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prettysissygwen Profile prettysissygwen Profile views: 177763 Fanbase: 2191 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 8 months ago Images viewed: 109392 Images uploaded: 230 Gender: TS/TV Sexual orientation: Bisexual Birth: 10/03/1969 Location: United States Last Online: 6 hours ago Connect with prettysissygwen Send Message Add Comment Become a fan Add to relations Status updates Comments (47) (See All Comments) mattcazzo Comments: 1,263 Commented on Oct 5, 2025 "this pretty sissy faggot loves to be on her knees sucking cock."   Danielle997 Comments: 6,136 Commented on Aug 28, 2025 "What a beautiful dress! "   ARRI35BL Comments: 80,792 Commented on May 18, 2025 "You take off your shoes, shoves one heel in my urethra and the other in my ass"   ARRI35BL Comments: 80,792 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!   ARRI35BL Comments: 80,792 Commented on May 18, 2025 "To take with this outfit in a soundproof basement to film you during a gang bang with about ten very pervert and violent thugs. And perhaps you shall less smile. Whatever, the video will be sent to your whole family..."   steph_nylons Comments: 63 Commented on Mar 17, 2025 "This look is heaven"   loco1953 Comments: 1,859 Commented on Mar 11, 2025 "ouah quelle beauté sublime" prettysissygwen | Mar 11, 2025 merci   Sissy111012 Comments: 4,585 Wrote on Feb 23, 2025 Thank for being a fan. Love your gallery and your favorites. Horndog14 6 Jun, 2025 Hello dear,, thank you so much for becming a fan; it IS appreciated!   jackajerkin Comments: 1,024 Commented on Jan 17, 2025 "I would love to see a photograph of you seated like this with your mouth wide open. It would be a great tribute pose . . . ."   SissySopia Comments: 69 Commented on Dec 26, 2024 "❤️❤️❤️ A whole warehouse of outfits and high heels, nice! ❤️❤️❤️"   See All Comments | Add Comment

Galleries (1) (See All Galleries)   Pictures of Pretty Sissy Gwen   230     2012-10-18 02:15:46  Favorites (1009) (See All favorites)   Losers: Lucy's sissy life 01   16     2025-08-19 16:15:19    Sissy captions that speak to me 145   20     2025-10-06 23:22:25    Beta Loser 101 - Premature Ejaculator Training   14     2022-10-12 13:44:45    Sissification 101 - Clitty Control Guide   13     2022-09-22 15:23:14    About your SPH fetish   25     2021-07-03 13:25:31  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 (2191) (See All fans)

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