Crossdressing is a blast when you're at home, but I know many wish to be out in public while they are their femme selves. If you haven't gotten to experience this already, I'd recommend doing some research first. Especially, for the town you may be living in. It's easier to go out to a place that is supportive of the LGBT community. Prior to going out all dressed up, go out as your usual self. Scope out the areas you want to go to. Check out the bars, or even restaurants. Have a conversation with the servers and bartenders. These are the people that will help you out, and give you some insight on the vibe of the usual customers. Some people worry that they may get recognized, but typically no one does, unless you want them to know.
Perhaps while you are traveling may be the best time for you to step out as your femme self. Either way, when you do go out. Own it! This is you, being friendly and having confidence is everything to have a good time and connect with those around you. Even bringing someone along may give you that extra confidence. It's much easier going out dressed up when it's an occasion that is crossdresser friendly. Perhaps an event of some sort, such as a showing of The Rocky Horror Picture Show as an example.
These are our top three cities for cross-dressing and some things to do while you're out to have a blast while doing it! Usually cities such as these have strong roots in the LGBT community and create events to celebrate and entertain during the night and day.
1.) Los Angeles, CA is known to be the mecca of entertainment next to Las Vegas. It also has many conventions and events to attend such as DragCon that is coming up in April. This is a wonderful segway into being able to be out in the open while crossdressing without having to worry about getting backlash. Plus, you'll be around other like minded people who can share this experience with you. If you are wanting a little bit of help before stepping out, The Boudoir LA is a full makeover service that gives the full experience of crossdressing with the help of three ladies. They even have an escort service to help you be out and about if you want to go to a Nightclub, Lunch, or even a shopping trip. So there is no need to bring any of your own clothing, just bring yourself to Santa Monica and they will hook you up and make you feel your best. Maybe you'll even learn a thing or two for yourself during this transformational experience.
2.) San Francisco, CA has a large LGBT community where whole neighborhoods are accepting and open-minded, full of artists, writers, and entertainers. Even if you don't identify as being gay or trans, this is a wonderful city to be who you want to be. There are plenty of spots to hit up that put on amazing Burlesque shows. What better place to be than with others who like to dress up and feel sexy as their femme selves? There are so many theaters around such as the Metro Operahouse bound to have an excellent show with their most acclaimed shows put on by Tourettes Without Regrets. We highly recommend checking them out! They may be putting on a show near you! The Exit Theater is another excellent spot to check out that has a large array of acts with various talented performers.
3.) Provincetown, MA is the vacation destination if you want to get away from a busy city such as New York. Commercial Street is the epicenter of all the excitement and abundance of LGBT community acceptance in Cape Cod. The town itself is laid back with plenty of cute little shops and restaurants to indulge in during the day, but when night time rolls around the clubs and bars are a blast! The Atlantic House is one of the best and longest standing nightclubs of Provincetown where all are welcome. If you are craving a busier atmosphere and the hustle and bustle of the city, Soho and The Greenwhich Village are all excellent places in New York to do just the same, but be aware, things get a little bit pricier in the city for both shopping and dining. Although, New York has many things to offer that are free, such as taking a stroll through beautiful parks, attending art galleries, and window shopping.
If you have had any experience going out as your femme self for the first time, let us know in the comments below! We would love to hear some of the best places you have gotten to go to and what had helped you feel comfortable being out and about.
Provincetown at the end of Cape Cod is a great place! So open and free spirited! Lots of drag shows and great fun! Pre-COVID was a lot more fun but it is still a great place to explore your wilder side without feeling embarrassed. What about in the UK, where are the best crossdressing friendly cities?
I am a very very proud crossdresser from Lakeland FL. And I want people to know that I am. I go out dressed all the time and yes I get laughed at and get those looks but I do not let that stop me I am very feminine and I let that shine through. I have support to and have straight women friends and straight men friends. I just love my life I am 58 years old yes a little thick not bad because the men I date say they like it so this is a plus for me as a crossdresser. I love the path I have chosen
I live in a generally LGBT+ segment of the midwest. It’s quiet here. But it’s a college town, really.
But part of me longs for, and heartily romanticizes the idea of living someplace (a) coastal and cute or (b) semi-rural and quaint. All truth, nothing is stopping me from quitting my job and moving out to SF, or Miami, or some rustic spot in upstate NY, only to find another job in writing/editorial (because that’s what I do), but it’s just not in my DNA to do something that enormously spontaneous. . . .
I have a friend that I have been out shopping with on several occasions. We haven’t had the nerve to dress femme as of yet but maybe someday. However, shopping for women’s things can be very exciting. Especially if you shop for bras, panties and other lingerie items which we have. I confess the first time we did this I was mortified. Totally uncomfortable and insecure. He seemed more at ease to me. He had little trouble holding panties up and asking me what I thought. On that first time when we walked into the bra department I sort of got cold feet. Okay I got cold feet and that ended our first trip out.
The second time I was much more at ease and had talked to myself about how silly it was that two guys couldn’t buy lingerie together. After all women had no trouble buying men’s undies. We even giggled a few times and felt the fabric and enjoyed the experience. This ended with both of us buying panties for one another. Albeit this time we went to two different checkouts like that made a difference.
On subsequent trips we shopped in sportswear, the dress department as well as lingerie. We were becoming pros by this time. Yes, if you are wondering we did get what I thought were a few stares or at least wondering eyes. Oh well. I don’t recall but I think it was this trip that I bought him a bra and panty set. He bought me a nightie and panties. OMG, we were like two girls. I told him we were boyfriends but he was uncomfortable with that idea and we settled on gurlfriends.
So, maybe one day we will take the leap. Who knows.