How it started for me
My story might be a little different..i wasn’t sissified until later in life in my 30s. Ive been bi since my teens, but more women then men. Regardless of their sex, I found I get off on getting my partner off, especially oral. Id rather eat pussy or suck cock to their orgasm and satisfaction than get off myself.
I met a man online who was dominant and liked training sissies. He was older (much) and lived near by but we didn’t actually meet for a long time. Instead he trained me and turned me into a sissy. He would give me tasks to do..maybe a video to watch or an article to read, or something I had to do. Like tuck or wear panties. I had to report back to him after each task. He wanted to know how it went, and how I felt about it. Things progressed well. I was now smooth, wearing panties, playing with dildos and chaste except when he gave me permission to cum.
Even though he was a stranger on line I gave myself to him. Things progressed nicely. He had me doing more things in public. He would task me with going panty and bra shopping . He also had me buying outfits at second hand stores. Some were very fem and strictly for home wear but others were more androgynous like girls shorts or tops. Then he would have me in a panty and bra wearing these shorts and tops out in public. Fortunately I didn’t live near where I worked or had friends. But it was near an “active adult” community..a “target rich” environment of horny older men.
Now I had to dress up and go shopping, walking and positioning my body in feminine ways, or visit a bar for an afternoon drink with the men around me. He had me learn to flirt and was so happy when I would get a phone # of a guy. I had to report all of this to him. What they looked like, how they acted toward me, how I felt about possibly sleeping with them. Remember of course that I have “slept” with men, even a few older ones,but I had never done so as a sissy. So I did find a guy I really liked. He hit on me in a grocery store and I got his number. We met later for coffee a few days later. Ordinarily I probably would have gone home with him but now I had to have Daddy’s permission. So I did and arranged a date and dressed up for my first encounter with a man. And it did NOT disappoint.
My dom daddy and I finally met after that and things got weird. I met in a parking lot and rode with him to a secluded area. Turns out he can not get hard or cum anymore (although I sucked like crazy trying) and he was also into some bdsm. Like tying me up with the seat belt and spanking me and finger fucking me. That was ok but then he went off on how he was going to find guys on line and send me to suck or fuck at random. On the way back to my car he was telling me he planned to take me to this gay campground and he was going to make me do anything he wanted with any random guys or group of guys. I could not refuse anything Daddy or the men wanted. Im not so sure prostitution wasn’t part of the plan. Now it was a powerful fantasy to be Daddies whore but was just too risky for me for several reasons. We parted ways when I refused to do any of this.
I was sorry that it ended as I enjoyed his guidance and my discovery of this lifestyle. Had he been less over the top I wonder where it would have gone. But I grateful to him for turning me as I found out I really enjoy being a sissy.