Adventures in Dressing to Affirm My Gender Identity

Before I transitioned, the only relief from my gender dysphoria was when I dressed to affirm my gender identity which in my opinion sounds much better than crossdressing.  When the world sees you as a boy and you are dressing like a girl, there are embarrasing situations that arise.  I thought it might be fun to take a look at my most embarrassing  top five adventures with dressing to affirm my gender identity.

5I had been dressed earlier in the day and it was the afternoon when I met up with a friend to hang out.  This was a rarity for me as I never really had a lot of friends so I tried my best to hold onto the few that didn’t instantly hate me.  Well, I was about to weird another one out as apparently I was not very thorough in removing my eye shadow and he noticed it and began to question me on it.  I made up a horrible excuse about a finger painting accident.  He seemed to buy it at the time but we never hung out again so I am pretty sure he figured out enough.

4I was walking along the road well after midnight and I was wearing a bra under my jacket with a pair of water balloons to simulate big boobs.  Seriously, I should have been okay.  However, along comes my neighbor and pulls over to give me a ride.  There was no way out and I had to do my best to scrunch up my jacket to hide the boobs.  I have no idea if I pulled it off but he didn’t say anything and I managed to escape quickly to my apartment once he dropped me off.

3Painting my toenails in the summer was always a bad idea but that didn’t always stop me.  On one occasion, I had my toenails bright red and I was walking with a different friend when we came upon a lake.  He decided that we should go wading along the shore to cool down.  It was really hot and this was a great idea other than the fact that my toenails were all pretty.  I decided to chance a huge silly lie and told him I would do it but had to explain my toenails first.  I said I was doing it for a science fair experiment so that I could map the speed of toenail growth.  He seemed to buy it though he said he would have chosen a less bright color.

2The worse sound you can hear while dressing to affirm your gender identity is the sound of a key in a lock.  In those moments I become an expert sprinter and I may have even been able to give an Olympian a run for their money.  It was always good to have a go to place and if you have make-up on as well, it was pretty well going to be the bathroom.  On this occassion I made it in and started the shower immediately.  I then hid all the clothes at the bottom of a hammer and showered myself clean.  Always a close call, and a definite boost to my adrenaline.

1Playing hooky can sometimes backfire and at one point I came closer to being caught than I ever had.  At the time we had a boarder who shared a basement room with me.  I was fully dressed and not expecting anyone for hours and it was a surprised when I heard him coming down the stairs.  I had no where to go other than the room and then into the closet.  I was quite literally trapped in the closet as he came into the room and it didn’t look like he was planning to leave,  I had to think.  I had no place to hide the clothes so I was going to have to put clothes on top of them to escape.  I found a pair of sweats and a big shirt which covered the girl’s clothes I wore well enough.  I used another shirt to wipe off make-up.  There was only one problem, I had panty hose on and no socks to cover up my stockinged feet.  I had to rip holes in the toes to pull them up off of my feet.  I then leapt out of the closet as if I had been in there to scare him then feigned a great need to pee where I could stash the clothes and clean up properly.  He never seemed to notice anything, I was lucky.

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