I’m just about to hit it big!


Everyone has dreams and fantasies about what they would do if the won the lottery, and this cross-dresser is no exception.  I just think my list of things to do would be a little different than most other people.

Sure, like most people, I would really like to tell my boss that I no longer would be coming to work anymore.  Not needing to worry about an income source has got to be one of the greatest feelings in the world.  I have heard of many people winning the lottery and it being a curse.  I don’t think that curse would apply to me, and I am more than willing to give this “instantly wealthy” thing a whirl!

It’s my fantasy, so I am going with the thought I just took home $300 million.  So I just quit my job and the next thing I am going to do is get my ears pierced.  Work was the main reason I have never done this, so now that I don’t have a job it is getting done.  Anyone else in my life who notices my newly pierced ears will now just think of me as one of those eccentric wealthy folk instead of just weird.  Anyway, no boss to tell me it’s unacceptable so it’s a done deal.

Sure, sure, there’s lots of shopping to do and closets to pack full of vintage treasures, but those are the obvious things.  Every cross-dresser with a 1950’s fascination would be doing those things.  But there a couple of things I would do when I become the newest multi-millionaire that would separate me from the masses…

…like buying a second house.  Nothing too special, but I want a house to become the biggest closet a closeted cross-dresser could have.  Somewhere out of the way and hidden from the world where I could go in as a guy, turn into Donna Reed or Doris Day, and spend some time with the other side of me.  I would not have to worry about family and friends showing up, because I would never tell them it existed. This house would have a good amount of land too, so I could wander outside and feel the wind on my legs for a change.  It would be Valerie’s palace away from the world.  That’d be great!

Another thing I thought about doing is starting my own company.  One where I would primarily hire cross-dressers and you could imagine what the dress code might look like.  The only problem is I have no idea what a bunch of CDs, all dressed up, could do as a business.  I need some ideas here.  Suggestions anyone??  We would probably be horrible at manufacturing anything, so that angle is out.  There has to be something we do better than any other group, I just haven’t put my finger on it yet.

I did think about resurrecting the old TWA, aka Trans World Airlines (catchy name, huh?)  Then I could get some fabulous vintage stewardess outfits and have a ball.  Maybe we could fly around and go shopping, but I’m not sure how that investment would make any money.  I would just spend myself back into the working stiff lifestyle.  This project is still under review.

I also thought about buying a bar/restaurant.  Making it a place where transgendered or anyone could go without feeling judged.  I would hire some insanely big and mean bouncer-type guys to keep the trouble makers out.  I would seriously overpay these guys so that they were more than motivated to take care of us like we were their little sisters.  In the end, I think this would just be another way to drain all the money and create some well manicured alcoholics.  Yeah, better ditch this idea.

This whole “what to do when I am obscenely rich” plan still needs a lot of work.  But I am making progress.  I have $3.00 to throw at the next lottery in hopes of striking it rich.  Wish me luck! (A girl can dream right?)



4 thoughts on “I’m just about to hit it big!

  1. Pingback: Uh oh… I don’t think we’re alone in here Val… | So Very Deep (In The Closet)

  2. Pingback: What you DONT see is what you get! | So Very Deep (In The Closet)

  3. Pingback: Wrapping up 2015; and looking forward… | So Very Deep (In The Closet)

Thoughts anyone??

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