TL;DR: Tomorrow my (until now monogamous) wife of five years is getting fucked by an old friend of hers and getting paid for it.
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So after about a decade of fantasizing about becoming a cuckold, it's actually happening for real on wednesday evening. No fantasy here, all true story.
A couple months ago I (M34) wrote to my wife (F33) a letter detailing and explaining a whole list of kinks, fetishes and fantasies I've had for years and never really had had the courage to act upon. Mosty power dynamics, orgasm denial and control, sph, submission, and of course cuckolding. Honestly I thought the later would be the last likely to interest her (she's considerably conservative and very much with a zero tolerance to cheating). Turned out, I was wrong.
In the part of the letter in which I explained cuckolding, I actually included an open consent on my end. Essentially I put a few basic rules (safety, protection, communication) and made it clear that she had my consent from than moment on, whether she ever chose to act on it or not (I genuinely thought she would never, though I of course hoped she some time would).
Not a month had passed when she told me she was in fact interested in the cuckolding dynamic and that she wanted to make sure I was on board, since she already had a prospect for a bull. This she told me on a text message while I was at work. Saying that I was dumbfounded would be an understatement. Not only was she on board with trying to turn me into a cuckold, but she actually incorporated an element that I did not expect: she's actually getting paid for it.
Turns out there's a guy she knows from way back and he's always had a crush on her. He would sort of try to slip into her DMs every now and then. You know the drill: she would not quite flirt with him, but wouldn't turn him down entirely either. That is, until she read my list of kinks and realized she could actually go through with this.
It got to a point in which he offered to buy her dinner and a present (we do very well, but the guy is considerably loaded). She said she was intrigued, but that she just couldn't come home with a new luxury bag without raising questions (he thinks she's going h behind my back). So he offered to transfer the money directly to her. This, of course, made her feel like an actual whore. Instead of feeling offended, she realized it turned her on considerably to get paid to have sex with a guy she wouldn't otherwise (she tells me he's not ugly at all, but nothing to write home about).
It's been about a month of talking things over and me assuring her I'm ok with her going through with this. I was also very adamant on the fact that, even though I'm ok with her accepting money in exchange for sex (I get the appeal and it turns me on very much too), she should absolutely make sure to never use said money for anything remotely necessary or even useful for me or even her. That is, she should use that money strictly for superfluous shopping and only things for herself. I don't ever want to see a penny of that money, since that would literally be the definition of sexual exploitation.
Thing is, this was already supposed to happen. They had agreed on having their first encounter last thursday, but he had to cancel a couple hours before due to a work issue. So even though it hasn't happened yet, I have already dealt with the anxiety of the night before. It was intoxicating. She had her nails done, waxed her legs, butt and pubes (she hadn't waxed in Idk how long) her skin was so smooth and sexy, and I just felt beyond myself knowing that the pussy I was licking to orgasm was silky smooth for the benefit of another guy who would be fucking it less than 24 hrs later. I've been immeasurably horny these days in expectation and with a rush of conflicting emotions that's hard to describe.
I hope it all goes well and she genuinely enjoys herself, so that she's motivated to continue on this journey. Obviously I'm not going to watch, since she's supposed to be cheating on me with him (we're not really worried about the moral implications, since he's single and thinking he's getting away with fucking a married woman behind her husband's back, so whatever).
Wish us luck.