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Sissification -Art and Captions

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Created by
Damihorn
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prison sissy
prison sissy
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You knew before you put it on it was right xx :)
You knew before you put it on it was right xx :)
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Locked sissy pushed onto dildo
Locked sissy pushed onto dildo
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Awesome deepthroat photo featuring hot tranny
Awesome deepthroat photo featuring hot tranny
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tekuho
tekuho
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67 73 6
Hotwife trying to turn her husband in a sissy.
Hotwife trying to turn her husband in a sissy.
119 236 1
You may find it easier to get involved in Academy activities when you have friends who are there supporting you!
You may find it easier to get involved in Academy activities when you have friends who are there supporting you!
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Training
Training
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Lipstick is most importand
Lipstick is most importand
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Shoes
Shoes
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Lucky
Lucky
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Toilet fun
Toilet fun
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Brothers
Brothers
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Dress up!
Dress up!
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Smiling pegger
Smiling pegger
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232 472 8
Glasses
Glasses
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me
me
77 159 3
Crossdressing Is My Aphrodisiac
Crossdressing Is My Aphrodisiac
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3 10 0
Good gurl
Good gurl
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54 126 0
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70 115 2
74 126 1
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7 10 0
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77 208 3
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I would marry him
I would marry him
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30 39 0
14 15 1
Advertisement
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Bellhop
Bellhop
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Little sissy riding on the train
Little sissy riding on the train
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.ready for a garl with a dick?
.ready for a garl with a dick?
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Alba by personalami
Alba by personalami
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my little fantasy
my little fantasy
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Dress like a woman, get treated like a woman
Dress like a woman, get treated like a woman
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Art I can really appreciate.
Art I can really appreciate.
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Gang bang femboy lingerie
Gang bang femboy lingerie
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My first summer job was secret. But intoxicating.
My first summer job was secret. But intoxicating.
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Fuck me runnin'
Fuck me runnin'
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Tonite your on the bottom
Tonite your on the bottom
1 1 1
He makes a pretty gurl
He makes a pretty gurl
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Sissy porn star
Sissy porn star
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sissy
sissy
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Damn, I do love lingerie...
Damn, I do love lingerie...
22 27 2
Mistress will let you like it
Mistress will let you like it
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Daddies first Crossdresser...he loves it
Daddies first Crossdresser...he loves it
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Anna takes 2 for extra fun and money
Anna takes 2 for extra fun and money
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Mom teaching Georgie about anal training
Mom teaching Georgie about anal training
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The first time wearing lingerie is unforgivable
The first time wearing lingerie is unforgivable
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Surprise
Surprise
141 262 1
Pure bliss
Pure bliss
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Finding her purpose
Finding her purpose
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So you want to be a lady, I call your Uncle Kenny to let you feel his 10 inches.
So you want to be a lady, I call your Uncle Kenny to let you feel his 10 inches.
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Moms are great.
Moms are great.
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I got a headache..
I got a headache..
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Obedient sissy
Obedient sissy
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125 313 0
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120 205 3
You know what to do, sissy
You know what to do, sissy
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119 269 2
Sissy
Sissy
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gently and persistently
gently and persistently
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drawn pretty tranny
drawn pretty tranny
68 149 13
Repost
Repost
69 98 1
practice...
practice...
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63 103 1
sissy after-show party
sissy after-show party
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original drawn by blanclauz
original drawn by blanclauz
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The sissy liked being feminized by his mistress and the maid
The sissy liked being feminized by his mistress and the maid
48 89 1
Do it bitch!
Do it bitch!
39 98 1
Tekuho - Slutty Teens
Tekuho - Slutty Teens
153 339 12
sissy
sissy
257 592 6
Hot shemale
Hot shemale
14 22 0
67 176 1
sissy gangbang
sissy gangbang
19 29 1
Very true if given the opportunity
Very true if given the opportunity
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Hentai femboy #3
Hentai femboy #3
129 374 1
femboy
femboy
55 158 0