Chastity Cross Dressing Stories

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Infinite Scroll

From Jeannie to Vanessa Ch. 05

by v22omk on Dec 9, 2019
BDSM

Author's note. These are not stand alone stories. If you haven't read chapters 1-4, please go back and read them first, or this chapter will make no sense. Chapter 5: Private session As we approached the shopping district where Visions in Lace was located, it suddenly dawned on me that it was getting fairly late in the afternoon. Would the store even be op...

Caught & Blackmailed Ch. 01

by Bronnyard on Jul 14, 2020
Loving Wives

I looked up at the red, sweaty face above me. It had its mouth open, gulping in air and gasping. "I'm Coming!... Fuck it I'm Coming!" It grunted and I felt his cock pulsing, as he added another load of spunk, to my cunt. "Christ! I thought. How did I get myself into this position." Another cock pushed into me. I closed my eyes and my mind replayed, the...

Fun at the Mall

by SK1328 on Apr 1, 2020
Erotic Couplings

Sevyn and Kati had both just turned eighteen not too long ago, and over the summer after their birthdays they had decided to take a mini vacation out of state so that they could see the campus of the college that they were going to go to and see a couple of other things along the way too. One of the things they wanted to do was visit one of the malls, as th...

Compromising Positions Ch. 10

by Timeris on Jun 9, 2020
Exhibitionist & Voyeur

As they sat around eating, they began talking. Jenne told them of her recent transformation, and how amazing her week had been. She glanced at Angela with affection. "I'm so lucky that I found Angela, and I found you guys. It's really been incredible." Cheryl got a mischievous look on her face. "So what was up with you the other day? You could hardly talk y...

Bartered Orgasms Pt. 01

by Follyseer on Apr 17, 2019
Loving Wives

Bartered Orgasms with Agonies of Faith (Part One. Possibly stand alone.) (An "adult" read of more than 10,000 words. This is an effort to touch on the implications of whoring in periods of social tumult and political upheaval. There are no pretensions of expertise in the history and culture of South Africa. The author is acquainted, however, with knowledg...

Courtesan Ch. 41

by Goodhusband on Sep 19, 2017
Loving Wives

This is the forty-first episode in a series entitled "Courtesan". If you have not read the previous forty episodes of this series, I encourage you do so before beginning this chapter. "Courtesan" is romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alternative...

Young Sissy Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of roll...

Pretty Chris-tine Ch. 02

by jealouscuck on Sep 26, 2017
Fetish

My wife, Sharon, and I were lifelong friends. We eventually began dating and then got married. The idea that eventually shaped part of our sex life was her grandmother remarking that I was too "pretty" to be a boy. She thought that my complexion and clean looking face was attractive. One time as a lark, Sharon asked me to let her put makeup on me. I initiall...

Male Model

by penny_singleton on Sep 25, 2017
Exhibitionist & Voyeur

I work at a local art studio as part of a Continuing Education program. I basically order materials and schedule the artist sessions. Scheduling includes the hiring of models. This brings me to my story. I was given the assignment of hiring a male model for undraped sessions. Now I have hired a number of female models in the past, and I usually use the l...

The Road to EGOT Pt. 07

by ManUnited1086 on Sep 26, 2017
Celebrities & Fan Fiction

I woke up the next day feeling lighter than I ever have. I was lying in bed next to this beautiful woman I was totally in love with. The best part of all is that she loved me too. I held her sleeping body in my arms wondering how I ever got so lucky. I finally had to get out of bed and get ready for work. She was still sleeping when I was on my way out and I...