The First Time.

This is an account of the first time I went outside dressed in women’s clothes.
I was in my early 20’s and believe it or not, married. My wife was slim and into short skirts and long boots, so there was an abundance of sluttish clothes around.
Anyway it was one evening, about October I think and we were playing cards, I can’t remember what game now, but it was cards. We had been playing for a while when my wife said she had a great idea, this turned out to be, “the loser had to dress up in the others one’s clothes”. Ok for her but not the same for me, anyway I agreed and we continued with the game of which I lost, strange, but true. She then went to her wardrobe and cupboard and can back with an entire outfit, including underwear and even a fancy dress wig.
I looked at her and said that I wasn’t too sure about this, but I got dressed anyway. Now I was standing in our lounge dressed in a black bra (packed out), black panties together with black stockings and suspenders. Over this I had on a tight light blue woollen pullover and a red short skirt that I can only describe as a schoolgirl gymslip. On my feet I had on a pair of black knee high “Go Go” boots, all this was topped off with a dark brown, shoulder length wig. My wife did take some photos but sadly they are no more.
We then continued to play and strangely I lost again, now she was looking round the flat for something for me to do, then she came up with the idea that I should have a cigarette, but not inside. No she wanted me to go outside our flat and have a full cigarette standing outside on the sidewalk. Our road was a quiet one in the evenings but people use to drive down the road as a short cut to the town. I walked to the front door and went to light my cigarette, but I was told I couldn’t light it till I was on the sidewalk.
She opened the front door the cold air felt strangely comforting as it rushed past my stocking covered legs, with my heart pounding I took the first steps outside. Thankfully the boots I had on only had short heels so didn’t make any noise on the path and arouse any of the other residents. It reached the gate and stepped out on to the sidewalk, I lit my cigarette and proceeded to smoke it. I then looked down and notice that this silly short skirt was so short it barely covered the tops of the stockings, so there I was a cigarette in one hand and trying to hold my skirt down with the other, yes you guessed it, a car turned into the road and was heading towards me. As I got closer I turned my back to it, it slowed and went passed me very slowly, then went on its way. I finished my cigarette and went back inside. My wife then asked why I turned my back to the car I told her I didn’t want them to see my face, she laughs they saw a lot more then your face and pointed to the back of the skirt, the stocking tops were permanently on show, I must have looked like a hooker.
Well that was my first time outside dressed in women’s clothes. There was more to come.
51-55, M
9 Responses Jan 18, 2013

Sounds like all kinds of fun to me. . .giggle

Oh my...this is a dream come true :)

You've had some fun experiences. Thanks for sharing then with us.

What a fun experience!


i just love it when the wind blows my skirt up when i am walking thru the truck stop parking lot. O yea i am a truck driver

I love it when my skirt blows up, knowing there's someone there getting an eyefull. Truck driver, cool.

its so much fun to have a female partner share our indulgence and to mentor us into our feninine personas...;-)

I enjoyed your story. I am curious... since you were dressed as a girl, did you smoke like a girl? Although I don't smoke normally, when I'm dressed as a girl I do, and I like to do it like a girl does.

Love your story!
How sheepishly coy of your wife!
How clever of you to, just happen to lose, at cards!!

That's great dear and I can hardly wait to hear more of what's to come too! ;-)

I have just put another on, under the section "I go out crossdressed", sorry im not too good with computers and its come up as been written by an EP User. The story is called "Dressing up".

Thanks dear, I'll look for it ...