The Cuckold Training Diaries - Part 1

Avery

So, what do you do when your husband confesses that he wants you to cuckold him?

I'm not sure what you would do, but I can tell you what I did. First, I asked him what that meant. Then, when he explained that it meant that I would have sex with other people while he remained faithful to me, I freaked out a little bit. Or a lot, depending on who you ask (Milo would probably say I freaked out a lot). Looking back, I'm not entirely sure why I freaked out to the degree that I did. I think any woman might find it strange if her husband asked her to have sex with other people, but I took offense at it for reasons I really don't understand.

Anyway, that part's not important. After taking some time to freak out - honestly, it was weeks and it was not a great time in our marriage - I came to my senses and started doing some research. Milo had explained the basics over and over, but the truth was, he didn't have a great understanding of his fantasy, other than to say that the idea of me sleeping with other people turned him on. So, I went online.

You might already know that reading about cuckolding online can be a bit of a minefield. There are some helpful resources, and then there are lots of sites where guys get into arguments over all kinds of meaningless bullshit and minutiae. I'm pretty sure none of the guys arguing have been cuckolded, either, and I wouldn't be surprised if they were all single, too. Whatever. Again, that's not important.

What's important is that I learned about Milo's fantasy. I read articles, I listened to a handful of podcasts (you can truly find a podcast about anything these days), I got in touch with a few women that were actually active participants in this lifestyle with their husbands, and I learned that I didn't, in fact, have to freak out, that it was actually possible to entertain the idea of Milo's fantasy.

In fact, there were quite a few women who acted as evangelists for this lifestyle, as they called it. They spoke glowingly about how it had improved their lives and marriages, about how being hotwives (the term for a wife in this kind of relationship) had made them happier, and how about how being cuckolds had actually made their husbands happier.

One woman I chatted with via Twitter - let's call her Rebecca - was quite effusive in her praise of the lifestyle. However, she warned me to take it slowly, for jumping too quickly into the deep end could result in all sorts of emotional messiness that could very well ruin my marriage or, at the very least, create resentments that would fester in a really unhealthy way.

I spent close to a month obsessively gathering knowledge on the subject of cuckolding, which wouldn't surprise anyone that knows me. I can be obsessive. When I decided I wanted to learn how to make apple pie, I filled our kitchen with ingredients and spent the better part of a month trying out a host of recipes until I found the one that struck me as absolutely perfect. It doesn't work for me to do something that's good enough. I need to go above and beyond that. If I'm going to do something, then I want to do it as close to perfect as possible or it's not worth doing.

It was harder to find stories of cuckolding gone wrong - people don't tend to want to share details of their failures - but I managed to find them. As far as I could tell, the failures tend to fall into two categories. First, there's the marriage that was already on the rocks. The wife then finds someone else to have sex with, has great sex with him, mistakes the good feelings that come from sex with love, and leaves her husband. That kind of marriage was almost certainly going to fail anyway, but the cuckolding definitely pushed it over the top.

The second type of failure seemed to come from both the husband and wife (though more the husband, from what I read) being unprepared for the reality of cuckolding. It seemed that in the transition from fantasy to reality, a wealth of unexpected emotions came up. The most common version of this featured the husband basically freaking out, probably because cuckolding is, in a lot of ways, built around humiliation, and erotic humiliation can be heavy to deal with. There's a version, though, where the wife has trouble dealing with the emotions she feels towards her husband when she witnesses him getting off on being humiliated, even if it's in a very small way.

It was the second type of failure that worried me. Our marriage was strong and my love for Milo was - and still is - deep and everlasting. I was concerned about upending the rhythm we'd established in our eight years of marriage, though, and that meant I needed a plan.

I know this might sound bad, but I decided I was going to train my husband to be a good cuckold. To be fair, part of the plan was also to train me to be a good hotwife, and for the most part the plan really just involved taking things slowly so that we could both get used to the idea of making cuckolding a part of our marriage. After all, it's a big change.

The journey to the lifestyle we lead now wasn't entirely smooth - I wasn't expecting it to be, of course - but we've arrived at a really good place and I think we'd both say that we're far happier - and far more satisfied - than we were before. I've now become just like all those other women that advocated for cuckolding, so I figured Milo and I would share our thoughts on our cuckold training journey and the joys - and pains - that came out of it. I hope you enjoy it.

Milo

"I'm going to train you to be a cuckold."

That's how Avery announced she was willing to consider making my fantasy a part of our sex life. It was unexpected, to say the least. First, because she'd been awfully angry when I told her about my fantasy. Second, because we hadn't talked about it for at least a month. I just figured it was something that would never come up again. Then she told me she'd be training me to be a cuckold.

We were sitting on the couch and Avery was in a hoodie and a pair of leggings and she somehow managed to make it look like the sexiest outfit in the world. She said those words I mentioned above and I sat there in stunned silence for a few seconds before finally speaking up.

"What...wait, what does that mean?" I asked.

"Well, I don't have it fully planned out yet," Avery replied, "but I've done a lot of research on cuckold and hotwife relationships and if we're going to try it, then I want to do it right, which means you need to be trained to be a good cuckold, and while I'm training you, I'll learn what it means to be a good hotwife."

Okay, so, it was honestly exciting - sexually speaking - to hear her say that she was going to train me to be a good cuckold. Like, really exciting.

"So, as of right now, I decide when you get to cum," Avery then explained.

"Wait, what?" I asked, as I think any man would have when he'd been informed that he no longer controlled his orgasms.

"Orgasms are the enemy of effective cuckold training," she said. "Every time you cum, your desire disappears, and your desire is an excellent tool in training you to be a good cuckold."

Every time she said 'good cuckold' I could feel myself getting a little more turned on. It's like she'd found the phrase that triggered my mind to think about all the cuckold fantasies I'd had over the years, most of which involved Avery having really good sex with someone else.

"Will you have the self-control not to masturbate?" Avery asked.

"Yes," I answered, though I didn't give it even a moment's thought. I just agreed because I was so eager to have cuckolding be a part of my life.

"Milo, are you sure about that?" she asked, sensing that I didn't take much time to think about it. "Because I want to make it clear that this isn't the sort of thing where I'm going to be okay with you sneaking in a few orgasms here and there. If we're going to do this, we're going to do it right. I'm going to be in control of your orgasms."

She wasn't trying to be erotic, but I got really turned on as that sentence came to an end. I really liked the idea of her being in control. "I know," I said. "And I'll give you control. I will. I won't sneak off and masturbate. I won't break whatever rules you come up with."

"Just so you know, it's going to be a long time before I actually sleep with someone else, if I ever sleep with someone else, because there's no guarantee I will," Avery informed me. "I love you, Milo, and I have no interest in destroying our marriage just so you can live out your fantasy."

I shook my head. "I don't want that either. I don't, Avery. I swear."

Avery smiled and then scooted a little closer to me and gave me a soft kiss on the lips. She kissed me again soon after, this time offering the tiniest hint of tongue, which was enough to get me all charged up between the legs. It's amazing what a little taste of fantasy and a sensual kiss can do. I moved in for more after that second kiss. I put a hand on her waist and then slipped it under the hoodie. I went right for her breasts as I tried to offer the whole of my tongue, but Avery was having none of it.

"No, no," she said softly while backing away.

I was a little confused - why kiss me if she's not interested in fooling around - but I knew better than to complain. "Sorry," I said instead.

Avery moved back to the far end of the couch, sat cross-legged, and asked, "Your fantasy, it's about me having sex with someone else, right?"

I nodded. We'd talked about cuckolding a handful of times, but mostly I'd just said the same thing over and over while Avery alternated between looking angry and full of despair, so I'm not sure she ever really heard everything I'd said.

"And what kind of sex?" she asked.

"Great sex," I replied immediately. "It has to be, or, well, the thing that turns me on is the idea of you having great sex with someone else."

She smiled in a manner I found utterly irresistible. It was a little bit seductive, but also playful. "So, it would be fair to say that your fantasy is about my pleasure."

I took a moment to consider the notion and nodded. "Yeah, that would be fair. I mean, if you had terrible sex with someone it honestly wouldn't be the slightest bit arousing to me, so yeah, it's about your pleasure."

"That's good," Avery said. "I'm glad that's clear, and that I understand that. I'm going to make you prove it, which is why I'm taking control of your orgasms. You don't get to pursue your pleasure. Not even a little. I get to decide when you feel pleasure, and I get to decide when you cum. First, you can prove to me that you actually want your fantasy to come true. More importantly, if I keep you in an aroused state, it's so much easier to train you."

Now, I'd understand it if you read that and thought it seemed like a pretty fucked up thing for my wife to want to do. I mean, it sounds like a form of brainwashing if you think about it in a certain way, and I suppose there's some truth to that. The thing is, I didn't care. I just wanted her to cuckold me. More than that - and this is potentially kind of fucked up - I was actually really turned on at the idea of being trained, at her just coming out and saying that's what she was going to do.

"The first thing I'm going to do is institute a little game," Avery said. "And the rules are simple: You need to make me cum 10 times before I'm going to let you have another orgasm, and your cock won't be providing me with those orgasms. You’ll have to show me that you’re not constantly thinking about your cock. Do you understand?"

"I do," I answered.

"I'll make the first one easy. You can give me a foot massage for a little while and then I'll let you go down on me," she said. "After that, you'll have to work a little bit harder to get me turned on so I'll let you between my legs."

She put her feet in my lap, smiled, and then grabbed the remote and turned the TV on. I set about giving her a foot massage and counting down the minutes until she'd let me between her legs to give her an orgasm. I was excited about going down on her - I've always loved doing that - but I was also excited about the bigger picture. If I did what she wanted - if I let her train me - I'd get to be a cuckold. I'd get what I wanted, what I've fantasized about for almost all of our marriage but had been too scared to ask about.

So, at the start at least, I was all in on the training.

Click here to read part two of the story.