Anal Sissy Stories

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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...

Mark Ch. 01

by evangelick_my_balls on Dec 12, 2018
NonHuman

1 The beginning of the gospel of Jesus Cum, the Son of Godcock; 2 As it is written in the pornos, Behold, I send my messenger before thy face, his cock hard and throbbing, which shall prepare thy anal way before thee. 3 The voice of one crying out in ecstasy in the wilderness, Prepare ye the way of the Lord, make his paths straight and his dick hard. 4 Jo...

My sissy sister

by Alana-S on Jun 9, 2020
Transsexual

Did I really want this? That question had haunted me for weeks now. For years sissy porn had been my main masturbation fodder, and two months ago I had decided it could be more. That I could be more. I always wanted to be pretty like girls were, and had been openly bisexual for years. Why not try this? Why not be a sissy? I signed up to an online feminizatio...

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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...

Joel Gets Caught by His Wife

by Downforeverything on Sep 18, 2017
Transsexuals & Crossdressers

This is a fictional story written for a fan about their sex life. If anyone else has a story they'd like written for them about fact or fictional events feel free to message me. As always please leave comments or constructive criticism so I can make your pleasure better! * It was Monday afternoon. Joel had taken the day as an opportunity to work from home...

Becoming a Sissy Maid & Slut Vol. 02

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Four: My Arrival and a New Start to Full Time Sissy Life. I awake about 7:30am, groggy as I only had a floor to sleep on with a thin blanket, I rub my morning eyes as I sit up and see the black, satin, maids dress on a hanger, as if it was calling me to put it on. I soon realize my new predicament and smile. I had to take off the pair of pantyhose,...

Under Mommy's Direction Ch. 05

by MommysHypnoSissy on Apr 13, 2020
Transgender & Crossdressers

The rest of Jaime's day had been a whirlwind of tasks and chores to complete before his Mother got home. His online Sissy Trainer, who demanded that he refer to her as 'Mommy', had given him a myriad of tasks. First it was cleaning up his Mother's bed and sexy toys, putting everything back how he had found it. Then it was back to his room to dispose of his b...

Simon Sissy Slave Ch. 03

by Timewarp10 on Jul 30, 2019
BDSM

Mr Berne watched with satisfaction as the sissy paraded in the post room. Sissy walked gracefully in high heels. His ballet training made it easy. He knew how to walk like a woman. He had practiced, and he could walk with a book balanced on his head. It gave him poise, and the high heels gave elegance to his calves. The skirt was short enough to look slutty,...

A Toy Party Story

by lushusboobs on Sep 11, 2017
Transsexuals & Crossdressers

Toy Party Story Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him. He explained that he felt so vulnerable and powerless as a woman and that it was exactly the opposite of his everyday life where he held mu...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...