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First purchase of feminine clothes

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I've never had the desire to dress like a woman in public. However, I do enjoy wearing lingerie and panties/thongs made for men. I do have a fantasy or going in drag to a gat Halloween party!
trione
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first was a light blue lace butterfly thong, couldn't keep everything in but loved that thong
emmcee_M_aussie
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First (and many after) were boring online purchases until I was travelling in Sydney on holiday. It took all my courage but I went to DeBra's - an upmarket lingerie store with a reputation for being open minded to crossdressers. This was 15 years ago. I went in early in the morning and found the store quiet with a few sales ladies. One approached and asked if she could help. I then had to step over the line to ask for a bra. She was brilliant and took me to a corner of the store where they had a range of larger fitting bras and asked me, "Do you want something for support or pretty?" She selected a few when I said pretty and she took me to a changing area. She offered to assist and came in to adjust straps and commented on the fit. All in all, it ended up a lovely experience and I have been in store many times since to purchase bra's and matching panties.
colin123
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Share my wifes, similar size and she doesn't mind.
Guest
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I was lucky, my sister gave me her old dresses and bought me bras and panties
AimeeTison
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My first purchase was a bra and panty set at K-mart. I’m pretty sure it was a soft pink color, satin bikini panties with a matching b-cup front clip bra. My choice of stores has improved and with online shopping the options are limitless.
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I am a married, bisexual male. I've bought my spouse lingerie for years. I began to realize that perhaps I could wear something for the man in my life thinking about how it turned me on when she wore it. So one day I went panty shopping and ended up with fishnet thigh highs in several colors as well as several panties and thongs and even a garter belt. I was out of control! But when we had our next date, I undressed for him and his cock was up before I could even touch it! As far as it being my first purchase, it wasn't too nerve racking as I had made plenty of purchases of this type for her.
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I first started to dress as a girl long before I was a teen.My Mom shopped for me then,I shop for myself now
MaeveKnickers89
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Yep I do indeed. I remember buying a black hobble skirt and navy blue knee-length plated skirt from a crossdressing shop here in Ireland back in the late 1990s. Loved both of them. The black hobble skirt felt fantastic to wear and i got extremely horny wearing it without any knickers at the time. Am hoping to buy another black hobble skirt at some stage online.
browncherrygurl
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I bought my first outfit (skirt, heels top) from goodwill in a guy friend neighborhood
AmberFountaine
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First purchase was feminine, but not exactly clothing - more like an intimate accessory. All of my teenage clothing came from my sister or a friends older sister. Then my sister started getting a semi-annual box of hand-me-downs from my mom's friend that had a daughter that was older and larger than my sister. My sister wasn't at all fond of the idea and would cherry-pick an item or two and let me have anything I wanted and I got excited when that included a couple of training bras. They were big enough to fit me but I had nothing to fill even an A cup bra. My sister said I had to buy some falsies at a nearby dept. store.
I think I stood outside the dept. store for an hour working up the courage to go in and by a set of falsies. I tried to use the excuse that I needed them for a joke and the sales lady began scolding me for wanting to embarrass some young lady and to stop her I admitted I really wanted them for myself and when she didn't believe me, I showed her I was wearing a bra. At that point I think she may have been more embarrassed than me, but I bought them and got out of there in a hurry.
In weeks to come, I became a regular customer of sorts and always visited other areas of the store until I was sure the sales lady I'd met was the one in the lingerie area and she wasn't busy.
jasmine_tgirl
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Quote by viki39cd
'Love pats' panties at Thrifty Drug store. About 13 or 14 years old. Also bought L'eggs a lot back then, too.

Viki

OMG the first panties that were ever bought for me (I was too young to buy them for my self) were Lovepats. Were yours the nylon ones? Mine were. So soft!

jasmine_tgirl
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Quote by AGuyNamedMark
I bought a few pair of panties online but couldn't have them shipped to the house so I had it shipped to Lane Bryant. When they came in i had to go into the store to pick them up. Two weeks ago I wanted to buy a bandeau so I went to the mall to the Torrid store and ordered it. The girl was real nice about the whole thing. Luckily when it came in she was there again to help me. When i picked them up yesterday she asked me if I wanted to look around for anything else. I was a little shy about that so I just said no. Maybe another time.

I'm a transgirl who during my first year of college worked in a thrift store and I could spot crossdressers from a mile away because of how shy some were about looking at clothes. I was always very helpful and even let a few know I was trans (to their astonishment) so they felt more comfortable.

Who knows, maybe that girl who helped you was trans or knows someone who is a crossdresser or trans that they care about.

More likely she just don't mind. It's 2022.

jasmine_tgirl
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Quote by Guest
I was lucky, my sister gave me her old dresses and bought me bras and panties

Same. I didn't buy my first girl clothes until I was 14 but I had been dressing up after school and on weekends from the age of 7. Stuff was either handed down from my sisters or in the case of bras and panties bought by my sister or mom.

XAuthorX
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I like wearing my wife's panties and had never dared buy women's underwear. Then my local supermarket installed self service tills so I can buy stuff without running it past a checkout girl and now with no one seeing what im buying. This means I've been able to buy women's panties for my own use for the first time. I bought a pack of tiny white cotton womens panties.