Shemale Chastity Stories

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Mistress M Pt. 03

by humblersub on Mar 2, 2020
BDSM

He was once again in her bed between her legs. He had lost track of her orgasms at about twelve. She was way past that now. He had also lost track of time. He never tired of making her cum. And she never tired of him being between her legs. She had given him increasing license to do what he wanted with his tongue and fingers when he was between her legs. He...

Mamma Mia - En Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"Ah chico, I think you already know the answer. It's making you into exactly the lover I want," Mia said as she brought a hand over to rub her cuddling stepson's chest. "It's making you into a woman like me." All the changes he'd experienced over the past weeks suddenly clicked in Tommy's head. The swelling and tenderness in his chest. The slight widening o...

Girlfriend Trouble

by lovelymess212 on May 29, 2019
Fantasy

You've been dating Sam for a long time, even thinking of popping the question sometime soon. She's perfect in every way, and its near your second anniversary. You have your own apartment together, living with each other to count on. Maybe life is far from perfect, but you have each other. Of course, sometimes life throws you a curve ball. You wake up one mor...

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The Journey Ch. 02

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

(You may want to read The Journey before reading this so you will know the background of Tom/Tonya and Jason. These stories are a combination of real life and fiction. Thanks for sharing your comments.) Tonya was content as she stretched across Jason's lap. She had given Jason a long slow blow job and now Jason was rubbing his sissy slut's smooth ass a...

Made to Obey Ch. 09

by madetoobey on Jul 30, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Humiliation was now a daily event. Esther, who had investigated my internet usage on my laptop to see if I'd visited shemale...

How it began

by Thehypest1 on Apr 15, 2019
Fetish

You wake up after a long night of drinks with Casey. You hear the jarring sound of the alarm echo in your head. You think to yourself 'How much did I drink last night.' Your head is pounding and you lay in bed for a bit before heading to the kitchen to get water. You run into Allyson there. She made breakfast, she really is too kind. "Good morning, slee...

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The White Slave

by mspbottom4black on Oct 6, 2020
Interracial Love

Editor's Note: this submission contains raceplay and femdom content. * Not long ago it was a straight and stuffy white male. it was arrogant and self-satisfied with its white male social and economic leverage and advantages. In the rat-race of white society it suppressed its submissive white side. But from time to time it would slip into daydreams of hav...

Mommy Adriana, I Will Obey You

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

Dear Readers, since I am open to suggestions from now on I will start my stories with a recap of what has happened before. * Finally we were on our way home. Interestingly neither Mommy Adriana nor Mistress Andrea had cuffed or gagged me. So I just sat in the back of our car. During the short drive I had some time to think about what had happened in the p...

Mamma Mia - Forced Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"We need a little more feminine energy around here." The words hung in the air as Tommy's devoted licking of Mia's ass slowed to a stop. "You mean another woman?" Mia hooked her legs behind Tommy's head and pulled his face back into her ass. "No, I mean you, you dumb sissy bitch." Once Tommy finished with pleasuring Mia, she led him into her closet. She...

Willing Submission to a Dickgirl Ch. 01

by ArthurSummer2 on Dec 7, 2017
Fetish

Note to the reader: This story takes place in a futuristic world where body modifications and high technology are common place. Because of this, there are a subset of women who choose to have male genitalia attached to their bodies. These cocks and balls can be, and often are, much larger than natural male genitalia. So if you are not interested in futanari/...