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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.
Chapter 26
Please don’t make me go in there dressed like this. I said to my sister was we sat in her car. Of course I still dresses in the boots, leggings and dress. “You know that she said if you ever come home dressed like this you have to go to the salon.” That’s because I couldn’t change back into my boy clothes before we got here. “Well that’s not my fault you’ve got yourself trapped under the control of Miss Emily and her lawyer. As well as Miss Sterling and the store and now it looks like you’ll be under moms control as well.” Claire I don’t want to be under the control of anyone. “Well you did all this to your self and as mom always says you made the bed now lay in it.” We got out of her car and it was so weird and humiliating to look down at my legs covered in the black leggings and the boots zipped up to just below my knee caps. The tight dress that I had on that just annoyingly fit me so well. I was used to the panties by now but the bra the bra was annoying and it hurt. This was the moment of truth as we stepped inside the house.

“I’m in the kitchen guys getting dinner ready.” “Okay mom we will be right there!” Claire can I please just go run up to my room and change before mom sees me dressed this way? Claire looked to be considering my request. Will she let me? I hoped so! “Fine go run up and change! But hurry!” Thank you Claire you’re the sweetest sister! “I know! Just hang the dress in the closet and put the leggings away in your dresser and put the boots in your closet also!” Fine no problem! It was a fair condition i thought and was a lot better then some mom humiliation. I ran up to my room and quickly unzipped the boots an boot them in my closet. I took off the dress and hung the dress up as well. I took the leggings off which also gave me an electric shock! I had no choice but to leave the panties on. That’s all I had! I struggled and struggled to take the bra off but I couldn’t. I just hope mon wouldn’t notice as I went down for dinner.

Chapter 27
Miss Claire’s POV

Now I know what you guys are thinking. I could have sent my sissy little brother to the wolves right now. Our mother would have humiliated him and sent him right to the salon but you see I’m playing the role of the sweet sister and I have my own plans, but little does he know in the one who’s pulling all the strings behind the curtain. All I had to do was stay the course and everything would come to me, and after everything was all said and done I’ll still be his sweet big sister. I’ll be his savior! Finally my brother came down to dinner so now we could eat. I wonder if he got the bra off? “Oh look it’s my son. Home from a hard day of work folding leggings and zipping up boots.” My brothers face got bright red. My mom could be so ruthless and I enjoyed it. “Mom that’s not what I do there. I unload boxes!” “Well eventually they will have you do that there and then that will lead to wearing them and zipping up boots legs. Wearing dresses and skirts and trading purses with your sister. That store will turn you into a girly cream puff priss!” My brother looked down at his plate his face as red as could be. I was enjoying it so much! Although I had to play my role to perfection! Mom go easy on him. None of that will happen. “Oh it will all of what I said will happen just give it time! Hell for all we know he could be wearing leggings in secret!” I highly doubt that mom! “We’ll are you? Do you prance around in leggings and boots alone in your room?” “Mom I don’t! Now stop it!” That’s all my brother could take and he got up from the table and ran to his room.

Mom that was harsh but you might be on to something. “Of course I’m on to something! All go what I said will come to be.” Do you think he is really dressing and prancing around in his room? “It’s a possibility! You would tell me if you knew of any of this going on right?” Of course mom! “Good! Because there will be no in between he’s either a girl or a boy.”
Poor Nick must’ve been terrified but Claire is terribly more sweet than I thought. Nick in time is going to realize this as further and further into being Nicole.

Still Love it, thanks, keep it up.
Claire clearly has a long game planned here and it will be interesting to see exactly where it goes. As for Nick’s mom, could things have become any more awkward? Having come so close to the truth, how will she reactwhen she finds out she’s been lied to here?
Just like Claire, mom I think is very clever and will be sweet. Very excited to see how it pans out.
Chapter 28
“Swish swish swish! Swish swish swish! Swish swish swish! Come Nick don’t you want to swish with me? Swish swish swish! Swish swish swish!” I was puzzled as I awoke to my sister walking across my room back and forth. “Come on what are you waiting for? Come swish with me! Swish swish swish! Swish swish swish! Pull up your panties and leggings and come swish. I promise that you won’t be disappointed.” Without question I did what my sister asked and I walked to my dresser and took out a pair of panties and put them on. The followed the leggings as I slide them up my legs. “Good now zip up your boots and put on your dress.” Once again I did what she asked without question. “That’s perfect! Now come swish with me!” What was my sister talking about? I began to walk across my room back and fourth. Sure enough there it was. Swish swish swish. Whenever I walked I had a shock of erotic pleasure with rose to my crotch and caused it to be on fire. “See? Swish swish swish.” Oh my god Claire I said. “Looks like we got a love one.” and she pointed to my crotch. Whenever I walked swish swish swish and my penis expanded and expanded. “Say it with me. Swish swish swish!” Swish swish swish! “Again again!!” We did it again and again until I eventually exploded and awoke to a sticky mess! What a dream!

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