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Dad sissy date night went well
Dad sissy date night went well
Daddys Cock Daddys Sissy Sexy Sissy
1 6 6
Sissy is going on a date :D
Sissy is going on a date :D
Amateur Date Non Nude
26 75 1
Sissy thanking her date
Sissy thanking her date
Blowjob Oral Sissy
102 265 0
Better Play With His Cum On The First Date Sissy Caption
Better Play With His Cum On The First Date Sissy Caption
Blonde Cumplay Cumshots
74 246 2
Sissy Sayuri Matter getting ready for "her" date
Sissy Sayuri Matter getting ready for "her" date
Crossdresser Non Nude Panties
80 178 9
First Date BJ Sissy Caption
First Date BJ Sissy Caption
Brunette Cumshots Sissy Caption
3 8 1
Sissy slut waiting horny for the hung masculine date from grindr
Sissy slut waiting horny for the hung masculine date from grindr
Fem Legs Miniskirt
1 3 3
Sissy ready for date
Sissy ready for date
Amateur Lingerie Non Nude
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ideal date
ideal date
Femboy Sissy Trap
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32 74 2
Teasing Me Before Her Date
Teasing Me Before Her Date
Chastity Creampie Cuckold
9 43 0
You're beautiful and totally deserve the best, but she only wants to date real men. Sorry. :/
You're beautiful and totally deserve the best, but she only wants to date real men. Sorry. :/
Anal Babes Bottom
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sisst date
sisst date
Sissy
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Sissy_slut_90 in a beautiful dress and ready for the date
Sissy_slut_90 in a beautiful dress and ready for the date
Cage Caged Crossdresser
5 10 0
Outfit check selfie before going back to my date
Outfit check selfie before going back to my date
Crossdresser Dress Heels
3 11 2
You were dating my younger sister & I knew your reputation. You made a deal that if I took her place then you'd date me instead of her...
You were dating my younger sister & I knew your reputation. You made a deal that if I took her place then you'd date me instead of her...
Blonde Bully Crossdresser
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Date night
Date night
Sissy
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Date night
Date night
Crossdresser Sissy
1 4 0
Checking the angles pre-date
Checking the angles pre-date
Crossdresser Redhead Sissy
1 3 0
Play Date
Play Date
Panties Penis Sissy
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You'd made me dress up & go on a date with you. I felt you touch my bum & so I turned & smiled at you xx
You'd made me dress up & go on a date with you. I felt you touch my bum & so I turned & smiled at you xx
Brunette Bully Crossdresser
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Want a play date?????
Want a play date?????
Sissy Boi
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Want a play date?????
Want a play date?????
Sissy Boi
0 0 0
Want a play date?????
Want a play date?????
Sissy Boi
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Pegging Choices - 4,5,7 for me
Pegging Choices - 4,5,7 for me
Choice Date Pegging
8 13 0
Walk of shame
Walk of shame
Amateur Babes Brunette
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