I'm Sorry!

It was my first pair of stillettos. I was in my teens and living at my parents in a small village. I had worn them around the house and loved them indoors, but I desperatly wanted to go out in them. I love the feeling of going somewhere in heels.

 I waited for a weekend when my folks and my brother were away. I slipped on my new 4 inch stiletto heeled, black leather, zip up, knee high boots. I wore them around the house all day with my tiny tiny little leather skirt. When I thought it was late enough so that everyone in the village was asleep, I went out.

I had changed into jeans, but slill had my gorgeous new boots on underneath. I walked right through the village to the other side and came back a different way, about 1mile walk. It was as much as I dared and as much as I could take, my legs were killing me.

The following day I was hanging out near the village shop with friends. One of the women from the village walked past, who we all thought was a bit crazy. She spotted me and asked strait out

"Have you got a sister"

I had to say no, coz I havn't. She said

"I thought not. So that was you then, late last night, walking past my house in high heels"

Some how, I laughed it off. We all laughed and jeered at her. She never spoke to any of us again, but she was right, and she knew it.

I'm sorry for the way we treated her that day and for weeks, maybe months after.


Looking back, if I had been caught and uncovered then, I could be in a very diferent place right now.

I might even be truly deeply happy!



Heellover Heellover
36-40, M
9 Responses Dec 2, 2009

Oh so sad hun, just have faith in yourself, im sure they are not too far away ifya look.

Missed opportunity

*sighs* Yeah :-(

No despair ....many such opportunities come and mine have turned me into...,,,well me lol

I enjoyed your story! Fun stuff!

Thank you. X

Hopefully you've kept your interest in heels and continue to wear them, as I have all these years. Some people won't accept a male in heels, but that's just life. Some won't accept you based on your skin colour, your religion or your economic status. They don't matter. Live your life the way you wish as long as it doesn't harm others, and be happy.

Yes, I'm still in heels. X

I simply love the way heels feel and the way they make you walk. I love the way they have of making even my legs look sexy. They are one of the most fem thing sever invented.

If I saw her today I think I would try to explain, but she might not remember, it was about 20 years ago.<br />
You should go out for a walk. It is so much better than being stuck indoors. Even if it's a pair of low heels under mens long pants or jeans. Then all anyone else can see is a man going for a walk. Just so that you know you are wearing them is enough.

She found out by mistake about 2 years ago. She's not too keen on the idea.

nice story. I have worn heels and it is a wonderful feeling. so sexy! I have not been caught, but I have come awful close at times!! Does your wife know?

I was caught in more than heels. I was caught in my mothers best sexy dress and heels and everything else from her draws, knickers, stockings, bras , dresses and heels everywhere by my mother.<br />
This was when I was about 13 or so and her size and I wished her room and everything in it was mine. In a way I wished I was her.<br />
In a way I am her. I am half of her or even more. I have her legs, hair and eyes and I prayed to god every night to wake up a female. Perhaps nature made a mistake with me.<br />
I first wore girls clothes when I was about 7 and loved it ever since.<br />
Since I have no sisters, I waited until I was big enough to be her size and when that time came. I was in heaven. I love my mother and wearing her clothes made me even closer to her. I had her smell on me when wearing her clothes. <br />
When I dress, I dress. not a thread of male clothes at all. All female for me. <br />
She later supported me in my choice of clothes. She thought I did her clothes justice.