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What shall I do with my winnings?


single sister Katelyn

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Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box. Please consider leaving feedback on issues you experience or suggest improvements. I was afraid. I knew I'd lost a bet with some guys I didn't really know and I had no idea what they had planned.

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It was in October when I first wore a dress. One day when I was at her place watching TV, while lazing in her double bed, she came into the bedroom from the kitchen. She walked in the room and kept her cell phone on the bed, went to the dresser and picked up a ruffle to tie her hair.

I looked at her from where I lay, she saw me do so in the mirror of the dressing table. Neha : U could be one today itself, all u have to do is put on a sexy outfit, say a short skirt Lost bet feminization a tube top. A few days later, we were sitting in the living room watching TV. Seemed like a fair deal. The next day in the evening, I went over to her place and to my dismay, I came to know I had lost the bet.

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As per the terms of it, I was to do whatever she said. And so, I was kind of ok about it. No major issues, I thought. Good shirts, good t-shirts, good jeans and I wear them in good combinations too. I agreed to it. At that time I was wearing a sky blue polo which happened to be my favorite polo with blue jeans.

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I walked into the room and there she was, standing next to the bed. On the bed was a dress.

It was a black dress, one of those little black dresses that women love to wear. It was something like the one in the pic below. It had narrow straps with an asymmetrical bottom.

Neha : Oh yes u are.! U lost the bet fair and square. You have to wear what I tell u to wear. I thought u were going to make me dress up in menswear, in color combinations of your choice.! It may be anything I want you to wear.

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I get to choose. She extended the hand in which she had the dress for me to take it from her. I was still not taking it from her. A bet is a bet.! You lost it and now u have to rise up to the occasion. Wear the dress. I just stood there, not knowing how to get out of it.

She always gets what she wants, I remembered. I resisted again, trying out all the excuses I could come up with but none stood their ground. Neha was to have her way, come what may. I thought to myself. Hell no.

The bet that started it all..

I undressed myself completely, put on the black bra and black panty. Had some trouble with the bra, but then got the hang of it.

Wore the dress and came outside the bedroom. Neha was sitting on the couch in the living room. Come and sit next to me sweetie. January 18, at pm. You are commenting using your WordPress. You are commenting using your Google .

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She smiled and laughed. Neha : You never know, what tomorrow might bring. Neha just smiled and went to the kitchen. But what happened next, shook me up completely.

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Neha : Then u thought wrong. Your fault…! Now put on the dress. It must have been really red. I had no option but to give up, and so, I finally gave in.

The bet that started it all..

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