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.

Hey Kano…

Any news about your Hotel/Motel adventure ?

Well, I finally dared checking out in blouse and skirt 😊 But I‘m still looking for a solution for a lock with an opening time window.

Well, I finally dared checking out in blouse and skirt 😊 But I‘m still looking for a solution for a lock with an opening time window.

Fantastic. You have taken that first step into being a woman.

Now, if you’re comfortable in your outfit, you can try to do some bondage.
Locking strap on your heels so you can’t remove them would be a good and simple start.

For the skirt, if it’s a belted skirt, a padlock through the buckle will prevent you from removing your skirt until you get home.

Unless you have a back zippered top, making the top lockable will be a challenge. And I’m not sure how it would work, but thinking about it, if you wear a locking collar, then you could poke a hole or maybe sew a small D-ring on the back of the shirt. Then you can lock the shirt/top to your collar.

You could also get your self a set of thigh cuffs and a short length of chain and wear that under your skirt, if the skirt is long enough.

Any way, congratulations on your first step.

🙃 thanks a lot !! Returning home in skirt and blouse would be the real challenge. Don’t know if I dare that already. But it would be easier to realize. All it needs is just a robust chain and a heavy lock to lock away all unnecessary clothes. The key waits at home..

Years ago, I would have to meet a food truck at my work place at 6:00 am.
Because it was 85 miles away, I would leave the house around 4:00 AM.
At that time, I would wear a pencil skirt, black with my favorite bright red top with bra.
I would bring my work clothes with me in a bag and change in the restroom before the food truck shows up.

Really exciting, just hoping that a cop would pull me over…. Not really, but that was many years ago.
Why did I stop? Simple. Food truck now comes on my day off. So now, I leave at 6:30 am in the daylight.

But, it was fun if not terrifying.

I just checked back into the hotel—wearing a skirt, a bra, a T-shirt, and a scarf. The girl at the front desk was the same one who checked me out the other day—she recognized me right away 😊

Good recognized or bad recognized?
Did she say anything, like “welcome back”??