Published on BigCloset TopShelf (https://bigclosetr.us/topshelf)

Home > Maeryn Lamonte > Double Dare

Double Dare

Author: 

  • Maeryn

Organizational: 

  • Title Page

Audience Rating: 

  • Mature Subjects (pg15)

Taxonomy upgrade extras: 

  • Transgender
  • Fiction
  • Crossdressing
  • Posted by author(s)
Double Dare Series
by Maeryn Lamonte

The first chapter was intended as a one off story as part of Melanie Ezell's Big Closet Ultimate Writer's Challenge — 5th Mar — The Challenge

It seemed to take on a life of its own however, so grew into a short mini series.

Steven isn't the most popular kid in school. He keeps himself to himself most of the time, then a couple lads dare him to ask out the most beautiful girl in the school, and one thing Steven can't turn his back on is a dare. When he asks the question, the ante is upped as she dares him to go out with her dressed as a girl.

Double Dare 1 - Double Dare

Author: 

  • Maeryn

Audience Rating: 

  • General Audience (pg)

Contests: 

  • Ultimate Writer's Challenge: Melanie Ezell

Publication: 

  • Novel Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

Other Keywords: 

  • Dares
  • High School

Permission: 

  • Posted by author(s)
Double Dare 1 - Double Dare
by Maeryn Lamonte

Melanie Ezell's Big Closet Ultimate Writer's Challenge — 5th Mar — The Challenge

-oOo-

“I bet you he won't.”

“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.”

-oOo-

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.

Double Dare 2 - Double or Nothing

Author: 

  • Maeryn

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Novel Chapter

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School

Other Keywords: 

  • High School

Permission: 

  • Posted by author(s)
Double Dare 2 — Double or nothing
by Maeryn Lamonte

Steven just spent Friday evening out on the town with the four hottest girls in school, only he was wearing a frilly, pink dress at the time. Going back to school on Monday is going to be interesting.

-oOo-

Monday started off as bad as I’d expected. Jon and Matthew were upset that their little plan to humiliate me had backfired so badly on them and had apparently camped out near the cinema waiting for Portia and me to turn up. They’d used their phones to take photographs and text them to all their mates, which meant that by the time I turned up back at school, the only person who hadn’t seen the incriminating evidence was me.

“What does it feel like to be a girl?”

“Hey poofta you steer clear of me, I’m not into gay love.”

“Hey Stephanie, I thought you looked really cute on Friday.”

None of the taunts were particularly original, but when you get a constant stream of them they start to get to you. I hadn’t been on the school grounds ten minutes and I was already on the verge of tears. I couldn’t give in to that though; if the humiliation was bad now, wait until they added ‘crying like a girl’ to my list of sins.

My life was over. I’d taken a chance on this, hoping that actually getting to go out with Portia might be enough to balance the shame of being seen in public in the frilliest, pinkest dress in existence, but it obviously wasn’t, not with the smear campaign that Jon and Matt had directed against me.

The thing is I could hardly blame them for their attacks on me. I was queer, even if not in the homosexual meaning of the word. Kinky might be a better word for it, because after I left the girls on Friday night I didn’t stop enjoying myself.

-oOo-

I’d walked home rather than take the bus, luxuriating in the feel of the clothes and the knowledge that I looked so very pretty in them. I mean what kind of boy gets his thrills from something like that?

I made my way to the park where I’d left my weekend clothes. I’m pretty sure Portia was genuine in her regret about leaving me to walk home in her best party frock, but she hadn’t even offered to collect my school uniform from her room at the end of the evening. Too much risk of her parents seeing? Forgot? Realised that I was enjoying wearing the dress too much? Or maybe there really was a vicious streak in there somewhere. I guess I’d find out on Monday when she refused to talk to me.

I climbed out of the dress with more regret than even I suspected. I had no hanger, so carefully folded and rolled it and placed it inside my already empty bag so that it wouldn't get dirty. My two makeshift breasts, made from birdseed in a pair of old tights by Jenny I think, went in the bag as well along with the petticoats that gave the skirt all its body. I kept my tights and girly underwear on — in truth I’d forgotten to put any boxers in with the other clothes in the bag, but I probably wouldn’t have used them if I had — and pulled on my jeans, and sweatshirt. I could still feel the soft material of the panties and bra as well as the cool caress of the tights under my clothes, but I still felt a sense of loss in turning back into me.

Tatty trainers replaced the pair of pink pumps and a little bit of work with the wet wipes — a parting gift from Amanda — had enough of the makeup off for me to feel safe going home. The nails were a different matter, but I could always keep my hands in my pockets for now.

I made it through the door five minutes before my curfew. Mum and Dad were snuggling on the sofa in front of the idiot box. I guess it’s nice that they’re still that close after all these years, but I didn’t want any of it. I headed straight for the stairs.

“Did you have a nice time?” Mum wanted to know.

I stopped and peaked back into the lounge.

“Yeah it was great. There were a bunch of us, had an absolute blast.”

“What did you go and see?”

“Nothing memorable. Listen, I’m wiped out, gonna go to bed.”

I ran up the stairs before there were any more questions.

I pulled the dress out of the bag and hung it at the back of my wardrobe. I couldn’t leave it in the bag all week after all, it would get creased. I changed into my pyjamas, feeling a few last pangs of regret as I took off the tights and underclothes. They’d need a wash though and the only way I was going to get that done was by hand. It only added a minute to the brush-teeth-go-to-the-loo routine after which I hung them up under my dressing gown on the back of my door. They wouldn't dry very quickly there, but at least they would be away from prying eyes.

-oOo-

Saturday morning was typical with Mum and Dad heading off somewhere early on and me declining the offer to go with them, preferring my weekend lie in. Only this time I couldn’t stay in bed. I was fidgety and restless, wandering about the house looking for something new, something that was disturbing my peace. I knew what it was though and before long was sitting on my bed changing into my bra and panties — still slightly damp, but what the hey. The tights followed, then the petticoats and the dress.

I went into my parents' room and looked in my Mum’s full length mirror. No makeup other than the very pink nails — I’d have to use some of Mum’s nail polish remover before the day was too far gone — but still enough of a wave to the hair, and that slight shaping to the eyebrows. It was a girl looking back at me through the mirror. She smiled at me and I was filled with a new realisation of how much I actually liked being her.

I had the rest of the day to myself and didn’t want to spent it wandering aimlessly around the house. Saturday morning TV was its usual waste of time, but instead of slobbing in front of it and letting it rot my brain as I usually did, I found myself in the kitchen, strapping on one of Mum’s frilly aprons and hunting through her recipe books for something to cook. I had never taken an interest in that sort of thing before, but it seemed to be a part of the emergent me, the one that liked to wear dresses. I probably made a bit more mess than is usual, and the cookies, when they came out of the oven, were misshapen and a little crispy round the edges, but the whole experience of cooking, swirling around the kitchen in the dress, imagining myself to be just another girl cleaning the place down afterwards, was a heady drug and I was definitely high on it. So much so that I lost track of the time and only just managed to duck back upstairs before the sound of keys in the door turned into my parents in the hallway and a very embarrassing situation.

The dress and pseudo-breasts went back into the wardrobe and I jumped into my jeans and sweatshirt again, jamming some not too stinky socks on over the tights just as there came a knock on the door.

A quick check of the room to make sure there was no incriminating evidence left lying around and I called out the all clear. Mum’s head appeared through the door.

“Sweetie, did you bake those cookies?”

I shrugged.

“There was nothing worth watching on the TV and I was bored. You don’t mind do you?”]

She came all the way in and took a step towards me.

“Not if you clean up the kitchen after you, like you did. Oh my, your nails.”

Oh bums, how could I have forgotten that? Think quick.

“Yeah a couple of my mate’s girlfriends thought it would be funny. I can’t wash it off, I don’t suppose you have anything do you?”

“I’ll get you some remover.”

She gave me an indulgent smile and ducked out the room. Poor silly Steven, doesn’t even realise you need acetone to dissolve the stuff. Yeah keep thinking that Mum, it’s better than the alternative.

-oOo-

After my narrow escape, normalcy re-established itself. As a reward for my efforts in the kitchen, and my consideration in cleaning up after myself, we bought in fish and chips and rented a couple of DVDs — my choice — from the local video place, then, with the witching hour looming, I headed off to bed, once again washing my smalls as part of my evening ablutions.

Sunday passed in much the same way as usual. I felt oddly guilty going to church with pink toenails, but at least I had forgone the lacy underwear and nylons. Back home afterwards, my Mum asked if I wanted to help with lunch. I knew it wouldn’t be as much fun without the dress, but I agreed even so and surprised myself with how much I enjoyed it. I know the kitchen isn’t solely a woman’s domain, but helping out still made me feel more like a girl and I realised I didn’t actually need to be suitably dressed for this new person inside me to rise to the surface.

Mum gave me a few odd looks as I chatted with her and followed her directions with whatever she asked me to do. After we’d eaten I headed for my room and homework. Mum joined Dad in the lounge and I half heard my name and a few mumbled comments in a concerned voice before I closed the door on them.

-oOo-

And that brings us back up to date. Friday evening and Saturday had seen a timid part of me poke her head out of the shadows. Gentle coaxing would probably draw her further out and the rest of me wanted that to happen. The way things were going this morning though, it wasn’t looking likely. The jeering of my peers was like banging on the side of an aquarium full of anemones, the delicate part of me was in full retreat. Then Portia and her friends showed up.

Followed by an expectant cheer from the mob, they made a beeline straight for me. Okay girls, go on, just how much more humiliated do you think I can be?

Debbie was first. She walked straight up to me, put her arms around my neck and planted a long and luxuriant kiss right on my lips. It took me a moment to respond, but long before the kiss was over, I had my hands on her waist and was kissing her back. Eventually she withdrew with a wink and a smile.

“Hi Stevie. Thanks for Friday night, I had so much fun.”

Amanda was next, sliding her body close against mine and inserting her tongue as far into my mouth as it would go. Again it lasted for the best part of forever before she pulled back.

“Hey Steve. I’m sorry, I guess I did take a little more off your eyebrows than first intended. Still I think it takes real guts to do what you did on Friday. Who’d a thunk that the sign of a real man would be that he was prepared to put on a dress?”

She gave me a parting caress on the cheek and ceded her position to Jenny who all but jumped on me. Again the kiss, so sweet so soft.

“Oh Steve, you are the best. I can’t wait for this weekend, just the five of us alone.”

And finally Portia. Sweet Portia of the radiant smile and unfathomable eyes.

“Hi Steven. You left these in my bedroom on Friday.”

She handed me my uniform, washed, ironed and neatly folded. I thought she might slip past without introducing me to her plump red lips, but she was just teasing the crowd. Her’s was the longest, gentlest kiss of all.

“See you later. I’ll save you a seat at lunch.”

They carried on into the main building leaving the school’s entire male population staring in silent disbelief at what they had just witnessed. The anemone’s fronds were back out in the current and ready to sting anyone who came too close. Matt and Jon were within easy earshot. Time to stick in the barbs.

“Worth wearing a dress for? Oh I think so.”

I turned and followed the four hottest girls in school through the doors.

Double Dare 3 - Double or Quits

Author: 

  • Maeryn

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Novel Chapter

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School

Other Keywords: 

  • High School

Permission: 

  • Posted by author(s)
Double Dare 3 — Double or Quits
by Maeryn Lamonte

Monday morning changed a lot of things for Steven. Every boy in the school was jealous of the attention he had received from Portia and her friends, and none of them were standing by him. It was just as well then that more and more girls were becoming friendly with him, except that they were only interested in the girly side of him…

-oOo-

Following Monday’s interesting start to the day, the rest of the week has turned out to be pretty weird too.

For starters, I’m now on hate radar with pretty much every other guy in school, missile lock with most of the tough nuts who think they ought to be spending time with Portia and co instead of me. I’ve lost count of how many lockers I have ‘accidentally’ banged into, or the number of times when I’ve slipped or tripped over ‘something’ and gone sprawling down the corridor. ‘Something’ usually being a size ten or eleven trainer attached to a size brick outhouse body.

On the plus side, I am spending a lot of time with Portia, Amanda, Jennie and Debbie. Not just breaks and lunchtimes either, they now walk with me to and from school. There is a weirdness with that though. When I’m on my own, I skulk around in the shadows trying to keep out of people’s way, I’m silent and sullen, usually carrying my books with one hand. When I’m with the girls though, I get all animated and chatty, I smile, and I hug my books in front of me like they do. If they’ve noticed it they haven’t commented, but it's obvious to me.

Weird conversations as well, like talking about Friday — yes I’m still invited to the sleepover. There have been a couple of times this week that Amanda has snuck me into the disabled loos and given me lessons on how to do my makeup. I mean if I’m going to turn up at the party in a dress, I need to look finished don’t I? Then there’s the whole ‘what should I wear’ bit. I mean the pink dress and shoes and everything ok, but I’m not going to sleep in it am I? Jenny has this baby-doll nighty she wants me in, but I’m afraid if I put on anything too revealing, Portia’s parents might see something that could raise a lot of awkward questions.

In the end Debbie agreed to lend me a floaty chiffon nighty with enough layers that it would cover everything without seeming to and Jenny said she’d bring a fluffy pink dressing gown, like Portia's but with bunnies on it and a pair of pink step in slippers with a slight heel as well, all of it would be there waiting for me when I arrived.

It’s so strange. At the beginning of the week I was so aware of the girl inside me — Stephanie we’re calling her, but wow no big leap of logic necessary there — and I was so keen for her to come out into the light. Now that she has, it’s like Steven is withdrawing to the shadows. Before this all happened I didn’t have that many mates at school, but now I don’t have any. Not guys in any case. Everyone I used to hang out with is avoiding me — too afraid of having some new and questionable status rub of on them, I suppose — and everyone else hates me. As Steven I am afraid every minute I’m in school, waiting for the next ‘accident’ to come my way, which means I actively seek out the company of the girls. So far they seem to be cool with that, although there’s be no development on Monday morning’s moment of magnificence which tends to suggest they were doing it for Stephanie rather than Steven, since we’re both stuck in here.

They’ve even introduced me to more girls around the school, which means I’m now spending more time in female company and consequently incurring greater wrath from amongst the testosterone driven half of the population.

It’s not Steven who spends time with the girls either, but Stephanie. We don’t talk about football or cars or computer games like I used to with other lads, but makeup and fashion and gossip and even guys. I even commented on how good looking I thought Brad Pitt was the other day, completely without embarrassment too. I mean I look like a guy — apart from the eyebrows maybe — I dress like a guy, but I seriously doubt any of them see me as a guy anymore.

I’m not saying I don’t like it, but it’s frightening. I don’t want to turn into some sort of freak that nobody understands and everyone hates, but at the same time I can’t deny that I’ve actually been happier since Stephanie came out to play. I have to wonder though, whether letting the Steven side of me disappear complete into the shadows now isn’t piling up heaps of trouble for the future.

Then there was yesterday.

I walked with Portia and her friends to her house, Stephanie holding her own with the conversation and chipping in her (my?) own contributions for what we should do on Friday. We reached Portia’s house and the girls turned to say goodbye.

“So, all set for tomorrow night?” This was Portia. As hostess she was most concerned that things run smoothly.

“Oh yeah, Amanda’s been giving me some great tips with the makeup so I should look pretty presentable. I’m still worried that your parents will recognise the dress though.”

“Oh I’m sure they will, but that’s cool ‘cos I already told them you borrowed it.”

“So if I’m returning it tomorrow, what do I wear when I leave?”

“Oh, that’s covered,” Jenny put her hand on my wrist as she spoke. “I’ve packed a number of outfits so you get to choose. There’s this darling yellow sundress. I’ve barely worn it, but I think you’ll look fantastic in it.”

“I can’t wait.” I really couldn’t, I mean it. “Oh I don’t have any nail varnish. I don’t suppose I could borrow some of that stuff we used last week?”

“Got it right here.” Debbie was already rummaging in her bag, and in no time handed over the bottle.

“Well I guess this is it then. I’ll see you guys at school tomorrow, then — squee — in the evening too.”

Yes that really was a squee, complete with arm gestures, excited face and everything.

We hugged and air kissed then I turned to walk the extra half mile home. I wasn’t aware at the time, but the girls watched me go. By the time I reached the end of the road I was slouching, head down and miserable, Steven back in control.

-oOo-

Back home I slammed the door back into its hole. For a moment there seemed to be no-one home, then…

“Steven, can you come upstairs please?”

There was an odd tone to Mum’s voice and my heart turned to ice as I realised she’d called me from my room.

Mum almost never goes in my room and when she does it’s usually only a quick look round to make sure I’m keeping everything tidy. Kind of our unspoken agreement, as long as I keep the dirty washing off the floor and all my stuff put away when I’m not using it, she has no reason to invade my privacy. What are the chances she breaks the détente this week?

I climbed warily up the stairs and peered around the door. Sure enough, the dress was hanging on the wardrobe door. My heart sank even deeper into the bedrock of my soul.

“Is there anything you’d like to tell me Steven?”

I let out a long sigh and sat down next to her.

“It started out as a dare…”

“…and so she and her friends turned out to be pretty cool and we’ve been hanging out pretty much every spare moment this week. They’ve invited me out again tomorrow night, as Stephanie.” It seemed best not to mention that it was a sleepover, not at this stage anyway.

“And how do you feel about this?”

How could I explain this? The Steve me never was any good at it.

“Mum, would you go back downstairs for a while. I need to show you something. It may take me some time, but I think it’ll help you to understand.”

She looked at me worried, but agreed. One last glance at the dress then she was gone.

I let out an explosive sigh and steeled myself to do this. It wasn’t going to be easy. It took me a little over an hour in the end, with showering and washing my hair in mums smellies, then trying to style my unruly mop into a passable feminine style and doing a half decent job of the makeup. The easy bit was getting into the dress. I stood in front of the mirror and decided it wasn’t a complete disaster. I definitely saw Stephanie peeking out towards the end.

I smoothed everything out and smiled at the girl in the mirror. I was terrified of where this might lead me, but it had to be done. Here goes nothing.

The low heels sounded loud on the hardwood stairs. A quick check told me that the lounge was empty. I stepped into the kitchen to find my mother looking fixedly out the window. It never occurred to me that she would be as afraid of this moment as me.

“Hello Mummy,” I said.

-oOo-

We talked for a long while, the Stephanie part of me and her (my) mummy (mum. Blitherage, this is confusing). I tried to demonstrate without forcing things how different my personality was when Stephanie was driving, like now, and I think she saw it. She did ask if I was schizophrenic at one stage which wasn’t helpful.

“No it’s always me. Just that sometimes I feel like a guy who is introverted, a misfit and has no friends and other times I feel outgoing and chatty and energetic and cheerful and… well… a girl. I put on a dress or I spend time with people who see the Stephanie in me, like my friends, and this is who I am. As soon as I leave them behind, the weight of the world lands on my shoulders and I’m back to being sad old Steven.”

“Are you saying your personality is defined by how people see you?”

“Not so much defined as influenced, but then that’s true of all of us isn’t it? Put yourself in the place of a beggar on the streets. Most people would sneer at you or ignore you. You’re not telling me that wouldn’t affect your sense of self-worth?”

“But this is different.”

“How so? Guys pick on me as Steven because I’m small and weedy and don’t fight back. That makes me feel lonely and rejected, makes me depressed, so everyone else stays away from me because I’m no fun and the circle is closed. No way out.

“The thing is it’s not just that. Part of what keeps me down as Steven is knowing there’s a part of me that needs to express itself as a girl. I can’t do the competitive thing that other guys do, not very well anyway, but there’s a part of my personality that loves the idea of chattering away like a girl. I get that interaction, I can do it and do it well, but because that’s the way girls behave and I’m a guy, convention tells me that I’m not allowed to do that, and that closes the circle even more.

“Last Friday I got a chance, through a freak accident of some idiot messing up a dare, of going out with a girl I really like and having to dress and act like a girl. It was like letting part of me out of a deep, dark dungeon where I’ve been locked all my life. A better part of me, a part that understands how to behave like a girl, that enjoys all there is about being a girl. And that’s me, the part I call Stephanie.”

“So are you telling me you want to be a girl?”

“I don’t know Mum. Right now the answer is yes, because I do it well and I’m accepted, at least by other girls, as a girl. It makes me feel like I fit in and it brings out the best in me so it makes me good company. Right now I want to sit here talking with you, I want to help you cook the tea, I want to do the dusting and cleaning, because sharing brings you closer together, even when it’s sharing a grotty job that needs doing. Tell me to go back to being Steve all the time and it’ll mean locking this part of me away and leaving what’s left of me half complete and unable to cope with my life. I’ll go back to my room, throw myself on the bed and mope about how impossible my life is.

“That’s not a threat, that’s just the way it is.”

Just then the door opened and my father came in. I jumped to my feet self-conscious and squirming, rooted to the spot by his disbelieving gaze, wilting under the shocked look on his face.

“Er, hello Daddy.”

Mum intervened.

“Go upstairs sweetheart, let me talk to your father alone.”

It didn’t take any more than that. I fled with tears streaming down my face.

I don’t know what she said, or how she swung it. I remember there being a few times when Dad’s voice went up a few decibels, but Mum always managed to say something that would calm things down and keep the conversation on track. They talked a long way into the night and I missed tea; not that I was particularly hungry. I was in bed and trying to sleep in the early hours when I heard their footsteps on the stairs. I heard my bedroom door open and felt more than anything the quiet presence of my father loom over me.

“No he’s asleep,” he said soto voce. “I suppose we’ll have to wait ‘til tomorrow to talk to him.”

He was gone in the morning — he usually leaves before my alarm goes off — so I spent the entire day on tenterhooks.

“What’s with you today?” Portia being something close to her usual level of sensitive. She meant well though so the rest of us made allowances.

“My Mum found the dress yesterday. I introduced her to Stephanie which went okay I guess, then Dad walked in on us and they ended up having a long talk. It was late by the time they were done, but I heard my Dad saying that he was going to talk to me later today, so I’m kind of nervous about it.”

“Hey don’t sweat it girlfriend.” Jenny was always the upbeat one in our group. “Just show him how wonderful you really are underneath and he’ll get it just like we did.”

Cold comfort really, but it was good to know I had friends backing me if things did go pear shaped.

“It’s not going to affect whether or not you come tonight is it?” Amanda asked. “’Cos that would really bomb.”

I walked on eggshells the rest of the afternoon, my hypersensitivity rescuing me from at least two unpleasant traps set by various meat heads in my year. When the last bell went, the girls offered to walk me all the way to my house. I thanked them but refused. My dad wouldn’t be home for some time after I got home, so I walked the last half mile on my own and under a dark cloud as usual.

I slammed through the door in my usual who-give-a-whatever manner, thoroughly Steven and thoroughly depressed.

“Is that you Stephanie?”

Mum’s voice from upstairs again. What did she say?

“Can you come upstairs a minute please sweetie.”

Was she in my room again? I trudged up the stairs. At least there was nothing else for her to discover.

“I’ve been thinking. You’re father wants to speak with you when he comes home tonight and all things being considered I thought it would be best if he met Stephanie for real. That being said, I thought she’d be more at ease if she had something of her own to wear rather than an, admittedly beautiful, borrowed part dress. I saw this in a charity shop this morning, it wasn’t at all expensive and I it is perfect for you.”

It was pretty; light brown floral print with a short ruched skirt. I took it reverently out of Mum’s hands and held it in front of me before the mirror, my eyes suddenly glowing. There was a pair of tan sandals to go with it.

“You’d better get washed and dressed. Do a proper job like you did yesterday for me, although I think the hair probably only needs one rinse. You have about an hour as he said he’d be home around five.”

-oOo-

So there I was, with fifteen minutes to spare, looking and feeling like a million dollars in my new — well nearly — dress and shoes. I earned Mum’s nod of approval, though she did insist on adding a few pieces of jewelry.

“Gilding the lily I feel, but we do want to make a good impression don’t we.”

I nervously flustered around for ten minutes until Mum’s patience reached its limit.

“Oh will you go and make a cup of tea for us or something. I can’t stand you flitting around like an epileptic butterfly.”

So that’s what I was doing when I heard the door open.

“Hello sweetheart. Good day?” Mum said.

“Could have been better. Is er…”

“In the kitchen.”

The tea was still brewing and wouldn’t need pouring for another minute yet. I nervously stepped out into Dad’s view, arms straight, hands clasped behind me, pushing my false breasts out for best effect.

The wind went out of him and Mum had to help him to a chair.

“Well I never. I don’t know what to say.”

I walked over to him and crouched in front of him, knee’s together, every inch the young lady.

“How did you learn to act like that? I can’t believe you’re a boy.”

“I’m not sure I am Daddy. I think that’s just on the outside. This is who I am on the inside, at least a big part. As for the way I act, Steven is the act. This comes naturally.”

“This is what you want then? We need to be clear on this, you want to live as a girl?”

Were they actually going to offer me that option? My breath caught and it took a moment before I could answer.

“I think so. This past week since this all started happening, I feel I’m happier as a girl.”

“You need to be sure Steve, er Stephanie, whatever. You need to be sure because if you do this for all the world to see there are going to be repercussions and not many of them pleasant.

“Think about how the other lads will treat you when you start going to school in a skirt. Think about how your friends at church will respond. It’s not just a case of saying ‘I want to be a girl today’ and having the rest of the world say ‘Okay.’ You will face a lot of opposition.”

I took a breath, wow I can’t believe I’m actually going to do this. I mean this would be a time to walk away if I had any doubt. The thing is, scary as my Dad’s picture of the future was, I couldn’t imagine it being worse than what my life as Steven had become.

“I think I need to try Daddy. I feel so much more alive when I’m like this.”

He let out a long deep sigh. Resignation? Acceptance? Perhaps a bit of both.

“Yes I can actually see that. It was a bit of shock this evening, but I think your mother was right to let me meet this side of you. Alright then, it appears we have a daughter dear.”

I threw my arms around him and gave him a wet sloppy kiss on the cheek. He sat back bemused.

“There are going to have to be a few changes though, and you won’t like them all. You won’t be able to wander the street where and whenever you want any more to and I’ll expect you to help your mother more with the housework.”

“Oh the tea!” My hands were up in front of my mouth, my father shaking his head at yet another feminine gesture.

“It’s all right I’ve got it.” Mum headed for the kitchen.

“Right here’s the plan. Monday morning you have an appointment to see a specialist in this sort of thing, your mother will take you. He will assess you, and as long as you can convince him, then in the afternoon your mother will take you shopping for some new clothes and a new school uniform. We talk to the school the same afternoon and if all goes well, Stephanie goes to school on Tuesday. Is that soon enough for you?”

“What about tonight and this weekend?”

“You don’t ask much do you?” Dad was laughing, that was a good sign. “Tonight you can go to your party, but I want you back by eleven and no messing about young lady.”

“Erm, I should have said something earlier. It’s a sleepover.”

Silence descended.

“And Portia’s parents are happy with this arrangement?”

“Well yes, because they think I’m a girl.”

“Tell me this isn’t just my son trying to have a night of passion with four beautiful girls.”

“It’s nothing like that, honest. I doubt they’d let the Steven part of me get away with anything of that sort in any case. It’s just a way of spending some time with my friends. Daddy I won’t do anything that would make you ashamed, I promise.”

“I’m not sure how much of a good idea this is, but ok. This will almost certainly come back to bite you if your friend’s parents ever find out that you are or ever were a boy, but that’s your decision. Tomorrow you get back here by eleven o’clock because your mum and I want to take our daughter out for lunch. Sunday it will be our son who comes to church and there may be a lengthy and quite possibly uncomfortable chat with the pastor afterwards.”

“Yes Daddy, thank-you, you’re the best.”

“Well I guess you’ll want to go and get ready to go to your party. I need a drink, and probably something a little stronger than tea if you don’t mind dear.”

Double Dare 4 - Dare to be Different

Author: 

  • Maeryn

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Novel Chapter

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School

Permission: 

  • Posted by author(s)
Double Dare 4 — Dare to be different
by Maeryn Lamonte

Steven’s parents have agreed to him trialling living full time as a girl. Knowing the response he’s had from the other lads at school to him just being a weedy guy, this could prove to be a tough decision, unless his new friends can come through for him.

-oOo-

“So let me get this straight... Your parents just agreed... to let you live... full time as a girl... and you’ll be coming to school... as Stephanie on Tuesday... Is that right?”

Amanda was one of those people who uses her tongue to concentrate, and since she was painting the toenails on my right foot a bright cherry red, every time she applied the varnish the tongue came out and there was a brief pause in her speech.

It was funny. I managed to suppress the urge to giggle, but couldn't help the way my body was shaking, and since the girls were each working on a hand or a foot, I earned a few dirty looks before they realised why I was laughing and joined in.

It had been a brilliant evening so far. Portia's mum had cooked us a fantastic meal, which we shared with both her parents. I was a little nervous to start with after Dad's warning about being found out, but the girls were covering for me like pros and it soon became obvious that they didn’t suspect a thing.

After the meal we watched some soppy romantic film, with me using my fair share of the tissues, then we had gone upstairs to Portia's room and listened to some of the CDs the others had brought. I have to tell you, dancing in a dress is the biz, especially when you're with a bunch of friends working out moves you can do together. We got it wrong loads, and giggled ourselves silly over our mistakes, then we started to get it right and laughed all the more. What can I say? It was great fun and I can't wait until we go out dancing for real.

Eventually the evening wore on and we all got ready for bed. I had to keep my bra and panties on to maintain my enhanced feminine figure, but that was small discomfort. Once we were all changed, Debbie suggested we give each other mani and pedicures and they all insisted that they do me first. So here I was, engulfed in layers of floaty chiffon, with my four friends working on my hands and feet like so many royal maids. It felt wonderful to be pampered like that, and even better to know that I would soon be helping to do the same for each of them in turn. For now I embraced the warm feeling of their friendship and tuned my focus to Amanda’s question.

“Yeah, pretty much. I have to see this psychologist on Monday to convince him that I’m better off as Stephanie, and once I've done that, my mum’s taking me shopping for new clothes and a new uniform in the afternoon.”

“We could set you up with some clothes, couldn’t we girls?” Jenny asked with the others nodding their agreement. “We've all got too much stuff anyway. You’ve seen Portia’s closet? Well Debbie’s and mine are about the same and Amanda’s is worse.”

“Wouldn’t your parents object to you suddenly giving me a whole bunch of your things?”

“Not if we kind of lend them to you on a sort of semi-permanent basis. It’ll mean that your Mum won't have to spend as much, or maybe you could persuade her to buy just one or two really nice things.”

“That’s really thoughtful of you guys. I’ll ask my mum and see what she says.”

“Why don’t we come round with a few things tomorrow?” This was Debbie. “Then at least you’ll have something to wear when you go and see this shrink of yours on Monday.”

“Oh!” Amanda's turn to say something. “Didn't I see Rebecca Summers in a new uniform this week? She's grown about three inches this term, so I think she must be too big for her old one. I think it'd be about the right size for you. Do you want me to ask if her mum wants to get rid of it?”

They more or less agreed everything without really consulting me, then fell to talking through each other’s wardrobes, choosing the things they were going to send my way. I felt a little out of it, only having seen Portia’s racks of dresses and things, but since this was for my benefit I let them have their fun. Portia was kind of quiet through everything, but I figured she had to be tired or something.

We chatted late into the night, experimenting with different makeup and hairstyles and generally having a great laugh. It was well into the early hours of the morning when tiredness took the first of us and I am so glad it wasn’t me, because as soon as we all noticed Debbie was asleep, we set about having some fun with her. I was given the makeup kit to work on her face and before long had used some of mascara to give her panda eyes and an an eye liner pencil to draw on a sort of curly moustache. Portia used almost an entire can of hairspray turning her hair into a Marge Simpson sort of affair — only without the blue; nothing we did was meant to be permanent — and Jenny and Amanda painted every nail of her hands and feet a different colour.

After that we all snuggled into a pile on Portia’s massive bed. The Steve in me would have loved it, but he was lost so deep inside me now I could barely feel him. I snuggled up against Jenny's back and felt a hand drape over me. A quick glance and I recognised Portia's slender fingers. I fell asleep in the soft embrace of my friends, feeling more at peace than at any time in my life.

-oOo-

“Hey you rotten jokers, what did you do to me?”

We all woke laughing and giggling at Debbie’s outrage. Portia dug out a mirror for her and soon she was laughing along with the rest of us. It was nine o’clock and we’d managed probably five or six hours sleep, still the first order of business was to undo the damage we’d done to our victim.

We were done by half past nine and all bundled down to breakfast in our night things. Portia’s mum was already up and preparing a feast for us. I tried to be a little ladylike with my eating at first, but then the other four descended on the food like a flock of gannets and I was hard pressed to keep up.

“So what are you girls doing today?” Mrs Allen trying to be polite.

“I actually have to get home by eleven. My parents are taking me out to lunch somewhere.”

“Well that’s settled then, we’ll all get ready, help you to look fabulous and walk you home. That okay, Mum?”

Portia was in an especially good mood today, but then I guess we all were. Amazing how great you can feel after a night of doing things together for and with each other.

Food finished, the five of us turned into a semi-naked mass of writhing limbs and bodies as we each took turns in the shower and on the toilet. There were times when my physical differences were very obvious, but the girls ignored them and made sure that at least one of them was on parent alert until I was fully dressed and ready for the day.

That presented a slight problem. I hadn't really thought that far ahead, and it wasn't until I was in the middle of dressing, that I realised how odd it would be for me to leave in the same party dress I'd borrowed from Portia. Fortunately my friends had my back, and each had brought something extra with me in mind. A brief huddled discussion, which didn't include me, and the girls selected a yellow sun dress Jenny had brought with her. It was maybe a little revealing, but it looked too good to resist. It had a high neck at the front which at least meant my beanbag breasts would be well covered, but no sleeves and a very short skirt. The beautiful day outside begged summer clothes, and in next to no time, the others were dressed in shorts, miniskirts, halter tops, crop tops; basically a lot of skin all round, which meant I didn't feel quite so naked.

We bundled out of the house at about half past ten and headed towards my home, arms linked and chatting and giggling so much you wouldn't have guessed we'd been been up half the night doing the same thing.

I don't think Mum and Dad were prepared for me to turn up with so much of myself on display, but since my friends were dressed much the same, they didn't feel able to comment. Since we were a little ahead of my be-home-by time, we were invited to sit out in the garden and drink some of Mum's home made lemonade. Jenny explained her earlier suggestion about clothes lending and we arranged a time later in the afternoon when the girls would bring around their offerings, along with Rebecca's old uniform if Amanda could swing it, then the girls left.

Mum and Dad's idea of the lunch was to see how I would react to being out in the big wide world dressed as a girl, and I pretty much passed with flying colours. I made sure I walked and sat as demurely as possible, keeping hidden those parts of me I definitely didn't want the world to see. The meal was nice, but I don't remember much of what I ate, being too preoccupied with the looks some of the men were giving me. When I realised it was because they were checking me out I went straight from nervous to thrilled without passing through any normal state of mind. Mundane things, like the taste of my food, did not make much of an impression in my memory compared to that.

The girls were as good as their word — of course — and by the end of the day the male clothes in my wardrobe had been replaced by a bulging mass of the most exciting colours and shapes I could imagine. The girls came up to my room and showed me all the things they'd brought, insisting that I try everything on then and there. In the end it took us so long Mum insisted they either go home or at least phone their parents to tell them they would be eating with us. They all stayed until about nine, by which time the impromptu fashion display was over, then while Dad dove them all home, I had a long, luxuriant bath and changed for bed. Jenny had left me with the floaty chifon nightdress I'd worn at the sleepover, so yet again I snuggled down to sleep feeling like the luckiest girl alive.

-oOo-

Of course fairy tales don't last in the real world and this is where mine ended.

Then next morning I was up early and washing away the last traces of Stephanie. Dressed in my usual tee-shirt and jeans, Steven came back to the fore. Oddly I didn't feel as angry or upset as I usually did and church was actually enjoyable for a change.

Afterwards Dad took me to have a private word with the pastor, as he'd promised. That didn't go so well and ended up with me storming out of the pastor's home in a rage. I'll tell you the details another time, but the short version is that he didn't want me coming to church dressed as a girl, and for as long as I continued to do so during the week, and my parents continued to support me in it, he didn't feel it was right to offer us communion. He said something about wanting to talk to us and pray with us to work through the matter, but by that time I was too livid to listen any more. Dad followed me out looking upset too, and who can blame him.

Then came Monday and the long awaited interview with the psychiatrist. He talked to me on my own and asked all sorts of questions about how long I'd felt I wanted to be a girl, and if I cross dressed habitually and how often. I gave him honest answers and told him frankly about how different I felt, how much happier, since I had decided to become Stephanie.

When we were done he invited Mum in to join us then addressed me directly.

“Stephanie, before I talk specifically about what you've told me and what I think about it, I'd like you to know that I am sympathetic to people such as yourself who are struggling with their identity, especially as regards their gender. It is always my intention to help my patients find a peace in their lives through whatever means necessary. I have quite a few years experience in dealing with such cases and I say what I feel is right each time, even if sometimes I know it's not what my patients want to hear.

“I'm sorry to tell you that my assessment is probably going to be something along those lines for you. Now I have no doubt that right now you are happier expressing yourself as a girl, and you are both very convincing and very attractive as such, but there are a number of things that you told me that give me cause for concern.

“This whole change to your life has happened very abruptly, and is still very new to you. It seems to be linked to your growing relationship with four attractive girls at your school, that's right, isn't it? You also told me that the initial idea for you to dress up wasn't yours as much as one of the girls'. Yes, I know you said you wanted to dress up, even though you were pretty sure they were trying to humiliate you, and you said that when this, what you call this girl inside you rose to the surface, that's when your friendship with these girls started to grow.

“I'm not going to deny that there may be something in what you have told me that, in the long term, would indicate you might be to some degree transgendered, but right now I think it would be unwise for me to recommend you start considering a reassignment to being female.

“If you feel that strongly about it, then perhaps you should look into it deeper, but I'm afraid at this stage I'm not prepared to recommend any course that takes you further down this route. I think it would be wrong of me to prescribe any form of hormonal treatment right now and, whilst I cannot stop you from doing such a thing, I think if you were to go out in public with people who know you, dressed as a girl, you will be exposing yourself to some horrible experiences. Most people don't understand and don't want to understand gender issues outside of the two normal ones, and I fear that you would experience a considerable amount of prejudice as a result. I think you are at a delicate stage in your self-discovery at this present moment, and such experiences would, I feel, be harmful to you.

“I am sorry because I know this is not what you want to hear, but you came to me for a professional opinion and this is it.

“My advice? Spend some time exploring this feminine side of your personality, as well as your male one, but do it at home and with your friends, as long as you're certain that they really are your friends, but don't expose yourself to the unpleasantness that will almost certainly follow outside your safe environment until you are considerably more certain that this is what you want.”

I couldn't speak. Tears were stinging my eyes so I couldn't even see straight. All I'd really heard was that he was saying I couldn't do this. Mum thanked the doctor for his time then gently guided me out the door.

We sat quietly in the car, Mum waiting patiently for me to say something. Eventually I found my voice.

“It's not fair. He doesn't understand. I feel so much better as Stephanie and I don't want to be a boy.”

Mum sighed.

“I'm sorry dear, but we did agree that one of the conditions of doing this would be that we follow the doctors advice.”

“I want a second opinion.”

“I know you do sweetheart, but we can't just pull another specialist like him out of a hat can we? Listen, he did suggest that you should explore this side of your personality, even if it is at home, so we should still do some shopping shouldn't we? I think we need to get you a good selection of pants and bras as well as a few different pairs of tights and leggings. With the clothes your friends have lent you, we don't really need to get any more, but if you were to see one or two outfits that you liked, then we might be able to indulge ourselves a little.”

I knew what she was trying to do and, somewhat reluctantly, I allowed her to lift me out of my sulk with the promise of some retail therapy. It felt good to have more than the one pair of undies, and we did see a cute dress and an absolutely gorgeous skirt and top which Mum bought for me without complaining. I think she secretly liked the idea of having a daughter, whatever the doctor had said.

Needless to say there was no phone call to the school, and the family discussion that evening was focused on when and where would be appropriate for me to be Stephanie.

I went to bed early that night, but even the soft caress of my nightdress couldn't ease the dull ache inside.

-oOo-

I woke early the next morning feeling stubborn. Rebecca's old uniform was hanging in my wardrobe and I ignored the boy's uniform Mum had laid out on my chair. When I went down to breakfast I was wearing a skirt and blouse under my blazer. As per school policy I didn't have any jewelry or makeup on — well maybe a little lip gloss, but that was it. Bare legs weren't really approved of so I also had tights on as well as the regulation flats. I looked like a girl, I felt like a girl, I was blowed if anyone was going to make me be anything else.

Dad, as usual, had already left for work, so I only had mum to contend with and she didn't quite have the heart to force me to do anything different. Again she sighed at me, looking at me with sad but loving eyes.

“Well kiddo, if this is something you have to do, I guess you have to do it. I'll phone the school to let them know, although they won't be impressed at having so little warning. Are you sure you can't put this off 'til tomorrow? No, I didn't think so.

“Well however this turns out, remember that we still love you.”

I marched out the house, texting Portia as I went. It felt good to be doing this and I was determined to make it work.

Portia and co had a fifth member as we walked in through the main gates to the school. I got a lot of double takes as people first wanted to know who the new girl was, then recognised me a few seconds later. Most of the lads' reactions were unsurprisingly negative, although when one or two of the more unpleasant ones actually spat on me, I was almost driven to tears.

The girls didn't know what to make of me, and a great many who had been happy to chat with me the previous week refused even to say hello to me. The few who did were awkward and flustered and disappeared in a flurry of excuses as soon as they could think of them.

The bell went for morning registration and as we went in through the main entrance, one of the receptionists intercepted me and took me to the headmaster's office where I didn't have to wait long before being called in. He stared at me with undisguised dismay. He didn't ask me to sit, but as there were a couple of chairs opposite his desk, I perched on the edge of one of them anyway.

“What's this about Steven?”

“Stephanie sir. I prefer to be called Stephanie. I've discovered I'm happier being a girl sir and I thought it was time to go all the way.”

“When your mother called me a while ago I thought this was some sort of bad joke. Is it a joke Stev.. Stephanie?”

“No sir, this is the way I feel happiest.”

“I don't think you'll feel that way by the end of the day, but very well then. We're going to have to make some arrangements for you. It wouldn't be right for you to carry on using the boys' toilets dressed as you are, and I can't let you use the girls', so you will have to use the staff loos near reception. I did manage to tell your teachers that you'd look a little different today, though I didn't know about the name so you'll have to let them know about that yourself. If any of them insist on calling you Steven you'll just have to live with it okay? You're excused games until we can figure out what to do with you and lastly, if you have any trouble with any of the other students, you're to come to reception and we'll find you a quiet room to sit in. I can't say I'm happy about this, but there's not a lot I can do about it. Alright, go on, get to your first class.”

So began an ordeal of name calling, more spitting and other unpleasantness. A lot of the boys still tried to trip me up in the corridors, but at least they weren't pushing me into lockers any more. I did get quite a few threats of being beaten or worse after school, and everywhere I went I was surrounded by hostile looks and malicious whispers.

Portia, Amanda, Jen and Debs stuck by me through break and sat with me at lunchtime, but by the end of it they were looking pretty drawn too, like they were being got at for sticking with me. We met at the gates at the end of the day and walked home together, all of us under something of a cloud. I didn't stop to chat at Portia's house as had become my habit, but headed straight home with some comment about having to wash everyone's gob out of my hair.

The next day was no better; worse in fact because I saw more of the strain this whole thing was putting on my friends. They stuck by me again, but I could see they were finding it difficult. When we reached Portia's house after school I stopped with them. They looked at me oddly, as though I weren't following the script.

“Listen guys, I really appreciate your sticking by my like you have this past couple of days, but I don't like to see you getting hurt because of me. I think it's going to be best if you steer clear of me, at least for a while.”

They made to protest, but I put my foot down. Literally, I mean girly moves or what? I didn't stay after that, but went home and changed into the pretty skirt and top Mum had bought me on Monday. It didn't help, I still felt pretty down. Mum and Dad tried to talk to me, but I didn't want to listen; it sounded to much like I told you so. I went to my room and leaked all over my pillow instead.

Thursday Rebecca Summers found out I was wearing her old uniform and had hysterics in the playground. She started screaming at Amanda because she'd been the one who collected it, 'for a new girl at the school' she'd said. I was nearby when I heard Amanda explain that she'd had no idea she was passing it on to a freak like me. I knew it was just damage limitation on her part, but it still hurt to hear her talk about me like that. I spent both break and lunch in the nurse's office that day, too upset to face the school population.

I thought I saw Portia watching me from a distance once or twice, but when I turned she wasn't there. None of the girls were waiting at the gates at the end of the day and I wandered home alone.

Friday the head called a general assembly and tried to talk to the school about acceptance of other's beliefs and preferences. His heart wasn't in it and he made a bit of a bish of it all. It was obvious from the outset that he was talking about me, and I had to suffer the glares of those around me for a full half hour, head bowed and face burning, before we were allowed to get on with the day.

The assembly ended up making break time and lunchtime worse. During the week the insults and injuries had faded to a point where I was just being shunned, but the head's words had stirred up a renewed resentment. I was back to dodging globs of phlegm and enduring taunts from the cerebrally challenge. At one point during lunch I saw Amanda, Jenny and Debbie talking to a girl who'd been quite openly friendly to me the previous week. I approached them feeling only a little apprehensive.

“Hi.”

“Oh great, it's the bride of Frankenstein.”

They all giggled, even the three I had recently thought were my friends.

“I wanted to ask you Jane,” I remembered the girl's name. “Last week you were happy to chat with me, what's changed, apart from my clothes I mean?”

“You don't think that's enough? Last week you were a guy who could talk about girl stuff, who was friends with Portia and these three. That made you cool. Now your just a rather sad little queer in a dress, and back to being all on your own. Honestly I don't blame these guys for dropping you, you're just... wrong. Come on girls.”

She walked off then. Amanda, Jenny and Debbie looked at me with a mixture of guilt and apology and followed her.

The cloud of misery that had been building all week reached saturation. It didn't burst all of a sudden sending me running away in floods of tears, but rather started a gentle and steady rain as the loneliness crowded in on me and crushed my spirit utterly. I wandered the corridors listlessly, a growing numbness making me immune to the barbed comments that followed me wherever I went. Eventually I found my way to the staff toilet and locked myself into a cubical.

I didn't hear the bell. Fourth period on a Friday had become a recent favourite of mine as it's a class I share with Portia and Amanda. Even if I had heard the bell I doubt I would have done anything about it though. I had reached the end of my rope and was about ready to let go and let the darkness take me. I don't know how long I sat there sniffling into a wad of toilet paper before I was interrupted by the outer door opening. I quietly pulled my feet up off the floor and held my breath. It might have fooled a teacher, but us kids know all the tricks

“Steph?”

It was Portia. I stayed quiet, perhaps she'd go away.

“Listen, I just walked out of a lesson to come looking for you, which means I almost certainly have a detention, plus who knows how long my dad will ground me, not to mention the social suicide I've just committed. The least you owe me is an acknowledgement of my existence.”

I let out a sigh and unlocked the cubicle.

“You should have just left me to rot. The others have and I don't blame them.”

She crouched in front of me and tried to look up into my eyes. I wouldn't meet her gaze, wouldn't react.

“I'd like a word with Steven.”

It was an odd request. I didn't understand it.

“My name is Stephanie.”

“I know sweetie, but Steven's in there somewhere as well. Can I speak to him?”

It didn't matter, Steph didn't feel like hanging about. I felt a shift inside me. My shoulders slumped in a different way and despite the skirt I felt like I used to.”

“What do you want?”

She reached forward and for the second time in just two weeks, she kissed me. As before it was a shock at first, but she had her arms around my neck so I couldn't escape. Slowly, very slowly, as though poison were being sucked out of me, I felt the week's misery lift and it dawned on me that here I was kissing the girl of my dreams.

Double Dare 5 - Dare to be Me

Author: 

  • Maeryn

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Novel Chapter

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School

Permission: 

  • Posted by author(s)
Double Dare 5 — Dare to be Me
by Maeryn Lamonte

Steven has discovered that it takes more than putting on a skirt to become a girl, and more than becoming a girl to become accepted. He thought he'd found a way to make his life better but it just got a lot worse. The question is does he have any friends left

-oOo-

The kiss ended leaving me dazed and confused. Portia led me out of the toilet and to the front desk.

“Excuse me miss.”

“Hello Portia, why aren't you two in class?”

“Sorry miss but Stephanie's really upset. I couldn't leave her.”

I was confused. Was I Steven or Stephanie?

“Oh you poor thing, you've been crying.”

Yheah, like I don't know that.

“Would you like to come over here and sit for a while?”

I clung onto Portia. She was the only life raft in the ship wreck of my life.

“It's alright dear, your friend can stay too. Portia, what's the matter with... her.” I guess the penny had just dropped. “Oh, you're that boy who wants to be a girl, aren't you?”

I nodded dumbly. No point in denying it. Suddenly she wanted me to be somebody else's problem.

“Wait here, I'll see if the headmaster is free.”

She disappeared down a short corridor and came back a moment later.

“He says to come through, both of you.”

This time he actually waved at the chairs, probably because there was a real girl present. No I'm not jealous, not much you bigot. Sorry not you, I meant the head.

“What's this all about then? Why aren't you two in class?”

“I'm sorry sir but Stephanie and I are in the same class for period four. I knew she was in school today and when I didn't see her in the class I asked a few of my friends. They said they'd seen her really upset and I couldn't leave her on her own, so I went looking for her.”

“Did you ask permission?”

“I'm sorry sir, I was too worried about Steph here.”

I guess I'm Stephanie then. So what was all that Steven stuff back in the bogs?

“And you then, Stev... Stephanie. Why weren't you in class?”

Well if I was going to be Stephanie, I might as well enjoy some of the privileges. I burst into tears. Portia put her arm around me and pulled me close.

“I'm sorry sir, she's had a really tough week. People have been tripping her up and calling her names. Spitting on her even.”

“Is this true?”

I managed to nod, but the tears were such a welcome release.

“I don't know what pushed her over the edge today sir, but you can see why I couldn't leave her to deal with it on her own.”

“Yes I suppose so. Ste...phanie, should I call your parents?”

“M-m-my m-m-m-mummy doesn't have a car and my d-daddy works a long way away.”

“I know where she lives sir, I could take her home.”

“It's not as simple as that I'm afraid. I can't let you leave school early unless one of your parent's comes and collects you. Would you like me to call your mother?”

I didn't know how to answer. All I knew is that I wanted Portia there. She was all that was holding me together right then.

“I think it would be a good idea sir.” Portia taking control again. Then to me, “I'll come round and see you after school if that's okay.”

I nodded, but clung to her all the more strongly. The head's face was twitching. I could almost hear the words in his head. Something unhelpful like 'pull yourself together boy and stop acting like such a girl.'

“Okay, then I think you two had better wait in the nurse's room. Who's your teacher this period?”

“Mr Jensen sir.”

“Mr Jensen. I'll have words with him, let him know what you were up to. We'll let it go with a warning this time, eh Miss Allen? But next time you get permission before you leave a lesson.”

“Yes sir, thank-you sir.”

Yeah, like any teacher would let someone leave class because one of her friends was upset.

“Okay, go wait in the nurse's room. Portia, when the bell goes I expect you to go to your last lesson alright? That's whether or not Ste..phanie's mother has arrived and whether or not h..she is fit to be left. The nurse is around somewhere and there are other staff members who can look out for h.her. You need to be in lessons.”

“Yes sir, thank-you sir.”

It's kind of a game you play with them. Teachers I mean. They know you don't mean it when you say the words, but as long as the words are right, there's nothing they can do about it. Portia was a master at the game because most teachers couldn't tell if she was being genuine or cheeky. We retreated from the head's office and went in search of the nurse's station. Still empty so either an emergency elsewhere on site or she was off hiding somewhere sucking on a cancer stick. Either way I suppose you could count it an emergency.

“Are you going to be okay Steven?”

Oh so I'm Steven again now? I think she noticed the slight huff. Girls are sensitive to things like that and good at guessing the reason.

“Look it's easier not to twist things too quick for adults, they don't like sudden change. You came to school on Tuesday asking to be called Stephanie and that's how you've been all week. If I start calling you Steven now they'll just get confused. Besides it's still your choice who you want to be. I'm just hoping you'll let me talk to you about it sometime real soon.”

“How about now?”

The bell for final period went off just then. Talk about lousy timing.

“Look, I gotta go fetch my bag and apologise to Butt Face before going to maths. I'll come round as soon as school's over if that's okay?”

The idea of Portia coming round this afternoon was very welcome. I gave her a weak smile and a slightly stronger nod before she ran off.

Oh, I should explain; Butt Face from Button as in Jenson Button. Formula one driver? Mr Jensen is Butt Face.

-oOo-

It was getting on for five o'clock by the time Portia came round. She'd popped home to drop off her bag and change, then spent ten minutes explaining to her mum exactly who was upset and why before she could wiggle out the door.

I was lying on my bed wearing a pair of jeans — no, they were Steven's; the girls ad only lent me skirts and dresses — and the top my Mum had bought me on Monday. The bra was off and my pseudo-boobs were somewhere in the corner of the room where I'd chucked them. They weren't part of me anyway.

No I don't know why I chose that top. It was soft and a really pretty colour and it smelt nice. Any or all of the above.

Anyway Portia knocked on the door and stuck her head through with a soft, concerned 'hi'.

“Your mum wants to know if you'd like anything to eat or drink. She's kind of freaking out downstairs you know? Ooh wow, nice top.”

“Yeah, it has a skirt that goes with it.”

I went to the wardrobe, unhooked it from its hangar, held it in front of me.

“Well come on girlfriend, let's see it on.”

I shrugged and dropped my jeans. Underneath I was wearing a pair of soft, white cotton panties with embroidered flowers on and a pair of nude, satin sheen tights. They were the same underwear and hosiery that I'd worn to school today. They felt nice so I hadn't bothered to change out of them. The skirt slid up and into place. It fell to mid-thigh in generous folds; not that long, but it looked really good.

“Wow that really suits you. You have great legs you know.”

I slumped back down onto the bed, as confused and dejected as ever.

“I don't get it. Are you here for Stephanie or Steven?”

“Neither. Both. It's kind of confusing. Look your mum's made more of that lemonade. I don't know about you, but I'm thirsty. Shall we go downstairs?”

“Like this or should I change?”

“Whatever makes you feel most comfortable, and I suppose least like either Steven or Stephanie.”

“I don't understand.”

“I'm not sure I do, but I think between us we can figure something out. Look I'm going to go back downstairs and leave you to decide, but don't take forever over it because if you're still up here in ten minutes I'm coming back up and I'll drag you downstairs whatever state you're in, even if you're stripped to your bra and panties.”

There was a good natured twinkle in her eyes as she said it, but I found myself believing every word.

Once I was back on my own, I thought about things for a while and decided that there was a reason I had dressed as I had that afternoon, so I exchanged the skirt for my jeans again then followed my visitor downstairs.

I found her chatting to my Mum in the kitchen, a half glass of lemonade in her hand. I filled one for myself from the jug on the table, causing them to turn round. My mum's eyes were red and puffy and I felt pang of guilt, knowing full well that I had caused of her tears.

“Hi sweetie.” She snuffled into her tissue and braved a smile. “Why don't you two go outside and enjoy the weather while it lasts?”

Fine by me. Our garden wasn't overlooked so there was no chance of anyone seeing me in my mix and muddle outfit. I slipped on my school flats, for want of something better to put on my feet, and Portia and I stepped out into the garden.

We sat in silence for a while, me totally lost in the turbulence of my own thoughts, Portia trying to put hers in order. There was no question that she was going to be the first person to speak here, but bets were being taken as to exactly when that might be. She seemed to reach a point of commitment.

“I don't know if you've noticed, but I've changed a bit over these past two weeks as well.”

Now that she mentioned it there was something different about her. I suppose before all this had started she had been gliding along in social strata so far above my own sub-bedrock levels that I hadn't really taken the time to notice her that much. I'd heard people talk about her through and I didn't see anything of the callous bitch they'd described.

“I guess, but I didn't really know you before two weeks ago.”

“No I suppose you didn't. I'm kind of glad in a way because I wasn't a very nice person. Life has a tendency to do that to you if you're not careful.”

“What do you mean?”

“Well... I didn't ask to be popular you know. It's just that I'm kind of good looking which makes me a bit of a hunk magnet, so all the girls want to know me and be like me in the hope that something of it rubs off. The thing is having everyone in the school wanting to be friends with you isn't all it's cracked up to be. You get to realise that the reason people want to be with you is so they can get something from you, so you start hanging out with the people most like you — aka Amanda, Jenny and Debs — and you develop a kind of a buffer against everyone else.

“The guys are worse. The hunks seem to fit into two categories. Either they're Neanderthal sub-humans whose idea of a good time is drinking beer and farting, or they're self-absorbed narcissists who expect you to be grateful for letting you be in their company; and yes I am aware of the irony in that statement. The rest of the male population seems to lose the power of coherent speech and/or become spectacularly clumsy whenever they realise I'm around. So you kind of become a bitch by way of self-defense.”

“Okay.”

“When Matt and Jon suggested setting you up over the dare thing, all I knew of you was that you were a prime candidate for the babbling senselessly, trips over his own feet type of loser, and I really didn't feel any qualms about going through with it and humiliating you. It would kind of act as a warning to others like you to stay clear. I'm afraid I didn't really see you as a person at all.

“But then you really surprised me. I knew you'd agreed to do anything I said if I said I'd go out with you, and the whole 'you gotta wear a dress' thing was just me getting warmed up. I don't know quite where I was going with it, except that it was going to be utterly bad for you. But you took control. I was expecting you to be all like 'whoah, no way' and going red and stuff, but you turned it around by agreeing straight away and setting a few conditions of your own.

“None of the guys I've ever been with would have been prepared to do anything so self-belittling just to spend some time with me, and I wondered if maybe you weren't such a loser after all. I mean when we got you round to my place and dolled you up, the four of us still had it in mind to make things as embarrassing as possible for you. After all you might still turn out to be a wimp and it's best not to set yourself up for a disappointment. So we made you as pink and frilly and sweet smelling as we could, and you surprised us again. Instead of turning into this totally humiliated boy in a dress, you really got into the whole evening. So much so that the other girls wanted to tag along with our newest girlfriend to see how it would go, and you agreed. What had started out as a really weird pseudo-date became a great girls night out. I mean you didn't even try to make out with me in the cinema as we'd agreed, and you don't know how much you went up in my estimation when you chose not to do that.

“We heard about what Matt and Jon had done, they even sent us the photos. You were so convincing that you really had to look to see who you were and that you weren't a girl. I knew they were going to take their revenge on you, so the girls and I decided to turn the whole thing back on them with our little stunt on Monday morning. We kind of did it for Stephanie who had been such a good sport. Since she and Steven were stuck in the same body, we figured helping one would be helping the other.

“Then there was the sleepover. There was something about you, the way you made the whole of Friday evening so much fun. I didn't want you to sink back into the social netherworld, but I couldn't figure out how to keep you around, until Amanda suggested that Stephanie should come to the slumber party, and that was just perfect. You already had the dress on you and we could spend the week coaching you and getting you ready to be all girl again in front of my parents. When the Stephanie side of you started coming out at school, even with you being obviously a boy, I didn't know what to make of it. Then at the sleep over, not only were you so totally girl that all our plans to cover for any little mistakes you might make became totally redundant, but you went on to tell us that your parents had agreed to let you try being a girl full time since it seemed to made you so much happier.

“The others were so excited. They liked Stephanie. Well let's face it, they never really met Steven like I did in the cafeteria. They wanted to help you in every way possible, lend you the clothes, get you the girl's uniform and everything. I don't know, something didn't feel right to me but I couldn't figure out what. You were so excited at the prospect of becoming someone different though, I couldn't not help you, even with my misgivings.

“I asked the others to stand by you on Tuesday and they didn't take any persuading, but then we didn't expect that big of a reaction. I had no idea we had so many jerks in our school. I mean I remember when that Downs kid came a few years back and there were a bunch of idiots who gobbed on him too. That was horrible, but I didn't do anything about it back then either. Eventually his parents had to take him out of the school and find somewhere else for him, do you remember?”

I nodded. We'd both been a lot younger then and not in any position to stand up for him in any case, but I remember my anger and frustration at what the kid had gone through. He was happy and friendly when he first arrived. Not so when he left. I guess I had first-hand experience of what he experienced now and it brought tears to my eyes as I thought about him, even worse equipped to deal with the persecution than I was.

“I knew the girls were finding it tough, going from being the most popular in the school to virtual outcast by associating with you. We all would have stuck by you if you hadn't told us to leave you alone on Tuesday. I hope you don't hate Mandy, Debs and Jen for the way they've been talking about you this week. I know you've heard some of it and it must have hurt. They feel horribly guilty about it, but they can't cope with being side-lined and the only way back into social approval is to show that they have nothing to do with you anymore.”

I shook my head.

“I know. The whole reason they're having to fight their way back in is because they stuck by me in the first place. You're right it hurts, but I don't want them to suffer because of my decisions and my actions. This is kind of my fight and I'd rather my friends didn't get hurt over my actions.”

She kissed me on the cheek and smiled through her tears.

“You're amazing, you know that? I was so right about you.”

I raised a hand to my cheek, still unsure exactly what I'd done to deserve that.

“What do you mean? How were you right about me?”

“You're an amazingly strong and selfless person. You have guts enough to hold your own even when the whole school's against you, and you put yourself in other peoples shoes; try to understand how they feel, why they behave the way they do. You don't judge people on the way they make you feel. You are such an incredible, incredibly beautiful person.

“I think that's why I've fallen in love with you.”

How is it that my response to a statement like that felt so much like dread? Is it because I didn't dare believe it, because when something this wonderful comes along, it's usually followed by something equally dreadful, or is it just that I'm so afraid I'm not the person she thinks I am and I can't face disappointing her?

She reached over and took my hand.

“I realised what it was that made me feel so unsettled at the sleepover, you know when you said that you were going to become Stephanie full time.”

“What?” I still couldn't believe she was holding my hand.

“I realised that while I liked Stephanie, I actually loved Steven. Then I realised even that wasn't it totally.”

“I'm sorry, I'm lost here.”

“We saw you change back from Stephanie to Steven quite a few times when you left us round my place. It was kind of a physical transformation, almost. You'd start off being bright and perky, standing straight, smiling, joking with us, and by the time you reached the end of the road you were slouched, head down, hiding from the world and so sad and angry. We made the mistake of thinking it was either or, which is why the girls at least were so keen to help you become the Stephie we all knew and care about. I think I only finally figured out this week when I saw you falling apart under the combined onslaught of nearly the whole school that you aren't Stephanie, and you aren't Steven either. You're both of them. If you try to be either one on his or her own, you're only acknowledging part of yourself.

“As Steven you keep part of yourself hidden away because you realise that no-one will accept her. Because there is a her in you Stevie. She's not all of you, but she's a big enough part that you can't keep her buried. But you can't let her take over either, because, while she's fun to be with, she doesn't have Steven's resilience. I suspect she might have a tendency to be judgmental as well if she were allowed.

“Like I said, I fell in love with Steven, and I really like Stephanie, but I'm afraid if you keep those two parts of yourself separate, you'll tear yourself apart and you'll never find either happiness or acceptance. Except by me of course, I love you as you are, but I would so very much love to see you how you could be.”

“So what are you asking me to do?”

“Oh, you are so thick sometimes. Be Steven. Be Stephanie. Be them both at the same time. Look you don't really fit in as Steven because you only show half of who you are. You definitely don't fit in as Stephanie because most of the people we know have their heads so far up their backsides that they can't even conceive of a beautiful, wonderful girl existing inside the body of a man. So if they're not going to accept you in either of the guises that you put forward for their approval, I say stuff the lot of them. Be who you really are and stop trying to fit in. If I've learned anything at all from being Portia Allen it's that people stop trying to make you into something you're not when you find the inner strength not to be so affected by what they think or say.”

“So I shouldn't come to school as Stephanie?”

“You should come to school as Stevenie, or whatever we're going to call the combined you. It may be easier on everyone if you didn't wear a skirt, but right now we don't care about what anyone else thinks, so if that's what you need to do to be who you really are inside then go for it.”

“What if they don't accept me like that?”

“Then you will always have me, assuming you want me that is.”

I lifted her chin and leaned over to kiss her. It was the first time I'd actually initiated contact and it was going to be memorable. When we came up for air, she was smiling her smile, more brilliant than the sun.

Mum chose that moment to stick her head out the window.

“Does Portia want to stay for tea? We're having lasagne.”

Her smile defied all laws of physics and actually grew wider.

“I'd love to Mrs Palmer, just let me phone my Mum to check if it's okay.”

While she was dialling home I snuggled up to her ear.

“Do you fancy going out tomorrow? No idea where or when yet, just exploring possibilities.”

“Can I borrow that top and the skirt that goes with it?”

“I guess it's time we found out if you look as good in my clothes as I do in yours.”

She hit me then turned to her phone.

“Hi Mum, it's Portia...”

Double Dare 6 - Who Dares Wins

Author: 

  • Maeryn

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Final Chapter

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School

Permission: 

  • Posted by author(s)
Double Dare 6 — Who Dares Wins
by Maeryn Lamonte

Stephanie survived her first week at school, but only just. She was definitely falling apart towards the end, and probably would have if it hadn't been for Portia. Still it'll probably be easier to put him/her back together the way he/she was meant to be now.

There are still quite a few loose ends left to tie up, not least amongst them being what will happen when the new Stevie turns up at School on Monday morning.

-oOo-

There aren't many things more welcome to a hungry body and an ailing soul than a large plate of lasagne. I dug in with great relish enjoying everything about this meal. If the food wasn't enough, there were the relieved and genuine smiles of my parents and best of all the comforting presence of Portia sitting ever so close beside me.

“So this means no more dressing up then?”

“I'm not sure what it means Dad. I don't think I'll be going to school in a skirt on Monday though, and I doubt I'll want to go to church in a dress either. Beyond that I can't promise anything, but you can tell the pastor you're no longer supporting my cross dressing if you like.”

“I'm not sure I understand, I thought you were through this.”

“Well in a way I am, but generally when you go through something then you end up in a different place, and that's where I am now. It's going to take a bit of exploring and there may be a few changes that I'm sure you'll want to discuss, but on the whole I think it'll end up being better. For everyone.”

After the meal, Portia and I washed up and put things away, then I wanted to take my girlfriend up to my room so we could have a bit of privacy. Mum and Dad weren't that happy about it, until I mentioned that I'd already slept in the same room as four beautiful girls and nothing had happened.

“If it makes you feel any better about it, I'll put on a dress and behave like a girl while we're up there.”

They decided that wouldn't be necessary, that they thought they could trust me, so Portia and I enjoyed an hour of uninterrupted privacy before it was time for her to go home. Dad offered to drive her, but I said I was happy to walk her, as long as the ban on my wandering around the streets late at night had been lifted. Apparently it had and we ended our evening with a leisurely stroll back to her house, and long and languorous kiss on her doorstep, which might have lasted longer still, had the porch light not gone on and interrupted us.

“I'll came round for you at about nine tomorrow then.”

“I'll be waiting. Goodnight Stevie.”

-oOo-

I slept in pyjamas that night and felt good about it. The thing about clothes is that it's easier for a woman to get away with wearing a man's things than the other way round, and both the Stephanie and the Steve inside me felt happier with this arrangement. I could feel those two different parts of myself and they were linked, like conjoined twins, inside me. They were blending more and more into one person even after such a short time, and whilst Steven would have been okay wearing a nightie if Stephanie had wanted or needed it, the reality was that right now I felt just as comfortable, if not more so, wearing my boy clothes.

I woke early, before the alarm, and dressed fully as Steven. Okay, not quite fully. I'd become too used to the pleasant feel of soft knickers and tights, so had those on underneath. I just hoped that we weren't going clothes shopping anywhere where the changing rooms were potentially exposed. I packed the top and skirt in a bag, so as to keep my promise to Portia, and stepped out of the house at half past eight. I hadn't eaten breakfast — probably nerves — but suspected I might be invited in to the Allen's, especially if Portia wanted to change before we went out. If not, we could always find a café when we arrived in town.

As predicted, Mr Allen was standing behind Portia when she answered the door. I decided on formalities first.

“Hello Mr Allen, pleased to meet you.”

“Hello erm, Steven right? You look familiar, have I seen you around somewhere?”

Awkward. Oh well, best get it out of the way.

“Er yes, do you remember Stephanie?”

“Portia's friend from last week? Oh my, yes I see it. You must be her twin. I'm sorry you must get this all the time, but you look just like her.”

“Er... yeah.”

There didn't seem to be an elegant way out of this, especially with Portia giggling in the background. I gave her the bag of clothes and she dashed upstairs to change.

“Coffee?”

“Er, tea if you have it please.”

“As long as you don't mind the tea bag in a mug sort.”

“That will be great sir, thank-you. Er milk no sugar.”

A short while later I had a steaming mug in my hands and a plate of muffins under my nose.

“Portia made them, I suspect with you in mind.”

How could I refuse? I took one and was halfway through it when Portia reappeared giving a delighted twirl. The skirt and top weren't quite her colour, but she still looked pretty amazing in them.

I quickly downed the rest of my muffin and tea while Portia gave her Dad the obligatory peck on the cheek and we made for the door.

“You know we're going to have to tell your parents before they figure it out.”

“I suppose. It's a shame though, I kind of like Stephanie being able to come round for sleep overs and come up to my room without Mum and Dad freaking out.”

“Still I'd hate for them to find out after we'd taken advantage of their trust.”

“You're no fun.”

“I know, but there are some things you don't mess with and one is your girlfriend's parents.”

“You didn't seem to mind last week.”

“Last week I was as much your girlfriend as you were mine, and it was different, even if they probably wouldn't see it that way.”

She sighed.

“You really know how to ruin a mood. You know there's going to be fallout from last week either way?”

“Yeah, I know.”

Time to change the subject before this morning gets too heavy.

“So yesterday. Your idea about me needing to be both Steven and Stephanie, how's that going to work?”

“I don't really know, but it seems a bit like you're already doing it.”

“What do you mean?”

“It's hard to put into words. It's like when you were either Steven or Stephanie you were suppressing the other part of you. Today you feel... well kind of relaxed and laid back. You're not trying to keep any part of you hidden. It's a bit like when I found you yesterday, you were already wearing some of both Steven and Stephanie's cloths together; now you're wearing some of both of their personality's instead.”

“Er, actually the clothes bit as well.”

“Sorry?”

I leaned into her ear. “I'm wearing knickers and tights under my jeans.”

“You see? You're not trying to push any of yourself away. I mean why are you... you know wearing...”

We were out in public and I guess she realised she was talking out loud.

“I guess it felt right. It was something I wanted to do and...”

“...you did it.”

“So how's this going to end? Am I going to allow myself to do anything I want until I end up being some mixed up freak halfway between man and girl?”

“No, because there's a difference between suppressing part of you because you're afraid and making adjustments to fit in with society. I mean sometimes I feel like running down the street topless — no actually I do. Not very often, but it happens. The thing is I don't because I know I don't want to live with the outrage I'd cause.

“A lot of life is about figuring out how to live with the people around you, also figuring out which of the desires inside you are right and which aren't. A lot of the time those decisions are easy to make — black and white — like I would never walk into my parent's room stark naked. I wouldn't want to shock them like that, I don't have a lot to gain from doing it and it doesn't fulfil some deep seated need. Others are more grey, where you're not convinced that other people's opinions are right. Like, I don't know, my Dad hates the twenty mile an hour speed limits near schools. Not because they're wrong. Whenever schools are in session he obeys the speed limits religiously, and especially at the beginning and end of the school day, but why should the twenty limit exist on a Sunday as well when there's no-one inside the school?

“I know, silly examples, but I wanted to give you the idea that the same kind of thing exists outside your gender issues. Now you apply the same thing to the way you are. No-one gets to tell you how you are inside. That's you, and if you try and be someone else you're going to end up the kind of emotional train wreck you were as Steven. At the same time though, you know that if you choose to live as a sort of half and half man/woman mix, you're probably not going to find any sort of happiness because one, it won't express who you really are inside and two, not many people will be prepared to accept you like that.

“I guess you are going to have to decide at some stage whether you want to live as a man or a woman, because those are the choices society offers, but whatever you decide, on the inside you should still be totally you.”

“What do you want me to be?”

“Oh no. This is your decision, please don't make it about me. I don't want to be responsible for squeezing you into another shape that's not a good fit. Besides, I probably already told you too much about the way I feel.”

“Okay, let me put it this way. If I were to decide to live as a man, because, let's face it, that's the easier option. If I were to do that, how do I stop the Stephanie part of me being squashed again?”

“You let her out, and no, I don't know what that's going to mean. It may be that there's a part of the Stephanie you that you can integrate into the persona you present to the world without them thinking you're too weird. It could be that you'll have to put on a dress every now and again and, in the right circumstances, what harm is that going to cause? It may even help. I mean that week after the dare when you were dressed as Steven but acting like Stephanie, it felt weird. I mean when we went out on the Friday, because you looked like a girl and you behaved like a girl, it was easy for us to accept you as a girl. When you looked like a boy but acted like a girl, it just felt... off.

“However you choose to live, you're going to have to find ways of keeping all of you in balance. I think a large part of that is going to involve surrounding yourself with people who love and care for you and will stand by you no matter what.”

“Like you?”

She smiled and kissed me.

“Now you're getting it, and above all, don't worry. Tomorrow when you wake up, if you feel like you totally need to be a girl, put on a dress and come round, we'll do girl stuff together. Like I said, I like Stephanie; she's fun. If on the other hand you feel like a guy, get dressed like this and I'll find something more interesting for us to do.”

“And in fifty years’ time when I have a pot belly and hair growing out of my ears?”

“We'll burn that bridge when we come to it. Who knows, I may be a hideous crone by then myself.”

“Not if you're mum's anything to go by — Ow!” She had sharp elbows.

“Were you checking my mum out?”

“Only saying that if you end up looking like her when you're older you'll still be the hottest girl around.”

“You were weren't you? Oh gah, you fancy my mum.”

The faint smile and the twinkle in her eyes reassured me that she was joking. Still if she was going to play those sort of games...

“Hey, I was just making sure I'd still fancy you in thirty years or so.”

She batted me and stuck her lower lip, so I did the same to her until she couldn't help but burst out laughing. We carried on that way for a while then settled into a comfortable silence. There was something I needed to say though.

“It wouldn't matter you know?”

“What?”

“What you looked like in thirty years. As long as you were still the person you are right now on the inside, I'd still love you as much as I do right now.”

She grabbed hold of me and we somehow managed to keep walking towards town with her trying to burrow her way inside my chest.

“Steph tell you to say that?”

“I am Steph. Just as much as I am Steven. So yeah, kind of.”

-oOo-

“Hey girly boy.”

Oh hell. Jon and Matt. I guess the mall was a hangout for a lot of guys from school, but what were the odds of bumping into these two?

“What's the matter, all your dresses in the wash, or did your mummy make you wear little boy clothes today.”

“Listen guys, you had your fun. Can't you just give us a little space now?”

“Oh I don't think so. You know we haven't forgotten how stupid you made us look a couple of weeks ago, and as for last week, I mean that was just wrong in so many ways.”

“Mind you it does explain a few things. I mean why Portia has always been such an ice cold bitch. Maybe she fancies girls. Maybe she gets her jollies from turning pansies like you into girls so she can...”

It didn't really matter who was saying what, they were both out of order. I stepped forward furiously with enough emotion showing to shut up their stream of filth.

“You can take that back.”

“Or what pansy-girl? You going to burst into tears at us?”

“Come on Steve, they're not worth it.”

Portia pulled at me arm and I allowed myself to be led away.

“Hey not so fast poofta. You're going to do something for us.”

“Why would I?”

“Glad you asked. Remember those photos we have of you dressed as a girl? Be a shame if the newspapers got hold of them wouldn't it?”

“The head told everyone that there would be hell to pay if anyone leaked what's been happening at school to the press. You wouldn't risk it.”

“I'm not talking about you poncing around school in a girl's uniform. I mean the original photos from two weeks ago when you went for a girl's night out in a frilly pink dress. That has nothing to do with the school. Put the picture of you in a dress alongside this one,” he took a photograph of me with his phone, “and the newspapers have the story they've been sniffing after all week.”

They'd probably do it as well, and get away with it. After last week I could probably handle the flack that would follow, but it wouldn't be fair on my parents or Portia and the other girls.

“What is it you want?”

“Oh it's not that hard. I mean now that you're in tight with such beautiful babes as the lovely Portia here, you can swing it so that a couple of them would go out with us tonight can't you?”

This wasn't good. I mean once you give into blackmail once you're caught.

“There is no way...”

“I guess I could have a word with Jenny and Debbie for you,” Portia interrupted me, “but you have to promise to leave us alone afterwards.”

“Oh we promise alright.” If sincerity were a place, these guys would be on the opposite side of the planet. “Oh and they've got to be ready to put out as well.”

“We'll meet you in the park this afternoon, about six.”

They backed off looking very pleased with themselves.

I turned to Portia and hissed, “What do you think you're doing?”

“Planning something. Look I know you haven't been a girl for very long, but just trust me that we aren't totally helpless, and that we will always do what's necessary to help our friends.”

She pulled her phone out and started texting. She wouldn't show me what she was doing and that had me, if anything, more worried.

We spent the morning wandering around the shops. At one point Portia asked me how I felt about having my ears pierced. It took me a moment to sort out my feelings and in the end I decided I was quite up for it. I didn't though, not then. I figured I'd put my folks through enough recently and I felt they deserved a break. There was always next weekend though, or maybe the weekend after that.

We did a lot of nothing in the Christopher Robin sense — you know, when grown-ups ask, 'What are you going to do?' and you say, 'Nothing,' and then you go and do it — and had a lot of fun doing it. I couldn't quite lose the nagging concern about what was going to happen in the park later, but every time I tried to raise the subject, Portia told me not to worry about it, that it was all taken care of.

After lunch at the local fish and chip shop, Portia decided it was time to head back.

“Amanda, Jenny and Debbie want to meet my new boyfriend,” she told me. “They want to see what's so special about you, then we have to plan out what we're going to do when those two morons come along.”

-oOo-

It was like meeting the girls for the first time, but not. They treated me like a totally different person, I couldn't do the same for them. Eventually though we got over the initial awkwardness and in no time they were chatting to me almost as freely as they had to Steph. There was a different-yet-the-sameness about the whole thing, partly down to me having Steven in the mix and partly down to them treating me differently with trousers on. We did find a new balance easily enough though and soon the same openness in our conversation re-established itself.

Jennie and Debbie had come wearing unusually cute and girlish outfits for what I knew of their normal tastes — after all I did still have a significant amount of each of their clothing hanging in my wardrobe — but I didn't really twig until six o'clock started to loom closer and the girls set about their preparations for the unholy tryst with Thing one and Thing two.

Amanda ducked out early. It seemed she was responsible for getting the two in the right frame of mind, something she was best qualified to do because her Dad owned an off license. Jenny, Debs and Portia talked through the final stages of the plot, with me listening in with growing appreciation and not a little disquiet.

“You really think they'll go for it?”

“Never underestimate the male capacity for stupidity, present company accepted of course.” Debbie blushed bright red as she realised what she had said and in whose presence.

“Stevie's enough of a girl to realise you're right, aren't you?”

I found myself nodding. Actually I genuinely thought they were right.

“I'm still worried though. I mean things could still turn bad.”

“Which is why we chose this location. It's secluded enough to put them at ease, but if you look through here.”

Portia led me over to a divide in the bushes which led to a small gate out of the park.

“In a minute or two the local and regional press will get a tip that the 'boy in a dress' from one of the local schools will be somewhere around here between six and half past. By six the street will be teaming with reporters, so if either Dumb or Dumberer gets too frisky with the girls, one scream will bring everyone running and there'll be a slightly different story to the one we planned.”

Sure enough at six o'clock things started to come together. We began to hear the sound of cars and vans pulling up in the street, just as Jon and Matt came into view. They weren't exactly walking straight either, courtesy of the six-pack of lager Amanda had liberated from the offie and left on the ground in their path.

Morality never really a strong suit with these two, they had decided that the finders keepers rule applied and had run off with their discovery. Now, with the contents of the cans shared evenly between their two stomachs, they were definitely beginning to feeling the effects.

Jenny and Debs stood to greet them and did a masterful acting job, keeping smiles fixed in place despite the beer-breath and other alcohol enhancements, and led them into the bushes. I don't know how they managed it, but in next to no time they had Jon and Matt twisted well and truly around their little fingers. Then Debbie's voice drifted over to us.

“You know this is great, but it's nowhere near as much fun as the other week with Steve, is it Jen?”

“No that really got me hot.”

“Hey what's that creep got that we don't?” Matt, or maybe Jon. It was difficult to tell through the drunken slur.

“Well it was when he got all dressed up in Portia's clothes, that made me so horny. Portia too, you shoulda seen what they got up to just after.”

“Hey that's no big, we could do that. It's a shame you don't have any spare clothes otherwise we'd show you.”

“Well we could always swap clothes. I mean that would be so much more... Ooh I'm getting all hot just thinking about it.” Jen was quite the consummate actress.

“Well I don't know...”

“Aw come on, no-one's going to see us in here. It'll be fun.”

There followed a lot of giggling and fumbling and a few minutes later Jen and Debbie came running and stumbling out of the bushes wearing jeans and tee-shirts that didn't look totally out of place on them, laughing so hard they could barely keep on their feet.

“Hey weren't those guys wearing dresses over there,” Portia said in a loud voice, closing the trap. “They ran into the bushes over there.”

A mini stampede of reporters came charging into view just as Matthew and Jonathan appeared running after the girls and their clothes. They weren't half as convincing as I had been, but they did look cute in their frills and lace. Flash bulbs were firing off all over the place and the boys were swallowed up in a whirlpool of reporters asking questions they had no way of answering.

Amanda met us outside the public bogs with a couple of carrier bags of clothes so that Jen and Debbie could change into their normal outfits.

“You know that went better than I could have hoped for,” Portia chuckled. “Those guys won't dare come after you now.”

“Yeah, I reckon by the time this has all blown over everyone will have just about forgotten Stephanie's short visit to school,” Amanda added. “I think this will work out really well for all concerned. Except perhaps for Cute and Cuterer back there.”

We all burst out laughing again.

“Okay, so what should we do next?” Jen asked as she came out of the toilet looking fresh and ready to party, Debbie following close on her heels.

“Well...”

All eyes turned to me expectantly.

“I was thinking about those dance moves we were practicing the other night. It'd be a shame to waste all that hard work.”

“Cool,” Portia's eyes were dancing with excitement. “Do you want to go like that or...”

“Well, dancing is a lot more fun when you're wearing a dress.”

“I was hoping you'd say that.”

She and Amanda grabbed my hands and dragged me into the ladies loos where a third bag was waiting. It contained makeup, shoes, a bra, some more of those homemade cup-fillers and... Portia's pink dress.


Source URL:https://bigclosetr.us/topshelf/book/25972/double-dare