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While my Mother and Aunt were dressing me, I would exit the residences and walk through town. Usually, my walk started with me dressed in a full slip, garter belt panties, stockings, makeup, wig, and heels. Designers make the most beautiful and feminine full slips with lace bodice and lace trim at the hem. Typically, the slips were white or black, but I had a full pink slip that I enjoyed wearing. Of course, the red slip was reserved for Friday or Saturday night. The night air was wonderfully cool. My tiny clit made a dimple in the slip. After walking for some time, I removed the whole slip.… Leer más

I needed an injection in my hip bone for arthritic pain relief. I was informed that it had to be done under X-ray. My spouse and our female companion dressed me in a feminine pink lacy bra, full slip, pink garter belt with six straps, pink stockings, and an open strappy back pink panty. They tied my sissy clit and testicles with pink silk ribbons. We assumed at the hospital that I needed to change into a gown in a private dressing area. In the X-ray area, I signed the necessary papers. I was told a female doctor was performing the procedure. How embarrassing to have another woman see my tiny… Leer más

My spouse and our female companion love to host house parties. I am the sissy maid: model and sex toy. We host six to ten females. I am blindfolded the entire time. One type of house party consists of modeling clothing and lingerie. An auction is held for me to remove various clothing items. All money is donated to charity. The primary function of the auction is to get me out of feminine outerwear and just wearing lingerie. I must walk among the ladies permitted to touch the clothing or lingerie I am wearing. Since I LOVE my sissy clit tied with ribbons, the auction stops once my clit is exp… Leer más

My spouse knew that I was a crossdresser and submissive to women while we were dating. She enjoyed dressing me in lingerie. We shopped together for lingerie for me. She commented that when I was dressed, our lovemaking was more enjoyable. I pleased her by performing cunnilingus on her. My clit stayed harder for more extended periods. She told me that I always wanted to make sure that she enjoyed sex. We went to various strip clubs and adult cinemas. If amateurs were performing at a strip club, my girlfriend (spouse) was willing to perform. I did enjoy watching her perform. We were interest… Leer más

My spouse, our female companion, and I have traveled several times to an Adult Bookstore and Cinema. Since joining Xhamster, I have enjoyed videos of crossdressers and sissies in Adult Bookstore and cinema. Genetic women have always dressed me, pegged by women, and submissive to women. While in enfem, we went shopping, to restaurants, and cultural events. I always have a butt plug in place. My spouse or our female companion remotely controls some butt plugs. The butt plug vibrates or provides an electrical shock. We talked, and I felt that I might want to experience a situation where female… Leer más

My Mistress had used me in her dungeon on various occasions. I enjoyed being the center of attention as she used me, and others watched. My Mistress suggested we visit an exposition for Mistresses, Domontrix, and Masters. My Mistress told me to dress slutty for several days. My Mistress planned to display me at the expo in several different situations. My Mistress picked me up as planned. I wore a tight-fitting blouse with a contrasting bra, miniskirt, garter belt, stockings with the welt visible as I stood up, and CFM heels. I thought my wig and makeup were perfect for the drive. I never as… Leer más

I was checking various publications where I lived. I wanted a Mistress to sissify me, feminize me, and maybe humiliation. I found a Mistress who explored many sexual fantasies. We agreed to meet at her residence. She told me that I had to be dressed as a lady but willing to expose my clit to her before she would permit me to enter. She informed me that she had a dungeon that I might enjoy. I told her a few women had seen me wearing lingerie and dressed enfem. I told her that I had a tiny sissy clit which I wanted ribbons tied around my testicles and clit head. When she opened her door, I disc… Leer más

The second sales associate I became friends with offered various new experiences. When I first came to her store, she asked if I was purchasing for myself or another person. I told her that everything was for me. She asked what style I like in dresses and lingerie. I told her I enjoyed lingerie more than dresses, so sexy lingerie was essential for me. She helped me select some items and told me to try them on. While I was trying on items in the changing room, she knocked on the door and offered help. I told her I thought that I was okay. Within a short time, I heard the knock again. She asked… Leer más

I dressed more often in various cities and became more confident about dressing. I enjoyed two dress shops in a town on different levels of an outside mall. An exterior stairway connected the two levels. I learned the wind rushed through the stairway and played with my dress or skirt. It was thrilling to feel the wind play with the hemline. I did not try to keep the skirt or dress from floating up. I love silky broomstick-type skirts. These skirts flowed well with me. I did not wear slips with these skirts, which made them transparent. My other favorite skirts are miniskirts. No skirt is too… Leer más

My Mother's sister came to our house to talk to my Mother, whom she (my Aunt) had caught looking through her lingerie. I was a young boy (around five or six). My Aunt saw Mother and me dressed in our lingerie. My Aunt told my Mother she understood my interest in her lingerie. My Aunt was a beautiful woman with an impressive figure. Her breasts were huge and always had my attention if she bent over in front of me. My Aunt was very receptive to my crossdressing. She babysat me several times. She made sure that I was dressed in feminine lingerie. Also, she made sure that I saw her dressed in li… Leer más

My first job involved a lot of travel and staying in hotels. When I arrived at a new destination and had completed my business, I checked for dress stores that permitted crossdressers. I always called the company since I did not wish to cause them or myself any problems. I went to the store and made purchases. Many items did not fit properly back at the hotel, and I was leaving the next day. I decided I needed to advance to the next level of crossdressing and try clothing while in the dress store. I asked to try my purchases on after I had purchased the items. Sometimes, I tended to get the… Leer más

My Mother started crossdressing me at age four or five. My father was deceased. Mother dressed me in her panties. I loved wearing her panties. Her panties were silky and felt nice caressing my clit and bottom. I wore only her panties around our house and property. When Mother put me in my wading pool, I knew the white panties had become transparent. I loved the way the panties clung to my clit. I asked Mother why she made me wear her panties. My Mother told me that she wanted a ***********. She planned to keep me as a girl. I did not mind being a girl for my Mother. My Mother bathed me and… Leer más