It started out as a normal session with my mistress. I had finished my week's job as a software engineer and driven over 50 miles from my residence and town of employment. Her emphasis in previous visits had been on her humiliating me verbally or physically and more and more questioning me of my fantasy life that I, of course, thought would forever remain as just fantasy.
I was wrong. Completely wrong.
She ordered me to strip out of my clothing, which was a normal procedure for our sessions and then she announced that I was going to be the "entertainment" at a garden party. As I was processing her words she handed me an outfit that I was to put on. It was time, she said, to put some of my fantasy life into real life, to not ask questions and just do as I was told.
I had never had an interest let alone worn women's clothing but my "outfit" was a black, see-thru thong pantie, a black see-thru bra that was equipped with large -- I would guess a D or DD size, - silicon breasts complete with protuberant rose colored nipples. She added a tight, corset like, waist cincher that gave me an instant female shape. After I donned this lingerie she placed a blond wig over my hair, had me get into a black pair of high heel "fuck me" pumps complete with ankle straps. She aided my walking around in the heels until I wasn't teetering too badly. She remarked that they were not stiletto heels as she didn't want me to sink into the ground. Her comment only led me to be even more contused with her plans for me.
She completed the package by putting on a thick coating of whore red lipstick on my lips. She took a couple of pictures of me in this get up with her camera in spite of my being almost numb in surprise at her actions and feeling a little silly in the woman's clothing and both nervous and excited at what might be in store.
She kept me waiting as she went into her bedroom and several minutes later emerged wearing a gorgeous long evening dress, in scarlet silk, that was long at the bottom going to her beautiful ankles but very short on the top as her gorgeous bust line was clearly defined as the strapless top just barely covered her protruding nipples. When she walked toward me it was also evident that the dress had a side-slit that went all the way up to her waist and flashed a very tantalizing view of her long and beautiful leg.
It was approaching early evening as she led me to her garage and put me in the back seat of her Mercedes, which was itself a bit difficult with my high heels. She had me sit exactly in the middle of the seat so that she would be able to keep a constant watch on me from her rear view mirror. She said no matter what occurred I would keep my arms out to my sides and not to touch or cover myself in any way. She then produced a leather blindfold which she placed over my eyes.
We backed out of the garage, she hit the button to close the garage door and proceeded out of her housing area. We made several slight turns as well as several corner turns at various intersections which soon had me completely disoriented as to what direction we were traveling.
While it was getting later in the day it was not yet sundown. We proceeded to an intersection with a stop, I presumed we were at a stop sign or stop light and based on the sound of several cars, we were about to enter a major road. She exclaimed, "oh, I almost forgot". With that she hit a button and suddenly the top of her convertible came open and settled itself into the boot and I realized I, as a blindfolded crossdresser with large boobs and see through panties, was instantly on display for any that cared to look.
I pleaded with my mistress to please put the top up as I was horribly exposed as well as totally humiliated. Her only comment was to be still as I was making it difficult for her to concentrate on her driving.
For the next twenty minutes or so we proceeded down several roads with many cars noticing the blindfolded and barely covered, large breasted "woman" sitting in the middle of the back seat of a convertible. The honking and several shouted insults were leaving me nearly petrified with embarrassment and yet, strangely excited as I knew I had admitted to my mistress of a fantasy desire to be exhibited.
As our drive ended we turned into what I guessed to be a circular drive and from the immediate voices I heard a valet opening the car door to let the mistress out and then came around to the other side to take my hand to aid my exiting the car. I realized I must be at a home large enough for a circular drive and expensive enough to have an evening valet aiding the parking. My mistress stopped me long enough to "refresh" my whore red lipstick. Then I was led apparently around to the side and then to the back of the house where I could hear from several conversations that many people were attending a garden party. From those conversations and then greeting us it was obvious that I and my mistress had made quite an entrance.
The next hour was surreal with blindfolded sensory input from a situation completely out of my control and completely new to all of my experience. Always in the back of my mind was the huge question of would anyone at the party know my identity. I lived an hour's drive away but based on the sounds it was a somewhat large gathering and with my job and travel I had met many individuals in the last several years. I hoped my "disguise" of the female body shaping, wig, smeared on lipstick and eye mask/ blindfold would make it more difficult to recognize me. But the trepidation of being outed as a submissive exhibitionist would remain. And, as the evening wore on, there was an even bigger "outing" that would occur.
Off and on I was led around the area where various people commented on me, some complimentary, some raunchy, some denigrating me as a pervert to allow myself to pretend to be a woman, even though, as they would remark, I did have a great set of tits. Off and on my mistress would order me to stand still while she would proceed to walk away to talk with other guests, have a glass of champagne, etc. While standing by myself I would occasionally feel hands, apparently both male and female, touching me in intimate areas, and in spite of my total consternation at the situation, causing a rise in tumescence of my cock.