Sissy Anal Training Stories

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Neighborly Relations Pt. 02

by grizzley123 on Jan 15, 2019
Fetish

NOTE: I always appreciate comments. You can read my slightly longer message on the first part of the story, but the gist is... I like my themes, you might like other ones. But I always enjoy comments, regardless of their content. **************** It helps to read part one where my neighbor starts to take control of me by using his incredibly hot step-daugh...

Anal Training Ch. 03

by Catchandrea2397 on Feb 3, 2020
Transgender & Crossdressers

Hello pet. Welcome back. Are you ready for the next stage in your training? Good. You're such an eager obedient pet aren't you? Such a slut. Today you are going to need the following items - Bra and panties - Stockings, ideally with suspender - Butt plug - Vibrator/dildo - Lipstick - Perfume You will also need plenty of time. I'm not going to...

A Girl And Her Sissy

by TollWard on Sep 18, 2017
Transsexuals & Crossdressers

Life is good. Life is really, really good. As I write this I'm sipping on a very expensive wine and wearing a very expensive dress while sitting in my very expensive apartment. I no longer work, having not needed to earn my own income for little more than a year now. That probably leads you to wonder how I pay for all my nice things. Well while I enjoy my lu...

Mistress Red Fox Becoming a Devotee

by His_fag_wife on Sep 24, 2019
BDSM

A story of what might have been a dream. Names have been changed. *** One evening I was looking through profiles on a BDSM website and came across one for a local Mistress, she was developing a new dungeon and she was asking for suitable subs for her to try it out on. Someone to test the new equipment and layout on. I read the ad over and over again, this...

Internet Meeting

by Stillherer on Sep 16, 2017
Fetish

We met on the net. How modern. He was shy and nervous, very much like I was though if anything even more cautious. Being a closet cross dresser with a life outside my apartment door my main aim was discretion and major fear -- discovery. Charles appeared to be perfect for my yearning to fulfill my fantasies and spice up my solo adventures. We chatted online...

A Night at the Club Pt. 01

by Jemina004 on Sep 14, 2017
Transsexuals & Crossdressers

Dani nervously looked at his reflection in his trusty compact mirror. He was sitting in the passenger seat of Keyshawn's black Escalade, about to enter one of the most exclusive clubs in the city. His mascara made his naturally thick eyelashes flutter attractively, his eyeliner perfectly framed his blue eyes, and his Candy Apple lipstick was flawlessly appli...

On a Scale of 1 to 10

by His_fag_wife on Apr 17, 2019
Transgender & Crossdressers

He couldn't help himself, it was a new office environment for him and she truly was stunning. Even her little sister Claudia was delightful and sexy, but in a more understated way. The fact that she worked for Georgia her sister, set the hierarchy, but even more so, Georgia towered over her younger sister, and then there was Georgia's innate sense of style a...

Neighbors Sissy Son

by newfield1981 on Sep 18, 2017
Transsexuals & Crossdressers

About two months ago a woman and her son moved into the vacant apartment next to mine. I noticed right away how effeminate the son was, even though he was dressed like any other 18yr old boy, he couldn't have weighed more than 115lbs and his facial features were soft and delicate! Having a thing for femboys (twinks) I set my sights on this one! Since I wor...

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,...

New Gurl in Town Pt. 02

by GavinIsaNuisance on Oct 5, 2020
Transgender & Crossdressers

This story and its contents is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual manner are 18 and up. Andy begins his sissy adventures as Bianca, but will he be able to woo his crush Riley, or will he be forced to be Carol's bitch forever? We...