Officer Roland has been caught in the female barracks cross dressing in their clothes going through their knickers and being a disgusting pervert. He is sent to the Army General to receive his punishment and to discuss his future in the army.

The general is obviously a very strict no nonsense type who hasn't taken kindly to his behaviour. She orders him to bend over the trestle and lifts his skirt up to reveal stolen panties which only angers her further. he is to receive 6 strokes of the cane and is routinely humiliated due to his complete inability to take this punishment. Crying...

Officer Roland has been caught in the female barracks cross dressing in their clothes going through their knickers and being a disgusting pervert. He is sent to the Army General to receive his punishment and to discuss his future in the army.

The general is obviously a very strict no nonsense type who hasn't taken kindly to his behaviour. She orders him to bend over the trestle and lifts his skirt up to reveal stolen panties which only angers her further. he is to receive 6 strokes of the cane and is routinely humiliated due to his complete inability to take this punishment. Crying out, grabbing his bottom and making such a fuss the general soon realises this one is not made for traditional army life... but he may make it in the Sergeant Sissy program.

Once his caning is complete roland is transformed into a frilly sissy more suited to the specialist training program - here to entertain the female officers and occasionally sent under cover for interrogation purposes. The series will continue and what becomes of Sergeant Sissy will become all too clear!

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The Sergeant Sissy series:

Clip 1 Cross Dressing Court Martial

Clip 2 Internally Interrogated

Clip 3 Sergeant Sissy Cleans Up

Sissies in Space Prison :

Episode 01 available HERE Processing The Prisoners

Episode 02 available HERE Brainwashed Bimbos

Episode 03 available HERE A Deep Space Face Fucking

Episode 04 Available HERE Spit-roasted in Space Part 1

Episode 05 Available HERE Spit-roasted In Space Part 2

Episode 06 Available HERE Strokes in Space

Episode 07 Available HERE Caned By The Commanders

Episode 8 Available HERE Milked Into Another Dimension

Episode 09 Available HERE Sucked Off In Space

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Full length creative cosplay series:

Romanced and Roasted (full length)

Let Them Eat Cake (Full length) - A Marie Antoinette sissy cosplay like no other

The Prosthetic Pussy Clinic (Full length)

Sent to The Sissy Circus (Full length)

Barbie's Wet Dream House (Full length)

Consummating the Collaring

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The FFA Femme Academy with Mistress Scarlet Graves:

The Chastity Training Program

01 Your Introduction To Chastity

02 Your Device Downlow

03 The Chastity Troubleshoot

04 The Dick Shrink

05 Ruined & Denied

06 Chastity Training Stage 1 Practical

Sissy School

0 1: Sissy School Maid Training: Hair Make up and Fashion

02: Sissy School Maid Deportment

03 Sissy School: Slutty Hair, Make Up and Fashion

04: Sissy School: Slutty Etiquette

05: Sissy school Cocksuckers Masterclass

06: Sissy School: Anal Training

The Prissy Princess Program

01 An Introduction

02 Make Up

03 fashion

04 The Commandments

See more of My sissy rosie in the following clips:

Consummating The Collaring

Exposing Rosie Part 1

Exposing Rosie Part 2

Exposing Rosie Part 3

Thrashed and Blackmailed

Romanced and Roasted

Roasting Rosie

The Sissy Circus as separate episodes - with Mistress Scarlet Graves

Part 1 Made To Join The Sissy Circus

Part 2 Bullying Krustina

Part 3 Puppy Mayhem at The Sissy Circus

Part 4 Buttplugs and Balloons part 1

Part 5 Buttplugs and Balloons part 2

Part 6 Sissy Clown gets a salty Pie

See more of sissy Cherry Here:

The Bedroom Boot Bitch

A Slutty Spitroast

Trained & Purged

Bimbo Gets Banged