Researchers from the University of California-Los Angeles and the University of Texas surveyed 25,000 people about their sex lives and found that men regret missed sexual opportunities more than women. Quotes:

"Most men spend their lives regretting not making a move on people they found attractive. Women, however, more frequently regretted picking the wrong person as a sexual partner.

"The results suggest that regret is an important part of modifying and improving future relations between the sexes. They found the top three regrets among men tended to focus on missed opportunities.

"A full 27% of men quizzed regretted being too shy to make a move on a potential sex partner; the two other most common regrets were not being sexually adventurous enough when young (23%) or single (19%).

"Women's top regrets were losing their virginity to the wrong person (24%), cheating on a partner (23%) or moving too fast sexually (20%). Women were also more likely (17%) than men (10%) to regret having sex with an unattractive partner."​

What is your biggest regret regarding a missed sexual opportunity? Mine was not moving on my sister-in-law when the opportunity presented itself: she was visiting us trying to get away from a bitter divorce. The two of us were alone at home one evening when my wife, heavily pregnant, was out attending a meeting of her reading club. My sister-in-law was dressed to kill, obviously displaying her sexy body. There was no doubt about her itentions when she steered our conversation to how she missed being with a man.... I simply did not have the courage to make a move on her..... and regretted it ever after, since she moved back a few days later.

 

Oh gods, I was a totally confused and repressed loser from puberty until somewhere around 30 yrs old. I missed more opportunities than I can possibly remember. Maybe one of the craziest was the day my girlfriend and I went to see her best friends new home that she and her new husband had just bought. Well the best friend and I had known each other a LONG time, she in fact is the one who introduced me to my girlfriend. The first time I was old enough to hit the bars for New Years, at midnite the tallest and most beautiful woman in the room singled me out and kissed me passionately then smiled and walked away. I asked my best friend..do you know who that was? He replied, of course, that's one of my step Dad Ray's three daughters LOL. I mean, this gal was so beautiful that when I would deliver her mail and she'd be sunbathing, I'd have to take my lunch break and go masturbate. Anyway, I am kind of a surprise, pretty damn good in bed and 7.5 inches which looks bigger on my 5'2" frame. And I know my girlfriend has been bragging about me to her "bestie". My girlfriend has already seen the house so she and the new husband , who have known each other awhile, sit down to coffee and to play cards while the best friend gives me a tour. The tour leads to the bedroom where she, to my stunned amazement, she starts unzipping her jeans all the way down, her golden pubes showing clearly she was wearing no undies, and then leans back against the dresser seductively and tells me she knows I have wanted her for a very long time and I can have her now. I moved in very close, whisper range, and told her she had no idea, and then told her about running home to masturbate after delivering her mail, thinking she MIGHT be offended but maybe not... She told me she wanted me to fuck her right then and there.. I looked over my shoulder at the door, just a few steps down the hall to the kitchen where our partners were playing cards, and said I couldn't betray my Girlfriend like that, or her husband. Truth was, I didn't know her husband at all.. but I did know he was at least 6'3" and 300 lbs and if we got caught he could kill me.
The real thing that makes me regret saying no is that this girl was unique, she had a very free spirit about sex, something I describe as a fairy spirit born into a human body. There was a real innocence to how naughty she was. And I bet her husband knew this, she had been married more than once before and was well known party girl. If I could live that moment again I would have whispered to her "You can have me your way this time, but only if you promise to come to my home soon and give me the time and privacy for me to have you my way." And then hope I wasn't too terrified to get it up and give her the naughty quicky she was looking for. LOL.

 

I worked at this op shop and every now and then this women would walk in and do her thing, and I got to know her so much that I wanted to bone her, so on my last day working at the shop I met her again we talked a bunch and then I left, so I walked over to the shopping center and met her again, I made a joke, she laughed and I said see you later and left for home, when she laughed I know now I should have made a move, I really regret now fucking her

 

I have quite a few.

I've missed out on a mother/daughter threesome. This was the mother:


I've passed up fucking a super hot cam model but choose the girl who became my wife. Model:

I once passed up a chance to fuck my sister's best friend. It was obvious to everyone that we wanted each other. People were taking bets on when we would and where. But I had a gf. No pic of her.

There's more but those are the very first ones that came to mind.

 

As a bisexual person, I've missed a few opportunities with men and women. One was with my friend's girlfriend in college. She was so hot and we had a few chances to fuck back then. I didn't execute them. She found me a few years back at a store and she hugged me and kissed me (latino culture thing). Again no move... I totally regret it!

In regards to sex with men, I once missed an opportunity with a family friend (older man). We were at his place by ourselves... I was dressed with tight clothes (practicing crossdressing) and he made a subtle move on me. He then fondled me and got naked and hugged me. I touched him back buy no sex... I regret it!

 

missed times hell yes.. i could even name the 4 girls i was a "gentlemen" 4 and didnt take the chance, of course at the time it was the right thing to do. looking back and kowing what i do now maybe i wouldn't be "the gentleman" and do the rght thing. while i still have stroke session remembering them, i dont regret being the "gentleman" and doing the right thing by them, none can say i wasnt just that .... btw their initials... S.F .. P.S.. J.S. and D.M.. as far as males are concerned., I have passed on several.. either becuase they were to impaired or i was i can only think of 2 off the top of my head i would like a sceond chance at all these years later...

 

Yeah, sounds like me. My regrets are things I didn't do, not things I did.

I don't think I ever missed an opportunity because I was too shy - that's just not me. But I can list at least a dozen specific opportunities I passed up because I was in a relationship with someone else. And I'm sure I missed a few more opportunities because I was clueless and just didn't get the fucking hint. Wow, that sums me up! Brash, loyal, and thick.

Oh, there was one opportunity I passed up because I wouldn't let her go down on me unless she let me reciprocate. How does a teenager pass up a blowjob?? That was stupid. I think that's the only one I'd change if I had a time machine. I wouldn't go back and cheat on any of my girlfriends; but if I could just appear in a flash of light, smack my younger self on the back of the head, and say "The fuck is wrong with you? Get your dick out, she wants to suck it!"

 

I passed on a few opportunities that I would love to have back.
The weird thing was that I was worried about MY reputation.
I didn't want chicks to think that I was just 'pervy'....
What an idiot I was!

 

Any if my daughter's friends they are all 18 now I had opportunities
But I'm a pervert not a pedofile
If the opportunity presents it's self again I'm there

 

When I was in the Navy I was stationed in Charleston, SC. My hometown was outside of Chicago.
My best navy friend lived in Cincinnati.
When driving home on leave, I'd drop him off at his house on my way and pick him up on the way back.
I became friends with his family. (parents, brother and two sisters)
One time I was travelling by myself and his family offered to let me sleep over at their house before heading on the next morning.
Because my friend wasn't with me, they offered me his bedroom.
I was awoken by one of his sister crawling into bed with me. "I couldn't sleep" was all she said.
Feeling awkward, I moved over to make room for her, draped my arm across her and tried not to think about how cute she was.
She started getting frisky and moving my hands to her intimate parts.
I hesitated and tried to explain that she was my best friend's sister and we were in his bed. (remember guy code? It use to be a thing.)
After a few more attempts she crawled out of bed and returned to her own room.
The next morning, she was the only one from the family who didn't come outside to see me off.

When I returned to duty on my ship, my friend confronted me. He said his sister was pissed at me and he wanted to know what happened.
Not wanting to tell him that his little sister crawled into bed with me and offered herself to me at the first opportunity, I feigned ignorance and told him I had no idea.
He came back with "She says you refused to fuck her." (not 'make love' or 'have sex with')
I tried to explain that I was trying to be chivalrous and not take advantage of the situation.
He said "Dude. She's fucked all of my and my brother's friends. She was on the pill before she had her driver's license.
You hurt her feelings. She thinks you don't think she's attractive"
What was I supposed to say? "Sorry. Next time we're in Cincinnati I promise I'll fuck your sister." ?

 

I knew it! I'm not getting laid because women always pick the wrong guy.

 

True

 

I have certainly had a few. Probably my biggest was once when I was with a close female friend and she asked me about the sorts of sexual things that I fantasizes about, to which I said anything and everything. Her mind went right toward anal and then she started going on about how uncomfortable it would be. I wish that I had told her that in my anal fantasy about her there would be no discomfort because she would be doing me wearing a strapon dildo. I don't know if she would have gone for it, but I will never know.

 

I regret that trying to suck cock at a earlier age.

 

probably 4 or 5 that really matter... I can be really stupid

 

Yeah, all the chances I didn't take.

 

A pretty sexy femboy was hitting on my girl and I and she was definitely the sexiest one I've ever seen in person. I acted disinterested because my friends kept looking at us funny for talking to her. You could see people talking shit but then you'd see them staring at her ass in that mini skirt. She was dancing with my girl And my dick was hard. She wanted to leave with us but I said no. We went home and fucked talking about her. I would have eaten that bitch's ass and I know damn well my friends would have too. Since then I mostly look at femboy and tranny porn. I can't believe I missed out on that opportunity.

 

Two summers ago I went with a gf to her apartment in Spain, for a short 4 day break. We got chatting to a group of four guys in their 30s, who were there to play golf and have a good time. As they were staying at the same complex, we'd see them at the pool after their day on the golf course.
We had drinks and dinner with them one evening and they made it very clear that we should go back to their apartment so we could be entertained fully.
I was very keen, but my gf talked me out of it. I could have killed her.