My first outing as a CD

[slkdyk]

I have come up with a scenerio for my first outing as a Crossdresser. It will be at night. I will dress at home and sneak into the car to avoid the neighbors. I will be dressed conservativly, not slutty. I will have heels, nylons and either a skirt or slacks and either a plain top or jacket depending on the weather. I also have to master the heels before then too. It may still be cold so I dont want to look too much out of place. I will drive to my local library parking lot after hours, depending on the night it could be after 6p or after 9p. The branch I am thinking of has a fair amount of after hours activity at the book drop so I may have to avoid some people. Depending on the activity I will park as far from the book drop as possible and walk over and deposit my not yet over due book into the drop and return to my car. If there is too much activity I will park closer. It is a very well lit area but not so much to be recognized from a distance. This is a rather mild scenerio but will be my first. I will have some play time later in March so hope to do this then. I will let you know what happens afterwards.

So, what do you think?

[bound_jenny]

Sounds like a plan.

And you got it right - the best way to go unnoticed in CD is to not attract attention with your clothing.

Jenny.

[Michelle]

This is a rather mild scenerio but will be my first.

For lots of folks here it is probably mild, but I have been into bondage/crossdressing for a while and I haven't done anything this risky yet
Don't forget to let us know how it went. And feel free to explain with all the minor details in a 24 page document
Michelle

[onestrangeguy]

I will be dressed conservativly, not slutty. I will have heels, nylons and either a skirt or slacks and either a plain top or jacket depending on the weather.
Depending on the activity I will park as far from the book drop as possible and walk over and deposit my not yet over due book into the drop and return to my car. If there is too much activity I will park closer.
So, what do you think?

Dressed conservatively is fine, and at night certainly works. Avoiding the neighbors is a good thing too. As for the 'skirt or slacks' change that to 'Skirt or dress', Slacks are not allowed. True, you don't want to look 'Out of place', and dressing appropriately for the weather is fine, but if you wear a jacket or sweater it has to be a feminine looking one.
If there is to much activity, you sit and wait until it is quieter, parking closer is not allowed!
Mild scenario's are fine, and can be a lot of fun. Just remember that your imaginary mistress won't let you wimp out.

[ponylady]

I have come up with a scenerio for my first outing as a Crossdresser. It will be at night. I will dress at home and sneak into the car to avoid the neighbors. I will be dressed conservativly, not slutty. I will have heels, nylons and either a skirt or slacks and either a plain top or jacket depending on the weather. I also have to master the heels before then too.

make sure you master driving with them, too. this is quite different from normal shoes.

[onestrangeguy]

My thought exactly. I was going to add to my post, and forgot:
You're allowed to slip the shoes off when you get into the car, but they have to go back on as you step out.

[Kronopticon]

i think the biggest mistake a TG can make is dressing how men want women to dress, which is VERY slutty, its an urge you have to fight with your life i know i have. though i was horribly surprised one time when i had my ass smacked while i was walking down a busy highstreet, in my opinion, i think i wasnt convincing enough, otherwise, i dont think he would've done that... that or he wouldnt have gotten away with it with too many "girls"

[onestrangeguy]

I don't know much about the TG thing, bur as an occasional cross dresser, I couldn't agree more. To me it's all about fitting in and not making yourself stand out. If you can do that people will just think you're female and not notice you beyond that. Dress to slutty, and you get all sorts of unwanted attention. This could be good, or bad depending on what you're looking for.

[slkdyk]

I know this sounds very mild but this would be my first outing. I cant wait to try it.

[marylandsissy]

I know the older I get, the longer my skirts get. I like the ones that hit just above the knee now. Mini skirts work for the slutty stuff. But for me, at the one play party I attended, I had a black pleated knee length skirt, tan pantyhose, black stockings, 3 inch heels, white blouse, etc etc. Use you imagination about the rest of the lingerie Granted I only had to walk 3 blocks to the play location. But I turned a few men's heads as I and my escort made our way down the street. But the way I was dressed, did not attract undue attention to either of us. Rule of thumb, blend in. Now in daylight, I am not too able to pass, but at night on a dark street with lights every so often, I can do it, plus knowing how to swing your hips is a plus.

[slkdyk]

I know this may seem very mild but as my first outing it was awesome. I was finally able to get out the other night. I had on heels and a skirt just above the knee, not real short. I followed what I mentioned above pretty much as described. I pulled into the parking lot, which was fully lit but empty. I got out and walked over to the book drop when a second car pulled in the lot. It was alot closer to the building than where I was parked. I finished depositing my book and headed back to my car. The person started getting out of their car about the time I was closest to them, about 25' away. I tried to act as natural as possible. It was a older man that only took a slight glance at me. I guess I didn't look good enough for a longer look. I got back in my car and was out of there in a shot. About the only thing I can say about the experience is WOW.....

[teather]

Congratulations! It brings back distant memories of the incredible high I experienced after my first outing fully crossdressed (I was 15 at the time) - I went out walking in the darkness on a snowy evening dressed in my sister's school uniform, gabardine raincoat and a pair of my mother's high heeled boots - not a scrap of male clothing. The boots were a big mistake because I wasn't used to walking any distance in heels. Unfortunately, I had to extend my route to take detour so I could avoid having to pass a man out walking his dog. It's kind of scary when you are out alone at night dressed as a schoolgirl - it certainly made me appreciate how vulnerable a woman alone might feel. By the time I got home my calves and thighs were burning and I was desperate to get the boots off my feet.
A couple of years later I was out walking dressed in a pink mini belonging to my sister and another pair of my mother's boots when I was wolf-whistled (the only time in my life ). I later found out that my mother hardly wore the boots because she thought they made her look like 'mutton dressed as lamb' . That outing probably counts as too slutty - although I am not sure that the unwitting donors of the clothes would be too flattered by that!

[onestrangeguy]

It sounds as though you had fun, and that's the real purpose of what you were doing. I know i have thought about the possibility of 'Getting caught' myself. Then you go out as you did, and you end up asking yourself just what 'Getting caught' means? If a car drives by, does that qualify? did your guy qualify? The next time you are out someplace (In normal mode) think about who you see, who look at, how closely you look at them, and what clues you in to their gender and other factors. I know in my case, I look at their clothing., and perhaps their hair. Dress, and long hair - It's female. Your guy probably did the same and as you said, unless you were a good looking female, he probably had other things on his mind. The darkness helps to conceal you some too.
My point is really that You know what you are doing, and your mind greatly exaggerates all of the perils and dangers. That is what gives us the rush, and what makes it so much fun.

[slkdyk]

Absolutely it was fun..... I didn't feel I was caught by the passer by either or the several cars that drove by while I was dropping the book in the drop. Had the adrenaline going though. Cant wait to try it again but don't have any time to play in the near future yet so Ill have to wait patiently until I do. Thanks so much for the support.