I’ve always been jealous of the variety of clothing options that women have. If they want to wear pants, they have all kinds of options there from jeans to silky and flowing. If they want to wear a skirt or dress, they can wear their hemline from the floor to just below indecency. If they want their underwear to show, that’s their option. What fun! And what control they have over men by what they wear!
I never really got much into full drag. I’ve mostly been just into wearing underwear and some feminine clothing that might tip off a woman to what I really am.
My need to be exposed to women as a crossdresser led me to massage parlors. The girls in these places would give handjobs to their customers. After some shopping around, I found the right girls who got into playing with me and feeling me up in my bra and pantyhose before giving me the “happy ending.”
Eventually I found one who became a little dominant with me and started fingering my little hole. The first time, I felt like a girl who had been fingered for the first time. “Oh my,” I gasped. “Yeah, you like that, dontcha baby?” I felt like I was being taken advantage of, and yes I liked it! Oh my goodness, it was as if my virtue was being taken away from me. You’re probably thinking, “What a priss!” Exactly.
Up until that time, I hadn’t experienced anything anal. When I was young, I used to put on girl’s underwear with the kid across the street, and he wanted to stick small things in my butt. I wasn’t much into it. But this was different. Now here was whimpering like a girl while this woman was jacking me off with one hand and finger fucking me with the other and talking dirty to me. “You like getting your pussy fucked like that don’t you? Don’t you?!?! You love it!” That pushed me over the edge, and I was cumming all over myself.
As I pulled my panties back up that first time I felt so dirty and naughty and sexy. What a girl! It wasn’t a week before I was at the adult bookstore shopping for a butt plug and a vibrator with an anal attachment. I was going crazy to have my little bottom penetrated again, and I was back at that massage parlor looking for that girl to “do me” again just like she did before.
I had made another giant step toward being a major sissy