First time being seen in girls clothing

[mistysummers]

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

 

[BabyFee]

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

I can’t say for sure that I have been (it is largely an in house thing), though I can’t imagine my neighbours haven’t seen me frolicking about in the garden in my Stepford style floral dress.

 

[LonelyFOX]

One of the granddaughters of the lady where I share accommodations saw me wearing women's ripped jeans and block heel rhinestone sandals told me that I look so sexy and tall than in ordinary jeans and sneakers!.

 

[mistysummers]

Wow seem there are a lot of people who have never been seen by another person, ok then lets expand on this, uploading a photo to the Internet, ie facebook or a forum. What were you wearing and did people comment

 

[oleman72]

This is some of my out and about clothes I wear everyday. All female

 

[chrischrischris]

Got caught out today opened my bedroom window 2 people standing outside omg
Saw me dressed as a girl they laughed and walked off

 

[mistysummers]

Got caught out today opened my bedroom window 2 people standing outside omg
Saw me dressed as a girl they laughed and walked off

Should of owned the situation and smiled and waved

 

[LonelyFOX]

Today I went to the drugstore wearing plain white T shirt, ripped jeans and my slingback peep toe flats.
My feet don't get so sweaty with these!.

 

[BoyLuc]

I was at a bath house that has very nice rooms outdoor pool and is really nice in spring at night.... I had put on a pair of no line black stretchy panties that fit perfectly and hold "things" together. I had just gotten there and a guy I have known for awhile (he's from LA but family in town so here alot) and very casually dated (met him there) saw me and his eyes lite up. I was momentarily spooked because I had no intention of being seen in them or certainly leaving the room in them. I was just enjoying them in private and got brave enough to hang by the door staring out the window in the hall.

I have a very slim/athletic build (helps me look very much younger than my chronological age). Panties (and women's jeans) actually fit me better than most men's stuff as long as they are stretchy. Well, he told me how hot they were on me and I pretended they were just tight men's briefs... they don't have lace. He knew better and dragged me to my bed and we spent the night together once again. He had me try on a few others I had with me.... Women like them on me too... I won't argue

Always had an underwear fetish finding men's bikinis in smaller and smaller profile but panties are more recent... after, on request, getting some for a lover about 3 years ago. He wasn't brave enough. I just pretend (in my head) that I'm shopping for a gf or wife. I tried some one I had gotten for him and was like wow, these are very hot... I discovered Ross has racks of panties for cheap so I can try different kinds on at home and not have to return them if they are not quite right. One time a cashier told me how much he liked my selection and asked for my number. I wasn't one bit embarrassed after both these situations.

 

[PlinkinginPink]

My first time being seen by people was when I moved out of the house and into the city of San Antonio.
I knew I was far enough away from my old life.
So I threw on one of my skirts, knee-high socks and went to the mall.
Nobody looked twice at me, it was a massive boost to my self confidence to the point that I started finally dating.

 

[Seasonedcitizen]

Years ago I used to go out crossdressed. One day before Halloween I went out and didn't notice a neighbor walking her dog because of a tree in front of my house. I said I was going to a Halloween themed office party. She and her family moved away so I don't have to worry about that.

 

[GoodniteLover219]

The first time some acquaintances found me in crossdrsss attire was when I went to my first Anime convention back in 2014.

I remembered sharing my interest in Cosplaying for the first time and shared my feels for wanting to dress as girl characters for the first time.

I recalled at least a few who knew of my interest and did ended up finding me. I got good compliments and sense then Crossplaying has never left me.

 

[Peesalot]

I discovered Ross has racks of panties for cheap so I can try different kinds on at home and not have to return them if they are not quite right.

OMG!! We have a Ross near us that I've never stepped foot in. It's next to a LOWE'S. I can see my next shopping trip to LOWE'S will involve looking thru the panties at Ross. We are new to the area and I expect the odds of actually seeing someone that knows me would be in the 10,000,000 to 1 range. That means I can take my time looking to find something I'll really like.

 

[Inconjr]

Years ago I went out one time wearing a womens sweat pants set with matching sweater, red womens slouch socks and payless womens sneakers in white and purple.

 

[Inconjr]

It was very comfortable and cozy

 

[Onesieman]

When I first put on the Disney themed two piece swimwear at 13, my dad caught me, and he just laughed. Luckily we didn't have internet back then, or he might have posted me wearing a girls bikini online. He didn't even think to take a picture.

 

[BoyLuc]

OMG!! We have a Ross near us that I've never stepped foot in. It's next to a LOWE'S. I can see my next shopping trip to LOWE'S will involve looking thru the panties at Ross. We are new to the area and I expect the odds of actually seeing someone that knows me would be in the 10,000,000 to 1 range. That means I can take my time looking to find something I'll really like.

I usually look at men's1st and carry a few in the basket/cart and then shop the female racks. Keeps anyone watching guessing. But honestly, women's fit me better . I "act in my head as if shopping for gf/wife who just happens to be same size... which I have and do sometimes.... unless there is someone showing interest and I might show it's for me. A very cute and nice cashier hit on me once. He was very sweet. Said they would look great on me and I got all the good ones .

 

[Peesalot]

I usually look at men's1st and carry a few in the basket/cart and then shop the female racks. Keeps anyone watching guessing. But honestly, women's fit me better . I "act in my head as if shopping for gf/wife who just happens to be same size... which I have and do sometimes.... unless there is someone showing interest and I might show it's for me. A very cute and nice cashier hit on me once. He was very sweet. Said they would look great on me and I got all the good ones .

I wouldn't have any interest in looking at the men's underwear. I'd just look thru their selection of panties at my leisure. If any clerk asked if they could help me, I think I'd decline; but, if they pressed the issue, I'd tell them I'm looking for a certain size of lace panties that I think I'd enjoy wearing. After they picked their jaw up off the floor, they might help me or they might not.