Anyone encouraged to dress when young by a another boy?

[Belfast Bill]

I had a friend who played around with a whole gang of us, playing soccer in the street, and the usual boy games, but on occasion I would go to his house and we would make model aeroplanes together etc.
I will never forgot him taking me up to his bedroom, and he got me to sit on the bed and he went off into his sisters room, and put on her stockings, high heels, a slip, and some lipstick, and he paraded up and down while I was his audience.
I was surprised, excited, though I did not know either why or what to do with it at the time.
We did this a number of times together, and he would model various outfits that his sister had and I would make comments and say how nice this or that looked on him.
It was our secret for years, and whenever he said, "want to come to my house after school today" we both knew what it meant, and both knew that he would dress up for me, and I loved it. Wish like hell I knew then what I know now, and we never ever even took a photograph of him, but it would involved a lot of questions being asked getting the film developed.
Anyone have a similiar experience with a friend?

[renneeists]

when I was young (13?)
The boy next door(14), had his dads girly mags in his room, eventually he got some of his moms bras, and we took turns wearing them and playing with each others boobs.
Eventually it progressed a little more, but then he wanted more then I was comfy with. I found out later he was doing an older guy (20?) for money and I wouldn't see him again after that.
I don't think it was jealousy, I was just uncomfy with what he wanted.
I still enjoy the bras, and now the other clothes.
While I'd love to be caressed again I still don't think I'd feel right about anything more.

But then again noone but my ex ever wanted sex with me dressed--who knows

[Loni]

NO, i am a self made woman.:heehee:

[linnea]

I had very little explicit encouragement from anyone.

[NathalieX66]

I was about 7, and hanging with about 4 or 5 boys on my street, all approximately my age, and we went into one of the boys' parents' garage and discovered his sisters's frilly ballerina leotard/tutu amongst some boxes of stuff. This was pretty difficult for boys our age to ignore. One is either curious, or averse to it.....we were all the former. So we all took turns to try it on. For me, wearing it was not a revelation, but more of an affirmation.

[sherryR]

next door with a friend, trying on his older sisters wounderful things. as he was slightly larger and i fit them just perfect, i eventually was able to model almost everything she owned for him

[JTWoods40]

From the day I was born till I was almost 2, my parents dressed me as a girl. Of course they thought they were having a girl so they bought and were given all girl clothes, bedding, toys and things. As I grew, they slowly got boy things but for some reason I was always drawn to frilly Lacey clothes and things. There is much more to tell of those early years growing up. Many stories to tell. But when I visited my cousins, they loved dressing me up as their little sister cousin. I loved it to. An for many years growing up and still today I love to dress in comfy girly skirts and dresses. But I do miss having someone to dress up with/for.

[Jason+]

When I was 13 I found a house that had been abandoned with a lot of clothes and things left behind. I showed it to a friend and told him I wanted us to go and try some of the things on that I had found there. He looked at me like I had grown a third eye out of my forehead and made it clear he wanted nothing to do with it. That made it pretty clear to me that it would be a private thing, at least before this site and another I used to visit.

[Christina2008]

Wow, I missed out when I was young. Nothing even close happened to me like that.

Nice story. Kids do the funniest of things.

I wonder if he’s still dressing.

[CharleneT]

No, nothing like that at all ... but you have to understand I was a military brat and Catholic; definitely had to keep my interests so far under my hat that only the worms in the ground could find out !

[NicoleScott]

When I was about 10, two other boys and I went to the basement for the stated purpose of painting our faces like clowns. We had some really red lipstick. One boy drew red circles on his cheeks. The other boy and I painted our lips, not like a clown but like a woman. Nothing was said about why we did this or any inner desires, we just applied lipstick to our lips. That was the end of it. Nothing was ever said about it again. I can't help but wonder if I may have had a potential dressup partner if one of us had pursued conversation about it. I know why I painted my lips (I've always had a lipstick fetish), so I can imagine that he may have done it for the same reason.

[JoanAz]

I was so lucky, there was a Neighbor girl who was just a few years older than me. We would go to the movies and come home and DRESS the parts.
Andrew sisters, and many other female parts, I was probably 5 or 6 and we were just kids palying parts..
Our Parents knew and never said anything..
Years later my Parents found out about my dressing in womens clothing as a teenager, we had disiplinary talks but never harsh action against me...
My parents were verry understanding, Mom was in the fashion industry in NY.
:hugs:

[sometimes_miss]

Errrrr, yeah. It was a much older boy that dressed me up as a girl, and convinced me I was supposed to be one, and then he would have sex with me. I guess that sort of counts.

[Sarah Doepner]

For a couple of days as a young teen I engaged in a bit of fantasy play with my best buddy. We had found an apron that would magically change the wearers gender. He was a bit more adventurous and sexual aware than I and he got me to wear the apron more often than not. We had some strange interaction but it never got to the point of sexual play, but it may have paved the way for him to move on to real girls and for me to move on to more girl clothing.

Maybe one of these days, if I see him, I'll ask if he remembers those afternoons oh so long ago.

[Shananigans]

My SO's brother is a CDer. He said that when they were young, his brother would put on some of their mom's clothes.

However, he said that he had thought about it before his brother started doing it.

lol maybe he just wants it to be his idea.