Sissy Milking Stories

28,345 results
Orientation
Length
Source
Infinite Scroll

Yeliza Awakens Pt. 02

by Yelizaveta on May 11, 2020
Transgender & Crossdressers

Part 2 of 2, hope you enjoy. Feel free to leave comments or thoughts. Or not, all good. Part four: The reveal Seeing him fully dressed, submissive, and made to look like a girl, her power was readily apparent. She reveled in it. He was patiently sitting on the bed, waiting for her direction. This power was becoming addictive. She enjoyed it more every ti...

Outed and Married Ch. 04

by keptsissy on Apr 23, 2018
Transsexuals & Crossdressers

I feel the cool air all over me. I'm in his warehouse. It's a huge facility and I'm naked and restrained in the middle of the football field sized room, surrounded by floor to ceiling full shelves of his adult sex toy products. Two other men that stand and watch stare impassionately. One of the men says something to the other man, points to rear end. The bot...

The Making of a Mistress Pt. 05

by EiryCGar on Sep 14, 2020
BDSM

Author's note: Marie has married and taken possession of Charles, now known by his initials as Cunt. She has become an official Hotwife; Cunt is now a true cuckold. This chapter deals with their honeymoon on Felicity's island, and the momentous decision that is taken when she and Cunt return home. As always in my fictional stories, all sexual acts take plac...

Behavior Modification Institute Ch. 04

by NancyPan on Sep 12, 2017
Fetish

I received some very negative and very aggressive comments about previous chapter postings. If you are not aroused by FemDom, Humiliation, and Forced Fem please do not bother to read this. These stories are for the benefit of those who enjoy this form of erotica. ***** I lost all concept of time as I fell into a rhythm of incredible stimulation to my penis...

Mama Mia Pt. 02

by grizzley123 on Jul 27, 2020
Fetish

This story contains many themes including cuckolding, gay sex, bsdm, incest and submission. If these are not your things, please skip. This is the second installment and it obviously helps to read the first part. The starting point here: I have just finished sucking off my temporary neighbor's cock. I have been set-up by my wife and her lover to be a submis...

The Set Up Pt. 02

by undermythumb10 on Sep 15, 2017
Fetish

This is the continued story of my life as a sissy and is a continuation from part 1 The Set Up. ***** As I mentioned I am sat tied to a chair with my stepdaughters panties placed so the crutch is over my nose, it's a long story which started when I met and married my wife now Mistress some six months ago. I am now a total submissive sissy cum slut for my...

Sissy for Mommy's Nipple Cream Ch. 04

by ppeaks42 on Feb 11, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Jaime clasped a hand over her mouth in horror, but it was too late and she knew it. Chills ran down her spine as Julia sauntered over with a wicked smile, then opened the door to reveal her sissy daughter sitting there wearing nothing but her lacy panties and her steel clitty cage...

Glory Days Again

by lil_raider on Sep 16, 2017
Transsexuals & Crossdressers

I just couldn't help myself. It had been years since I had a girlfriend and the last time I had gone out in full drag to a gay bar confirmed what I'd been feeling for some time -- a wig and lots of makeup could take 10 years off your age, but not 20. The bar scene was over for me and it had been a while since I'd had any real-life action. I got by with cam...

First Time Bi

by First_time_bi on Sep 16, 2017
Transsexuals & Crossdressers

I never thought that I'd be in this position. I am a 40 year old married man, 5'9" 185 lbs and try to work out regularly to keep in shape. The problem is that I travel constantly for work. It takes a tremendous amount of willpower to avoid the junk food and commit to a workout schedule when I am on the road. For the past 3 years, I have been the leading sale...

Khan Market Sissy

by smalltownsissy on Dec 24, 2019
Transgender & Crossdressers

An English degree was all that Lijo had when he took a train from Kochi to New Delhi. He was promised a teaching assistant's job at a University in Delhi. Though he knew that he could barely survive on the salary of a mere 16,000 rupees, Lijo still went ahead as he somehow wanted to leave behind his conservative hometown in Kerala and experience a metro life...