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A Part Time Job At The Leggings and Boots Boutique: Sweet Sister Bratty Boss Story
In the end it was a no hoper - Claire knew from the outset that the threat of criminal proceedings would be enough to bring Nick into line (though the riding crop didn’t do any harm either). What did we agree Nick’s forfeit was for losing the bet again?  Wink
Yep, saw it coming, and what a cute outfit to end up in, I hope he realize despite the 'hard ship' it is rather nice and comfy.
Chapter 24
I don’t want to be welcomed to girlhood! “Well too bad it’s happening! Imagine what mom is going to do tonight and you have to do it because you lost our bet.” I bowed my head in shame. Why do you have that riding crop? “Miss Delacourt gave it to me. She said it will help out at home. Maybe I will get one for mom too.” Please don’t do this Miss Claire I’m your little brother. “Little sister you mean and I instead to do it! I intend to do it all! Now go show Miss Emily and the others your outfit!” Miss Claire pushed me out of the dressing room and showed me off to all the girls. “Oh wow!” “That’s such an amazing outfit!” “You did so good Emily.” “Yeah and you too Claire.” There was also a few customers in the store that came up to us as well. “Hold on hold on! Are you a boy?” I gave a meek response of yes I am. “Hahaha! Wow what sort of boy let’s himself be dressed like this.” “A good question and the answer is only a sissy!” “A sissy? I like that! How long has he been a sissy for?” “I’m not sure but probably forever.” “That’s awesome! Well Nice outfit!” After that a few other girls came up and said and asked almost the same question.

I could feel my penis constantly stretching out into the fabric of the leggings. Luckily no one could see it because of the dress. “What a successful day don’t you think so Emily?” “I do think so Miss Delacourt. Will we be back tomorrow?” “Of course we will. We have to make sure little Nicole here obeys our rules, and she knows the consequences if she doesn’t! Jail time! Hahaha!” Miss Delacourt and Miss Emily left the store laughing. “Well looks like you lost your battle with Miss Emily.” Miss Sterling why don’t you do something? “I can’t do anything about it. It has nothing to do anything with my store now as the lawsuit has been transferred to just you. Like I said this is your battle. However, we do need to talk about your outfits.” What about them? “Payment obviously! You didn’t think you would be getting them for free did you?” Well I didn’t think about it at all. “Ha well so far you have racked up a $1000 in purchases.” A $1000? I can’t pay for that! “Well looks like you’re in another predicament. I guess you can work it off.” Work it off? What about my pay checks. “Oh it’s simple you won’t be getting paid until everything is paid off!”

Chapter 25
Miss Claire’s POV

Miss Sterling can you believe all this? “Believe what dear?” Everything! All this craziness with my brother. “Well I suppose it’s crazy if that’s what you think.” You don’t think it’s crazy. “Oh sweetheart you’re smarter than this. It’s not crazy! It’s all been planned.” Planned? No way! It all seems so real. “Well it’s not real! My sister is Miss Delacourt and Miss Emily is my niece.” I was shocked too say the least. But why? “It’s simple we want to turn your brother into a girl, and judging from that crop you’re holding you want the same thing.” I do Miss Sterling but let me ask you something. Why my brother? “He’s a perfect candidate! He’s submissive and petite and could be easily transformed into a Princess. Plus I want him to be trapped working at the store. Do you have any objections to that?” Of course not I’d love to be co workers. “Well hold on now you will be his boss. In promoting you too Assistant Manager!” I jumped up and down. Thank you so much Miss Sterling! “But of course you’re very dedicated to my store.” Miss Sterling are you thinking of making my brother get surgery? “Well that’s certainly in the cards but your mother would have to be onboard.” Leave that to me I’ll make it happen.
Legal obligations and rising debt - Nick really is in it up to his eyeballs. Of course, this is just the start. Now they have him where they want him there are no doubt so many other obligations they will wish to impose on him.

In a way he should be glad they currently have him by the gonads as there may not be any gonads to have him by soon if they get their way.  Wink
SissyNicole117, I am loving the latest chapters, keep it up, please.
Girlygirl, your insight is perfect on the current score.

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