Share this picture
HTML
Forum
IM
Recommend this picture to your friends:
ImageFap usernames, separated by a comma:



Your name or username:
Your e-mail:
  • Enter Code:
  • Sending your request...

    T'nAflix network :
    ImageFap.com
    I Love DATA
    You are not signed in
    Home| Categories| Galleries| Videos| Random | Blogs| Members| Clubs| Forum| Upload | Live Sex


    prettysissygwen's profile

    prettysissygwen Profile
    prettysissygwen
    Profile views: 177058
    Fanbase: 2180

    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 4 months ago
    Images viewed: 109392
    Images uploaded: 230

    Gender: TS/TV
    Sexual orientation: Bisexual

    Birth: 10/03/1969

    Location: United States

    Last Online: 23 hours ago

    Connect with prettysissygwen
    Status updates


    Comments (47) (See All Comments)
    ARRI35BL
    ARRI35BL's profile
    Comments: 71,643
    Commented on May 18, 2025
    "You take off your shoes, shoves one heel in my urethra and the other in my ass"
     
    ARRI35BL
    ARRI35BL's profile
    Comments: 71,643
    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!

     
    ARRI35BL
    ARRI35BL's profile
    Comments: 71,643
    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
    steph_nylons's profile
    Comments: 59
    Commented on Mar 17, 2025
    "This look is heaven"
     
    loco1953
    loco1953's profile
    Comments: 1,800
    Commented on Mar 11, 2025
    "ouah quelle beauté sublime"
    prettysissygwen | Mar 11, 2025
    merci

     
    Sissy111012
    Sissy111012's profile
    Comments: 4,729
    Wrote on Feb 23, 2025
    Thank for being a fan. Love your gallery and your favorites.
    Horndog14's profile
    Horndog14 6 Jun, 2025
    Hello dear,, thank you so much for becming a fan; it IS appreciated!

     
    jackajerkin
    jackajerkin's profile
    Comments: 873
    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
    SissySopia's profile
    Comments: 61
    Commented on Dec 26, 2024
    "❤️❤️❤️ A whole warehouse of outfits and high heels, nice! ❤️❤️❤️"
     
    3406
    3406's profile
    Comments: 685
    Commented on Nov 23, 2024
    "Wow,I knew you had something else to show,it would be sexy and hot if he was inside your panty hose pulled up and it curled up resting,super hot honey and very passable for a very hot sexy lady!!😋😋😍😍😍😍"
    prettysissygwen | Nov 26, 2024
    Thank you so much! Wish you see it in person

    3406 | Nov 26, 2024
    Me to,it looks sexy and likable and suckable!🥰🥰

    big-ME | Jul 2, 2025
    definitely need to see more of this ..too many pics but only one of this the best part in my view

     
    Tgeef16
    Tgeef16's profile
    Comments: 10,510
    Commented on Oct 31, 2024
    "I knew there had to be something equally as gorgeous at the top of those legs"
    prettysissygwen | Oct 31, 2024
    : )

     
    Galleries (1) (See All Galleries)

      Pictures of Pretty Sissy Gwen 
     230 
     
     2012-10-18 02:15:46 
                  

    Favorites (993) (See All favorites)

      Redheads clothed but sexy 
     263 
     
     2025-07-01 18:40:12 
                  
      Ultimate Sissy Captions Collection - Part 1 
     1000 
     
     2021-05-22 16:38:36 
                  
      Amber CD 
     97 
     
     2025-04-08 17:05:35 
                  
      Captioned gifs to cum by 2025033117 
     10 
     
     2025-03-31 16:06:44 
                  
      BREASTLESS BARBIE BOIS 
     43 
     
     2016-03-29 20:50:50 
                  

    Clubs (31) (See All clubs)


    Edit comment:



    Contact us - FAQ - ASACP - DMCA - Privacy Policy - Terms of Service - 2257



    Served by site-686bfb45f8-zmvtg
    Generated 02:37:59