Being Dressed in a Big City for the First Time

My wife, who knows and loves my crossdressing side of me, had invited me to go with her to a big city for a concert. Despite my initial preparations, she insisted I pack everything I needed. Everything.

Transporting All My Clothes

This trip was domestic, so I didn’t have to worry about declaring any luggage. It was also unlikely an agent at the gate of the airport would fully search the luggage. I took the caution to buy another bag exclusively for women’s clothing, along with any other makeup and extra accessories needed.

The onboarding and flight itself were fine. I had not dressed for this leg of the journey due to my official government ID still using my birth name and having my masculine photo on it. Once in the big city, a taxi took us to the hotel.

After lugging all the baggage to the room, it was time to change.

Changing in a New Place

Provided most items have been brought that you would normally use, the process of changing isn’t much different to home. I managed to bring my razor, makeup, and silicone breast forms, so I had everything I needed. Even in an unfamiliar place, I could do everything I needed.

After shaving, putting the boobs on and doing makeup, I was ready. My eyeshadow was a gentle bronze and my lips were painted teak. When in public, in a big city you can blend in easier, but care should still be taken not to go too bold.

I also decided to wear a subtle white woolen turtleneck and jeans with a leather jacket. This definitely was not a bold outfit and should help me only get the desired attention of those checking me out, not more.

With an outfit on and boobs in place, it was time to go explore the city.

Being Confident in Public

In order to seem like I belonged in the city, I had to act that way. I used techniques for feminine mannerisms to match my outfit. This especially helped the more personal interactions I had. Shopkeepers and other retail workers would be closer to me, and I would need to talk to them and interact very directly with them. I would need to work hard to minimize the number of times I was realised.

When walking, I carry my head high and back straight. The bra I wear supports the weight of the breasts, and I wear taller boots to help support my ankles. Holding myself tall and confident makes sure people know I belong here.

I pass people on the street. Some realise I was not born a woman, and others are oblivious. Some look at me with a naughty look, and others give me respect. With confidence, I carry myself.

Retail Workers Will Respect You if You Are Polite

In reality, retail workers and others you encounter while out in public don’t care if you present femme. On a trip such as this do not have any issues for you while out and about while dressed if you are polite and respectful of the store and them.

In some situations, some may be happy to see someone expressing themselves openly! Always be polite when talking to the public and balance modesty and expression.

I flitter in and out of various shops along the street while dressed. I carry myself and can shop freely. I pick up dresses, shoes and makeup, keeping in mind how much I can take with me back home.

Adult Activities

As the night draws in, It’s time to experience some nightlife. Heading back down the street with the sun down means it is easier to wear something a little more scandalous.

It is early in the week, and so the only place really open is a small bar on the corner of a nearby block. I enter, sitting down while my wife gets the first round of drinks, something to take the edge off.

It can be something helpful to take an edge off when things are stressful. It shouldn’t be used as a crutch though. A woman like me keeps herself composed even under the influence.

I am nervous, playing with my hair and preening. I need to make sure I look my best if I want positive attention. My white hair fluffs a little from the amount of touching.

A woman nearby notices. She is older than my wife and I, but still youthful. She calls over to us, “You look wonderful.” This was so pleasant and really helped my confidence. I blush and thank her. We don’t think much more of it beyond the initial blessing. But shortly after, she comes over with tequila shots!

We do the shots with her, and she continues to compliment my wife and me. Eventually, she gets up to dance and drags us up. The boobs I wear make me a bit top-heavy, and so my dancing is not that good.

The lady, while dancing, introduces herself and her friend. Despite earlier reservations, I am starting to get a little tipsy and enjoying myself. The lady’s friend does some very suggestive dance moves and begins trying to Dunkley twerk on me!

I enjoy my time with them, and we spend a good few hours together. This whole time, the bar staff have been very polite and accommodating to us. With confidence in how I look and being respectful of other people at the bar, they have no issue with me being there.

Throughout the night several people do occasionally look over at me. None are confident enough to approach me fully, but I can tell they are checking me out.

This is my first time going out to a bar like this, so I am not confident enough yet to go over to them to chat.

Heading Home

The night draws close and the bar slows down. I am getting tired and it is time to head home. We find a nearby bus stop and catch it up the hill back to the hotel. A stranger sees me get off the bus and calls out to me.

“Mhhm mhmmm,” they call. The sound of seeing delicious food. They say it in adoration and desire. I feel external validation, and my wife feels proud and lucky to be mine.

My outfit is holding together enough that I still look presentable. The next mission, when we get back, is the door staff. As we head in, the receptionist looks me up and down, trying to figure out if I belong. After flashing our room key to them, they let us pass as we headed to the elevator.

With no major issues, I begin removing my makeup and head to bed to dream of another day.