Let me tell you about a crossdresser’s public humiliation. I am a Femdom phone sex Mistress primarily based in the United Kingdom, but I like to get over State side every now and again. Back home, I have a crossdressing chastity slave who sometimes can break away from his boring old desk job and come over with me.
Usually, we will go about our business as usual when we are here with him in male clothes for the most part, albeit with a pink bra and panty set on over his male chastity belt that makes him sit down to pee. But we do like to go on holiday out of the city or even state we are in. Those are the times I engage in a little erotic humiliation and punishing my slave, who happens to be my sissy husband.
We found a few places that cater to our demographic here, which is to say kink bars, and I have brought him out dressed to thrill on those nights. Of course, I tend to not look so shabby myself. We met back in college and moved in together senior year.
When we finally had gotten our flat, or apartment, I began the process of feminization, and while it was normally done behind closed doors, we had discovered fetish clubs the summer after we graduated. This was back when he was my fiance and had just recently become my collared slave–before that he was my submissive, and before that my boyfriend.
However, I was chosen to go across the pond to America, and participate in a semester at a college that shall not be named here. During this time, we participated in plenty of guided masturbation scenarios, drawing on my training in phone sex, to keep the spark alive over the long distance.
Finally, he was able to secure two weeks to see me over here, and I could not be more excited. The first few days we never left the bed, and I do not think either of us wore clothes. After that, I took him to meet a few friends, dressed in his usual sissy housewife attire which was generally a floral dress, pearls, a wig, and some make up.
I thought he looked gorgeous, but I was biased, after all. I had decided when he told me he was visiting, that I would take him to one of the kink bars here and try to pass him off as my hot girlfriend. We had talked about this idea, and he said it would humiliate the hell out of him.
I took him out shopping because no one would believe Holly Housewife would be at a club, and we bought him a leather miniskirt, fishnets, and a really cute blouse. To top it all off, a wig in a matching hair color as his Donna Reed looking one.
I figured a little continuity in hair color would be fun, even if he was tarting it up a little. We added sissy makeup, and a pair of pink heels, and I thought he was stunning. We got our jackets, both made for women, of course, and headed out for a night on the town.
On the way, I decided to stop at a bar near a neighboring college a county over. He did not know what to make of this. I simply laughed and said this was the acid test. Over at the fetish bar, they expect sissies and crossdressers, but here they will not be. We were going to go in there for thirty minutes and see if anyone hit on him.
He tried to talk me out of it, but Mistress always wins, after all. Luckily, I had him practicing a more feminine way of speaking while dressed, and he had it down pretty well, I thought. Well enough to fool a few drunks, I hoped. We grabbed our purses and walked in.
He wanted a corner both, I wanted to sit at the bar. We compromised and sat at a table, but I informed him that he would be fetching our drinks. Three cosmopolitans later, the waitress came by with another for him. He looked up at her, confused, and said he did not order it. The waitress said it was from a guy over at the end of the bar.
We looked at the guy, who smiled and raised his drink, and we both had two different reactions. My fiance was blushing, humiliated at the scenario. I, on the other hand, was thrilled, and more than a little turned on. I had my fiance approach the man with a drink in hand, and thank him.
I still do not know what was said, but the two seemed to hit it off. I ordered another drink, and I saw that man grab my fiance’s ass. I laughed and knew I was going to use this as fuel for later. My fiance just smiled and seemed like he was making an excuse to leave, but the man had none of it. The next thing I knew, the man kissed him on the cheek, laid a card on the bar, smiled, and left.
My fiance grabbed the card and came racing back to me. On the card, there was a number. I smiled happily because tonight was a huge success. My fiance was utterly humiliated, and I was reaffirmed in my talents as a Femdom. All and all, crossdresser’s public humiliation mission accomplished.