First Time

I started with panties and bought them as soon as I became an adult and especially because I no longer had access to my sisters panties once I moved out. The first time was great the clerk in that section was a middle agreed lady and she smiled and winked to let me know that she was pretty sure the she I was buying for was me. She explained that my “girlfriend “ would really like a certain style and material and tfe reasons why. I thanked her and bought several pairs in that style and material in all of the colors they had.😊

How wonderful, I bet it made you exited.

It did and in she was so nice that had she asked me if they were for me I would have said yes. It gave me the courage and confidence to buy lingerie and ask fir suggestions 😊

Yes...there was a similar question, not long ago...

Me , always going have the same answer...NYLONS. There used to be a Nylon stocking store or Two on the corners of main street, like Conroy's Flowers And Now STARBUCKS.

I went there and bought several pairs for my Sister ( that I didn't have) and my Mom, who would not generally send  a 10 yr old to buy Her Nyl ones!

I loved hers and I figured as delicate as they were, I had better buy my own!

Love to all... Dr.  T.j.

I guess you could say I jumped in feet first.  I had been experimenting with crossdressing by wearing some of my wife's clothes in private but could not squeeze into her shoes.

So, my first purchase was a pair on women's shoes.  3.5" stilettos...probably should have started with a lower heel. 🤣🤣   This was during the COVID lockdown so I bought them online and did curbside pickup at my local Target.  I gotta say, curbside pickup was a dream come true for this nervous CDer.  Once I put those on I knew there was no turning back and started ordering my own outfits.

💖Lola

I'd say the first thing I bought was pantyhose.  After that, it probably wasn't an item of clothing per se, it was a silky nylon material that I used to make my own wrap skirt, using a wrap skirt discarded by my spouse as a pattern.

I began buying my own pantyhose at 13. A sales lady used to help me. She used to tell me the pantyhose I was buying would fit my mother. How did she know my mother? My mother's pantyhose were to small for me. That's why I began buying my own.

At 17, I bought some short girl's shorts, platform wedge heels, bras and a couple of wigs. I would stuff my bra with old pantyhose for breasts. Then I began going out in that attire. It was very scary and an incredible thrill buying my first pantyhose dressed like that. I began buying most of my pantyhose, bras and shoes dressed like that. It often was very scary but always incredibly exciting. I got some looks. I sometimes would get compliments on my legs, shoes and pantyhose. I sometimes got asked of the pantyhose I was buying was what I was wearing as my legs looked so good.

Then at 18 I got my own place and began buying every femme clothing item I ever wanted. Short and sexy dresses, matching bras and panties, stiletto heels, stockings and garter belts, lingerie, everything. I wore them al the time and went out often fun fun and the thrill and excitement of it. One of the greatest thrills was dressing for college parties. i got lots of attention, compliments and got hit on often. Sometimes quite aggressively by both guys and girls.

My first time led to many more times and a lot of scary and exciting outings and adventures.

I think it was either 18 or 19, when I started university.  I received a student loan (i learned it is not free money as you have to pay it back), but being young and stupid I thought I hit the jackpot so I went to kmart on a spending spree.

I bought a one piece swimsuit, aerobic wear (leotard and leggings), a shaper bodysuit, and other girl items.

I can tell you the experience was nerve wracking.  This was the first time I had ever walked into the woman's area by myself, shopping for woman's clothes for myself.  I think I psyched myself out by thinking people are looking at me and wondering why a guy is looking at woman's clothing.

But I was determined.  I bought my items, took it to the cashier, and made up some hokey story about it being a gift.  So she got some gift boxes for me.

Now that I look back, I highly doubt anyone was looking at me browsing the woman's area, and the cashier couldn't careless about my purchases.

I was 12 for my first purchase and it took me forever to get the courage to do it, it seemed.  And nearly as long to save the money to do it, collecting bottles and using my little allowance.  The trainer bra that I had scavenged from the trash when my sister got a real bra was almost worn out, but still fit more or less okay, so I knew the size I needed there and also which size panties to buy also.  I had scouted their locations and prices at the Kmart several times too.

I forged a note 'from my sister' in case anyone questioned what I was up to.  I had the sizes and colors written down in anything but a girls pretty handwriting.  Since I knew where both items were, the entry was easy, but I knew that every lady in the store knew that a perv boy was going into the girls underwear section, which just made me move faster, looking around the whole time.  I found both items easily, like they had been laid out to trap me just touching them, but I got them before anyone could react.  I beelined to the checkout and put them on the counter, along with the note, just in case the woman was checking for a legitimate purchase.  She read it as she rang me up, and I know she was wondering what girl sends her 12 year old brother to buy her undies.

No questions were asked and I grabbed the sack with my trophies and headed for the door, looking for management the whole way and knowing they had set the trap for me as I was going to leave to store so they could embarrass me in public on the sidewalk.

I made it to the bike without incident and almost caught the tires on fire leaving the parking lot so they couldn't catch me.  I never looked back.  I didn't know if anyone was following me, the perv boy, or not.

When I made it home, I was a nervous wreck, and even kept peeking out the curtains to see if they had the police after me or what.

I didn't try on my new treasures for about 2 days as I was so nervous about even getting the sack out from my stash and being caught.

But once I did try them on, both pieces felt wonderful, cool cotton on my bare skin.  I stood in front of my mom's big mirror for I don't know how long, just looking at how I looked with them on, and seeing 'that girl' looking back at me and approving, and I probably kept that smile on my face for days.

The next few purchases were almost as nerve wracking, and I used a different store for each one, so no one could put me in a pattern.  This was Texas in '72, and boys DID NOT mess with girls underwear.  I survived one way or another and had my own small wardrobe which I was happy with.  My first BF took me shopping a couple of years later and I finally saw that I was not a good judge of the right sizes for my body shape and size.  I have no clue how much he spent on me that day, but it was like night and day, from one set of clothes to a proper fit.

PaulaF

It was just last year, the beginning of Covid. A pair of nylon hold ups and a naughty French maid outfit, online. Then panties, lots of panties. Eventually going shopping in person, dressed, but always with my wife.

Bridgette

I was in my early 20s when i first bought my own pantyhose and maybe panties. Things i could hide easy. I was completely closet than won't in to wigs yet. I would just swipe a dress from the wife's closet. I was afraid to swipe her pantyhose because they ran so easy. I was afraid i woukd run a new pair and she would get suspicious. During my single time after my marriage ended i think i bought a skirt or two, again stuff i could stash away and hide easily. I met my now wife in my mid 30s and confessed my desires to her in the first few weeks of our relationship. She gave me a few things of hers a few short weeks later. Then We picked out wigs together. I began buyimg make up, clothes, shoes, bra and panties shortly after that, and eventually breast forms. I have bought everything you can thing of since then. I remwber the first time i bought high heels woth here. She about freaked when i sit down and put them on in the store.

Chelly

First time started buying fem things was when got my first job at age 16 and paycheck bought some pantyhose a bra and some panties.  As years went by started getting more things on and off last 4 years when started my real journey to be a female talking with therapist and DR's This Last year is when decided it was time to go all in to become female.

Donna

In the past there have been many times when I stopped wearing. Yes, I still liked under things, but there wasn't the burning need to wear. But it also doesn't take a good deal to rekindle the flame. I was in my late twenties, married and in the closet. My mother in law had visited and left behind s pair of her panties. I started wearing them and it felt do good that I knew I needed another pair. I went to Sears, walked through the ladies department several times like I was just passing through and i saw the pair i wanted. White Olga's with a wide lacy band and a seam up the back. I made another pass or so, meanwhile, the lovely sales clerk in her mid forties had clocked me. When i hesitated in front of the display, she approached and asked me if I needed assistance. I touched the panties and said that my wife sent me to buy panties (lie). She looked at me with disbelief of course and asked if I knew her size. Why I said the following, I have no idea to this day. I said, she wants them for me, and I blushed as red as can be. The clerk was taken aback a bit by that but was so very sweet about it, she said it was okay and that she helped lots of men and it was nothing to be embarrassed about. She guessed at the size and I left with some of my all time favs.

Hi Gail as a young girl at heart im my early teens i worked lawn mowing and yard cleanup from neighbors to have my own money and used it to purchase my own fem clothing .. As with a younger sister being with me most of the time we would shop and buy the pretty things that i needed to feel like the girl i was at heart ..

Stephanie bass