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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    Mature sissy maid Nina ready for use    22   2025-08-16  Me as mature sissy maid. I am not the best maid, but i am very cheap. My payment is just to use any of my holes at least 3 times. And i am sure my work will improve, with the right spanking and discipline. I can also serve as a urinal, and for cleaning... Nina_SubSlut <215 fans>   Bridez 7    129   2025-08-16  YesPleaseMadam <1,662 fans>   Mature Sissy Slave Nina 2    44   2025-08-16  Again, me showing my mature sissy body, and my sissy activities. I am such a slut, and should be treated accordingly. I would love to serve a real man.I would love any comments, both sexy and humilliating, if you in any way feel i deserve them Nina_SubSlut <215 fans>   Slutty Sissy Red Sweater, Matching Panties, and Chastity    17   2025-08-16  Working up to cumming in chastisty newsissy69 <407 fans>   Contrasting moods....    10   2025-08-16  Emmygurl <279 fans>   Where are all the nice girls/gurls?    6   2025-08-16  Lananew <1,690 fans>   Joy Lee - Caged Summer    12   2025-08-16  Joy Lee in red and caged JoyLee <1,284 fans>   Mature sissy slave Nina 1    46   2025-08-16  Me showing of my mature sissy body. I am very submissive, and would love for a real man to use me as the cum hungry slut that i am. I need to be dominated and filled with cum and piss.Im sorry my camera is not better, i hope to take better pictures... Nina_SubSlut <215 fans>   Pink Pill Captions    40   2025-08-16  If we could, we would right......even just for a few hours, or days? filthyp <960 fans>   Super Sexy CD Kayla    107   2025-08-16  Fatsquidzilla <2,347 fans>   Sissy Cuckold Caption Confessions: &ldquo;I Thought I Was Enough    15   2025-08-16  Mistressmadeli <30 fans>   Beautiful Mature CD Patty    45   2025-08-16  Fatsquidzilla <2,347 fans>   Marvelous CD Tara    22   2025-08-16  Fatsquidzilla <2,347 fans>   Delicious CD Erin    35   2025-08-16  Fatsquidzilla <2,347 fans>   Helpless naked sissy in chastity and tied hands outdoors    1   2025-08-16  My friend who is much stronger than I am locked my hands behind my back, dressed me like a sissy whore and took me out into the garden where I had to walk around, she hoped the neighbor would see me like this or come over and talk to us Sissyfaggot88 <400 fans>   Stunning CD Kira    14   2025-08-16  Fatsquidzilla <2,347 fans>   Sissy shows off what he wears when he's at home    5   2025-08-16  Sissy shows off what he wears when he's at home Sissyfaggot88 <400 fans>   Beautiful CD Miela    109   2025-08-16  Fatsquidzilla <2,347 fans>   Fantastic CD Dani    24   2025-08-16  Fatsquidzilla <2,347 fans>   Panties last week    21   2025-08-16  Maker-of-wood <888 fans>   A real sissy wears dresses at home    11   2025-08-16  It's much more comfortable to wear a dress compared to pants, if you add fishnet stockings and black high heels it feels really good. Sissyfaggot88 <400 fans>   Sissy loves sunbathing in his new bikini    7   2025-08-16  My new bikini I got as a gift from a friend, she wanted me to try it out in the garden. Sissyfaggot88 <400 fans>   Sissy captions that speak to me 128    20   2025-08-16  Slinky_Gurl <3,237 fans>   Sissy exposure    1   2025-08-16  When you save my sissy photos, I lose all control! Then when you post them, I as sissy can never delete them. Permanent exposure. cindy_cross39 <1,702 fans>   Gurls That Wear Glasses    16   2025-08-16  The_Sissy_Hunt <1,685 fans> :: prev :: | 1 | ... | 289 | 290 | 291 | 292 | 293 | 294 | 295 | 296 | 297 | 298 | :: next ::