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Free Crossdressing porn pictures 10 25 50 100 150 results per page   Search in this niche: Filter by: Any size Small Medium Large Huge Anytime Today This week This month  Gallery Name   Images   Quality   Added    Sissy Chastity Captions 13    50   2025-10-02  Bloodrise69 <4,923 fans>   Aline Travestie (818)    20   2025-10-02  Aline travestie en lingerie aline_trav <1,488 fans>   Cum Lovers     24   2025-10-02  stillnness <33 fans>   Me    6   2025-10-02  Kalista007 <17 fans>   Exposing Sissy    3   2025-10-02  SissyLiv93 <4 fans>   Crossdresser 1    17   2025-10-01  Some more of me from earlier this year. CheshireCatCD <359 fans>   cute slim blonde goth femboy feet young CD / TV teen    6   2025-10-01  pinktwink <77 fans>   Femboy Toons 1097    24   2025-10-01  Crossdressermi <1,699 fans>   Femboy Toons 1096    24   2025-10-01  Crossdressermi <1,699 fans>   Femboy Toons 1095    24   2025-10-01  Crossdressermi <1,699 fans>   Femboy Toons 1094    24   2025-10-01  Crossdressermi <1,699 fans>   Femboy Toons 1093    24   2025-10-01  Crossdressermi <1,699 fans>   Sissy captions that speak to me 144 - SPH repost 3    20   2025-10-01  Slinky_Gurl <3,243 fans>   Femboy Toons 1092    24   2025-10-01  Crossdressermi <1,699 fans>   Femboy Toons 1091    24   2025-10-01  Crossdressermi <1,699 fans>   Assfucking Femboys &amp; Crossdresser 146    24   2025-10-01  Crossdressermi <1,699 fans>   Femboy Furries 245    25   2025-10-01  Crossdressermi <1,699 fans>   Femboy Furries 244    24   2025-10-01  Crossdressermi <1,699 fans>   A Female Led Relationship ( FLR ) - Dominant Females    8   2025-10-01  FLR - Femdom Led Relationship blaeberry <139 fans>   My boi/sissy ass for breeding and comments/captions    19   2025-10-01  Hi, I am a sissy faggot and this is my ass pussy. Please look at it, as I spread and fuck it and get hard/wet. Please leave a comment. Love captions, love tributes. Willing to swap captions/comments/anything!nSome pics are screencaps from videos of mine. cuckfeetlover <1,481 fans>   Locktober     21   2025-10-01  Locktober lecheur53 <596 fans>   Crossdressing for cock. Come fuck me!    21   2025-10-01  JJSissy <645 fans>   Small penis boy/cd - Please humiliate/caption me.    17   2025-10-01  My little tiny penis for you to comment, on, tribute, caption, please humiliate me.Make me feel like the limp fag sissy I am. I belong in chastity and my llimp clitty is useless.Tell me what I'm good for.nComment my stuff and I'll return the favour!n cuckfeetlover <1,481 fans>   Sissy Whore 13    33   2025-10-01  Sissy Whore Sissy_Scarlett <1,651 fans>   Exposed - nice and naughty at once. The Brave Edition     25   2025-10-01  Sissy Magazine Covers of: Alexa, Bella, Bethany, Chloe, Danielle, Devina, Hailey, Jade, Jamie Lynn, Janine, Jeje, Jenny Kane, Josephine, Julie (JulieLegs3), Kate, Kay, Lisa, Mine (Mine Tangent), Nicky, Pam (Pamela Rico), Rhianna, Samy, Sara, Tiffany, Tina Sissylover1981 <1,641 fans> :: prev :: | 1 | ... | 208 | 209 | 210 | 211 | 212 | 213 | 214 | 215 | 216 | 217 | :: next ::