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Sissy dare...
Sissy dare...
Bet Dare Non Nude
27 49 1
First sissy dare
First sissy dare
Comixx Crossdressing Maid
5 17 0
Lost at True and Dare
Lost at True and Dare
Caption Sissy Sissy Caption
8 12 1
Do you dare to look and leave your night to chance?
Do you dare to look and leave your night to chance?
Censored Pussyfree Sissy Censored
0 0 0
Dare a sissy go to a party like this?
Dare a sissy go to a party like this?
Crossdresser Sissy Sissy Crossdresser
26 66 1
I dare you send me
I dare you send me
Caption Motivation Sissy
23 50 0
Brainwash yourself into a cock craving sissy
Brainwash yourself into a cock craving sissy
Crossdresser Dare Self Bondage
15 37 0
Sissy's should always be dressed appropriately
Sissy's should always be dressed appropriately
Crossdresser Dare Maid
13 29 1
Be sure to dip your sissy toes in the sea as well
Be sure to dip your sissy toes in the sea as well
Beach Crossdresser Dare
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You want to be caught by your neighbor, don't you sissy!
You want to be caught by your neighbor, don't you sissy!
Caught Crossdresser Dare
58 111 0
When truth or dare at the sleepover gets out of hand
When truth or dare at the sleepover gets out of hand
Bukkake Cumcovered Facial
31 44 0
Don't you dare interrupt me
Don't you dare interrupt me
Caption Chastity Cuckold
25 73 3
Your chance to out in public with no fear
Your chance to out in public with no fear
Crossdresser Dare Pride
33 58 2
Ask the cashier if he would mind seeing if it suits you,
Ask the cashier if he would mind seeing if it suits you,
Crossdresser Dare Sexshop
42 32 12
The truth game
The truth game
Caption Dare Sissy
25 44 0
This is what you practised for.
This is what you practised for.
Crossdresser Dare Gloryhole
20 47 0
Extra points if you "accidently" address it to next door. Then you have to knock on the door and ask. Hopefully they didn't open it.
Extra points if you "accidently" address it to next door. Then you have to knock on the door and ask. Hopefully they didn't open it.
Caged Chastity Crossdresser
18 42 2
Ask him how he'd like you to pay.
Ask him how he'd like you to pay.
Crossdresser Dare Delivery
15 42 0
Your now his pet bitch
Your now his pet bitch
Blowjob Crossdresser Dare
8 37 1
Brainwashing with a cold shower
Brainwashing with a cold shower
Crossdresser Dare Shower
9 31 2
You're going to get quite a few looks.
You're going to get quite a few looks.
Crossdresser Dare Lingerie
10 31 1
Think of all the fun you'll have together
Think of all the fun you'll have together
Crossdresser Dare Lingerie
8 22 0
Those leather seats can get quite sticky.
Those leather seats can get quite sticky.
Car Crossdresser Dare
12 16 0
The fear of your door opening makes your clitty ache in its cage.
The fear of your door opening makes your clitty ache in its cage.
Crossdresser Dare Femboy
3 21 0
Doing the washing is exciting
Doing the washing is exciting
Crossdresser Dare Lingerie
8 16 0
The shame only turns you on even more
The shame only turns you on even more
Crossdresser Dare Sissy
9 14 0
You'll have to get out his car somewhere...
You'll have to get out his car somewhere...
Crossdresser Dare Dress
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