MrsBlackBlowupDoll
Member
Posts: 1289
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My wife and I first got into cuckolding before we were even married. We had been dating and had become serious and had informally drifted into exclusivity in that way you do when you start getting serious about someone. I had shared with my then girlfriend my kinky submissive fantasies and yearnings (one of the scariest moments of my life,) which touched on but did not center on cuckolding. To my great joy she did not recoil or reject me, but she was daunted. She was as vanilla as a fresh broken bean and was worried that I would need or expect from her more than she was comfortable giving.
She was willing to experiment and I was determined to make sure that our sex life was good for her and not just topping from below. At the same time, she was recently free of a long-term, serious, exclusive, relationship that had ended with a broken engagement. (I was in a similar place.) As a result, she was reluctant to settle down again and had frankly slid into seriousness with me reluctantly. The idea that she could have me and still be free to play the field was something that really appealed to her. To be truthful about it, I think the fact that I was willing to give her that freedom – to not demand the exclusivity she assumed was the fee for a committed relationship – sealed the deal for me in terms of winning her. (What is that cliché about “if you love something, set it free?” It turned out to be true for me.)
We started with talk. Just saying it out loud was titillating for both of us and she found the idea gave her the exhilarating feeling of freedom and empowerment. She had quickly become comfortable talking to me about her past lovers and getting honest about comparing the sex she had with them to the sex we had, and I think that candor also helped pave the way. In any event, it didn’t take very long from the permission talk to the first actual incident. Less than two months, I think. She had a new coworker she felt chemistry with and they had started flirting. I encouraged her to take it as far as she wanted, leaving no doubt that I was for it, but not pushing.
One day we had a date scheduled (we still did not live together at this time) – tickets even if I recall. She called me late in the afternoon, just as I was getting ready and after some hemming and hawing, mentioned that Evan had raised the possibility of takes later. She was nervous as could be about bringing it up to me. The talk become sexually charged at once – perhaps as charged an experience as I have ever had. I told her not to worry about what had been planned, there were many nights we could do things, what would she really prefer doing that night. With a dry mouth she told me she would rather go with him. It was one of the most erotic moments of my life. I quickly gave her major affirmation of the decision and after we got off the phone I spent the rest of the evening repeatedly masturbating, unable to turn my thoughts from the situation for more than brief recovery times. (The ability to get it up multiple times in an evening was greater back then – but not usually as good as it was that night!) I eventually gave up and went to bed.
Late that night, around three in the morning, I heard the door open (we lived apart still, but she had keys.) She came in and was very nervous. She worried that, like so many men, I would be hurt and angry at the reality despite my fantasies. My loving and enthusiastic reaction visibly relieved her and removed that worry. I asked for details and with a mirthful smirk I got them. (I can still remember the smell of sex as she made me sniff her breasts and torso.)
That was the first. As I said, he was a coworker she was attracted to. At first, he thought that they were both sneaking around and she let him think so because it was exciting for her to play-act that she was. When he found out, it didn’t really change anything for him as far as I know. They had a torrid on-going thing for nearly a year, which ended only when his own wedding (he was engaged) got close and he felt he should recommit his sexual focus on his fiancé. To this day, I have never met him. Her second was an old high school flame she hooked up with when she went home for the reunion. It may be worth mentioning that she went with this intent and may have skipped the reunion altogether were it not for the possibility.
Her third followed the same pattern – someone she knew who didn’t know me. Separation of spheres was maintained; she had affairs, I enjoyed them vicariously when she told me about them. Which was usual, but not always. I realized early that the obligation of taking care of me later could be enough of a drag to discourage her when she was on the fence about a hook-up, so I gave her space and let her decide when and whether to fill me in. Doing things this way made her feel more comfortable and drew the two of us closer together than would have been the case if we started right in on the three-in-the-room stuff.
Keeping things compartmentalized this way was easier before we lived together, were married, and our circles grew together, and even afterwards we could make it work. (We made sure the voice on the answering machine was hers and just said to leave a message – that kind of thing.) Meeting new men who would display interest became harder, however. My wife is quite good looking and pleasant, so that wasn’t the problem. The truth is that nice guys in the real world don’t put the moves on married friends and coworkers. Guys who do tend to be jerks she isn’t attracted to; and, unfortunately, my wife has never been the kind of woman who naturally makes the moves first. Complicating her natural tendency to be the pursued rather than the pursuer was concern for her reputation, both social and professional. She didn’t want to be forward with a coworker she thought was hot only to have him gab it about. (I know some women like the reputation for being sexually bold and unconstrained by marriage, my wife isn’t one of them.) So we turned to classified ads in the “alternative” weekly newspapers.
She met a number of lovers that way. She would exchange some emails, and then arrange a “nothing is going to happen yet” get to know you take. In the early days, I actually accompanied her to the bar (she was nervous of her safety,) sitting in another part and keeping an eye on them. We pretended to be separate. Once or twice she did point me out to the date, if she was comfortable with it. Eventually she started calling me over to meet some of them. This was big for us, since the cucking had always been a solo event for her before. After a while, she felt safe enough not to need me with her. Discretion was really big for us back then, but it helped that we live in a large city, so the chance of running into someone we know was pretty slim (besides, they weren’t doing anything butting chatting over takes.)
Since she didn’t know these guys before the ad, we had them at our apartment (we were living together by then.) I went out of the house to a coffee shop or bookstore within a block or so and would wait for a call on my cell before returning. Sometimes we had prearranged check-in calls. Then we finally started having me meet them when she found guys OK with having me around. I would stay out of the way – discretely in the kitchen or something doing chores. I was able to peep at the through open doors and the like (it was not a large apartment.) The key thing here was finding guys who were fine with it. Not everyone was. Overtime we had giuys who were OK with me sitting and watching – even some who wanted me to undress her or help guide their cocks in. But this took time and was not as common as fantasy would have suggested. By way of these ads, she met her next longer-term lover Luke, a fanatically fit specimen who she saw for over a year until he moved across country. (There were a couple of reunions there after, but he started to fall out of shape after moving to “drive everywhere” country.) He was way cool with the arrangement and we even got to the point where I wore a uniform and brought them takes while they made-out of the couch.
In ads, the critical thing for her was evaluating them on what their response was. She would email them a few times before meeting them to weed them. For the guys I guess you could say it was a little like application essays. She was upfront about requirements and conditions like age range, smoking, facial hair, tattoos, have use, etc. in order to avoid wasting time. She didn’t require pictures in those days (*** to provide her own,) but even if they gave one the words outweighed it. What she was looking for was chemistry. Did this seem like a guy she could spend an hour chatting with before fucking? Did he seem like a guy with a sense of humor? Did he have positive, fun-loving attitude? Was he polite? Well-spoken? Friendly? What were his interests? She wasn’t looking for drama or darkness, she was looking for a good time. She was always mindful of the idea that this was a lot of work for a one-off so she was looking for guys whose company might be pleasant enough to make it a recurring thing. As she put it once, she was “looking for more than sex, but not much more!” Like everyone we later moved from print classifieds to online dating sites. Actually, we did not find them an improvement. A lot of the sites really try to weed out or discriminate against extramarital sex and some of the others are just filled with trolls. I guess because the sites make replying so easy, you get a lot of time-wasters and horny guys just playing the lottery then we used to with print ads. Still, we had some luck that way, for sure. We also joined a local poly support group and she met a couple of lovers at it. (I didn’t, which is just as well since I’m not allowed.) This was a good experience, but bluntly poly and cuckolding are not exactly the same so it wasn’t as productive as we hoped in terms of dating. (I think it would have helped if she were more willing to go on her own to it for a while. Unfortunately, she hasn’t had much luck with wing-gals and doesn’t like solo prowling.) She also had a very serious relationship with a guy she met from a social activity group she is in. Most of the men she meets there are coupled or are too correct and respectful to hit on a married woman, but he was from the next state over and didn’t know her so well. It was really, really torrid for a while (he flaked and blew it.)
Of course, discretion is not such an issue for us anymore since we are pretty out with folks (except at work.) Now she has even been fixed up with guys by some of our friends and I’ve introduced guys to her after explaining about our relationship. But in this is how we got started and what we did in the early days. I hope it helps. I happy to answer questions (and I think my wife might be.)
Best of luck to you on this great adventure! Pantalone, Wittol, oblate, abnegator, fellator, pathic, irrumatiophile,fop, epicene, cotquean, skivvy, thrall, and pilgarlic.
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