A possible sexual moment you let it pass and regret it

[screwher]

When my wife first cheated, I wish I handled things differently. I was young and it was about four years into our relationship. I was furious and it almost ended up. But soon after I started to become aroused by her tryst.

We’re a hot wife couple now. But in hindsight, we could have been in the lifestyle for many years now. And she could have had sex with many men over those years.

 

[screwher]

One of my tits popped out of my top during an argument at work, I was already married at the time and the guy I was arguing with was a total creep and misogynist but the hungry look on his face still makes me wish I’d put my tit in his open mouth as I sat on his cock.

If I were your husband I’d be disappointed you didn’t end up in his bed over this. Better yet, brought him home and used our marital bed!

 

[SavannaT]

If I were your husband I’d be disappointed you didn’t end up in his bed over this. Better yet, brought him home and used our marital bed!

Well it’d break my heart if my hubby found out but thats another reason it turns me on and I wish I’d done that hehe

 

[Up4fun&69]

There are a few such times of regret. I was (and am, to a lesser degree), shy when it comes to the opposite sex. In the mid-1980s, about 5 years after college, I broke up with who I thought was “the one” and ended up quitting my job (she worked there), and returning to southern CA where I went to college. I worked several odd jobs, including a few acting gigs, so I had plenty of free time. In such times, being a lifelong nudist, I’d drive down to San Diego and spend the day at Black’s Beach. One time, while I sunned on the beach, there was a couple tucked in at the base of the cliff. She was incredible…5’10, curvy but firm, with at least a 40 DD bust. As I lay on my stomach and faced the cliff, she tried everything to get my attention while looking directly at me…spreading sun tan lotion over those huge tits and nipples; spreading her legs and fingering her slit; reaching over and jacking off her hubby; and kneeling in front of hubby and sucking him off. All the while, she kept looking at me and gesturing to me to come up to them. Me, being shy and naive about the world of swinging then, kept trying to look away, but I couldn’t. And I tried to stop my growing erection, but I couldn’t. To escape the situation, I stood up and, with my semi bouncing all about, dove into the water and body surfed a bit. On one run in, I noticed the woman coming down to the water. I swam out and caught the next wave. As I’m body surfing in and the wave is dying, I bump into the leg of someone…the busty woman. I look up, staring into a plump, full pussy with those tits hanging above. I’m quickly getting hard. She offers her hand and “lifts” me up against her body. She kept flirting and rubbing her leg against my hard on and her tits against my chest. After a couple of minutes, she asks if I’d like to come back with her and her husband to their house for some fun. I fumbled and stumbled about having to get back to L.A. and raced back to my towel before quickly drying and leaving. Fifteen years later after a marriage and divorce, I finally found the joy of threesomes with sexually charged couples. I only wish I had gone back with that couple from the beach and learned about such fun then.

 

[zoso682001]

Working at a job in my old hometown with my boss and a coworker one day when an old fb stopped by and asked me to go to lunch with her . I knew what she wanted but the conversation was happening right in front of my boss and the other guy . They could also tell what was going on but I didn't want to get in trouble with the boss .

She did everything but get on her knees and beg . I still said I couldn't go . Later that night both my boss and buddy asked me what the hell was wrong with me . What a dumbass I was !

 

[gtnlynn]

My wife and I started dating at 15 and married at 22. We did just about everything other than fuck each other. She wanted to, but I loved her too much to risk getting her pregnant. I didn't know she was fucking others behind my back. One night we were almost naked, masturbating each other. She spread her legs, used her fingers to open herself to me and said, "I want you inside me." I started to do it, but stopped. She never offered again. I wish I had done it, but she says she is glad we waited until our wedding night.

 

[Inthelastrow]

Yah, here is one. It deals with my wedding night. Like all weddings, there is a ton to do on wedding day. By the time we got to the hotel after the wedding and reception, it was after 11 pm and my wife was exhausted. She fell fast asleep. I didn't have the heart to wake her so I went down to the hotel bar to have a drink. There were a half dozen folks drinking at the bar, including a very attractive lady about my age. As we drank, I told them it was my wedding night and my bride was fast asleep. After cheers and some laughs along with a round of drinks, everyone left but the single chick and I. We chatted and we got rather close, but I just couldn't go back to her room despite her offer. It was my wedding night after all. I am pretty certain she thought it would be cool to fuck the groom on his wedding night, but I passed. I often wonder what would have happened if I had said yes.

 

[Jcam1980s]

Seeing my aunt get changed on a family holiday she took her top off in our lodge living room thinking we were all outside. I saw her magnificent bare tits. I wish I'd have said something or she noticed my instant bulge!

 

[UnexpectedLuggage]

Not suggesting a threesome when it was right there.

Me, buddy and a lady friend of ours went snowboarding. We actually spent much of our time in the lodge because it ended up being unseasonably warm. We got drunk, played strip poker and so forth. My buddy and our friend fucked at one point on said trip while I was asleep.

One evening we were hanging out, our friend was naked, and my buddy was fucking her with an empty beer bottle (why, I don't recall). I thought about suggesting a threesome, because why fuck her with a beer bottle when there were two perfectly good cocks in the room? But, alas, I didn't. I got scared by the prospect of it somehow sounding gay (we were in our early 20's and dumb as shit), so I kept my mouth shut.

All these years later I still regret at least not pitching the idea. She would have been a hell of a good time to tag team, and the mental image of her on her knees with our loads all over her taut little tits still pops up in my mind from time to time.

Extra bonus would be the fact that they got married years later, and she had a tendency to be kind of a bitch, so being able to bust out a "remember when you let your now husband and I spitroast you?" would have been nice is some arguments.

 

[Britva415]

25 years ago I went on a camping trip with a couple I was close to, and, a young lady we were all friends with.

There was a meteor shower and we all laid out in a field in sleeping bags on tarps to watch. It was pretty great, and that night was when I first made out with the friend. At one point I heard our friends the couple wihspering to each other, "they're kissing!" They were happy for us for getting together.

And we did - the new girl and I were together a year later, and the four of us went to a convention and shared a hotel room with 2 queen beds. There was something about it, and I felt sexual tension in the atmosphere when we all were getting ready for bed, and hanging out in our beds with the lights still on before all going to sleep.

To this day I'm positive I wasn't imagining it, but nobody broke the ice. I'm convinced if someone had, all four of us would have enthusiastically had a four-way or at the very least some group sex with our own respective partners and all watching each other, us and the other couple.

 

[Up4fun&69]

Another time I still regret…
Back in college, I had the hots for this one classmate. But after freshmen year, she started dating (and later marrying) a rather boorish, possessive, upperclassman. We remained friends, but she still had my heart.
Well, one of her friends and dorm mate, a year older, showed some interest in me…lots of flirting, usually removed her bra before seeing me, etc. She wasn’t really my type but I kept hearing of all of her sexual exploits. My heartthrob even told me that her friend needed to breakaway from plain, vanilla sex and have her world rocked with something more than missionary sex.
Well, I was living off-campus in a studio apartment. I was at the usual Thirtsy Thursday party on campus and feeling no pain when this girl approached me and started complaining about the drinks. She talked and drank, and drank some more. She got really wasted, so I walked her back to her dorm. As I delivered her to the front door and am ready to drive myself back home, she grabbed my car keys, turned around, then turned around again and said, “You can’t leave until you find your keys.” She came up to me and started rubbing herself against me. As she was again braless, so I knew she had stuffed them in her panties. But two things stopped me. One, I was raised a gentleman and didn’t want to do anything rude or take advantage of a drunk woman. Two, I was afraid she’d tell my heartthrob what happened and any chance of getting her would be gone. So, after a 5-minute standoff, she put her hand in her jeans and pulled out my keys. She was upset I didn’t take her up on a free grope, but before I left, she invited herself over on Saturday to show me what a good margarita was.
Well, she did tell my heartthrob what happened. And I certainly gained some points with her. She then confided in me that her friend was planning on getting me drunk on Saturday and taking advantage of me…and winked.
Saturday night rolls around. She arrives dressed in jeans and a sexy, sheer top…braless, of course. She makes two of the strongest margaritas I’ve ever had—well, at least mine was strong. Over the next 20 minutes, 3 more margaritas, 2 slow dances, and 1 very hot, very long sensual kiss, she throws up her hands saying, “It’s true. You never get drunk and don’t just fool around,” and left. (Freshman year, I was voted BMOC, so my habits and likes were well known all over campus.) I sure had blue balls at that point, as her tits and her description of her wet, hairy bush and pussy had me turned on. But again, I was thinking more about my heartthrob than my throbbing cock.
Again, bonus points were earned as my heartthrob heard of my restraint. But in the end, they weren’t enough as her possessive boyfriend all but forbade her from seeing me again.
Fast forward 7 years after graduation… I moved back to L.A., near to where I went to college. I guess word spread and my margarita friend reached out to me. We talked a bit, I learned that she was engaged and the wedding was in one month, and we agreed to meet for drinks when she said that she needed some help. She showed up braless, of course, and confided in me that she wasn’t sure about her fiancé. He was mild and conservative, in and out of the bedroom. She said that she never experienced a really wild night of sex and so wanted to. She asked for advice but kept drinking and was getting plastered. At one point, she opened her blouse and then lifted her skirt to show me her mighty bush and wet, open pussy. I so wanted to plunge my face, fingers, and cock into it, but given our history and the fact that she was due to be married in just a few weeks, I couldn’t do it. (Damn my upbringing.) Later, she called, thanked me for the advice and thanked me for not taking advantage of her as she thought about things and was going ahead with the wedding. (38 years later, they’re still married.)
But I’d be lying if I said that I don’t kick myself for not taking advantage of any of those situations, and fantasizing about those tits, bush, and pussy which looked so very fine.

 

[lily_wall_]

I used to think sucking was the best thing sexually. I was stupid to refuse fucks just so I didn't have to stop sucking. I regret that. Even after making up for it in the years since, my pussy still reminds me of all those missed fucks

 

[secretthing]

When I was in college a few years ago, I shared a room with another girl. We got along pretty well and were a lot alike! We were both bisexual, both into video games, and we both had boyfriends at the time.

I would touch myself under the blankets in our shared room while she was home. A few times, she walked in on me while I was in the middle of masturbating. It was very embarrassing at the time, but she never called me out on it, and I never brought it up.

A few months into living together, I found a piece of paper she had accidentally left, and on that piece of paper there were several titles of porn videos that she had apparently been watching. Many of them were involving two female roommates fucking each other, or having threesomes with one of their boyfriends.

At the time I really didn't know what to make of it, but now I wonder if she wanted to have sex... I regret that I didn't realize that this was very likely until after I left college. She was really cute, too. I would've loved to fuck her while her boyfriend watched. I also have to wonder if maybe I wasn't as sneaky as I thought I was when I was fucking myself under the blankets, and maybe she knew exactly what I was doing? It would've been so hot to watch each other masturbate. Oh, I have so many regrets...

 

[Seeking4wife04]

Me and my step daughter have had a few tense moments but I've never acted on them and it depresses me.

Would you like to Google chat? I’m in line with my stepdaughter who is now in college. I could’ve fucked her when she was not a bitch, but I did not want to get in trouble now I think she’s ready.

 

[OtherwisePrint6210]

When I was in college a few years ago, I shared a room with another girl. We got along pretty well and were a lot alike! We were both bisexual, both into video games, and we both had boyfriends at the time.

I would touch myself under the blankets in our shared room while she was home. A few times, she walked in on me while I was in the middle of masturbating. It was very embarrassing at the time, but she never called me out on it, and I never brought it up.

A few months into living together, I found a piece of paper she had accidentally left, and on that piece of paper there were several titles of porn videos that she had apparently been watching. Many of them were involving two female roommates fucking each other, or having threesomes with one of their boyfriends.

At the time I really didn't know what to make of it, but now I wonder if she wanted to have sex... I regret that I didn't realize that this was very likely until after I left college. She was really cute, too. I would've loved to fuck her while her boyfriend watched. I also have to wonder if maybe I wasn't as sneaky as I thought I was when I was fucking myself under the blankets, and maybe she knew exactly what I was doing? It would've been so hot to watch each other masturbate. Oh, I have so many regrets...

Yep, lots of missed opportunities back in college!

 

[soflabbwlvr]

Regret is perhaps too strong of a word, but I do have a few situations I would handle differently if there were such things as do-overs.
In my third year of college my girlfriend and I were invited to a friend's house for dinner. All three of us went to high school together and attended the same university. At the last minute my girlfriend canceled, so I went alone. The friend, who I will refer to as Lisa, lived with her younger sister and baby. The sister, whom I had never met before, joined us for dinner. Lisa was average looking with a chubby figure and huge tits, but her younger sister was beautiful and had a smoking hot figure. She was also flirty, and I spent the entire evening enthralled by her. That is, until around 9:30 when she announced that she had to get up early for work, so she went to bed. That left me alone with Lisa. We talked and reminisced for another hour. Finally, I realized I had an early class and I still had to walk across campus to get home, so told Lisa it was time for me to leave. She held my hands and thanked me for coming over, looked into my eyes and said something to the effect of "I really don't want to be alone tonight." I knew exactly what she meant, but I got up anyway and told her I had to go. I made that decision not out of loyalty to my girlfriend (our relationship had already started the death spiral by that point), but because I was still hoping for a shot at the younger sister. I felt that fucking Lisa would ruin my chance of ever getting a shot with the younger woman. As it turns out, I never saw the sister again. And I never got another chance with Lisa. By the time I saw her again, she had a new boyfriend,and we drifted apart after that. We touched base occasionally for the next 10 years, but we were never in the same state together. So that is one situation I would definitely handle differently if it were possible.

 

[jackthelad11]

When I was 19 or 20 I started working as a bartender in a hotel. Late one night a couple who had a good few drinks started to get a bit loud and were arguing with each other.Eventually, the husband came up to the bar and apologised for all the noise, said his wife was very drunk and asked if someone would assist her in getting to their room in case she fell over while he finished his drink. My colleague who was much older than me said of course he would be happy to oblige. But then the husband said "I think it would be better if your friend there escorted her". Meaning me. So, off I go, trying to keep this woman upright and as we staggered to the elevator she started to explain the reason they were arguing was that her husband thought she had let herself go and didn't find her sexy anymore. In the elevator things got a bit messy as she pressed up against me, trying to kiss me and asking me if I thought she was sexy. Got her into their room and next thing I know is I'm lying on the bed with this woman all over me. As enjoyable as that was I was conscious that her husband was due to return within minutes.....so I managed to make a quick exit. When I got back to the bar the husband wasn't there and I'm thinking I had just dodged a bullet. But my colleague just looked horrified and asked "wtf are you doing here?".
Turns out, 2 or 3 times a year they had an arangement with my colleague where the wife "got drunk", he would escort her to their room and start to fuck her, and the husband would follow a few minutes later and watch them and masturbate. It seems the wife fancied a change.....me.....but nobody thought to tell me!!!!
I wish they had......lol

 

[write_or_wrong]

Mine would be the night I sat on the floor next to a woman at a house party. She and I had been talking, mostly non-sexy stuff, when another guy came along and started flirting with her. He was very forward and eventually asked her to give him a blowjob. Not one foot from my head, he stuck his cock in her mouth and they got into it. When he came, I could see his cock flexing and her cheeks pushing out. At that point, I should have asked her if we could snowball and share his cum (I love snowballs, creampies, etc.). But I didn't. I just sat there and watched her swallow two or three times until his load was in her tummy. A real missed opportunity.

 

[YourSecretDesires]

I've had a few. C'est la vie.

Years ago I had a female friend in town. We went to a party I was invited to - people I didn't really know. The party had a lot of women and they seemed to be out for blood. At one point when I went to get a beer in the kitchen, one woman cornered me and started touching me and suggesting we go back to her place uptown. I got an instant erection but had to tell her I was there with a friend and couldn't ditch her. This woman kept trying to convince me and then my friend walked in to the kitchen, saw what was happening and not wanting to interrupt, she said "I'll come back." But I used the interruption to break away and assure her I wasn't going to just leave her.

About that same friend, months earlier she got REALLY flirtatious with me and, at a different party, was jumping into my lap and just generally hugging and touching me. Thing is, she had gotten out of a relationship with a mutual guy friend and I didn't want to do that. Damn my scruples! So I resisted. It was hard though.

More recently, a female friend, mid to late 20s came over to my apartment a few years back. It was summer so I invited her for a swim in our pool. In the apartment after we changed into bathing suits, I asked her to put sunblock on my back and then I reciprocated. It was one of those moments where I was running my fingers along her backside and could have gotten more playful - but I didn't. (I think I had the hots for a mutual friend in that case so didn't want to start something.) I still sometimes fantasize about banging her even though she wasn't 100% my type.

 

[surrenderisfun]

I would have let some things go further with some guys who clearly didn't respect me in my early 20s. I was confused and ashamed how feeling aroused by being treated that way

 

[yowser]

There are some remarkable accounts here, that with a little elaboration, would make for terrific stories. If you've never published anything here (even if you have) I'd encourage you to share your story in greater detail.

 

[Deadfreak]

Too damn polite and respectful for my own good
Let too many pass by, stupid hindsight
Oh well, everything happens for a reason

 

[Erosfan]

A long time ago, I was dating a lady that was lots of fun. I was running late for a date with her and invited her to come to my house so we could just leave from there when I got ready. When she got there, I told her I was going to take a shower and I asked her to lay out clothes for me to wear. When I went to get dressed, there was nothing laid out for me. Well, the exhibitionist in me took over and I walked into my kitchen where she was on the phone with a friend. I'm fresh out of the shower, naked with a semi. She looks at me, gets off the phone and asks, what are you doing?. I reminded her that I had asked her to lay out something for me to wear and since there was nothing laid out, I figured this is how she wanted me to go out that night.
She got a huge grin on her face and said, you are crazy. She then picked up her purse, grabbed my arm and led me to the front door. I stopped just after she opened the door and backed out. I got dressed and we went dancing as we had planned. The next morning, we were having coffee, and I asked her what she would have done with her naked man, had I not chickened out. She grinned and said, I guess you'll never know. I never did get her to tell me what she was thinking that night.
I've never forgotten that night and I have always regretted not letting her take her naked man where ever she was going that night.

 

[KinkStevens]

Mine would be the night I sat on the floor next to a woman at a house party. She and I had been talking, mostly non-sexy stuff, when another guy came along and started flirting with her. He was very forward and eventually asked her to give him a blowjob. Not one foot from my head, he stuck his cock in her mouth and they got into it. When he came, I could see his cock flexing and her cheeks pushing out. At that point, I should have asked her if we could snowball and share his cum (I love snowballs, creampies, etc.). But I didn't. I just sat there and watched her swallow two or three times until his load was in her tummy. A real missed opportunity.

Thats sexy af despite the missed opportunity

 

[TemptationTango]

A girl who threw herself at me the day before she was moving out of town.

I played dumb and didn't pursue it because I knew she had a boyfriend.

Should have said "Fuck it!" and went for it.

Never ever turn it down if it is "thrown " at you. Might very well be the best you have ever had....gone in 60 seconds!

This is true for me right now...[me]late 60's and it's effing awesome!