Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

Caught by My Bully and Exgf Ch. 02

by CindyTightass on Sep 15, 2017
Transsexuals & Crossdressers

This is second chapter of story about young crossdresser who is discovered by his ex girlfriend and masculine bully from high school. All protagonists of this story are consenting adults. ***** "Your face is a one big mess Cindy," said Michelle giggling, "let's go to the bathroom and clean you up!" She helped me to get up from my shaky knees and led me to...

Hubby Drop To Thy Knees! Ch. 02

by Ashesh9 on Sep 17, 2017
BDSM

CH. 2 :HUSBAND , BEND OVER & PART THY NETHER CHEEKS !!! Her ringing , humiliating command was heard all over the field “Husband, bend over the Punishment Table, bare thy delectable, horny bum & part thy nether cheeks for Thy Royal Monarch’s Pleasure !!! Immediately!!! Do it now, boy !!!!” The sweet girlish voice, the Commanding tone, the embarrassing Orde...

Jack and Jill Pt. 05: Thailand

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

The decision to move to Thailand was a big one, but Jill was glad that they had done it. Here they could live out all of their sexual fantasies in total freedom, without judgement or harassment. She had completed Jack's feminisation by insisting he had breast implants when they arrived, but that was months ago and they were all healed now. She loved to grab...

Cuckolding Sindy

by SindySuxALot on Sep 13, 2017
Transsexuals & Crossdressers

Domina Lucy Sissy Sindy sat in her room staring at her computer monitor. Her mistress Lucy had ordered her to stay in here and watch gay fisting videos. Her eyes watched the screen as closely as she could since she knew she might be tested on the content later. She was mildly distracted from the video by the huge vibrating plug inside of her sissy pussy. I...

Sissy Awakening Ch. 03

by Torbjornson on Oct 5, 2020
Transgender & Crossdressers

Standing at the living room window with the windex and paper towels, I teetered on the ridiculously tall Mary Janes. It were as though I were standing on the balls of my feet and toes only. There was no relief. My other pumps felt like heaven compared to these! She said to wash inside and out, and not to miss a spot. That meant I'd have to go outside. It wa...

Sissification 101: Ch. 05

by silkstockingslover on Aug 31, 2020
Interracial Love

Sissification 101 Ch 05 Summary: Erica practices taking BBC in both of her sissy holes. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught by a very supportive girlfriend in pantyho...

Mistress Melody Visits

by RobinTVDaniels on Sep 19, 2017
Fetish

Today is the day that Melody arrives. We have been talking over the phone for a while now before we arranged a meeting. I have cleaned the house from top to bottom. I have scented candles and I also got a dozen roses and sprinkled the petals from the front door to the bedroom. I leave the house and head for the airport. A nice black limo will be meeting me t...

The Alpha Who Made Me a Sissy Ch. 01

by HB77 on Jul 31, 2019
Transgender & Crossdressers

So there I was again on all fours in his bed. My peach coloured thong panties pulled to the side, and my daddy behind me with one hand on my hip and the other Gripped onto the back of my red corset. Chad relentlessly filling my ass pussy with his gorgeous rock hard 8" as I moaned "oh daddy, oh daddy don't ever stop fucking me, I love you" over and over in my...

Sissy Chantel, New Reality Ch. 04

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Four: More Sex, Public Humiliation and a Soon to be Turn for My Sissy Life. 8:00am and my alarm clock goes off, I am groggy as I awake but I soon realize I'm about to have another exciting sissy day with Master Camron and Sir Gage. I quickly shower and do myself up as expected in, make up, wig and my black maids dress, black sheer pantyhose and blac...

The Slave and the Sissy Ch. 05

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

Ayesha was not to be denied; slave was rampant after witnessing the erotic antics of the maids, and was anxious to please Ayesha quickly, so that he may watch over Pepper; she was so soft and vulnerable. Slave's cock rose quickly as he sniffed at the gloriously rich scent of the dusky beauty's thong. She smiled with a sense of admiration as he licked and lap...