luvslingerie200
Experienced
- Joined
- Aug 25, 2013
- Posts
- 852
Blew my one and only (so far) opportunity for a threesome when I was in my twenties.
A possible sexual moment you let it pass and regret it
- Thread starter live4thebj
- Start date
OlderBtm4U
Literotica Guru
- Joined
- Mar 30, 2020
- Posts
- 1,186
Do tell. Please.
Silvergrizzly31
Really Experienced
- Joined
- Sep 14, 2017
- Posts
- 176
SOOOOOO many opportunities to count when I was so shy and not confident at all. From the time I was at a party and had a girl come up to me and ask if I could walk her back to her dorm, to the time where I had a lady with her head in my lap talking about how she was so sexually frustrated, and all I did was listen and not take that hint LOL. i am really glad I wised up and am able to share some of my experiences rather than wishing I could
cdstefi
Lingerie addict
- Joined
- Dec 26, 2021
- Posts
- 2,909
Oh man. This is a thing I've regretted all my life.
So I was a late starter. Was somehow in the position of chilling (before Netflix, decades before) with a girl I adored at uni, Fay, she'd been out with a couple of my male friends but they had kinda finished, we were listening to my records (great musical taste btw) and we were very relaxed with a couple of joints.
I have no idea why I didn't press things home. She was sexy as fuck and very open about it. I'd cut my finger earlier and she sucked on it before putting a plaster on it. She'd tasted my fucking blood, and that's not a thing anybody does lightly. We were so relaxed. I could have kissed her, I think she'd have responded, and I could have lost my virginity that night. I couldn't bring myself to do it.
Hindsight is a wonderful thing. It'd have changed the course of my life for sure. I could easily have fallen in love with her and married her, or somebody else like her if it hadn't worked out. Instead it took me several more years, but things worked out how they did, I did eventually get married, had four great kids, got amicably divorced, had a few flings, got married again to the second love of my life who also adores my (all grown up) kids, and I don't regret a damn thing.
Except not fucking Fay. She was the first really outright, sexually empowered, on her own terms girl I'd thought about like that. Which made her more than a little intimidating to virgin me. If I'd known then what I know now, I'd have kissed her and the universe would have shifted.
So I was a late starter. Was somehow in the position of chilling (before Netflix, decades before) with a girl I adored at uni, Fay, she'd been out with a couple of my male friends but they had kinda finished, we were listening to my records (great musical taste btw) and we were very relaxed with a couple of joints.
I have no idea why I didn't press things home. She was sexy as fuck and very open about it. I'd cut my finger earlier and she sucked on it before putting a plaster on it. She'd tasted my fucking blood, and that's not a thing anybody does lightly. We were so relaxed. I could have kissed her, I think she'd have responded, and I could have lost my virginity that night. I couldn't bring myself to do it.
Hindsight is a wonderful thing. It'd have changed the course of my life for sure. I could easily have fallen in love with her and married her, or somebody else like her if it hadn't worked out. Instead it took me several more years, but things worked out how they did, I did eventually get married, had four great kids, got amicably divorced, had a few flings, got married again to the second love of my life who also adores my (all grown up) kids, and I don't regret a damn thing.
Except not fucking Fay. She was the first really outright, sexually empowered, on her own terms girl I'd thought about like that. Which made her more than a little intimidating to virgin me. If I'd known then what I know now, I'd have kissed her and the universe would have shifted.
write_or_wrong
Exploring
- Joined
- Mar 23, 2012
- Posts
- 540
That's what you get for being a good guy. (Don't worry, I'm one too.)
David_down_south
Experienced
- Joined
- Aug 6, 2015
- Posts
- 37
Can you regret not taking your shot but also not regret it didnāt happen at the same time?
A number of years ago a very attractive woman started to work at the same company I was working at and we were both supervisors at the company we worked for. Thankfully her onboarding partner was another supervisor; and I say thankfully because I was married and she was kind of woman I was instantly attracted to. Her smile could put you at ease in an instant and her overall personality was just a joy to be around.
We had very limited interactions the first few months she was there but eventually our manager asked if I could help her with her under performing teams. I agreed and it started out professional and innocent as I shared pointers and procedures I had implemented with my teams. Soon though, we were both looking for any little reason to visit the other at their desk. This went on for a number of weeks before I eventually worked up the courage to ask her out for coffee. Also had to convince myself that it was just coffee and nothing more, but we all know it was a lie I was telling myself.
As we lived on opposite sides of the city we decided it would be best to just meet up before work. We did this 2-3 times, having a wonderful morning chats as she drank her coffee before heading into work. Then one morning she said she didnāt want to go inside and would rather just sit and chat in her car. There was a lot of staring into each others eyes, hand holding, and hands brushing up against the others body but nothing more beyond that. Part of me wanted nothing more then to take her there in that coffee joints parking lot in her car but the gentleman inside me would not allow me to let this be how we first had sex. So after sitting and chatting for about and hour we both headed to work.
Soon after we both decided that continuing down that path could have major implications both professionally and personally so we made sure to keep our distance. Six months later I ended up getting a promotion in another state and left.
To this day though I regret not taking my shot in that coffee shopās parking lot but realize how messy things could have been if I did
A number of years ago a very attractive woman started to work at the same company I was working at and we were both supervisors at the company we worked for. Thankfully her onboarding partner was another supervisor; and I say thankfully because I was married and she was kind of woman I was instantly attracted to. Her smile could put you at ease in an instant and her overall personality was just a joy to be around.
We had very limited interactions the first few months she was there but eventually our manager asked if I could help her with her under performing teams. I agreed and it started out professional and innocent as I shared pointers and procedures I had implemented with my teams. Soon though, we were both looking for any little reason to visit the other at their desk. This went on for a number of weeks before I eventually worked up the courage to ask her out for coffee. Also had to convince myself that it was just coffee and nothing more, but we all know it was a lie I was telling myself.
As we lived on opposite sides of the city we decided it would be best to just meet up before work. We did this 2-3 times, having a wonderful morning chats as she drank her coffee before heading into work. Then one morning she said she didnāt want to go inside and would rather just sit and chat in her car. There was a lot of staring into each others eyes, hand holding, and hands brushing up against the others body but nothing more beyond that. Part of me wanted nothing more then to take her there in that coffee joints parking lot in her car but the gentleman inside me would not allow me to let this be how we first had sex. So after sitting and chatting for about and hour we both headed to work.
Soon after we both decided that continuing down that path could have major implications both professionally and personally so we made sure to keep our distance. Six months later I ended up getting a promotion in another state and left.
To this day though I regret not taking my shot in that coffee shopās parking lot but realize how messy things could have been if I did
write_or_wrong
Exploring
- Joined
- Mar 23, 2012
- Posts
- 540
Nicely told, thanks. So hard to do what's right when both of you want to do what your heart (and other organs) are telling you to do. At least the experience can be wank-fodder when you consider the theoretical interactions the two of you could have had.
Wonderer67
Optimistic nihilist
- Joined
- Sep 25, 2020
- Posts
- 19,147
My wife and I were on vacation and we were talking about opening up our marriage (which never happenedā¦)
We were in a cool antique/cool used clothing store in New Haven. My wife was trying on some vintage lingerie and there was another woman there shopping. We ended up talking to each other, she was an assistant professor at the university there, a physicist. Very cute/sexy. She ended up helping my wife, choose some lingerie, and we checked her out in some clothing for a costume party.
No nudity but wife and I were getting some vibes. We ended up talking and having a great conversation. Then we asked her out to have a drink with us.
We had a great time, got slightly drunk over a beer or two, but she had to go.
A total regret that we never pulled the trigger or even asked her for her number.
My wife and I were talking about this just yesterday as we were cleaning out some old stuff out of her lingerie drawer which sparked the memory.
What might have beenā¦
We were in a cool antique/cool used clothing store in New Haven. My wife was trying on some vintage lingerie and there was another woman there shopping. We ended up talking to each other, she was an assistant professor at the university there, a physicist. Very cute/sexy. She ended up helping my wife, choose some lingerie, and we checked her out in some clothing for a costume party.
No nudity but wife and I were getting some vibes. We ended up talking and having a great conversation. Then we asked her out to have a drink with us.
We had a great time, got slightly drunk over a beer or two, but she had to go.
A total regret that we never pulled the trigger or even asked her for her number.
My wife and I were talking about this just yesterday as we were cleaning out some old stuff out of her lingerie drawer which sparked the memory.
What might have beenā¦
David_down_south
Experienced
- Joined
- Aug 6, 2015
- Posts
- 37
Canāt say I ever used it as āwank-fodderā. Iāve imagined what could have happened a number of times but never used it in that manner. I think itās because I enjoy the memory of the interactions as they are.
Shadowslayer25
Degenerate
- Joined
- Aug 16, 2022
- Posts
- 7
There are several that come to mind from a summer fling I had back in college.
1. This girl was in between apartments, her lease ended 2 months prior to the start of the new lease, so she was crashing with a friend/co-worker in the interim. I was over at the apartment one night, and we started making out and getting handsy on the couch, directly in view of the front door. As things progressed, I remembered the friend was due to get home at any moment, got nervous, panicked and suggested we take it up to the bedroom.
The thing is, both this girl and the roommate/friend were very open sexually, and her friend was constantly going on about her sexual exploits to the point I doubt it would have even phased her. Every time I think about it, I kick myself all over again for what might have happened had we stayed and the friend walked in on us. Ever since then I have had a strong desire to get caughtā¦ but right set of circumstances have never presented themselves since.
2. We went hiking on a local trail, that was somewhat out of the way to get to, and stopped to rest at an alcove that overlooked the river. This place was shaded enough that you had to get fairly close to see inside, which provided an almost perfect opportunity to fool around away from prying eyes. After chatting for a couple minutes, one thing led to another and our tongues were locked in a dance. From there she made the first move and her hand maneuvered its way down to my crotch, while my hands were busy exposing her chest from the confines of the sports bra she was wearing. After about a minute or two of she glanced around and after seeing the coast was clear, dropped to her knees, pulled out my cock, grabbed my ass and started rocking my hips back and forth making until she was gagging, and saliva was dripping from her chin. Unfortunately about a minute (or soā¦ I wasnāt exactly counting) later we heard voices coming in our direction and we had to scramble to get our clothes back on.
3. Prior to the events of 1 and 2 above, I had discovered a cam site that let you broadcast (for fun) without going through the hassle of verifying. One day I decided to get on there and broadcast myself, and that was the day I discovered I had an exhibitionist kink. This went on for several months, and I started getting a lot of views on a regular basis. This was a huge rush, so I increased the frequency with which I would broadcast. However at the time I was not seeing anyone, so this was my only sexual outlet, and I began to get frustrated and the desire for companionship only grew.
Several months later I started seeing the girl from the previous encounters. Bear in mind, all the while I was broadcasting, the desire to bring someone else on and stream/fuck on camera continued to grow. After we started seeing each other however, this desire faded to the back of my mind and didnāt resurface until we had gone our separate ways.
Knowing what I do about her personality, and how openly she flaunted her sexuality, I canāt help but think that if I had brought it up back then, she would have been at least interested in testing the waters, if not fully on board.
1. This girl was in between apartments, her lease ended 2 months prior to the start of the new lease, so she was crashing with a friend/co-worker in the interim. I was over at the apartment one night, and we started making out and getting handsy on the couch, directly in view of the front door. As things progressed, I remembered the friend was due to get home at any moment, got nervous, panicked and suggested we take it up to the bedroom.
The thing is, both this girl and the roommate/friend were very open sexually, and her friend was constantly going on about her sexual exploits to the point I doubt it would have even phased her. Every time I think about it, I kick myself all over again for what might have happened had we stayed and the friend walked in on us. Ever since then I have had a strong desire to get caughtā¦ but right set of circumstances have never presented themselves since.
2. We went hiking on a local trail, that was somewhat out of the way to get to, and stopped to rest at an alcove that overlooked the river. This place was shaded enough that you had to get fairly close to see inside, which provided an almost perfect opportunity to fool around away from prying eyes. After chatting for a couple minutes, one thing led to another and our tongues were locked in a dance. From there she made the first move and her hand maneuvered its way down to my crotch, while my hands were busy exposing her chest from the confines of the sports bra she was wearing. After about a minute or two of she glanced around and after seeing the coast was clear, dropped to her knees, pulled out my cock, grabbed my ass and started rocking my hips back and forth making until she was gagging, and saliva was dripping from her chin. Unfortunately about a minute (or soā¦ I wasnāt exactly counting) later we heard voices coming in our direction and we had to scramble to get our clothes back on.
3. Prior to the events of 1 and 2 above, I had discovered a cam site that let you broadcast (for fun) without going through the hassle of verifying. One day I decided to get on there and broadcast myself, and that was the day I discovered I had an exhibitionist kink. This went on for several months, and I started getting a lot of views on a regular basis. This was a huge rush, so I increased the frequency with which I would broadcast. However at the time I was not seeing anyone, so this was my only sexual outlet, and I began to get frustrated and the desire for companionship only grew.
Several months later I started seeing the girl from the previous encounters. Bear in mind, all the while I was broadcasting, the desire to bring someone else on and stream/fuck on camera continued to grow. After we started seeing each other however, this desire faded to the back of my mind and didnāt resurface until we had gone our separate ways.
Knowing what I do about her personality, and how openly she flaunted her sexuality, I canāt help but think that if I had brought it up back then, she would have been at least interested in testing the waters, if not fully on board.
I was at my local rock/metal club, I was on my own, waiting for friends to arrive and 2 or 3 women approached me, #1 was practically begging me to buy her a drink, I wasn't in the mood for it, #2 saw my hesitation and said that #1 would give me a blow job if I did.
It seemed a bit too good to be true and I didn't want to get caught at my regular haunt, so I declined.
I later realised I could have gone to the end of the garden and not be seen.
She probably would have taken the drink and not paid up, but there's part of me that wishes it had happened.
It seemed a bit too good to be true and I didn't want to get caught at my regular haunt, so I declined.
I later realised I could have gone to the end of the garden and not be seen.
She probably would have taken the drink and not paid up, but there's part of me that wishes it had happened.
SPARTAN047
Veteran Fetishist
- Joined
- Nov 23, 2015
- Posts
- 14,275
Lots of them will say anything to get you to do something simpish for them, and then say you're not obligated to have sex, so just as well.
Up4fun&69
Nude and Waiting
- Joined
- Oct 13, 2004
- Posts
- 426
I guess as one gets older, you think about the past and what might have been. I've posted two situations here, already. But a few more popped into my head after running across some things which triggered the memory.
I was in my kitchen and ran across an old index box of drink recipes from the days I bartended. I was 25 (looked younger), trying to break into the acting world in L.A., and bartending was one of my side gigs. I was registered with a party service company out of Westwood which served some of the richer folks on that side of the world. I had already worked at several house parties in Bel Air and the Hollywood Hills. I was hired on to be part of a 4-man crew serving a sweet-16 birthday party in Beverly Hills. Upon arriving, I was floored by the 15 ft. waterfall-fed swimming pool and the pool house, which was bigger than many of the homes I have since lived in. Besides the 12 ft bar, the pool house had two hallways and each had bathing suits hung up as "party gifts" for both the teenagers and the adults attending the party. As the night wore on, things started to get wilder with more people forsaking the bathing suits and swimming nude, and couples making out in the shadows all around the pool. I had been behind the bar at the pool house all night and about halfway through the party, the birthday girl started to hang around the bar and chat me up. As things became wild outside and my final shift for the night was over, she asked me to come up to her bedroom and give her the present she really wanted. I fumbled around with the excuse that I had to clean up and leave as my shift was over. She said, 'That means you're off the clock and can do whatever you want, and I want you." I then mumbled something about her father wouldn't be happy if he found out. And she pointed to her naked father making out with one of her girlfriends. I finally just said that I didn't think it was a good idea and left.
Even now, I know I did the right thing, given her age. But I still wonder what it would have been like. But the day after the party, I had a whole new outlook on things as the owner of the party service company called and fired me because, and I quote, "The customer is always right. How dare you not do as you were asked and give us a bad name!" Wow.
I was in my kitchen and ran across an old index box of drink recipes from the days I bartended. I was 25 (looked younger), trying to break into the acting world in L.A., and bartending was one of my side gigs. I was registered with a party service company out of Westwood which served some of the richer folks on that side of the world. I had already worked at several house parties in Bel Air and the Hollywood Hills. I was hired on to be part of a 4-man crew serving a sweet-16 birthday party in Beverly Hills. Upon arriving, I was floored by the 15 ft. waterfall-fed swimming pool and the pool house, which was bigger than many of the homes I have since lived in. Besides the 12 ft bar, the pool house had two hallways and each had bathing suits hung up as "party gifts" for both the teenagers and the adults attending the party. As the night wore on, things started to get wilder with more people forsaking the bathing suits and swimming nude, and couples making out in the shadows all around the pool. I had been behind the bar at the pool house all night and about halfway through the party, the birthday girl started to hang around the bar and chat me up. As things became wild outside and my final shift for the night was over, she asked me to come up to her bedroom and give her the present she really wanted. I fumbled around with the excuse that I had to clean up and leave as my shift was over. She said, 'That means you're off the clock and can do whatever you want, and I want you." I then mumbled something about her father wouldn't be happy if he found out. And she pointed to her naked father making out with one of her girlfriends. I finally just said that I didn't think it was a good idea and left.
Even now, I know I did the right thing, given her age. But I still wonder what it would have been like. But the day after the party, I had a whole new outlook on things as the owner of the party service company called and fired me because, and I quote, "The customer is always right. How dare you not do as you were asked and give us a bad name!" Wow.
jerryb1966
Daddy For Fun
- Joined
- Mar 24, 2018
- Posts
- 991
When I was young, a buddy was out of town on work travel and he asked a friend and I to check on his wife. We stopped by their apartment and we had a beer with her. She had another and another and started to flirt with both of us. We left before things got out of hand. We were pretty sure we couldāve tagged teamed her. She was a hot little slut who would have been down for her holes to be filled. They divorced within two years after she had another manās baby. Shouldāve fucked that slut.
Years ago, I had a manager that would flirt with my a lot. One day we were working late trying to wrap up a project and he came up behind me putting his arms on either side of me and whispered in my ear that he really wanted to fuck me. I nearly melted but this was back when I was still being a good and loyal wife and I didn't go through with it. Absolutely wish I could go back and just go for it.
irishblade
Dirty Little Secrets
- Joined
- Dec 24, 2012
- Posts
- 2,322
I know Iāve posted this elsewhere but it fits in a lot of places Lol Years ago, I was seeing a married gal who was in an open relationship. We werenāt sleeping together. Just a lot of fooling around. Anyway, her husband has a monster BWC. She invited me on a beach trip with just the two of them because the original third flamed out. It was a one bedroom hotel with two queens. I had no excuse to not go yet I chickened out anyway. I am not a man of regret but I regret that missed opportunity every day.
showmeporn
19 m for older F
- Joined
- Jan 4, 2025
- Posts
- 58
Walking in on my 22 son getting ready to take a shower. All hard with morning wood too.
Why did I leave ? Thinking what could have been...
Why did I leave ? Thinking what could have been...
Anexpat19
Tongue twister
- Joined
- Dec 27, 2024
- Posts
- 121
In college I was sleeping over at my girlfriendās dorm. Her roommate also had a boy over and as weāre trying to go to sleep we hear them fooling around. We could hear their moans and their giggles and her wetness as he slid into her.
I was getting turned on, and I could tell my girlfriend was too. I started feeling her up and pushing my hard cock into her ass but she meekly rejected my initial advance.
I wish I had tried again because I know she was feeling the same thing I was and I know it wouldāve opened up a whole new very fun experience.
I was getting turned on, and I could tell my girlfriend was too. I started feeling her up and pushing my hard cock into her ass but she meekly rejected my initial advance.
I wish I had tried again because I know she was feeling the same thing I was and I know it wouldāve opened up a whole new very fun experience.
lmc89
Really Experienced
- Joined
- Jan 31, 2021
- Posts
- 243
A few years ago a group of us came to London for a football game, I stayed an extra night to see the city and because I had an interview.
A bit bored on the last night I went to a rooftop bar in Vauxhall and got speaking to two women, the conversation was really interesting about art/politics etc. They had to leave at midnight to catch the last train to Surrey.
The fitter one gave me her number, I messaged and thanked for a good night and she messaged back to say she had missed her last train, I offered her to stay at my hotel but was not persuasive enoughā¦ we messaged the next morning, she was flirty and would have been up for meeting but I had to catch a flight
A bit bored on the last night I went to a rooftop bar in Vauxhall and got speaking to two women, the conversation was really interesting about art/politics etc. They had to leave at midnight to catch the last train to Surrey.
The fitter one gave me her number, I messaged and thanked for a good night and she messaged back to say she had missed her last train, I offered her to stay at my hotel but was not persuasive enoughā¦ we messaged the next morning, she was flirty and would have been up for meeting but I had to catch a flight
Japansurfer
Used and abused
- Joined
- Sep 26, 2023
- Posts
- 2,347
Not taking up an ex and her daughter. she wanted to introduce her to men and use me to teach her daughter how a man could be used for pleasure. Sounds like a porno but this was after her daughter walked in on me tied to the bed! The mother had apparently already given her practical experience of how to masturbate.
At a backyard party when I was freshly 18, the auntie of my best friend was very heavily hitting on me. But I only had a tent, no mattress or anything, so I knew I couldn't take her anywhere. So I ended up just kind of, hugging her while everyone talked. She excused herself and basically disappeared for the rest of the night. Turns out she had a room all to herself at the house and we could have gone there
One regret? Geez, I have so many, but I'll try just one:
My wife and I were having dinner with another couple, I'll call them Lisa and Jerry. I'd been fantasizing about Lisa, a small dirty-blonde with big tits who was a bit of a flirt. As the evening wore on, the four of us kicked back with drinks, and both the wives were getting tipsy and frisky.
Out of the blue, my wife and Lisa started trading snarky insults, until my wife suddenly said, "If you don't shut up, I'm going to pinch your nipples off."
Lisa let out a gasp, thrust out with her chest and replied, "You wouldn't dare."
My wife looked at me as if asking me what to do, but I was in shock. I desperately wanted to see the situation escalate, but I was afraid of saying the wrong thing. All I could say was, "Well, you got yourself into this, so you'll have to get yourself out." With that, all the sexual tension evaporated, and the two women went back to their drinks.
A short time later, Jerry got a job transfer, and they moved away.
Why did I have to be so responsible? Why couldn't I have said something more like, "Go ahead, you can't ignore a dare"?
I've been kicking myself ever since. To make matters worse, I later learned that Lisa had developed an interest in women.
Bummer.
My wife and I were having dinner with another couple, I'll call them Lisa and Jerry. I'd been fantasizing about Lisa, a small dirty-blonde with big tits who was a bit of a flirt. As the evening wore on, the four of us kicked back with drinks, and both the wives were getting tipsy and frisky.
Out of the blue, my wife and Lisa started trading snarky insults, until my wife suddenly said, "If you don't shut up, I'm going to pinch your nipples off."
Lisa let out a gasp, thrust out with her chest and replied, "You wouldn't dare."
My wife looked at me as if asking me what to do, but I was in shock. I desperately wanted to see the situation escalate, but I was afraid of saying the wrong thing. All I could say was, "Well, you got yourself into this, so you'll have to get yourself out." With that, all the sexual tension evaporated, and the two women went back to their drinks.
A short time later, Jerry got a job transfer, and they moved away.
Why did I have to be so responsible? Why couldn't I have said something more like, "Go ahead, you can't ignore a dare"?
I've been kicking myself ever since. To make matters worse, I later learned that Lisa had developed an interest in women.
Bummer.
Threesome with my best friend and a college classmate of ours. She was smoking hot and horny as hell.
Neither my best friend nor myself could lift it up despite our genuine excitement at having a blast. We just went back to sleep and nothing happened
Neither my best friend nor myself could lift it up despite our genuine excitement at having a blast. We just went back to sleep and nothing happened
svengali_decL
His Serene Boldness
- Joined
- Nov 29, 2022
- Posts
- 2,207
old_hippy_46
Over the hill
- Joined
- Dec 29, 2024
- Posts
- 396
I have one i think about now and then. I met a woman who was a dead ringer for Michelle Phillips of the Mama's and Papa's. I was flirting a lot with her and she said how about we go to my house, get naked, and let my pet boa constrictor slither over us.
NO THANK YOU
