Rubber Sissy Stories

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Orientation
Length
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Infinite Scroll

Alex to Alexis Ch. 02

by TransPrincessMorgan on Sep 25, 2017
Transsexuals & Crossdressers

Again, thanks to Jack Murphy for being an amazing volunteer editor! Enjoy! Chapter II: Acceptance This didn't sound good. Led by his mother's hand, Alexis clattered to the darkened playroom, to open the door to find the room unusually bare. The piano was still there, the wardrobe was still there; no television, no chairs... A weird piece of furniture domin...

Mrs. Henderson Emasculates An Ex

by skriblur on Sep 16, 2017
Transsexuals & Crossdressers

The elevator doors slide shut and Sissy Kimmi taps the special access code into the keypad. Then she presses the "PH" button. In few seconds, she'll be at Mrs. Henderson's place on the top floor. Mrs. Henderson is not the type of woman who sends invitations to sissies. She's the type who tells 'guests' where to be and when to be there. Her handwritten summo...

A Phone Call

by trixie_leigh on Sep 2, 2017
Fetish

--Welcome to Mistress Wanda's World of S and M. THE home for ALL your most sick and twisted fantasies. Feel the sting of her whip. Hear the crack of her lash. Unleash your most INTIMATE desires. --If you're over 18 and have a credit card, enter the number now. --First time callers— [XXXX YYYYYY ZZZZ] --(laughter) --Very good ... Slllaavvvvvve. --Now, l...

The Training of Sissy Paula Ch. 5

by submissive~pet~ on Sep 14, 2017
Fetish

After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time. Mistress Carolyn used this to her advantage. She had a few men that liked sissy babies. The men would bring me all sorts of little sissy clothes. Dress me up and have me nurse their cocks as if they were bottles of milk. One day a new man showed up, he w...

Jasmine - Sissy Slut Transformation Pt. 01

by BillyBaroo4you on Jun 1, 2020
Transgender & Crossdressers

A Sissy Cumslut Transformation Part I - The First Taste (of cum) Nervousness crept into his mind like a snake, slithering its way down toward his stomach. He felt scared, worried about the night ahead, worried about how this one night would change his young life forever. His gentle hands began to tremble as he applied the hot pink nail polish to his finger...

Cockland Island Pt. 05

by Sissyhalo1 on Feb 3, 2020
Transgender & Crossdressers

Waking up like that I think my brain wanted not just more but to place everything that happened to me in an order that I could handle. So deeper into sissyness it was. Playing with my butt plug until I was edging myself and losing myself in it. Abby showed up. Rolled a joint and watched me. "C'mon Nikki, up, let's get you fed and working out." It was h...

Caught by the Lodger Ch. 02

by SuzieR on Sep 13, 2017
Transsexuals & Crossdressers

Over the next few months Rachel continued my training. She was determined to transform me, in her own words, into 'the perfect sissy slut girlfriend', and I was only too happy to go along with it. There are a strict set of rules that I have to follow. I am allowed to wear my male clothes when I'm out of the house but must also wear a pair of panties undern...

Humiliated Sissy Husband Ch. 02

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Max was very busy hand washing all of Tonya's underwear and lingerie in the kitchen sink. He dipped a pair of her panties in the clean rinse water dunking them several times before twisting them and squeezing out the excess water. He then placed them in the clothes basket on the counter. Tonya insisted he wear 6" heels around the house especially when doing...

Fantasies Fulfilled Ch. 02

by HerLittlePiggy on Sep 19, 2017
Group Sex

Sherry stood by the bed dressed in a black leather corset that accentuated her big 36dd tits, her tiny waist and her full hips and beautiful round ass. High healed thigh high leather boots completed her dominatrix outfit and a thick black strap on hung lewdly from her waist as she barked orders to me and the three muscular men in the room. It was September...

Jamie's Descent Pt. 02

by nikkiesilk on Sep 18, 2017
Transsexuals & Crossdressers

'That's it, baby,' Vanessa purred as she snaked her hips forwards and back, gently sliding the strapon in and out of my mouth. I could no longer think rationally, as any self control I still had slipped away and trance like, my eyes closed, I sucked the rubber phallus in and out of my lips. 'Baby, you love this don't you?' Vanessa's voice took on a hypnoti...