Rubber Sissy Stories

28,680 results
Orientation
Length
Source
Infinite Scroll

My Mistresses, Their Strapon And Me

by pantysissyslave on Sep 13, 2017
Fetish

This story was edited by: blondevixen40735 My wife, or as she is now called, Mistress Emily came into my pink princess room as I was changing for the day. She was wearing a giant strap on cock that was swinging between her legs even when she wasn't moving. My tiny cock grew a little bit in my pink satin panties. Pink was now my official color. My room,...

To the Manor Bound Ch. 03

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

[So I finally got around to finishing chapter three, apologies for the delay. As with the other two chapters this includes forced feminisation, BDSM, and non-con, so it might not be your cup of tea. Regardless do comment and email me to let me know what you think, or just to say hello!] ***** Chapter 3 -- Three Weeks after Transformation "Now it is ver...

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

Friends United

by Tomsparty on Sep 12, 2017
Transsexuals & Crossdressers

I'd been best friends with Brad since coming to the US from England as a child. We met at school and since those early years did everything together. He was very outgoing whereas I was passive. Now in our thirties we are still best of friends and even work in the same company. Brad loved motorcycles and ran a successful Harley Davidson parts distribution bus...

Textual Relations

by Pattyssissybitch on Sep 17, 2017
BDSM

PART I -- FRIDAY NIGHT My wife Patty had to go to Los Angeles for a weekend company annual retreat. When I dropped her off at the airport on Friday morning, she told me she had a surprise for me, and left it at that. I wondered all day what she was up to, and I had to wait until almost 4 in the afternoon to hear from her. When she called to tell me she'd ar...

Adventure Night Ch. 01

by Pghwriter on Sep 17, 2017
Fetish

"Yes, Mistress, I understand." In truth, I didn't really understand. I didn't understand how it was I'd gotten myself into this position, but every time She spoke, I listened and did precisely what I was told. "That's a good slut," She said into the phone, and then it went dead. I sighed. Not even a "goodbye." As I drove home from work, I realized that I...

Family Chastity Story Ch. 04

by antares34 on Aug 13, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My girlfriend Christina has been staying with me for the past sev...

Mistress Marisa's Estate Pt. 04

by keptsissy on Sep 12, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ********************************* "Butt's up ladies." She walks behind us, feel her slap my rear as she goes by. Muffled sound of her hand being brought up...

Caught in Panties & Dominated

by Tracy69 on Sep 12, 2017
Transsexuals & Crossdressers

I love to wear sissy clothes, and I fantasize about being controlled by a dominating mistress, who forces me to wear her clothes, to take her boyfriend's cock into my virgin mouth, make love to his big stiff cock, deep throating it until he comes into my mouth, filling up my mouth until his hot cum drools out of the corners of my mouth, around the sides of h...

His Sissy Bitch Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"You've come a long way, baby." He smiles at me, watches me as I cross my legs. I'm sitting across from him. I can tell the effect I have on him, every time he visits, sees me dressed fem for him, he's hard, rock hard when I meet him at the door. And I know what outfits turn him on the most. I know he fantasizes about me when he's fucking his wife. She doesn...