Mature Man Loves Tranny Cum Literotica Stories

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Mistress Chantel, Tranny Dominatrix Ch. 02

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Two: A Day in the Life of Tranny Dominatrix Chantel Waking up into another morning where this transvestite dominatrix gets to dress up and enjoy her life of toying with sub men and sissies/crossdressers. Working hard to get my femme look down over the last couple of years prior to operating this Dominatrix business, I enter my very lady-like powder...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....

Recruiting of a Sissy Maid Ch. 04

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel, Fitting Into Her New Lifestyle. Master Holt says, as the two of them walk out from the elevator on the 2nd floor, "This will be the floor that you will begin your life in servitude to us Chantel. Lets go find your head maid Penny and then get you to your room." Chantel grows more and more resigned to this new life as she see's a very...

Recruiting of a Sissy Maid Ch. 13

by Sissy_Chantel on Nov 28, 2017
Transsexuals & Crossdressers

Chapter Thirteen: A Business Trip to an Adult Movie Convention, Carl and Chantel Consummate a True Loving Relationship. Carl says, "Chantel make sure you pack well but not slutty ok. I will have you travel with me as my girl friend and secretary. Dress nice but casual for our flight but of course still be an eye catcher ok?" Chantel replies, "Ok hun, I fig...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

Mistress Chantel, Tranny Dominatrix Ch. 03

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Three: My Saturday Meeting with Kerri. Well another busy but fun week for myself as Mistress Chantel begins to wrap up. It's a bright, sunny Saturday morning about 7:30am. My typical femme routine is to shower, dry off, moisturize with fragrant, moisturizing cream then to shave my face. Luckily for me in recent months I have begun to use a beard ret...

Wife catches husband doing what!?

by Storymaster252580 on Jul 14, 2020
Fetish

Jeff and Lauren have been married for 3 years now. They met in college and dated for 2 years before eventually getting engaged and married. They are a fit and active couple always going to the gym. Jeff is 6-1 200 lbs and has a six pack and is packing a nice 8 inch cock. Lauren is 5-5 130 lbs with nice perky C cup tits and a firm round ass that gets all the...

The Virgin Tranny & the Bride Ch. 02

by yano on Sep 25, 2017
Transsexuals & Crossdressers

This is part two of a confession related to me by my transvestite friend Roberta, and like the first part, is so sexy without any further elaboration by me. Having seen some of the photographs, I can only say that she strays very little from the truth. Meantime I am trying to convince her to let me publish a few on the Internet. Watch this space. Exactly tw...

A Tranny Virgin No More

by Creamyirish on Sep 12, 2017
Transsexuals & Crossdressers

Fantasy became reality for my gal, Tranny G. She has finally started to come into her feminine persona. She has more confidence, is buying more outfits, and when she leaves HIM at work, she comes home and dresses. She starts with wearing short skirts and cami's, then sexy lingerie at night. She began playing with make-up and based on tips I gave her by e-mai...

Mistress Chantel, Tranny Dominatrix Ch. 05

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Five: Monday Morning You look so Fine. About 7:00am and I awake from the sofa bed of Gillian's place. I feel better after sleeping off the fun Sunday night activities with Kerri and friends. I need to wash up and get home to dress for my Monday schedule at my dominatrix studio. I shower and feel refreshed. As I dry off, there is a door knock and Ker...