The bet

I had just agreed to a bet with my girlfriend, Serena, she said that she could make me a princess, I said there was no way in hell she could feminise me to the extend where I would feel comfortable going out in public. 2 hours of makeup, body conforming and trying on clothes later and I had to admit, I looked amazing.

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It could come as a surprise that I am guy. Although I looked female, I was still uncomfortable under the ton of makeup, tight dress, even tighter panties and most uncomfortable of all where the heels.

The bet was that if she could dress me up like a princess then the next day after college, I would dress as a little girl and come to the park with her and if I won she would dress as a little girl and I would be her dolly, now I thought about it, it was a very unfair bet.

I guess she had won the bet so that next day went to town to buy my clothes.

We were in the little girls section of a big clothes shop. She was holding dresses up against me and saying things like "this will look nice on you"

Every time someone walked past I went a deep shade of red and they always gave me a funny look. We had been in there for hours and I realised that the only way to go home was to play along.

She held up a small pink dress. It had puffy frilled arms, a pink collar and fours bows, two on the arms, two on the waist.

"That one's really cute!" I said

"You think so? I like it, you'll make such a pretty little girl, why don't you go and try it on?" Serena said

"Uh well i... " I stuttered

"Oh yes! Of course, we need to get your manipedi, hair and makeup done first! Thanks for reminding me" Serena said

We walked into a salon and I sat down in the chair. The salon was very girly and pretty with a very strong pink theme, it was called "princess makeover"

"Sir, what kind of princess makeover would you like" the cosmetologist said, with hint of confusion and uncertainty in her voice

I nervesly looked at Serena, she shot an evil grin at me and nodded.

"I, I..." it was so embarrassing to be asking for a girls makeover in a shop called princess makeover "... could I have two brown pigtails, my eyebrows doing, a bit of lipstick and mascara... and... a pink manipedi" I finished

She was quite surprised I could tell and it took her about five seconds to respond "o-of course sir, anything e-else"

Serena butted in and said "yes, a full body waxing too"

This wasn't just a fun game anymore sge was getting revenge for something.

The whole time my hair was being done I was thinking about what she was mad about. A couple of weeks ago she had caught me in her pink pantyhose and leotard.

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Maybe that is what she was mad about. Or it could be me stealing her Halloween French maid costume

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or it could be a couple of years ago at prom when I dressed as a girl and stole her date

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Although she did compliment me on my makeup and hair when that happened.

I was so lost in thought that I didn't realise that they had already done my hair and makeup and were moving onto the waxing. I could see myself in the mirror, I looked like a total fool.

The waxing only got more and more painful each time, it was over rather quickly though, ten minutes. But after that my legs and arms felt so smooth, I was actually quite enjoying the experience, until I saw her.

It was my sister, she always did whatever she could to humiliate me in every situation she and I were in.

I just hoped she wouldn't see me, in a pair of little pink panties, devoid of any body hair, with makeup coating my face and my long brown hair in pigtails. I really hopes that anyone I saw would not see me.

I needed to hide and I figured a good place was the changing room.

"Come on Serena, I want to try on the dress" I said, snatching it off her

"This little sissy's keen" she taunted as I ran of with the dress

I stepped in the changing room. With great difficulty I pulled the dress over my head, making sure I didn't smug my makeup or ruin my hair.

The dress was short, reaching a quarter of the way down my thighs, it was made for a 9 year old girl after all. In the changing room I found a pair of black heeled sandals and slid them on my feet. It was hard to walk.

I looked at myself in the mirror-

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I was so embarrassed. Anyone I saw would know it was me. I had to admit, the thought of dressing as a girl always excited me, that's why I did it at every opportunity. But then time I had no excuse, it was not a costume and I could not tell anyone it was for a bet because Serena would not let me.

I readied myself for about a minute, thinking of excuses, ways to escape.

After I had plucked up the courage, I drew back the curtain and stepped out, only to be met by my sister and a crowd of her friends

*Snap* *snap*

Went the cameras of everyone.

"You're gonna be in panties and petticoats for a long time sissy" said my sister, Rachael "and I have enough blackmail to last year's"

If anyone wants me to write another part then just send a writing.com email to me.

Thanks for reading