Cross dressers, share your stories of being out dressed, real of fantasy

Ok, I’ll put my money where my mouth is and tell the first story.
I am a passable, Asian 40 something cross dresser who likes to get out occasionally and do “normal" things during the day, ie: clothes or shoe shopping, get a coffee at Starbucks, lunch at a sidewalk cafe’, etc.
When I go out dressed, I like to really sell my femininity by wearing a dress or skirt and high heels. I’ve been told by some of my genetic female friends that I have a great pair of legs that they would kill to have legs that look as good as mine, so I like to wear high heels to really show them off.
One nice Spring morning, I was intent on getting out a bit into the real world dressed. I did my make up and dressed in a tan strait pencil skirt, matching heels and a semi opaque, white button down blouse. Under the white blouse I was wearing a sheer fabric bra in a nude tone to hold my breast forms. The sheerness and tone of the fabric of the bra made it look as if I’m not wearing a bra at all. The hint of my nipple and areola could just be seen through the fabric of my blouse, which was not my intention when I dressed that morning.
As I went about my day shopping and then getting a coffee at Starbucks, I caught some men staring at my breasts. I just smiled at them when they knew there were busted for staring, they just smiled back. As the morning went on, it became a source of “entertainment” for me to see just how many men would take note and stare at my breasts.
Near the end of my outing, I was looking at some bracelets in a glass case in a department store. An attractive middle aged female clerk was helping me when I caught her checking out my breasts too. As she looked up to catch my eyes, I just smiled and she blushed a bit and smiled back when she knew she was busted. I took this as a total compliment. May be I should go back to that store and see if more happens with the female clerk?

Kate

Very hot. Pics?
 
Thanks for sharing Kate!!! Great idea for a thread!

Back in my younger years (mid 20s) I was in a d/s relationship, I was pretty much a live in maid of sorts to a woman, lets call her Mistress Cindy. We kept appearances as a vanilla couple to friends and socialized out in our mid sized city.

Mistress Cindy liked to dress me as a woman as i did chores around the house for her. It became routine for me to change in feminine wear as soon as i got home. It was our private thing, but then Cindy suggested we go visit somewhere hours away. Somewhere I could go out in public as liz, somewhere far away from our friends.

We went out, I dressed as Liz, Cindy dressed a lttle more aggressively (sexier, tits out, skirt short) it was exhilarating for the most part. The looks (that day i was hot as i ever could be, nearly passable, but obviously a man dressed up) felt like daggers but Cindy held my hands and looked into my eyes as if she was a forcefield of protection. I noticed people talking even heard a word here and there but it was okay i felt safe enough. It was good. We spent the weekend there and it was pretty hot and i think about it all the time!
 
I spent a large portion of my life worried about what other people would think about me. A total waste. Once I opened the front door and walked out it dressed like a woman, the feeling was better than any street drug. I never looked back or coward in the closest again afraid and ashamed of who I am. Those that truly were my friends remained my friends, and those that only pretended to be my friends distanced themselves from me. I am a better person today, honest with myself; being who I am. Do I go out dressed? You're damn right I do! Best decision I ever made:)👠👠👠Kant


<----- the picture is me, judge for yourself :)
 
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I spent a large portion of my life worried about what other people would think about me. A total waste. Once I start opened the front door and walked out it dressed like a woman, the feeling was better than any street drug. I never looked back or coward in the closest again afraid and ashamed of who I am. Those that truly were my friends remained my friends, and those that only pretended to be my friends distanced themselves from me. I am a better person today, honest with myself; being who I am. Do I go out dressed? You're damn right I do! Best decision I ever made:)👠👠👠Kant


<----- the picture is me, judge for yourself :)

Kant you are an inspiration!! I will heed these words next time self consciousness starts to creep in!!
 
The most I have ever done is go out running errands while wearing female jeans. Not the boyfriend style, but no chance of mistaking them for guy jeans. I live in a smaller town now, and though your mostly OK if you are gay, trans might not be as welcome.
 
The first time I went out dressed was at night I took some books back to the library. My heart was going a thousand beats a minute because I was sure neighbors would see and know it was me. It was thrilling thought. I love the clicking sound my heels made on the side walk. It was a fabulous feeling and I loved it.
 
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