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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
4.13 13k 5 3 7
Another Sissy Shopping Adventure

Another sissy shopping assignment from a young mistress.

by sissysherry2
BDSM 07/15/2018
3.87 29.3k 8 5 10
Sissy Shopping Adventure

A sissy heads to the mall for some pure humiliation.

by sissysherry2
Transgender & Crossdressers 05/10/2018
4.35 58.6k 29 11 17
Tables Turned at the Mall 2 Parts
by sissysherry2
BDSM06/08/2023
78.8k 39 5 28
1
Tables Turned at the Mall

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

by sissysherry2
BDSM 04/20/2018
4.19 50.3k 27 3 23
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
4.07 28.5k 12 2 5
Hung like a Grape 3 Parts
by sissysherry2
Transgender & Crossdressers06/08/2023
171.2k 86 25 60
1
Hung like a Grape

A small dicked Sissy is outed and humiliated.

by sissysherry2
Transgender & Crossdressers 04/01/2018
4.09 102.3k 51 16 47
2
Hung like a Grape Ch. 02

Lisa continues to strengthen her hold over Sherry!

by sissysherry2
Transgender & Crossdressers 04/05/2018
4.15 38.1k 19 2 10
3
Hung like a Grape Ch. 03

Sherry entertains some new friends at Lisa's party!

by sissysherry2
Transgender & Crossdressers 04/07/2018
4.01 30.7k 16 7 3
The Babysitter Takes Over 3 Parts
by sissysherry2
BDSM06/08/2023
206.5k 54 25 60
1
The Babysitter Takes Over

A closet Sissy is discovered by a teen babysitter.

by sissysherry2
BDSM 03/05/2018
3.84 101.9k 32 11 42
2
The Babysitter Takes Over Ch. 02

Teri the babysitter ups the ante with her sissy.

by sissysherry2
BDSM 03/13/2018
4.23 56.5k 10 8 11
3
The Babysitter Takes Over Ch. 03

Our sissy gets in deeper by the babysitter and others!

by sissysherry2
BDSM 03/14/2018
4.12 48k 12 6 7