Crossdressing Storieslatest

First Time Daylight

stockings and heelsI have enjoyed crossdressing for many years, but really could not due to many reasons, the main one was being married. Being with her made the feeling of crossdressing shrink because part of the enjoyment was the buying of clothes. I could indulge myself in buying clothes for her and dreaming some.

Unfortunately she passed away a couple of years ago. About a year ago, the urge to crossdress came back. Since then I have bought some makeup, clothes and heels.



Today I put on my bra, a pink shirt and my new heels (red/black 3″ pumps), along with a pair of shorts. I had to run an errand in town where I would never leave my car, but would be in the busy part of the main area of town.

I live in a small town and due to my wife’s former job, am relatively well known. Since this side of me has been hidden from everybody, it was a thrill and a bit scary to see if I could do the errand. When I went to my car in the garage, I opened the garage door and then got in the car, so anybody driving by could have seen me in my heels.

Since it was relatively cool, I did have to have a jacket on over my shirt, but the seatbelt went nicely between my chest. I drove to the mailbox for the errand, dropped off the mail, and went back home.



I got out of the car once in the garage and then walked to the door button to push it. After pushing it, I headed inside with a little swish of the hips. It was thrilling. I wonder what my next adventure will be…maybe with some makeup on next time.

Submitted by Ashley Marcy

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3 Comments

  1. Just before COVID I had a serious health scare which really made me re-evaluate my life. I realised that for many years I had hidden the fact I wore skirts out of fear. My wife knows and more than encourages me but I was scared of what other people might say.

    Taking advantage of the lockdown I started wearing skirts every day. I don’t really have crossdress as such as I can never look feminine and am too lazy to get worked up about makeup. However since then I know wear a skirt 24/7 save for when I go to work or church. I am really happy and surprised with how few negative comments I get and how many positive ones.

    It will be a while before I come to work in a skirt but I am sure this will happen . I already go to church meetings in one

  2. Hi, I am a crossdresser who also loves to go in women’s clothing and get a nice makeup. I have been out in the Danish in women’s clothing for praiden in aarhus, which was nice. I go mostly with skirt for daily but also wear dresses, have only received positive comments.

  3. Hello, I am a transvestite of Mexico, it is a fascinating life, very stressful, but delicious, every time I have the opportunity to be and live as a woman the joy, congratulations on this site, very interesting products, greetings from Monterrey Mexico

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