If I Won the Lottery

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August 25, 2015 by jessxdress


I bought a lottery ticket this morning while I am sure I won’t win I am also sure everyone has wondered what they would do if they won the lottery.  Quit our jobs, travel, or give some to family are common but what about those of us who cross the gender lines?  When you are so rich that you never need to work another day in your life what others think of you is suddenly less important and you could get away with breaking every taboo that has existed.  We would be able to wear womens’s clothing and if people don’t like it not really our problem.  So a list of things I have thought about if I won the lottery in regards to crossdressing.

  • I would have the best wardrobe ever. All the panties, bras, and dresses a boy could want
  • Finally a closet that can fit both wardrobes
  • I would buy a house somewhere just outside a city where I could sit on my deck in a bikini and read a book while sipping scotch.  Or maybe a cabin
  • I could get breasts, not sure if I would but I could
  • Custom made shoes so they would finally fit right
  • Trips across North America and Europe with a focus on crossdresser hangouts could be fun
  • I could wear whatever I wanted whenever

The joy of course would be being free to explore and push the limits of crossdressing, along with being rich enough to do whatever the hell else I wanted to do.  That is the joy of a $5 lottery ticket you get a few simple what if dreams even though you are likely to never win.

Anything you would do Crossdresser specific if you won the Lottery?

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