I have been an on and off crossdresser for as long as I can remember, but never get enough time to dress, and use every opportunity that I'm alone to explore and push myself even further. Some of the best times that I'm able to dress is when I am away at conferences, I'm able to dress privately in my room without anyone interrupting me but fantasize if someone did. Knowing that I had a week away coming up, I started to plan my week and potentially push things a little further.It all started with a simple post on FetLife, "Local Sissy seeks Master/Mistress for a Week" in a sissy based FetLife group. I didn't receive tons of responses, I was looking for a Master/Mistress that could meet me on my trip and help push me to my limits. I did receive one direct message from a local Master that was interested in helping me for a couple of days, we chatted a handful of times and started to plan how the week would go. We talked about bondage scenarios, ass play, humiliation, gang bangs, dinners,. “You did,” I laughed, unlocking the door and leading the way inside, locking it behind us so we wouldn't be disturbed. “I'm sorry, what was your name again?” “Judy. Judy Warren,” she replied. “Okay, Judy, this is a very informal type interview, mainly because I don't like all the formalities of big business. As you can see we're not a big business, in fact, we're just a little thing just getting started. So let me be upfront and tell you, we may fold instead of taking off.” “Oh, I hope not. I'd like to see you make a good living at this, and me along with you,” Judy interjected. “Good answer. One point on your side,” I laughed. “How do you feel about working for a woman?” “Not a problem. In fact, women understand a lot of things so much better than men. Like my boyfriend just doesn't get it that there are certain times of the month when I don't want him to even touch me even though the day before I was all over him.” “I know exactly what you mean, although I don't have that sort of.
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