Cuckold Training

Becoming a cuckold was never one of my  fantasies in the beginning. It wasn't until Mistress planted the seeds of that fantasy in my head. I won't go into detail on just how she managed to do that, now. This is, instead, the story of how she used one of my fantasies to train me to be her bi-sexual slave. Thus priming the pump (so to speak) in preparation for my becoming her cuckold.

My original fantasy was to be used along with another male slave for humiliation and possible forced bi-sexual activities, eventually. The first time Mistress told me that she had found another male slave that she wanted to bring into some of our sessions, she told me that if I didn't approve of him, she would try to find another. We met at a quiet restaurant where we could talk, discuss some possibilities, and get to know one another.

By the time the meeting adjourned, we had all agreed that the terms of Mistress' proposal would be acceptable. Basically, we had agreed that Steve (the second slave) would simply join our sessions once a month (at first) and more often if things went well during those first few sessions. Needless to say, they went very well.

In our first session with Steve, Mistress made us both undress completely for her. We were both told that in future sessions we would be expected to be naked and to wear collars with leashes attached. During the first session Mistress made us a deal. We were both to masturbate for her, but only one of us would be allowed to cum. We would then both be locked in chastity devices for a month. Steve came first. We were iced down and the cages placed on out cocks. The “loser” (me) was then allowed to watch as Mistress fucked the other (Steve) with her strap-on. Then Steve was sent home.

One month later, when Steve joined us again, Mistress used her hand to masturbate us both. She lubed our cocks up and had us stand beside her chair while she stroked our cocks. Again, the first to cum was fucked with the strap-on by Mistress while the other watched.

The next time, we were lubed up by Mistress but then we had to masturbate each other. That was both very exciting as well as very humiliating! We were placed on the floor in a sixty-nine position so that we could easily reach each other's cocks. We were told that the first to cum would have to watch as Mistress teased the other one's cock for an hour. What we were not told is that the “teasee” would not be allowed to cum. The fact is, I was always the last to come and it had been several months since I had had an orgasm.

Let me tell you, it was a very strange feeling having to masturbate another man. I had only touched another guy's cock once in my life and that was not a sexual thing. Steve's cock felt very different from my own, even though we were both uncircumcised. His cock was not only thicker than mine, it was longer by about an inch, as well.

After that session, Mistress decided that Steve would join us once a week for extended sessions. During these sessions, Mistress would use us both in many ways. Sometimes punishing one or both of us, paddling or flogging us, fucking us both with her strap-on and, of course, making us masturbate each other rewarding the one who lasted the longest with an hour of teasing.

Eventually, Mistress changed the rules. Whoever ejaculated first, in these sessions, would be fucked by the other. That is, whoever didn't cum during masturbation, would then fuck the other in the ass until he come. Eventually, that changed as well. Mistress would play with both our cocks simultaneously and the first to leak precum would be locked up and would have to be fucked by the other. Of course, that meant only one of us would get to orgasm during a session, no matter what else Mistress might do to us.

Our final humiliation came several weeks later when the rules changed again. Not only did we have to masturbate each other, but the first to leak precum was forced to suck the other's cock. This was my first truly bi-sexual experience. The first week I was on the receiving end as Steve leaked first. But in the weeks that followed, I was often the loser and had to suck Steve’s cock. But managed to win a few times.

Now, as to the cuckolding... Eventually Mistress changed the rules to include herself. The winner, the one who took longest to produce precum, was allowed to fuck Mistress. Of course it was always done on her terms, the way she wanted to do it. But the fact remained, I was now a cuckold. I didn't mind. I always got teased and sometimes got fucked, but the fact that there were times when Steve would fuck Mistress didn't bother me.

I don't know if this would work for everyone, but it did seem like a very gentle way to introduce cuckolding into our relationship.

nemo