My Travelling Experience as a Crossdresser

A complete guide on traveling as a crossdresser with essential tips on packing, destinations, and overcoming traveling challenges as a crossdresser.

Hello to my crossdressing family. I’m Marie, and I love traveling as a crossdresser.

Yet, just like many of you, I find myself struggling with shyness and a fear of stepping out in public, especially in a foreign place.

I had no confidence, but it was last month, while relaxing and reading a blog on Roanyer about traveling as a crossdresser, that I decided to face this fear.

I wanted to emerge stronger and more confident in my crossdressing journey.

And, Oh girl, what an experience it has been traveling as a crossdresser!

From choosing crossdresser-friendly destinations to packing my feminine travel bag, handling the airport drama, and living out my dream bikini experience on the beach, this journey has been transformative.

So, here is my story of traveling as a crossdresser. Let’s get started.

Where I Travelled?

It didn’t take me long to decide on Thailand as my dream travel destination, and there are multiple reasons for that.

The first reason is that it’s the most welcoming place for feminine men.

After seeing and reading about Thailand, I know it’s the one place where gender inclusivity is normal, like nowhere else.

It’s the one place where we can express our femininity without weirdos staring at us as if they’ve seen an alien.

Also, I was dying to meet ladyboys and party with them in the nightclubs of Bangkok.

I am not even kidding, honey; when I came to know about ladyboys, I was first stunned by the beauty of these men in Thailand.

After that, I decided that once in my life, I would visit these sisters of mine.

And the third reason I wanted to visit Thailand was to live my dream moment, to wear a bikini and walk along the beach like a diva.

I know Thailand is the only place where I can do that, unlike anywhere else in the world.

After that, I immediately booked my flight and hotel room in advance to avoid any hassle.

Pro tip when traveling as a crossdresser: Always book a hotel in advance to avoid last-minute hassle and unnecessary communication.

Sometimes, we should avoid interacting with people while en femme.

One more thing, book a hotel with at least a 4-star rating for a good experience, not just in terms of accommodation but also because staff members of well-reputed hotels are well-literate and understanding, which are good things for girls like us.

Best hotels in Thailand suitable for crossdressers

Crowne Plaza Bangkok Lumpini Park, an IHG Hotel

Conrad Bangkok

Lebua at State Tower

The Standard, Bangkok Mahanakhon

Mövenpick Hotel Sukhumvit 15 Bangkok

I booked crown plaza for myself because a sissy friend of mine told me that it’s a very good hotel, the staff is very nice and polite, and we can crossdress openly on the hotel premise, and it’s very normal there; no one judges. Perfect.

Why I Love Travelling En-Femme

Honestly, traveling en femme is a therapy for me.

I live in a pretty conservative environment, and as a crossdresser, it’s like being in a cage.

Dressing up in front of anyone I know is not an option for me. My family doesn’t get my feminine side at all.

And my friends still don’t know about my crossdressing.

So, you get why the thought of traveling en femme feels like liberation, right? It’s pure freedom.

I can wear whatever I want in a totally new place, away from my peers. No fear of getting ‘caught’ or judged.

I bet most of you get where I’m coming from.

We’ve all dreamed of just taking off for a week, being ourselves, and traveling as a crossdresser out in the open.

That’s why I’m telling my story – so you can get a little push and start planning your en-femme trip.

What Did I Pack as a Crossdresser Traveller?

Here comes my favorite part of traveling: the packing.

So, what did I pack? My trip to Thailand was for four days, and each day had a different location on my itinerary.

On day 1, I wanted to do some sightseeing and explore Thailand’s natural beauty, which is quite adventurous.

For that, I packed a pair of jeans, shorts, and a crop top.

For underwear, I packed a hiding gaff panty that I bought from Roanyer to hide my bulge without the need to tuck.

For day 2, I decided to visit the beautiful city and local markets of Bangkok during the day, so I packed a really cute floral dress.

It was very comfy yet sexy, off-shoulder, so I got a strapless bra to wear under my dress.

Although the bra wasn’t needed because I wasn’t wearing breast forms, we never miss a chance to wear a bra, right? So, I packed it.

Day 3 was my leisure day, and I decided to spend it on the beach, enjoying some Thai spa and full body massage, so I packed a one-piece red bikini.

Honestly, while packing, I thought I should leave it because I would be too shy to wear it, but thank God I packed it.

It was the best decision of my life so far. And if I’m wearing a bikini, I like to put on my breast forms, so I also pack them carefully.

For day 4, I wanted to explore the party and nightclub vibe of Bangkok, so I added a black plunge maxi dress.

To complete my outfit, I decided to pack a pair of hip pads.

Come on, honey, a maxi dress without hip pads is the worst fashion blunder for a crossdresser. So, I packed my hip pads.

Best Moments from My Trip

I Met My Bestie

I met my bestie in Thailand. As I mentioned, I’ve always been fascinated by ladyboys, and, oh honey, the universe made it happen for me.

Here’s what happened: On day 2 of my sightseeing, my city tour guide turned out to be a ladyboy. Her name is Jane.

The moment I heard her speak, I felt an instant connection, so I decided to have her as my guide. It seemed like she also liked me right away, too.

We spoke about a lot of things, especially femininity. She shared her story of coming out as a ladyboy, and I opened up about my love for feminine fashion.

We quickly developed a cute sisterly bond. She even gifted me a beautiful scarf as a gesture of friendship, which felt incredibly heartfelt.

Sometimes, I feel like I belong in Bangkok, and I have this funny feeling that I might have been a ladyboy in my past life. Lol.

I’m still in touch with my Thai friend – that girl is special, my first ladyboy girlfriend.

We speak on the phone quite often; I had a call with her just last week. She’s coming to the UK soon, and I’ll be giving her a tour of my place.

I wore a Bikini in Public

Honestly, I wasn’t ready to wear a bikini on a beach full of people. I felt too scared and self-conscious about my body.

Questions like “What if I don’t look feminine enough?” or “How do I hide my bulge?” kept running through my mind – the usual crossdresser dilemmas.

But Jane, my new bestie, actually gave me the confidence to wear it. We were sitting in the room, and my bikini was lying on the bed.

She entered the room. “OMG, Marie, that’s such a cute bikini; you’re going to look sexy today!”

I replied with a sad face, “I know, honey, but I’m not wearing this.”

“Why not, Marie? Look at it, it’s so cute,” Jane said.

I confessed, “Honey, I don’t know. What if I don’t look good? I’m not sure I can pull this off.”

Jane came closer to me and reassured me, “Oh Marie, you’re the most beautiful crossdresser I’ve ever seen, so don’t think too much,” and she encouraged me to put it on.

And oh my goodness, I’ll be forever grateful to Jane for this. In that one-piece bikini, I looked like a real diva.

I also put on breast forms to accentuate my figure. Honestly, even Jane was surprised.

She asked, “Are these boobies real?” and I just laughed so hard at that.

When we went to the beach, I removed my robe, and there I was, a closeted crossdresser, standing in a bikini among maybe a hundred other people.

It was a liberating feeling. Jane urged me to take a walk in my bikini. I asked her to join me.

My goodness, we had so much fun walking, and to be honest, I never felt odd.

No one was staring; in fact, some people glanced at me in a flirty, good way.

We walked past some boys playing volleyball and got teased in a fun way, which felt like heaven.

When someone compliments my femininity, it’s the best feeling – that’s what I live for.

OMG, that beach moment was like a scene from a movie.

A Straight Man Approached Me

By now, Jane and I had already become besties, so I invited her to go clubbing with me, and oh girl, the fun we had!

I wore my black plunge maxi dress with hip pants and breast forms to achieve a curvy feminine body.

So, there we were, Jane and I, in a pub, dancing and drinking, just having a blast.

And then something special happened.

Look, we crossdressers get a lot of attention from gay men, other crossdressers, and LGBTQ folks, but when a straight man compliments, that’s something else, right?

That’s exactly what happened to me. A straight guy, tall and muscular with a beard, Jason Momoa-type, walked up to my table.

He had a deep, baritone voice and asked, “Would you like to dance?” I was so flattered.

OMG, I felt so special; my heart was racing. I looked at Jane, and she gave me the green light. I took his hand and walked up to the dance floor.

I told the man, “I am a man,” and he replied, “Yes, I know, me too.” I was instantly attracted to him.

We were dancing, and then he suddenly kissed me. What a man!

He even asked me to go to his place. I badly wanted to, but I had to control my temptation.

I can’t just sleep with a stranger I just met in a foreign country.

So, I had to say no, and like a gentleman, he respected my decision.

Oh God, why aren’t there more men like this in the world? They’re so rare, right?

Challenges I Faced as a Crossdresser Traveller?

The start of travel challenges for me as a crossdresser began right at the airport, but I was prepared for it in advance.

So, there I was, waiting in the airport lounge in my denim shorts and a sports bra crop top.

OMG, honey, I felt like all eyes were on me. “You got it, queen,” I said to myself.

Then came the snide comment from the lady sitting in front of me, “Young man, have some shame!”

And I thought, “Here we go.” In my mind, I told her, “I am more woman than you’ll ever be, sweetie,” and just left the lounge.

I don’t interact with such lurkers.

Another thing about being a feminine man in Thailand is that most people assume you’re a sex worker.

I was walking with Jane on the street at night, and men were approaching us and offering money.

Jane advised me not to accept. There was a lot of inappropriate touching by some men, which horrified me, and I immediately left the street.

I’ll keep this in mind as a crossdresser: not to visit any shady streets late at night in Bangkok.

Apart from these incidents, my journey was a smooth ride.

Lessons from Travelling as a Crossdresser

Choose a very crossdresser-friendly place, like Thailand, which is ready to embrace and handle the femininity of a man.

The second thing is to pack according to your itinerary, including lingerie – that’s what I did.

This is crucial for us because we have to be more careful and conscious about certain things as crossdressers.

Otherwise, we might lose that feminine sexiness.

Another thing I realized is that when we put ourselves out in the real world, we’ll be surprised to find that most people are way nicer than we can ever imagine.

For instance, I could have never thought that I would make a best friend in a foreign land who would be my moral support in wearing bikinis or that a straight man would approach me like a gentleman.

Imagine if I had never visited Thailand; would I have been able to see this side of the world?

Probably not, right? So, as crossdressers, we should go out more often and try to connect with people.

Bullies are everywhere – yes, they’re everywhere, ready to pounce on us and take advantage of our vulnerability.

The best way to handle bullies is to ignore them simply. Honey, there’s no need to respond to them.

Brace yourself because you’re way above these people. Just move on.

Conclusion

This traveling experience has been really life-changing for me.

I am now more confident about my femininity and more often go out in the real world.

I am not afraid of meeting new people and talking about my femininity, dating straight men as a crossdresser, and making friends, all thanks to traveling en femme. It’s been like a coming-of-age experience for me.

I have decided to go to at least one destination every year en-femme.

Let me know if you liked my traveling as a crossdresser experience, and don’t forget to share yours. Until then, slay!