Cuckold regrets ...if you could go back in time

[desertsub]

I would have to say that my biggest regret was how I handled things when I caught my wife with another guy before we got married. She knew my first wife had cuckolded me and I liked it. We were living together and she had gone clubbing one night with her girlfriends. I was working and was okay with it. She didn't get home after the bars closed and I went looking for her and found her at one of her friend's apartment with another guy. I got mad and moved out and she continued to fuck him for about two months. The thing is though, during that two months I masturbated pretty much every night thinking about her and him together. When she got tired of him she wanted me back and I knew that even though she would probably do it again I eagerly took her back and we got married just a couple of months later.

She did start cuckolding me about two years later, again going clubbing with her girlfriends and usually fucking someone before returning home. Looking back, I'm sure that if I had accepted her being with that guy that night she would have continued to cuckold me right through us getting married and afterwards. I feel that 2 years were wasted because of my actions that night.

Hot, painful story. Thanks for sharing. Being cuckolded, even for those of us who developed a taste for it, is hard medicine to swallow.

The hard part was that she did it behind my back. After I moved out I realized that I was the first guy she had been with that accepted that she liked to fuck different guys and was okay being cuckolded. She probably assumed that she could tell me later and I would be okay with it. We had not really talked about her cuckolding me and I still feel like it was on me that it happened that way.

When she did start openly cuckolding me it was not until we had gone on an overnight motorcycle trip. We stayed in a cabin with no TV and we spent the evening talking about our fantasies and fetishes. A lot of things changed after that night.

[bjgirl]

iloanmywife - interesting questions.
I have often wondered and fantasized about "if" she fucked him. I think, given our relationship, it would have survived if she did actually have sex with him and not just a blow job. We enjoy the lifestyle now and back then still role played using "him" - we just had to get over that first sped bump.
I do wonder and have asked her many times in the past if anything more happened but to this day she still says it was only a blow job - a blow job which included her first time ever swallowing! Also, for weeks afterwards she complained of a pain at / near her cervix whenever she was on top during sex - and this was totally new. That of course made me wonder but she said it was only coincidence.

[iloanmywife]

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I do wonder and have asked her many times in the past if anything more happened but to this day she still says it was only a blow job - a blow job which included her first time ever swallowing!

Crazy hot. I’m sure that must have enraged you back then and really turns you on now. Like you, my wife first swallowed with other men. Her doing that with other men but not you feels almost mean-spirited.

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Also, for weeks afterwards she complained of a pain at / near her cervix whenever she was on top during sex - and this was totally new. That of course made me wonder but she said it was only coincidence.

I distrust coincidences. In your situation I’d accept that she very well might have fucked him and that I’ll never know for sure. If not knowing for sure doesn’t bother you it can add an intriguing layer of sexual mystery to your relationship

[bjgirl]

Crazy hot. I’m sure that must have enraged you back then and really turns you on now. Like you, my wife first swallowed with other men. Her doing that with other men but not you feels almost mean-spirited.
I don't feel it is mean spirited that she doesn't swallow for me. He had a COCK, I have a dick (her words) and she just felt it was a sign of respect to swallow for him because of his size. Every COCK she has sucked since then she has swallowed for and I feel the same as her - they deserve to because of their size - it just excites her more.

Also, for weeks afterwards she complained of a pain at / near her cervix whenever she was on top during sex - and this was totally new. That of course made me wonder but she said it was only coincidence.
I have to agree - huge coincidence but to this day she still says it was only a blow job and has had a several BBC lovers since and knows I'm totally fine with it if she did have sex with him.

[Threeisacharm]

My 1st wife and I started swinging. First night we ended up at a large house party. We cracked the swinging with the couple that brought us. The wife was on her period and the husband fucked Alex while I held her hand. We then somehow got separated for an hour or so and she fucked the owner of the house in his bed. I now regret that we didn't stay in that mode where it was a couple thing. We dove right in and were together but seperate and open.

I would like to update this story but a year in, Alex asked fora threesome. She told me she had two choices and one was bi sexual. I asked for the straight one. The short version is that we met for drinks in the hotel we booked and he mentioned he lived with a gay roommate, but I didn't engage in that conversation. I am now sure he was the bi one. As we went upstairs, Alex asked me to get ice and let them get started.

I came back in and they were already fucking. I watched and at some point fucked her and came in Alex. Ben, watched and laid there with his big cock jerking. After I came he slid back in and fucked her for the next hour . I had recovered and while he was behind her I was beside and got oral. He was looking at my cock but I froze and at the time...big regret.

I traveled internationally for work and the next weekend I called home and she didn't answer. The next day we spoke and she immediately admitted that she went to visit Ben. I told her that wasn't cool and said we needed to let each other know where we were. She said it wouldn't happen again.

How I regret that now. I now only think of MMF and she was the perfect hotwife. I should have asked for details and supported her. I also should have talked about my suppressed bi feelings and enjoyed that. After admission, I should have asked her to have him back and asked them both for details and had the real experience.

[sub_hubby_larry]

My biggest regret has been revealed through the pandemic and at times has made me wish I had never asked if she wanted to start the lifestyle. During the pandemic my wife's semi-long term partner eventually became unavailable and so she had no one else. I tried my best to step in and pleasure her but was never really able to. We had sober conversations about things that turned her on, how I could initiate better, etc. and I tried everything. I usually can give her an orgasm or two during foreplay but not the mind blowing things I've seen her have with other men. While my lack of ability to please her like other men is a large part of my side of the fetish, it went from fun humiliation to frustrating sadness watching her libido shrink despite my best efforts.

However, there is a silver lining (maybe) that she has once again, after 2.5 years found another partner that she really enjoys and I'm finally seeing her libido return and seeing all of the small things I've missed (the look on her face before/after she's with him, the extra care in getting ready, etc.). I mentioned to her one day that I noticed all of those things and asked now if there was anything in particular that made it so much better with him (besides size and stamina) versus the time when I was trying to be enough. She said no, it really seemed like he basically did the same things. I asked if she had any idea why it was different and her answer simultaneously gutted me (in context of the possibility of her not having a bull in the future) and got me rock hard. She said that she's just not turned on by me any more. That over time the humiliation and things changed something in her bodily reaction to me that she just doesn't have that initial arousal. With him she does so even before they are kissing, even on the ride to go see him, she's already wet and full of butterflies. With me, while she appreciated my attempts, and still loves me as a life partner/husband, she had to put in effort to try to feel in the mood, which didn't really work anymore because I was just "not for sex".

So, that is supremely hot, but also potentially my biggest regret if ever she cannot find a bull in the future, because I know I can not satisfy her (even though hearing that has redoubled my efforts to try when the opportunity arises!). If there's ever a long stretch again I'll know she is sexually frustrated and it's all my fault.

[Filou]

"Looking back in retrospect and regretting your past, you miss the opportunities in front of you."

A quote that makes sense in my opinion.
You can not change the past - only the future. So look forward having learned from the past. Make sure though you do not take too much balast from your past with you. Maybe it was even the right choice to break up and you might have missed other opportunities if you have stayed in that relationship.
Apart from that: Overstraining your partber is not the smartest thing to do in a relationship...

[LongTermHubby]

My wife told me she regretted not starting sooner.

[Threeisacharm]

Another memory of Alex (she) came up. I came home early and she admitted she invited a guy over. He showed up and they fucked infront of me but he came pretty fast and left. I fucked her for the next hour.

Again it was another case where I could have gotten away from couples swap and the regret is that I didn't know I would only want threesomes with one women, two men.

[dinoo]

Not being aware of the fact or discovered to late that my wife had many more perverted thoughts than I could imagine.

[Gazmo]

Actually, my regret is that I tried my hardest to introduce C to my kink as gradually as humanly possible - a while ago she said "Why didn't you tell me about this at the beginning of our relationship?".

Hmmmmm...

[desertsub]

Actually, my regret is that I tried my hardest to introduce C to my kink as gradually as humanly possible - a while ago she said "Why didn't you tell me about this at the beginning of our relationship?".

Hmmmmm...

That could go one of two ways! She could be feeling that a lot of time has been wasted or she might be thinking that if she had known how kinky you are she might not have married you!

[Gazmo]

Actually, my regret is that I tried my hardest to introduce C to my kink as gradually as humanly possible - a while ago she said "Why didn't you tell me about this at the beginning of our relationship?".

Hmmmmm...

That could go one of two ways! She could be feeling that a lot of time has been wasted or she might be thinking that if she had known how kinky you are she might not have married you!

She is European, from a very liberal country in terms of sexuality (Germany)... but you may indeed be correct there DS!

Maybe things have turned out just the way they should have

[JaBe]

Regrets? Just the one. Recriminations, argument and jumping to conclusion over a bad case of thrush that infected us both.

[wisebetrue]

My Wife of 28 years passed away in April, I have thought about this question and cannot think of a regret on my part.... The quick back story of her turning me into a sub cuck was her doing, She was caught by me several times over the years getting side dick, I always stayed quite about it so as to figure out who it was but eventually let it out in arguments, She was a denier, So many times I found loads in her Panties, I gradually accepted it and would always go for giving her oral when she returned from Work which was her "Fuck time" I figured out...I guess I liked the humiliation..

What went through her head I do not know, But gradually over the years I think she liked the power over me, and eventually Mildly feminized me for the last 8 years, during the last 8 years We had separate bedrooms but were like best friends, Our sex life consisted of me in a house dress on my knees giving her head to climax, she finished with a thank you and a hug but no touching me or sex for me... I also think she lost respect for me years ago when I begged her to come back home after she left for a 3 month fling with a ex....after that she fucked several behind my back and I think I caught most of them...

I hinted best I could about I liked it, and I think that was a problem for her, she did not like me liking it or even knowing, I think she was a covert narcissist, One time I eventfully got something out of her when I asked years later about the ex affair and why she did it her answer was " I guess I wanted some strange" Now let me tell you all something, she NEVER would discuss anything with me bout her affairs. And would get livid when I told her about when and who, I was a very good detective!

The affairs turned me on, I accepted my fate and my hand for the last 8 years...Anyone know how I could have done this differently? I tried my best to be a part of her lifestyle.... what could I have done differently?

[Cuck4Life]

My exwife Louise screwed many of my friends and coworkers during the 70's and I have no regrets. She was sexually active when I meet her and I never asked her to slowdown. Our relationship was open and known to may. I know the guys talked about screwing her and I now wish I could have heard some of those conversations. Everyone knew I was the guy who's wife fucked around.

I never thought about doing cleanup, maybe it would have been crossing the line in those days. I think about that now and wonder how it would have been to be known as the guy whos wife fucks around and would lick cum your from her pussy. These guys were coworkers and friends so it would have added a extra touch to our relationship.

[cantbelieve]

So many regrets, I couldn't count them all. But one that comes to mind and is probably the biggest, was with my 1st wife. I married her young. She was only 20 and I 26. We got along great together and the sex was wonderful. We never fought until I discovered she was seeing her ex boyfriend, (the one I stole her away from) on the side. I was hurt mostly by the lies and the hiding it from me. I never told her that it sometimes turned me on thinking about her being with him.
For a long while, she would only let me do her anally (she really got off on anal), which was my favorite but I had this idea that she was letting him fuck her pussy while only allowing me her butt. Again, I was still hurt about the lies.
We moved a couple of states away from our families and her ex boyfriend after a couple of years of marriage. This brought a bit of a rough time as she was homesick. She eventually got over it after she secured a good job and made a friend in a divorced woman co worker. Now, she worked a day shift and I worked a night shift. So, she was hanging out with this divorcee nights and weekends while I was working or just staying home. My partying days were over. We still were having fights about her going out as I knew she was fooling around picking up guys at the clubs. This was putting a wedge between us and she eventually asked for a divorce and I amicably granted it. We just both went our separate ways.
But now, looking back on it, if I had just accepted and let her know my feelings of how it turned me on, we probably could have really enjoyed the hotwife lifestyle and had a great life together.

[cantbelieve]

A side story about my ex. After we separated, she moved in with that co worker to share expenses and I moved to a small apartment. Shortly after the divorce was final, she called me up out of the blue and just asked if she could come over. I was already super lonely so I agreed. She came over and we talked for maybe 15 minutes telling each other how work was going or some other cordial talk when she just came out and said she wanted to have sex. Obviously I agree without hesitation. When I started to try put it in her pussy she flat out said "no, in my butt" and turned around for me. She pulled a small bottle of lube out of her purse and I applied it in her and on myself like I had done many time and slowly inserted it in her ass.
Now, when we ever had anal sex, it was always very slow and time consuming to get fully penetrated. Nothing was forced or done quickly. This time was special time for me as I loved the cuddling portion of it. Sometimes it may have taken 20 minutes of gently working insider her.

[cantbelieve]

Holding her while she relaxed to accept me, fondling her breasts and nuzzling the back of her neck was special. I always knew my size was a bit small and probably not ideal for vaginal sex but I knew I was a perfect size for anal. Not too big to be uncomfortable or painful, if we went slow and gently but not so small that it wouldn't be filling. Once I was bottomed out, she would start moving against me and we would build up speed and force. She would be working her clit with her right hand and also building up speed and force with that. I mean, her arm moving be moving up and down on her self almost violently. Then, when it was her time, she would tilt her head back with her eyes shut, open her mouth wide as if too howl out but, she wouldn't make a sound, until she finished and she would collapse down to the floor.
After we finished we got dressed and she just said she had to go. She gave me a quick kiss and a "thanks" and "see ya later" and off she went.
It wasn't the first time I felt used for sex by a woman but it was the first time she made me feel it.
We never saw each other again until my fathers funeral. I was surprised when she showed up. We were both still single and I felt she was there for more than to give her condolences. One look at her and my feelings for her rushed in. But, I didn't act. My pride got in my way and I wanted her to make the first gesture. She didn't and our history together ended right there. I've never seen or heard from her since.

[spritztiger]

This story really sounds very sad

[JaBe]

Not really a regret, but more wondering if the aftermath of EsBe's first playing away and fucking another guy could have turned out so that she wanted to go again.

[Threeisacharm]

I just broke up with a woman I was seeing. I got the feeling I was a bull. We were fooling around and rather than have regrets I asked her about her friend she always mentions and she admitted they were dating. I asked if he knew we were intimate and she admitted that he wanted her to date and report back. I convinced her to call him and let him listen without talking to him and she did.

Odd that after that, we went out seperate ways.

[vmb69]

I just broke up with a woman I was seeing. I got the feeling I was a bull. We were fooling around and rather than have regrets I asked her about her friend she always mentions and she admitted they were dating. I asked if he knew we were intimate and she admitted that he wanted her to date and report back. I convinced her to call him and let him listen without talking to him and she did.

Odd that after that, we went out seperate ways.

You took the secret out, he probably enjoyed it but only as far as no one was aware.

[isinlarsa]

My biggest regret is about my wife's first time with her young black "studmuffin" (her nickname for him). He was a recently-graduated major college basketball player, almost half her age, who she had met online. She had been dating him for some time but they hadn't consummated their sexual relationship. Finally, one Sunday night, she told me she was going to "accommodate him" the next Wednesday night at our house. She asked me to take our young daughter out for the evening so she could entertain him. So I knew several days in advance that this young black stud was going to fuck my wife, in our house, in our bedroom, in our marital bed!

My mind went wild with possibilities of setting up a hidden camera, or at least a hidden recording device to record their first tryst. Although I researched all sort of recording devises, I eventually decided I shouldn't invade their privacy. Although I know that was the right decision, I still have regrets after all these years.

[Wannashare34135]

1) when we were dating a few guys I worked with told me that if I ever needed any help with her, they’d be happy to oblige. I bristled at them at the time but would love to go back in time and embrace the idea more, tell them about her sexually, etc
2) at my brothers wedding, an older man there seemed to sense my inner cuck nature and asked me if he could dance with my wife. He said things like look at her, she wants to dance, she just needs some encouragement, let me do it. I’m sure nothing would’ve happened but man I’d love to relive that today.
3) at my own wedding, at the reception hall, a couple of black guys congratulated me in the restroom, talking about how hot and beautiful my wife was. Again, wish I had engaged them in hot talk!