Sissy Milking Stories

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AliExpress and Sissy Downfall Pt. 04

by His_fag_wife on Dec 30, 2017
Transsexuals & Crossdressers

As Tim added inch after inch, slowly taking his time, stretching his new slut, driving deep into Emma's tight twitching arse, she moaned with the pain like a wounded animal. He loved the supremely tight fit as he slid forward into her, bit by bit. His sweaty ball sack finally rested on Charlies face, each of his big balls settling into Charlies eyes sockets...

Jennifer Monroe & the Ladies Ch. 01

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Jennifer Monroe & the Ladies -- Chapter one Jennifer held Debbie's hand as she led him down the stairs and into the finished basement. It was a large single room with a sofa, a few comfy chairs and a queen-sized bed at the far end. Seated on the sofa and chairs were five ladies, all of them dressed in corduroy outfits. Jennifer ignored them as she whisk...

The Visitor Ch. 02

by RobertoTropical on Sep 18, 2017
BDSM

Later that afternoon I found myself securely spread-eagled face-down on our bed with my mid-section raised by three pillows. As the two of them were tying me down, M. asked Emma if she wouldn't mind removing the giant steel butt plug. "Won't he feel empty and denied if we take that pleasure away from him," Emma asked. "You need for him to get something out...

A Cuckold's Ordeal

by mollycactus on Sep 19, 2017
Fetish

He didn't want to look. But he had to look. It turned his stomach to look. But Jeff had to look. Why 'had'? For several reasons. His Domme Miss Sophia ordered him to look. His wife Rebecca ordered him to look. So he had to obey. But also, he had to look in the same sick, twisted way that people look at car wrecks and other disasters, both hoping to see s...

Tricked Into Love

by bluegiraffe on Sep 14, 2017
Erotic Couplings

I was looking through the internet personals to pass the time, although deep inside, I was actually desperate for a date. My name is Mike, and I was a 21 year old guy in college studying sociology. I wasn't bad looking or anything but just a little shy. Usually, the personals were just full of kids putting fake postings or unattractive women who couldn't ge...

My First Feminization Pt. 03

by npbear on May 29, 2018
BDSM

Startled by a hand sliding under my arm, I jump. The shock brings me out of my sex-induced haze and I realise that they are helping me up, off the cushions, onto my feet. Slowly I tune in to the fact that they're actually talking to me as they pull. "You poor dear," a gentle voice says "they just left you here, didn't they? No one picks up after themselves...

Brett's Transformation to Brenda Ch. 02

by tinycuck84 on Sep 16, 2017
Transsexuals & Crossdressers

I opened my eyes slowly and yawn after a long sleep. I tried to move my feet to get up, but they are still tied to the bed posts. I tried moving my arms and I noticed they are tied to the headboard posts. My eyes widen as I feel my naked body underneath the bed sheets remembering the night before. I tried to wiggle loose, but there is no use as I am complete...

And Then You Can Do It To Me

by InYo on Sep 13, 2017
Fetish

Author's Note: I was flattered by the immense response I have received regarding the ending of this story. Sorry it has taken so long to get this posted, but I wanted to wait until the responses stopped coming in. And after that my whole system crashed and took forever to get fixed. But here I am back, and by an overwhelming 4to1 demand, the main character f...

A Helping Hand

by LockedSissySubmissive on Sep 13, 2017
Fetish

"Ok, I have plans for today," my wife announced out of nowhere, "today you're going to dress up for me and I'm going to show you the new toys I've bought." "Erm...ok." I answered carefully. We had been having a leisurely Saturday morning breakfast and, as far as I knew, had made no plans for the day. "What toys have you bought honey?" I asked curiously....

Next Time Ch. 03

by First_time_bi on Sep 26, 2017
Transsexuals & Crossdressers

When we arrived back at the house, Heather took me by the hand and we went upstairs to the master bathroom to freshen up. As soon as the door was closed behind us, she took me in her arms and began kissing me. "Maria, that was so sexy, watching you suck Michael's cock. Did you like it?" I smiled and shyly nodded. "He wants you Maria. He wants to keep you f...