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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    Femboy Furries 245    25   2025-10-01  Crossdressermi <1,721 fans>   Femboy Furries 244    24   2025-10-01  Crossdressermi <1,721 fans>   A Female Led Relationship ( FLR ) - Dominant Females    8   2025-10-01  FLR - Femdom Led Relationship blaeberry <149 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 <1,484 fans>   Locktober     21   2025-10-01  Locktober lecheur53 <600 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 <1,484 fans>   Sissy Whore 13    33   2025-10-01  Sissy Whore Sissy_Scarlett <1,656 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 <1,644 fans>   Ulrike Strandgurl    8   2025-10-01  cduli <5,617 fans>   Fancy and Ulrike    8   2025-10-01  cduli <5,617 fans>   Alexis2Night 2 (Tgirl/CD)    148   2025-10-01  Found on Twitter/X: Alexis2Night aliciat <10,723 fans>   Ashley Doll 2 (Tgirl/CD)    145   2025-10-01  Found on reddit: fat4larry aliciat <10,723 fans>   Embarrassed_Dig_5450 2 (Tgirl/CD)    143   2025-10-01  Found on reddit: Embarrassed_Dig_5450 aliciat <10,723 fans>   Lily_Stormagedon 5 (Tgirl/CD)    150   2025-10-01  Found on reddit: lily_stormagedon aliciat <10,723 fans>   Mature Gurls    95   2025-10-01  wankitoff <1,350 fans>   My dresses, tights and heels     17   2025-10-01  Emmygurl <280 fans>   Theres a Lump in my Pants    70   2025-10-01  dementer100 <3,887 fans>   Gurl on the Go    1   2025-10-01  Ginger_Snapp69 <269 fans>   Sissy Deanna - New England Sissy Locked    34   2025-10-01  Please expose me I’m in the closet trapqueen69 <1,611 fans>   Clothes I'd like to wear - Lingerie Edition    48   2025-10-01  This is a view of the type of clothes that I'd love to try on and wear. I'm a big fan of the lingerie of the 80's and think these little items were so feminine and sexy, I can't explain why they ever fell out of style but I still love them. For a... krista024 <3,078 fans>   Good wanking here     100   2025-10-01  Matuer2me <360 fans>   Playing in found clothes     51   2025-10-01  Luvtwocum1 <1,693 fans>   Old b/w Pictures Colorised test - let me know your favourite    5   2025-10-01  Kimnylons <1,208 fans>   Charlie Sweetie purple lingerie [Charliesweetie]    20   2025-10-01  More like a lilac or lavender color, but you get the idea. It's definitely one of my favorite things to wear. The color looks so lovely and design makes me feel super feminine. If you enjoy wearing lingerie you should totally try all types of... charlie_sweeti <188 fans> :: prev :: | 1 | ... | 220 | 221 | 222 | 223 | 224 | 225 | 226 | 227 | 228 | 229 | :: next ::