Maid Chastity Stories

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Sissy Chantel, New Reality Ch. 06

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Six: On My Way to My New Life at The Agency. Well the day has come for my transition in my life to becoming another sissy maid and sissy slut (aka: comfort girl) to 'The Agency'. Over the last two hard and humiliating weeks Master Camron and Sir Gage now as paid agents to my joining the team at 'The Agency' have helped me sell, give away or toss o...

Caitlin and Mistress Vicky Ch. 03

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

I was sitting nervously in front of the mirror in the newly decorated guest room. Chad was set to arrive in half an hour. My wife was getting ready in what was for now our bedroom. She had told me to dress up for the occasion, though I was still to wear my maid's outfit. I opened my jewelry box and tried to decide how to accessorize. I selected a lace choke...

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...

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

Lace and Love Ch. 02

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Dan had a quick shower, brushed his teeth, and after giving himself an enema he started the process of becoming Alice. He stepped into their bedroom and opened the small walk in closet revealing men's clothing for him and Jake, Jake's old uniform from the marines, some various camo and tactical clothing Jake wears for his firearms training business then came...

The Traning of Cinderella

by MistressVivian on Sep 17, 2017
Celebrities & Fan Fiction

Chapter 1: Cinderella's Awakening Cinderella awoke to the most magnificent day ever. Her prince charming rescued her from the atrocious and ignominious drudgery that her stepmother and stepsisters imposed on her since the death of her father. After a magnificent ball and a wonderfully passionate night of lovemaking, Cinderella awoke to a magnificent spring...

Becoming a Sissy Maid & Slut Vol. 06

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Twelve: Chantel's day off. Ohhh, and ahhh as I awake and stretch in my bed. Mmm a blissful sleep where I see the clock and that it's actually 10:00am. At first I freak out a little bit as it normally would be very late for me. But I soon realize Master has allowed me a blissful and free Sunday off. I then get out of bed, my butthole is sore from the...

Scene from a Dinner Party

by MaidinChelsea on Sep 15, 2017
BDSM

I lean sensually over the table as I serve their starters and I see Alison's eyes flick admiringly toward my chest, "Goodness, are those real?" she says. "Well, yes and no," my Mistress giggles, "They're certainly attached. Polly, show my guests your new 34Cs." I feel a heat wash over my cheeks but know better than to hesitate. I reach around and pull the...

A Sissy Fantasy

by Sissy_Jeanette on Mar 30, 2020
Transgender & Crossdressers

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing...

Transforming Brent Pt. 02

by sissymissyct on Jul 10, 2019
Loving Wives

Kept in Loving Wives to annoy the tiny dicked anonymous reviewers that love to trash everything they read (after they wank to it). *** I woke up Sunday morning with a painful erection in my chastity and the pumps still attached to my breasts. I reached down trying to find a way to ease the pain in my penis. Nothing seemed to help. Maybe Wendy will be up so...