Sissy Milk 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...

A Day at the Fetish Flea

by Tinababy on Jun 11, 2019
Transgender & Crossdressers

I first met Jack at the bar. It was a little uncomfortable for me talking to people there, because not only was it was a drag bar, I was drinking alone and I dreading that I might run into someone who might recognize me. I had been to the Fetish Flea that afternoon, gawking at the outlandish gear. Many booths lined the hall, and hundreds of freaky people st...

A Sissy Saga Ch. 12

by Snurge on Sep 15, 2017
Novels and Novellas

Poppy returned to the dormitory much earlier than had been planned. Most of the students at the Grange were in special detention and occupied in doing things in preparation for Open Day, but he was no longer a proper pupil and for a while that afternoon he was a free agent. He was feeling active and restless, but he arrived to find the room occupied by the...

Kinky Dentist Sian And Sissy Rachel

by Sissy Adele Howells on Dec 12, 2018
Fetish

Most people hate going to the dentist, but I get a sexual pleasure every time my appointment comes around. That is because my dentist is the sexiest women, that I have ever set eyes on. Sian Harris is in her late thirties. She is of medium height with short, brown, mousy hair. Sian is very pretty, with a smile to melt any perverts heart. Sian's husband worke...

Carol's Gifts

by Belongs2Beth on Sep 16, 2017
BDSM

Authors note: This is the third story featuring characters introduced in "Carol's Christmas." In this installment Carol give's Jack his Christmas gift one night late with the help of Irena, "Marcia" and several well hung younger men. The sex action in this story is unrestrained, and since the tags are at the bottom of the page, I will issue the following mil...

A Little Bit Feminine

by ThatGuyMan on May 12, 2020
Transgender & Crossdressers

"Are you sure I can't help?" The reply was cut short by the sound of Jason retching once again. The sound came from their bathroom at the end of the bed, where it had for the last five minutes. Tammy leaned up in bed, concern on her face, as she made to kick the sheets off and go help her husband. Jason, ears like a hawk despite currently revisiting last n...

Claire's New Start

by Sissyhalo on Mar 21, 2018
Transsexuals & Crossdressers

There's the thick taste of cum in my mouth and my bum has that feeling of being fucked...filled...made love to and last night replays in my sleep along with everything that has found a home in my head. ...Stop lying, start loving that cock inside you. ...You've never been man enough but you can be sissy enough. ...Worship cock like a good sissy girl. ......

Kinky Adele Mummy Fucker Ch. 02

by Sissy Adele Howells on Sep 17, 2017
Fetish

I had no idea what a dominant, perverted women Adele Howells could be. She wanted me to take her eighteen year old daughter's virginity, but at a price. Everything would be on her terms. She now had complete control over her husband Tony. I was made to sit naked on her bed, as I watched her put her lipstick and clothes on. My cock was as solid as a rock, as...

The Molly Virus Ch. 05

by Sissyhalo on Mar 12, 2018
Transsexuals & Crossdressers

*Before... I kiss him leaning down and shoving his legs up with me as I fold him in half and fuck him over and over as we kiss then it happens. There's this inside resistance that stops as the brain and body reconciles getting fucked and relaxes and lets it happen. There's this sweet sigh of surrender that comes out as I bottom out inside of him and then h...

Auntie Jean Drummond Lloyd Ch. 3

by Sissy Adele Howells on Aug 31, 2017
Fetish

I had been stripped naked by Auntie Kimberley Holmes. Auntie Jean stared at me, then she turned to Adele Howells. Adele was 49 years of age with short, jet, black hair. She looked stunning in her tight, white trousers, over her long, black booties. Her green, patterned, satin blouse was stained with Simon Bennett's semen. Adele's thin, red lips looked so inv...