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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 Andrea bei Ihrem Herrn    10   2025-07-05  SissyAndreaStg <147 fans>   Sissy Magazine Covers featuring Sammy. Made by Sweet Chloe    4   2025-07-05  These Covers were made by by Sweet Chloe. Link to Chloes profile: www.imagefap.com/profile/SweetChloe. Sissylover1981 <1,645 fans>   Couples in Need of Luv    44   2025-07-05  Bend over and ready to submit either ass or pussy. JimmyHardOn-54 <107 fans>   granny white panties    18   2025-07-05  Milka's white cotton panties are filled with my hot sperm. When she puts them on, her pussy will feel my hot sperm. Her hairy pussy will roll around in my sperm in her panties. I can't wait for her to take off her panties so I can smell them because... 5691za <1,518 fans>   Sissy Cumslut Captions 45    50   2025-07-05  Bloodrise69 <4,923 fans>   Femboy Toons 658    24   2025-07-05  Crossdressermi <1,719 fans>   me encanta sentir mis tangas en mi culito    13   2025-07-05  angelik <208 fans>   me siento mas putita con mi lenceria blanca    10   2025-07-04  angelik <208 fans>   Sexy babe    3   2025-07-04  Sexy babe Wonderwoman200 <708 fans>   Sexy babe    2   2025-07-04  Sexy babe Wonderwoman200 <708 fans>   cigar crossdresser sissy shemale kelly coxx Aberdeen    10   2025-07-04  sissykellycoxx <739 fans>   Leonies hot lingery 38    12   2025-07-04  Leonie01 <231 fans>   Wifes NYLON making me SO HARD    5   2025-07-04  Ivanderk777 <153 fans>   Sissy Bondage    278   2025-07-04  Ich mag es wenn ich überwältigt und dominiert werde, ich liebe es dabei in Badeanzügen und Leggings gefesselt zu werden.Ich lasse mich auch gerne mit reichlich Lotion einschmieren, und ich mache fast alles wenn ich hilflos gefesselt bin.Gerne... Samantha_Fesse <988 fans>   Pantyhose+Cock=SEXY    3   2025-07-04  Ivanderk777 <153 fans>   Be Attentive    24   2025-07-04  That_Feminine_ <1,256 fans>   Giganto macromastia Sissysick     31   2025-07-04  Sissysick got a new breast plate, giganto macromastia boobs, still working the bugs out of my massive boobs. This my first try and time to be a giganto huge boobs. Sissysick promise better pics to come. And where in the heck is Sissysick going to find... Sissysick <413 fans>   Something To Wear    24   2025-07-04  That_Feminine_ <1,256 fans>   The next door trap    49   2025-07-04  She loves to dress up in pretty things and take selfies. gus_lorenz <7,466 fans>   Sissysick pretty in pink 2    22   2025-07-04  Sissysick was so excited to wear my new outfit today. My cock was a dripping hot mess. Sissysick leaking all in my granny panties just made it worse. Hope my fat dick pleases my fans .feeling super sexy right now Sissysick <413 fans>   smooth clean and horny    49   2025-07-04  She's mad about the cock. Can't help herself. gus_lorenz <7,466 fans>   Beautiful cocks    20   2025-07-04  Joy_Hole <224 fans>   Sissysick pretty in pink     20   2025-07-04  Sissysick has put in the work at the shipyard and was able to buy my first outfit. So love my new heels and knee high socks with bows they my first pair the purple flowers are so pretty. Really glad everything fit . Sissysick was so excited and a new... Sissysick <413 fans>   Satyn crossdressing femdom art    13   2025-07-04  Satyn tends to draw men being caught wearing women's clothing or being made to take part in sexual activity with other sissies, but there are a small number of works that lend themselves to femdom (and others that have been edited by me so that they do). robertmugabe <941 fans>   Rainbow one piece    74   2025-07-04  windabird <143 fans> :: prev :: | 1 | ... | 377 | 378 | 379 | 380 | 381 | 382 | 383 | 384 | 385 | 386 | :: next ::