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prettysissygwen Profile prettysissygwen Profile views: 178268 Fanbase: 2201 About Me I am a lifelong sissy crossdressing masturbator. I adore shaving my legs and wearing pantyhose, stockings and very high heels with all kinds of skimpy little gurly outfits. I am a chronic sissy masterbator while dressed up. I love being a gurl, and hope to find another gurl to play dress up with! Interests ballet heels , cocksucking , crossdressers , cuckolding , femdom , feminization , french maid , high heels , humiliation , pantyhose , redheads , sissies , stockings , transvestites Signed up: 14 years and 12 months ago Images viewed: 109392 Images uploaded: 230 Gender: TS/TV Sexual orientation: Bisexual Birth: 10/03/1969 Location: United States Last Online: 3 days ago Connect with prettysissygwen Send Message Add Comment Become a fan Add to relations Status updates Comments (48) (See All Comments) SinthyaCD Comments: 306 Wrote on Jan 19, 2026 Thanks for becoming a fan   Opal_Moon Comments: 197 Commented on Dec 9, 2025 "Extremely suckable! I love this so much. So sexy!"   Opal_Moon Comments: 197 Commented on Dec 9, 2025 "Adorable!" prettysissygwen | Dec 10, 2025 Aww thank you!   KDMKDM Comments: 3,908 Commented on Dec 8, 2025 "Mmmmmm fuck yes call me you got my cock hard here in Vegas I want you"   KDMKDM Comments: 3,908 Commented on Dec 8, 2025 "Your cock looks so cute"   KDMKDM Comments: 3,908 Commented on Dec 8, 2025 "Mmmm hot"   mattcazzo Comments: 1,393 Commented on Oct 5, 2025 "this pretty sissy faggot loves to be on her knees sucking cock."   Danielle997 Comments: 6,625 Commented on Aug 28, 2025 "What a beautiful dress! "   ARRI35BL Comments: 90,643 Commented on May 18, 2025 "You take off your shoes, shoves one heel in my urethra and the other in my ass"   ARRI35BL Comments: 90,643 Commented on May 18, 2025 "Hmmm... I rub my cock on your thigh until I ejaculate and make you eat my cum collected on the nylon with my fingers calling you a dirty slut" prettysissygwen | May 19, 2025 I'd like that!   See All Comments | Add Comment

Galleries (1) (See All Galleries)   Pictures of Pretty Sissy Gwen   230     2012-10-18 02:15:46  Favorites (1014) (See All favorites)   Sexy small, soft, cut, cocks.....   57     2024-12-16 16:16:58    Cocks cuming    41     2025-12-06 04:19:56    Hayden Panettiere Wedding Dress/Cleavage   6     2025-08-31 01:57:10    CockBlock 2   6     2019-03-30 16:40:53    Sissy Poupette propre pour Maitresse   12     2025-11-09 01:54:05  Clubs (31) (See All clubs) Hot chubby tranny women NEPA Cross Dressers Voluptuous BBW & SSBBW ULTIMATE TV/ CD/ TS/ T-GIRL Community Sissy Captions Club Stocking mode Natural Redheads Girls that boys want to be LADY EWA Ballet Boots and Ballet Heels Bois become gurls Maids, French Maids, Sissy Maids MEN THAT LOVE TO DRESS UP AS SLUTS AND THE WOMEN WHO LOVE THEM WITH INTERACTIVE FORUM School Uniform Club Colorful Sissy Princess Clothes: Sissy, Frilly, and Feminine Fanbase (2201) (See All fans)

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