Ashley meets Paige’s step bro, his Mom finds out about Ashley

Ashley took one measured step after the other down the hallway and into the living room. For what felt like the 100th time, he strutted into the living room, one foot in front of the other making sure his hips and ass wiggled dramatically with each step. A normal girl would never wiggle her ass so wantonly just walking around, but this is how Ashley was taught. The butt plug adding extra oomph to his hips. The steps were shorter than needed, making him practically mince with each step causing his faux breasts to jiggle, along with his skirt and curls. With his elbows tight to his side and hands outstretched with wrists turned out, he walked like a slutty bimbo. With a well practiced turn on his heel, he spun around so his skirt flew up a bit, just barely showing his panty covered butt before giving a smile and wink and walking back.

Paige sat in an armchair, watching with a smirk as she filmed the sissy. The wiggle of his butt as his skirt swayed from side to side, the bounce of his doll like curls on his pony tail, the click clack of his heels on the hard wood floor, all of it was a sight to behold. This was going better than she ever expected. She had enough now to completely ruin his social life so now so she was playing with house money, but she wanted to see how far she could take this.

“Oooo that was the best one yet, sissy! You’re really getting a hang of those heels! And your curls bounce so cute with those little steps! Such a good girl! But it’s getting late girly, so I think you should text your mom that you’re sleeping over and won’t be home until tomorrow. I don’t think she’s quite ready to see you like this… yet. Tell her you have a surprise for her tomorrow.”

Ashley minced back to Paige and nodded. “Yes Miss Paige. You’re right, this would be a big change for her to handle but im, like, oh so excited to show her the new me!”

Paige had Ashley practicing his girly voice and what better way than to use super girly lingo. Ashley went over and grabbed his phone, complete with a new pink phone case with a pair of red lips on the back, and typed out to his mom, with the help of Paige.

“Hi Mom! I’m staying over a friends house tonight. They’re, like, really helping me out with stuff I’ve been dealing with. I won’t be home until after school tomorrow and I have a, like, super surprise for you and I could really really use your support! Love you Mom!”

Ashley hit send after hesitating a moment. The three dots showed up showing his mom texting back.

“Ok honey sounds good. Everything ok? Are you in trouble again? If it’s another legal issue your dad will have a fit. You know he leaves for Europe tomorrow.”

Ashley typed back:

“Yeah, like, everything is totally cool. No trouble just finally accepting me and Paige is helping me out! Can’t wait to see you tomorrow.”

His mom responded:

“Ashley is everything ok? What do you mean accepting you? Call me”

Ashley looked at the phone unsure what to do. Paige read the message and a devious plan formed in her mind to really stick it to Ashley.

“Oh Ashley! I think it is time to let your mom know about the real you! Here I’ll call her and smooth things over ok? You just keep practicing your walk ok? Try some cutesy poses by the mirror”

Ashley nodded, trusting his bestie to help him with his mom as Paige walked away with the phone on her ear. Would she be ok with his new look?? Ashley looked in the mirror at his beautifully made up face and cupped his cheek making a cute little face like he’d seen girls do on social media.

Just then, Ashley heard the door open and footsteps come down the hallway.

“Hello? Anyone home?? I came back from college a little earlier today after I finished my final. Any one here? Oh! Hey there, girl. Sorry I don’t recognize you. You one of Paige’s friends? I’m her step brother, Casey, nice to meet you, beautiful. That dress looks amazing on you.”

Ashley turned from the mirror to see a boy around his age. He was taller than him but not by too much probably only 5’7 or so with shaggy brown hair that hung past his jawline. He had a pretty boy face with an easy smile, too easy of a smile where girls probably thought he was a scumbag but good looking enough to not care. His slender frame was athletic, but more like a skateboarder is athletic than a linebacker. Thin arms out of his t shirt and slim legs out of his khaki shorts.

Ashley looked at the boy and defaulted to the bubbly girly personality Paige had taught him this afternoon. He knew his voice wasn’t perfectly girly yet so he made sure to overdo the girly girl voice.

“Like, hiiii! Yes I’m Paige’s bestie, Ashley. Like, so nice to meet you!”

Casey smiled at the super bubbly girl and extended his hand to shake it. Ashley looked at it and held out a limp hand which Casey took gently in his.

Casey looked Ashley up and down, looking hard at Ashley’s freshly denuded legs shining from the moisturizer as well as his faux chest. Settling on Ashley’s tall shiny heels, Casey couldn’t stop staring.

“Wow, you look amazing. And all dressed up too. You look waaay too dressed up for a normal afternoon. Is there a cosplay convention or something? Who are you going as, I don’t recognize the character and I know I’d recognize one as sexy as you” Casey clumsily hit on Ashley, not realizing how demeaning and corny he was being.

But Ashley wasn’t used to being hit on by a boy and with his new girly bimbo persona he decided to take it as a compliment. Smiling brightly and giggling while twisting and twirling the skirt a bit, Ashley responded.

“*giggle* oh no nothing like that. My bestie Miss Paige dressed me like this. Thought it would bring out my inner girly girl. Is it working? Am I pretty enough?” Ashley sincerely asked, looking up with innocent doe eyes through his lashes, wondering if he did look girly to not just himself and Paige. Paige said he wanted to be the prettiest sissy in the world!

Casey was taken aback by the obvious, to him at least, flirting of Ashley. He wasn’t used to girls being this forward with him, he normally had to work really hard to get them to not think he was a creep, let alone be into him. But he recovered and turned back on the “charm”.

“Oh baby girl, you’re more than pretty enough. You’re hot as hell! Those legs with those heels look incredible. And I like the hair as well, you look like a sexy doll.”

Casey thought he was being suave not realizing how dumb and crude his compliments sounded. But all Ashley heard was he was pretty and that’s all that mattered so Ashley giggled and squealed a big “YAY!!!” bouncing up and down in his heels. Casey was given a show, seeing Ashley’s skirt bounce dangerously high up, while his small chest bounced slightly in his bra and his curly pony tail right along side them.

Casey was still holding onto Ashley’s hand and took advantage of the opportunity it seemed Ashley was giving him. Sliding his fingers over Ashley’s hand and starting up his arm he commented.

“Wow, your hands and arms are so smooth and soft. Are your legs the same way?”

“Like, yeah! They’re even smoother actually! Miss Paige did a great job!” Ashley said bubbly, happy that his feminization was being noticed.

Casey took that as an invitation, sliding his hands on Ashley’s thighs, feeling the smooth creamy skin. His hands crept upwards reaching the base of his skirt when he realized something.

“Miss Paige? You keep calling my step sis that. What does that…” but was interrupted.

“CASEY! What the hell are you doing?? And what’re you doing here?! Leave Ashley alone you creep!”

Paige stomped into the living room, seeing her step brother feeling up Ashley’s legs and getting dangerously close to what was under his skirt. Even tucked, not a good idea… yet anyways.

Paige was not a fan of her step brother. Their parents married a few years ago and she felt like he was always trying to smooth talk his way into or out of situations, and he wasn’t particularly good at it. He was always creeping on her friends trying to go out with them, but he just came off as sleazy. He wasn’t particularly lucky in high school and he seemed to have the same issues in college. But him immediately feeling up Ashley let it be known his ways hadn’t change. In fact, the old Ashley and Casey were surprisingly similar with their actions with girls. A lightbulb went off in Paige’s head to perhaps kill two misogynistic birds with one stone….

Casey dropped his hands from Ashley’s legs but didn’t immediately step away from the feminized boy.

“Woah woah woah! Hi Paige, good to see you again. Finished my exam early so wanted to spend some time at home. I was just getting to know your friend Ashley here and she said her legs were smoother than her arms. I didn’t believe her so I had to check.”

Paige was surprised Ashley would not just let a boy feel up his legs but ask him to.

“Is that true, Ash?” She asked.

Ashley’s head was confused. Didn’t Miss Paige want him to be pretty and seen as a sissy? Wouldn’t that include showing off how smooth his legs were? Obviously yes, but why was she angry?

“Um, yes, like I did ask him to. They’re so smooth and shiny and girly!” Ashley said As if that explained everything.

Paige smirked at his response realizing how deep the new ideas she planted in his brain were. A plan formed in her brain. A plan to humiliate both boys in front of her.

“Ashley you shouldn’t just let him feel you up without a date first. I know you’re a bit slutty but don’t give up the goods that quickly. But, a girly girl like you shouldn’t be without a boyfriend. How about you two go on a date after school tomorrow?”

Casey couldn’t believe his step sister was actively hooking him up with one of her friends, and her hottest friend at that! Not wanting to miss the opportunity he jumped on it.

“Yeah of course that sounds great! I’ll pick you up tomorrow then, how about that Ashley?”

Ashley heard that he was a bit slutty, which firmly implanted in his brain. But also that a girly girl shouldn’t be without a boyfriend. Those two new ideals cemented inside him as he eagerly nodded his head.

“Like totally! That sounds great, Casey! I can’t wait!” He said while grabbing his hand and stepping closer in his heels, pressing his slim body into Casey’s. Even with his short height, his 5 inch heels brought him an inch taller than Casey.

Taking the invitation, Casey responded, “it’s a date then. See you tomorrow, Ashley”. Putting his hand on the small of Ashley’s back, part of it on his skirted butt, he pulled him in and gave him a soft kiss on the lips. Ashley’s pink glossy lips met Casey’s and they held them together for a few moments. Ashley didn’t know what to do so he stood there with his hands out at his side as Casey kissed him, allowing him to move his lips along his glossy ones.

Paige couldn’t believe her luck, seeing her gross step brother kissing another boy all on his own. She quickly took out her phone and snapped a few pictures to capture the memory for the two of them forever.

“Alright love birds that’s enough. I need to take Ashley and talk to her a bit before bed. Now scamper off somewhere, Casey. You’ll get her tomorrow.”

Casey’s kiss lingered for a moment before pulling away with a smile.

“See you tomorrow, sweetheart” he said with a wink before grabbing his bags and heading to his old room.

After he left, Paige took Ashley’s arm in hers and walked back to Paige’s room.

“Omg Ashley! Your first kiss with a boy!! Omg I’m so happy for you you’ve wanted that for so long! And I know you want to go farther with a boy so we’ll go over allllllll of that before your date! I know he’s not the big manly muscled hunk you normally pine over, but you did say you have a soft spot for small feminine boys like him. Don’t worry, I’ll remind you what you like about them and what you want to do with them.”

“But before all that, I talked to your mom and explained everything. She took it SO well! She’s so excited to have a daughter finally! She’s making some changes at home while your dad is away so you can be comfortable in your new look. And she can’t wait to go shopping with you!!! Ooooo you must be so excited, sissy girl!!”

Ashley could only smile at all the information dumped on him, absorbing it all. And all the while his small voice screamed and raged inside him, trying to tell him something that he couldn’t quite hear….