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Crossdressing Awakening

The first time that I recall having an interest in crossdressing was when I was about 10 years old. It was Halloween time and there was a costume parade at school. For the life of me, I cannot recall what I wore, but there is one costume that I vividly remember!

There was this one boy who dressed as a girl. He wore a soft pullover sweater and pleated skirt. He had on white anklets and pointy flats. He wore a delicate pearl necklace and had on a pageboy wig. He seemed to be having a lot of fun and I remember he had a cute smile. If you didn't know, you'd think he was a sweet little girl.

I guess I had a schoolboy crush on him. Even though it was years before puberty for me, I remember having this "funny" feeling inside when I saw him. Kind of an excitement and thrill that I'd never experienced before. I was not one of those boys who "hated" girls. In fact, I had several female friends. But I found myself strangely attracted to this boy because of what he was wearing.

It is only looking back now that I realize that this was my first introduction to crossdressing and the feelings of excitement that it aroused in me.
jennyla73 jennyla73 36-40, F 11 Responses Mar 25, 2012

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OMG...what a dreamy, ultra erotic story...I also had my first "cute girly boy" crushes as well...can we chat about this sometime and exchange private?

I must have been about 13. My stepmother used to leave the clothes in my big bedroom to be ironed. I used to try her frilly panties. I got so turned on. I used to imagine I was a girl.. It was great.. still do it, nearly 50 years later!
I wear stay-up stockings and panties or a thong. I've started to like thongs, because they kind of stick in between your legs and further up behind and you can feel it all the time. I understand that it must stimulate women who wear them, because they do the same to me and make me aware of my sexuality, perhaps more so than if wore just regular panties.

Nice story!

interesting read. did you ever end up pursuing a potential date with him?

Wonderful story. Thank you ;)

Fabulous sweetie

<p>Its funny how some of those early experiences helped shape who we are today. I had a similar experience but from the other side of the fence. I was around 8 or 9 during one of my first public outings in full female attire with my mother and sister. We were shopping, and although I had not completely accepted the role in my new feminine persona, I remember being watched by another boy only slightly older than myself. Something in his smile told me that he saw me only as a girl and it left in my stomach the same 'funny" feeling. I'll never forget that first time ...or how much I learned to love being smiled at by others through the years. It was my not first introduction to crossdressing, but it was my first memorable experience being seen and admired as a girl by another boy.</p>

Same her for some reason I had crushes on some boys when I was in school before puberty

I also remember doing other boys in school that at Halloween time would dress up as a girl and I always wanted to and only did it once but never had the nerve to go all out with make up the while nine yards. I was so stupid.

I could never pass as a woman, but how I envy those of you that go out in dresses and skirts. In MY town, if I was seen outside in a skirt, it would damn near make the local paper. At least 1 in 20 men crossdress, and in THIS town, they all hide it so well................stuck up ******* haha

It is a lot of fun dressing up.<br />
I wonder what that cute boy is doing now?<br />
My first Halloween dressed as a woman was the last one and wow, I had so much fun and I had lots of females fussing over me and that I wished it would go on forever and sadly the night ended to soon for me.<br />
There is always another time to dress up and I have dressed up and gone public lots to dances and discos and even shopping as a woman.<br />
there is always the next time to look forward to.<br />
So much fun.