I remember sneaking into my mother's closet and trying on her shoes when I was 4 or 5 years old. I didn't have any sisters, so my access to clothes were limited to what was in my mothers closet. When I was 13 or 14 my mother's youngest sister passed away (she was only 9 or 10 years older than me) and my mother ended up with all her clothes which were stored in our basement. Since my aunt was a "lady of the evening", she had a lot of really cute and sexy clothes. I was in heaven for a couple years until I outgrew everything.

i remember sometime around 12 or so sneaking into my mothers room when i was alone and going through her things. at first i liked touching her silky panties or satin slips then i started undressing and trying them on. i had a sister 2 years older but my mother had nicer prettier things. i remember watching myself in her full length undress my boy things and watch myself put on her things. after i had them on i would fantasize.

i was in my teens, i would steal my mom ans sisters panties from the hamper and wear them.

When I was about 14 I tried on a pair of my mothers tights and found out that I liked wearing them I'm so the first chance I got I bought my self some school girl tights which I found out I liked better than my mothers I'm now 52 and now I wear female clothes around the house most of the time

Sorry, meant it as comment

I was about age 10, found some panties and lingerie that had been left by tennants in the apt. house my grandparents owned, had curiosty to try on some things and it was like an instant hook from then on I preferred soft silky undies, would swipe from clotheslines at night and did everything I could to obtain pretty things to enhance my feminine feelings

I was 10 years old when I had to wear a pair of tights for a school play. This was the first time I'd ever had to wear a pair of tights and I dreaded the thought, but when I put them on I realised how nice and cosey they felt on me. It was a secret I kept to myself as after this I'd sneek into my Mum's room when she wasn't about and try wear a pair of her tights. Now at the age of 40 I still wear tights reguarly, for support wear and comfort, and also for warmth in the winter.

Maybe 6 or 7? I remember visiting a friend of my sister's and trying on her tights and nightgown, then running around the apartment building wearing that. It was a lot of fun.

I am a masculine straight businessman in my 50's in my teens I got this out of nowhere idea to get naked and put on my moms sexy panties...I loved it and still do and very accepting of it...I LOVE being a man who wears very sexy panties...

My First time was with my cousin. I was staying with her one summer when i was 13 and i mentioned that i liked her outfit. She said that it would be fun if i put on one of her outfits. I agreed because her clothes were cute and we were the same size. She came back with a Yellow dress, a pair of tights and a pair of heels. I put them on and i loved the look and feel. The next day we were going to Disneyland and i put that outfit on again. My Aunt and Uncle asked what i was doing and i said i lost a bet to my cousin and they said OK and spent the entire day in a Dress, tights and sneakers(8 hours in heels wouldnt have been good). My Favorite moment was her wedding. She got married and asked me to be her "Maid" of Honor. She never really had girlfriends because she was homeschooled and we were very close. I was honored when she asked me and accepted. While the girls were getting fitted for there dress i was getting fitted for a tux. She left for a minute and i mentioned to the rest of her girls that i was going to wear the same dress as them. I thought that wearing a white tux(her decision) would take peoples attention off her and on me. I had been wearing womens clothes on a regular basis for a couple years and everyone was used to it. I figured that if i wore a tux that would surprise more people and take there attention away from her. Since this was HER wedding day, the focus was supposed to be on her. So while she was gone i got fitted for my magenta gown(god awful but it was what the girls were wearing). I showed up that day in the tux as the dress was a surprise.Shortly before i needed to be in line i ran into the bathroom and changed into my Magenta gown, suntan pantyhose and red heels. Everyones eyes were on her and nobody even noticed i was in a gown. I made the right decision and she had an amazing day.