How it all started..

My older sis first dressed me at 5.  After that, it was my desire to be 'her' again.  I liked how I looked and felt and it never seemed wrong to dress even if we weren't playing with the Barbies.

PaulaF

Started by trying out some of my sister's clothes that were kept in the storeroom (I would often sneak in when everyone was asleep and put them on). She's only a year younger, so our size difference isn't that big.

Besides mom’s undies I had an older sister whose were frankly much nicer. Later a girl cousin who lived next door.

Mine was for Halloween with the full dress heels makeup wig and even shave legs have to have the smooth legs and haven’t looked back since

hugs kim🦄

It’s difficult to believe, but 51 years ago, something drew me to look and rummage through mom’s lingerie drawers. Home alone, possibly a bit bored, I wanted to see what I looked like if I were a girl. Got panties on with no problem, bra(which was way too big) awkwardly on, and finally, some lipstick. What I saw in the mirror was transformative. I was pretty. What was actually in the mirror may not have been that pretty. But, it was a magical experience, and I haven’t stopped since.

Kay👩🏻‍🦳👄

Hello Jenny, Yes like most of us girls it started with mums clothes [had no sisters] then when I started work I could buy my own clothes. It was better to be able to choose what clothes you wanted then borrowing you mums. I did wear some of my cousins clothes when I was a teen, but only for a little time. love Helenmarie

There is no poll answer for me here, I was a late starter. I was in my 50s and loved wearing thongs. My late wife actually liked me wearing thongs. Anyway, as they were wearing out, I needed to get more but the only ones available to me were so awful looking, mostly black with beer ads or football (soccer) teams on them that I got a bit disheartened over finding any nice looking ones. Of course, the womens racks were full of beautiful thongs & strings, so I asked wifey if she minded me trying a womens thong. That was the start of my dressing and, 20 years later, I rarely wear "mens" clothes.

Interesting.....

Older sister's for me as well. Saw some baby blue nylon panties she had left in our shared bathroom and had an incredible urge to try them on. Sliding then up my legs and into place was indescribably exciting. I knew then that this was not just going to be a one-time experiment. From then on, I borrowed her panties, bras, nylons, and baby doll nighties when ever I had the house to myself. It felt so thrilling in those articles of clothing. Once old enough, I started purchasing my own as I know it was not right borrowing her things without her permission.

It is true Emily that it would be better to ask but a little awkward to ask your teen sister if you can borrow her panties. At first it was a bit of a thrill in addition to other feelings knowing you were wearing panties that had been on a gg.

Hi Jeannie - Yes, the thrill was what kept me coming back time and again. My sister and I were pretty close (at least as close as an eleven year old boy and a 13 year old girl can be). If I could have gotten passed the embarrassment of asking, I actually think she would have been accepting of it and given me a few pairs of her older panties to wear so I would not need to borrow the ones she was actively wearing.

I started at age 8 when I put on some of my Mom's red lipstick. Shortly after that I tried on one of her bras. From there I went all the way, lingerie, dresses, shoes, wig makeup, and bling. I still love red lipstick to this day!

Hi Jenni Sisters clothes, moms make up for me. I took every opportunity available to present as girl Halloween, school plays. I wished someone recognized the real me back then, I would not be dealing with this now.

Luv Stephanie

I think my sister would have been cool with it as well but I too never had the nerve to find out. Amazing to think I buy panties in stores in drab and have been able to do so many years. I have even been able to talk with sales ladies about bra sizes and get tips. Happy lingerie Emily😊💋