First time being seen in girls clothing

LonelyFOX

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When I went with my girlfriend to a place where there are night dresses and wedding dresses for sale, then she saw the rack of all the stiletto sandals and peep toe pumps.
We took off the shoes when entering to the store.
She tried on a pair of silver rhinestone sandals and then she asked for another pair of golden stiletto sandals, the Chinese lady who attended her brought them to me and then my girlfriend took me off my socks and she asked me to try them on. She paid for the two pairs of high heel sandals and we came back to home in heels!.
 

TheMatrixIsComing

Don't forget the turkeys! They deserve love too!
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First time I wore girls clothes would be not really clothes but I wore my mom's fingernail polish at around 6 years old to school one day.
 

Punished34

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My mom has called me out a couple times for having a bra on but I’ve been too nervous to go out in a full outfit. I have leggings and a blouse on now. Really wish I could just go out and be me in them
 

ABAlex2

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First time being seen as an adult like that was my gf, and I was wearing a tutu she bought. I've never been anywhere in public like that
 

JUSTONEBABY

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Ok so after i made the thread about what was the first clothing you worn from the opposite gender, i got the idea to ask what were you wearing the frist time someone saw you crossdressing.
I think most people will say a family member saw me wearing ******, which you can say but if you were also seen by a non family member, list that as well.

For me it was when i was with my friend at her house when we were 14. We didnt plan on swimming in her pool, the idea just came up, the problem was i didnt have anything to swim in, my friend did offer me some shorts to wear but as a joke she did offer me an old 1 peice swim suit she wore back when she was 10 and had Disney princess on it. I joked that would wear it but what i think happened is we both joked about it that it was kinda like a double bluff and it would have only taken 1 of us to call the bluff and i would have just worn the shorts, but i spent the day in a Disney princess swimsuit, which i remember fitting rather well for somthing made for a 10 year old
That’s sooooooooo cool 🥰
 

Kittyinpink

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I have been caught a few times. Most memorable for me
Had a few beers . Got chatting to a guy well into his tattoos. I have one ,a pretty tribal style design curling just beneath my waistline And top thigh. He asked to see it and I pulled my (female corduroy trouser) down just enough to decently display my tattoo. Oops!! I forgot I was wearing cute pastel bikini panties!! He didn't talk to me after that!!
 

Babyspace1947

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The first time anyone saw me in women’s clothing was shortly after I joined the military. At the time I was living in the dorms and my friend and I were drinking and watching TV with his girlfriend and another girl. Anyway, the girls got this idea to dress us up as women. I was secretly in heaven. They did the whole get up....make-up, wigs and clothes. It was so hard to hide my excitement.
 
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