Sissy Pantyhose Stories

12,794 results
Orientation
Length
Source
Infinite Scroll

Black Sissy For White Queen

by Samuelx on Sep 16, 2017
Interracial Love

I feel so damn great as I slide my strap-on dildo deep inside Ramon Jones. The six-foot-tall, skinny Black guy looks absolutely gorgeous in a bright pink dress, white pantyhose and high-heeled red shoes. His face is perfectly made up, rouged and his makeup and lipstick are applied nicely. The fuzzy black wig he's wearing only adds to his decidedly not so mas...

Mikey becomes Melodie

by tiffanyfoxe on Jul 14, 2020
Transgender & Crossdressers

The very first day that I met Heather she made it clear to me that sex was very important to her. That same night, when she first saw me with my pants down, she explained that since my penis was way too small to ever satisfy her, she expected me to service her with my tongue and lips whenever she wanted. All my life I'd always loved fantasizing about being...

Randi Michelle's Sissy Subjugation

by Randi_Michelle on Sep 16, 2017
Transsexuals & Crossdressers

To me, part of the process in my case of stripping me of my masculinity involves documenting my transformation and the humiliation that it would involve. For me it started through an encounter with a dominant man who enjoys feminizing submissive males and turning them into 24/7 gurls. It just took the right dominant man to make it happen for real. I've spen...

Pay for Pleasure - Prequel

by Pleasure_the_slut on Sep 16, 2017
Transsexuals & Crossdressers

I had written about how Sandy turned me into a $50 whore before writing about how I got to that point with her. I was cruising an online posting for sex one Thursday evening and I came across a posting for TV looking for big cock. Well that got my attention, I'm 8" and very thick. So, I shot a reply right away. Not a minute later Sandy and I started chatti...

Sissy Nicky

by call_me_dana on Sep 2, 2017
Fetish

"Please don't make me open the door like this," Nicky begged to Angie. "Then you should have had your chores finished before I got home like I instructed. Don't keep Sonya waiting." Nicky slowly moved to the door as the bell rang again. Nicky could feel himself blushing as he opened the door. Sonya was standing on the porch and he could see the look of sho...

Sperm Bank Artists Pt. 02

by wordyone on Nov 18, 2019
Fetish

The writer recommends that the reader is familiar with the first part of this story. 'Sperm Bank Artists'. All characters are beyond adult legal age, and the theme is male masturbatory humiliation at the hands of young female artists. The women artists collect ejaculate and use it for their artworks. 'Sperm Bank Artists. Part II: Olivia and Cath' coincides...

The Process

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

A few of my loyal follower's of Desiree's Hot To Trot Transvestite Adventures have asked me how I summon the nerve to be a cock sucking slut with a complete stranger. You see one of my earliest tricks in the annuals of Desiree was to dome light truckers heading down lonely highways. A glimpse of long shapely leg in a five or six inch heel generally was all...

Threshold of Desire Ch. 4

by Cuthbert on Sep 19, 2017
Fetish

Chapter 4: Maid service Three weeks had passed since our last 'special' time, yet it still angered me when I thought about your transgressions that evening. Your first transgression, of 'forgetting' to shave your face as directed, had earned you a fitting punishment – being made to shave your legs, balls, and pubes as a 'reminder.' But the second transgress...

Behavior Modification Institute Ch. 05

by NancyPan on Sep 12, 2017
Fetish

"I am so proud of you, Tom," Ms Jensen said warmly, approaching me and taking my hands in hers, "It will help you so much to accept this about yourself, Tom. We will help you turn the fantasy of being a sissy into the reality of sissy life. Ms. Panington will be pleased with this progress, and I am quite sure that Kelli will be pleased as well. Let's get you...

Pretty in White Ch. 01

by wendy_james on Sep 16, 2017
Transsexuals & Crossdressers

Pretty in white... That's what my Mistress whispered in my ear after she finished dressing me in a white bra, a white knit camisole, a white linen blouse, white sheer pantyhose, and the palest-of-pink panties over them. She stood me in front of her full-length mirror in her dressing room, and she came up behind me. I was wearing white open toe sandals with...