Transvestite halloween stories

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Halloween Misadventures

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My First Time Crossdressing WITH PICTURES - The Casey Blake

It was freshman year of high school and I was friends with a few girls and for Halloween, we all wanted to get together and do this little trick-or-treat night together. I had never gone out trick-or-treating on my own. Do it! DO IT! In preparation for that night, I asked one of my friends to do my makeup. She brought her makeup to school and we literally sat on the bench during lunch and she did my makeup in the middle of the Courtyard at my high school. Then I just loaded up a bag full of the clothes I was going to wear that night and the wig and whatnot.
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Transformed in to Halloween Ho: A crossdressing Halloween story

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Is this understandable? About 30 years ago when I was basically a less experienced crossdresser, I had the opportunity to do a costume exchange with my loving wife for a good friend's combination Halloween and birthday party. Going to a party en femme was exciting.
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Comments
  •   Dokinos April 4, 2021
    Like this one!
    +9 -4
  •   Faekora April 4, 2021
    Good luck convincing people to buy the whole thing when the short bit they see for free looks like shit.
    +20 -14
  •   Nikoshicage May 5, 2021
    sweet tune in the beginning!!
    +12 -1
  •   Douzshura February 2, 2021
    excelent animation wowTbh if I woke up to someone licking my hairy asshole I would laugh my ass off (no pun intended) and if it was a guy I would fart in his mouth lol if it was a girl I would go with it exatly examplecomment2 examplecomment1 Exactly.
    +24 -10
 
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