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First time out

7 Posts
6 Users
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Posts: 149
Lady
Topic starter
(@skyler1090)
Estimable Member     Chicago, Illinois, United States of America
Joined: 6 years ago

So yesterday, I exposed Skyler to the world. I’ve dressed in private with my fiancé (who supports me 10000000%)  but wanted to take a leap. I figured I’m turning 28 on Wednesday and have never had the pleasure of being the girl I sometimes wish I was in a more public setting.

I went to work as usual but packed a bag with “Skyler’s” clothes, wig, breast forms and shoes. As soon as I was off at 230 I knew I had some errands to run but figured why not do them as Skyler. I found an empty corner of our parking lot and quickly changed into my outfit in the back seat. Not wanting a colleague to recognize my car with a blonde in the drocer seat, I held off on the wig until I could find a better spot. I’ve worn an outfit while driving before but never a wig so I was a little jittery.

I pulled out of my work parking lot and pulled into the back lot of a Walmart a couple miles down the road. Took a peak around to see if anyone was in the area, then quickly got my hair in place, styled it and went to jump for my makeup bag. That’s when it hit me. My makeup bag was still on the counter in the master bathroom. DAMN! I guess I’m going to do this all natural! Good thing I shaved extra close this morning lol.

First things first, coffee. A 12 hour shift does some weird things to you. Specifically brings on the sleepy eyes (makeup would have been great with these horrid bags under my eyes). I walked to the counter of Starbucks and ordered my usual. The male barista didn’t skip a beat or give me a weird look at all. Phew, we’re good!  Then I made my first mistake. I forgot I was Skyler. I’ve become so accustomed to hearing my male name in public that I totally forgot my name when the girl called for my drink. Whoops! She was super sweet though and complimented my shoes and jacket choice.

Still a little worried about what I look like without makeup, i found myself a corner chair and buried my nose in a book. After sitting for a half hour or so, I got up to leave and happened to make eye contact with some random stranger clearly checking me out. Now I’m engaged, so I obviously didn’t act on anything, but I did give him a smile and continued about my day.

The rest of the afternoon went off great. That guy in Starbucks gave me the much needed confidence to get through the rest of the afternoon without worrying about my face lol.
<p style="text-align: center;">My wfiance and I are planning a girls trip in a couple months. This was just what I needed to be prepped and ready for a night on the town with my future wife. Can’t wait!</p>

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6 Replies
Posts: 1435
Lady
(@rbekka)
Noble Member     SF Bay Area, California, United States of America
Joined: 8 years ago

You are so brave, Skyler!

Glad it turned out to be a good outing for you!

 

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Posts: 0
Guest
(@Anonymous)
New Member
Joined: 1 second ago

Awesome story and a big confidence builder for you.

Lisa 🙂

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Posts: 149
Lady
Topic starter
(@skyler1090)
Estimable Member     Chicago, Illinois, United States of America
Joined: 6 years ago

Guess I don’t have to worry about not having makeup on lol. Thanks ladies!

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Posts: 271
(@charchar1959)
Reputable Member     Buffalo, New York, United States of America
Joined: 6 years ago

That’s awesome.  You go, girl!  <3

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Posts: 0
Guest
(@Anonymous)
New Member
Joined: 1 second ago

I am glad that you had a great outing! I find encouragement in your post. I have only made it to the mailbox and gas station.  You know, places where I don't have to use my voice. Very proud of you lady!

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Posts: 907
(@brittney2016)
Prominent Member     Cincinnati, Ohio, United States of America
Joined: 6 years ago

Hello Skyler; Thank you for sharing your story. I realize you posted this in October 2018 and congrats on it being your first public outing. I hope you don't mind me saying, your facial features are youthful and adorable. I think that's why you were able to get by without your make-up; more power to you. I'm a little envious, I definitely wouldn't "pass". It's great that you have a supportive S.O.

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