I finally went out - sort of

[evadan]

I'm on an overnight business trip about three hours from home. I brought some clothes to enjoy some Eva time since I will have a hotel room to myself tonight. I knew that I would need to get something to eat once I checked in and I realized it would be after dark when I arrive. So I started thinking on the drive down that just maybe I would underdress before I went to get something to eat. I have never underdressed before because knowing my luck, something would happen and I would get outed. Then I started thinking that I brought my boots with three and half inch heals and just maybe if my drab jeans were long enough, I would wear my boots as well when I went out. As I drove, I came up with some conditions that I would only go out underdressed if:

1. there were restaurants close by with drive-thrus
2. there were stairwells on either end of the hotel that I could park near
3. my room was near a stairwell
4. my jacket was loose enough to conceal my boobs
5. and my jeans were long enough so my ladies' boots weren't too obvious

As I got close to the hotel. I saw plenty of fast food places along the main drag. Condition 1 - check!

I got to the hotel and checked in. My room is on the second floor, next to the stairwell. Conditions 2 and 3 - check!

I started to get a little nervous but decided I would not think about it and press on. So I changed quickly - panties, bra, forms, purple blouse. I put my drab jeans back on. They were just long enough to make my boots look great! But not too obvious. I wish I had some women's jeans. I put on my jacket and it was loose enough to hide anything underneath. Conditions 4 and 5 - check!

So I grabbed my car keys and room key, and took a minute to make sure I didn't forget anything. Then I stepped into the hallway before I chickened out. All clear. I headed down the stairs. A new experience walking two flights of stairs in 3" heels. I went out the side door and of course there was a guy standing off to the side smoking. I just headed for my car - seemed like a long walk. I was a little unsteady and my heels were so loud. I was thinking they sounded pretty feminine. But I pressed on. I got in to my car, heart thumping and started it up. I was actually outside - maybe not fully dressed but still in heels, underdressed with boobs. I drove around for about 10 minutes and finally decided to try a chicken place. I pull up to place the order at the speaker and there's a sign that says I need to pull around to the window to order. Great! A young kid is at the window. I'm trying to order but I'm kind of tongue tied. Somehow I get through the order and head to the pick up window. There I have to wait for what seems an eternity. I get my food and head back to the hotel, praying that someone doesn't run into me or some other disaster happens. At the hotel, the smoker guy is gone. This time I enjoy hearing the sound of my heels echo off the building as I walk to the door. I get in and up to my room without running into anyone else.

That was fun and exciting. Small steps but a start. Maybe I need to get some ice cream now?

Cheers,

Eva D.

[DIANEF]

Small steps lead to bigger ones Eva, I've only recently started going out myself. Nerve racking at first but it does get easier.

[Elizabeth G]

Congratulations! It gets easier by the way. I'm glad you enjoyed yourself.

[Emily Ann Brown]

A trip across the world started with a step in that direction. Em

[Krisi]

Were you fully dressed and presenting as a woman or just a guy in heels and boobs?

I think one of the mistakes many of us make at first is trying to "sneak" about. Dashing to and from the car, sneaking in and out of back doors, walking in deserted areas in the dark, etc.

This is the sort of behavior that calls attention to ourselves. I think it's better to "own" it. Hold your head high and walk out the front door of the hotel. Take the elevator unless you're on the ground floor. In other words, you look like a woman, act like one.

Don't forget your purse!

[dolovewell]

I agree with Krisi... it reminds me of my earlier days of going out, where I would try to avoid people and sneak around. For example in stores like Macy's I would sneak around and manuveur my way through the racks and such and avoid the main paths. I would often hesitate and "wait until the coast was clear" before proceeding in some places. This will just call more attention to you. Eventually I realized that I have nothing to be ashamed of - so why try to hide.

[Beverley Sims]

Yes! You have to walk before you run, the story is similar to some of my early days.

I think we all go through experiences like you describe.

You can elevate the activity as confidence grows.

Good luck.

[phplayr]

Same here and I'm still working on it. One of my very first times out sounds exactly like yours. Keep it up and you will get more confident and daring each time.

[evadan]

Yes, I'm not ready to "own it." My make-up skills are not good enough - especially doing my eyeliner. It's hard enough learning how to do make-up when you are older (early 50's) but I need to wear my reading glasses to see. That makes applying eyeliner that looks good nearly impossible. My wife is supportive of my dressing but we haven't talked about going out. If she wants to help me, then I might take the full plunge one of these days.