Sissy Milking Stories

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Sissy for Mommy's Nipple Cream Ch. 05

by ppeaks42 on Nov 2, 2020
Transgender & Crossdressers

The evening after Jaime's doomed attempt at seducing Julia found the young sissy crying into her pillow as she tried to reconcile herself to the whirlwind of changes she'd gone through. Less than two months ago "Jaime" had been nothing but a shared figment of imagination, a character he dressed as for his regular breastfeedings with his mother. When he'd tri...

For His Mistress' Pleasure Ch. 04

by femmepen on Sep 14, 2017
BDSM

As Mistress checked the goings-on in the kitchen I heard the first bell ring. Taking a deep breath, I closed my eyes and held my confidence in check. I knew I looked a little ridiculous in this outfit, but whatever pleased Mistress pleased me even more. A calm rested over me as I opened the door to our first guests. I recognized them from the fetish clubs...

Danny's Education

by Greymead on Sep 19, 2017
Transsexuals & Crossdressers

"Damn it, Jem! I'm a doctor, not a sissy!" Jemima chuckled, recognizing my weak attempt at humor as I tried to avoid the question. She was still holding the brief, lavender panties out to me. "C'mon, honey. Just do it this once for me, please?" Her big eyes begged more eloquently than her voice, and, though I didn't care to let her know in case it made me...

The Vacation from Hell Pt. 01

by JamesMiehoff on Nov 27, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

How I went from Domme to Slut Ch. 03

by Ms_Allison on Mar 7, 2018
BDSM

Another night of not knowing and torment was coming, this time I would have company, amber would be with me. This would be new. Ms. Linda had contacted me during the day via text. Her instructions were quite simple, amber and I were to bring a selection of slutty lingerie for her to choose from, our highest heels, and not bring any attention to ourselves as...

AliExpress and Sissy Downfall Pt. 05

by His_fag_wife on Feb 6, 2018
Transsexuals & Crossdressers

Charlie was deep in it now, being assessed by Miss Bell the beautician before she started work on removing all of Charlies hair below her soon to be plucked eye line. Candice the young pretty petite receptionist was also looking on to deepen Charlies humiliation. "Miss Bell, I'm really tight, but even my little pussy couldn't be satisfied by that little cli...

Strawberry Milk Pt. 04

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

Once I figured out how I wanted to experiment with this revelation on my nanos I decided on Dr. Corey as the start and Jill my porn store sissy. Dr. Corey was fucking me everytime I seen him and I started trying to concentrate as he breastfed from my huge titties. Not out loud but like mentally to my nanos. ~Harder, a harder bigger cock...more sperm, more...

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...

Sissy

by TxRad on Sep 14, 2017
Mature

I came in from work about noon on Friday. I had been gone for a little over two weeks. Pulling in the driveway, I noticed that my daughter's car was gone but her best friend's car was parked in front of the boat on the far side of the carport. You talk about a pair to draw to; those two were it. My daughter is tall, dark, and slender, Sissy is even taller, b...

Venus Trader

by skinnysailor on Oct 24, 2018
Transgender & Crossdressers

It's Oh Five Thirty aboard the seven hundred foot container ship 'Venus Trader' Twelve days out of New Orleans towards the Suez. It'll soon be time to get out of bed and fetch the Captain's breakfast. I'll lie in for a bit longer. I hear the door for the head open and close. I feel the bunk as Captain crawls in beside me. I pretend to be asleep. Our little m...