I have regrets of when I've passed up opportunities and turned women down over the years.  I thought this would make an interesting topic if you care to post regrets you might have too.

I will start.  

I was unhappily married and living next to a married hot blonde.  She called one night saying her husband was gone and her sump pump wouldn't turn off and could I come over and look at it?  I said, "sure".

She answered the door in her robe and I kept wondering about her being nude under it.  She had a thing for me and had made it well known to me.  After fixing the problem, she looked me in the eyes and says, "Do you want anything?  You can have anything you want".  

What I wanted to say was, "Yes, I want you to drop that robe on the floor".    But I didn't say it.  And I've thought about that moment several times a year for each of the over twenty years since it happened.  I really regret not speaking my mind

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I was in my mid 20's and single. Had a married friend whose husband was abusive but in jail at the time. She was a hot, tiny spinner. After a night of drinking I gave her a ride home and she invited me in. We chatted while warming by the fire and she was dropping hints left and right, but I was clueless. I still had not lost my v card at the time and did not know what the hell I was doing or not doing. I wish she would have been my first and I have relieved that moment many times over, but I am pretty sure something bad would have come from it (pregnancy, beat down by hubby, death)...lol.

I was 19, in college and living in a coed dorm. I had a janitor job cleaning two bathrooms in a girls wing of the dorm. I usually waited 'til 10pm or 11 each day to clean these, so as to NOT find them occupied.  

One night (my 19th birthday in fact), I was finishing up the last bathroom. I went back to my supply closet & got the mop & bucket to clean the floor. When I returned, a gal was there in a robe, 'watering' her plants (five) in the row of sinks. I knew her casually from mutual friends.  Friends had told me she was BSC. She was a couple yrs older than me, average build, big tits, long black hair, pale skin, and usually wore some red or pink lipstick. She had sort of a Goth look, like the TV personality 'Elvira'. She smiled and apologized for 'dirtying' the sinks. I laughed & told her I didn't mind, as my job was to clean them just once a day. I kept mopping, and she wished me a 'Happy Birthday'. I asked how she knew. She'd walked past my room earlier when I was having a party. She'd seen cards on my door, and a handful of friends having beer with me. I thanked her. She responded "I didn't get you anything..."  I turned from my mopping, & saw she was leaning back against the sinks, her robe half open, showing me her night gown. "Well, I wasn't really expecting gifts from anyone, so it's fine, really" I replied. She then said "you can have anything you want..."  

Now, I know you're thinking, "God, jump her!"

Well, a couple things held me back. First, two of my guy friends had dated her(and fucked her) a couple times and he thought she was just Bat Shit Crazy. Second, we had mutual friends, and if I did get even a BJ outta this, & if she tells just one mutual friend, it'll get back to my GF. And finally, my GF was waiting for me to finish my chores, so she could give me my birthday sex present, back at her room. I finished mopping and left.

in hindsight, I wish I'd at least gotten a BJ

She and I worked at the same company but in different departments. She would "eye me" in the lunch line down in the cafeteria. I wasn't clueless, but I certainly was shy. After all, I was married – so I did nothing to respond to her. That was Strike One.

Years later, she and I crossed paths closely at a company off-site. Some of my subordinate staffers were in attendance, and one of them was present with her and me at a restaurant when she had the fortitude to nudge me again. I would have taken her in a second – but my staffer noticed what she was doing and I had to visibly step away. That was Forced Strike Two.

A year passes. She and I meet at a company Christmas party. Her husband and my wife were both out of town that night. Finally we clicked. I suggested that we separately head off to my place and indulge in some Christmas cheer of our own. She smiled a smile that had been years in the making.

You can guess what happened later. And for the next two years we often met up secretly and had a wonderful time. We were helped by the fact that her husband had moved out.

My regret, of course, is that I had not acknowledged her earlier. Potentially, more years of good sex might have been enjoyed.

(If you want to know how it all ended, you'll have to post a request for the story.

I was in the DC area and single. One of my fraternity brothers girlfriend moved to the area and I showed her around town. After a wonderful afternoon, dinner and drinks, I took her home. At the door of her apartment, she surprised me with a pretty passionate kiss. I could tell from her eyes, that she wanted me to stay, but I couldn't do that to a brother.  

Anyway, they broke up soon after, but I'll never forget the desire in her eyes and the sparks that evening. She was French Canadian and smoking hot.

I was a college senior working on my senior thesis and had to travel a few hundred miles to another college campus to do some research there.  I went to the housing office in inquire about any overnight housing opportunities when a nice looking coed overheard me and said: "Why don't you come spend the night at my place?"  At first I thought it was all innocent and all and we walked along talking and getting to know each other when we passed a drug store and she said:  "I need to duck into this place and pick up something."  That something turned out to be a tube of contraceptive foam.

Now, I'm thinking this is getting interesting.

We end up at her place, and she shares this apartment with a few other girl friends.  We have some supper and keep chatting and finally she says it's getting late, good night.  She points out a room for me to stay in and that's it.  (Her roommate had one of the all time melt down phone calls with her mother going on all through this time, but that's another story.)

I sort of felt that I was living out that old Beatles song, Norwegian Wood:

For you youngins

A couple times. Best friends wife was hot and had thrown hints. The hints became less and less subtle until the evening that my wife was out of town and her husband, my best friend, was at work out of town. She called and invited me over. Wanted to, real bad. But I could not sign up for cheating on the wife and stabbing my buddy in the back. From time to time I think back on that and sort of wish....

The other time was about a year after this. The very day that my first child was born. It was almost at the end of visiting hours when a lady I had never seen before arrived at my wife's hospital room. The wife knew her, an old family friend. This woman was from France, about 50 years old, hot as hell and dressed to the nines. End of visiting hours we left for the parking deck and I walked her to her car. She gave me a nice-to-meet-you hug and then kind of held on as she asked me why didn't we go to her place and have something to eat. Me standing there ain't had sex in about six months Yeah, am I gonna be the guy that goes and gets laid while his wife just gave birth to my child? Nope. Sometimes being good sucks real bad.

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But morals say no. She is very attractive but her husband has been very ill for years. And is on his death bed  now. But I could never do it. Morals, and it is not good business.

a DFCK instead of the usual DFK?

an opportunity like the ones described here, and there were many, I would always try to quickly assess what the potential for blowback was, and go forward or pass on it depending on whether it was going to be worth the potential grief down the road.  Being a little analytical in these situations is probably why I'm still alive.

Every time I did, either the woman was married (one was separated from a SOB, but still married) or I was married, or both.  I decided when I got married I'd never have an affair. (Yes, I think p4p is a much different thing than having an affair.)  And I'd never do anything to break up another marriage.  So, no regrets.

Also, maybe she'll do a better job taking care of the poor fuck if you file her horns.

The best explanation that you'll find is probably here:

https://www.beatlesbible.com/songs/norwegian-wood-this-bird-has-flown/

Plenty of stories here alright. My very first one was also my chance at leaving virginity. It was my first year in the university and I answered an ad from a local doctor needing help with his files and records he kept at home. He was in his 50s and his wife in her late 40s maybe even early 50s.  

A few times I came to work in his residence he was at work in his clinic or hospital so I was alone at home with his wife. She never did hit on me but dressed very provocatively and kept making small talks. In spite of her age she was petite and had a nice slim body. I was semi-attracted to her but was just too timid. Hell at that time I never even had a girlfriend.  

Looking back it could have been Mrs. Robinson kind of thingy what with a lonely, bored housewife alone with a young, virile college student.

I also had a few other regrets in regarding to roomates. Eventually I got tired and wised up at the missed opportunities so I started screwing my roomates as well

most memorable was with a co-worker.  she was a hot, busty brunette. we were assigned to a 2 person project which meant late night at the office.  she let it be known that I could have her at any time. I was currently involved with someone ( who would eventually become my wife) felt that if I was going any further in the SO relationship, I had to keep Mr Willy in my pants

I was a virgin at the time, many years ago.  My best friend's (at the time) wife and I were good friends and often visited for  movies, meals, etc.    One night he went to sleep early and we watched a movie together.  Next thing I know we were lipped locked - passionate kissing.  We stopped and she asked if I wanted to go in the garage for privacy and I said no as I knew where it could go.  I slept on the couch and the next morning I left and we did not say anything.  During the drive home I had a feeling of regret for not saying yes.  I was bummed.

Anyways, a week later or so, he had to take a trip out of town unexpectedly.  She stayed behind to take care of the kids.  Needless to say, we had mind blowing sex for an entire week and I even slept over every night.  She made me want to comeback for more.  I think about that week from time-to-time.  I believed he (husband) thought something was suspicious and ended communication with me.  She would call or email me but I did not pursue as it was the right decision.  Funny thing, she showed up as a friend recommendation on Facebook and I removed it

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In high school I was dating this girl.  She invited me downstairs to her room.  Her parents were upstairs sleeping.  We had been into heavy petting but I had never had sex.  Got her pants off that night and she pulled me on top and said, "push".  As soon as I realized I was in her and we were about to fuck I lost it and came inside her.  We never got to fuck again.   I always regretted that I didn't perform better.  25 years later I looked her up.  I got a do over!  We fucked 3 or 4 times.  I thought that was pretty cool that she was my first and 25 years later I got to have her again a few times.  She was BSC though and it didn't last more than about a month and we broke it off.  She ended up being with a woman after that.

My boss was a very type-A woman, pretty but not really my type.   She had just gotten divorced, I was going through a divorce so there was no moral issue.   We ended up talking in her office after everybody else left, and she finally leaned back in her chair, stretched her boobs out and said "I'm feeling kind of whore-ish, and I bet you'd make a great date".   I have not always been quick to pick up clues, that there was NO doubt about what she was offering.  However, I knew it would be career suicide for me, so graciously made my exit.  Never regretted that one, because I also didn't want to be anybody's boy-toy.   She gold-dug her way to the top, broke up the CEO's marriage and they are now married and rich.  

My co-worker, also divorced, very pretty and petite. I was in the rocky marriage, but had not decided to divorce yet, so I still felt married.  She started coming in my office more and more often, I'd be sitting in my chair and she'd lean on my desk to chat, and next thing her thigh was pressed against my leg.   Then at the company Christmas party, I'm sitting at a bar stool and she walked up and pressed her crotch against my knee and said "let's get out of here".   This one I regret, found her on FB and she still looks good!  But it didn't feel right, me still being married.  

Finally the subordinate; this girl was honest to God crazy.   Me and my co-worker and her sat in the same cubicle; we're all working away, not talking and she announces loudly "I need a really good fuck".  My buddy and I didn't say a word, after a few minutes we met in the hall and had a WTF did you just hear that moment?    Again, career suicide, so no regrets.

I was indoctrinated in religion from early childhood, with a mother who was ashamed of her sexuality and her body (and considered a picture of a woman in a bikini to be pornography).  I  was taught that "proper" women don't want sex.  So, starting with my teenage years and ending with my mid-20s, I can name off the top of my head six different HOT women who I turned down.  And those are just the ones who I remember vividly, the actual list is a LOT longer.

Fuck religion.  It's pure fucking poison, and I wouldn't wish my experience on anyone.  Nor would I wish my BSC mother on anyone.

Not a single fucking thing. lol

My mother was the exact opposite of your mother, she never rammed religion down my throat, she was never judgmental about the women in my life, even when a brought an ex hooker home to visit who was 30 years younger than me a few years back. Come to think of it, my mother rocks and I wouldn't trade her for the world. I think I should call her to say so. lol

I do design work and frequently work with woman. All kinds of women, many who are drop dead gorgeous. Some not so. Tge hardest thing for me to ignore is the body language. I know they're flirting, some more so than others.  

One that comes to mind was a 30 something with great tits putting her hands behind her neck, bending back with her twin towers proudly pointing skyward and baring her tight mudriff. wtf

Since I'm not self employed, I need to be careful so I can stay employed. It's not fucking easy.  

Then there was a steamy 50 something woman who I hit it off with. I knew her sister during my married years. We clicked but she told me she was seeing someone. On our next design appt., she brought in her mother who was a sweetheart and a charmer, albeit old and a bit senile. She loved me and gave me a hug as they left.  

The next time I saw my client, I mentioned her mother and she stoid up and told me she wanted to give me a hug because I was so nice. We shared a very warm embrace as I hugged her back! I whispered in her ear that I could get very used to this and she smiled. When we disengaged lol I told her I'd like to see her over dinner. She thought for a moment, said she'd like to but wanted to give her new boyfriend a chance, but she'd leave the door open if it didn't work out. SLAM ... I guess it worked out ... next time I saw her she was as
cool as the other side of the pillow.  

Whatever ... rhis happens a lot and I understand women thinkthink they can get more outta business by also playing the sex card. I would and do too.  

Funny, when I was managing a design studio, I had two cute young women working for me. They both were flat chested. But whenevwr they saw a guy walk in alone, they would look over at me, unbutton their blouses a bit and go over to introduce themselves. They'd also lean over so the guy could look down their blouse but there wasn't  anything in there ... I used to sit back and laugh while watching the guy's reaction to the teasing  

...  now if it were AngelinaDDD ... that would be a different story ...  

my regret  is that I have to be more careful than I'd like to b

I met this girl "accidentally".  The college cafeteria was crowded and I saw one spot open at a table opposite a homely girl who was eating and reading.  I asked her if I could sit there to eat my lunch and she acquiesed.  As I ate my lunch she introduced herself as did I and we made small talk.  When I was about to get up and leave I mentioned that I had a 4 hour break until my next class and that I was going to hit a movie a few blocks away.  She askes if she could tag along.  I said sure, no problem.  Now I am naturally gregarious and the old Mystery Science Theatre 3000 gene is strong in me.  We saw this crappy movie with Jeremy Irons and an older famous actress I can't remember.  I cracked jokes at the screen throughout and thoroughly pissed off the upper East side NY audience around me, but this gal was entranced.  She started clinging to me (figuratively) like a leech.  She was in no way attractive to me but I am friends with lots of people.  She got my number from a friend and started calling me 2 - 3 times a week, if I was in the cafeteria with my real friends she would show off and try to get next to me and generally embarrassed herself by throwing herself at me and "defending" me from good natured jibes by my buddies.  She basically turned my entire group of friends against her and turned me off by her possessiveness especially since all we had in common was one "date" as "friends".  This went on for a month.  Finally, she snapped at a girl I WAS interested in and I had had enough.  I walked her outside and told her that it just wasn't going to work out, that we were just friends and really just acquaintences at that.  I had enough friends I told her and didnt have room for more in my circle and would she please stop hanging around.  Her face fell. "You are breaking up with me?  Is it because we havent had sex yet?  I would you know, anytime, even now?"  GOD as my witness that had been the farthest thing from my mind.  Since I had met her all I had been was annoyed by her, not turned on, nothing.  Thinking back though, she was 18 (I was 20), she was female, and obviously a sure thing.  She was a trim, if plain, mulatto chick with glasses and healed over acne.   I tried to be gentle and let her down by saying she was a smart and pretty girl and she shouldn't just throw herself at anyone that way.  She would find someone wjo meshed with her better, etc. Etc.

Looking back, I should have banged her.  Other than a Times Square peep girl and a few other providers (back then I called them prostitutes) I didnt get civvie laid for another 2 years.  Karma I guess.  She ran off crying and other than a few times in the hallways I nevr saw her again.

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Did anyone else here ever go to "band camp" and if you did, wouldn't you take that fact to your death?

I'd fuck her and not take that fact to my death.

that I was so naive that I probably passed up a whole lot of pussy without even realizing it.

I said I had other plans, but I didn’t want to do it on such a short notice. (What was I thinking?!)

Attached is a video clip ending of “2-lucky guys” on similar missed opportunity.


-- Modified on 7/4/2016 11:44:58 PM

I've been lucky enough or unlucky enough to have had a half dozen of these situations. The truth is that passing up on so many enticing situations and ladies is a big part of what got me on this board in the first place. I've been lucky in that looks and personality wise women have always liked me, but I never cheated on girlfriends and usually had one so here are the "REGRETS".

For some reason I've turned down some of the best looking women I've ever seen.
Here are a few descriptions that I've relived in my mind quite a few times:

1. She was 5 foot 10, dark haired, and in amazing shape and super eager at 22 years old.
A Ms. America contestant was trying and trying to get me to sleep with her when I was engaged. She ended up in the top 10 at the pageant. My friends were all over me to sleep with her and I had to listen to tons of 'what the hell is wrong with you' comments and half joking requests for me to get in a room with her, turn out the lights and then switch places with one of my friends so that they could be with her. I was 22 at the time and the truth is I knew she really liked me since she was a friend's sister, and I just didn't want to lead her on or cheat on my fiancé.
That being said, I have wondered how a weekend with such a sexy woman who wanted me would have been.
HIGHLIGHT QUOTE: She called me one morning when she was in town and asked me to stay home from work and come over to her place. I told her I couldn't and she said "I unlocked the door for you. I'm naked on my bed. I promise that if you come over you'll cum and cum and cum."
I did not go over.

2. She was incredibly sexy in a classy way, truly about as beautiful as a woman can be and smart and fun and really outwardly engaging with me:
I had a business convention a couple hours away and took a took a train to it. I saw her get on at the first stop and was honestly blown away. She wore a blue floppy skirt that was sort of the business version of a catholic school girl skirt only a little longer, her legs were long and toned perfect in white stockings, and she had a white blouse that looked ultra sexy on her. I mean of all the women I've ever seen anywhere in person or on tv she was top 5. She looked at me while she picked a seat and chose the one open in front of me even though many others were open. I checked her out about 20 times which she couldn't see since I was behind her and then she asked me where I was going in the city. I told her what convention I was going to and she energetically stood up, sat down next to me, and told me what she was doing at the convention that day. We had a real spark and obvious mutual attraction. We talked the entire train ride, shared a cab, and spent the whole day together at the convention with her business friends. Luckily for me I knew nobody there so the day continued with the lust building and I know it was in her too, because she asked me to dinner. At dinner she told me how she was training for the winter Olympics for ice skating and we talked about that and somewhere in there she said she was married. I think she was looking for a reaction, but I didn't give one. She asked if I was "available" and I told her a was dating someone, which was true. We had a great dinner with other business colleagues, but I never made a move even though she stayed at my side at the restaurant.

We then went to the station, rode the train back talking the whole time. Have I mentioned how incredibly beautiful and desirable she was? So when the train got back, she said she wanted to walk me back to my car to make sure I "didn't get jumped by some old ladies". I got in and she surprised me by getting into the passenger seat. I had a lot of thoughts pumping through me if you know what I mean. She said she "had one of the best days she ever had". It was very obviously fish or out bait time and I never cheated on a girlfriend, so I did not make a move. She hugged me, kissed me on the cheek, and then did something I won't forget.
HIGHLIGHT QUOTE: This unbelievably fun, beautiful, fit, and clearly interested in me woman handed me her professional business card and a personal card she used for her Olympic figure skating training. I jokingly  said "I'm getting it all, huh?" and she told me she was "in town for two more days" before she had to go to California for training. She smiled and held her mouth open with her eyes locked on mine and said "I'm in 1420," handed me a Hyatt Room Card, and said "Use this and you can spend every ounce of energy you have on my body. Anyway you want me."
She then got out and never took her eyes off me as I slowly drove away.
FUN FACT: I still have that room key card in a dresser, but I didn't go and use it.
TRUTH IS: My God I'd love to see video of what that next night would have been like if I had gone to her room, but I didn't cheat on my girlfriend and that I wouldn't change. But the temptation, I mean unreal.

3. There were several other such moments that I can't cover now, but needless to say the moments were a lot a like. Another one was with a well known super hot and pretty well known young actress that kissed me at a party in NY after we'd talked and hung out for a while at a time when I was single.
HIGHLIGHT QUOTE: She then nibbled on my ear and said "Every man in this place wants to fuck me, but I want to fuck you." I do not know what I was thinking, but I thought she was a little too buzzed and I think we were getting a bit too much attention in the place because people knew who she was. I got uneasy about it, and I took her home but didn't go up with her. She told me "you don't know what you're missing" when she walked in, and I have really wondered what I've missed a couple hundred times since that night. I just got uneasy with people taking pictures and people watching us at her door and all that.
I've seen her countless times on TV. She starred on a show not long ago. When I see her I always privately think "My God she's hot and My God I'm stupid." But there is some fun in knowing that I could have had her and that nobody really knows about it outside of a couple friends. So it's my little unexplained smile when her name comes up.

THIS WAS A GREAT TOPIC CREATION BYE THE WAY! Kudos.

-- Modified on 7/5/2016 12:48:35 AM

Years ago, a teammate and friend of mine broke up with his long-time girlfriend.  She was not only beautiful, but really sweet and fun.  Every guy on our team wanted her, including me.  I knew she thought I was "sweet" and funny.  But she had her pick of most any guy and I was just a skinny, slightly geeky guy.

A week or two after their break-up, I was at a party at the house she shared with multiple girls.  Late night, party winding down, I was both tired and a little tipsy.  She and one of her housemates declared that a couple of us were too drunk to drive home and invited us to stay the night.  My best friend eagerly headed off with the other girl.  So the hotty and I were left alone.  As I settled onto the couch, she invited me to share her bed.  I was thrilled ... until I sobered up enough to think ahead.

They had broken up before and quickly gotten back together.  She really loved him and he was very much the jealous type.  I lay down thinking I had to resist my primal urges until I could pass out.  She did NOT help my cause by coming to bed in a thin, cropped t-shirt and lacy panties. She almost killed me when she backed up against me and spooned.

I don't think I slept a wink all night but I did manage to hold out.  In the morning she gave me a huge hug and light kiss.  Bleary eyed, I headed off with my friend as he lambasted me for passing up the opportunity of a lifetime.

Weeks later, she did indeed get back together with her boyfriend.  They are happily (I assume) married and have two cute little children.

Never will know what could have been, but I see what is.  Regret passing up the opportunity?  Yep!  Would I change a thing given the chance again?  Nope.  *sigh*

@SimpleTruth You absolutely do know what would have happened.  That's why we all remember these almost encounters so vividly.

@CountryGuy8 That’s pretty wild. You usually don’t hear about passing up a a chance and then getting a second chance to take part.

@Senator.Blutarsky I absolutely get how you feel looking back on that one. I was just that same kind of stupid many times with women. But doing the right thing has a price as seen by all these posts.

@mrfisher You have such a great straight forward way of telling your stories. And I’ll bite about hearing the rest of that story with the phone call.

@subrob27 No doubt her husband knows or at least is pretty damn sure what went on, but that must have been one hell of a week. It would have been great to hear about the start of the first time when you finally gave in. What put you over the line to make a move?

It’s so funny how many of us have passed up incredible women we’d love to have.

-- Modified on 7/5/2016 9:11:43 AM