Part 3 | Family Friend Makeover

Please let me know if you enjoyed this by leaving a like and a comment. Let me know where you think their story should go next!

Read parts 1 and 2 first

Or listen to the audiobooks.

Rubbing my arm nervously, I gaze into my beautiful friend's eyes and find myself completely tongue-tied. I know I’m wearing her school uniform and we just kissed, but I was stumped by her omission of love for me. I just wasn’t expecting it!

“Steph, you love me?” I ask her gently as she looks back at me with desire in her eyes. “I mean… I mean…. why and how!?”

“Do… do you not love me back?” she asks, tears welling up in her eyes.

“Steph, I think our kiss was amazing, don’t get me wrong,” I answer as I put my hands on both her shoulders and bring her in for a tight embrace. “I…. I…. wasn’t prepared for you to tell me that you love me!”

“I…er…guess I have just sprung that on you, huh?” she mutters into my chest. As she speaks, I can feel her pushing against my sock boobs as we cuddle.

Softly pushing away from my body and gently grabbing my hands, she looks at me with an open and honest expression.

“James, I’ve wanted to tell you that forever. I’ve wanted to tell you how I really feel about you,” Steph reveals to me with passion in her voice.

“Wait what?” I ask interrupting. “How long have you felt like that about me?”

Steph swiftly pulls her hands from mine and looks down at the floor. Her lush hair falls in front of her face and she doesn’t seem to care. It was almost like she’s trying to hide from me.

“Does it matter how long?” she answers with a slightly distraught mumble.

“Steph,” I say softly as I tuck her hair behind her ear. “I just want to understand. Please don’t be upset. I’ve... just broken up with my girlfriend and my best friend has just told me she loves me, it’s a lot to take in.”

Steph continues to look down at the floor. She’s clearly tearing up as I see her shoulders move up and down as she whimpers.

“Hey, talk to me,” I say as I bring her in for another tight embrace.

Steph nestles her head into my sock boobs once more. It was weird for me to have to adjust how I cuddle to accommodated my fake female chest.

“I’m sorry James,” she says quietly into my chest. “I shouldn’t have said anything.”

I didn’t know how to answer her. She had completely blindsided me and I was in no way expecting her to admit she loved me! Not knowing what to say, I gently stroke her soft hair in my absence for any words.

“Now I’ve gone and made it all awkward,” Steph blurts out all frustrated. “You’re not going to want to be my friend anymore, ……are you?”

I much as I would hate to admit it to her, it had got a little awkward for me. I think with all the excitement of her dressing me as a schoolgirl, I’d got carried away. The thing is, I don’t regret kissing her, but I’m struggling to understand what it is that’s holding me back. I do love her, but is that as a friend…? I’m so confused right now!

That’s when an idea then hits me like a lightning bolt.

“Erm, Steph,” I say gradually, breaking the silence. She looks up at me, her eyes are red and watery. She’s clearly been crying.

With my idea, I hope I could turn this situation around. I really didn’t want to upset her and I really didn’t want her to think I wasn’t interested! I mean how could I not be interested in such a smart, funny, and beautiful lady like her? I think I just needed some time to get my head straight.

“What?” she asks impatiently while wiping her sore-looking red eyes.

“Come with me,” I insist as I release her from our embrace, grabbing her hands and leading her out of the toilet.

“Why?” she grumbles as I pull her back into her room and plonk her down in front of the vanity mirror, that I’d spent so much time in front of this evening. “James, what are you doing?”

“Do you trust me?” I ask her with confidence.

“Well, yeah of course I do,” she responds as she looks at me through the reflection in the mirror.

“You see how I’m dressed as a girl and even wearing your underwear?” I ask her as I twirl my body. My skirt is dancing as I spin around on the spot.

“Yeah?” she gently smirks. “You do make a pretty girl.”

“Well, I think it’s only fair that, if you love me, we go on a date… right?” I reply with a massive grin on my face. “Lady Bamforth can’t be seen dating a girl….. what would the country club say!” I joke in my silly lady of the manner voice.

Steph giggles a little, but it isn't enough for her to crack anything more than a slightly forced smile. “What are you saying?” she asks confused as she slumps and rests her chin on her hand.

Reaching for a baseball cap, that she has hanging from the back of her bedroom door, I hold it above her head. “Can you put your hair up into a bun for me?” I ask politely

“Sure,” she answers confused, but quickly bundles up her long hair and wraps It into a bun on top of her head. She uses a hair tie, from her wrist, she sinches it together. “Why though?”

“I told you,” I playfully clown in my silly voice once more. “If Lady Bamforth is going on a date, it can’t be with a girl!”

Steph's face instantly brightens and the spark returns to those beautiful blues. “Oh….., ok,” she laughs. “I think I get what you saying.”

Placing the baseball hat on her head, I give her a humorous wink.

“But James,” she asks as her expression returns to a frown. “We can’t go out with you dressed like that, so how can we have a date?”

“Don’t you worry about that,” I answer with confidence, as I flick my hair like a teenage girl. “I’m going to quickly go downstairs and get some stuff for our first date.”

Instantly turning around in her seat to face me, she looks worried. “James, you can’t go down dressed like that! What if my family sees you.”

I give her a reassuring look and rest my hand on her shoulder. “You….. you are worth the risk,” I tell her with a beaming smile.

“Really?” she asks as her cheeks go bright red. She was clearly a little embarrassed by my comments.

“Yup!” I quickly answer and make my way to the door. “I will be right back! Do you think you can get yourself ready for our date, while I’m gone?”

Steph cracks a smile and nods.

Gently opening the bedroom door, I peek out into the hallway. As much as I wanted to do this for her, I really didn’t want her family to see me wearing her school uniform. The skirt was bad enough, but to be wearing her underwear as well, our families would never let me live it down.

Nervously, with my heart beating like mad, I take my first step out into the hall. I tiptoe to the stairs and do my best to sneak down them without making a noise. I could feel my skirt flapping as I moved, it was a massive reminder of what was at stake. My pride as a young man was on the chopping block!

I make it into the kitchen without being seen. I knew I was playing a dangerous game, as I hear the TV roaring in the next room. I didn’t bother turning the light on, it was more sneaky that way. Taking a deep breath in, I tenderly open the fridge. The bottle drinks rattle in the door as I gradually open it.

“Shhh” I signal to the bottles in the fridge door.

I quickly survey the fully stocked fridge. Brushing the girly styled hair from my eyes, I start wondering what to take. I quickly make up my mind and as I reach up into the fridge, I could feel the girly blouse restricting my movements. I knew we shouldn’t, but I was going to make this night special, so I reached for the half-drunk bottle of white wine they had. Just as I place my hand on the bottle's neck, the kitchen light suddenly flicks on.

I freeze on the spot. I was too terrified to move. Someone has just entered the room!

“What are you looking for Stephanie?” I hear her Mom say as she walks behind me and turns on the kitchen tap.

I keep my head buried in the fridge and dared not to turn around. Her Mom must have seen the girl's school uniform and assumed I’m Steph. To keep up that charade, I do my best to pretend I’m looking for something particular in the fridge by picking up stuff and putting it down again.

“Sweety,” her Mom says as I hear her fill a glass with tap water. “What are you doing in the dark and why aren’t you ready for bed?

She doesn’t give a second for an answer.  “As soon as your finished, please go get into your pajamas and brush your teeth….ok,” she says with a motherly tone.

Silence follows as she waits for me to answer. I could feel the nervous sweat now running down my face as she waited for my answer. I couldn’t reply to her in my normal voice! She’d know it was me straight away and I’d be busted! With the pressure, the only thing I could think to do was to answer her with my Lady Bamforth voice.

“Yes… Mother,” I say with my silly voice and trying to give it some Steph-like attitude.

Her Mom lets out a little giggle. The problem was, I couldn’t see her so I had no idea if she’d brought it or not!

“Sounds like my little lady is eating too much sugar,” she states as I hear her walking behind me. “Stephaine, no more sugar or you will ruin that lovely little figure.”

I didn’t want to push my luck, so this time I didn’t answer her back. Lucky for me, she’d already left the kitchen and gone back into the other room. I wipe the sweat from my brow and let out a sigh of relief.

Quickly pulling the white wine from the rack and closing the fridge door. I start searching for wine glasses, and that’s when I see two on the draining board. I grab them both. Clutching it all tight, I knew it was time to retreat back to Steph’s room. The wine wasn’t much, but it would have to do!

As I rush back up the stairs, I could feel the breeze gusting up my flapping skirt. It wasn’t an experience I was used to, but one I didn’t completely dislike. It felt very refreshing.

Pushing open her bedroom door, I enter the room to find she’s doing something in her bathroom. This gave me a chance to set our date up. Grabbing a blanket from the bed, I lay it down flat on the floor. Setting the leaning tower of pizza slices in the middle, I put a wine glass on either side. It was like a picnic, just in the middle of her room.

I sit cross-legged on the floor as I wait for her to appear from the bathroom. As I wait, I pour the wine into the glasses. I’d never tried wine before and I had no idea if she liked it, but that’s what people do on dates… right?

I bring the glass to my face to take a sip and that’s when the toilet door cautiously opens. Steph steps out and stands uneasily in front of me.

“What do you think?” she asks anxiously rubbing her arm.

She’d put on my jeans, t-shirt, and hoody. The jeans did fit her quite well but the t-shirt and hoody almost completely drown her. I couldn’t see her hands at all, as they were hidden in the sleeves, that are too long for her short arms.

She’d kept her hair up in a bun and the baseball cap completely hid the fact she even had long hair. She’d also removed all the makeup from her face and had even drawn a fake mustache on with mascara. I couldn’t help but smile and laugh. She looked a little ridiculous. Not unlike me, I suppose.

“This is my date for this evening?” I say in my lady of the manner voice, laughing as I do.

Steph just slowly nods.

“Well my dear,” I say, continuing my silly voice. “Don’t just stand there, come join me.”

Steph gives me a big smile and kneels on the floor. I hand her a glass of wine and she looks at me with worry.

“We shouldn’t have this?” she tells me, looking extremely uneasy. “What if my parents find out?”

Give her a raised eyebrow and a grin. “Steph, look at us both. If your family walks in on us, I think the wine would be the last thing they’d ask about.”

Taking a small sip, she scrunches her face up from the taste. “Gross!” she comments as she puts it down and laughs.

Looking up, she then gives me a longing look and a wide-eyed smile. “Thank you,” she says with vulnerability in her voice.

“What for?” I ask as I take a small sip and pull the same scrunched face.

“For this,” she smiles.

I shuffle my body over to hers, so I’m sitting next to her. She leans over and rests her head on my shoulders.

“I’d do anything for you Steph,” I tell her.

She giggles and reaches across to one of my fake sock boobs. “Clearly,” she mutters as she gives one a playful squeeze.

“Oi!” I joke as I bat her hand away. “I didn’t plan for you to get to second base on our first date!”

She leans back upright and gives me an ecstatic look. “So, does that mean I get a second date?”

I could see the delight in her eyes. I wasn’t quite ready to love her back, but I wanted to explore my feelings for her. I mean, I’d never had a girl draw on a fake mustache for me before.

“I think so,” I chuckle. “Maybe on our second date, you can wear the skirt?”

“Deal!” she says laughs ecstatically.