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.
 

Huggies4me

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i use to walk around my house dressed as a baby girl, i walked up to the window one day as i thought it was quiet outside but their was a women walking by that was at that time in between the middle of the window that has a pillar. as i walked to the window i saw her and she was looking straight into the house wearing dark sunglasses. so i just stood their looking out then walked back. pity i didn`t know she was going into a neighbours house. thankfully they women living their knew i was a adult baby but her partner didn`t.

Also stood at my backdoor in a T-shirt and Nursery plastic panties with a thick nappy under and frilly socks. while talking to said neighbour, first time she had seen me and acted as if nothing was different.
 

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bidl

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I had a daddy who dressed me up in a pink diaper and then a pink onesie and then a pink dress over the top so I was his baby girl
 

DiaperWolf69

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The first time I was seen was the first time I did it, my girlfriend convinced me to wear her undies, I was hooked, so was she
 

Luvsnappies

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There used to be a fetish wear shop where I lived in Connecticut. I went there one day, when I was wearing a Bambino under my regular clothes. I was looking at the baby dresses they had, and the clerk asked me if I wanted to try something pretty on. He held out a frilly pink dress with sooooo many ruffles! My face must have turned so red, but I took it from him and went into the dressing room. It only had a curtain, and I decided impulsively not to close it all the way. I put the dress on, as well as a pretty rhumba diaper cover, and when I turned around, there were 2 customers watching me. The clerk came in and said that I looked so pretty. He let me wear it while I continued browsing the store. Eventually, I was able to relax and enjoy being pretty in front of people, it was such a nice feeling!
 
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