Sissy Butt Plug Stories

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Orientation
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Infinite Scroll

Another Submissive Slut Ch. 09

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

As I watched Teddy perform I absent mindedly sucked gently on the stiffing cock in my mouth. My head rested on the fat owners hairy gut as I nestled between his thighs. His hands stroked my hair and body leaving me tingling with arousal. My drug addled body quivered with anticipation as I hummed my building passion over the rigid man cock. Teddy was eying...

The Entertainment Ch. 01

by econut on Sep 26, 2017
Fetish

(This series is a continuation of the story line from 'Finding My Place'. It can be read alone, but why not start from the beginning?) * It had been a month since the first weekend I had spent serving as a live-in maid and sex slave to Lana and Gary, an attractive, sexually dominant couple. Since then, I had been to their house serving them every weekend...

Mistress Jaz's Sissy Slut

by barbiboi on Aug 30, 2017
Fetish

Mistress Jaz had invited me over to give her a pedicure and provide sissy maid service. What I got was a mind blowing day of servitude I will never forget! I arrived in the morning and was greeted by a vision of beauty. I had seen pictured of Mistress Jaz before, but they paled in comparison to meeting this incredible Goddess in the flesh. Tall, curvy, wit...

Trixie's Chastity 01

by trixie47cd on Sep 19, 2017
Transsexuals & Crossdressers

Part 2: Trixie learns his new role. Since my wife came home early and caught me masturbating in women's frilly lace 2 month ago, so much has changed. She has taken control of my life since I begged her not to spread the story and pictures of my humiliation around town. After I made the choice of submitting to her feminization training, there really was no...

Danni Ch. 02

by Coder3445 on Jan 20, 2020
Transgender & Crossdressers

This story starts where the last left off, read Danni to understand what is going on in this story. Of course all character are above the age of 18. The following story contain feminization and female domination. * Also another description Tara, Danni's Mother Unlike Danni Tara had tanned skin, she was five foot four inches tall. She had green eyes and...

The Prostate Exam Pt. 02

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 submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...

My Dom's Decisions

by davesubboi on Oct 12, 2017
BDSM

The thought of being submissive and letting another superior being guide, direct and change me has become one of my driving desires. Over the past 15 years I have realized I am much better at pleasing others and have determined based on numerous online doms/master/mentors that I really should not care about my own pleasure if I can serve another and give the...

I Adore Crossdressers Pt. 04

by Ab9095 on Dec 3, 2018
Transgender & Crossdressers

Day 3 When she left last night she was a very happy girl. I have her clean up. Redo her makeup. Get her pretty. And then she has to leave like that. She makes me promise she will see me tomorrow. I actually have a hard time sleeping that night. She's running through my mind and I'm thinking about tomorrow. I send her a text in the morning telling her to...

Sissy Hotel Play

by elliotsconfessed on Dec 24, 2018
Fetish

It was a Friday afternoon and I was feeling a little bored and some what curious... I had spent the last hour or so watching porn, but not just the usual straight type of porn I'd usually watch... For some reason I had an urge to watch men fuck other men and have guys dress up as girls and fuck themselves with toys! I was so turned on and a little confus...

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...