Whats your biggest regret from a lost oppertunity

[Ray Roberts]

Whats your biggest regret from a lost opportunity?

This makes me cringe every time I think about it but I missed out big time on an offer I should have lapped up and didn’t.

I was about 30 married with two small kids and lived in a small town of 7,000 people I was also a keen golfer and had a very good friend who I played with regularly he was nearing 50 but retired early to our holiday town he had a stepdaughter who was 22 who lived in London and was a real city girl always fashionably dressed sophisticated and way out of my league, actually I never really fancied her because she always wore too much make-up and I liked the sweet country girl look. Anyway we were all at a party, she was on a home visit to see her parents, and her parents were at the party as well as my wife. We did have one slow smooch together which I quickly moved on from always aware that my wife was extremely jealous type. We all partied around and were having a great time when my wife came up to me and asked if I would do her a favour, City Girl apparently was feeling unwell and she asked me if I wouldn’t mind taking her home as her parents had had to much to drink and also didn’t want to leave just yet. Sure I said in all innocence. We arrived at her parents large house after few words were spoken and she invited me to help her inside and then in for a coffee. Once inside in the kitchen, she excused herself and said please make the coffee. The next thing I see is the door opening and she walks in stark nude in high heels, my mouth must have gapped open at the sight as I stood there like a rabbit caught in the headlights. She had the figure of a model and such a sexy walk as she sidled over grasping my shoulder and saying "now then lover boy we will see how good you are at taking care of me" My head was spinning I was so naive then and pushed her away with all sorts of excuses. Talk about a woman scorned the next thing she was shouting and raving at me and throwing crockery as it crashed against the wall and I did a bunk. She stood in the doorway still nude shouting abuse as I drove away and back to the party. I later found out my wife had been talking intimately about our sex life to her mother and she must have passed this on to daughter. And yes I made a cardinal sin of blurting everything out to my wife the next day. The two girls ended up having a slanging match in the street and things were never the same again. We divorced five years later, and now with years of experience behind me I always wish I had taken advantage of what was on offer. The image of her standing there in her high heels is permanently stored, silly silly boy that I was then.

 

[youngrabbit]

When I was 19 I had been going out with this girl about 3 months. She lived with her mum who around the same time started seeing a guy. We all got on pretty well, he was about 45. My Girlfriend used to work in a pub and sometimes me her mum and her boyfriend would drink in there till it closed and wait for my gf and walk home together.

One night we'd had a few to drink and her mum asked if the 3 of us (me her and her bf) could leave early for a 3some. At the time I totally freaked out and never did it. Now when I look back I really wish I had. It always gets me horny when i think about it.

 

[Ray Roberts]

Surprised there are not more posts to this thread as I suspect heaps of guys did not take all that was on offer. Trouble is when you get wiser not all the same chances crop up. Bugger it.

 

[badbeth]

I had a chance to fuck my female gym teacher and didn't.

I had a chance to fuck my husband's cousin Wendy once and didn't.

I had a chance to be a porno queen once and walked away.

 

[shhibby]

innocence...

biggets regret:

not having sex with my first gf.. cause i was too in love and 'respected' her..i was only 18..but in retrospect..i wonder if that was the reason we ended..lol

 

[Berno_85]

my only regret is not talking a friend of mine who was just as much into me as i was her. we been flirting back and forth on a band trip and we were both so horny i had a chance to drag her to the bathroom at school and fuck her brains out. now i look back and regret i didnt stupid 17 yr old. she moved to az with her son she had from a exfriend of mine. i am still in love with her.

 

[SophieUK]

my only regret is not talking a friend of mine who was just as much into me as i was her. we been flirting back and forth on a band trip and we were both so horny i had a chance to drag her to the bathroom at school and fuck her brains out. now i look back and regret i didnt stupid 17 yr old. she moved to az with her son she had from a exfriend of mine. i am still in love with her.

OMG that's actually quite hot!

 

[Ray Roberts]

Mrs Prude

Another regret and this is a biggy because it's ongoing is that I married a wonderful younger asian girl and she was always up for sex, I always felt good when other guys were moaning about the amount of sex they received from their partners, knowing that I could initiate sex at any time without fear of rejection. Now after 30 years together and over the past 5 years she has gradually joined the old wives club of limiting our sex together. Bugger it I wish now I had filled my boots while the going was hot! Still love her to bits but her prudish attitude to anything remotely to do with sex is a big turn off.

 

[Malerik]

When I was a freshman in high school, one of my older brother's friends started hanging out with me. She was a senior, skinny and built like a supermodel. Eventually we started to flirt and ended up going out. She was the first girl to let me see her topless. Gorgeous tits, small but beautifully shaped. I had fun with her, but we ended up calling it off because of one thing: She was black and I was white. I had no problem with this, but I lived in a small midwest town and my friends weren't as open to the idea as I was. I felt pressured by them to let her go, and I caved. We stayed friends, but nothing further. I always regretted that I caved to my ignorant friends pressuring and wish things could have gone further.

 

[SophieUK]

When I was a freshman in high school, one of my older brother's friends started hanging out with me. She was a senior, skinny and built like a supermodel. Eventually we started to flirt and ended up going out. She was the first girl to let me see her topless. Gorgeous tits, small but beautifully shaped. I had fun with her, but we ended up calling it off because of one thing: She was black and I was white. I had no problem with this, but I lived in a small midwest town and my friends weren't as open to the idea as I was. I felt pressured by them to let her go, and I caved. We stayed friends, but nothing further. I always regretted that I caved to my ignorant friends pressuring and wish things could have gone further.

That's such a shame... lesson leanred I hope?

 

[Malerik]

That's such a shame... lesson leanred I hope?

Yes, indeed it was.

 

[EnglishRoseFox]

I would rather regret what I have done than miss out on something I didn't take a chance on. Sometimes it gets ugly....but if you don't try you don't know do you?

 

[MGs_Minion]

Ya, I always say you live once. So dont ask your self "I wonder If?"

 

[rocketeer50]

Twice

The first time was when I was 18 and had only had sex one time to that point. Went with my famiily to visit extended family two states away. My 15 year old cousin was bored and we hung out together for a couple of days. She came to my bed in the middle of the night but I shooed her away because of too many open bedroom doors in the house and I didn't want to get caught. I was too shy and scared to buy condoms in their small town, probably had to get the druggist to pull them out from behind the counter. A day or two later, cuz had me in the finished attic rooms and we stripped to our underwear. I was to scared of getting her pregnant so we just rubbed until I came on her belly. I was right to avoid the deed since she turned up preggers two years later.

Second time was in grad school. My steady girlfriend took a summer job in another city. One of my old college friends gave my number to a woman friend who was in my town on business. I took her out to dinner, then to a music club where we groped each other for awhile. It was clear I would spend the night in her hotel room if I wanted to. But I wanted to stay faithful to my girlfriend and I wanted to see if I could walk away from good thing. Sure enough, when I walked her back to her hotel and she asked me up, I declined.

I've regretted it ever since. Never turn down no strings attached, can't get caught sex with someone who turns you on and is willing. Life is too short. (But wear protection, especially if your horny teenaged cousin wants to bang you.)

 

[Ray Roberts]

everyone happy!

Seems by the few responses to this post that most people are pretty good at taking up those chances when offered!

 

[openminded_boca]

I had a very pretty co-worker that wanted to date me but the problem was she is 13 yrs younger then me.

I was 31 and she was 18.

I regretted it for a long time but when we caught up about 10 yrs later I found out she had a kid with the guy she dated after I said no. I guess she wanted to be a mommy fast...

 

[JessC]

The coffee club

It was a college union. I was back in school when I was in my early thirties and having a wonderful time. I happened upon a group of people that would sit in the smoking section of the union and drink coffee during break. Yes, this was a few years ago before all the colleges banned smoking.

The group was a mix of many types of people from the goth chick on Prozac, the very intelligent rebel, to the little hippy chick blond. It was an interesting group to hang around with and we had many exotic and surprising conversations. All in all one of the happier times in my life.

The little hippy chic was only 19 about 5'1' and maybe a hundred pounds soaking wet. She wore tank top t-shirts, tie-dye, jeans with frayed ends and leather patches. You could look at here and smell the patchouli before you got close enough to actually sense it. Her blond hair framed her face in such a way as to both hide her slightly yet accentuate her beauty. Her face was that of a wide eyed pixie and the color of her eyes should make the sky weep with envy.

One day one of the more socially inept members of our group was asking me how to talk to women, how to get a date. I asked him if he would like an example of how to meet a woman and he said sure. I walked up to the table that our hippy chic was sitting at and let her know that I was trying to help our friend become more comfortable asking women out and would she care to help.

She said yes so I squared my shoulders and took her small hand into mine and proceeded to say, "I couldn't help but notice you as soon as I walked in here."

I looked directly into those bright blue eyes and continued, "I was wondering if you might care to get a cup of coffee with me so that I can find out if you are as beautiful on the inside as you are on the outside?"

I noticed a hunger in her eyes and her voice came out in a low, sultry rasp. The kind you hear right in the middle of love making or maybe as you just enter a woman and a cry escapes from her without her will. "YES," She said.

I knew what had just happened but I second guessed myself. I was married at the time and while the marriage was anything but good I was going to remain faithful. I turned to our socially inept friend (yes, he was still there watching all of this transpire) and said,"See, it's easy to talk to any woman you want."

I saw a bit of confusion in her eyes until she remembered that this was something to help out our friend. Everything went back to normal after that.

It wasn't until about a year later, after my divorce, when a mutual friend of ours told me that she had been ready to fuck me that instant. She knew I was married and didn't care. I saw that in her eyes, I felt it from her voice but I did nothing. Sometimes I wonder if she still remembers that day. We lost touch shortly after my divorce and she had a boyfriend by then. I guess I will never know.

 

[Italian_and_Bi]

I used to think on things, say "had i done xyz differently..." but i dont bother with that anymore. its not worth it. that is living in the past, and i dont do that anymore. besides, something better is always just around the corner...

 

[littlebabyclit]

Whenever I regret anything, I usually wind up regretting that I had the regret at all.

And eventually, I realized, all my experiences have taught me something. Even if the lesson was painful I still think...so, what's to regret?

The only thing worth regretting is that some lessons are not learned without a painful lesson.

This is an interesting thread, I hope it continues. Not that I should hope people have a pile of regrets for my entertainment.

 

[JessC]

...so, what's to regret?

I can understand that. I don't regret the fact that I stayed faithful as that is a point of honor for me and just how I am built. The whole situation was something that I play over in my mind sometimes(rarely) and it actually gives me a little boost remembering how such a beautiful young girl wanted me.

It is just one of those memories that makes me sigh sometimes and ask "what if?"

 

[CowBoy18^]

Missing out on an opportunity with a friend whom wanted more, yet I was too stupid to realize it until it was too late and she got married. She really was one of those one in a billion women. I'll never forgive myself.

 

[littlebabyclit]

I can understand that. I don't regret the fact that I stayed faithful as that is a point of honor for me and just how I am built. The whole situation was something that I play over in my mind sometimes(rarely) and it actually gives me a little boost remembering how such a beautiful young girl wanted me.

It is just one of those memories that makes me sigh sometimes and ask "what if?"

I have many "what if" memories similar to that, being a long time married person myself.

In regards to what I posted above, I could be full of shit, too. Maybe I tell myself all I wrote to keep the pain of regret away. Oh well, it works.

There are some things I still do regret, they involved my own ignorance, stupidity or head-up-my-ass-itis. But what the fuck can I do about it now?

'Tis better, for sanity's sake methinks, to take the philosophical approach to one's own fuckups in life, including
so-called missed opportunities as well.

(This ambivalence brought to you by a fully Libran personality whose scales swing up and down on either side of an issue.)

 

[goodgurlgetsbad]

Not taking the chance to tell somebody special how I felt about him because I believed a lady shouldn't do that - then 3 months into my marriage- like we always did- we had a heart to heart talk and he revealed he cared so much, he thought I knew how he felt, he wanted to get his dream job before courting me, he is still single, no girlfriend and we still talk, sometimes I cry over missing chances, my lost love , sigh ***

 

[AnitaMann]

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...

 

[ima6uldv8]

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...

Damn. Doesn't it suck about being so young and naïve? I think age is the deciding factor here. We're older and oh so much wiser. That night would probably have been a scorcher. I know you must kick yourself about it.