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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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197 547 0
Awesome deepthroat photo featuring hot tranny
Awesome deepthroat photo featuring hot tranny
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tekuho
tekuho
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69 75 6
Hotwife trying to turn her husband in a sissy.
Hotwife trying to turn her husband in a sissy.
123 240 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
62 145 1
Brothers
Brothers
75 150 4
Dress up!
Dress up!
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Smiling pegger
Smiling pegger
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238 481 9
Glasses
Glasses
119 260 2
me
me
79 160 3
Crossdressing Is My Aphrodisiac
Crossdressing Is My Aphrodisiac
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4 11 0
Good gurl
Good gurl
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54 126 0
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70 114 2
74 126 1
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7 10 0
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78 212 3
51 96 0
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I would marry him
I would marry him
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30 39 0
14 15 2
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
4 6 1
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
143 265 1
Pure bliss
Pure bliss
125 275 1
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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127 315 0
31 65 1
121 212 3
You know what to do, sissy
You know what to do, sissy
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120 276 2
Sissy
Sissy
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gently and persistently
gently and persistently
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drawn pretty tranny
drawn pretty tranny
69 150 13
Repost
Repost
72 104 2
practice...
practice...
211 438 4
66 108 1
sissy after-show party
sissy after-show party
74 117 3
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
54 92 1
Do it bitch!
Do it bitch!
39 98 1
Tekuho - Slutty Teens
Tekuho - Slutty Teens
161 345 13
sissy
sissy
259 595 6
Hot shemale
Hot shemale
14 22 0
68 176 1
sissy gangbang
sissy gangbang
19 30 1
Very true if given the opportunity
Very true if given the opportunity
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Hentai femboy #3
Hentai femboy #3
136 380 1
femboy
femboy
55 160 0