Sissy Milking Stories

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Orientation
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Infinite Scroll

An Expensive Addiction Ch. 03

by NeverGuessWhatsNext on Sep 16, 2017
Transsexuals & Crossdressers

The Friday after my second encounter with English was just as eventful as I had thought it would be. My girlfriend got to town, and since we hadn't seen each other in weeks, she was hornier than hell. I picked her up from her parents house around 5 and we went straight back to my place to have sex before going to the party. A couple of months after we starte...

Mz Zen's Fabulous Birthday Pt. 01

by lushusboobs on Sep 17, 2017
BDSM

Chapter 1 Ms Zen was turning 40 in just 5 days. The prospect of 40 was depressing. The closer it got to her birthday, the more irritable she was becoming. Although she'd always had a healthy attitude towards age, she had to admit that the reality of turning 40 was far different than she expected. She was actually dreading her birthday and she had avoided ma...

New Year Cuckold Ch. 02

by 0131aj on Sep 16, 2017
Transsexuals & Crossdressers

After the party at New Year Julian realised his marriage was over. He had have been working overseas for about five years and the strain eventually had proved to be too much for his wife. Ever since their wedding day he was aware that she was having a series of affairs with other men. She was a beautiful brunette, with superb legs and shapely figure, confide...

Kim Meets Master Jim

by Master Jim on Sep 16, 2017
Transsexuals & Crossdressers

Their first encounter had been well planned. Since Kim and her master had already corresponded via email for some time and even chatted on the phone, they knew they were ready for the real thing at last. Master Jim had booked the hotel room, stocked it with liquor, then went to the spacious lobby. He sat down and nonchalantly set the room key on the adjoini...

His Fantasy Brought To Life

by ksha on Sep 16, 2017
Anal

To my surprise, my first story was received quite well! So thank you to everyone who read and liked it, hopefully I can continue to make enjoyable stories. As per a request in the comments on the last story, I am writing this. It's a stand alone from the other story, but follows similar lines. It's also going to have a long build up, but I'm hoping the end...

March Madness Ch. 09a

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Her Male Wife

by Zippeduptight on Nov 6, 2018
Transgender & Crossdressers

Sometimes I wonder how I got into this mess. The answer is obvious but it usually comes during the day when I pee. Carla's orders are to sit when I pee. I lift up my skirt, and tuck the exposed chastity device down, and relieve myself. Just like now. The shiny pink pvc sissy maid outfit she bought for me is locked on at the neck. I stand up and flush walking...

April’s Child

by 4glory6 on Sep 16, 2017
Interracial Love

"Annie, you take them children up third floor. They like to wear Miz. Irene out on the trip. And you, Toby, stop moonin' over Annie and get the ice chest goods into the house and in the ice box. You got ice in the ice box didn't you?" "Yes ma'am," Toby answered as he trotted out the kitchen door and down to the Buick car in the drive below. "And you, Miz....

For His Mistress' Pleasure: Final

by femmepen on Sep 12, 2017
BDSM

I felt someone jabbing me awake to find Sonja on top of me directing my semi-erect cock into her pussy. I laid on my back looking at her firm body as it lowered over my growing member. Then a waft of sex smell permeated my nose as Daniel placed his used cock against my lips. Still waking up I was forced to take the large tool into my mouth to suck as he rest...

An Unexpected Twist

by Buildaworld on Sep 16, 2017
Transsexuals & Crossdressers

A week has passed since that event and things seem to have become steady again. Gabrielle and myself are in contact every day, Melanie has backed off and everything feels perfect. We even met yesterday for a quiet little meal, but after a meal and a few drinks, I was stretching Gabrielle's tight little pussy and she wasn't being quiet about her pleasure. B...