A Threesome I'll Forever Regret

Preface: I wrote this story because I have searched far and wide for cuckolding stories where the cuckolding happens both accidentally/or in the heat of the moment, and leaves the man feeling a permanent sense of regret (without any sexual satisfaction for him). After being unable to find something like this over the years, I decided to write on for myself. Enjoy! BTW, If you happen to know of stories like the ones I'm looking for, please let me know in the comments!

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My wife Genny and I have been married for several years, but I did something recently I strongly regretted and it has been making me absolutely sick inside. I can't stop thinking about it, and the consequences it has caused. I feel like so much less of a man, and it's all my fault for going along with it.

Okay... so details. My wife and I have been married for 7 years now. She was absolutely drop dead gorgeous when I met her, and still is to this day. She's a tall brunette with super skinny legs, a really round (but not too big bottom), and really perky (but average or below average sized) breasts. She had average sized areolas, but her pussy was one of her best features. She always kept her pubic hair neatly groomed. She waxed almost her entire pubic area except for a three inch long, one-inch wide landing strip above her vulva. And she is hairy too, so it definitely was a nice bush. Her outer labia were a darker tan color and really contrasted well with her milky white skin. Her inner labia were large, as I prefer, and peeked out from her outer labia like delicious meat curtains. They're somewhat open too around her vaginal area, so you can clearly see her beautiful pink closed pussy hole, even when she's not turned on. When she turns herself on, her clitoris becomes enormous (sticks out almost a full centimeter), and her labia puffs up. It's practically museum quality. Enough for me to go on and on about it :D

When she is wearing just a t-shirt, knowing I was always so turned on by this, she wouldn't wear a bra. She never wore see-through shirts or showed her tits off to anyone else, but other men definitely took notice and would gawk at her as she walked by. She is gorgeous after all, and she has those right-sized breasts that aren't too big. They honestly look like the kind of breasts I would want feeding my kids and thinking about that stuff used to make me so horny.

So she wouldn't wear a bra, and since she often runs on the cold side, her nips would get really hard. With the thin t-shirts she would wear, it was almost like you could totally see her tits without actually seeing them, if that makes sense. Again, it definitely is an eye-catcher. Guys would check her out like ALL the time.

Despite her beauty, she's always been a bit on the shy side. It's absurd given how much guys indicate they obviously would want to fuck her. Even at parties, when she gets drunk, and friends-of-friends were obviously into her, it seemed liked they would try to cop a feel.

For instance, we were once at this ski-house party. She had gotten really drunk on this delicious bourbon this guy Chaz brought over, and I could obviously tell he was into her. But she has always been loyal to me and never considers cheating or anything (even to this day, which is partly what sickens me so much about what I did). He kept coming up and putting his arm around her and telling her he really valued their friendship, but every once in a while, I would see the back of his hand graze her breast (again, with her doing the no-bra-t-shirt thing, and it wasn't he warmest in this house, so her nips were hard and poking through the material—an obvious turn-on to all guys in the house, and all of them seemed horny). He was obviously doing this intentionally, but she always gives guys the benefit of the doubt, and even giggled a few times when his fingernails would graze over her nipples. I was seeing this and getting frustrated, so I asked her to come over and sit next to me, and that was that.

Anyway, part of me wonders if she likes the attention (I'm sure she does because she was sort of the ugly duckling growing up and didn't have the highest self-esteem, but now she's drop dead gorgeous). But like I said, we never consider cheating or even doing anything remotely sexual with anyone else, and have talked about how against it we both are.

So, the years go by. While sex with her has always been nice, it seems like things have kinda fizzled over the past couple years.

I have been getting more sexually despondent over time. Again, I think the problem has been largely with me, because even when I try to jerk off and am looking at really hot porn, sometimes I'll lose my erection and need to go mentally concentrate to get it to come back. Needless to say, it has affected our sex life as well, because she often doesn't reach orgasm when we have sex anymore. In fact, I think the last one she had just from intercourse was well over a year and a half ago. So I make up for it by going down on her. But she still seems like she's lost some attraction to me. Nevertheless, knowing our stance, I never felt unsafe or like she would cheat or anything. It's just our sexual passion was basically non-existent.

She took out her IUD a while back because we knew we both wanted to have kids and wanted to start trying. But with my bedroom difficulties, we had no success over the couple of years we've been trying to conceive.

So fast forward a year or so, and she started working at this new job in sales. She's not really used to doing that (previously was a marketer), so she had to go on these sales retreats where they'd practice new sales techniques, and she got to know this guy Asher that she worked with. She mentioned he was really cute, but had a girlfriend, Natalia (as though that meant he himself would never cheat on her). I heard about him, and started to become a little suspicious, though she assured me that there was nothing between them, and besides, we are firm in staying faithful. So I relaxed and dropped the subject.

A couple months later, her office had their annual Christmas party, and I got to go meet her coworkers. When she introduced me to this guy that was really handsome and a little bit taller than me, this fear came over me. Sure enough, that was Asher. I kept my eye on him, and it seemed like him and my wife had a little chemistry, as he was flirty with her, and she was definitely responding to it.

Meanwhile, this attractive blonde girl comes up and smiles at me and says "Hi! You must be Rob. I'm Natalia, Asher's wife!"

When I saw how hot she was, my fears subsided, because Asher must have been totally satisfied by her. We got to talking, and I did a little snooping on their own vows with each other.

She said that while they are committed to remain completely faithful, they have been a little bit open and let the other sometimes go "be part of threesomes, but of course you know, never the sex part!"

So Natalia eventually excuses herself to go to the bathroom, and by that point I was getting pretty tired, so I went looking for my wife to leave. Now again, she was wearing this dress, but with no bra, so naturally, since it was cold out, her tits were rock hard. I come around the corner, and there she is, standing with Asher, smiling and giggling at him.

He reaches up and offers her to taste the wine he was drinking and as he raised his glass to her lips, he lets his fingers graze over her nipple. She gasped in surprise, but looked back up and smiled and giggled as she tasted the red he was drinking.

While I knew she wouldn't cheat on me, I had about enough of this, and went to retrieve her.

I told him it was nice to meet him, and he said likewise.

We started to leave and as we turned around and were walking toward the elevator, he shouts "Hey Gen! Remember to ask your husband!" She turns around and winked at him, and we continued on her way.

I leaned over to her and said "what the fuck was that about?", clearly exuding some degree of jealousy.

She rolled her eyes and responds "nothing... I'll tell you later."

I was a bit drunk myself, so when we got home that night we both passed out and I forgot all about it.

So a few weeks later, Genny and I were at home watching Devil's Advocate (which has some really steamy sex scenes), and both of us started to get really horny. I looked over at her and raised my eyebrows to see if she was interested in having sex. She grinned back over at me and exclaimed "let's go!"

I was so excited, because it had been months since we last had sex, and the last time, I lost my erection during the middle of it and couldn't get it up again. Which was both humiliating for me, and frustrating for her, as neither of us reached orgasm. In fact I think all of her own orgasms had been self-induced for a long time.

We ran over to the bedroom to capture the heat of the moment, and quickly tore each others' clothes off. Her nipples were super hard, and her pussy was dripping wet. Genny is the kind of girl that starts getting sopping wet as soon as she thinks about sex. Like seriously seriously wet. You put your hand down there, and it's like she secretly smeared KY jelly all over her pussy, except it was all from her own vagina.

I was rock hard, and jumped on top of her and dropped my penis into her velvet wet vagina and started pumping. She was clearly in a lot of pleasure and wrapped her legs around me as she sighed and moaned passionately in my ear. Now, for most guys, when they're horny, this would almost invariably lead to an orgasm. Not me though. I could feel myself getting closer, but then it would subside again and again. I started to fixate on the fact that I couldn't get myself there, and sure enough, my erection started disappearing.

Within seconds, I was completely soft and my wife was like "... ugh, again?"

I felt so embarrassed, and reminded her I wanted to get myself checked out (you know, to save some face) by a sex therapist.

She nodded along, but I could tell she was frustrated by our non-existent sex life. I felt terrible for her. I started asking her what we could do.

She shyly responded that she didn't know.

So I asked if perhaps a threesome would be good, and her eyebrows instantly perked up.

She asked me "what do you mean?"

I said, "well perhaps we involve someone else, maybe another girl, and she is there to just go down on you and fondle you and everything."

She rolled her eyes and was like "well, i'm not really into girls, plus I think that would be more for you, but if it keeps you hard..."

So I asked her if a guy is what she was thinking. She seemed to think for a moment, and I said "but obviously he can't have sex with you or anything."

To which she responded "oh no! absolutely not! No, that would make me sick."

I felt comforted and said "me too. I couldn't ever watch another guy with you."

She nodded along and we seemed to be on the same page. So then the topic of who came up next.

I asked her if maybe we should put out a personal ad or something, and she seemed hesitant.

She was like "I don't know what we'd be getting though, I'd rather go with someone I know." Surprisingly quickly after that, she said "hey... you remember that guy I work with, Asher?"

My heart dropped a little bit, because I felt like this guy was better looking than me, and probably could keep his dick up like 99% of other men. I said "yeah... does this have to do with what he was asking you about at the Christmas party?"

She snapped her fingers and goes "oh yeah! Yeah, actually that's right, he did ask me if we wanted any help or were interested in doing stuff with him."

I said "hmm... well he DEFINITELY can't have sex with you."

And we both agreed that penis-in-vagina was definitely off the table with anyone else we involve. So I felt a lot better, and warmed up to the idea. After all, if it made her less frustrated, I could work on my problem on my own, and hopefully keep things alive between us.

So we invited him and Natalia over for a BBQ that weekend. Genny wore a dress with a short skirt and heels, and some sexy underwear, and I was wearing shorts and a polo. As usual, she had no bra on. She looked hot as hell, and I figured it was appropriate given the subject matter we were going to discuss.

We were nervous to break the subject but after a couple beers, things loosened up. We went over to our camping stove and all sat around it in some big adirondack chairs. Genny sat to my left, Asher to my right, and Natalia across from me.

We were all sitting together around our camping stove roasting marshmallows when Genny goes "so Asher... remember that thing we talked about at the Christmas party?"

His eyebrows instantly perked up. He was like "yes... yes, I do."

Natalia looks over at me, then at Asher then at Genny then back at Asher and was like "what? What did you talk about?"

Asher looked back at her and goes "you know... "

Natalia was then like "oh, right I know" and rolled her eyes.

I started getting turned on by the idea of Natalia being there as well because after all she was quite hot too. But when we started talking about it, she indicated she was not interested in any of it (despite her having told me at the Christmas party that she did in fact get involved with that sometimes). I couldn't help but wonder if it's because she heard about my sexual problems through the grapevine (which made me feel kindof shitty).

Asher started reassuring us that we would be the ones in control, and everything would be on our terms, which was clearly intended to make me feel better.

Genny seemed to be very excited about the idea, as she crossed one leg, and was bobbing it up and down with this sly smile on her face. I know when she does that, it stimulates her clitoris and she was probably getting some extra pleasure from that. She was gazing over at Asher's attractive face into his eyes, and he was returning the same longing look to her.

I glanced at her dress and her nipples were rock hard despite it actually being an unseasonably warm early spring day. She uncrossed her legs and sat back, as if to give a full view of her underwear to Asher. I glanced over at Asher and saw him glancing down at her skirt and biting his lip. Who wouldn't when looking at sexy underwear? When he licked his lip, I glanced back over at Genny and noticed that at some point when she went inside, she removed her underwear.

Her pussy (a beautiful pussy, remember how I described it earlier) was fully exposed and she spread her legs to intentionally make it that way. She sat in the chair so that the sun was shining directly on her, and her dress was short enough that when she sat down, it would slide up, and give a full view to anyone that looked. Picture her gorgeous pussy and beautiful muff staring this guy she has long had chemistry with, teasing his mind and turning him on. What's more is she had become quite wet, and the inside of her thighs were glistening with her vaginal juices. With the wind blowing, I could practically smell her beautiful aroma, and I think he could too. I glanced back over at him, and saw a bulge growing in his pants.

This quickly started to get to be a bit much for me, and so I glanced back over at Genny and said "wow."

She noticed me noticing her move, and seemed to feel a little ashamed, so I started making some banal conversation with Natalia sitting across from me.

Natalia quickly finished up her topic and mentioned that she and Asher had to get home to their kid.

Genny mentioned she didn't even know they had a kid, and so Natalia started talking a bit more about it.

Natalia mentioned they only started trying a year ago, but almost the very first time they had unprotected sex, they trace back to being the time they conceived.

She winked back over at Asher and said "he's just such a virile man, it didn't take much for him to knock me up."

Asher blushed and winked back at her. He then told a brief anecdote of "slipping a couple past the goalie" in his earlier adulthood, but that his girlfriends had both had abortions, so this was his only child.

Natalia mentioned they were going to have a second child next year, so she was back on birth control.

It started getting cold at this point, so the natural break in the conversation led them to stand up and say their goodbyes to us.

I hugged Natalia and shook hands with Asher. Natalia came over and hugged Genny, and then so did Asher. When he did this, I was shocked to see him put his hand down and slide it between my wife's legs. As he stood back, his hand was wet with her vaginal juices, and he held it up to his nose, sniffed it, and then licked it clean.

I suppose Natalia was used to this kind of stuff as she just rolled her eyes and said "okay Ash, let's go!"

I kept trying to test Natalia for chemistry that night, but there was virtually nothing. She was just not into me.

Just before leaving, Asher turned around and said "hey... there's going to be a good basketball game on TV this weekend, and I got some amazing mezcal when I was down in Cancun last month. Do you guys wanna hang out?"

I was already a bit jealous given how fast things quickly progressed, but Genny quickly blurted out "absolutely! What time?"

I started to feel threatened, because here is this virile, attractive guy, with clearly the ability to get an erection propositioning us to come over and "hang out" (I can read between the lines and know exactly what he had in mind), who just got a peep show from my wife, and also had the chance to smell and taste her pussy all in one go.

He responded "game starts at 8, so I'll see you at 7."

And Genny immediately responded "yes! See you then!"

After they left, Genny was saying "here's what we talked about! Now it's going to happen, and winked at me."

I felt like I wanted to bring up the fact that she took her underwear off, and then not only showed him her pussy, but let him smell and taste it was making me a little jealous, but I held my gut in and didn't say anything. I felt embarrassed and ashamed that I wasn't able to please her at all, and also felt like she somewhat deserved to be pleased by another man while we tried to have sex. After all, our ground rules prohibited him from penetrating her, so there was really nothing for me to be worried about, except the remote possibility of her feelings for him developing into something more.

So the weekend rolls around, and that night was the basketball game. I noticed Genny was in a hurry that day to clean up the house, particularly the bedroom, and took a shower and dressed up sexier than I usually see her. She also wore this perfume she wore when we first started going out, back when things were kindof hot between us. For some reason, all of this was making me a little jealous, but I tried to reassure myself that things would be alright. She was wearing a low-cut see-through top with no bra (as usual), which meant that you could see her beautiful breasts right through her shirt when you looked at it (also a new thing-she never revealed her breasts). She also wore a short silver skirt and a pair of platform heels.

When I asked her if she was wearing underwear, she quickly turned around and winked at me and said "nuh uh!" This both worried me and turned me on at the same time.

A few moments later, the doorbell rang, and there was Asher, wearing this tight white t-shirt, a pair of slim-fit jeans, and loosely-tied boots. He had this belt on whose buckle was supposed to be the face of a bull, but looked very much like a swollen dick - I assume that wasn't a coincidence.

He was carrying this bottle of mezcal and said to me "hey Rob! This mezcal is the best stuff I've ever tasted. You guys have to try it!"