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Conquering my Fears One Outfit at a Time

August 29, 2012
Pants – Guess
Black Top – Converse One Star
White and Black Striped Top – Guess
Shoes – New York Transit

I like the outfit pictured above, when it is cool enough for me to wear it.  It has been so dang hot lately and on this night I happened to be in Las Vegas.  At night, I think it got down to the low 90s.  But inside the casino, they had the air conditioner blowing hard and it was quite cool.  I decided to wear my favorite pants.

I like these pants, because they are very long and they make my legs look great.  Whenever I wear them, I have to wear a certain size heal for them to not drag on the floor as I walk.  The shoes I have on, are just barely tall enough to keep my pants off the ground.

With this outfit I also have one of my go to shirts on.  The black top is a very strategic garment for me.  First off, the arms are longer and they help to hide my larger arms.  Wearing a top like that helps me to feel more relaxed ass it is one less very obvious tell that I can cover up.  The other thing I like about this top is that it just barely covers my crotch.  This allows for me to not have to wear any special undergarments, or do anything special with Mr. Happy.  The shirt cover the barely noticeable extra bits in my pants.

This outfit made me feel very comfortable, which I was looking for as on this evening I decided to face another one of my fears.  It appears to me that if I have never done something before while dressed as a girl I have a notion that I can’t do it while dressed as a girl.

This particular evening I decided that I wanted to go down to the casino and play roulette.  My wife and I like to play for fun.  We gamble responsibly, for anyone that really cares.  But I have great fears when I choose to dress as a girl and put myself into new situations that I need to directly interact with the public.  I have had more than one person on this blog that has let me know that they think I get to do what I do in public as I can readily pass as a GG.  To me, nothing could be further from the truth.  Maybe I can pass, at a glance.  But a longer look allows anyone who cares to see, that I am clearly a guy dressed as a girl.  Besides, even if people can’t tell from my looks, they can certainly tell from my voice.

For me to go out, dressed as a girl, and interact directly with the public, such as a dealer and other players at a roulette table, was pretty intimidating before I did it.  The long and the short of it, is that it again, was no big deal.  I just went and did my thing, and it went just as good as it ever has.  And bummer for me, no dressing as a girl did not bring me any luck on this particular evening.  I broke evening while Jules lost about $100.

Love ya!

Face your fears!!

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