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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    Ideal Undies to Share    42   2024-04-23  _Tights_ <12 fans>   Cocu cocufieuse train�e candauliste pawg milf cuck grosse truie    12   2024-04-22  Colibrix <772 fans>   Some Sissy Faggot Housewife Photos    7   2024-04-15  tamis_demise <36 fans>   Vintage Transvestite Shemale 3    91   2024-02-24  Kristin_crossd <3,487 fans>   BBW Cocu cocufieuse train�e candau CD Crossdress    19   2023-12-24  Colibrix <772 fans>   Gina C - A Transvestite Through The Decades    96   2023-12-14  My wife took a few pics early on but the rest of the vintage ones were taken by me with a 35mm camera, tripod and self timer (or a polaroid). I was (and still am) quite slim and could slip into my wife's size 12 clothes (or anyone elses given the... Gina_Campbell <11 fans>   Nov 23 Retro and polaroids bottomless in bras or lingerie    259   2023-12-01  All of the galleries I post are hand pick images selected from galleries previously posted at Imagefap. Many thanks to the original posters!!! Madposter666 <3,602 fans>   Caroline is back !    14   2023-08-07  Hello, I'm back again ! I hope you're fine with my new Pics! Baisers from France ! CarolineCherie <1,050 fans>   Beatiful Darla    28   2023-08-01  Darla Bond, a beautiful vintage crossdresser model....she loved to be tied up Troietta1997 <80 fans>   Klassische Miederbuestenhalter fuer Sissys    4   2023-07-14  Eine brave Sissy traegt auch die "richtigen" Buestenhalter Alf007ab <156 fans>   Vintage TVs Shemales and Crossdressers    163   2023-07-04  A Selection of Vintage pics of Crossdressers, CD's, Shemales, He-She's. stmagaretsman <2,793 fans>   60s lingerie ads 6    27   2023-02-21  nylonslipjes <1,123 fans>   KATX 466 - Stays and Gloves - Centurian Catalog    7   2023-01-14  ObyJuanKenobi <1,801 fans>   NM 012 - Transvestite Marriage 2 - 5 - Unknown artist    12   2022-12-31  Found No. 5, but alas still no number 1... ObyJuanKenobi <1,801 fans>   forced femme    26   2022-12-02  sheep791 <133 fans>   men in panties 1.0    24   2022-11-24  bisomebody <65 fans>   Pin up Drag Queens and Tgurls I adore    34   2022-11-14  Suzzane22 <396 fans>   DeniseTS Nikita-nylon    21   2022-08-20  cduli <4,986 fans>   Anal sex 96    104   2022-08-19  myfavos <760 fans>   corset bustier    45   2022-07-12  I wear some of these ... i owned some! I wish i can wear all it been tied up and fuck in each one of these corset...I will add some detail how i wish to wear them or/and who the owner of the lingerie plz comment your horny though lifeguardsissy <333 fans>   teddiette and teddy    13   2022-07-12  I bought some of those..n I wish i can have it all I will add some detail how i wish to wear them or/and who the owner of the lingerie plz comment your horny thought lifeguardsissy <333 fans>   Retro searching    1   2022-06-21  cduli <4,986 fans>   Buffy e Karen Dior    141   2022-04-28  Dannibun <561 fans>   A rummage through Chiffon's archive 8    28   2022-04-14  chiffontv <93 fans>   A rummage through Chiffon's archive 7    49   2022-04-14  chiffontv <93 fans> 1 | 2 | 3 | 4 | 5 | :: next ::