Biggest Sexual Regret?

[Ssbbw4u1974]

What has been your biggest regret sexually?

 

[Ssbbw4u1974]

I got drunk one night with my BIL.
I was separated from my husband, and thought I'd seduce the brother. I wasn't attracted to him, I was just drunk.
I didn't want sex...I just wanted to give him a BJ, so... It happened.

A few weeks later, I got drunk again, and called my ex husband, laughing about a secret I had.
I finally told him, and he did not think it was funny.
Then I kept getting nasty texts and calls from his family after that...

Big regret!

 

[Saint_Ann]

I got drunk one night with my BIL.
I was separated from my husband, and thought I'd seduce the brother. I wasn't attracted to him, I was just drunk.
I didn't want sex...I just wanted to give him a BJ, so... It happened.

A few weeks later, I got drunk again, and called my ex husband, laughing about a secret I had.
I finally told him, and he did not think it was funny.
Then I kept getting nasty texts and calls from his family after that...

Big regret!

Brotherfucker.

 

[Rockymtnman]

Lost a good friend by fucking his ex. They had been broken up for over a year but it still hurt him.

 

[PFWilly]

My biggest regret was a result of our first time trying marijuana with a good friend. Made me very sleepy, made my wife and our friend very horny. I went to bed to sleep, they didn’t. lol

They had sex six times that night. It would have been better if I’d stayed awake to participate, or at the very least, watch. Dammit.

Would have loved to watch them fuck four times, and to see her suck him dry twice. But oh no, I had to fall asleep!

 

[Not Normal]

Sexually, it goes back to not knowing how to flirt, notice I was being flirted with, and knowing how to 'close the deal.'

 

[Bdm20]

I regret not having more experiences in my youth. Had a long term girlfriend in high school, and then my first wife. Should have taken the advice of grandpa in the movie “Little Miss Sunshine”

Oh, and when my first wife wanted to try anal, and then enjoyed it immensely on all fours with my cock in her ass and a vibrator in her pussy and I whispered into her ear “too bad you can’t have a second cock inside you” and she said “Never say never”, I should have taken the opportunity to open our marriage.

 

[WhiteTailDarkTip]

Losing a large chunk of my libido (“being unchained from the madman” Socrates said - reputedly) led me to understand a few things; principally that my wife has been having sex out of some motivation I don’t understand. Duty? Avoidance of conflict? Keeping the show on the road? Whatever, the subject is very firmly not up for discussion.
So I now rather regret not taking up the offers that have been made over the years.
Hindsight is a hell of a thing.

 

[crem]

Not losing my virginity to my sister.

 

[Sgts19]

Not fucking the girl I used to workout with.
Something must have been wrong with me back then, she asked me twice once in her house while her husband was working

 

[Tweedledude]

Being much more open and honest with pre martital sexual discussions.
Both with partners but particularly with self.

 

[BillTheKatt90]

I regret my lousy judgment about what to do with sexual opportunities from my youth.

(1) I had a girlfriend who was waaaaay more into me than I was into her. I'm certain she'd have given up her backdoor for me, if I just asked for it. I broke up with her instead due to my own lack of interest in the relationship. The next girlfriend is my wife, who has an "exit only" policy, so I didn't know that would be my last opportunity. [On the other hand, had I followed-through, this entry would probably about how I used that ex-girlfriend simply to get anal sex out of her.]

(2) I had a very close friend in high school--one of a very close-knit cadre of best friends. He dated a very hot girl his entire senior year. They talked about being together forever and even went off to the same college after high school... where she broke up with him a few weeks into the first semester. Later that school year, she and I hooked up a few times. My close friend found out and hasn't spoken to me since. It's been 33 years. I miss his friendship.

 

[hotcpu]

1. Not staying with my first gf in high school who was in hindsight such a hottie from Cali

2. Not taking better advantage of a FWB who was and still is the best fuck ever!

 

[mark_j]

Probably the first GF I had after I turned in my V-card..

What a train wreck.

Her family was a nightmare, she was batshit and to be totally honest I was just using her.. Fun while it lasted then it all went off the rails.. Yeah, not proud of that one..

 

[Britva415]

What has been your biggest regret sexually?

Not asking for an open marriage a lot sooner.

Also, turning down several women who threw themselves at me because they were seeing someone else already.

 

[Lady2020]

Having an ol relationship with someone who was too young, a virgin, and in the middle of an arranged marriage. I didn't know any of that til the end.

 

[screwher]

Not asking for an open marriage a lot sooner.

Years ago we had the opportunity to turn our relationship into the hotwife lifestyle we enjoy now. If I had acted on it then, my wife could’ve been having sex with other men for all those years.

 

[Mostlyherefortheporn]

In college, participated in a foursome (ffmm). One of the girls was pretty wild, other was mostly conservative. We went on a couples date then went back to one of the girl’ homes and went wild. Conservative girl required some encouragement to get into it and didn't really understand what she was getting into. She was extremely attractive with a very busty, very curvy figure, so all three of us paid her extra attention & she got dp’ed a few times & ate out by the other women. Very fun evening, but the topic came up years later and I found out she regretted the evening. She didn’t feel like she was coerced, but it was a lot more than she expected.

Truthfully, I regret most of my kinky college exploits.

 

[easyoff]

That it took me so long to figure out that so many of my friends were bi and willing to play.

 

[Hitchiker69]

I regret that I didn't take advantage of opportunities for gay sex that I found when I lived in a foreign city. I was single, in my 20's, had some gay experiences before I landed in a very gay friendly town, where no one knew me. I lived within 2 blocks of two gay bars and a gay cruise park. It was just assumed that a single guy living in that neighborhood was, if not gay, at least Bi

I could have had gay sex a few times a week, but I guess I just wasn't ready for all that. I did enjoy 6 or 8 guys's cocks, sucking, fucking and all that

 

[LeeKee]

long ago while at the salad bar, a beautiful young black woman approached me and asked a few questions on behalf of her friend who was shy. We talked and arranged to meet later that week at a club. I met her shy friend and she was also gorgeous. We all were dancing and having a great time. The friend dances with me one country song and admitted the was helping her shy friend but decided she wanted me for herself. Wow. They both wanted to see me to my apartment and it seemed they either wanted to have a 3sum or decide who would go upstairs. It seemed like their friendship was on the line so I said good night. I regretted that I didn't just ask then both up ever since. Missed out.

 

[Snowbunny020]

Falling for the wrong guy … again and again

 

[Hitchiker69]

That it took me so long to figure out that so many of my friends were bi and willing to play.

Same here. I had no idea that 3 or 4 guy friends would have loved to have a suck and fuck session with me, until I was told after it was too late

 

[AndersonsBiographer]

Sticking my dick in crazy. One teacher I dated ultimately got back on the crack pipe and drove her car into a river one night.

Most of my relationships with other teachers have ended badly. It's a big part of why I'm pretty much celibate these days.

 

[ALovelyNudist]

Maybe just when I’ve been in relationships with men and women who clearly weren’t the right ones but fortunately they didn’t last too long