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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 Paula 7    5   2025-06-18  subsluthelen <35 fans>   Chantellesissy - getting photographed before use outdoors    5   2025-06-18  Pictures taken before I got fucked outdoors at a deserted quarry and in the woods subsissyfaggot <1,407 fans>   Caged Sissy Dana shows herself    10   2025-06-18  "Caged Sissy" is how I identify. My Sissy name is "Dana". DanaGently <92 fans>   new pantyhose from sh*in, so glossy so silky!    28   2025-06-18  Bought new pantyhose from china. Could be the best Ive ever tried on! hose_dude <295 fans>   T-Girl Barbie Boi    43   2025-06-18  tiedlegs <4,540 fans>   Osbouryn (Alex) 1 (Tgirl/CD)    161   2025-06-18  Found on reddit: Osbouryn aliciat <10,721 fans>   renEmily97 1 (Tgirl/CD)    140   2025-06-18  aliciat <10,721 fans>   Why Not Evelyn (Tgirl/CD)    137   2025-06-18  aliciat <10,721 fans>   Alexandria the Princess (Tgirl/CD)    74   2025-06-18  aliciat <10,721 fans>   Guynard femdom crossdressing art    4   2025-06-18  robertmugabe <941 fans>   Spread them legs    25   2025-06-18  SissySashaExpo <305 fans>   Tom Poulton femdom crossdressing art    27   2025-06-18  From Wilkipedia:Thomas Poulton (1897-1963) was a British magazine and medical illustrator who provided artwork for a range of publications including the British Journal of Surgery and the Radio Times. After his death it was discovered that he had also... robertmugabe <941 fans>   Recognize this sissy?    7   2025-06-18  Proveitorlosei <6 fans>   Toon slut can't get enough cock    25   2025-06-18  CSspecialist <195 fans>   Laurent LeBeau femdom crossdressing art    10   2025-06-18  robertmugabe <941 fans>   Gilbert AKA Eneg AKA Gene Bilbrew femdom crossdressing art    90   2025-06-18  robertmugabe <941 fans>   Prissy and Prim femdom crossdressing art    89   2025-06-18  Femdom art by Prissy and Prim, whose work is thematically identical. This collection excludes the forced-bi cartoons. robertmugabe <941 fans>   UK Sissy Charlotte    53   2025-06-18  She has a profile here, as well as on Erome. I think she's just darling . . . and SO fucking hot!! marvint1963 <3,978 fans>   Femboy Toons 620    24   2025-06-18  Crossdressermi <1,721 fans>   Whiteboi sissy for blacks bulls    16   2025-06-18  Bitch119 <855 fans>   Gagged     28   2025-06-18  Keep them quiet sissymaster202 <895 fans>   Ultra Gloss Blue Stockings    1   2025-06-18  EmmaWard49 <51 fans>   sissyin forest 2    18   2025-06-18  nacktsklave <2,385 fans>   Sissy faggot 50s Housewife    12   2025-06-18  Another sissy faggot aspiring to be taken, trained and owned as a 50s TV Housewife/slave to a Master tamis_demise <157 fans>   Naked and Exposed Sissy Faggot    1   2025-06-18  Just another naked and exposed sissy faggot. Never thought I would ever post this for public consumption, but here we are. tamis_demise <157 fans> :: prev :: | 1 | ... | 404 | 405 | 406 | 407 | 408 | 409 | 410 | 411 | 412 | 413 | :: next ::