3 Steps to Successfully Crossdressing in a Foreign City

Crossdressing in another city

I’ve spent the last week with a friend in California. It’s been wonderful to get away from home, spend time with friends and decompress from my last surgery before heading in to my next one (22 days until SRS!). I’ve also enjoyed seeing the local attractions around Hollywood and Santa Monica, and even overcame my fear of skimpy swimsuits by wearing a bikini to the beach. The day was gorgeous and the sea far too inviting to miss out.

This got me thinking a bit more about the many ladies I’ve corresponded with who wait with anticipation for travel to let their inner woman dance. For some the thought of crossdressing so close to home is enough to send chills down their spine. With breathless trepidation they ask, “What if someone I know sees me?”. And it’s all to easy to follow this line of thinking right into a catastrophe of life altering proportions.

The anonymity a foreign city provides can provide comfort and courage to the weary cross dresser. Though I warn you not to seek the sapid time en femme in a strange city without some forethought. Here are 3 steps to getting the most out of your cross dressing sojourn:

Crossdresser Heaven - Find Your Tribe
  1. Plan What You Will Do: It’s not as much fun spending the evening in your hotel room. Planning a few weeks in advance will ensure a memorable outing. Get in contact with local transgender organizations (there’s a great one in Seattle called the Emerald City). Ideally you’ll be able to make a meeting of the local chapter and join them for dinner and drinks – an out of town guest is always a treat! At the very least they’ll be able to tell you about transgender friendly parts of town you can enjoy. Another alternative is to contact an organization that provides cross dressing fantasies for a fee (in Seattle The Emerald Fantasy is one example. This might cost you a bit, but will ensure a magical cross dressed evening.
  2. Plan Your Outfits: Since you need to fit everything in a suitcase you can’t take your whole wardrobe with you. Put together outfits for each day or night out a few days in advance. Don’t forget jewelry and makeup. If you’re just finding your style try them on in the mirror before packing – there’s nothing worse than having places to go but nothing to wear.
  3. Get Confidence from Unfamiliar Surroundings: Remember, it’s likely that you’ll never see any of the people you meet again. Use this as an opportunity to be fabulous! Enjoy yourself and let fear take a back seat. If you drink, start your evening with a glass of wine at the hotel bar to get used to your femme self before sauntering out in the world.

There you have it ladies – there’s no excuse to put off your fantasy. Grab your suitcase and airline ticket and let your inner woman shine! Whether it’s an indulgent personal vacation or a few hours after a business trip you’ll be thankful for the time spent expressing yourself. Be safe, have fun and look forward to next time!

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