Fiendish Confessions

I met Tim in a chastity chat room about a year ago. He's a bit younger than me, and goes to school in California. He had little exposure to chastity beyond some cuckold* fantasies, and basically no exposure to BDSM. Even though he's straight, he took an immediate interest in me. I told him early on that we weren't a good fit for each other, but he never stopped flirting with me, and to be honest, I enjoyed shooting him down time and time again. In spite of this, we talked frequently over the following months while he struggled to understand the urges he was feeling. A few months later he came to me extremely worked up. He had denied himself for four days as an experiment. I wasn't intending to play with him, but there was just something about his mood, and the way he started talking. . . I started by having him bring himself to the edge of orgasm and stop. Even though we were using a primitive text-based chat system, I could sense his desperation, and it drove me to p...

Being a Dom comes naturally to me; I have a constant urge to push people, seem to have some skill at it, and enjoy doing it. That said, some parts of the job are harder than others. One of the hardest, and most important to do correctly, is reading and understanding a sub. The kind of play that I enjoy involves creating a sense of powerlessness. That means making a sub do things they don't want to do. I will apply all sorts of pressure such as charm, pain, guilt, fear, frustration. Sometimes I even use force. This is fun for me, and if I do it right, it'll scratch that deep down submissive itch inside of them. If you push a sub too far however, or push them the wrong way, things can get ugly fast. You have to be constantly reading your sub when you are playing, looking for those subtle (or not so subtle) clues about their mood. The signs that people show vary widely, and mean different things. Some people beg, some people cry, some people talk, some people even laugh, and...

Starting out as a Dominant isn't easy for a lot of reasons, but the hardest thing for me was learning to deal with the guilt. I have always had a strong moral code, and like to believe that I'm a decent person. Accepting that I not only enjoy, but actually need to make others suffer to be happy in life was really tough for me. From talking to other Dom/mes, I know that I'm not alone. A submissive has to admit that they enjoy being tormented for the pleasure of another. This is not easy either, but it's not a selfish pleasure. A sub is doing it for someone they care about. It is a noble gift, strange to an outsider perhaps, but it's not like they're hurting anyone. I hurt people. I enjoy pushing someone to do the uncomfortable, to sacrifice their own pleasure for the sake of my own. What I do is clearly unreasonable in a free society that values equality. This was difficult for me to deal with many years ago, but I got over it. I forced myself past it. A tr...

We have been experimenting with keeping C in chastity for the last month, but have finally had to stop. It's been frustrating, but I have learned a lot from the experience. For the benefit of others, and myself in the future, I can condense everything I learned into these small nuggets: To reduce chafing in a captive ball device: the tube should be small enough that it is usually full, the A ring should be small enough that it's never loose, and the whole thing should be as small and as light as possible. This will reduce the amount that the device will move while being worn. The A ring should also be loose enough that when the tube does move it slides over the skin rather that rubbing or tugging it. To securely lock someone in a captive ball device: the gap between the A ring and the tube must be small enough that the balls can't fit through, or the A ring has to be small enough that neither the penis nor either ball can come out while it's locked in place. The gap in...

C has been doing really well as our first houseboy. He's been coming over about twice a week, which seems to be a good pace. He does a few basic chores every time he comes over: change the cat litter, sweep the floors, do dishes, and clean the kitchen. Once a week we add some other chore like wiping down the counters or cleaning behind the stove. It has made a huge difference. Our home looks so much better now than it used to. I had worried that I would stop doing chores if someone else started, but I'm doing just as much as before, even sometimes while C is doing his. The difference now is that I am doing different ones that used to get put off. My office is more organized, computer chores are getting done, and I've made progress on a few little projects around the house that I've wanted to do since we moved in. This may change if I get more accustomed to a house boy, but for now the result is fantastic. In terms of kink, it is a strange one. I don't fantasize ...

Chastity has been one of my goals for C from the very beginning. Not only am I a big fan, but it's one of his main interests as well. I tried putting him in a "The Curve" I have kicking around on his first visit, but the largest A ring I have wouldn't fit. The A ring is the main ring that goes around the balls and base of the penis. It is essential to holding the curve and all it's cb-x000 brothers in place. If it's too tight it can cause pain or chafing. If it's too loose, the whole thing can slide off. At first I was discouraged, but by his second visit I had the idea to try ball stretching. I took a bit of cord and wrapped him up, enough that it would start to feel tight when fully erect. It looked awesome, and gave him a sensation of being marked, but the knot fell apart on his trip home. I had him re-tie it, which worked out for a while, but he started having circulation problems so we had to stop. I also tried using tape, but that didn't wo...

After years of searching my wife and I have finally found our first houseboy. He came over this week to start his training, and so far it has been a lot of fun. It's been difficult to find someone. It's not enough that they be interested in domestic service, there's all the other standard challenges: local or able to relocate, compatible with our kinks, compatible with our personalities, have the time to serve, and have the courage to show up for the first time. So when one day, after years of being stood up, abandoned, rejected, one shining candidate shows up at the door and offers himself to be used, it's magic. C is fairly new to kink, but he is serious, and well suited to the role. He's honest, clever, polite, and extremely cute while kneeling waiting for orders. The most important part, as is true for any kind of service role, is he seems to get that warm fuzzy feeling when he is able to make others happy. More than that, he seems to need it in his life,...