How we came to be here: A bit of background on Billy and Jane

One of the questions I get asked most often in the chatroom is, ‘how did you get her to do it?’ or some variation of that. As there really isn’t a simple answer, I figured I’d write a post about it.

I want to start by saying I don’t believe that I ‘got’ or ‘convinced’ her to do it, as those words imply a sort of manipulation or trickery to me. And I also don’t believe that what I’m writing is a manual on how to convince other wives to do this. It’s simply how it happened for us. So without further caveats, here’s a condensed recounting of how we ended up where we are now…

Jane and I were high-school sweethearts. In 1993, I saw her for the first time from across a classroom and, as clich?d as it sounds, it was love at first sight. We got to know each other for a year, just as friends to begin with, and started dating in 1994. We’ve been together happily since then and got married in 2006 (marriage wasn’t really a priority for us as we were in love, completely committed to each other, and we viewed marriage as more of a legal formality).

In roughly 2004, I started becoming actively interested in cuckolding after seeing and reacting to a captioned pic that I found while surfing around. I can’t recall exactly what it said, but it was a picture of a naked woman leading a half-clothed guy into a bedroom, away from the camera. The woman was looking directly at the camera, smiling impishly, and the caption said something like, ‘You stay right here, hubby, while this hung stud fucks me silly.’

My first reaction to the picture was ‘who in the hell gets off on the idea of his wife not only fucking another man, but also having her rub his nose in it?’ I then unwittingly thought of Jane doing that to me and I felt a surge of those now familiar, stinging butterflies of jealousy and shock. I realized that, while I was appalled, I was also as hard as a rock and almost shaking from the rush of it. I had no idea why I was so turned on, just that I was.

Not being one to shy away from something that piques my curiosity (and my libido) I immediately sought out more of the captioned pictures to see what it was all about, trying to figure out why it had such an effect on me. When I finally came while looking at them, I don’t think I was really thinking about Jane doing it to me, just me being in that scenario. The very imagining of Jane actually doing that was far too new, painful, and inconceivable for me at that point.

For quite a while, I explored the different facets of the scenario, enjoying the majority of what I found. I also started asking myself serious questions about why it seemed to turn me on far more than anything else I’d ever been exposed to. As I explored over the course of a few years, talked online with others who were into this, and eventually made my way to the cuckoldplace site, I started to think more and more about actually doing this with Jane.

The idea became insanely erotic to me, but I didn’t dare tell her about it, as I was afraid of how she might react. Worst-case scenario for me wasn’t that she would reject it outright, which, admittedly, would have been disappointing, but that she would run with the idea and I wouldn’t be emotionally ready for her to. Eventually, I realized that I had a choice of either telling her about what I’d been fantasizing, or living my life with an unspoken desire that would potentially leave the both of us sexually lacking.

I think it’s important to note here that Jane discovered a number of years ago that she had been born with a sensitivity issue that made sex painful for her during the first few years of our relationship. She didn’t even know there was anything wrong, as she had no frame of reference. She thought that it was just the way she was supposed to feel during sex. She went to a specialist and discovered that, not only was her sensitivity level far beyond what was considered normal, but that many women have this same issue and never make that understandably awkward leap to asking their doctors about it. The most wonderful piece of news, though, was that there was a treatment for it that would effectively negate the problem! After a couple of months of surprisingly easy treatment, she was rediscovering sex and really, truly enjoying the physical side of it for the first time. The difference was like night and day.

That said, it took longer for us to overcome her psychological association between sex and pain (and primarily due to this negative association, we let anyone we know that we might play with that she is not at all turned on by physical pain). But as the physical and psychological obstacles to our sexual intimacy began to disappear and we played more, I felt more open to suggesting ideas that I thought we might explore in the bedroom.

At some point early on, I realized that one of the biggest turn-ons for me about cuckolding was the submissive aspect. We had played with tying each other up a few times here and there, but neither of us really got into the dom/sub role with any real vigor up to the point when I finally came out and told her that I really liked it when she was assertive. And not just assertive, but dominant and even a little teasingly mean.

She understood, and I think played along the first few times we tried it, trying to shift from the sort of things that she’d been used to saying to me for so long, and taking cues from my reactions as to what worked and what didn’t. She got into it quickly, though, as she noticed how much it turned me on and before I knew it, she was saying things that I couldn’t believe were coming out of her adorable, sweet lips.

But telling my wife I had been fantasizing about watching her fuck another guy is still a leap from letting her know that I was into the dom/sub dynamic, and I was still wrestling with how to tell her, when to tell her, and even whether to tell her. I wanted to be sure that if that dreaded worst-case scenario of her completely jumping on the idea (which had been brewing in my brain for so long) were to come true when I told her, I’d at least be as prepared as possible for it.

It happened in early 2007, February or March, I think. We were sitting on the couch together, mostly naked, playing with each other with our hands and I asked her if she had any deep, dark fantasies that she’d been harboring. I told her I wanted to hear them whether she thought I would like them or not, whether we’d even consider doing them or not. I’d asked her this before, and as usual, she shied away from the question, saying she really didn’t think she had any.

Now, I knew full well that she’d had at very least passing fantasies about other guys, as any sexual being does. People can’t help but wonder ‘what if?’ and the imagination takes off from there. I think, like a lot of women who’ve never even heard of cuckolding, much less considered it, she was reluctant to mention even these innocuous fantasies, as she was worried about making me jealous and/or pissing me off. So I asked her outright if she’d thought about other guys. She admitted with a sheepish grin that she’d only vaguely fantasized about a few male celebrities, but that was about it. And then she quickly turned the question back to me.

She had my cock in her hand while I was running slow circles around her clit and I realized my heart was racing. I heard myself saying ‘well, actually, I’ve been fantasizing about watching you while you fuck someone else.’

Her hand stopped moving and she cocked a suspicious eyebrow. She just looked at me a moment and asked me in a tone of voice that told me she thought she already knew the answer, “a guy or a girl?” (We’d discussed threesomes with another woman a few times, and even had the opportunity to act on them a couple of times, but she was adamantly not into the idea, and she knew I was aware of her feelings on the subject).

When I said “a guy,” she looked surprised for a moment, smiled a mischievous grin that I still have burned in my head to this day, and said, “Really…” as if she were simultaneously stunned and considering doing what I’d just confessed to her. I noticed, however, that her hand had started pumping my cock again as she pondered it.

She started asking me questions about it, and I asked her questions back, about how we felt about it, why it turned me on, whether she liked it etc. I can’t honestly remember everything we said as we were getting more and more turned on by the fantasy floodgates opening as well as physically playing with each other.

Over the course of the following couple of weeks, we talked about the fantasy, both in and out of the bedroom. I explained to her what I’d discovered, about why I thought it turned me on so much. I talked with her about it not being a trick to get her to fuck another guy just so I could have ‘permission’ to fuck other women. She started confessing to me stories of co-workers or other guys hitting on her or outright propositioning her that she’d held back because she was afraid I’d be angry with her, or them, or both.

We talked about it as openly and as honestly as I think we have ever been with each other and after a couple of weeks, she told me that, at first, she wasn’t sure that she was really all that into it, but had been willing to play along and explore for my sake. But now that she’d had some time to get used to the idea of playing with the fantasy, she realized that it really did make her wet and she got off on it. She wanted to make sure that we agreed it was just fantasy, that we weren’t actually going to do it, at least not in the foreseeable future, but that she really was having fun with it.

After that, though, she seemed to really let go and took to the dominant role of fantasy cuckoldress like a natural. We would talk dirty to each other while we played and fucked like bunnies, teasing each other with how absolutely naughty we were being. A few months of incredible sex later and we were talking hypothetically about trying it in reality. We had agreed that what we said we wanted in the heat of passion, roleplaying and the like, didn’t mean that we were actually going to act on it, but we were at least starting to put ourselves in the situation in our own heads and considering the consequences.

Over the next few months, we chatted quite a bit with the guy who ended up being her first besides me in her entire life. He and his wife play with others, both together and separately, so he’d had experience in this sort of thing, and very patiently helped us to explore our desires, allay our concerns, and generally by being a friend to us in our journey. We can’t thank him enough for everything. And his wife, too, for lending him to us for a bit now and then.

He also introduced us to webcamming, which provided a great way for Jane to get used to the idea of being naked and frisky in the presence of another guy at her own pace and comfort level. Believe it or not, there was a time when Jane was reluctant to bear her absolutely gorgeous breasts on cam for another guy, much less do anything more daring. Now she loves to use her toys and cum while she watches the guy on the other end stroking his cock, knowing he’s watching and listening to her get off for him.

We watched different kinds of porn together, primarily from the cuckoldplace website, and talked about what we liked, and didn’t, and why. A favorite series of hers was the sharingmywife.com movies, which seem to be on the tamer cuckolding spectrum than something like the Roman Video clips (not to say they’re no good, just not quite her thing, or what we were wanting to try in reality). A big ‘thank you’ to Katie Morgan and Penny Flame too.

Anyway, an afternoon came in September, or close to then, when we’d just collapsed on the bed after making love. I asked her if she’d meant what she’d said while she was riding my cock, that she really wanted to fuck another guy, that she was ready for it. She smiled, panting, and said, ‘yes, I think I am.’ I kissed her, and she giggled as we worked each other into another frenzy, knowing that we’d taken another big step.

We played more on webcam with her first guy, as well as others, and an evening came in November when the three of us had a bit of time to get together, if we were willing to make that leap. We’d originally discussed meeting at a club that had some hidden nooks and crannies to hide in, but eventually decided that if we were going to be at all naughty, we might want more privacy than a club could offer.

We talked for a couple of hours and came to the realization that neither of us could predict how we would feel afterwards. We were both afraid that we would see each other differently, or maybe one would love the other less, or not at all, or any number of horrible things, but there was no way of knowing, absolutely for sure, until it had actually happened and was done.

We also agreed that no matter what happened, or how hurt we might feel, we would work through it together and if it meant never doing it again, so be it. In the end, what it boiled down to for us was that we knew we wanted to try it, we knew we loved each other, and we had enough faith in our love for each other that we felt we could overcome whatever negative thing might result from trying it.

We got Jane dressed and even though she was more nervous than I’d ever seen her before in my life, we were soon in the car, on the way to the adult bookstore where we eventually met him in reality for the first time. And while I’ve said it before, I’ll say it again, we couldn’t have asked for a better time or for a better permister to play with.

“Regret for the things we did can be tempered by time; it is regret for the things we did not do that is inconsolable.” -Sydney J. Harris

This is an amazing story of your progression. I really appreciate your time and efforts to post it here. Thank you !!

Excellent post, thanks for sharing

Tony

a lovely read.

There will by more, right?

Hi everyone, thanks for the comments and we're glad you like it.

As far as there being more to come here, I'd be glad to answer any questions, but this is really more of a background thread... continuing adventures can be found at: https://www.cuckoldplace.com/2_42883_0.html

Fantastic reading and thanks for sharing all you have shared, it was a complete pleasure to read your background as well as watch all the other bits!
Superb.
Rafael

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