The Prom Bet

“This is so not cool!” Walter complains as Alley brushes his sky blue wig. “I didn’t think we’d actually go through with this….”

Alley rolls her eyes, huffs, then continues to brush the wig's tangles.

“Alley…..come on please!” Walter continues moaning as he sits patiently on her bed. “I didn’t think we’d really be doing this.”

Stopping, Alley kneels down in front of him and smiles.

“Why are you complaining now….?” She asks as she runs her finger across the tight corset hugging his body. “Other than your dress, you're almost completely dressed as a girl.”

Walter sighs and slumps. “I know…!” he groans. “I just thought you’d let me off after doing my makeup. I didn’t think it would ever get this far. I mean, look at me in this bloody underwear. This awful corset is crushing my bones!”

Alley gets up off her knee and resumes brushing out the wig. Pushing through the thought knots, Walter whines with every pull.

“Stop whining!” Alley demands as she moves onto the back of his head. “You lost the bet fair and square.”

Walter folds his arms and grumbles. “I can’t believe I thought I’d get better grades than you.”

“Nothing like spending the night in a dress,” Alley giggles “To teach you to stop being so cocky.”

“Oh Ha Ha,” Walter says with a sour expression. “This would have never had happened if you’d just asked Olivia out y’know.”

Alley takes a step back and looks at him with an open mouth.

“Walter!” she cries. “That’s not cool! You know I couldn’t ask her out…she’s not a lesbian.”

Alley pauses for a moment and taps the hairbrush against the side of her leg. “You can’t give me crap about that,” she continues. “You didn’t ask out Sandra either!”

“Good thing too,” Walter answers back sarcastically avoiding eye contact.

Alley points the hairbrush at him and waves it around. “Oh,” she replies “Why is that then!?”

“I don’t think she would have wanted to go to prom with me dressed like this,” he answers, pushing out his very fake feminine chest towards her. “Do you think she’d be happy if I turned up to pick her up looking more feminine than her?”

Lowering the brush, Alley couldn’t help but smile back at him. “No,” she giggles. “I guess not. Still, I kinda like it!”

“Oh god,” Walter groans as he deflates his chest. “You're not getting a crush on me….are you?”

Stepping towards him, Alley gives him a sharp look. “No, you big dope,” she laughs. “Now shut up, so I can brush this hair out. I assume you don’t want to be recognized tonight….do you?”

“No…. I don’t,” Walter instantly replies. “I’d rather no one found out about this. Please do your best to make me look like anyone else but myself.”

“Sure thing…Wanda,” Alley giggles with a playful smile. “We are going to be such a cute couple!”

Walter lowers his head and looks down at the only male clothing he has on. Lucky for him, Alley didn’t want him walking around her room with only a pair of her lacey briefs holding back his tackle, so she’s allowed him to wear his gym pants over top.

“Wanda?” Walter, he asks with a groan. “Don’t get any idea’s about this Alley….ok. Once this bet is done, I’m not dressing as a girl ever again.”

“Sure….sure,” Alley answers as she pushes some clips into walters hair. “Your loss.”

A silence falls over them both as Alley starts concentrating on styling the wig. Using clips and copious amounts of hair spray, she finally takes a step back and looks proud of her work.

“Is it done?” Walter asks impatiently.

“Sure is,” Alley says with a grin.

“That took longer than the makeup,” he says rolling his eyes. “At least when you doing my hair, you're not poking at my eyes, as you did with that bloody makeup.”

“Your such whimp,” Alley retorts as she points at the bathroom. “Now, get in there and take those gym pants off. And before you ask, no, you can’t wear them under your dress.”

With hair falling in front of his face, he brushes it out of his eyes and makes his way over to the bathroom door. The bounce of his fake boobs, pressed against his bare chest by his corset, was enough to make him smile.

“Whoa,” he says animatedly, standing in the doorway. “These things move around a lot..huh?”

Alley continues to point at the door with an unchanged stern expression.

“Alright…alright,” Walter says in defeat. “I’ll go put on the dress and take my gym pants off. Just stop giving me that face….. you remind me of my mother.”

Walter closes the door behind him and finds himself face to face with the large blue prom dress hanging from the shower curtain. Lifting the skirt of the gown, he acknowledges how heavy it feels.

Pulling down his gym pants, revealing his panty house and matching black feminine briefs, he looks himself in the mirror

The reflection facing back at him was one he didn’t recognize. A young, well-made up, feminine face stares back at him.

Softly touching his cheek, he remarks how good a job she’d done of his makeup.

Moving his hand down his cheek and onto his now hairless chest towards his fake boobs, he accidentally knocks her toothbrush from its holder.

He watches on as the toothbrush tumbles down into the sink bowl with a clatter. As the toothbrush circles, the drain and comes to a stop, Walter's head starts pounding like crazy.

Clutching onto his head as the vice-like pain emanating from his skull increases, he lets out a cry of pain.

As the pain shoots down his body and enveloped him completely, his thoughts turn to one of terror and sheer panic. Just as quickly as the pain cripples his body, it then instantly vanishes, leaving his skin tingling with static energy.

Confused, he takes his hands away from his face and stares terrified and bemused into the mirror.

Finding himself completely baffled, he notices that the toothbrush is now back in the holder and no longer resting in the sink where it should.

Picking the toothbrush up with his fingers, he holds it up to his face. His mind struggles to comprehend what just happened. He was sure it just fell into the sink, but he could no longer be sure. All he knew for sure was that pain, how odd it made his body feel, and how odd it still feels.

His body felt so different. The feeling of heft, where it shouldn’t be, and an odd feeling of an absence. 

“Wanda?” Alley calls through the bathroom door. “I heard you cry out…are you ok?”

Walter quickly spins Is head to look at the still-closed door. His hair flickers around as he moves his head quickly.

“Y-yeah……,” he responds, but instantly stops talking due to how very strange his voice felt and sounded.

In a blind panic, he touches his neck, wondering if this pain has done something to his voice.

“Are you sure you’re ok sweety?” Alley asks with a knock on the door. “Do you want me to come in?”

Walter looks down at his half-naked body and shakes his head. His body looks so curvey and the feelings of his ribs being crushed by the corset had vanished.

“N-no….,” he replies with a very effeminate voice. 

“Wanda,” Alley says as she slowly pushes open the door and stands in the doorway, “What's wrong?”

With her opening the door, Walter quickly shifts his hands towards his package, wanting to cover it from her sight.

Alley looks on confused she Watler turn as white as a ghost.

“Wanda,” she asks. “What's the wrong…..?`

Walter’s jaw drops and his heart rates doubles. Holding his hands around his privates, he can’t feel anything. It’s completely flat. It's completely gone! Nothing was hanging where it’s supposed to be!

“M-my…..,” he stutters. “My….wheres it gone!?”

Looking down at his body in fear, he almost faints at the sight he sees. Two very real flesh mounds stick out from his chest. Pushed up and out by the garments he’s wearing.

“My God!” he cries out as he pokes at them and feels everything. “These are real. Seconds ago they were rubber!”

Walter looks up at Alley in fear. He can’t understand what's happening.

“Alley….,” he says trembling. “W-why…..do I have boobs and what's happened to my penis!? Where’s it gone!?”

Expecting Alley to be just as worried and concerned, he’s very surprised when she just chuckles in response.

“Wanda,” she says dismissively. “What the hell are you talking about? Where’s your penis….that’s an odd thing for a girl to say.”

“What…..?” Walter replies as he holds himself awkwardly like he’s scared to touch anything on his body. 

“Get dressed!” Alley exclaims and points at the dress. “We haven’t got time for this! You need to get your dress on. I’m still not dressed either and the limo will be here very soon.”

“Alley,” he cries. “A moment ago I had a..a…a penis… and now it’s gone.”

Alley scoffs and gives him a wry smile.

“Riiight,” she says as she narrows her eyes. “You such a weirdo. I don’t know what weird game it is that your playing.”

Walter opens his eyes wide. He’s struggling to understand why is Alley acting like this. Why is she not more surprised at his random sex change.

“No game!” Walter shouts. “I’m not a girl. Why has this happened!?”

“Stop,” Alley says with a calming gesture. “I can see you’re upset, but I don’t understand. Why are you saying you’re not a girl? You're upsetting me a little.

“W-we…were….dressing me as a girl,” Walter says confused and holding his head. “Then I came in here to get changed and then I felt a huge pain.”

Placing a hand onto Walter's bare shoulder, Alley gives a comforting smile.

“What do you mean dress you like….a girl?” Alley asks “You are a girl… so it’s just getting dressed.”

Daggers in his eyes, he shows Alley the corset and underwear he’s wearing in frustration.

“Remember…” he groans. “I lost the best and now I’m dressing like this?”

“What bet?” Alley asks as she takes her hand away from his shoulders. “Wanda, this isn’t funny. Why are you acting like this on our prom night? We’ve been looking forward to this for months. I thought you couldn’t wait to announce our relationship tonight.

Walter looks at Alley’s furrowed brow and shakes his head. The fog just won’t clear and he can’t think straight.

“B-but….,” he replies and slumps. “I’m…. a….boy….I’m sure.”

Standing with both hands on her hips, Alley tuts.

“No….no your not,” she growls. “Now, let me help you into your dress, then you can help me into mine.”

Walter stands completely limp with shock. He allows Alley to guide his feminine body into the blue gown and sinch it tight against his narrow waist. She adjusts his neckline and any stray hairs.

“I knew you’d look pretty in this dress,” she comments and holds his hand. “I’m such a lucky girl having you as my girlfriend. All the boys are going to be jealous of me.”
“Huh….?” Walter responds with a vacant expression. “Your…my girlfriend….? I thought you only liked girls?”

Alley playfully taps his hands with her fingers.

“Please don’t start that’ again Wanda,” she complains. “I do only like girls. Good thing you're my type…eh?”

Walter doesn’t reply, he just looks down at the heavy blue gown draping off his body. It didn’t feel unnatural at all. The dress felt made for his body with the way it clings to every curve on his feminine body.

“How long have we been going out?” He asks softly, running his fingers through his very real long hair.

Alley, now stripping out of her casual clothing, rolls her eyes.

“About two months…,” she answers. “Yeah… two months.”

Walter watches his stunning young friend get naked in front of him. Part of him knew he should be getting excited about it, but the usual feelings of growth were absent.

Scratching his head, he raises his eyebrows at how beautiful Alley’s body is. Feeling a little uncomfortable, he looks away.

“What's the matter?” Alley scoffs as she flaunts her now naked body casually in front of him. “I hope you're not going to be like this tonight. I thought we were going to take each other’s virginity.”

“What…..!?” he replies back as his heart rate doubles. “We’re going to do what now?”

Blushing, Alley look away with discomfort

“Y-yeah….,” she says awkwardly. “You’re not having second thoughts…..are you?”

Walter shakes his head, still trying to shake the fog clouding his thoughts.

“I still don’t…,” he pauses and remembers the pain from earlier. “I’m so confused, have I always been a girl?”

“Yeah….?” Alley replies as she checks her face in the mirror. “I don’t know what you’ve taken Wanda, but please don’t be like this tonight.”

Alley turns, smiles, and grabs Walter's waist. Bringing him close, her naked body presses against his gown, and their breasts squash together.

“I know it’s worrying,” she stays gently. “Coming out as lesbians to the whole school is hard, I know. Don’t get cold feet, I’m going to be at your side the entire night. No one can hurt as, as long as our love for each other is strong.”

“Love…?” Walter replies awkwardly as privates react in a totally new and unexpected way to Alley’s attention.

“I’m sorry it took me so long to say it,” Alley answers as she closes her eyes and blushes. “You remember….our first kiss?”

To Walter's surprise, images flash in the mind's eye.

“I-I….do..,” he answers very surprisedly. “Under the slide, at the park….hiding from the rain.”

Alley’s face turns brighter red and her smile widens.

“Yeah, that’s right.” She says smiling.

“Yeah…. I do…. Actually, remember that” Walter continues saying as some of the fog clears from his mind.

“I kissed a girl…,” Alley sings softly. “and I liked it. The taste of her cherry chapstick.”

A new and exciting feeling fizzes between Walter's legs. He blushes, as he listens to the beautiful young girl embracing him and singing harmonically.

Bringing his hand to her soft chin, he lifts her face slightly so their eyes meet.

“Alley, you should go get ready,” He insists. “That beautiful red gown ain't going to put itself on.”

Alley smiles and rises on the tiptoes to plant a kiss on Walter's cheeks,

“Hold me tight tonight,” he says gleefully.