I'll try not to give the whole play by play because our adventure has sprawled over the last 8 months or so.
My wife has had wild promiscuous periods in her life but all in all, pretty vanilla. Nothing too extreme other than the odd ex-boyfriend begging her to try a little of this or that.
I've had a hotwife/cuck fantasy for as long as I can remember. And since being with her it's been 100 fold (there's .. reasons for this both sappy, complicated and kinky that I'll move on from).
I've taken years to admit this to her. All of our dating relationship and the first couple of years of marriage. But I finally, after a bottle of wine (each) at a nice restaurant in a secluded corner, bashfully opened up to her about this.
Now granted - I've watched all the cuckold porn, the caption pics, the stories and what not - but given how vanilla my wife is - the sharing part alone I thought was a big enough deal to offend, frighten, or risk our relationship on. I wasn't about to get into anything else. I've had years to think about this and allow the fantasy to wander every which direction and wasn't about to drop it all on her at once. Hell - I figured, best scenario is that she thinks this is a great idea and we find the odd guy or two here and there through life and that it'd get no more extreme.
So that night we go home and get it on with some dirty talk about it.
Over the weeks, conversation would go from hot, to more serious as she was working it out in her head. And I think like a lot of women, she wondered if this was some sort of game I was playing where I'd eventually ask to sleep with other women, which she was 100% against. She was jealous and selfish and possessive and had zero motivation or desire to move her stance on those issues. I swore to her up and down, that I just wanted to see her (or even know about if I wasn't present) her being naughty and getting pleased thoroughly by someone else. I'd say she 99% believed me but let that 1% of doubt just kind of hang there.
She'd shit test me, and tell me - not knowing this was part of my fetish - that if she was to do this, the guys would have to be a lot more hung than me. And that I would need to be ok with it (which led to another amazing dirty talk and sex session).
So over the months, we'd talk - sometimes tinker on arguing or have serious conversations when she was probing my mind in where this was all coming from and I'd try delicately to give my own self-psych-analysis without going into territory that would scare her off.
And then she noticed .. I guess, how eager, how hard/erect I got if she was jerking me while we were dirty talking out a scenario, how enthusiastic I got going down on her, and started to really playfully get off on ramping me up, getting me to get her off, and leave me hanging. It was torture - a torture I knew I'd love, but this was something all new for her. She really liked her new found power and control over getting me this excited, and denying me.
After I'd get her off with my hands or mouth, she'd joke that she would be off to see her lover now for some amazing sex (there was no lover - this was all play) and that if I was lucky she'd tell me about it when I got home.
We'd go through our day and I'd be more flirty, more .. helpful, more willing to volunteer a massage. She noticed on days she left me hanging that she really liked being around me more than usual. That I was more doting, more affectionate.
She'd ramp this up when we'd go to bed and she'd pretend like she just came home from a date and ask me to kiss her and asked if she tasted like him? Could I smell his cologne? I'd go to finger or kiss my way down her and she'd say, "oh no no .. you can't do that after I've been with another man". And I'd continue my eagerness in my attempts to anyway telling her I wanted her so badly I didn't care. We role played like that several times where I'd finger her and she'd say, "See? See what he did to me? Do you really want to continue?" and of course I did.
This would, in other sessions graduate to me fully going down on her and her telling me how naughty, or nasty this was... that I was down there tasting their love making and that she couldn't believe that I wanted to taste her so badly after what she had just done to our monogamous relationship with another man. Most of the time she'd be laying on her back, but on some hotter sessions she'd get super aggressive and climb atop my face and ride/grind me until she got off.
By this point we talked more frequently about me not getting off. She would tell me she really would prefer if I didn't masturbate and to be honest about it if I did. And most of the time I stayed true. I let her be in control. If I begged enough or if she was feeling nice. She'd jerk me, or suck me, or even let me stick it in a bit but never cum. If I begged and was pitiful enough about it she'd let me have sex with her which was usually over fairly quickly and we'd laugh about how insanely pent up I was.
But she started to get even a bit more wicked herself. She'd want me to jerk off in front of her. Or get me off with her feet (we played with her feet through most of our relationship as I have a foot fetish).
So we started talking a great deal about tease and denial. About the power that gave her over me. And in her own searching - which she usually doesn't look up anything sexual online at all, ever. (to my chagrin). But she discovered chastity cages. And we decided to buy one so I would quit masturbating.
And she's really taken to looking into cuckolding as it has has worked it's way into our lives quite a bit. Getting me to dress her, drawing her bubble baths, giving massages, dice games, all sorts of stuff. She jokes that since I've been chaste that I've become putty for her to mold.
So we go bouts, sometimes a few weeks, sometimes a couple of months with me being orgasm free and locked up. And maybe half the time, sometimes less, we might role play or dirty talk about her being with a "boyfriend".
The change in our relationship has, as she has told me, allowed her to feel tremendously more secure in the prospect of stepping out. She sees how much control I'm willing to give and how much I enjoy it and it's really started to sink in that this was never some long-con ploy on my part, that this fetish or mine really is about her pleasure.
That without going the role-play route that led to chastity...she says she would have never felt comfortable enough to play with others.
But here we are. It's Thursday and tomorrow night she's meeting a guy in a hotel bar that she'd been talking to for a week that we met online. He looks fresh out of college but is 25 and fairly hung. He seems to be respectful while talking a big game. She hasn't had "real sex" in months, and largely to me being so relentlessly teased ... when we do it hasn't been the sort of sex that gets her off unless I fuck and grind on her after I cum with my limp dick until I can get a clitoral orgasm out of her.
We're both so giddy and nervous and excited all at once. We realize it may go wrong or we might get stood up but we're finally here. We're finally going to break this barrier and let someone else into our sex lives.
And I would have never imagined that opening up to her in what seems to be "so long ago" and just yesterday all the same about just wanting her to sleep with someone else - and back then I was selling it as a threesome with me, just regular old hotwife type sex, that we'd go down the femdom-like journey and that is the very thing that made her secure enough to actually want to try it out for real.
So wish us luck! I had to tell someone and had no one to tell!
Mark & Wicked Teresa