Part 4 Family Friend Makeover

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Part 4

Steph takes another sip of the wine and pulls a sour face. “Why do my parents like this stuff?” She asks wiping her lips.

Smiling, I point at her face. “Err, Steph,” I chuckle. “You’ve wiped your mustache off!”

“Really?” She says touching her upper lip. “Ah …man, you don’t know how long that took me to grow it!”

“A long time,” I reply smiling. “Shame, you looked quite suave. In a drowned rat kid of way,” I joke as I reach over and flap her hanging sleeves.

Steph stops rubbing her face and pouts. “Well,” she says, as I watch the cogs turn while she tries to think of a comeback. “Least I’m not….not a silly school girl!”

“Hey now!” I reply flapping at my skirt. “I thought it was every boy's dream to be on a date with a schoolgirl!”

Steph shakes her head at my comment and the hat holding her hair in almost falls off her head.

Reaching up, she adjusts the cap. “I’m not like other boys,” she proudly boasts.

I couldn’t help but laugh at her as she pulls muscle man poses. My clothing just looked massive on her. She looked really funny and frankly a little odd.

“Steph, I can’t take you seriously,” I laugh. “I want to have a nice date with you, but you look so silly.”

“I’m having a good time,” she smiles. “I mean, you’re on a date dressed in my school uniform. We both look silly.”

Looking down at my pleated skirt and legs in tights, I could help but agree with her. It wasn’t the sort of stuff you’d wear on a date as a girl. Even I knew that.

“Maybe we should change back?” I ask in hope.

Steph doesn’t answer, she just gets to her feet and wobbles over to her bedroom door. Quietly opening it, she peaks down the hallway.

“James,” she says closing it gently behind her. “My brother must be downstairs playing video games.”

I shrug my shoulders and lean back on my arms, as I sit on the floor looking at her confused.

“Why does that matter?” I ask brushing my girly fringe from my eyes.

With a silly grin, Steph quickly pulls off my hoody and throws it to one side, disgrading it without care

“My brother's clothes would fit me better,” she says with excitement in her eyes. “How about you go across to his room, pick out some clothes for me for our date, and bring them back for me to wear!”

“Why?” I ask raising my eyebrow at her. “Don’t you think I’ve run about your house enough tonight in this frilly number?”

Steph instantly looks down at her feet. She cuts a dejected and rejected figure as I watch her wipe her eyes.

“J-just…t-though it would be fun,” she says with a sniff.

Getting to my feet as quickly as I could in my restrictive female clothing, I rush to her. Placing my fingers on her chin, I raise her face and our eyes meet.

“Will this make you happy?” I ask with a smile.

Her face lights up and quickly her frown becomes a smile.

“Yeah,” she says grinning, as she gently places her fingers on mine that is touching her chin. “This is fun, don’t you think?”

Staring into her sparkling blue eyes, I let go of her chin and wrap my arms around her hips. Grabbing her and bringing her close to my body, she places her arms on my shoulders. I feel a fizzing sensation in my panties, as she both stare at each other in the eye only a few inches apart.

“Ok, I will do it,” I say softly.

Steph closes her eyes and leans in towards me. Puckering my lips, I brace myself for a passionate kiss.

“Great!” Steph the unexpectantly cries out point-blank from my face.

Tricking me into thinking we were going to kiss me, she pulls away from our embrace. Opening the bedroom door, she ushers me out into the hallway, with her hand on my backside.

“Wait!” I say with frustration, as once more I’m outside her room in a schoolgirl's outfit. “What are you going to do while I’m doing this?”

Steph leans on the open door and gives me a playful wink “Seeing as your pretty much busting out of my clothes,” she explains as she touches the bulges in the blouse I’m wearing. “I’m going to borrow some stuff from my Mom and you're going to wear it.”

Sighing, I let my shoulders sag. “Really… your Mom's clothes?” I ask with a huff.

Not reacting to my sighing, she pushes me in the direction of my bothers room. “Get going. We don’t want to get caught wearing these outfits,” Steph whispers as she tips toes out of her room behind me. “Five minutes. Choose something and meet back in my room…ok?”

She was right, I didn’t want to get caught like this. Earlier on with her Mom in the kitchen was bad enough! I give her a nod in agreement and head towards her bothers room. Slowly pushing the door open, I’m relieved to find his room empty.

“Right then,” I whisper to myself as I sneak around her brother's room. I had to be very careful. The room was littered with Nurf guns, old dinner plates, and screwed-up dirty clothing. Lucky for me, wearing a skirt gave me extra room to maneuver around.

Spying his closet, I swiftly make my way over. Opening the closet, I start sliding through each hanger one by one. I had no idea what she would want to wear, but then I see it. Lurking in the back of his closet was a child's size suit jacket and pants. Dark blue in color and pinstriped. Quiet the interesting thing for her little brother to own.

“Perfect,” I mutter as I pull the suit from the closet.

Placing it over my arm, I quickly nab a white button shirt, a pair of black dress shoes, and a red tie and make my way back into her bedroom. I could hear her knocking around in her Mothers room as I made my way back. If she wasn’t careful, someone would come up and find her.

Seconds later, just as I enter her room, Steph hurries back. She pushes me into the room, from behind and swiftly closes the door.

“So!” she says excitedly as I find my balance after being pushed. “What did you get me to wear?”

I hold up the bundle of clothes in my arms as I turn to face her.  “I got you a suit to wear!” I say pleased as I notice she’s hiding stuff behind her back.

“Nice!” she replies as she blushes and goes bright red. “Think I will look nice in that do you?”

“I do,” I answer back also slightly blushing. “What am I wearing?” I then ask worriedly.

Slowly Steph reveals what she's got behind her back. Her face looks so excited as she starts holding up a black garment and some high heels.

“This is my Mom's Lucky little black cocktail dress!” Steph says holding it up and beaming a wide-eyed smile. “She says she always got lucky wearing this. I thought, maybe you could wear it and hopefully you will get lucky on your date tonight.”

“Heels?” I say pointing. “I don’t mind wearing a dress for you Steph, but heels?”

Ignoring my comments and points at the stuff I hold in my hands. “My bothers Pin strip suit. I like that on him.” She says nodding “We are totally going to look like a power couple!”

“Couple?” I ask with a wry smile. “I’m not sure I’m even going to ring the gentleman back yet,” I tell her in my lady of the manner voice.

Steph giggles and waves away my sarcasm. “Look, I will get dressed first, then I will help you into this dress…ok?”

Handing her the clothes, I take hold of the black cocktail dress and shoes. As she wanders into her bathroom, I hold the garments I’m to wear in front of my face.

The shoes look very uncomfortable with a long narrow heel and pointy toes. The dress feels amazingly soft, but it looks very tight. The neckline also looks very daring. I won't have the boobies to fill it, that’s for sure!

Waiting for her to emerge from the bathroom, I get a little bored. Standing on the spot, I start twirling around and allowing my short pleated skirt to twirl with me. It was fun. The sort of fun a boy never really gets to experience!

“James….?” I hear as I stop twirling and steady myself. “What do you think?”

Focusing on her, she stands in the bathroom doorway with a big smile. Gone was the cap and my oversized clothes. Replaced by a neat man bun on her head and the very sharp-looking pinstripe suit. Other than her slightly wide hips and her pretty face, she looked just like a dapper young man. She’d done the tie perfectly and the whole outfit radiated sophistication.

“OH, my days!” I blurt out as she stands in a power pose with her hands on her hips. “You actually look really good.”

Steph blushes and hides her pretty face behind her hands.

“You think?” she asks bashfully. “I think I look like my smelly younger bother… it's creeping me out a little.”

“Yeah…” I grin wide. “Crazy how well your wear that! I guess beauty is always beautiful, no matter what it’s wearing.

Steph smiles and turns away. Her face was now completely bright red.  iving me a shy look, she struts up to me and grabs the dress still in my hands.

“Now it’s your turn to be a feminine beauty,” she insists, grabbing my arm and leading me into the bathroom.

Pushing me in, she closes the door behind me. leaving a crack, where she pokes her head through, she smiles.

“You’ve gotta undo the zip on the back before you step into that dress,” she tells me. “If you don’t, you won’t be able to get that up and over your hips.”

Holding the dress, I find the back of it and run my finger along the zip “Anything else?” I ask as I start unbuttoning the blouse I’m wearing. “Maybe you’ve got some insight on how to put on these heels?” I sarcastically joke, as I hold them up and shake them about in my hand.

Steph raises her middle finger and flips me off. “Just hurry up!” she retorts. “Don’t be a stereotypical girl and keep your guy waiting ….ok!?”

Not getting a chance to have the last word, she shuts the door rather roughly. This leaves me alone, in her bathroom with the mission of putting on her mother's lucky black dress. How do I get myself in this situation? I think I’d prefer her family finding me in Steph’s uniform than this dress and heels.

Sighing, I discard her blouse, which reveals to me my girly bra. Tugging at the bra straps on my shoulder, I’d almost forgotten I was wearing one. Then pulling down the skirt, which reveals the very feminine panties, I allow it to fall around my ankles.

Scratching my head and stepping out of the skirt, I start talking to myself. “James…,” I say quietly. “she’s worth it. Just keep making her smile.”

With that, I reach for the dress and unzip the back. Holding the straps to the dress, I guide my legs in. Gently pulling the soft material over my hips, I struggle to get my arms into the straps. After a few huffs and groans, I soon realize the reason why the straps won't go over my shoulders. They aren’t even supposed to! The way the dress is cut, the straps hang off the sides of my shoulders.

“Oh geez,” I moan as adjust the dress to hide my bra and my modest sock boobs. “I feel odd having my shoulders out like this.”

Looking down at myself and the dress I’ve just put on, I’m honestly stunned at how well it fits me. The tapered skirt sucks my knees together and stops me from standing like a guy. Running my arms down my sides and to my hips, it almost felt like I had an hourglass figure. The dress was really squeezing me and shaping how I looked.

“Oh, my days!” I say shocked as I look at the feminine reflection looking back at me through eh mirror. “I really am starting to look like my Mom!”

“Come on sweetheart!” I hear Steph call from the other room, breaking from my trance.

Reaching around my back, to do up the zip, I cheer as I manage to do it all by myself. “I don’t need her help putting on a dress,” I smirk.

Lining up the pair of heels in front of me on the floor, I take a deep breath. Slowly sliding one of my feet in. my foot molds to the unrelenting side of the heels. Squeezing my toes into the pointy end and my heel into the back, I step my other foot into the other heel. Rising up and stand tall in my heels, allowing my weight to balance on such a small point. I Steady myself, I take my first step.

“Ouch!” I groan as my leg muscles strain under the pressure of standing up on high-heeled shoes.

Pacing around, with small steps due to the restricting dress, I make a clicking noise with every step. Taking a few minutes to get used to my new height and how much it feels like I’m standing on ice, I Grab for the door. Swinging it open, I take a deep breath in and prepare myself for what's to come.

To my surprise, she’s acting real smooth. Leaning up against her chest of draws, she holding a pencil in one hand, pretending to smoke it and holding her wine glass in the other.

“Boys,” she says in a nineteen-fifties style gangsta voice, to her array of teddies on top of the drawers. “Hold my drink. I’ve just seen a little cutie on the dance floor.”

Strutting over to me, still pretending to smoke the pencil, she elevates her eyebrows up and smiles.

“Hello sweet cheeks,” she says, still doing a nineteen-fifties gangsta impression. “I’ve not seen your beautiful face here before.”

Running her hands across my waist, she brings me in close and holds me against her. Wearing heels, I now tower over her. She as to arc her head right back to look up at me.

“Hey,” I say in a monotone voice as I place my arms around her. “Do I look ok?”

Steph takes hold of my arms and places them on her shoulders. It felt weird not having my arms around the girl I’m embracing, but she was taking the lead with this. I suppose I do look more feminine than her right now.

“Hunny,” she tires saying really suavely. “You’re the prettiest girl I’ve seen!”

I couldn’t help smile and laugh. She was pulling faces like guys from cheesy romance films.

“Can I have this dance?” Steph asks still taking like a gangsta and throwing her pencil cigarette off to the side. “How does a beauty like you come to a place like this without a chaperone?”

Playing along, I start talking in a very high-pitched voice. “I just haven’t met the right man, kind sir.”

Still pressing our bodies against each other, we start slowly dancing on the spot, rocking side to side. I was glad for this, every step in her mother's heels felt like I could collapse at any moment to a heap on the floor.

“I’m sure you have!” Steph says while playfully squeezes my backside. “I’m sure you’ve known the right person for you for years. Maybe that person has been waiting for you to notice her.”

Stunned by her very loaded comments, I look down to see her blushing and smiling from ear to ear.

“I guess…… I’ve been a little blind to it, yea,” I reply as she squeezes me on the backside once more.

Without warning, Steph pushes my torso down and hangs me over her arm. My head falls back, and I stand on one leg, with the other pushed up into the air. Leaning over me, as she holds me up, she smiles and leans in.

“Just kiss me beautiful,” she says pouting with closes eyes.

As she holds me up, my hair dangling from my face and one of my legs held aloft in the air, I thought I’d had more reservations about kissing her. I was wrong. I wanted it. I wanted her. Without another second's hesitation, I pucker up and her soft supple lips, passionately kiss me once more.