Transgender & Crossdressers Stories

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Who Wears Short Shorts Again?

by grgy56 on Sep 16, 2017
Transsexuals & Crossdressers

Who Wears Short Shorts Again? "Dong! Dong!" The doorbell rang. "Who could that be at this hour?" I said to myself. 10 in the morning and I am still dressed only in my nightie. I draped a dressing gown over my diaphanous, Victoria Secret, shortie Chantilly Lace Babydoll and panties. By the time I answered the door, no one was there. Even though I was covere...

Sissy Boy Chuck Becomes Just Sissy

by Krazy35 on Sep 14, 2017
Transsexuals & Crossdressers

A long time ago, I realized that I had a thing for women's clothing. I used to sneak into my sister, Jessica's room and get all dolled up in her clothes. She was a year older than me, but we were practically the same size. I got an incredible hard-on looking at myself in her full length mirror. I quickly undressed, put everything back the way I found it, the...

Fifi La Femme: A Pansy at Last

by pris69696 on Sep 16, 2017
Transsexuals & Crossdressers

I have written this story "Fifi La Femme-A Pansy at Last" mainly from personal experience as a mature homosexual transvestite who was a gay virgin until my early 40s. I hope that it will appeal both to extreme effeminates and the ultra-masculine men they ache to serve. Now divorced I've been living with my boyfriend Ron for three years as his gay wife and ye...

That Red Dress Started It...! Ch. 07

by BethanyJ on Sep 12, 2017
Transsexuals & Crossdressers

Helen began to lead Miriam away, then turned back to me and looked towards Neil, stood beside me. Then she whispered "You've got ten minutes" . Ten minutes? For what? Hell!!! ********************************* I was standing there. With Neil. Helen had set me up again but this time she was serious. I turned to Neil, he was staring at my cleavage. I could...

Jill's Secret Ch. 02

by meatgrinder500070 on Sep 16, 2017
Transsexuals & Crossdressers

A few weeks had gone by since our first night together and the revelation that my goddess had a little something extra. Well, a BIG something extra. We awoke that next morning still sticky with her cum and of course both us sporting some serious morning wood. With barely a good morning kiss, we quickly got into a sixty-nine with me on top and sucked each oth...

The Change Pt. 05

by Miah_H on Sep 25, 2017
Transsexuals & Crossdressers

It was now the middle of the week off Jerry and Lita were taking. Aside from the sex-charged activities that had been going on throughout the week, Jerry was looking forward to Wednesday night for a different reason: the culmination of the World Series. Cubs vs Indians. Who would have thought? Jerry was an Indians fan, and seeing the team get this far has be...

Darren's Girl?

by mutepenguin on Sep 13, 2017
Transsexuals & Crossdressers

I'm Darren. I live in downtown Memphis. I head the IT Department in one of the corporate buildings on Second St. I don't consider myself to be the most attractive guy in the world but I don't have any trouble with the ladies. You know, I work out four times a week and run everyday but Sunday. I'm very lean but well defined. My hair is dark brown and cut shor...

CD Mistress Weak for Candy

by MistressCheyenne on Sep 16, 2017
Transsexuals & Crossdressers

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager...

Fifties Housewife The Next Day

by Gerilynn69 on Sep 13, 2017
Transsexuals & Crossdressers

This is a story about Gerry's life. You can read more about Gerry in the story Fifties Housewife. I have been working in a small accounting office as a bookkeeper. I work with three women in the office. Sarah is the CPA who owns the firm. She always seems to know whenever anything is going on. Jane works as our receptionist. She knows all the latest gossip...

Personal Assistance

by sexy_jessie on Sep 16, 2017
Transsexuals & Crossdressers

Rolling over, feeling a little groggy, Helena Stewart quickly realised that there was something not quite right. The hard mattress was not the soft sumptuous bed of her own apartment, the bare white walls not the passionate pink of her decor. Helena realised she wasn't in her own bed, wasn't even in her own apartment. She was wearing a small black leather br...