Alice's new 'sister'

 

Kate and Liz had been friends since childhood, they grew up around the corner from each other and had gone to school, both had gotten married and the both had given birth to one child. Over time they kept in touch with each other despite the fact that Liz had moved out to the country with her husband and daughter, so they no longer saw each other as regularly. 

Kate's husband died no longer after their son's 10th birthday, while Liz had gotten divorced shortly before that, and it was these combined events that brought them back in more regular touch with each other.

Alice was a beautiful blonde girl, trim, well toned and of course a cheerleader, in her final year. She was popular around school, she wasn't bitchy in any way, and would go out of her way to help others. .

Matt himself was a shy introvert 4 years behind, who could barely look a girl in the eyes let alone talk to one, and naturally anything beyond that was really out of the question. He was also physically weaker and smaller than what is considered normal for someone his age. 

During that school year, Liz's job required her to travel out of the country for a few weeks, naturally she was reluctant to leave Alice alone for that long. It was not that she didn't trust her to look after the house properly, it was just that it was so important for Alice to keep up her studies and prepare for her finals. So she turned to her friend Kate and asked would she be able to help out. 

It was a few days into her stay when Matt accidentally walked in on her as she stepped out of the shower, little droplets of water glistening on her slightly tanned skin, her long wet hair sticking to her upper chest. He immediately reddened and stuttered out a sorry, before running into his room and closing the door. 

Alice dried herself off, hot dressed in a t-shirt and jeans, and then went to Matt's room and knocked on the door. After a few minutes he let her in, and she said she forgave him but to be more careful next time, and knock and wait before coming in.

Two days later though she thought he was watching her from a crack in his door as she went from the shower back to her room, she grabbed a pair of shorts and a tshirt and barged onto his room, as he was lying on the bed, his trousers slightly tented. 

"Eew, well aren't you just a little pervert and I mean little in more ways than one, I bet you even walked in on me on purpose a few days ago, well if you want me to stay quiet on this you better stay totally out of my way, coz if I think you are trying to see me naked again, or if I think you are jacking off to me then you will suffer for it. Everyone things I'm sweet and nice, and that makes it easy for me to get away with things as nobody believes I could be capable of being mean."

Matt made sure that he stayed clear and kept his door open just in case for the remaining week. However it wasn't enough as on the final day he bumped into her as she left the shower room, what he didn't know was Alice did it on purpose. She said to him, it's just as well for you I'm leaving in an hour, otherwise I'd have to put my plans into action, but I won't forget this, so stay out of my way or next time we meet it won't be good for you. 

About two months later Kate had to go away unexpectedly to tend to her sick father, so she asked Liz could she return the favor and mind Matt for a short while. Needless to say he was horrified at the thought and tried anything and everything to dissuade his mom from this, but to no avail. 

When he arrived at Alice's he was brought up to the guest room. It was tastefully decorated but there was no escaping the fact it was very feminine in style. He immediately felt uncomfortable in the room there was far too much pink and frills for one room. That's when Alice walked in, and reminded Matt that she hadn't forgotten what she said last time they say each other. Matt started to unpack, and that's when he realised to his horror that his mother had only packed two spare sets of school clothes and not much else. With it being late in the evening he had either the choice of one of Alice's nightshirts or sleeping naked. Naturally he decided to sleep au natural, but the silk sheets meant he had a very uncomfortable night's sleep. 

Without any shops nearby, to get underwear in Matt had a problem, and so reluctantly had to wear panties, from an unopened pack Alice provided, and that night he reluctantly would have to take one of her nightshirts. She made a point of saying how cute he looked in her sparkly pink nightie, and if his hair was a bit longer could nearly even be mistaken for her sister. With only three sets of clothes he was also limited in what he could wear, but he gladly accepted that problem, rather than take up the alternative option of wearing something of Alice's.

After around two weeks Liz was required to go out of town for a long weekend for a business meeting, she had expected Kate to have returned by then, but having no alternative and given it was only a  few days allowed Alice and Matt to remain unsupervised.  

"Right you, I'm in charge now for a few days, and you'll do exactly what I say or else everyone will know how 'small' you are. For the next two days you will be known as Madison or Maddie for short , you are going to be my sister and you will wear what I give you to wear" 

Over the course of the next hour Alice got to work on Matt, she did a little delicate tidying up of the eyebrows,  but nothing too obvious, made sure he shaved his legs, applied a light coating to his fingernails. Next she gave him a bra which she stuffed to look somewhat natural, a pair of tight panties to help tuck his little dick in, and a pair of panties to wear over them which matched the bra. Then she gave him one of her old cheer uniforms to put on, and finally a dark wig. 

Matt, or rather Maddie was dreading what else Alice had in store for him. What followed was hours spent being essentially Alice's living doll, being dressed up in all manner of girlish things and finishing up that night curled up on the sofa beside Alice eating popcorn and watching a chic flick 

If Matt thought that was all that was it, he was mistaken as Maddie spent the next two days, having to be a little sister to Alice, and trying hard not to do anything wrong that would give her cause to tell everyone. So consumed with trying to do things right, he failed to notice the little red light of the cameras, secreted in the living room and also the guest bedroom where he slept. By the end of the long weekend though Matt had become quite comfortable pretending to be Maddie, no longer reacting and getting annoyed at being referred to as a girl, or being called Maddie. Perhaps it was the fact that Alice's mom was going to be home tomorrow, and he could put all this behind him helped. He was in a short yellow sundress and low heels sitting on the sofa with Alice thinking about being able to be Matt again when Alice's mom walked in.....along with his own mom.

What Matt didn't know was that the whole thing was a ruse by his mom

    She wasn't tending to her sick father she was actually at home in their house. . 

    Liz, hadn't a business trip to go to at all, but only went to see Kate for the weekend. 

    They had set up the incidents for Matt to 'accidentally' see Alice naked, with her approval.

    All the footage had been streamed back to the Kate and Liz, had been shared with his mom. 

 You see his mom felt that Matt should really have been a girl, plus he wasn't ever going to be boyfriend / husband material and based on what she saw from the past weekend she was more convinced than ever given how easily he adapted to having to be a girl. 

"MOM?, what are you doing here I thought you were out of state. This is not my idea, Alice made me do it, she's not as nice as people think she is"

"That's where you're wrong, Alice is exactly who people think she is. That is why I asked her to do all this, she was precisely the right person. Tell me honestly did you like the past weekend" 

"NO. I eh, oh I don't know, well I suppose kinda, yes"

"What was it that you liked? "

"I can't say for certain, but after the first few hours it just felt, well this sounds weird but it felt relaxed and I felt right "

"Now can you see that she actually did you a favor, I think she has helped you realise who you truly could be, if you wanted to of course"

Alice then interrupted to apologise for how she acted and for being so hurtful in what she said when she was staying over, but said it was all just an act and part of the plan, but it was necessary. She also said how much she had enjoyed having a sister for a few days, and if Matt wished to keep on being Maddie, she would love to help out and act as a big sister to her. 

Matt's head was now spinning with all this information overload so many questions filled his head, he started to get light headed, he stood up to go and get some air, and promptly collapsed to the floor.

He awoke several hours later in the very feminine pink room, dressed in one of Alice's nightdresses convinced his name was Madison, and was Alice's sister.

The End