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

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I push Samantha to go and he leaves immediately. Now, I had to face Bob and explain everything to him. I was never so embarrassed in my life. Bob had calmed down a bit. Then, I sit down on the chair and with a deep breath, I start explaining everything to Bob about me being a crossdresser and what I had planned to do this evening. Bob then comes a bit closer. 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.

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.

Then, he puts his hands around me and unzips my dress. I feel very submissive at that moment; Samantha was really good at this I thought. Then he grabs my fake breast and the sensation was something I had never felt before. He gets me out of my dress and makes me sit on his lap. He then starts caressing my legs and my chest very gently. Great story. I thought it was going to turn out to be Bob who was the visiting tv. That might make a good alternative ending. 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! 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. But there’s still a long way to go, which is why we’re grateful for each new trans narrative that enters the canon — particularly in the form of fiction, an obviously massive category in which trans authors have long been excluded from the mainstream. Charming yet incisive YA like Kacen Callender’s Felix Ever After and Aiden Thomas’s Cemetery Boys are setting trends and redefining expectations for YA readers and writers everywhere. Meanwhile literary novels like Binnie’s Nevada are a breath of fresh air in a convention-bound genre, shedding light on the trans experience while remaining accessible and entertaining to cis readers as well. Where can you read more stories by trans authors?

A family receives a threatening note, unsigned: feminize your son or you will all die. What do you suppose they’ll do?We go inside and sit on the chair. We start our conversation by telling each other a bit about ourselves. He tells me her feminine name is Samantha and he has been cross-dressing for the past 10 years. It was really exciting to have another crossdresser to talk with. I was really enjoying the moment and I had a lot in my mind about what to do next. But then, all of sudden, he comes really close to me and kiss my lips. 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?” A young man becomes obsessed with transforming himself into his gorgeous twin sister, but he takes the effort one step too far—with tragic consequences. 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!

He cross-dressed to please his girlfriend, but Jeremy would soon discover that Jasmine was born to wear a skirt… 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. An experimental story with a focus on atmosphere. One reader at TG Storytime mentioned its “surreal, dreamlike quality”, which is exactly what I was aiming for. A cross-dresser in deep denial comes to terms with his desire for feminization, and meets his fate at last on Halloween night.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!

The infamous “costume gun” is used to commit a crime and fate reaches across time and space to bring justice for the victims.

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. Auntie owned a dress-shop. Yes, I know now that’s the introduction to a whole sub-section of transvestite literature. I didn’t know it then. All I knew was that my mum had a sister in faraway Leeds and they rarely met, rarely spoke to each other and in fact mum rarely spoke of Aunt Lily. Perhaps Mum knew that working in a dress shop would be the right thing for me. We agreed on a time, and he wanted me waiting inside the house, where he would come fully dressed up as well. We would simply both enjoy the moment as pretty women. The next two days dragged on and on…