Did you regret it or glad you did it ?

The first "official" time I experienced a complex blend of emotions, some positive, some negative. I was in the capacity of voyeur, the event was spontaneous, not planned. KK picked up a guy in the hotel bar, brought him up to our suite, gave me a brief chance to "say no," then the two of them fucked like bunnies, oblivious to my presence.

During the encounter, I experienced a simultaneous mix of nausea, regret, self-loathing, disgust, amazement, and off the chart lust - I experienced a spontaneous, hands-free orgasm/ejaculation while watching them suck and fuck each other's brains out. In the moment, the negatives gave way to lust, followed by "reclaiming" KK after the guy left.

The next few days and weeks were more complicated; recurring feelings of shame, regret, self-loathing, followed by lustful highs, looking to repeat the experience. Eventually the negative emotions dissipated, almost never returning.
 
The "why" part of the original post's question regarding feelings of regret is interesting to contemplate.

There are probably multiple dimensions, different for everyone about why feelings of regret surface in situations of non-monogamy, especially witnessing one's partner having sex with another person. There are "proper societal" expectations and norms broken as a consequence. It is also likely that we are all wired for a little possessiveness, jealousy, a sense of "ownership."

There is a bit of unavoidable humiliation involved, at least that was baked into some of my early experience. I was sitting by, witnessing my wife engaged in hot sex with another man, consenting to it - that is indeed a violation of the norm. Introspection, a bit of self-loathing that somehow I wasn't enough to sexually satisfy my wife, leading to that distinct feeling of regret.

The element of the finality of the act, knowing there was no turning back, no "unfucking" her once she'd taken another man's cock is an aspect of regret. I was fairly certain that after the first act I actually witnessed, that it was going to be something the old Lay's chip commercial, she "couldn't eat just one." Now I can't imagine life being different.
 
The "why" part of the original post's question regarding feelings of regret is interesting to contemplate.

There are probably multiple dimensions, different for everyone about why feelings of regret surface in situations of non-monogamy, especially witnessing one's partner having sex with another person. There are "proper societal" expectations and norms broken as a consequence. It is also likely that we are all wired for a little possessiveness, jealousy, a sense of "ownership."

There is a bit of unavoidable humiliation involved, at least that was baked into some of my early experience. I was sitting by, witnessing my wife engaged in hot sex with another man, consenting to it - that is indeed a violation of the norm. Introspection, a bit of self-loathing that somehow I wasn't enough to sexually satisfy my wife, leading to that distinct feeling of regret.

The element of the finality of the act, knowing there was no turning back, no "unfucking" her once she'd taken another man's cock is an aspect of regret. I was fairly certain that after the first act I actually witnessed, that it was going to be something the old Lay's chip commercial, she "couldn't eat just one." Now I can't imagine life being different.
What you write is so true. The angst, the acceptance, the compulsion.
 
She did not regret it. She's glad she did it. I'm still going through the angst of it all.
I’m in the same boat. we had talked about her having sex with someone and then she went to a wedding that I was unable to attend and an opportunity arose to have sex with a guy. I encouraged her to do it and she did. She told me he went down on her and then fucked her really fast, coming on her belly. It was so erotic knowing she might do this and then receiving a photo of her cum spattered belly. But since then she doesn’t tell me too much about it, says she is fine with what happened but thinks it’s boring now to go over it much. I have got increasingly frustrated with the whole lack of detail and it plays on my mind…
 
First time you shared your wife with another man to watch or even just for a threesome ! Do you regret it or are you glad you did and if your glad you did it why? And if you regretted it why?
So so glad the experience was out of this world....a sexual pleasure like no other.......from this moment onward l discovered what a slut she was and how much she wanted and needed plenty of dick.....bliss ❤
 
Was the most erotic thing ever" the leading up to it, all the pillow talk" then finally going through with it. He was a hung guy too" that's what we both wanted, wanted her to give herself to him totally. No condoms " was my only request, wanted her completely used, my first cream pie.. Clean up and then experienced the awesome feeling of her stretched sloppy pussy.
I found that following on.....my dick didn't touch the sides of her cunt and is cum was swirling all around my dick....it was an incredible sexual feeling....the best ever ❤
 
First time wasent planned at all. Friend did her over the back of the couch, 3 min start to end, he quickly left. Wife cried and apologized over and over. I was pissed about the whole thing. About 4 months later same guy same deal same outcome. Repeated 2 more times, was exciting the SHORT time it happened but after was not pleasant.
Wife and I came to grips and admitted it's fun. Gradually worked up to full on mfm with him. We're comfy together, we relax and enjoy the sexy fun. Done it I'd say close to 100 times over about 4 years. Same guy.
 
First time you shared your wife with another man to watch or even just for a threesome ! Do you regret it or are you glad you did and if your glad you did it why? And if you regretted it why?
Very glad. I admit the first time was a little hard. You think you are ready because you are so excited and turned on by the idea but the reality is different. As things got going I watched as my wife first suck on his cock then watched as she slowly lowered herself on to him and began to fuck. Seeing another mans cock disappear in my wife's pussy brought up feelings of jealousy and tested my ego. But I trusted my wife and as the evening wore on all of those feeling disappeared and were replaced with how thrilling sexually it all was. Never regretted that time or any of the others since then in over 20 years of marriage.
 
My only regret was not starting when we first got married. I'm kept pussyfree and in permanent chastity while my wife has lots of sex with her boyfriend. They have sex so much you would think they are teenagers. Even though I get to clean them up I'm not allowed to watch which I really want to do.
 
I remember being so jealous when I saw his cock in my wife's pussy. Hearing her moan and squeal. But then I was also so turned on at the same time. I soon began to realize that I was only making her happy by letting her enjoy other cocks. It was always a hot fantasy of hers. For 23 years I was the only man she had ever fucked. And when I would ask her if she would fuck another man while we were fucking, it always made her cum. I was the one who pushed her in that direction. I posted pics of her body with no face on a sex site. And she was bombarded by men offering to fuck her. When I showed her that she had very young men who wanted to fuck her, she became extremely interested. So I let her go meet one guy and he sucked. He lasted maybe two minutes. She fucked him in the back seat of her car. We met another guy who was younger than she was. Young enough to be her son. They both liked what they saw in each other and we met on a Friday in a cheap motel. And for two hours I watched him make a slut out of my wife. He came in her pussy twice that night. And after he left we fucked again. And she begged me that I let her fuck more men. She said she would fuck them in front of me. I always knew my wife was nasty. I made her nastier by letting her become my shared slut wife. We have no regrets. Over the course of 9 yrs, she was fucked about 250 times by 94 men.