Sissy Housewife Stories

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Miss Jennifer's Sissy Housewife

by tiffanyfoxe on Sep 19, 2017
Transsexuals & Crossdressers

My job was much less demanding than my wife's, so she had always "suggested" that I do all the housecleaning, shopping and cooking all week, and of course I never minded because I secretly loved being subservient to her. She loved to tease me when we'd be out somewhere together and she'd see a good looking guy by telling me how attractive she thought he was...

Sissy Housewife Learns to Eat Cum

by tiffanyfoxe on Sep 12, 2017
Transsexuals & Crossdressers

Only a few days after Miss Jennifer agreed to let me be her housewife, she informed me that now that I was "pretending to be a girl" and was required to always be dressed completely as a girl, she expected me to service her the way one girl would service another, with my mouth and tongue. At least three times every day (always in the morning before she left...

Sara's Amazing Night

by Sexy_SaraCD on Sep 16, 2017
Transsexuals & Crossdressers

I felt his entire weight, his entire body push me against the wall and the more I struggled the harder he pushed into me. My hands are firmly planted on the wall and my eyes are closed. At this moment, I feel panic. Panic of what may come soon. His leg, strong and thick, push my legs apart but my tight skirt stops them. He doesn't let that prevent him from...

Miss Jennifer Fucks Little Tiffie

by tiffanyfoxe on Sep 12, 2017
Transsexuals & Crossdressers

The Saturday after Miss Jennifer had her boyfriend fuck my pussy/bottom, she called to me while I was doing her laundry and told me to come to her room. As I entered, she told me to come and stand in front of her, where she was lying on her bed. I was, of course, dressed like a proper little housewife, with my pink lace bra stuffed with my big 54DD falsies...

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...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

A Sissy Saves the Neighbourhood

by JerkGently on Apr 22, 2025

You hung another dress on the line… basking in the bright sunshine for a moment. The fresh, Spring breeze cast your long, brown hair around your face, sending goosebumps rising across your bared stomach and thighs. You still felt a little nervous and exposed… standing out in your own backyard, dressed like this. Short-shorts and boob-tube all that stood betw...

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Sissy Joanne Parr Fantasy Fucking Ch. 01

by Sissy Adele Howells on Aug 18, 2017
Fetish

Joanne Parr was 26 years of age. She had an obsession with the Barbie doll . She wanted to look like Barbie, as well as dress like her. One day in the office, I was so jealous of her. How dare she wear pretty dresses, when they would look much better on me. I want to be the new Joanne Parr, but I needed help to allow my kinky fantasy to take place. Georgina...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

My Stud's Special Secret

by MidnightWriter on Sep 19, 2017
Loving Wives

My name is Nikki and I think I've got a different take on this cuckold thing so many of you guys seem so nuts about these days. I'm 28, a former stripper who found the hung stud she'd always dreamed of about a year ago in the form of my boyfriend Drake. He was older than me, though I honestly didn't know how much at first, just that he was in his late 30s o...