Welcome to Crossdresser Heaven, a safe and welcoming place for everyone in the crossdresser community.
Join Crossdresser Heaven today to participate in the forums.
So I’ve been going to weekly therapy sessions with an incredible doctor downtown Chicago for a few weeks now. I’ve gotten to a point where I felt comfortable being 100% me around her. She actually gave me a homework assignment last week. Find a cute outfit and wear it to my next appointment. Well, I decided to one up it after seeing how my makeup came out. I asked her if she would be okay with me coming fully dressed, wig, makeup, everything. It took a couple days for her to see my email and I unfortunately just got her reply this morning. The morning of our session. Glad I had a little foresight and packed everything before I went to work. Unlike my last time out, I triple checked I grabbed my makeup bag lol.
Went to work as usual and was a bag of nerves all day. Not nearly as bad as what was to come, but still nervous. I’ve gone out before, but holy shit... I’ve never walked down State Street and Michigan Avenue in full dress lol. The amount of people not including the people that could potentially recognize me, I was in an utter state of fear.
I left work early to make sure I had time to get ready to go. Ran down the street to a local secluded forest preserve and started my “conversion”. Outfit, check. Makeup, check. Brush out my wig and style my hair, done and done. Now time to hit the road. Oddly enough, I was completely at ease and comfortable. As soon as I looked in the window to see my reflection, I was pleased and my mind was completely clear. I thought back to some of the comments some girls on here left on one of my posts. I figured you girls must be telling the truth. I’m gorgeous damnit and I’m going to take this afternoon by storm!
Yeah. Right. I parked in the parking garage, did a last makeup check and hair inspection, grabbed my purse and went to step out. I froze. My nerves took over and felt like they were suffocating me. I considered taking everything off and going in male mode for about 15 minutes. After sitting, crying, worrying, redoing my makeup and cleaning off my tear streaked eyeliner and mascara, I decided now or never, put on my big girl pants and stepped out. And totally opened my door into the valet attendant. Oops. lol.
Walked up out of the garage hiding my face behind my big faux fur hood still terrified of not passing. Checking people as I went to work make sure I wasn’t getting any inquisitive looks, I made the short walk to my doctors office. The whole time feeling comfortable but nervous at the same time.
Got to her building and a honestly good looking professional guy about my age rushed ahead of me to hold the door for me. Too scared to open my mouth, I simply gave a smile and went on my way. Walked by the front desk with no issues and went to the elevators. A pretty girl jumped in with me. I was far too scared to show my face still so just buried my nose in my phone and ignored her. Yeah. Really kind there Skyler lol.
Now it was time for the waiting game. I sat in her waiting room all alone for what seemed like hours. I didn’t tell her I made up my mind to come as Skyler and decided to leave it a surprise. Finally the door opened and she greeted me. First she looked puzzled. But that quickly faded and turned to elation. I questioned her if it was too surprising for her. She told me what was surprising is how naturally feminine I really look.
For the next half hour we talked about how I felt about being out in the city as Skyler. Then I decided to ask the big question that was on my mind. Do I pass?
Her reply was all I needed to become fully confident in who I am. “Not only do you pass as a genetic girl, you are absolutely stunning. I would tell you if something was off about your look. Our sessions are about honesty. And honestly, you are beautiful Skyler.”
I spent some time after my session walking around the city and enjoying being me. One or two stray cat calls were fun lol. I was on Michigan Ave, the main drag for those of you not familiar with Chicago, so those cat calls could have been directed at anyone. It was fun to think they were for me though lol.
Today was incredible. I can’t wait for my girls weekend with my fiancé now. I’ll post pictures of my look tomorrow. Thanks for bearing with me through all of this lol.
💕Skyler
Really nice post!
I know that relaxed feeling of being dessed and just feeling like finally being you.
That must have been a wonderful experience, Skylar. I hope you treasure the experience.
MacKenzie Alexandra
Skylar,
Thank you for sharing your experience with your "Doctor" I can relate to your counseling. I admire that you attended your session enfemme before you met her. I admit, my therapist is in office that shares a day care ... My insecurity to pass with parents and children is not ready.
However, Heather(my therapist) encourages my dressing as a woman. I dress in a bathroom and Leonara appears as the woman ready to talk as woman. It is a wonderful experience.... Skyler, I hope your session with your counselor was also as rewarding as mine.
Your article was very informative and I am sure the ladies here were grateful.
Thank you ... Leonara
Skyler......way to go girl....I am thrilled everything went well for you.
Hugs and kisses..........
Dame Veronica
Skylar
I truly enjoyed reading about your trip to your therapist. I could feel what you were going through with the doubt about if you could pass. I know that feeling. Everyone of us has doubts about if we can pass or not when we decide to go out in public for the first time.
I remember when I went out dressed en.femme for the first time. It took me forever to get the confidence to leave my motel room and walk to my car.
I drove to a mall and parked as far away from the entrance to the mall that I could
I sat in the car and looked at myself in the mirror on the sun visor telling myself nthat I could pass.
I still had doubts and I just sat there.
I started the car and I was ready to leave.
I looked at myself one more time
I shut the car off and put the keys in my purse. I opened the door and got out closing the door and locking it
I put the shoulder strap of my purse on my shoulder and began walking towards the entrance to the mall
My heart was racing and pounding as I was getting closer to the entrance. The adrenalin of what I was doing kept me from turning around and going back to my car
I began to meet people who were leaving the mall and to my surprise no one was paying attention to me.
This was telling me that I was passing as a female going to the mall.
I was thrilled that I could pass.
My first time out was successful. I've been out many times since but the feeling that I had the first time was the best
Congratulations on your first time Skylar
I know that you will never forget it
Janine
Skylar I am so happy for you! You was able to put your fears to one side and be yourself out in public I bet that just felt incredible! Your therapist truly sounds amazing and a great support for yourself!
Samantha x
Excellent work ! Congratulations. It's about being "honest" your therapist said.....very insightful I should say.. Secrets makes us sick. I have had so much therapy mostly due to my alcoholism (15 years sober), I have credits towards being a therapist lol.
"Rigorous honesty is nothing short of hard work. It takes courage, after all, to speak our truth. It takes strength to be vulnerable"
Thanks
Lisa 🙂
Skylar this is an amazing and inspirational post if I have ever read one! Your courage was so awesome! I am so happy for you. Your therapist is so amazing too!
Thank you so much ladies. It was a rush. After she said I’m not only passable but stunning “like you could be a model” is what she said lol.
I told her I was nervous that I was going to try too hard or that my natural stride would appear over the top or something. Like I don’t walk like a guy ever if that makes sense but I felt like I had to show off or something for my first time in the city. Her response to my worries? “What? Do you have a total runway walk or something? If you do, god, go for it. You could be a model!” Yikes. Totally wasn’t expecting that level of encouragement lol. I still have my doubts even though I know inside she won’t lie to me and is 100% totally honest. I just have a lot of insecurity with my appearance I guess. Like I don’t want there to be a trace of male left in my look. I’m not a guy so why would I want any male attributes??? Idk. Maybe it’s just my head still spinning...
I enjoyed reading your story. I too was terrified the first time I ventured out fully dressed. It does get easier the more you do it. But even after venturing out occasionally over the past 2 years, I still find myself in situations where I'm less confident. I remember my first time walking down a very crowded and busy Chicago street during the daytime. It was much different than some of the more laid back, less busy places that I ventured to before.
If I would give one piece of advice, confidence is key to passing. If you look nervous and are constantly looking down, people are more likely to pick up on that. Chin up, look forward. If I find myself a little nervous, I try not to make direct eye contact with strangers. I just kind of look past them. If you find yourself in tight quarters with a bunch of people (like an elevator) pulling out your phone and focusing on that will help calm your nerves. And it looks normal, as that is what everyone does these days anyway.
So excited that you are finally able to be yourself! 🙂
Attagrirl Skyler, that was an inspirational triumph!
You are a beautiful woman
WOOOO!! YOU GO BABE!! =D
You made this ol’ redneck gal so happy for you. 🙂
Wow, that's a great story Skyler! Good for you, girl!
