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Sleepyheadjess NSFW GIFs and Nudes - Discover Unknown Content

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sleepyheadjess
Sleepy-Head Jess

Users

0

Media

18

Created

11/13/2023

Description

Tall and sometimes beautiful. Crossdresser and submissive. Kindness and courtesy are important to me. Likes books, 1950s fashion, cooking, pretentious movies and dogs. Seling panties and custom vids
Pink or blue?
Pink or blue?
r/SissyChastity
u/sleepyheadjess 9 months ago

56

Pink or blue?
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12
Why does this make me feel so wonderful?
Why does this make me feel so wonderful?
r/SissyChastity
u/sleepyheadjess 9 months ago

2

Why does this make me feel so wonderful?
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My favourite chasity pics are from just after a fresh shave!
My favourite chasity pics are from just after a fresh shave!
r/SissyChastity
u/sleepyheadjess 10 months ago

104

My favourite chasity pics are from just after a fresh shave!
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3
Painted my nails and plugged myself because a stranger on the internet told me to
Painted my nails and plugged myself because a stranger on the internet told me to
r/sissies
u/sleepyheadjess 1 year ago

34

Painted my nails and plugged myself because a stranger on the internet told me to
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13
T-bar Mary Janes and pink chastity cage make me feel innocent and horny at the same time!
T-bar Mary Janes and pink chastity cage make me feel innocent and horny at the same time!
r/SissyChastity
u/sleepyheadjess Jane.chastity 1 year ago

112

T-bar Mary Janes and pink chastity cage make me feel innocent and horny at the same time!
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Going to spend a whole day caged for the first time. Wish me luck!
Going to spend a whole day caged for the first time. Wish me luck!
r/SissyChastity
u/sleepyheadjess 1 year ago

450

Going to spend a whole day caged for the first time. Wish me luck!
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43
Tied a little bow around my cage
Tied a little bow around my cage
r/SissyChastity
u/sleepyheadjess 1 year ago

97

Tied a little bow around my cage
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15
Welcome home darling, what would you like to use on me first?
Welcome home darling, what would you like to use on me first?
r/GoneWildCD
u/sleepyheadjess 1 year ago

7

Welcome home darling, what would you like to use on me first?
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Leaking in Agent Provocateur
Leaking in Agent Provocateur
r/men_in_panties
u/sleepyheadjess 1 year ago

23

Leaking in Agent Provocateur
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10
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