Skirt. A jones New York suit skirt in navy blue.


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I dont remember the first piece I bought... I do remember driving an hour away from my town late at night to shop walmart where there was no chance of running into anyone I knew. I filled a cart that night... I didnt want to try and only had a rough idea on size from the batch I mention here in a moment...so I kinda guessed... I also didnt want to spend much time looking... I just sort of tossed things in my cart and proceeded to check out sweating nervously.

The first batch of clothes I got was a absolute godsend... literally. Its a unbelievable story. I lived in Colo Spgs and was out on a sunday afternoon, the neighborhoods were those with one way in and out and branch after branch of streets circling about... I ended up in one by sheer accident. It was trash day and I, being a car person... I noticed a set of corvette rally wheels by the curb. Now these wheels are rare being 8 inches wide and I knew they had value so I pulled up to throw them in my car. I saw 2 large trash bags of clothes and I just instinctively grabbed them... I got home and was in heaven... they were clean, nice and nearly everything fit. That was a gift from the universe right there, instant wardrobe. There was everything in there... someone mustve lost weight or croaked or left someone...

I bought panties sometime around age 17 or 18 at Target i believe. Other than underwear, the first thing was a pair of women's Levis jeans around age 20.

good god that was 40 plus years ago.... have a hard time remembering what I did last week.........

A cute black dress. My ex had the same I was jaleous so after we broke I bought It but different color

i really dont remember, i think it was a pair of skinny jeans. but recently i bought my first set of bras for the first time ever so I guess that counts. 

but honestly, WHY THE HECK ARE BRAS SO DAMN EXPENSIVE?!? I AM CRYING.

Quote from: RitaChans on February 07, 2016, 03:29:38 PM
I dont remember the first piece I bought... I do remember driving an hour away from my town late at night to shop walmart where there was no chance of running into anyone I knew. I filled a cart that night... I didnt want to try and only had a rough idea on size from the batch I mention here in a moment...so I kinda guessed... I also didnt want to spend much time looking... I just sort of tossed things in my cart and proceeded to check out sweating nervously.

The first batch of clothes I got was a absolute godsend... literally. Its a unbelievable story. I lived in Colo Spgs and was out on a sunday afternoon, the neighborhoods were those with one way in and out and branch after branch of streets circling about... I ended up in one by sheer accident. It was trash day and I, being a car person... I noticed a set of corvette rally wheels by the curb. Now these wheels are rare being 8 inches wide and I knew they had value so I pulled up to throw them in my car. I saw 2 large trash bags of clothes and I just instinctively grabbed them... I got home and was in heaven... they were clean, nice and nearly everything fit. That was a gift from the universe right there, instant wardrobe. There was everything in there... someone mustve lost weight or croaked or left someone...

lol....I completely understand not wanting to be seen. I live daily as a masculine man, & I'm not sure I'm ready for people to see me as anything less than that right now. I normally thrift on the weekends to find stuff to buy and sell, which is how I earn extra cash. One of the local thrift stores has tons of name brand clothes that you have to sort through yourself, & that's how I'm planning to stock my closet with women's clothing. I always find tons of cute women's name brand stuff (Under Armour, Nike Dri Fit, etc), though most of the time it doesn't fit (I was beefy as a guy, so now I guess you could call me a plus size woman). I found an under armor sports bra that was really small, & I found the 2 skirts I purchased yesterday. I guess I'm going to have to buy some things online, considering larger women's stuff is hard to find. It's much easier for me to be discreet buying stuff there, rather than try to pick through clothes on a rack in the women's section of a store.

Quote from: Adchop on February 07, 2016, 06:37:21 PM
lol....I completely understand not wanting to be seen. I live daily as a masculine man, & I'm not sure I'm ready for people to see me as anything less than that right now. I normally thrift on the weekends to find stuff to buy and sell, which is how I earn extra cash. One of the local thrift stores has tons of name brand clothes that you have to sort through yourself, & that's how I'm planning to stock my closet with women's clothing. I always find tons of cute women's name brand stuff (Under Armour, Nike Dri Fit, etc), though most of the time it doesn't fit (I was beefy as a guy, so now I guess you could call me a plus size woman). I found an under armor sports bra that was really small, & I found the 2 skirts I purchased yesterday. I guess I'm going to have to buy some things online, considering larger women's stuff is hard to find. It's much easier for me to be discreet buying stuff there, rather than try to pick through clothes on a rack in the women's section of a store.

As a plus size myself, I feel ya.... our thrifts have lots of plus size

Other than women's underwear, my first item was a grey sweater dress.

For me it was a denim pencil skirt I ordered online. I didn't convert from men's to women's sizes properly so it ended up being about 3 sizes too big. I was too embarrassed to return it for smaller so I used a bunch of safety pins to gather the waist in in the back. This had the effect of basically turning it into an A-line.

Quote from: RitaChans on February 07, 2016, 03:29:38 PM
I dont remember the first piece I bought... I do remember driving an hour away from my town late at night to shop walmart where there was no chance of running into anyone I knew. I filled a cart that night... I didnt want to try and only had a rough idea on size from the batch I mention here in a moment...so I kinda guessed... I also didnt want to spend much time looking... I just sort of tossed things in my cart and proceeded to check out sweating nervously.

The first batch of clothes I got was a absolute godsend... literally. Its a unbelievable story. I lived in Colo Spgs and was out on a sunday afternoon, the neighborhoods were those with one way in and out and branch after branch of streets circling about... I ended up in one by sheer accident. It was trash day and I, being a car person... I noticed a set of corvette rally wheels by the curb. Now these wheels are rare being 8 inches wide and I knew they had value so I pulled up to throw them in my car. I saw 2 large trash bags of clothes and I just instinctively grabbed them... I got home and was in heaven... they were clean, nice and nearly everything fit. That was a gift from the universe right there, instant wardrobe. There was everything in there... someone mustve lost weight or croaked or left someone...

...or purged 

This question brings back great memories of my childhood and crazy teen years. I grew up with four sisters ahead of me so most everything was hand-me-downs, and whatever my parents deemed appropriate with their money or allowance. Then came my first job and with that -- my first paycheck---  This girl went shopping with no need for parental approvals. I bought a beautiful two piece skirt set. The top was off the shoulders with a deep ruffle in a pseudo tropical print, a matching full gather skirt down to my ankles. I also bought shoes for this skirt set and, to this day, are killer!! 5" pointy toe set off with thin leather bows in bone color.  Got a purse to match.  And yes, 40 years later I still have it. Classics never go out of style. It just meant so much to me that I worked and bought it with my own money.   

Panties. This was before I was out to myself, so I didn't even really think about why I was buying them. I thought maybe it was a fetish thing, but I never really had a panty fetish before or after. I bought them the first weekend I lived alone, put them on, and concluded I looked "so cute".

Surprisingly it took another year for me to figure out what was actually happening.

The first thing I bought was pantyhose.  Bought many pairs since.

Quote from: Tamika Olivia on February 11, 2016, 02:23:15 PM
Surprisingly it took another year for me to figure out what was actually happening.

So happy to hear that.  It took me 27 years to make the same journey.

Quote from: Cindy on February 07, 2016, 03:46:00 AM
Given my age I think it was two fig leaves to cover my chest 

HA!!!!   

I cannot remember for sure the first piece I bought.  Probably VS cotton bikini panties.  Still my fav.

Some ladies boots, leggings and a nice long top with doves on it. Oh and a handbag and purse, but I think that counts as accessories.

A pair of medium heel slippers were the first item I bought, and for a long time I only bought shoes and then the first thing that was not a shoe was a bra and a pair of panties. Since then I have a full wardrobe of women's clothing(but not nearly enough) which I all gathered after I moved away from my parents 5 years ago.

Quote from: Cindy on February 07, 2016, 03:46:00 AM
Given my age I think it was two fig leaves to cover my chest 

   LMAO Cindy. Have you been conspiring with Dena to inject more humor into these forums?

  It just so happens my first purchase was in the same vein as yours. I am pretty sure mine was an Playtex 18 hour bra.
I didn't have anything to fill it with except some socks but I loved the tight feel around my chest.

   Hugs,
    Jeanette

Quote from: JeanetteLW on March 01, 2017, 05:58:57 PM
   LMAO Cindy. Have you been conspiring with Dena to inject more humor into these forums?

Wandering around the moderator area makes one a little crazy sometimes. There is a good reason why you can't see what goes on in there. Just a little preview.