Some ideas for a hotel adventure:-)

Heya 😊 
I‘m planning a business Trip by car and including a stay in a hotel. I‘m planning some entertainment for the night and haven’t been able to resolve one issue - maybe you have an idea .. 

I’m transsexual but still not publicly outed. I’m using such opportunities to be myself and set things up the way that I am forced to show myself. 

My idea: in the hotel room I get rid of my male clothes, then dress as a woman, stuff my male clothes into my travel bag. My trousers will be secured by a sturdy chain which I thread through the trouser legs, my T-Shirts, etc. and lock with a padlock. The key to the padlock I leave in my car, down in the hotel's parking lot. That means, in order to get the trousers etc back, I will *have to* go through the hotel sometime, dressed as a woman, and go to the car to fetch the key. Sure, I could wait until late at night, but I’d like to have some sort of a time window, which I’m forced to use to get the key. The alternative being, having to wait until breakfast time, when the hotel is crowded.. 

Do you have an idea how to set up such a time window ?

This will require a little willpower, but this will make you a bit more confident and comfortable.
Forget the bondage stuff.
Select an outfit that is not over the top.
A round or scoop neck top that is not baggy and not tight. A basic bra that has molded cups will be enough to show through the shirt making a good fit. A basic skirt, knee length. An A-Line or a straight skirt is a good start.
Basic Control Top pantyhose, nude if you shaved your legs, otherwise moca or suntan.
Shoes, low to medium heels, nothing over 1.5 inches.
Go to your motel/hotel like normal, do your business work or whatever your job is, as normal.
At check out time, get dressed as a woman, pack your things and go check out.

The evening staff and morning staff will be different, so there shouldn’t be any problems or issues.

Get In your car/truck and drive off.

You’ll be surprised how well this works and your confidence will improve as you do this more often.
Remember, you’re not a Drag Queen, your a woman.

My favorite out fit is a red simi tight round neck tee, with a straight black skirt, just above the knee or mid-length and a matching black vest. And I wear 2 inch heels or 1 inch black boots.

Hope this helps.

And don’t forget to wear your makeup.

Forgot to add.
If you’re going with this look, I would recommend using small to medium size pearl earrings. Also, glasses. Get the fake black type with clear plastic lens.

For a second outfit, same foundation, bra and panties, nude or moca pantyhose and a round neck, long sleeve simi tight black spandex dress. 2 inches heels and maybe a small red belt… or not.
Same glasses, but a set of Dangling earrings.
Red lipstick to add color.
Now you’re ready to head to a party or bar.

Just remember, it’s not really you, it’s your outfit that sells you.

A bra and panties under jeans and shirt means nothing except when it’s something you need to get comfortable with.