Crossdressing Stories: Head of the Class (Crossdresser Stories Book 30)

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When a mother loses control of her urge to feminize her son, both of their lives change in ways they could not predict. He gave me a key, and said I could do whatever I wanted while he was gone. I could ‘hang out’ or whatever. He knew I was studying for a certification, and mentioned it would be a nice, quiet place to get away. Immediately I formed a plan, seeing this as a golden opportunity unlike any other I’ve had in a very long time. I already knew what I wanted to wear, and I couldn’t wait until late at night when I could leave home, go to this empty house, change into my female persona, and enjoy some ‘me’ time. When I awoke, Momma and my new Daddy were there, waiting for me to awaken, "Princess, how do you feel?' asked Daddy as he hugged me. A secret society of women dedicated to the total feminization of males sought to turn him into a woman… but his wife soon had cause to wonder whether Geofferson was honestly all that opposed to the idea.

I got everything together, making sure I had what I needed, including a spare pair of hose (always have a spare, I hate runs), my makeup, lube, and the rest of the outfit that I couldn’t easily wear under my man clothes. With that all done, all I had to do was wait…for two more days! That’s like two MONTHS for my level of excitement and anticipation. I wasn’t simply planning on dressing up and prancing around an empty house at night…I wasn’t planning on being the only one to enjoy what I would be wearing! This was new – and interesting. “I can do that. I’d love to help a girl, yes? “I hesitated, questioning, “learn all that.” He then slides his hands inside my dress. I was turned on immediately and my feminine senses go off the roof. We kiss each other passionately.One afternoon my friend, Bob called me and asked to house-sit while he went on vacation. The house was empty, save for a table and four very comfy chairs. It had been renovated and listed for sale, so it was all new, but empty. He asked if I could keep an eye on things, take calls from realtors if they called, and go make sure everything was okay. The infamous “costume gun” is used to commit a crime and fate reaches across time and space to bring justice for the victims. I then put on my wig, clipped on a pair of dangly earrings, and slipped into my Mary Jane heels, my legs looking hot as they maneuvered into the shoes. Looking at myself in the mirror, I was exploding with feminine sensation throughout my body. I would so love to go out like this any time I wanted, day, night, to a mall, Wal-Mart, around town…but obviously, that’s not a reality. A covert deep-cover assignment leads an author and his wife to swap identities. The man’s efforts to lead his wife’s life leads to complications he never imagined—and a deadly game of spot-the-assassin! In the future, everything will be “smart”: a woman’s vanity, breast forms, wigs, and even a cross-dresser’s prosthetic vagina…

Winston Ashborne needed a cure stronger than hot soup: a tight skirt, a makeover, and an evening out—as a woman. Would he be a good boy and take his medicine? A cross-dresser in deep denial comes to terms with his desire for feminization, and meets his fate at last on Halloween night. A couple use the AutoMesmerizer to spice up their marriage, but their roleplay takes them further than either ever intended.A cross-dresser with a very understanding wife finds out just how accepting of his lifestyle and his womanhood she really is (and there’s a bonus caption to boot). A young man finds himself the subject of an old witch’s efforts to revenge herself upon his father—in pretty much exactly the way you might expect. I fought them as best I could, but I got brained and cut several times before Reg and our parents crashed through the door before I passed out. I got away with being a girl in school, that way and met my future husband Reginald 'Reg' Van Dyke as well as the school's delinquent gang. The gang was in general led by some adult who made sure that the gang’s fines were paid. No one knew who it was until it was too late to help me, but now the entire gang is in prison where tougher convicts are having fun with their new friends. In the face of alien invasion, all that stands between the Earth and certain destruction is an intrepid band of cross-dressers with nothing left to lose!

My name is Roger. I am a 29 years old, white, a little skinny , and a married (secret) crossdresser. I really love wearing women’s clothes and I am crazy about pantyhose (and tights. I love the total coverage and the sensation that pantyhose gives me.A young man is feminized in a unique way, as he seeks to emulate—in every possible way—his gorgeous aunt who seeks to exploit him for her own gain. I saw her take a deep breath and ask “Sometime would you help my young daughter to buy some proper teenage clothes, dresses and so on?” Sarah is a woman like no other, with the beauty of a harvest moon and a past she refuses to discuss. She will take all that you have to give. She will change your life.

A cross-dresser finds out that he has a lot more in common with his mother than he ever thought possible, and vice versa. I eliminated most of the replies and narrowed it down to two that seemed promising. One of the ‘finalists’ was only available that night, which was not possible, so now I was down to one. I was hoping this would pan out. I’d hate to miss out on this opportunity. I only had a few days. So this last prospect sounded really serious. He just needed 20 minutes notice to get there, and promised he would show up. Believe it when I see it, but nonetheless, I was pumped, excited, nervous, scared… all the normal emotions I always feel when arranging a meet up with a complete stranger. Then Aunt Lily opened the pit for me to fall in. “Morgan dear, Miss Martin would like to be shown the new range of dresses from Avventura. If you can be ready as and when, mmm, yes?”The government has a way of dealing with cross-dressers and it isn’t… well, actually the results ARE actually quite pretty indeed! Out of the blue, Auntie offered me a job. It would be my first time far from home. A new life, new opportunities, new people, new everything. The dress-shop was old-fashioned, like most clients. Away from the city-centre, an area a little neglected. Again – like the clients. But it was a big shop with a full range – from teen to old-lady. From short, to tall, to, um, large.