(Please forgive the poor photo quality; at night pictures are difficult)
I have now experienced my first time of being crossdressed outside of my home (in the outfit pictured). I wanted to share my experience here, as I’ve been reading and appreciating other people’s success stories, so I will just add mine to the bank.
I’ve been interested in dressing up, pretty much forever, but realistically, I’ve actually only been doing so since high school. It began with some of my sister’s old clothes, which were left behind when she went off to college, and it eventually graduated into me buying some of my own. Throughout college, I dressed very sporadically and never held down a solid wardrobe. I’ve gone through too many purges to recount.
Recently, my general mood and mental health have been going through a downturn. In attempt to correct it, I thought deeply about some changes to make. One of the biggest things weighing on my mind has been the fact that for the last decade I’d been keeping my dressing secret from everyone in my life. I’ve started telling people, my sister and close friends. Opening up has been a fantastic experience; everyone I’ve told has been supportive and gracious, accepting me without hesitation.
That brings me to going out. Last week, I went out shopping with a girl friend of mine. Now that she knows, it’s a fun new thing we get to do together. It’s been great. We bought some dresses, shirts, shoes, all sorts of stuff, and put together an organized outfit. I made plans to hang out with a group of people, all super open and nice. When Saturday rolled around, I prepared myself. I showered, shaved, and dressed all the way up as best I could.
The hardest part of the evening was getting out the door and into the car. I was going somewhere and wearing something completely different from what I would normally wear outside. The drive over was exciting and nerve-wracking. When I pulled up to the place where we were meeting, I sat in the car for a couple of minutes. The place we’re meeting at is a club, real calm and low key. The people are super nice and open about everything, so without a doubt, it’s a great place for my first outing.
As I entered, I was immediately greeted with a smile by the girl behind the counter. I’ve been here before (not dressed) so she just said “Hey, welcome back.” The rest of the night went along in similar fashion, no real issues.
The best lesson learned from my experience; it really wasn’t as big of deal as I was thought it would be. Some people treated me no differently. A couple of ladies complimented my dress and shoes, and one girl said “Damn, you dress up nice; I didn’t even realize it was you.” Those were the best responses I could have received. I was able to just be me with the people I enjoyed being around. It didn’t matter if I looked like a girl or a guy.
For anyone who’s looking to venture out dressed, here’s a good protocol to follow. Trust in your friends, they like you. Find a friendly, open-minded group of people or club, and hang out with them in your guy clothes first. Then, just bite the bullet and go for it, and hopefully, you’ll be glad you did. Opening up, allowing myself to enjoy dressing up to the fullest extent that I wanted to was one of the most liberating and awesome experience I’ve had to this point.
Hi Sarah, what a inspiring article, especially for a girl like me, that wants to go out dressed femme, but never has, due to, for want of a better word, courage! I admire you! well done! i’m glad everything went well for you, and yes, I totally agree, your friends are what make you and i’m very privileged to very good friends here 🙂 . Your clothes are lovely, you’re very pretty 🙂 . Thankyou for sharing your article with us!
Fiona xxx
thanks for sharing your great experience. I did the same new years eve and it was great. even the folks who figured it out either didn’t care, or seemed to get a kick out of it that I’d be a bit daring. the high of having done it is still with me days later. it was an incredibly liberating and positive experience.
Such a lovely story Sarah. Be true to yourself in all things love. Life is so much better then.
Hugs,
April
Great story and you look fabulous.
It gets easier each time.
Thanks Sarah for posting, and you look amazing! So feminine and fashionable! That’s really great you took that difficult step of going out dressed, and that you’re able to share that part of you with more people. I was struggling with putting an outfit together today, it’s really cold where I live. I bought a really cute dress yesterday that has spaghetti straps like yours, but was thinking it will have to wait for Spring. Seeing your outfit reminded me of that wardrobe hack to wear a layering top under a sleeveless dress. Paired with leggings and boots, I now… Read more »
Sarah,
thanks for sharing your story! My first time out (well first time interacting with someone at all) was three years ago when I “went for a milkshake" ( https://www.crossdresserheaven.com/it-all-started-with-a-vanilla-milkshake/ ) (you can read other stories of my outings on the article tab on my profile page). Your advice is great-go out in groups -or at least with a friend (another CD or GG friend is great) and be confident -for as you said it is ALMOST NEVER as bad as your imagination going wild tells you!
Cyn
You inspire me and you so rock that outfit! Love the boots!!
Sarah thank you for sharing your inspirational story. You look amazing.
So happy for you, i’m still a “someday i’ll do it person"
hello and welcome, your out fit looks fabulous, its nice to get out when you can with out being spotted by neighbors. when going out i bet you really enjoyed your self and being the real person you should of been. i started with a pair of tights in a school play i was hooked, but my x dressing went away for years then came back stronger. later in years my wife found out, my daughter knows and that is it, my niece might know for i had her dress me up for Halloween. i have now more female cloths… Read more »
Love the story,lot ways it’s it came out to be a good thing.now me,love crossdressing but still new,but been panties since the of 10yrs old.mom found out,after hearing my feelings she saw no harm,no big deal,started wearing full time at 11 until after my divorce. Want to start again,most likely real soon.love sleeping in women’s sleepwear,been doing that 1 week after I got married…