Sissy Pee Stories

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The Prostate Exam Pt. 04

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by not being able to resist pushing back against her finger, forcing her finger deeper into asshole. At that point his female doctor had decided to test just how submissive he was. She gave him the option to back out if he...

What Just Happened? Ch. 02

by annie_00 on Sep 12, 2017
Transsexuals & Crossdressers

02 – Am I a pervert? When we got home it was late in the afternoon. We had been gone all day, first to the salon, then shopping, lunch, drinks and the crossdresser store. I was tired but felt very sexy under my clothes. I did not want Beth, my step sister, to know that I totally enjoyed the experience today. I thought that she would think I am perverted. A...

AliExpress and Sissy Downfall Pt. 05

by His_fag_wife on Feb 6, 2018
Transsexuals & Crossdressers

Charlie was deep in it now, being assessed by Miss Bell the beautician before she started work on removing all of Charlies hair below her soon to be plucked eye line. Candice the young pretty petite receptionist was also looking on to deepen Charlies humiliation. "Miss Bell, I'm really tight, but even my little pussy couldn't be satisfied by that little cli...

The Bet

by ksu328 on Aug 31, 2017
Fetish

Let me first setup the situation, I have been friends with this guy for about the last 10 to 12 years. His girlfriend, Tyler, had this friend named Jen. I was totally in awe of Jen, she was so beautiful. I am not exactly good with the ladies, so when I finally asked her to go out, she gave me an emphatic "NO!!" So now she knew that I liked her, she took full...

Sissy Slut Ch. 01

by Scribler on Sep 13, 2017
Transsexuals & Crossdressers

It had been quite some time since I had stopped in the club. Not that I didn't crave the pain I could infect on one of the sweet young things that came to the club. I craved it more now then I ever did a few years ago. But due to relocation of my job I had to leave the city and I couldn't find a club that catered to my needs. Now I was back and I was chompin...

My Little Slut Ch. 02

by Sweetblood03 on Sep 12, 2017
Fetish

"My apologies, Mistress." He pulls up the flimsy black knickers over his softened cock, bends his head and begins to lick the pooled cum off my sleek black boots. "You realize that this means a day with the cage on for your forgetfulness, don't you, pet?" I reach down to stroke his cheek while his tongue works over the leather catching every last drop of c...

Welcome Home, Ma'am

by Miss_Ds_slave on Sep 12, 2017
BDSM

He had been waiting his whole life to find someone like her. He had almost given up any hope that there was someone out there who could give him what he so needed. He had met a few women over the years that had been willing to try and give him what he desired, but it was usually just something they did for him, not something they enjoyed for their own pleasu...

High School Dilemma Ch. 06

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. PLEASE DON'T READ THIS IS YOU HAVE AN AVERSION TO PEE SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only wish there is enough here to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. I...

The Sissy and The Gardener

by snorn on Sep 16, 2017
Transsexuals & Crossdressers

As I sit in my office, I am wearing my pink sissy uniform, watching the hired gardener dig up the weeds out front. I'm not supposed to expose myself to others, but my sissy rules state that I must be in uniform when nobody else is inside the house. I'm doing work, but all I can really concentrate on is the idea that I should be on my knees sucking cock, or b...

Lock And Key

by ksu328 on Sep 1, 2017
Fetish

As the first snow of the season started to fall on my small hometown, my sex life started to make a turn just like the seasons. Well, I guess since I've never really had a sex life besides jacking off my little pee-pee, you could say that my sexual freedom was changing. The little box (ironic that it came in such a small box) arrived on a Wednesday and as m...