Double Dare 1 - Double Dare by Maeryn Lamonte Melanie Ezell's Big Closet Ultimate Writer's Challenge — 5th Mar — The Challenge

“Nah, you'd be surprised. He may look like a wimp, but he's got guts. Oh hey Steve, we were just talking about you.”

Yeah right. This was a setup if ever I smelt one, but they'd played to my weakness and I couldn't resist.

“What was it you were saying? What don't you think I'll do?”

“You know Portia Allen? She just broke up with her boyfriend. Jon here doesn't think you've got the bottle, but I reckon you'd have the guts to ask her out.”

Portia Allen, heart-throb and heart-breaker rolled into one. Every guy in school dreamed of Portia , but only the most worthy would ever be permitted to spend even as much as a few seconds in her company. Unfortunately for me what made one worthy seemed to be big muscles and a small brain, the exact opposite of what I had to offer. Still there might be some mileage in this. You get kudos just for asking, and maybe I could swing a little more.

“What's in it for me?”

“Well I'd've thought the prospect of a date with the lovely Portia would be enough.”

“Except you know as well as I do that I'm going to get shot down in flames.”

“Alright, if she turns you down I give you twenty quid, but if she agrees, you gotta do anything she says.”

Now I know it's a setup. Still I'm in too deep now, and hey, it's a date with Portia. Even with conditions, that has to be good.

“Okay, you're on.”

“She's in the cafeteria now, come on.”

They grabbed an elbow each and frogmarched me through the double doors. The place fell abrupt silent. Portia sat with her back to me at the other end of the room. Oh well best get this over with. I marched past the gawping bystanders to her table.

“Er, hi Portia.”

She turned and gave me such a withering look, I actually felt myself shrivel. Somehow I found the guts to speak again.

“I was wondering if you might like to go out sometime. On a date sort of.”

It kind of trailed off towards the end, but it was out. Now I'd either be twenty quid richer or no amount of money would be able to buy my happiness.

“Hyeah right. Do you have any idea how much damage it would do to my reputation to be seen with a scrawny little thing like you. I mean you look more like a girl than a boy. In fact, you know, the only way I'd be seen in public with you is if you were dressed as a girl...”

“Done.”

“What?!”

If there's one thing I've learnt it's when things start going down the tubes you have to take control. If I’d let her keep going she'd’ve had me dressed up like a baby doll and sitting in a stroller. Besides, she didn't know, right now she was offering me the realisation of my most cherished dream.

“I said done, but three conditions. One you and your friends make me look good; I don't want anyone laughing at me. Two you don't make any long term changes that have me looking like a girl for months. Three you make out with me in the cinema.”

That last was a bonus and potentially negotiable, although it did score me some points back in this idiot's game. She was wrong footed, didn't know how to react. Oh please, if there's a God in Heaven let her say yes.

“Er, okay sure.”

Yesss! Inside I was fist pumping like mad, outside I was trying to stay calm. Time to bring home the bacon.

“Friday evening then, pizza and a movie, and since we're going as girls we go Dutch.”

And let her have the final word now that there's nothing much left to negotiate with.

“Okay, but since we're going as girls we go see a chick flick.”

Fine by me, all the better for making out. Besides there wasn't much else on that I wanted to see. I stuck out my hand. She looked at it suspiciously, but shook it even so and the deal was sealed.

“You'll have to come around straight after school on Friday; it takes a long time for a girl to make herself look good enough to go out. And you'll have to bring your own underwear, I'm not lending you any of mine.”

There were a few snickers from around the room, but most everyone there knew I had won this one big time.

“I'm sure I can sort something out. I'll meet you at the gates at the end of school on Friday then.”

The week dragged after that. I told my parents early to prevent them ruining things by arranging something else. I also managed to convince one of the nicer girls in the school to buy me the required bra and panties plus a pair of tights as I didn't expect to get out of this without wearing a dress. I gave her the money and my measurements, and by end of school the following day she had come through for me.

Oddly, the people who normally poked fun at me steered clear over the following days. Instead I got used to whispers following me down the corridor. It seemed like most of the school had yet to make up its mind whether I was cool or mad. Either way I was riding the wave and getting some respect for a change.

Friday came at last and I headed off to school with a second bag containing my weekend clothes. I figured Portia might try a little spiteful revenge by 'accidentally' leaving my clothes in her room and leaving me to go home in her dress, so I hid my spares deep in the bushes at the park. The day was the longest ever, but the bell went eventually and I headed down to the front gate with a huge entourage of onlookers, all eager to see if I would actually go through with this. Portia and her friends were waiting and tried to walk off ahead of me, but having slightly longer legs it didn't take me long to catch up.

Back at her house, she led me up to her room. Her parents weren't home yet and I suspected wouldn't be too impressed if they found out she'd had a boy up here without their knowledge. More incentive for Portia and co to do a proper job on me.

I was told to strip and shower, instructed which potions and lotions to use and left to it with a fluffy pink dressing gown and my underwear. Half an hour later, and smelling decidedly floral, I was sitting in front of a mirror in Portia's room, experiencing my fondest dream in full sensorama, surround sound and 3D Technicolor. Portia worked on my long hair, trimming some split ends and styling it with a decidedly feminine wave. Amanda worked on my face, tweezing eyebrows — not too much mind — and doing something decidedly artistic with Portia's makeup kit and Jenny and Debbie knelt either side of me, filing and painting my nails in a pearlescent pink.

Once they were done, and the nail varnish dried, Portia opened her immense closet and showed me her selection of dresses.

“I was thinking of wearing this.”

She held a midnight blue dress in front of her. It was just right, I knew she would look stunning in it and told her so. She shook off the complement.

“Your colouring's a bit different though so I thought you'd look good in this one.”

Pastel pink, of course, with puff sleeves, frills and a full skirt. I doubted there was a more girly item of clothing in her wardrobe.

“I like it.”

It wasn't the response they were expecting, especially since I softened my voice to sound more like a girl. That was when an odd thing started to happen. The more feminine I became, the more they accepted me and by the time I was dressed, and looking stunning by the way, I was just a fifth member of their group.

In the end we all went out together and had a fantastic time, laughing and giggling over our meal like, well, schoolgirls. I didn't actually make out with Portia at the movies, but at the end of the evening all four girls gave me a big communal hug and told me they couldn't remember the last time they'd enjoyed themselves so much. Portia apologised for sending me home in a dress, explaining there might be questions from her parents if I suddenly appeared from upstairs as a boy. She told me to keep it 'til next Friday when I've been invited over again, this time for a sleepover.