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

[trecital]

Regrets, I've had a few, but then again, too few to mention......Hold on, I think that phrase had been used before by someone.....

[Threeisacharm]

I think a net benefit of understanding the regret is to act differently and to slow down. Last weekend a woman I was seeing occasionally was on Facebook so I sent a message asking her to come over. She told me she was actually with someone else. I asked her to come visit after her date which is something I would never have done.

[bham87uk]

Biggest regrets- whilst dating two different pakistani girls not pushing them into the lifestyle. I only started being interested myself a few years ago.

Girl 1- 21 years old at the time- I caught her messaging another guy. She could have been cheating on me as she hid her phone and didn't let me see the messages. I dumped her that night. I should have continued dating her and encouraged her fucking others.

Girl 2- horniest girl I ever met. She had been with a lot of guys. On first date she actually said "I really like you and I will let you fuck me in the ass". She even talked to me about how she as an escort could make £300 per hour. I should have encouraged her into this.. She would have been game I think for MMF, double vag, dp.

[sdave]

I think that the biggest regret I probably have is how things can change as you go along in this type of lifestyle. It's not always easy to turn back the clock and whilst it is often exciting at the time, it does change your relationship with your wife completely!

When we first began it was as a swinging couple. Sue was very shy and nervous. She was interested though. Our first being with an older couple. It was an eye opener watching a guy fuck Sue.

We tried our clubs and picked only couple nights. Sue and I got more and more relaxed with others. One night with single guys, she got talking to one and we jumped up to being open to her playing with a guy, initially as a threesome. Clubs after that changed. If we didn't match a couple which was quite often, then she would play with a guy. This became normal and she liked the attention. At our local club she eventually played with guys that were regular members and so developed regular fucks. This even led to her working occasionally in the bar at one club when they were short and playing with our/her friends too, I used to come along though. She messaged with guys she knew and many wanted more.

With both of us knowing the guys and her doing it regularly anyway, she asked to meet one of the guys alone when he asked he over. This seemed natural to us at this point and she would do this as a normal part of life. She would more actively swap contact details with guys and this developed into meeting guys for a drink and bringing them home. She liked guys that can accomomdate though.

I once wrote on here about her looking for guys and meeting someone from the gym and starting up with him. She was very comfy with everything by this point!

She is a very sexy lady and now our relationship is pretty much as open as it can get in terms of seeing others! She does focus on me alot and our relationship is still strong. But there are times she spends with others and with her meeting alone sometimes, she does develop her own relationships with others even if these are only for sex.

[tito123177]

Biggest regrets- whilst dating two different pakistani girls not pushing them into the lifestyle. I only started being interested myself a few years ago.

Girl 1- 21 years old at the time- I caught her messaging another guy. She could have been cheating on me as she hid her phone and didn't let me see the messages. I dumped her that night. I should have continued dating her and encouraged her fucking others.

Girl 2- horniest girl I ever met. She had been with a lot of guys. On first date she actually said "I really like you and I will let you fuck me in the ass". She even talked to me about how she as an escort could make £300 per hour. I should have encouraged her into this.. She would have been game I think for MMF, double vag, dp.

Had a similar issue with two of my ex, one she cheated on me, she fucked with another man, I dumped her, I should have stayed with her and encourage her to fuck with other man, I was young and inmature, she would have been the ideal hotwive.

With another ex, I told her my fantasy, after some months she agreeded to it, she wanted to fuck with a mature man, I was searching for him but we broke up for other reasons.

I hope my actual GF accepts to do it eventually...

[Beardedweirdo]

When we were much younger, together about 5 years, and aged 28, I had already spent a few years telling her my fantasy and she was on board thoeretically. I was planning a weekend away and she drunkenly told me "If you're going away this weekend I think I might find another man to have sex with." I was delighted when she said it. But when she saw me off at the train station I told her "I don't think I'm ready. There's a lot in we need to sort out, like my job, where we next live..." and she agreed we were not settled enough.

Looking back? What the fuck was I on about? Life things are life things. Sex is sex. I should have bought her a pack a pack of condoms, smacked her gently on her sweet behind and told her to go, have fun, and tell me all about it when I got home!

[simpforjada]

I wouldn't change a thing except bringing up the subject earlier.

This! I definitely regret that I was initially against it, and didn't trust that she knew what was best for us. Coming to terms with being her cuckold was emotionally challenging at first, I admit. But now that I've accepted it, embraced being her sissy, learned that my role is to support her in every way possible, I am so much happier than I was initially in our marriage. Allowing her to feminize me has been soooo much fun and open up ideas and doors to things I never even suspected about myself.

[jsaltydog]

Biggest regret: That my first wife and I did not honestly discuss and accept the cuckold lifestyle. She lied about cheating and I got angry when I found out. We should have embraced our sexuality. I should have been more accepting of my own desirers and hers. Had we been honest with each other and honest within ourselves, we could have enjoyed an incredible sex life and marriage. I'm sure that we would have explored all of the wild and kinky sex that I can only dream about in my older years.

[Johnann2227]

I have enjoyed 99.9% of our experiences both swinging and hotwifing. The only regrets were not vetoing a couple of Ann's boyfriends earlier as they were tools and didn't respect our marriage like they should have. I regret not saying no to her more as sometimes her play impacted negatively on family organisation etc. Nothing major though.

[SheLikesWhenIWatch]

Another "regret" that simply wasn't feasible at the time was for another man fuck her on our wedding night, and/or before the ceremony.

When I found out this was a thing, it blew my mind.

She started cucking me about 15 years after our wedding night.

At some point around then, I came across a cuck clip on PornHub (or wherever) that showed some dudes having their way with a young bride while the husband just sat in a corner and winced at his bride’s every moan.

I thought it was the hottest thing I could ever imagine…telling the world, “We’re a couple,” through a wedding ceremony and then enduring the psychological “punishment” of watching other men….friends and relatives (a brother?), in fact….fuck your newly minted bride to reinforce that you should not so confidently believe that her pussy is exclusively yours.

Yes, sex is about power! Husbands need to be cuckolded right away, on night #1, preferably by someone they will have to interact and associate with for the better part of their life (a brother? the best man?), preferably BEFORE they consummate the marriage with her, and most definitely while they watch and listen to their bride moan on another man’s dick.

My neighbor’s son got married a few years ago. At some point late in the reception, the bride, the groom, and three or four of their buddies (all young men, no girls) all disappeared for an hour or so to go to a room upstairs, in the hotel. The cuck that I am (and knowing, then, that wedding night cuckoldry is a thing), my imagination swirled at what might have been happening upstairs. Were they cucking the groom? I honestly wouldn’t put it past them. She was/is a wiley girl whom I’d known for several years beforehand. It would have been right out of her playbook……….When they returned to the reception, she was wearing “normal” clothes while all of the fellows were wearing the clothes they had been wearing all night. (At some point, she would have had to re-dress! Was it in front of these guys? Speculation!) My wife even laughed and said to me, “Well, I guess he [the groom] knows his place, now!” We cannot have been the only older, more experienced couple to have noticed. I’m sure wives were quietly commenting to their husbands.

In reality, they probably all went upstairs to smoke a little weed. It was just a coincidence that she was accompanied by a bunch of guys. Everyone already a bit tipsy from the mixed drinks, wine, and champagne… And when she changed clothes, she probably took her dress off and re-dressed in the bathroom.

Right?

I hope his brother fucked her really well!

[trecital]

I thought it was the hottest thing I could ever imagine…telling the world, “We’re a couple,” through a wedding ceremony and then enduring the psychological “punishment” of watching other men….friends and relatives (a brother?), in fact….fuck your newly minted bride to reinforce that you should not so confidently believe that her pussy is exclusively yours.

Hotter still if her pussy was actually to remain off limits to him completely

[jsaltydog]

I have had some great experiences. Some experiences i have posted about where great but I did not always fair so wel 8n 9thers and made huge mistakes with feelings of angst and looking back I have regrets. I also don't believe in labels. Any man that allows his wife or girlfriend to have sex with another man is a cuckold. That kink can be extreme with charity and humiliation or it can be as mild as two people who care for each other and have an open relationship. Hotwifing is a form of cuckolding with a majority of men posting that they like watching, hearing about or joining in sex with the person of their desire.

In my youth, I had wmw threesomes. My girlfriend at the time expressed interest an interest afterwards of having a threesome with another guy. I shut that down over jealous thoughts and one night she and a girlfriend went to a bar and they invited to black guys to her apartment. I showed up before anything happened but shut that down. Later, we went to her other friends house in a large city. While we were at the apartment and her friend was still at work, my girlfriend showed me her friends giant dildo that happened to be black. That night we attended a club that was mostly black and guys flirted with both of them. Nothing happened but when we got back to the friends apartment we were drunk and my girlfriend asked her friend to show me her massive black dildo. It escalated to giving us a show, followed by my girlfriend trying it, to both taking turns with it. I jerked off during the show and eventually joined in a threesome but could tell then that I made very little impact and in fact they both teased that they should have brought back the guys from the club as black guys (their words) had bigger cocks. I am 6.5 inches hard and a great lover but this was a hard pill to swallow but i did finish and then laying there pretending to sleep while they continued taking turns using the dildo while the other gave oral and hand help for orgasms until they both passed out. The next morning and drive back to our apartment we didn't talk about our adventure unlike the wmw adventures.

The next weekend, I was out of town for work and when I got home my girlfriend told me she went to visit her friend from the weekend before. I didn't ask for details, I broke up with her. I was hurt and selfish and wanted to be the wmw guy. About 12 years ago I started thinking about the experience and started to masterbate to what I should have done wishing I could go back. I fantasize about the first time she had someone over and being encouraging or the club we went to and what it meant to having showed me the big black dildo. Today me would have asked for them to invite guys over. I knew that her friend dated black guys. I would have loved to go back and explore that she was a size queen and that my girlfriend was very curious.

My girlfriend and I were in love but I was so repressed that I chose to take this as betrayal. I had the perfect partner for the feelings I have now. It could also be that this shaped my feelings now. Since that time, I have had many other experiences that I didn't allow and enjoy experiences or potential experiences making big mistakes.

I will continue to add to those regrets and wishes to go back and do it over again. I tried to be open in my last relationship to ask to experience this. We broke up and she is dating a black guy and as she texted me to ask how I was, let me know he was hung. It is not all about bbc for me but that has happened a few times.

Am I alone? How have you messed up in the road to being cucked or having a hotwife?

Wow, could have been a story about me and my first wife. I sympathize with you.

[jsaltydog]

So many regrets. Perhaps the biggest is with my first wife. She cheated on me from the start and I couldn't handle it. Our sex was always great, certainly the best sexual partner I ever had. The sad fact is that I always had fantasies about sharing my woman, doing clean up, and even sucking cock in the heat of a MWM or gang bang affair. Unfortunately, I was too stuck in the traditional family values stuff and the idea of monogamy. As for my wife, she was dishonest about cheating. Had I been honest and accepting of my true desires, and had she honestly told me that she needed sex with lots of guys, I think we could have reached an agreement that would have made both of our lives better. After our divorce, she got into crack and had sex to pay for dope. She and a girlfriend blew and entire college football team; in her own words, cum was everywhere. I get the impression that her then boyfriend was pimping her out, but I also know that she enjoyed sex to the fullest. Had we stayed together and accepted our desires, we could have both enjoyed cuckolding and wild affairs like gang bangs without turning her to prostitution and hard drugs.

As second regret happened years later with a GF. We were sexually compatible. I discussed swinging, sharing her, and sex clubs with her and she definitely was receptive. Unfortunately, she also got caught up with crack and ended up in jail. I moved while she was locked up and never saw her again. I hate drugs. Without drugs, she and I might still be together today and enjoying an open lifestyle.

One more regret. More than one GF asked about going to an adult book story, arcade or theater. I was hot for the idea, but they would usually say "not now, another time" even though they brought it up. I should have just taken them to one of those places. Probably could have shared them in a theater or at a glory hole.

[atl0707]

The biggest one I have is not encouraging my girlfriend more. She did make out with a black guy one night at the bar, but I was so distracted talking to other people that I couldn't enjoy the moment. The fact that she literally did it behind my back was a turn-on, though. Next month, we'll be going to a pool party, and I'd like to cut her loose to play. She's been resistant so far, but we'll see what happens. Once she sees the other women having fun with guys who are not their husbands, I think she'll realize what an opportunity she has.

[luvwives999]

I have no regrets on any of the things we did, my only regrets are opportunities missed. Either our not being aggressive enough, or just bad timing, there are a bunch of men she was willing and wanted, but for one reason or another it didn't happen to my and her dismay.

[AngiesHusband]

honestly I would go back and prevent some dark things that happened to Angie, but aside from that no I don't have regrets for the things we've done and experienced

[LongTermHubby]

My wife once said her only regret was not having started sooner.

[Hotwife2020]

When we first started cuckolding, I got mad at my wife for letting guys nut in her ass. She understood cuckolding right off the bat and let some strangers have a part of her I never did. I got insecure and angry when I found out. Huge fight and she has avoided anal ever since. Our communication had improved but I missed out on something for sure.

[cucking88]

Wish we had started really early in our relationship. She cheated on me for a couple of years before getting caught red handed. Really wish I knew I have always been a cuck. Missed watching her with at least 10 men during that period.