Sissy Maids Stories

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Orientation
Length
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Infinite Scroll

Dickgirl Tyranny

by Lusc on Mar 28, 2018
Transsexual

In this medieval/victorian fantasy world, the physical differences between men and women(also known as dickgirls) are enormous. In comparison to their male counterparts, women are taller, stronger, and better endowed. On top of all this, a dickgirl's cum has a strange drug-like effect on males. This effect's severity is mild when applied to the skin, stronge...

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Appointment by Card Only Ch. 05

by Sputnik57 on Sep 17, 2017
BDSM

Madam Clara did not just have Lucy attend her 'classroom' that day; the soft ginger girl was made to stand in the corner facing the walls while other 'pupils' were brought to attend. Such was the wealthy woman's lust for her kink as the domineering schoolmistress, she had also paid for three males to attend her 'class' that day; each deeply submissive male h...

Being a Sissy for Viv Ch. 03

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

I awoke slowly, enjoying the warmth and comfort of the bed and thick quilt. My mind was slowly trying to separate half remembered dreams from reality. Pink panties. A lacy bra. Viv's breasts. Excitement. Embarrassment. Suddenly my eyes were open as the catalogue of disjointed dream images slotted into the reality of the previous evening. Even as the memori...

The Valentine Surprise

by rogkw99 on Sep 16, 2017
Transsexuals & Crossdressers

(This is not fiction or fantasy. It is a true accounting of what happened to me last Valentines Day. Even if you think it is fiction, I think you will enjoy it. I would enjoy it if it were about someone else and not me!) I can't help but think of Valentine's Day last year, a day that forever changed my life. In the weeks leading up to that day my wife Ama...

Sissy Gets Punished

by MsMorrigan on Sep 16, 2017
BDSM

Once upon a time there was an overly eager sissy girl. This sissy girl loved her mistress. She loved her so much she tried to anticipate her every whim before she needed to even speak the words. One day the sissy girl was vacuuming, dusting and general cleaning. She was openly lamenting on how her overly large pathetic sissy clit was getting in her way. How...

Replaced Ch. 02

by chas19839 on May 23, 2018
Fetish

I wasn't anywhere close to having the house where I wanted it when I heard the crunch of tires on gravel in the driveway. Vince and my family had been gone for over three hours. They must have gone for a walk or maybe shopping after lunch. It was such a strange sight seeing the four of them walking from the car to the house. It felt surreal. I opened the do...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

Unexpected Encounter Pt. 01

by cddream on Mar 6, 2018
Fetish

It was a week night and I received a text from an ex girlfriend I haven't talked to in 2 years. I stared at my phone in surprise when I see her name pop up. My heart kinda skipped a beat and I opened the text anxiously. It was from Molly, she was the first girl I exposed myself to. She knew all my secrets and kinks from our past together. The text simply re...

Ultimate Sissy Weekend Ch. 03

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Before today, Susie had only ever spanked herself. Nothing could have prepared her for the 220 spanks she'd received earlier, her first serious sissy spanking. Still her butt burns, even in its new pink poofy diaper. And now it's joined by fresh welts and lines on her inner thighs from the cruel canings of the redhead's ruler, as she happily decorates the tw...

Developing Emma Ch. 03

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

As Kurt caressed Emma's sweetly pronounced bottom, she realised she had never felt so feminine before, despite her newly freed cock standing stiff in nervous anticipation. She looked at the powerful male and the leering male audience; the few females there would now witness her being used as a woman. Kurt's large stiff cock rubbed against her belly as he mov...