Getting out while Crossdressed

My first number of outings aren’t really much to write about, but I’m going to anyway, after all, this is my blog. I do hope though that you stick around and that it does provide a bit of entertainment, if you don’t have anything more pressing to do that is. Unlike a number of stories I have read, (grandiose plans, club meetings or conventions or with a big sister), mine would consist of a quick stroll around the block late in the evening, alone. Initially, just the thought that as people drove by, that, by the sight of the girls jacket, jeans, type of shoes and long hair I was displaying, would lead them to believe they were seeing a woman. This was what was exciting to me.  As a side note, isn’t it strange, at least for me it is, that in order to get out and be seen as a woman, you have to get out of the house or apartment without being seem?

One evening I did venture out in a short skirt, but upon returning to my apartment realized what I had just done. Short skirt, well, actually a really short skirt, high heels, walking around the block, at night, eh- gads, I looked like a hooker. I didn’t want to attract that kind of attention. How come I didn’t see this in the mirror before I stepped out? Obviously I was in a different state of mind. Lesson learned.

Despite not having had any bad experiences while being out crossdressed, I just have not had that many opportunities/occasions to pursue this. There are a few stories that I will be telling you about being crossdressed a number of years ago at Halloween, in the presence of a number of friends and fellow students and a couple of other occasions, but you will have to wait for those. Here now, I will regale a couple of experiences while being out alone.

So, how many outings for others seem to consist of getting all dressed up and then just driving around?

Well that’s what seemed to be involved in most of mine, until one occasion I had to get out of the car….I really needed to pee! The majority of these outings I would be wearing jeans, a blouse, jacket and girls runners along with my brunet wig, as I felt this would make me not get noticed so much (just trying to blend in as a “normal” woman). There was a highway service centre that I had been through in guy mode and know the layout of. Large gas station, snack shop, McDonalds, and the washrooms in back, accessible from the rear parking lot. It was mid week, about 9pm so not many people were about. I parked in back and proceed up the outdoor back stairs. I’m about halfway up the two story climb when a guy appears at the double glass doors at the top. “Shit, can’t stop. Can’t turn around, that would look stupid, got to keep going and pass him as he comes down”. But he just stands there, holding the door; waiting for me to get to the top…..he was being a gentleman…wow. I gave him a meek smile of appreciation and (what felt like at the time) dove into the “safety” of the ladies room. “Empty, good”. Things taken care of, I strolled out and returned to my car feeling quite confident and excited about what had transpired.

A couple of months later, so, that would be late fall of ’90, while driving from Ontario to Manitoba via Duluth Minnesota; I took the giant discussion to drive enfem for most of the last day. The room at the hotel in Duluth was on the ground floor with a glass sliding door right to my parking spot. After getting ready that morning (jeans and blouse again), I loaded the car with all my stuff, and proceeded to drop off my room key. I had paid the night before but still required the bill. I approached reception with trepidation and placed the key on the counter. There were a couple of others in the process of checking out and the girl behind the desk smiled at me and said she would be with me in a minute. I stepped back towards the back wall to stay out of the way, trembling somewhat with either fear of excitement, not sure which, but very soon was called forward with a “Mrs. X, your receipt is ready”. Mrs! “But I’m not married” I was thinking. This was probably due to the fact I had used my credit card, with male name, to pay, but here was this woman picking up the receipt, must be the wife. What a fantastic feeling.

After one rest stop along the way (a not very busy picnic site) I decided I should shed my girly exterior prior to crossing the border back into Canada. A quick use of the ladies room at the last picnic/highway rest stop before the boarder, followed by my impersonations of “Superman in a phone booth”, I go from girl to guy in my car, and then off to the mens room to check that all my make-up is off. “Man, the ladies was much nicer than this mens room”, oh well, back to drab.

These were two of my most enjoyable early outings, but I was unable to take advantage of these successes due to my chosen occupation and training at the time. Oh I hope I can get out again soon. I’ll be adding one more lone success story shortly, which come to think of it, was the last time I was out and about completely by myself.

Hopefully I didn’t bore anybody too much. Again, my experiences are not quite as colorful as some others, but at least they are mine.:)


1 Comment

  1. Diver123

    Very nice pictures ,now I can,t wait to meet you,hugs Angela

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