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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 Masturbation 2    1   2025-08-20  Ginger_Snapp69 <268 fans>   Lana a 76 years old sissy cumslut whore!    40   2025-08-20  Lananew <1,689 fans>   Izzy Winterz 4 (Tgirl/CD)    152   2025-08-20  Found on reddit: IzzyWinterz aliciat <10,707 fans>   Sophia Angelova 2 (Tgirl/CD)    101   2025-08-20  aliciat <10,707 fans>   Satella209 3 (Tgirl/CD)    141   2025-08-20  Found on reddit: Satella209 aliciat <10,707 fans>   Carrotcakearot (Miley) 4 (Tgirl/CD)    169   2025-08-20  Found on reddit: Carrotcakearot aliciat <10,707 fans>   home alone 126    11   2025-08-20  nilonboi <721 fans>   Femboy Toons 852    24   2025-08-20  Crossdressermi <1,697 fans>   Outdoor 20.08.2025    18   2025-08-20  sweethome11 <792 fans>   Femboy Toons 851    24   2025-08-20  Crossdressermi <1,697 fans>   Assfucking Femboys &amp; Crossdresser 142    24   2025-08-20  Crossdressermi <1,697 fans>   White Pantyhose Sissy Fag Diana    7   2025-08-20  Sissy panty-fag Diana ran to BrasNThings as instructed to buy a pair of ridiculous white pantyhose to rub her little sissy penis through. The sales lady laughed at sissy when he tried to convince her that the pantyhose was for his wife. LoL!! Like this... The_Sissy_Hunt <1,685 fans>   Alpha-Ass-Apphire    13   2025-08-20  sissyhoon <2,376 fans>   Faldita 2    10   2025-08-20  pelotasatadas <2,359 fans>   Undercover    3   2025-08-20  sissyhoon <2,376 fans>   My Sissy Life    2   2025-08-20  Subcd101 <4 fans>   Femboy Toons 850    24   2025-08-19  Crossdressermi <1,697 fans>   Femboy Toons 849    24   2025-08-19  Crossdressermi <1,697 fans>   Femboy Furries 207    32   2025-08-19  Crossdressermi <1,697 fans>   Femboy Toons 848    24   2025-08-19  Crossdressermi <1,697 fans>   A Black And White Serie    13   2025-08-19  My wife had fun with her new photo app. bastop <271 fans>   Sissy     29   2025-08-19  SissySashaExpo <305 fans>   A couple of new ones     9   2025-08-19  CyclingCD <218 fans>   Sissy has a new Oktoberfest outfit    3   2025-08-19  I got this and I have to say I like the outfit and the colors. Sissyfaggot88 <400 fans>   Completely naked sissy has a new chastity device    3   2025-08-19  I'm completely naked with my new chastity device because the previous one was too big. My friend bought it for me and she likes to have me in chastity so there's a risk that she sometimes keeps the keys. It's quite nice and small, not visible with... Sissyfaggot88 <400 fans> :: prev :: | 1 | ... | 281 | 282 | 283 | 284 | 285 | 286 | 287 | 288 | 289 | 290 | :: next ::