Sissy Training 1

I am a blue collar manager type and live a pretty work a day life during the day, but at night, I have a rather interesting sideline. I am a sissy trainer. You see, many sissies are married and end up coming out to their wives. To most couples, this just creates a fun little fantasy for play during sex, but for some, it becomes more. For these couples, at some point along the way, they find that they really don't know how to go beyond the fun little panty play and maybe the occasional spanking. They don't know about training a sissy properly. They research and look at blog sites and even watch porn clips dedicated to this. Then they find my ad online, offering my services. The ad header reads something like: Sissy training coach available. I have run this ad several times, and have gotten a number of responses. Some from the sissy, and some from the wife. I have had a lot of fun putting these pathetic little faggots through their paces. Usually, it ends with a one night stand where I meet up with the couple, play the big, macho stud that they both fantasized about, let him suck my cock and, if I'm lucky, I get a nice piece of ass. Maybe his, maybe hers. Last week though, I got a response that changed all of that.

It started out the same as all of the others. The sissy contacted me and said he was interested in playing. I'm thinking to myself "how original" but I play along. As the emails progress, he talks about his fantasies, all similar to what I've heard before and I'm thinking, OK, same thing, different day. I start asserting myself. Asking him to do things. Testing his willingness to bend to my will. All is going well and I'm thinking that we can have a nice little hookup here. Then, I ask him to introduce his wife to me. He allows me to start emailing with her. Almost immediately, something seems different than the other times. She seems very committed to her sissy and his training and we seem to really click as well. Suddenly I'm thinking, hmmm, I guess I'm gonna have to see where this one goes. Step up my game a little. I begin to probe a bit deeper. Asking more about what level they are at and where they see this going. As we explore, she relates to me that her sissy has had a breakthrough. He said this had become much more than the role playing, one night thing they had imagined. Perhaps this was going to become a lifestyle change?

Ok, I say, I can handle this. I can't say as I have ever had a "lifestyle sissy" but, hey, I'm a professional sissy trainer, right? We set up a meet and greet to talk about what I can do to help them in their journey and what boundaries we will have. It's really more of a formality at this point as I have already had many discussions about this with "Lady J" but sissy doesn't know much about those conversations and we still haven't met face to face.

The big day comes. We pick a local bar where we can be anonymous and hear each other talk without being overheard. I arrive early, find a table and order a glass of wine. A few minutes pass and I see a couple come through the door that match their description. They scan the room and see me and I wave them over. I have seen some pictures of them both but, when I see her, I am taken aback. She is really stunning! She says hello and I can hardly reply. We all sit, make our introductions and get some drinks on the way. I make sure I get her seated by me since Sissy has only a small role in this meeting. Talking with "Lady J" I find that she is everything she appeared to be when we were chatting online. She is thoughtful, intelligent and, well, sexy as hell. We take some time to address sissy's concerns ( like they really matter) and, previously unknown to him, present him with his sissy name. He is elated!

Things go well, they like me, I like them and we set up a "session" for the next week. I tell her that sissy has the proper attitude, but needs a lot of work! She is impetuous, unrefined, and still way to independent. In the days to come, I will be sending sissy daily emails outlining his homework assignments. Among them, to wear the sissy chastity cage we have presented him with. He is not to touch himself, and can only be out of the cage when Lady sees fit. He will wear what is laid out for him and will be available for inspection at any time. He will receive daily spankings to help him stay centered and to make him more "pliable". Until our next session, he is not allowed to pleasure himself with his pathetic sissy stick. Rather, he is to begin pleasing himself anally. After all, this is the only way a sissy should achieve orgasm.

All the time I am making this list, I am thinking to myself: this is going to be fun. I am going to make him into such a pathetic sissy that Lady J will never want his pathetic dick again. Instead, she will seek out my superior cock for her pleasure. If I play my cards right, I will have a fun little sissy who will suck me off or let me pleasure myself in his sissy ass and , I will have a sexy, dominant female partner to satisfy my more "consequential" needs.

I can't wait till next week. Let the games begin!