Chastity Cross Dressing Stories

77,281 results
Orientation
Length
Source
Infinite Scroll

Brandy Ch. 03

by JenniferGreen on Sep 14, 2017
BDSM

The continuing story of a beautiful young woman with a white mother and black father who is stunning, with long, thick brown hair, blue eyes, and mocha colored skin, tall and slender. * At that point I was working on my graduate degree in teaching, and living in my small apartment in the LA area. I still saw Brian and Tony and we all had a fun, mutually s...

Andrea's Guinea Pig Ch. 02

by spanishfly50 on Sep 14, 2017
BDSM

I went home after my evening on the cross with my balls feeling sore and my mind in turmoil. I sat in the lounge and tried to come to terms with what had happened and the way I had been treated, my balls were aching following the abuse they had received from Andrea's riding crop, I tried to find some way of easing my discomfort but it was impossible due the...

Jay Cross

by JayCross on Sep 14, 2017
Transsexuals & Crossdressers

It was getting dark outside. I sat on my bed reading my favorite magazine, waiting. The sunset ment it was getting closer for my mother to go to work. I walked out of my room and looked down the stair case. I can see her getting her purse ready. I was already done with all of my homework and was ready for a little fun. "Jay, honey I'm leaving" "Ok mom, I'...

My Mother, The Stripper Pt. 04

by raiderdrm on Sep 25, 2017
Exhibitionist & Voyeur

When I finally woke up, it was Wednesday morning, around nine. Janie and I, hadn't returned home until after one in the morning, we had stopped by our neighborhood restaurant for coffee. Today, we needed to go shopping, to purchase our Thursday evening outfits. Neither of us, sure of what we were going to wear for our local lodge encore. I had an idea, but...

Amy Sue and Maxine Ch. 01-04

by reddbunnz on Sep 1, 2017
Group Sex

Chapter One "Maxine, you sure look like shit," my best friend Amy Sue says while staring at my naked body. "You look like something that's been ridden hard and put away wet." "Well, I've just fucked the entire football team," I reply. "So I guess that I have been ridden hard. And, I'm still very wet with all this cum in and on me. But, I'm sure not ready t...

The Rapture

by soppingwetpanties on May 22, 2018
BDSM

Warning: This story contains graphic scenes depicting humiliation, pain and watersports. It also depicts female submission. PLEASE do not read this story if you are offended by any of these topics. Thank you to Jennifer M. for the inspiration behind her namesake in this story. I hope you find your Domme. Thank you Robert for your helpful comments. This i...

The Writer's Secret Conclusion

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? * Chapter 13: Laura Blossoms A routine developed. During the weekdays, Kathleen would come over to watch Loren work. They wou...

Payback is a Bitch, You Slut Bitch

by SusanJillParker on Sep 13, 2017
Loving Wives

Loving wife gets an unexpected Valentine's Day surprise * Perhaps being the romantic that she was, Tina's favorite holiday, besides Christmas and her birthday, of course, was Valentine's Day. As the days grew closer, counting the days until Valentine's Day, she'd X off the time that passed on her Renoir calendar that hung on the refrigerator by a Cupid m...

The After Time Pt. 02

by mountian299 on Sep 16, 2017
Novels and Novellas

Chapter 6 Janice I seen some pheasant in the apple trees I am going to get some for supper. You taking Mona you know she won't let you go alone. Ok but I am taking Cindy I grabbed the food bag and the cross bow went out gathered the girls to head back to the house and told Cindy we were going after supper. Mona was following quietly behind we got to the ap...

Alka Makes Three

by Verynicehands on Sep 15, 2017
Loving Wives

Thank you to all who have provided feedback on my first three stories. Since then, I've tried to apply what I've learned and been inspired by Travel Girl who writes from the perspective of a woman who meets others while travelling on business. I recommend her stories highly! This story is from the perspective of a couple who meets a sensuous woman on busine...