Sissy Stockings Stories

45,315 results
Orientation
Length
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Infinite Scroll

Using Her sub

by aSub2fems on Sep 13, 2017
Fetish

Early one September morning I awoke to find a strange letter laying on the pillow next to me. It appeared that Nikki, my girlfriend, had already gotten ready and left for the day. Assuming that it was just an "I love you" note, I went into the bathroom to begin my own day. When I arrived in the upstairs bathroom I found a pair of black satin fullback panties...

Story of a Sissy Cuckold

by HughJanus on Oct 24, 2019
Fetish

Hi there, my names Michael but everyone just calls me Mike, i'm a 46 year old guy, i was an average guy living an average life, married to the love of my life, her name is Samantha. Shes my high school sweetheart, we dated all through high school then when we graduated we got married. She still has a smoking hot body, even all these years later, she works ou...

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A Week End with Mistress Pt. 02

by gasissynora on Oct 30, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** I arrive at Mistress Nikki''s a couple of minutes before 2:0...

Wife in Control Ch. 07

by wifetoy on Sep 25, 2017
Fetish

This is the seventh chapter of my wife's fulfillment of the punishment poem I submitted suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I am grateful that my wife loves me enough to exercise the total control over me tha...

Crossroads

by Hecate on Sep 25, 2017
Transsexuals & Crossdressers

I can't believe I'm really going through with this, but yet, here you are - my husband whom I thought I had known inside and out... laying on the bed there in front of me, wearing... white skimpy satin panties with delicate lace embroidery and a matching bra... and bent over you, just closing the clasp behind your back and adjusting the soft and slightly shi...

The Initiation Ceremony

by DrLuverotica on Oct 21, 2019
Transgender & Crossdressers

FRIDAY A.M "Don't forget I'm out at Carrie's hen party tonight." Jo said, as she was just leaving for work. "Carrie, your secretary?" "That's right, Carrie my very sexy secretary." "Will you kiss a girl and like it?" "You wish!" "A boy can fantasise." "Well let's hope Carrie's got some nice fantasy games lined up. Or a male stripper or two." And with...

Office Cumslut Ch. 01

by DrLuverotica on Sep 12, 2017
Loving Wives

FRIDAY MORNING "Are you going to work dressed like that Jo?" My wife was dressed in black, sexy high heels, black stockings with a pink 1920s style pencil line up the back of them, pink frilly satin panties (she hates thongs) and matching push up bra. "Yes I am hubby," she purred, as she pulled a navy blue, short pleated skirt over her hips. "Is there s...

A Mistress, a Sissy, and a Slave Ch. 01

by thejm4n on Sep 15, 2017
Fetish

Clad in a skintight, black latex dress, and tall, 4 inch platform black heels, Jessica was a stunning figure as she looked down at her two slaves, on their knees. "Up" she said to Hailey. "Yes Mistress Jessica." Hailey stood, naked, save for the black collar around her neck. "Now" Jessica said, looking at the other slave, "it's time for a little fun with...

April Fool Office Sissy

by lululuvsblack on Apr 10, 2018
Transsexuals & Crossdressers

"Dear Colleagues This week, in order to help with our efforts to raise money for charitable causes, we have decided to mix up our usual policy of dress down Fridays. This Friday we are instead instigating a "dress up Friday" in which staff are strongly encouraged to come to the office dressed in the office attire of the opposite gender (that's suits and tie...

Sissy Life

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I kept staring at the strap-on. I couldn't understand why it was out on the dresser. I tried not to let the concern show. I stood up straight - stood to attention - and thought back to the conversation that had led me here.... I was just finishing the washing up when my Mistress came into the kitchen. This in itself was unusual. Usually if she wanted me, s...