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11

Stories

Stories by sissysherry2

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Series: ExpandedSeries: Combined
A Surprise Blind Date

An Innocent party turns into something more.

by sissysherry2
BDSM 07/04/2019

4.03 12.2k 3 3 9

Another Sissy Shopping Adventure

Another sissy shopping assignment from a young mistress.

by sissysherry2
BDSM 07/15/2018

3.81 27.8k 6 5 14

Sissy Shopping Adventure

A sissy heads to the mall for some pure humiliation.

by sissysherry2
Transgender & Crossdressers 05/10/2018

4.33 55.3k 25 11 40

Tables Turned at the Mall 2 Parts
by sissysherry2
BDSM06/08/2023

74.6k 32 5 58

1
Tables Turned at the Mall

A sissy gets more than she reckoned with at the mall.

by sissysherry2
BDSM 04/20/2018

4.15 47.5k 23 3 44

2
Tables Turned at the Mall Ch. 02

The action heats up after a sissy is outed by young girls.

by sissysherry2
BDSM 04/28/2018

4.14 27.1k 9 2 14

Hung like a Grape 3 Parts
by sissysherry2
Transgender & Crossdressers06/08/2023

162.8k 77 23 123

1
Hung like a Grape

A small dicked Sissy is outed and humiliated.

by sissysherry2
Transgender & Crossdressers 04/01/2018

4.08 97.4k 46 14 85

2
Hung like a Grape Ch. 02

Lisa continues to strengthen her hold over Sherry!

by sissysherry2
Transgender & Crossdressers 04/05/2018

4.11 36.2k 18 2 24

3
Hung like a Grape Ch. 03

Sherry entertains some new friends at Lisa's party!

by sissysherry2
Transgender & Crossdressers 04/07/2018

3.96 29.1k 13 7 14

The Babysitter Takes Over 3 Parts
by sissysherry2
BDSM06/08/2023

195.6k 53 23 95

1
The Babysitter Takes Over

A closet Sissy is discovered by a teen babysitter.

by sissysherry2
BDSM 03/05/2018

3.83 96.4k 31 10 58

2
The Babysitter Takes Over Ch. 02

Teri the babysitter ups the ante with her sissy.

by sissysherry2
BDSM 03/13/2018

4.29 53.5k 10 7 19

3
The Babysitter Takes Over Ch. 03

Our sissy gets in deeper by the babysitter and others!

by sissysherry2
BDSM 03/14/2018

4.09 45.7k 12 6 18

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