Heavy Makeup Sissy Stories

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My Stroll outside the Car

by triffle64 on Sep 12, 2017
Transsexuals & Crossdressers

It was a beautiful evening in the spring of 1982. My wife and I were taking a drive up the coast of California for an evening stroll. She was driving. We had been married for about 5 years. She was 27, and I was 30. My wife is feminine, but she grew up as a tom boy. I had no idea that she would take so well to my submissive desires to be her sissy husband. T...

If Women Ruled The World Ch. 03

by chronoxxx on Sep 15, 2017
Fetish

I studied the bottle of luminous green liquid carefully before introducing it to the bathwater. As the instructions directed, I then stirred it in until the formula had uniformly dispersed. Its sickly look mirrored the growing feeling in the pit of my stomach. I then attached a curious gauze just above my genitals covering part of my pubic hair and gingerly...

Sissy and Missy

by ChristopherDB on Feb 12, 2019
BDSM

Copyright 2019 Christopher D.B. * The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week. My feet were hurting, as the toe box on my pumps fit a little...

I Learned My Lesson Well Ch. 03

by Angelscuck on Sep 2, 2017
Exhibitionist & Voyeur

Well the weekend had arrived. My Fiancé, Angel, had given me a complete makeover at the salon. I looked ridiculous in my maid's costume with full makeup, heels, stockings, garter belt and leach with collar. She looked amazing with her slutty makeup, hair worn up and completely naked under her trench coat. We were on our way to her gangbang. Her black maste...

Chrissy Gets Caught

by femininechrissy on Sep 18, 2017
Transsexuals & Crossdressers

I don't even know where to start. I've been cross dressing ever since I was a young girl, I mean boy. I have always been jealous of women. They get to wear the prettiest clothes. They get to wear makeup and make themselves look beautiful, as if they weren't born beautiful already. I have loved wearing panties and bras and dresses and makeup for as long as I...

I Adore Crossdressers

by Ab9095 on Nov 26, 2018
Transgender & Crossdressers

I adore crossdressers. Adore!! Pretty little pantied asses up in the air. Shaved dicks and balls hanging down. Pretty little assholes. Fuck Yeah!!! I love seeing their hard dicks flopping when they are riding a cock. Fucking A, when they are hot they are HOT!!! They don't have to be perfect any more than any woman does. They are ALL good. But I do love it...

A Sissy's Joy in Being Fucked

by MissDeeLiscious on Sep 16, 2017
Transsexuals & Crossdressers

We were in the back room of our local drag club, "Miss Thing's", a very special place where only the seasoned and initiated drag queens and sissies are allowed after hours when the queens have finished performing. As one might imagine putting on an erotic performance going as far as the law will allow all painted up in all their glory makes them aroused in d...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

Sissy Chantel, New Reality Ch. 09

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Nine: It's Friday, I Have a Full Shift to Pull Today and Tonight. At 7:00am sharp we are all waken up. This is our daily wake up call and soon sissy Traci as our dorm room's head sissy maid has us all up and ready to go to our morning routine which will be a group enema, group shower, shave face and when need be the rest of our body hair then to do...

I Learned My Lesson Well Ch. 02

by Angelscuck on Sep 14, 2017
Transsexuals & Crossdressers

As I told you in part 1, Angel really taught me a lesson regarding cumming without her permission. I was so grateful that I hadn't lost her to a superior black stud, I was even afraid to masturbate to porn on the internet. We have two computers, hers and mine, next to each other in our office. She told me she had forwarded an email to me from one of her gi...