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First purchase of feminine clothes
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first was a light blue lace butterfly thong, couldn't keep everything in but loved that thong
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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
Share my wifes, similar size and she doesn't mind.
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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.
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.
Rookie Scribe
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.
Rookie Scribe
I bought my first outfit (skirt, heels top) from goodwill in a guy friend neighborhood
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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.
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.
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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!
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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.
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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.
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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.
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Quote by MelanieCD
T-girls and cross dressers what was the first item of feminine attire that you BOUGHT and where?
For me it was a burgundy padded bra and matching thong from Target. It was where I was at when the urge and courage hit me to finally buy something of my own. My guys parts kept falling out of the thong. Finally found a style that holds everything in. I tend to buy a lot from Marshalls, TJMaxx, Burlington Coat, Victoria Secret and DSW and department stores.
I may be in the minority here but my first feminine attire was bought for me: https://www.lushstories.com/forum/lgbtq-community-forum/crossdressing-8?post=4076326
But the first things I bought for myself I was a crop top and denim miniskirt when I was 14. That's when I actually paid for my clothes the first time on a shopping trip with my big sister. Before then I had been on shopping trips with my mom but she always paid.
crossdressing
First let me start by saying I am not a crossdresser I am a transgirl but you asked about Halloween so.... At 6 I said I wanted to be a princess for Halloween. My parents were reluctant but my sister said she'd help me with my hair and makeup before school that day and take me trick or treating with them in the evening. Like I said, my parents were really reluctant, my mom more so than my dad but they agreed to let me. For the entire month of October I was thinking about how I might look and feel . When that day/night night came around it was magical (no pun intended). A few days before we got my costume, a lovely pink and white satin princess dress with a tiara. My sister bought me some matching shoes a little girl's clutch purse and clip on earrings. In another bag were some underthings. A little white nylon slip and a pack of girls panties. She asked me if I wanted to wear that stuff too and I nodded. The clothes and outfit was so soft and so different than my boy clothes and i loved how i felt walking in it with the material caressing my legs. I got up 2 hours early because I was so anxious that I couldn't sleep and I was told to be up an hour earlier than normal. My mom and my sister helped me get dressed then my mom went to work and my sister did my makeup and hair and showed me how to powder my face and reapply lipgloss then that stuff went into the clutch purse and she drove me to school. A lot of kids made fun of me but not everyone, some girls thought i looked really good and didn't know who I was at first thinking i was a new girl in the school. That made me feel really good. They asked me questions about my hair and makeup and I told them my sister helped me. They asked me to sit with them at lunch (normally I sat alone). I felt accepted on some small level as another girl. That night my family took me trick or treating and no one in the neighborhood knew who I was, they thought I might be one of my cousins. After it trick or treating was over, my mom was like "well you had quite a day, let's get you out of that costume" and I asked if I could keep it on and she asked me why since Halloween was over and I said because I felt I was a girl inside and I liked how it felt and I wished I could wear dresses every day. And kind of stunned she just walked out of the room, got my dad and asked me to tell him what I told her. I did and my dad kind of just nodded like he expected this and the two of them walked out of the room before coming back and saying I could keep it on until bedtime. I began wearing those panties under my boy clothes and my parents asked if I'd like to see someone to talk about my feelings. I said yes. The rest is history, I started seeing a child psychologist and she recommended i be allowed to play how i wanted and dress how i wanted at home after school and on weekends or vacation. A year later my room was repainted in all disney princess colors pink and lavender and i got a girl's bed and night stand set. I got clothes handed down from my sisters and some new things my mom bought towards the end of the year. At 12 they realized it wasn't a phase and I started testosterone blockers and we got my name legally changed. I also went to school wearing a dress for the first time since that Halloween. A year or so later I began estrogen hormones and 5 years ago I had surgery. I'm 22 now and in college and no one knows I'm trans.
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Quote by SammiTS
I was in high school and bought some panties at the mall. My heart was beating so fast. I rushed home to put them on and never looked back.
I feel like for us t-girls that first time is like burned into our very being. What were yours like?
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Quote by Guest
junior high school for me.I was already dressing in my sisters things, she told me to get my own so we went to the mall together and she helped me pic somethings out ,bought a cute dress too
What was it like for you? What did you buy? I loved when my sister took me shopping. She had been giving me her old clothes as she's older than me but the first time she took me shopping with her was wonderful as I now was getting my own stuff.
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Quote by Tkdvrman1
Black thigh high stockings black bra and matching thongs used my wife’s mini skirt and blouse and her 4in knee high boots I was sitting st the bar in our house when she walked in that was the first night she pegged my ass
You really need to write this up as a story.
Rookie Scribe
Yes this must become a full on story
Please