Sexual Regrets

[Cutestarr65]

Who here has a story of someone they shouldn't have slept with/fucked/done sexy things with? Can be for any reason.

Go!

-CS

 

[Solsurfer]

I don’t have any of those stories. But numerous stories of things I could have done if I wasn’t such a “good boy” as a teenager. I still think back on some of those scenarios and fantasize about what I could have done with that girl, at that time.

 

[Justfantasies]

A very pretty GF from when I was in my teens and still a virgin and so was she. I didn't fuck her -- I was too shy. So she went on vacation and fucked three guys -- but she never fucked me.

 

[twister947]

My ex liked rough sex: she dropped plenty of hints. But that was so far off of my radar, I didn't even know what it was. She was also a pathological liar; I should have punished her.

 

[Boredozhub]

I grew up in Australia and became a trucker as soon as I was old enough, back in the day we used to give hitchhikers a ride with no second thought. One time I had another driver with me, driving team and we picked up a couple of girls from a roadhouse, It was my turn in the bunk so the older girl sat up front and the other one got in with me, we ended up fucking almost immediately, but there were no words spoken, she was completely passive very cute and a smoking body, but after all was said and done, I wish I hadn't fucked her, she seemed like it was done out of expectations and I felt so bad. Anyway thats the only fuck I've ever had that I came to regret.

 

[waratah]

A very pretty GF from when I was in my teens and still a virgin and so was she. I didn't fuck her -- I was too shy. So she went on vacation and fucked three guys -- but she never fucked me.

Similar. Socially anxious, or lacking confidence, in early to mid 20's, missed a dozen cues and clues that prolly would have lead to adventures. Also regret not having access to the internet for casual liasions that youngsters have now.

 

[Justfantasies]

Similar. Socially anxious, or lacking confidence, in early to mid 20's, missed a dozen cues and clues that prolly would have lead to adventures. Also regret not having access to the internet for casual liasions that youngsters have now.

In my case the willingness with which she fucked other guys when given the chance, suggests that this was a real opportunity

 

[amofiga]

Back when I was still working there was a woman at the company who was quite attractive. She was married to a guy who also worked at the company and on certain programs, actually worked for me. His wife worked in another building, but I had a fair number of dealings with her because of her position which was responsible for government and customer property at our site. We were actually good friends but I thought it was because of the fact that her hubby often worked for me. We often kidded and flirted but in my brain, it was just fun. Both of them left the company in the late 90's so my story relates to the years in the 80's and early 90's.

I always noticed that she wore an ankle bracelet and very high heel "fuck me" pumps. There is a story associated with those shoes but this isn't it. It wasn't till years after she left the company that I learned that ankle bracelets were often a signal for a hotwife. Had I known then what I know now, I would have certainly asked her about that bracelet and if it meant what I had learned. Perhaps our innocent "flirting" could have progressed into something quite a lot more interesting. Way too much water under the bridge now.

 

[MisAlicia87]

Hubby and I were playing our school girl game in NYC many years ago. I dressed up and we'd go to public places with me "alone" him in tow. Appealed to my exhibitionist side and his voyeur cuck tendencies. Had many hot experiences until I was almost gang raped on a crowded subway by a very rowdy and drunk group of guys. Hubby stepped in but was quickly over powered thought they'd kill him, thankfully several other people stepped up too and we were able to get out at the next stop and made a run for it. Last time we ever played that game, in public. Truly stupid and regretful.

 

[Boredozhub]

Hubby and I were playing our school girl game in NYC many years ago. I dressed up and we'd go to public places with me "alone" him in tow. Appealed to my exhibitionist side and his voyeur cuck tendencies. Had many hot experiences until I was almost gang raped on a crowded subway by a very rowdy and drunk group of guys. Hubby stepped in but was quickly over powered thought they'd kill him, thankfully several other people stepped up too and we were able to get out at the next stop and made a run for it. Last time we ever played that game, in public. Truly stupid and regretful.

WOW! I'll say

 

[twister947]

Jack Reacher is never there when you need him.

 

[Lost_Yonder]

My only true regrets are the opportunities I missed out on being too naive or stupid at the time. As for regretting any actual sexual experience - there are probably a few I could have done without, but I certainly don't regret them...

The biggest regret, or one of them, as for a missed opportunity. When I was in graduate school one of my friends was living with an undergrad woman who had an extremely hot friend who was super nice and fun to be around with - and living with a guy at the time. One semester we ended up in the same class that a number of grad students had to sit in on. There was a group project and being that we knew each other decided to work together. We met at her house, her bf was out of town. Throughout the evening she was extremely flirtatious but I just brushed it off as her being friendly. She even had a loose top on that I could get very clear views of her amazing breasts. I did nothing.

A few months later I started dating a woman and we all hung out at our mutual friend's place. She cornered me and asked me if I remembered that evening - which I did, and still do! She told me that she assumed I was gay so she herself didn't do anything more bold since I was so reluctant to even respond to her flirtations. She had in fact broken up with her bf and really wanted to date me, but it was not meant to be...

 

[beatingoff]

Service Call

When I worked as a mechanic,I used to moonlight,doing small jobs for various friends. One gal worked at the corner store nearby. I was in the fall,she wanted her winter tires put on. They were in the shed at her house. We picked an evening, I was to pick up her vehicle,get the tires,put them on & deliver the car back to her house.

I got everything done,back to the house,took the keys in,and tell how much.She was an avid hunter ,and been out that day. I had smelled some pot smoke residue in the vehicle,but didn't really put it all together. I found her at the kitchen table, having a cigarette,in a bathrobe. we have always been friendly,exchanging hugs & flirting at her work for years. one thing led to another & I asked for a hug.When she did I felt her back and ass to find nothing on underneath. I took the opportunity to put my hands under the robe to get a good grip on her ass. I complimented her on her body,that I always thought she was hot. She thanked me,and I reached up to fondle her breast.

I asked if I could share a "secret"...that I always wanted to lick her pussy and would love to set her on the table an do just that. She was concerned that her daughter would be coming home soon,and that couldn't happen. I took another hug,opened the robe to at least get a view or the beauty before me. Said again,how sexy I always thought she was, and when home.

Looking back ,I think the pot had allowed me some liberties that she may not have given me otherwise. We never talked about the evening afterwards. She quit her job a few months later,to work at a processing plant. Recently I heard she had moved in with a fellow about 20km from her old home. I saw her the other day working at our local Walmart. I talked to her a bit,and got a Christmas hug from her.

I still regret not getting the chance to pleasure her. I still jerk off to the memory of that evening.

 

[screwher]

My only real sexual regret is not sharing my fantasies involving my wife with her when I started having them. Many years ago (too many actually) after she cheated on me I started fantasizing about her having sex with other men. I finally confessed my desires a few years ago after her second tryst. This kickstarted our hotwife marriage. Who knows for sure (as people change out the years) but I often wonder what might have happened if I confessed back then. Maybe we would've opened up our marriage then and other men could have been screwing her all this time.

 

[Nidan]

I don’t have any of those stories. But numerous stories of things I could have done if I wasn’t such a “good boy” as a teenager. I still think back on some of those scenarios and fantasize about what I could have done with that girl, at that time.

Mainly this is is the same for me. Or if I hadn't been so clueless.

But there is one time I just shouldn't have bothered. With a fuck buddy, she had a boyfriend but srill wanted to hang out. I wasn't sure why. I assumed we were gonna fuck. I kind of pushed the issue (are we fucking or what? Definitely nonody forcing anyone here, to be clear) but when we got down to it, neither of us were actually into it.

 

[UnderMyKilt]

Who here has a story of someone they shouldn't have slept with/fucked/done sexy things with? Can be for any reason.

-CS

There's several, and I've related this before, but this is perhaps the most extreme.

I knew better than to get involved with this girl but in the end my little head won the internal argument. That said, and to make no mistakes about some of the details herein, I certainly don’t hold mental, or other, health issues against anyone.

There was a young lady in the parts department of a large construction equipment company for which I worked in my mid-twenties. When I worked, and lived, in the town where the company was headquartered I used to see her when I'd go to the parts warehouse or when she'd deliver parts to my office. She had a dynamite body, tall and lean, strawberry blond hair, and with the most perfect and perky tits and a tight ass. She would wear her pants so tight, and I mean denim jeans and not tights, that you could see her camel toe clearly. Once, when a co-worker asked how she could get those tight jeans on, she responded, "I Vaseline my pantyhose."

In any event, and though she was flirtatious and I was interested, my position in the company told me I shouldn't go "dipping in the company inkwell" and I intentionally gave off the "unavailable vibe". Since she wasn’t in my immediate chain of command it was probably OK but I still had qualms.

I ended up promoted to manage another branch with the company and moved to another city. I had occasional contact with her when I'd call to order parts and, when I'd go to headquarters for meetings, I'd sometimes stop by the warehouse to pick up parts for my equipment that was down or just to replenish my inventory. She was still always flirtatious but I just assumed she was like that with everyone.

When inventory season rolled around I got a call from the Big Boss, the company owner and General Manager, telling me that they were sending her up to my branch to help with our inventory and that she'd be staying in town for a few days. Upon learning this, and having seen her in the past, my crew was all a twitter and the sexual jokes were rampant. I, of course, being the educated and responsible manager that I was, had to remind them of the sexual harassment policies.

In any event, the day finally arrived and she arrived on a Thursday morning driving a company pickup. We got to work and even though one of my employees was hitting on her, hard, her attention was obviously focused on me. The body language was all there, the eye contact, reaching out and touching me when she spoke, and even some sexual innuendo. I was flattered, and turned on, but still trying to keep it professional.

When the work day was over my crew punched out and began to trickle out the gate. The guy who had been hitting on her asked if she wanted to go to dinner and she responded that she was really tired and just wanted to get to her hotel. She never got there.

Young girl, strange town, kind of my responsibility to accommodate her so I took her out to dinner at a nearby steak house. Though I tried to slow her down, she drank till she was thoroughly schnockered. As is typical for me, I didn’t drink, not a drop, when I’m intending to drive. Really, I swear, I was only being chivalrous when I decided that I shouldn’t take her to her hotel, since she seemed too drunk to take care for herself, and instead took her back to my place.

My place was a small, quaint, one bedroom, farm house in the middle of a walnut grove outside of town. My intentions were good when I helped her into the house and steered her to my bed, fully clothed, and covered her with a blanket. I then had a bit of single malt Scotch while I sat up for a while and watched a little TV. Finally, I stripped down to my undershorts, pulled out the sofa bed, and fell asleep with the TV on. I'd been asleep for at least a couple of hours when I was awakened by motion next to me. Kisses were planted on my lips, my mouth was invaded by a tongue, and a hand was firmly wrapped around my involuntarily hardening cock. Of course, like any red blooded man, I only briefly thought about the ramifications before thinking “Ah, fuck. Go for it.”

In reality, it was not as if I had much choice in the matter. She was completely naked and before I could even think, much less react, to what was going on she had mounted my cock and was bouncing up and down, cowgirl style, with an intensity and abandon I’ve not seen before or since. It was almost as if she was punishing herself on my cock. She came once, but continued her assault on my cock while repeatedly muttering about wanting to be filled with my sperm (she distinctly said sperm…not cum) and at least once asked me to fill her with babies. I was too far gone to let that thought deter me and, having been without sex for a while, I blasted a copious volume of “sperm” into her vagina as she bore down, seemingly trying to get me as deep as possible and she came again.

She collapsed, lying on top of me, and when she’d caught her breath she thanked me for being a gentleman and looking out for her when she was drunk and we both laughed. We then moved into my bedroom , climbed into bed together, and began kissing and petting at a slower and more intimate pace than before. As someone who worried about such things, I asked about contraception and specifically about her earlier comments about sperm (as opposed to cum) and babies.

Her explanation probably should have rocked me to the core but it didn’t. She said she was using no form of protection against pregnancy, and never had. She said she had severe endometriosis with frequent pelvic pain and that she had never been able to conceive BUT, that she had decided if she was to get pregnant she wanted ME to be the father since I was the “smartest person she knew”. She added that she wanted any prospective kid to have some of my brains. (How’s that for a head trip?) She also apparently believed the largely debunked theory that the best cure for endometriosis was getting pregnant and having a child. (It does work, but generally only for the term of the pregnancy and in some cases while the mother is still breastfeeding). She added that she should be ovulating right then and that if it was going to happen, it would probably be that weekend. (I learned later that it was she who suggested to the boss that she come up and help with my inventory and that she’d even picked the date.)

What she failed to mention to me was the fact that she was bipolar with some other psychotic symptoms occasionally thrown in for good measure. I learned later that the some of the other employees in her department knew she was bipolar and that she’d even been hospitalized when dangerously manic, or severely depressed, in the past. It also became apparent that hypersexual behavior was a characteristic of her manic episodes.

I thought about it..for about a second…before we went back at it, this time with her spread eagle on her back, and I did my best to go as deep as I could to thoroughly paint her cervix with cum and plant my seed. I liked her. I liked her A LOT, and had for a very long time but I had just been fearful of a work romance especially if it went bad. If she had gotten pregnant (presumably with my child) I would have gladly done the proverbial “right thing” and married her. She was hot, and at the time I certainly could have done a lot worse than her for a wife or girlfriend.

The next morning we were back at work and, in spite of some suggestive questions from my employees, we were trying to give the impression of being aloof and professional. When my employee again hit on her, asking her out, she told him that she was driving the 100 or so miles back home right after work. Of course that didn’t happen, and she spent the entire weekend with me.

Over the next several months we openly became an item (she never did conceive) and I would drive to see her on weekends and sometimes even midweek. However, cracks began to appear in the relationship and her emotions, and attitudes toward me, began to be all over the map. One weekend she’d be anxious to see me, we’d have a wonderful time and fantastic sex, while the next she’d treat me like a pariah and say things like, “I could never be with you. You’re too much of a good boy.”

I’d figure it was all over till she’d call and ask why I was “mad at her”, seemingly unaware of how badly she’d treated me. I excused some of the depressive episodes as they sometimes seemed to coincide with periods when she was having severe pelvic pain due to her endometriosis and, sometimes, was taking narcotic pain relievers to deal with it. Through it all, yes, I’d fallen in love with her and, being a rescuer, thought I could “help her”.

In several other episodes, she was screaming in her sleep next to me and, when I woke her up, she just spontaneously wanted to fuck…HARD (admittedly, it was fun till it become too weird). In several similar episodes, she didn’t recognize me for some time after she woke up and, one time, was so disoriented that I had to call EMS and she ended up on a 72 hour mental health hold.

Throughout this, I was working on getting another job since I was unhappy with our employer and wanted to move back to my hometown. The final straw came when, after having an interview and accepting a job offer back home, I went by her place to tell her. I was thrilled that we’d be living in the same town again. I knocked on the door and, when her roommates opened the door to their apartment, there she was on the couch and all over some seedy, filthy, looking biker. No offense to bikers, they’re not all filthy and seedy, but this guy was. I walked away with the sudden realization that perhaps I wasn’t the only guy she was doing while in her manic/hypersexual moods. It hit me so hard that I drove straight to my doctor’s office, a GP that had been caring for me since I was a kid, and asked to be tested for every STD in the catalog.

I gave our employer my two weeks notice and, over those two weeks while I was still working for the same employer as she and still living in the same house, she repeatedly called me. When I moved I was glad that I had a new address, new phone number, and a new employer and that she had no knowledge of any of them.

I later learned, from common friends and former co-workers, that her mental health had deteriorated further into schizophrenia, with total breaks from reality, and that she’d been institutionalized several times and was living under the guardianship of her parents.

I'm sorry. I really liked that girl, but I wasn’t strong enough to deal with it....and...ultimately, I never should have had sex with her in the first place.

 

[WhO2]

I don’t have any of those stories. But numerous stories of things I could have done if I wasn’t such a “good boy” as a teenager. I still think back on some of those scenarios and fantasize about what I could have done with that girl, at that time.

Me, too - my only regrets are the ones I thought wanted to date a nice guy...

 

[FloridaBob]

My only regret was marrying young,and being good all these years. I wish that I'd taken advantage of the few opportunities I had when I was younger. Sigh, what could've been will never be

 

[Coolshoes7]

The title is slightly misleading compared to what it sounds like you're looking for. I've been with people I probably shouldn't have but I don't have any regrets as every instance even the bad ones have been learning points to bring me to the person I am now and I am happy with that person.

I think one of the ones that comes to mind for me was my friend's husband. They had been together for not too long before they got married and I ended up being friends with both of them. They fought a lot about everything from finances to who was running the household and such. For some reason he began venting to me about my friend and how it bothered him. Unfortunately my friend was not a very sexual person and this was one sore point for him as well as he was. To make matters worse they believed that the answer to their fighting was to try and have a child. It worked for a few months before he text me again. There were a few issues they were having and he also said they were having sex but he found it to be boring as it was a minute or two of missionary sex and then to bed. He said there was no intimacy leading up to it and it was very direct and purpose driven and that was it. This continued as they had trouble trying to conceive. Well one evening she was out of town and I later found out she went to visit her parents and they had invited her ex boyfriend they were fond of over for the evening while she was there. This made him very angry, understandably so, as she told him not to worry and to get over it. We decided as a group to go out and get drunk and have a good time. To shorten the story up we went out, got pretty tipsy, and ended up back at his place in his bed going at it like crazy. All in all we had sex about six times while she was gone and nothing really was off limits. She came back and they continued their usual activities. A few weeks later out at lunch she admitted that they were having trouble in the bedroom and at times were even failing to have sex. She asked me for advice as I had never kept it a secret I enjoyed sex. I felt odd giving her tips that I had first hand knowledge of knowing her husband liked but I played it off as best as I could. In the end they did have a son but it didn't save their marriage.

 

[straitupcurious]

I have one so here's the story.
Back in the day when I was in Jr.High as it was known then several of us guys would meet out in the woods during lunch hour swap pics from Playboy and Penthouse talk it up and then all of a sudden one of us would jump up and say " I can't stand it my dick hurts " so with that he'd drop his pants and shorts and start jacking off and as you might guess all would soon follow this lead and soon you have five or six guys pumping their cocks moaning and thoroughly enjoying it. I look back on this time very fondly.
Our little group eventually disbanded as we entered the high school phase took different educational paths etc. getting into girls was a huge factor as well.
Well, one day during summer after we'd left high school for the great world beyond I ran into one of those same guys we talked a bit and he told me they were having a jack off party later that night at his house to come on up if I wanted .
My single biggest sexual regret is not accepting that invitation. I was by then around 19 and was convinced by the prevailing social norms that it was just too gay and a ladies man such as myself shouldn't indulge.
Now looking back through my own lens of maturity I've wished a thousand times I'd manned up and done it. I know what fun it would have been and it's after all a perfectly natural thing so it was a huge sexual mistake I truly regret.

 

[soflabbwlvr]

I have a few. One occurred when I was in my first year of graduate school. I lived in a house with two other students, one of whom was a woman. She was not particularly attractive, but she was a hard core athlete and had great legs. Anyway, I was alone in a new city and feeling lonely, and it was becoming obvious that she had feelings for me. One night after a few beers I went to her room and we had some seriously good sex. For about a month I went to her room every night, fucked her, and then went back to my room. She started to get clingy, and I knew I had to back off. I told her I just wasn't feeling what she felt, and all hell broke loose. We existed in a cold war state for the rest of the school year. That was one time I should have just said no.

 

[liqueur]

I don’t have any of those stories. But numerous stories of things I could have done if I wasn’t such a “good boy” as a teenager. I still think back on some of those scenarios and fantasize about what I could have done with that girl, at that time.

Amen to that!! Girls and guys, both, in my case. And at just about the age when I was starting to come into my own, sexually, I got sucked in to the vortex of a super-ultra-conservative religion, and shut everything down (as best I could). They got you both ways— if you did it, damnation unless you confessed your sins and increased your tithes; if you didn't do it, you were a damnable sinner anyway for even thinking about it. Bitter much? bitter at myself, for letting myself get sucked into all that guilt and all—and wasting my sexual prime in the process.

I was an electrician in those days—did a large part of my work in people's homes. Ah the opportunities that were offered. . . and wasted.

 

[Smallchange4]

Fucked the receptionist (Darla) were I was employed. One night stand after Christmas party. Failed to impress. Tried to blame alcohol. Boasted otherwise to a number of my male colleagues. One way or another word of my misrepresentation got back to Darla. She was not pleased that I had said anything at all about hooking up with her especially when she asked me not to. I may not have except some of the guys had noticed her and I flirting and then us leaving together. My ego did the rest. Darla made sure that the truth of our assignation was put out there. Basically she whispered in a few ears that I had a tiny cock and was crap in bed. Just deserts I guess.

 

[liqueur]

Also, that I never volunteered to lick Mrs. Thompson's clit for her after graduation. She would have accepted the offer. I know that from the way she held me when we danced at the Senior Banquet. . . And her husband sure wasn't doing the job.

I know these things. . . 50 years later

 

[turbocs37]

Many years ago I was dating an older woman. We had been together only once or twice. She had a friend of hers visiting and we ended up on her bed playing keep away with a little Nerf football. There was a lot of "inadvertent" body contact. I was too naive to realise a 3some was being offered. Both were beautiful women. Would have been amazing with my early twenties stamina and short refractory time.