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The First Time Someone Saw Me Dressed

March 5, 2012

It did not take long in my crossdressing before it was mostly about pantyhose.  I loved the look and feel of the product.  I might try on other clothes, but only if pantyhose were part of what I tried on.  Perhaps that makes this more of a fetish.  I do not know.  However, a new aspect started to emerge.  I was starting to get a thrill simply from wearing girls’ clothes no matter what fabric they were made of.

I think I was doing this because, to me, crossdressing seems to fuel itself.  After I started crossdressing, I started wanting to wear more clothes than just hosiery and slips.  When I would get the opportunity, I would put on a full outfit of my sister’s or my mom’s clothes.  I remember celebrating internally when I was wearing nothing but women’s wear.  I do not know why, but it seemed like an achievement.  This occurred during the 80’s when women dressed more feminine than today.  I did not thrill myself in dressing femininely, but it was something big when I wore my first dress, or when I wore that first pair of white pantyhose or maybe heels.

Crossdressing seems to push you to try something new, much like dating does.  The first time I held a girl’s hand, it was exciting.  But then it became commonplace.  Then, I started wanting to kiss her.  The first kiss was very exciting.  Yet, it too became commonplace.  Likewise, crossdressing was always nice, but doing something new would get into my head and I would start wanting to try it.  Eventually, I got the idea to wear clothes around someone else.  Around my grandmother.

My grandmother came to live with us for a while.  With someone to watch me, my parents did not have to take me with them wherever they went.  They would leave me alone with my grandmother.  I thought, since grandma had bad vision due to cataracts, I might be able to wear some plain women’s wear and she wouldn’t notice.  I put on mom’s shirt and shorts with some pantyhose and shoes.  The pantyhose were darker than my skin tone, but I did not think that they were too unnatural.

I left the room, put on the outfit, and returned.  Grandma got a look at me and said, “What are you wearing?”  I played it off like nothing was unusual.  I did something in the kitchen.  She was sitting in the other room leaning over so that she could look into the kitchen.  Eventually, I walked over to her and sat down by her.  I was wearing nothing but women’s clothes!  She leaned over and looked hard at my legs.  I covered them up with a blanket.  I was not as hard to see as I feared!  After a few minutes, I got up, left the room.  I changed back into my clothes.  She never said anything more about it.  I do not think that she ever knew what she saw.  That was my first outing.

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From → True Stories

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