Whats your biggest regret from a lost oppertunity

[Ray Roberts]

No Regrets

I have absolutely no regrets about joining literotica, oggling Vanessa's pictures - a real sex goddess in amateur pictures and posting this thread.

Great to read I am not the only one to have missed out earlier in life

 

[Eiselmann]

Lots of what if's but the biggest what if was the first, I was 16 she was 14 , we got very close to each other during that year , even now after almost 30 years I still cherish the time I spent with her.

Circumstances meant that the following year I moved to a different part of my country and since her parents were very religious I didn't have the courage to try to build a long distance relationship with her, thinking her parents would freak.(I found out later that infact her parents totally approved of me)

Then when I was 28 I was holidaying in England and suddenly realised that she was the one, I tried to find her or any of her family to no avail then when I was 34 I started working for a company that she had once been a client of ...during that whole time I was looking for her she actually lived half a mile from my father.

I also found out that she got married about a month after I gave up seriously looking for her.

Then to top it off earlier this year I looked her up on my current employers customer base ....she was there , she hadn't been in previous searches....she had since divorced and had lived for over a year in a house not 2 minutes drive from mine , but had moved the week before I looked her up.

No idea where she is now. So my big regret is not having the balls to keep in contact even when I knew I had a good thing going....but I get the feeling shes been taunting me ever since

 

[KZHF]

Ahhh, one of my biggest regrets...

When I was about 21 years old, I was working at a hospital. I worked evening shift, and several times a week when everyone got off work, we would head to a local pub for a few beers. We would leave our cars parked in the parking garage and walk a few blocks to the bar.
I had a major crush on someone that worked there, too. He was much older than me, which added to the attraction. He was close to 20 years older, a quiet man who loved his sailboat more than anything. Back then, I didn't even realize what was going on, and now in hindsight, I wish there could be a chance for a do-over! He had a very powerful air about him. His eyes were intense, and made me feel like he could see right through me.
I flirted with him, but he always made me feel like I was just a pesky, flighty little girl. Until the one night when we all went out after work.
It was a small group of people, and the cold beers flowed easily that night. He sat next to me, and at one point, I put my hand on his scrub covered thigh. He leaned in to me and whispered, "You better be careful, little girl. I'm not wearing any underwear." Shocked, I looked up at him, and immediately pulled my hand away. Not realizing that this was the opposite of what he really wanted.
The night went on, more beers consumed, until closing time. The crowd thinned, and the 4 remaining people walked to an all night diner a few more blocks down the road. He walked and flirted with me the whole way there, and I (like the stupid girl that I was) didn't pick up on his signals.
After having a little snack, we lost one more of our group, just leaving myself, him, and my friend, who was an older woman that I worked with. She had always given me advice, and I usually listened.
She said to me, "He wants to take you home tonight."
I was terrified, excited, and shocked. I told her I couldn't because I was having my period! She said, "SO what! He won't care! He wants you!"
I couldn't believe my ears.
When we arrived back at the parking garage, my friend got in her car and left, and he walked me to mine. We stood there talking, flirting, and he leaned in to kiss me. His forcefulness, and masculinity was paralyzing. I was so completely out of my element, and under his influence. He told me he wanted to take me back to his boat, and fuck me like I've never been fucked before. He wanted to show me how a MAN makes love, instead of the "boys" that I was used to. My body was screaming, "YES, yes, yes!" But my brain was saying, "NO! You are having your period! That's just nasty, he will be disgusted!"
So, instead of telling him my fears, I told him, No, I couldn't come home with him. We both left frustrated, and unfulfilled.
The opportunity never came along again, and I have been filled with regret for years. Only now, that I have come to learn more about my own sexuality, and my desire to be with a more Dominant man, have I realized that he would have most likely been the one to introduce me to that lifestyle. There was just something about him that I will never forget, which leaves me wondering, what if...

OMG that is so incredible AnitaMann, thanks for sharing!

 

[JessC]

... but had moved the week before I looked her up.

No idea where she is now. So my big regret is not having the balls to keep in contact even when I knew I had a good thing going....but I get the feeling shes been taunting me ever since

This is a serious case of hire a private investigator and NOW!

Do not let another day go by not knowing what might be when a simple $100-$500 could find her in no time.

 

[Ray Roberts]

I'll continue to bump this along

I had a real young lads crush on my first girlfriend who was Swedish and a typical liberated drop dead looking Swedish miss. She was in England as an Nanny before starting Uni. We met at a holiday beach where her Doctor family were spending the summer. We basically fucked like rabbits at every opportunity and continued to see each other on and off for two years. I was extremely jealous at that time and hated being apart from her after about a year she informed me she was pregnant, I was over the moon but she said she couldn't possibly have a child while only half way through her studies. I ended up going to stay with her family in Sweden and wanting to get her to change her mind. While there a cousin turned up and she seemed to me to be giving him too much of her time. We argued continually and things went from bad to worse. After three weeks I returned home. That really was the end of the relationship, we did meet again but it was clear we would never be as close as those first few months and the abortion was always a negative subject hanging over our relationship.

Basically I screwed up I was imature and not able to think about her feelings only my own and that was the reason that split us apart. Pity she was a bombshell in the sack with no inhibitions and a figure to make heads turn. Plus we got on enjoyed ourselves and I sure could have made a go off it however I'll never know, I often wonder what happened to her and if she has children, she would be approaching 60 now and I bet she would still be turning heads!

 

[debycha1968]

2 co workers

I had 2 co workers,( one of which i was sleeping with) ask me if i was into a 3some with them. I laughed it off as a joke and never pursued it and now to this day I still wonder if it was a serious proposition.

 

[hotbodymale]

I had a girl who used to come over and write songs with me. Real small with D cup breasts. Sometimes she would play with her tits in front of me, but we never fucked. We had a working relationship that we thought could get weird if we did. I would have loved to have came all over her perfect tits.

 

[girlowned]

i was stationed in Okinawa Japan and went sight seeing with a male friend one day. He was the type of friend that was more when the mood hit either of us. Anyway, we ended up at this really cool Ferris Wheel. The "seats" were enclosed with a very strong plastic looking material; the bottom was red and the top and doors were clear.

Anyway, he asked me before getting in if i wanted to fool around when we went for our ride. i very foolishly laughed and said no. While he did it in a joking manner, i have no doubt he would have done it had i been game. i just didn't believe we could really do anything by the time it went full circle. About 1/2 way through (After i stopped ooohhhh-ing and aaaahhhh-ing...lol) i realized just how slow this wheel was going, i was kicking myself for not agreeing.

Now that could have been my most memorable public experience. *shakes her head at her own stupidity* i'll not make that mistake again.

 

[AutoDelux]

i regret spelling thread titles wrong.

 

[kodos9000]

I was 17 and I was very, very drunk as was my friends sister, I couldn't drive and we were a short distance from their house she told me to come to their place a sober up. I did what she asked and when we were there she began to flirt with me, only I was either to drunk to notice or to stupid, anyway I missed my chance. She thought I had no interest in her.

When I heard this from her a number of years later, that she had wanted me so badly, and I did nothing about it. Well lets just say I spent many a night crying myself to sleep! lol

 

[duke1421115]

Can the OP please correct the spelling of the thread title? Now?
Spelling annoyance aside...

I regret not taking my friend's girlfriend up on her offer.

She was in the same year as me at sixth form and was dating my best friend. We got on well, and I rather fancied her; she was strikingly attractive, tall, full-breasted and curvaceous, with a pretty, smiling face. I discovered (from both of them) that the couple had a wild sex life, both having been virgins when they had started going out, quickly moving through handjobs, oral, titjobs, and then sex within a month (anal too, as it happens).
A few times they said, "Why don't you join in?" They both knew about my sexual likes; I was still a virgin, though I'd had girlfriends, but they had found out about my breast obsession, and this girl said with a laugh that I could "shotgun" her breasts. She made a good many comments about indulging my titfuck fantasies... and about how she enjoyed double penetration.
I turned them down. One of my great mental blocks is cheating - I could never dream of cheating on a girlfriend and similarly I wouldn't countenance doing anything that could be considered in the same light and might harm their relationship. I didn't want to be part of something damaging to two good friends.
Later - a couple of years later, after they had broken up, I discovered that they had indulged in threesomes with other mutual friends and enjoyed them greatly. And that the girlfriend really fancied me as well. They really were well up for it, and my fears about harming their relationship were just my neuroses.

I'm still kicking myself for that one. I told my current girlfriend about it, and she said "Why didn't you?" Bloody stupid me.

 

[Ilovemymilf]

Cougar Regret

Unfortunately, too many sexual regrets to discuss in one place but my biggest regret happened when I was 18. Went to a senior party being hosted by an early 40's couple with no kids, (they were friends of one of my classmates and had a pool). Party was great and the wife was a very attractive 40ish woman who I had casually and innocently chatted with throughout the night. I went to tell her goodbye and thanks for the party and met her coming through the garage, just me and her and as I went to hug her she planted a full out french kiss on this young inexperienced 18 y/o. Damn, I wanted to lose my virginity right there and then but all I could think about was the husband walking in at any moment. She gave me the look that I now know means "let's get it on" just as my buddies walked in and said we had to go and like a fool I went with them. Looking back, I should have told them to eff off and gotten my education right in that garage. If only I had had some balls I could have had a COUGAR before Cougars were cool!!!! What a dumbass!!!!

 

[hardforit]

Mine has to be being dumb enough to resist my 18 year old niece when she was coming on to me (I'm 35). We were shopping with my wife and my wife's sister, and I was left alone with our niece when they went for some beauty treatment. She dragged me into a shop to look at underwear and kept asking my advice what she would look sexiest in. She even told me she was into older guys and not boys. She bought the ones I recommended and that evening when we were all back home she even whispered in my ear that she was wearing them. My God why didn't I just give her what she wanted? Now I can't get her out of my mind

 

[lorddragonwolf]

the first is with a woman i had known on a professional level for a few years she was a customer where i worked. she was hot and i had a crush on her. when i left there and went to another company she had come in one day and was hitting on me i was in a bad mood and was blowing it off. when i realized what was up it was to late next time i saw her she was with anther guy.


the second was with a manager at a pizza joint i worked at i should have fucked her but was scared her husband would have found out. if only i knew better at that time that she cheated on him i would have gone for it.