My first time.  Wow -- that seems so long ago.  In some ways though, I'll never forget it.  I was about 13
years old when I happened to stumble upon my brother, pulling on a pair of women's underwear.  I was so
shocked, I didn't say a word and he didn't notice me at first.  When he finally turned around to head down
the stairs, he saw me.  At first he was embarrassed.  Then he threatened to hurt me if I ever told anyone.
I never did (until now).  A few nights later before, we lay down to go to bed, I asked him why he liked them.
It was more of a question than a criticism.  He decided that I was being curious and that he could trust me, so he told me that he loved the soft silky feel. 

For years before that, I had noticed the girls, and especially the women around me and the soft clothes they often wore.  I figured it was a privilege of their sex and didn't really think about it other than that.  I was envious in some small hidden way, but there was nothing I could do about it.  I was born a boy.

A few weeks later, while my brother was out, I searched his room and found where he kept his pretty things.  Much to my surprise, there were much more than just panties.  He had bras, slips, and lingerie.  I touched each and every one of them, brushing my face and body with them.  That was the last straw -- I was hooked.  There was no denying it anymore.  I wanted to be dressed in soft silky clothes.

Well, my brother came home and got upset that I got into his "stuff".  After he had calmed down, he asked why I was interested in his "stuff".  I admitted I had been curious what they would feel like.  He told me to get my own and leave his stuff alone.  I asked where he got it and he admitted he bought them from a store across town, saying they were for his girlfriend (though I'm sure the saleslady knew better).  As I was only 13, this option was not open to me.  I had been foiled again. 

A few more weeks passed, during which I found myself constantly thinking of getting dressed up.  Then something occurred to me: There were plenty of used clothing stores in the area.  I started scouting them out.  I was determined that I'd feel everything, but I'd only get dressed in the softest, most feminine materials.  I picked a multi layered (3 or maybe 4 layers) petticoat and the rest of the undergarments, as well as a pretty blue dress.

When I found the perfect dress, I had to work up my courage to ask the saleslady how much the petticoats and other garments were.  It didn't make it any easier that the saleslady was in her early thirties and extremely attractive.  When I finally did work up the courage, the saleslady told me it was for young ladies, not boys, and if I was purchasing something as a surprise for my mother I should find out her size (I had selected garments of two different sizes).  I got upset.  I wanted to feel that material.  It was obvious to the saleslady by this point what was going on.  Bless her heart though, when she realized what was going on, she said that "All sales are final, so perhaps you should try the garments on."  She then escorted me back to a large back room off limits to customers where I could change, and even brought me what she estimated were proper fitting garments.  To save me the embarrassment of being caught, she even carried the clothes back herself.  I was so grateful I almost cried. 

When she left me alone, I stripped, naked eager to feel the soft clothing.  When I started getting dressed, it was the most luxurious feeling I had ever felt.  The problem was, I'd gotten on the frilly panties and even managed to put on the petticoats, but I couldn't figure out how a woman got her bra on (never occurred to me that a woman wouldn't put it on the way it was worn).  At about this point the saleslady, Karen, came back to check on me.  She smiled when I told her I couldn't figure out how to get fully dressed.  She told me she was closing the store in about ten minutes and if I didn't mind waiting, she would help me.    

I waited the ten minutes, grateful for the help and eager to complete the transition.  She came back and helped me put on the bra.  Then she showed me how to remove it and put it on by myself, and gave me several other tips on getting dressed.  "I can't be there to help you every time you get dressed." Karen joked.  I told her she was beautiful and sweet and kind.  By this point, she asked if I wanted to complete the look with makeup.  Since she knew my secret, I figured there was no harm at this point.  So I told her yes. 

She left me for a moment to get her makeup case.  When she left, I discovered that I had been so aroused by the
feeling of the clothes that I'd dribbled a little pre-orgasm in my panties.  I quickly changed and Karen came back just as I was changing.  She asked why I changed, and I sheepishly admitted that I'd gotten overly excited.  She reassured me it was ok and asked if she should leave me alone to "finish".  I declined, as I was too eager to see the makeup.

She slowly applied makeup to my face and took care of my rough nails (she didn't do the nails all the way this time).  When I opened my eyes after the final powdering and looked in the mirror, I was astonished.  I was now a young lady.    

She asked me how I thought I was going to sneak these clothes home. I hadn't thought that far ahead.  I asked her what she thought I should do. 

"Why don't you leave them with me?" Karen asked.  I said I wanted to take them home so I could wear them more than just once.  She gave me her address and reassured me that I could come over and dress up (as much or as little as
I pleased) whenever she was home.  It was our "little secret" she said.  

I went over many times in the next few months.  And each time she indulged me.  She even bought me little presents for my birthday.  I was like the little sister she always wanted she once told me.  It was a friendship that lasted until I left for college and even then I'd come back and visit occasionally.  And when I did she'd have me stay the night in the
nighties I always admired of hers...but that's another story...