucking her all along before we married.
 
Something I did do, and something I didn't:

1. Regret getting involved with a woman who was, not to put too fine a point on it, a fucking lunatic. She wouldn't let it go when I ended the relationship and made my life hell for a couple of years. The sex was pretty good, though.

2. Regret not allowing myself to have more fun with sex in my youth. In particular, I remember a few mmf threesomes where the guy was obviously interested, but I couldn't bring myself to reciprocate. Wish I could make it up to them now.
 
HornyOlderStroker said:
Something I did do, and something I didn't:

1. Regret getting involved with a woman who was, not to put too fine a point on it, a fucking lunatic. She wouldn't let it go when I ended the relationship and made my life hell for a couple of years. The sex was pretty good, though.
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The crazy ones are the best in bed!
 
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