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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    Fill me!    1   2025-10-05  SissyJin <214 fans>   Naughty Maid    5   2025-10-05  Sissy_Michele <176 fans>   Just some of me    5   2025-10-05  PennyFrost <503 fans>   Sexy blonde cleaning the     15   2025-10-05  Amateur Crossdresser Blonde Pantyhose Sexy n1waldi <1,320 fans>   guys in hose 82    71   2025-10-05  Kristin_crossd <4,078 fans>   Sissy captions that speak to me 144 - more hypno, pills &amp; ma    20   2025-10-05  Slinky_Gurl <3,243 fans>   Every sissy wants to be a maid    20   2025-10-05  Slinky_Gurl <3,243 fans>   New Pink PVC Dress    40   2025-10-05  SissyDee65 <669 fans>   Colorful panties    29   2025-10-05  Maker-of-wood <889 fans>   CD Cock and Ass 38    18   2025-10-05  davers501xx <733 fans>   50 's Lingerie    18   2025-10-05  davers501xx <733 fans>   I See You're Wearing Heels     74   2025-10-05  wankitoff <1,340 fans>   Cocksucking Crossdressers (4)    85   2025-10-05  Matcdluverz <1,966 fans>   I love wearing this fishnet with this mini skirt.    7   2025-10-05  ELSA53 <3,051 fans>   2025 sissymaster2022 2. Task CHAINS &amp; STEEL for FUCKMEAT    24   2025-10-05  Task from my master sissymaster2022.nTo cuff myself with all my cuffs and chains, use my biggest ball gag, wear only pantyhose, plug and blindfold and take pictures (Comment: The first time I've ever jerked off to photos of myself...) SUCCUBUSSUB <176 fans>   2025 Sissy at WORK - THEFORBIDDENMAN    16   2025-10-05  Task for master THEFORBIDDENMAN SUCCUBUSSUB <176 fans>   Femboy Toons 1117    24   2025-10-05  Crossdressermi <1,697 fans>   A Little Taste Of Blacker666    24   2025-10-05  Jarritos <10,678 fans>   Femboy Toons 1116    24   2025-10-05  Crossdressermi <1,697 fans>   Femboy Toons 1115    24   2025-10-05  Crossdressermi <1,697 fans>   Femboy Toons 1114    24   2025-10-05  Crossdressermi <1,697 fans>   Femboy Toons 1113    24   2025-10-05  Crossdressermi <1,697 fans>   Femboy Toons 1112    24   2025-10-05  Crossdressermi <1,697 fans>   lingerie 14    35   2025-10-05  pampomme <15 fans>   ALEXA FONTENELLE SMITH / MILF CROSSDRESSER     9   2025-10-05  What is there to say? I enjoy dressing up and turning into a girl. I also enjoy a bit of WAM, so if anyone's into that, let me know :)nn nYour comments are always very welcome - I prefer them to people mass-liking my pics, which is a bit creepy tbh.nn... Alexa-Jane9 <19 fans> :: prev :: | 1 | ... | 201 | 202 | 203 | 204 | 205 | 206 | 207 | 208 | 209 | 210 | :: next ::