Hobble Skirt Stories

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Infinite Scroll

Penance Day Ch. 03

by HartMann on Sep 15, 2017
Fetish

This is the sequel to "Penance Days Ch2". Enjoy, and if you do, please leave a public comment. Thanks. * "My daughter is sometimes so old-fashioned," she looks at me inquisitively, then continues, "but now that she is gone, let us go inside." She stands up, walks over the porch and I hear her disappear into the house. Damn, what a great ass she has.... S...

Best Laid Plans Ch. 05

by Julirose on Sep 16, 2017
BDSM

The sound of Helen's phone ringing awakened him; a quick glance at his watch told him that it was seven o'clock. Forgetting where he was, he picked up the phone and answered, "Hello?" "I'm sorry," the woman on the other end apologized, "I must have dialed a wrong number. I was trying to reach my daughter, Helen." Ryan suddenly remembered that Helen had tal...

Age/Sex/Location

by LeanneSinclair on Sep 14, 2017
Humor & Satire

The scene: a text-only cybersex chatroom. "MistressLisa" has just invited "bi_curious_debbie" to a private chat. The following conversation ensues. MistressLisa: Hi, how are you? bi_curious_debbie: fine thanks, you? MistressLisa: Good thanks. A/S/L? bi_curious_debbie: Sorry i'm new here. Whats ASL? MistressLisa: Age/Sex/Location. bi_curious_debbie: Oh...

My Story

by JenniferWilson on Aug 18, 2017
Fetish

This story is a result of Jon, who commented on one of my fiction stories and asked me how I became a latex / PVC fetish. My story with respect to my loving of latex and PVC begins about 20 something years ago. Whilst at uni a group of us girls, especially Edith my best friend, would get together at weekends for parties and good times with the boys. One pa...

Cold Sweet Revenge Ch. 04

by grgy56 on Nov 2, 2020
Transgender & Crossdressers

Arabella's Step-father Stu was faced down on the chesterfield. His pants pulled down and his bare ass up. Arabella's hard erection nudged against Stu's shit hole. Stu begged Arabella to stop and clinched his butt cheeks as tight as he could. Arabella pushed down harder on his neck which raised his hips and kicked his legs apart to lessen his resistance. She...

Her Doll Ch. 01

by WickedDoll on Sep 16, 2017
Transsexuals & Crossdressers

'What would you like, girls?' Quietly amused, I smiled at Samantha who eagerly gave our drink order as we settled into a corner booth at one of his favorite alternative lifestyle bars. Or should I say her. No difference. Sam was Samantha during the weekend and I was accepting of his chosen uniqueness. As long time friends, I knew it pleased him when he was...

A Night Drive Pt. 02

by 13feathers on Jan 22, 2019
Transgender & Crossdressers

The rest of the drive to the station was tedious and not at all erotic. Once my arresting officer had parked, and cut the rope connecting my bound wrists and feet and untied my ankles, he escorted me out and up the stairs. They were painful to climb with how limited my movement was, but I managed. Entering the building I found the main hall was mostly a coll...

Plan gone wrong

by Indiansisst on May 30, 2019
BDSM

I was really excited about my 3 month trip to noida. I was finally going to live out my fanatsy of being dressed like a girl full time. A little about myself i am a guy 18 year old, i am really into crossdressing and bdsm. And my only chamce to live this fantasy was my this trip to noida. When i arrived in noida the first thing i did is took out my only pair...

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Becoming a Sissy Maid & Slut Vol. 13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Two: Satin, Ruffles and Lace, Sissy Maids contracted out to Work. Monday morning and I arise as typical at 7:30am, enema, shower, shave do my makeup and put on a maids dress for the day. Today it's back into a black satin one. Master told me though to put on black back seem pantyhose for today which I dutifully do and make sure the seems are...

(Cross) Dressing for a Latex Party Pt. 02

by latexlegs on Sep 25, 2017
Transsexuals & Crossdressers

Only once we were in limo and on our way, did I notice that my wife had brought along a little PVC backpack. I was curious to learn what was in it, but she advised that I need to be patient and it will be well worth the wait. My wife also whispered in my ear that seeing me dressed up like a latex slut that had got her extremely turned on and that combined w...