Sissy Stepbrother

Chapter 1

"What is this?!" Tom shouted at his stepsister Michelle as she strut out her room in a pink dress and pantyhose.

"Um, I'm going shopping with some friends, what?" She asked making a show off the knee-length and sleeves... But all he could see were her huge breasts practically falling out of the dress!

"Come on, you know you're boobs are coming!" He said looking up at her slightly. Both had less than a year between them (Michelle was just fifteen) and in very early teens. "And this... Is inappropriate!"

"So what, just because my dad married your mum makes us nothing to eachother!" She barked at him before breathing deeply, "look just because you don't have boobs and wear clothes which would expose them doesn't mean that you can criticise my outfit."

"What?" Tom laughed in shock, "you're saying because I'm not a girl I judge you as sluttishly dressed!"

"Yeah, now get out my way, Jess, Sara, Isabelle and Eve are waiting for me!" She told him, using her slightly height advantage to reach past him and pull on the bar for power and push past her stepbrother.

"Bye, slut!" He shouted after her as he went back into his room to... Well he didn't even know, he was just gonna sit there really, like always.

This was exactly how most days went for him, but today his aunt Claire, as well as her twin daughters, which ment one thing for him. His mum would spend all the time searching for a photo album she had lost. Every year they came over for a month and his mum spent almost all the time searching for that photo album.

He never understand why she didn't give up, or why she wanted it that badly.

So he decided to just hang out in his room and only interact with any of them if he had to. But almost as soon as he flopped onto his bed the twins made themselves welcome, "you're new dad told us that one of us have to stay with you." Either Sara or Lola snarled at him. He thought it was probably Sara as he could actually get on well with Lola.

"Seriously! You know what, have my room, I'll sleep downstairs." Tom muttered taking some things from his room and setting up the couch.

***

Over the next few days he did his usual routine: he didn't pay attention in class, hung out with his friends making immature jokes and talking about random things. Then when he got home he'd have an after-school nap and watched TV until he went to sleep.

Then, just two days before his relatives left Michelle strutted up to him with her hands holding something behind her back and a huge smirk on her face.

"What the fuck do you want?" He groaned at her, waking up from his nap.

"Oh... Tom..." She put the photo album down in front of him then turned it to a certain page.

His eyes widened in pure terror, his face went white. On the page was a photo of him, no older than seven, in a dress with loads of makeup and his still long hair in near pigtails. He grabbed at the photo before ripping it apart. "I made copies." Michelle said casually.

"Rip them up!" Tom demanded standing up.

"I could?... But then I wouldn't have a girl to help me shop for clothes!" Michelle sighed.

"No! No way! Don't even try! I'm not going to dress up as a girl!" He denied.

"Oh, come on... My girlfriends are all from my high school... We could even shop in the next town over?" Michelle offered giving Tom some black nylon panties as well as a nylon bra and white stockings, a t-shirt and microskirt.

He held up the smooth underwear and soft stockings before putting them back down and grabbing the microskirt, "seriously! This thing would barely cover my ass!" He complained.