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

[Threeisacharm]

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?

[Cdncuck]

Everyone has made mistakes in anything they have done. That's how people learn and improve.

The same applies to hotwifing. We've made plenty of mistakes. Do I ever wish we hadn't gotten into this life? Hell no.

[mrdnrm]

Regrets hmmmmm

1. Not pursuing this lifestyle (Hotwife/Cuckold) earlier with my wife, but I guess having that stronger foundation prior to, has made this better for both of us. Having more confidence and more open honest conversation at the beginning could have eliminated a lot of jealousy, insecurity, and guilt earlier on in the lifestyle.

2. We had a chance for her to have a eight man gang bang (all BBC) I reduced it down to just three guys, I was worried they would have torn her apart. She handled all three men very well, just a good opportunity missed

3. We should have documented our journey better with notes, videos and more photos of each guy we spent time with. But we were worried family and friends would find out. But some have found out anyway.

4. Because of business we had this rule we would only meet people outside our sphere of influence and location. We missed out on a few good gentlemen that later we found out had the hots for the wife only after they found a steady woman or moved away. They said they had a feeling about us and would have loved to have been apart of our lifestyle.

Otherwise we love everything minutes of our current life of being a Hotwife and a Caged Cum Eating Cuckold Husband

[cthubby]

Would have been more forthright and encouragiing withher..starting much earlier in our marriage.

[submissivedanny]

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

[Chrislydi]

Two main regrets,

1) Not waiting to start this LS a lot later when we were more worldy wise and knowledgeable, possibly another decade.

2) Not knowing denial was such a turn off and would nearly break us, we now know how important the physical part including full penetrative sex is to us.

Chris

[Paulnlinda]

My 1st wife and I were married quite young and I had not quite got my head round some insecurities.
(Several years after our divorce my suspicions about her cheating proved correct!)

Late one evening her friend and 2 of his mates turned up, late and drunk. the atmosphere was very
sexually charged and at one point her 'friend' lost a bet and went upstairs to dress up in L's underwear.

They were gone for ages and when I crept up to the bedroom he was dressed in bra and stockings and she
jumped up guiltily from between his legs.

We had a guilty conversation which was perhaps the start of our breakup.
What I should have done is stripped her of her nightie, order back in and send the other 2 up, which she
had playfully suggested, and basically embraced the LS fully rather than let my insecurities get under my skin.

[canadianwittol]

In retrospect, while I would never have thought this just a few years ago, I do in fact have one major regret, which is not more fully diving into this earlier. If you search my username you will find posts dating back about ten years - I have been a cuckold for 13. Back when I first came online I was just looking to discuss cuckolding with other people because in fact I rarely ever spoke of it with my wife. She knew it turned me on, so she was simply having an affair with my blessing once a week. Basically I was aware, in theory, that I was a cuckold - a fact which turned me on, but I often didn't even know when my wife had seen her lover, as they usually got together during the workday at lunch.

Online was really my only outlet for discussing it any further. When I first came online, first at another now defunct forum, I assumed a lot of posts of cucks who had been "forcibly feminized" and so forth were all fake. I thought they must be complete fantasies out of the depraved minds of those who have a fetish for their own humiliation.

Well, after my wife's first affair ended, she found a new affair partner who was actually an experienced bull. At our first meeting he indicated that he wanted me to wear my wife's panties. I scoffed at the suggestion and absolutely refused to do it, for almost a year. This was a mistake for a number of reasons. First and primarily for the reason that I was standing in the path to my own participation and deeper enjoyment of our lifestyle. I was the one throwing up roadblocks by refusing to explore the sub space and be willing to play the submissive beta role for the bull. Of course, unlike in fictional accounts there was nothing he could "do" - but simply to exclude me from participating. We now had a bull who would be happy to have me sit and watch (something I'd never done before) but who wouldn't let me participate in my ultimate fantasy because I was not playing by his rules.

The second reason it was a mistake is that by refusing to do it for so long I only made my humiliation - and his victory over me - so much sweeter for him when I finally caved in. Looking back now, it seems inevitable that I would cave in, and there's a whole story associated to that as well - but finally I did. My wife had already been cuckolding me for 7 years before I finally watched her have sex with our bull. That was an amazing and unforgettable day, it's never gotten old for me but watching her that first time was like an out of body experience that can never be repeated. And to think I deferred it by a whole year of my life because I was too offended at the suggestion that I'd wear a pair of panties.

Over time, stockings and teddies were added - a Christmas came where our bull showed up with a "sexy Mrs. Clause" outfit for me to wear. The following Easter long weekend he showed up with a playboy bunny outfit for me. Every step of the way I protested but ultimately accepted each act of degradation.

My honest advice to my old self now would be that which I have finally adopted: accept that as the cuck you are the sub, and when presented with any opportunity to accept humiliation from the bull, do it. Without complaint. The sooner you dive in, the better it will be for you. He is part of the dynamic as well and if you happen to enter into a dynamic with a bull who wants to humiliate the cuckold, that need will have to be acknowledged if you want to continue your relationship with that bull.

I often think to an Oscar Wilde quote that "Everything in life is about sex, except for sex. Sex is about power." Cuckolding is about sex and is therefore about power. That first bull enjoyed the power dynamic - and why shouldn't he? Oddly enough, once I began to accept these kinds of humiliations I always felt rather silly - like - why was I so opposed to this? It's clothing. I'm the one that turned it into a hill I was willing to die on. Most people would feel totally humiliated by letting another man fuck their wife. Now that I will do happily - and yet I have a problem wearing something made out of pink lace material?

I was caught up in a firm belief that what our bull expected of me "wasn't fair." Why should I wear women's underwear because the guy who's fucking my wife says I have to? "It's not fair!" my internal monologue would repeat to me again and again. But we all know that life isn't fair. And while I would say that it's only a minority of bulls that insist on humiliating a cuckold, the reality is that many do and if you end up with one of those and you want to have a relationship with him you need to acknowledge his needs. There has always been a certain "sport" to cuckolding, even in the classical sense where getting one over on the (perhaps unknowing) cuckold is fun to a lot of "bulls" whether they use the term bull or not. I once asked our bull point blank what motivated him to make me wear panties and he answered simply and without any pretence: "It's fun to humiliate the cuckold." he elaborated that if he didn't get this component out of it, he might as well be just fucking some random woman.

Once I'd mentally got past some of these things, I could even admit that there's something that can be strangely relaxing about lounging around in lingerie. Now, since 2020, I wear panties every day. I don't even notice them anymore and I am blessed to own some very, very comfortable pairs.

So it turns out there was a whole year of 2016-1017 where I missed out on fun that I could have been having. It also turns out that not all of those forum posts were fictional after all - I am one of those "forcibly" feminized cucks - writing this from my office on a slow summer day while my co-workers are oblivious to the fact that I am wearing a bra and panties. I have also now met other cucks who I know for a fact are in the same position as me.

It's not about what's fair or what's right or anything like that - it's about playing your role when you're asked to play it. That's my regret: not playing my role in this power dynamic sooner.

[Chrislydi]

Not all cuckolds like or will accept additional humiliation, the simpler thing might be to tell the bull to clear off.

Chris

[canadianwittol]

That was sort of my point; by not initially being willing to accept additional humiliation I was getting in my own way. All three of us have been happier since I have. I guess to sum it up, my regret is that I wasn't more open to humiliation initially.

It's been a learning curve because I didn't like it either; it's been a challenge but I could honestly say now that it's been a challenge worth facing and that I regret not facing it sooner.

You may be of a different opinion, which is fine. That's just my regret.

[blind sided hubby]

I would have been more up front with my feelings about what I wanted. I know she wanted much more but because I was so silent she kept things under cover so to speak.

[turbulentdreams]

It's interesting to note that almost all of these regrets are regrets about things we didn't do, rather than things we did do.

[tito123177]

1.- When I was young I had a girlfriend from other city, she confessed she cheated on me, but only with kisses and touching with clothes on, I forgave her, but later I found out she fucked other guy and didn't tell me, I was angry but horny at the same time, I broke up with her, my regret is that if I had known about this lifestyle before and known how to handle my emotions I would actually accepted and explore more about her affair and do many things later.

2.- With another girlfriend I confessed my fantasy and after sometime she wanted to try it, she wanted to fuck a mature man, I was so excited, we talked about what would it be and the rules, but we broke up before we tried it because other reasons, my regret is that if I waited more about the problems we had, I would have had the opportunity to be a cuckold, even if we broke up after that.

I'm not a cuckold yet and I have a fiancé now, I hope someday she can cuckold me and explore this lifestyle at its fullest.

[aloneinmorrison]

My biggest regret thus far is selling out to “allowing” her to fuck her guys without me being present. When we first started having real talks about this, one of her biggest road blocks was that she didn’t know if she would be comfortable with me watching her with another man. At the time, I was just trying to squash her fears left and right and quickly told her I’d be okay with her going alone, as long as she came home right away so I could be with her afterwards. What was supposed to be a move to get her more comfortable with the whole thing has turned into her realizing that she enjoys going off and fucking other men without me being present. Had I been a little bit more patient in the beginning stages, I’d probably be watching and participating now instead of waiting for her to get home.

[iloanmywife]

I had so many missed opportunities when my wife and I were dating. Many of those were when we were in college, when my wife would frequently go out drinking with my friends and me. We'd find ourselves late into the night with lowered inhibitions, multiple men, me, and my wife. Sometimes they guys would get a little fresh with her, but we always played it off as friendly bantz and never took the bait. One of my good buddies were standing behind her at a bar, admiring her tight ass that was poured into a pair of stretch pants. The music was loud enough that she couldn't hear him telling me things like "That is a perfect fucking ass." I took the compliments in stride. Then he leaned over and point-blank asked me (verbatim), "Hey man, would you considering sharing?" I laughed and we went back to drinking.

One more than one occasion she and I had sex in a motel room with someone else in the room. Spring break, road trips, visits with friends. We never had much money and always shared a room with at least one other guy. And we were always horny, so we'd find some way to have sex. Sometimes it was brazenly going into the bathroom and fucking while a couple of guys played cards in the room. Other times we'd try to go back to the room early before others got to the room. And sometimes we just said "Fuck it" and had sex in the middle of the night or early morning with others in the room. One such time I was sharing a hotel room with the very same friend who had asked me about sharing her. It was the morning after a late night, and late enough that there was plenty of morning sunlight in the room. My wife and I had started to fool around as we woke up, masturbating each other and then slowly fucking under the covers. To make sure that my buddy in the other bed was still sound asleep I called out his name, loudly, several times. We were sure he was out cold. We started fucking harder, then she climbed on me, then we took off the covers and I was fucking my bottomless girlfriend doggy-style on the bed. I found out later from another friend that he had been watching us from underneath the covers, jacking off slowly. I don't know what would have happened if we would have seen him. We probably would have just let him watch.

One night my wife had a party at her college apartment. Some people had left, and several guys were snoozing and snoring in the living room. She and I wanted to have sex on her balcony, which was off of the living room. It was early morning, maybe 3AM, and there were probably half a dozen guys passed out on couches and on the floor. We snuck through the dark living room completely naked, then closed the glass balcony doors behind us, and I fucked her over the balcony rail. After we finished we walked quietly back through the living room, carefully stepping over a couple of my buddies. Turns out one of them woke up when we walked through the first time and he woke up two other guys and the three of them watched us fuck on the balcony, then played possum while we walked back through the living room. One guy told me later he was staring straight up at my wife's freshly fucked pussy when she stepped over his head.

When we talk about those times, my wife points out that it was too early in our relationship for us to handle sharing, and that fucking around with people we know would have caused problems. She is 100% right.

There were dozens of other missed opportunities along the way. Maybe "missed" is the wrong word. It wasn't so much that she or I didn't understand what was happening, but that we made a conscious decision that we weren't ready yet. And those baby steps along the way -- going out to a girls' night and fooling around with another man but not fucking him -- were exhilarating enough for both of us. It's unfair to say that it's a regret that she didn't fuck those guys back then, because we weren't ready.

Maybe one regret is that we never had a chance to play with another man or men while she was pregnant. Pregnant fucking is/was a bit of a fetish of mine. A MFM threesome with my pregnant wife, or watching her get gangbanged at 8-9 months, or even just watching another man fuck her with her big belly and leaking tits, would have been wild. Especially at those times when she'd get crazy horny -- more than I could handle -- and wanted it all the time.

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. I have a bride fetish as well, so I would loved to have watched another man have the honor that night. In reality it would have been impossible as our family and friends were with us from the moment we woke up to well into the morning hours. It was probably the best party I've ever been to, and I wouldn't change it for the world, so having a hotwife experience was out of the question. But I will say that we consummated our marriage while fantasizing about our cuckolding fetish (it was a breeding fantasy, actually). Since then we've had a couple of bride-themed adventures, one of which was particularly intense (see avatar). It's hard to say this a true regret, since a wedding day experience just wasn't going to happen.

Our biggest REAL REGRET is the time we wasted on guys who were fakes and leading us along or would get cold feet or were otherwise lying about one thing or another. We would have played with a lot more guys if it wasn't for the churn of losers and fakers throughout the years.

[Long Lurker 34]

My biggest regret thus far is selling out to “allowing” her to fuck her guys without me being present. When we first started having real talks about this, one of her biggest road blocks was that she didn’t know if she would be comfortable with me watching her with another man. At the time, I was just trying to squash her fears left and right and quickly told her I’d be okay with her going alone, as long as she came home right away so I could be with her afterwards. What was supposed to be a move to get her more comfortable with the whole thing has turned into her realizing that she enjoys going off and fucking other men without me being present. Had I been a little bit more patient in the beginning stages, I’d probably be watching and participating now instead of waiting for her to get home.

AIM - What about her taking some videos for you?
Does she at least tell you how things went down, in a timely manner?

[tractorman2]

I cannot say these are really regrets as we were different people when younger although the blue print for our relationship was set early in our friendship, she was 16 and i was 21/22. We acknowledged later that even then we were always destined to enter this LS even though we didnt know what this was,

Unknown to me she was already practicing it, she happy to have me as her boyfriend, later her husband but then getting drunk and snogging and been fondled by other men at nightclubs this didnt count as cheating in her mind. Neither did kissing a man as she stood up whilst he fingered her to such a degree that she could no longer stand, wasnt cheating either.

Her later stated view that even as we married i probably was always going to be her cuck husband, not because of my size but my sexual experience turned out to be true.

So if i could turn the clock back,

I wish i had been married at least wearing a pair of her knickers, though we werent yet ready for that,

A man she had flirted with by then in his late 30s who had tasted my girlfriends young breasts when she was 16 before she bottled it, was still chasing her, should he have been invited to our wedding and been the first cock she took as a married women?. Talking later i suggested my acceptance percentage then would probably been about 30% hers was higher as we have discussed at 75%, morality was the big bloker.

(He was still chasing her when she was 19 and obviously pregnant and still wanted to fuck her whilst she carried our child).

Neither did we know that we were both sexually submissives, at about 21 she was having an affair with her driving instructor she sought to hide from me but by the time she was in her mid 20s she was having an affair with my best friend which she wanted me to know about, sure i would accept this, guided by his chats with me. He turned me unknowingly into a cuck, jointly confirming my conversion as they fucked infront of me.

Had i not been so nieve even then and after a the conversion we had a couple of years later where she admitted her cheating past in detail, everything we later went on to do could have been done probably 10 or 15 years sooner, but such is life.

Throughout her late teens and 20s she played the part of an absolutely loyal and vaniilla wife even she convinced me, but time has shown that her kinky naughty mind was a lot more advanced than mine, i was the straight alpha male and the dominant one in this family as she wanted in her husband, but with a 100% vanilla wife, but still she turned me into accepting i was a cuck husband.

Likewise by the time my kinks arrived in my mind after that conversion, i drove this now, sourcing long term lovers for her as she wanted me to do then, so i would be involved in some way.

In her 30s my kinky mind came up with a major kink, selling her as an escort, she agreed rather reluctantly however then went through with this, by this time we didnt need the money this was pure kink for us both. We agreed it would happen only a few times but the cash rolled in, a shame i didnt consider this when she was in her 20s and we needed the money, in reality she wouldnt have gone mental then if i had suggested this. I still think back to this time and gain hugh pleasure in having done this. A lot of the time it was older men who wanted the company of a fit women it wasnt always about sex for them. We stopped as agreed at the beginning of this adventure.

Later she commenced semi feminizing me, with my consent turning me into a mix of loving cuck husband and a sister to her.

I also wish she had taken a dominant lover, a man who semi dominated me as well as her but again as a 6ft 3 strong fit man with a strong alpha dominant personality i suspect few would have dared try. I had to wait till my late 40s for this.

Then again in reality, relationship wise we have been down a long road, with many junctions and had one of us turned off and the other carried on none of this would have happened anyway.

[aloneinmorrison]

My biggest regret thus far is selling out to “allowing” her to fuck her guys without me being present. When we first started having real talks about this, one of her biggest road blocks was that she didn’t know if she would be comfortable with me watching her with another man. At the time, I was just trying to squash her fears left and right and quickly told her I’d be okay with her going alone, as long as she came home right away so I could be with her afterwards. What was supposed to be a move to get her more comfortable with the whole thing has turned into her realizing that she enjoys going off and fucking other men without me being present. Had I been a little bit more patient in the beginning stages, I’d probably be watching and participating now instead of waiting for her to get home.

AIM - What about her taking some videos for you?
Does she at least tell you how things went down, in a timely manner?

Yes. She has taken pictures and videos. Don’t get me wrong. It’s not like I’m locked out of the process. She fucks them and immediately comes home and tells me all about her date while I suck his cum out of her pussy. We usually fuck twice afterwards.

[Long Lurker 34]

AIM - Ok good to know. I've read too many times here, where the husband from the way the posts are written appear to be sort of isolated? when the wife does not let on what transpired during a meet up/date.

Good luck on your journey.

[iloanmywife]

My biggest regret thus far is selling out to “allowing” her to fuck her guys without me being present. When we first started having real talks about this, one of her biggest road blocks was that she didn’t know if she would be comfortable with me watching her with another man. At the time, I was just trying to squash her fears left and right and quickly told her I’d be okay with her going alone, as long as she came home right away so I could be with her afterwards. What was supposed to be a move to get her more comfortable with the whole thing has turned into her realizing that she enjoys going off and fucking other men without me being present. Had I been a little bit more patient in the beginning stages, I’d probably be watching and participating now instead of waiting for her to get home.

AIM - What about her taking some videos for you?
Does she at least tell you how things went down, in a timely manner?

Yes. She has taken pictures and videos. Don’t get me wrong. It’s not like I’m locked out of the process. She fucks them and immediately comes home and tells me all about her date while I suck his cum out of her pussy. We usually fuck twice afterwards.

Rough story, but not uncommon. I've been down this road as well. A wife can get more action without having to coordinate her husband's involvement. At least for my wife, it was easier to be comfortable and get off when it was one-on-one in private. The sex feels more intimate and natural, which can make for a hot dynamic. But with that sort of play it's easy for the husband to feel left out. For some cuckold masochists that's actually part of the fun. But generally I think anyone feeling left out is a major problem and a recipe for resentment.

I don't know the word for the opposite of regret, but that's what I feel about every single picture and video that I have from our adventures, whether I was present at the time or not. I cherish them all, even the terrible ones. I have a picture of a messed up hotel bed that she texted me in the middle of one of her dates. That's all I got from her that night, and I saved it. I've actually masturbated to that pic, as pitiful as that sounds. It should have the caption, "Some guy fucked my wife and all I got was this picture of a hotel bed."

The dearth of material from her private playtime is a bit of a regret. I'm thankful for the few I received, most of which made my heart skip when I opened them. Closeups of her dripping creampies, anonymous cocks in her mouth, a mind-blowing POV facial video. Relative to how many times she's fucked other guys, I have precious few pics and vids, but those few are now treasured keepsakes. I'm not promising that I'd run into a burning house to save them, but I'd definitely assess the fire before making a decision. Bottom line, if pics and vids are important to a husband whose wife plays alone, they both need to agree that this is part of the deal.

Had I been a little bit more patient in the beginning stages, I’d probably be watching and participating now instead of waiting for her to get home.

So do you ever get to watch? That should definitely be your next milestone if you haven't done that already.

She fucks them and immediately comes home and tells me all about her date while I suck his cum out of her pussy. We usually fuck twice afterwards.

Most wannabe cuckolds on this forum are already insanely jealous of your relationship as it stands. From their point of view, you and your wife are living their fantasy life!

[bjgirl]

The best missed opportunity was our first foray into this lifestyle. We were quite young and inexperienced and were just role playing scenarios of her fucking other guys. Often during these role play sessions, she would mention a coworker of hers she found attractive and admitted they flirted at work quite often. One night she had a work function to attend and he gave her a ride home as she had been drinking a lot.
The next day I came home from work and after a lot of tears and stops and starts in her confession, it came out that he "unexpectedly" showed up at lunch at our house (she was off for the day) and she gave him a blow job.
We / I wasn't ready for our role play to become real but it was now. We had a rough patch for a few weeks but eventually discussed things and decided we wanted to pursue the lifestyle but we set ground rules.
Unfortunately, he moved away before my wife and I hammered out our "rules" for playing and she never did anything else with him. According to her, he had the THICKEST cock she had ever seen, even up to now! It was so thick she said her mouth ached for hours after blowing him! I would have LOVED to see it stretch her pussy.

[iloanmywife]

The best missed opportunity was our first foray into this lifestyle. We were quite young and inexperienced and were just role playing scenarios of her fucking other guys. Often during these role play sessions, she would mention a coworker of hers she found attractive and admitted they flirted at work quite often. One night she had a work function to attend and he gave her a ride home as she had been drinking a lot.
The next day I came home from work and after a lot of tears and stops and starts in her confession, it came out that he "unexpectedly" showed up at lunch at our house (she was off for the day) and she gave him a blow job.
We / I wasn't ready for our role play to become real but it was now. We had a rough patch for a few weeks but eventually discussed things and decided we wanted to pursue the lifestyle but we set ground rules.
Unfortunately, he moved away before my wife and I hammered out our "rules" for playing and she never did anything else with him. According to her, he had the THICKEST cock she had ever seen, even up to now! It was so thick she said her mouth ached for hours after blowing him! I would have LOVED to see it stretch her pussy.

That's a really hot story. Thanks for sharing. Those sort of younger indiscretions are hotter in some ways than more "advanced" swinging, because it wasn't scripted. Your girlfriend really did suck some guy's thick cock behind your back! I hope that you and she have made good use of that experience as fantasy material.

Do you think it would have caused too much damage to your early relationship if he had actually fucked her that day? Maybe it was for the best that it didn't go any further. Or...just a thought...is it possible that it really did go further? That they had sex but your then-girlfriend confessed to blowing him to cover her tracks if you somehow found out? It's sometimes easier to confess to a less-severe infidelity to get the benefit of confessing without having to give the full details.

One time when I was deployed my then-girlfriend-now-wife was at an apartment party and went off to a bedroom for a few hours with another guy. She confessed as soon as I got home because she knew that it would get back to me. This guy was also in the service and in our extended network of friends-of-friends, so I was pissed that she had played with fire like that. She insisted that she was "just making out on the bed" until she fell asleep. A good buddy of mine (who knew someone who was at the party) pointed out that adults don't just make out on a bed for a couple of hours in a locked bedroom. Who knows? I'm pretty sure she didn't fuck him, but I'll probably never know for sure and I don't mind. Unless she reads this post and wants to tell me more, it will forever be part of the mystery that turns me on so much.

[vmb69]

If I could go back in time, I would make sure to control my jealousy at the time and not let it control me, it would have made things so much better. I guess it's all part of growing up in this lifestyle

[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.

[iloanmywife]

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.