Dressed for the occasion

By the time I was 10 years old, my mother thought me too big for a spanking when I misbehaved, and so when she believed discipline was necessary she handed out more mundane (and, in truth, probably more effective) punishments, such as being grounded or the loss of pocket money.

That didn’t mean I didn’t think about corporal punishment anymore, however. Actually, I thought about it a lot, as my collision with puberty was filled with thoughts of being spanked again over my mum’s knee like a little boy.

In particular, I dreamed about being made to put on very feminine, girlie clothing prior to being soundly spanked over my mother’s lap. I imagined having to wear girls’ clothing for an hour or so prior to the spanking, and how it would be a very stark way of making me reflect on why I was soon to get my bottom sharply spanked.

I revelled in the imagined embarrassment and humiliation of wearing a dress, then my mother’s firm hands placing me across her lap. And then the feel of having the back of my dress flipped up and my panties tugged down to reveal my bare bottom for mother’s punishing hand.

After a while, I took this fantasy even further. I had an sister who although two years older than me was about the same size physically. On several occasions when I was ‘home alone’, I sneaked into her bedroom, stripped off my own clothes and dressed myself in hers.

I dared not use her clean clothes for this purpose in case I crumpled or stained them and be found out, so I raided whatever was in her laundry basket. This had an extra dimension for me, though, because sometimes I could smell my sister’s scent on the clothes, particularly her underwear. I would sniff her knickers before I put them on and was thrilled if I caught a whiff of her bum or (especially) her vagina.

When I had finished dressing myself, I would admire myself in the full-length mirror. It would feel so strange and naughty. Finally, I would tell myself that I was a bad boy and needed a spanked bottom. My sister had an oval wooden hairbrush on her bedside table and I would grab hold of this and fling myself face down on her bed.

Then I would turn up my skirt at the back and take down my knickers. My sister had an old blue teddy bear on her bed and I would grab hold of this with one arm and cuddle it close while I spanked my bottom hard with the hairbrush until I was red and sore, imagining it was our mother administering it to me.

Strangely enough, despite this experience being definitely a sexual one, I never actually wanked during this ritual. Fortunately, I was never caught and began to desist once the implications of that happening began to hit home to me. However, this fuelled a new fantasy of actually being caught dressing up, and at that point my right hand definitely entered the picture!

It’s amazing to me, all these years on, that this fantasy still fuels such a big part of my sex life.

Contributor: Anonymous

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