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    • Tranny Cock Cums Four Ways February 5, 2018
      The problem with a multi-orgasmic crossdresser is she just doesn't know how to stop! You'd think every now and then she could have the decency to only cum once in a set of photos, but noooo, there she goes again spunking on every surface within reach of her overgrown clitty. I called this set Cum Everywhere for a reason. 4 orgasms isn't quite […]
    • Crossdressing Princess in Kinky Cock and Ball Torture January 8, 2018
      Nothing but 5 ruined orgasams for this spoiled tranny princess! That's what happens to naughty gurls. Get ready for some super kinky CBT in this crossdressing video. I've spent all day with my clitty and balls wrapped up tight in plastic wrap and fresh ginger, punishing myself for having such a big clitty. But it keeps swelling and getting bigger n […]
    • Promiscuous Princess Punished for Flashing her Tranny Cock November 27, 2017
      Katie-Ann is the naughtiest princess in the whole land. Nothing the King and Queen do will keep her clitty from growing, and the bigger it gets, the bigger the trouble it gets Princess Katie in! Today I'm locked in my tower wearing my punishment panties to try and keep my clitty in check, but I can still feel it throbbing and growing. What are punishmen […]
    • Young Secretary Xdresser Services Office October 31, 2017
      Sexy secretary Katie-Ann offers desk side ball draining services, and looks like you're going to be her first client today! While wearing stockings and heels to the office every day seems to get me pretty far in life, it can be a little problematic when the boys spend more time staring at my long sexy legs than they do actually working. I mean, I realiz […]
    • Office Crossdresser Demands Performance October 22, 2017
      Sorry, Charlie, it's all business with this orgasm ;) There won't be any fun in this office as I strut in front of my desk in my sharp white stiletto heels, click, click, click across the wood floor. You see, I hear you have a bit of a performance problem, and I intend to fix it right here and now. I'm not one to sit behind my desk all day and […]
    • Xdresser Fucks Fruits and Vegetables August 5, 2017
      Crossdresser Katie fills her ass with bananas and learns about figging! I really had a hard time with this video. I was trying so hard to be cute and innocent while teaching you about fruits and veggies, but I was feeling ever so naughty! Hopefully you don't mind too much as I switch back and forth between my innocent bubbly teen voice and begging you t […]
    • Teen Crossdresser Veggie Insertion! July 17, 2017
      Katie-Ann sure knows how to get her fruits and vegetables! My newest ultra high def photos will show you how I stay so fit and sexy - I get plenty of fruits and veggies every day ;) Of course, each fruit or vegetable has it's own role to play in a balanced diet, and it's important to know what each one is good for! Today I'll be introducing ca […]
    • Xdresser's First Time July 6, 2017
      You didn't know your girlfriend was a tranny!? I know Katie-Ann's a cute little thing, but all the girls at school talk about how her clitty is longer than their boyfriends' cocks! I can't believe you didn't know until she asked you to go down on her. So, um... what was it like? Everyone's been wanting to hook up with her to see […]
    • Crossdresser Playing with Condom June 8, 2017
      Teen crossdresser learns about safe sex... sort of :) So, my parents aren't home and I was thinking... maybe today would be a good day to, you know, do it. I wore my thigh high toe socks for you today, I know how they drive you crazy ;) Oh, and I found these condoms in the girls locker room, I guess we should probably use them. C'mon, pull your pan […]
    • Extreme Xdressing CBT May 17, 2017
      Your crossdressing mistress just raided your wife's panty drawer! What're you going to do about it? Yup, that's right. I stole these wool tights from your wife, and took her knee-high boots too. I even made a little modification to her patterned tights to accomodate my panty bulge ;) You love me enough to let me keep them, don't you? I me […]

Sissy Maid Sucks Cock

  • Here’s a new one for you. Meet Karen, a transvestite slut who loves to turn her boyfriends into worthless little sissy slaves. Mistress Karen is standing over her new crossdressing french maid in this gallery, instructing her on how to suck cock. And conveniently, Karen has a nice hard cock for her new slut to [...]

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    Zoe Gets Her Cock Sucked

  • I love crossdresser Zoe’s name – Zoe Fuck Puppet – because it describes her personality perfectly. This gurl has to be the biggest slut I’ve ever seen! She has hardcore tranny sex in almost every one of her sets, and in her solo sets she still has a collection of huge toys that she fucks [...]

    • Filed under: Clothes, Gallery, Thigh Highs by admin
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