School Musical Ch. 01

Authors Note: The characters portrayed in this story are 18 and completing their final year of high school. Enjoy!

*****

It was the afternoon of the school play, and I found myself upstairs in my ensuite bathroom, getting dressed as a girl.

Quite how I'd managed to end up in this situation, I wasn't sure. The general explanation was that the play had a female lead, which made things a little difficult in an all-boy school. The better explanation was that as one of the more adventurous drama students, I'd happily agreed to branch out and perform the role of Celia. The play was a modern one that had been written by a past student, and revolved around a school group trying to succeed in a dance championship. I think at most boys schools the whole idea wouldn't have made it past 'go', but Kennington had a reputation for being a little more free-thinking, and when our drama teacher ran it by the class, we'd all agreed to give it a try. Not that there wasn't the normal amount of sniggering and finger-pointing about who would make the best girl; the play needed five of them. My bigger concern was how we would handle the three main dance scenes, but for this Mr Edwards had brought in a teacher specifically to train us into some semblance of organised movement. It helped that most of the dancing was in a group; it's not that hard to look OK when ten dancers are all moving in unison.

For my part, the other main challenge was the final dance between Celia and Rodrigo, which was supposed to be quite steamy. This proved a serious problem in the rehearsals - Rodrigo's part was being played by Stuart, a classmate who had only joined the drama class recently, and was better known for his exploits on the football field and with the local teenage girls. Trying to perform a dance together had been awkward and clumsy, and I knew it was wasn't going to work. After two attempts at it, the hoots of laughter and joking from the rest of the class had become so overwhelming that Mr Edwards had been forced to get us to practice by ourselves, which was less embarrassing, but not any more co-ordinated. The practice sessions largely involved each of us stepping on feet, bickering about what was going to go where, and refusing completely to follow the teacher's instructions about how to try to look at least a little bit 'into it'. Casting Stuart was clearly a huge mistake, and I wondered how much could be attributed to his school prefect status, rather than any obvious talent. That said, there'd been virtually no volunteers at all for either lead role - the two leads were meant to fake up a lot of serious bumping and grinding, which was way across the line for even the drama class. Well, most of them.

For the performance, the 'girls' were going to be dressed in vamped-up versions of our school uniform, Brittney-style. I had asked a good friend Clara to come round and help me prepare. We'd been very close since primary school, and I knew I could count on her to help me without it being completely awkward. At the moment, we were debating the serious issue of underwear.

"Mine are just fine," I said. "Nobody is expecting it to be a complete outfit. Don't be ridiculous."

"Mike you can't go round with your Calvins under a school skirt, that will look plain stupid."

"Who's looking?"

"Dude, have you really thought about the length of that skirt?! That's the whole point of the dancing - the girls are going to be flashing underwear the whole time."

That stopped me. I hadn't really thought about it.

"Uh... oh yeah." I said, staring at the skirt she was holding up. "Now I see how that's going to look."

"Mm-hmm," she nodded, "so if you guys want it to look legitimate, you're going to need to get the whole costume right."

"OK I can see that, but I... well," I trailed off.

"Yeah well I'm glad that's a challenge for you Mike," she giggled. "If you had that problem solved you'd worry me a bit more!"

"I'm not sure what to do though," I said, "it's only two hours away..." I looked at her hopefully, thinking she'd admit it was simpler to just wing it with what I had on. But Clara was having none of it.

"I can go back and get you some from my house, if you want," she said, "but that's going to take a while, and then you're not going to get the rest of the outfit done. I think we should just grab you some of Melissa's."

"Jesus!" I said, "No way."

Melissa was my older sister, and was at her second year of university. I'm not sure if Clara had decided I was some kind of pervert.

"Oh OK, like you've never checked our her underwear drawer Mike?" Oops. Well that stopped me short.

"No...!" I started to protest, but saw her smirking at me. She leaned in closer, grinning. "Never... wondered what they feel like, Mikey?"

I could feel myself going crimson red.

"She's been away a lot this year hasn't she? I wonder if you might have even snuck in there and... tried them on...". Clara giggled at my complete and obvious embarrassment.

"Shut up," was about all I could come up with.

"It's OK," she said, suddenly all business again. "It's perfectly normal dude. I'm certain my brothers have both been going through mine." Clara had two younger brothers who would be just about that age.

"Anyway can we move on here?" I said, keen to change the conversation. "I'm not wearing Melissa's underwear. Full stop."

"OK," she said, "we've got plenty of other stuff to get done - hurry up."

We set about the process, which wasn't particularly comfortable, but at least was pre-agreed. This involved Clara showing me how to wax my legs and body, getting a wig and makeup sorted out, and then getting into her school uniform. Unfortunately another small problem occurred; as soon as I started getting my waxing done, Clara's "help" became a little too close for comfort. She of course noticed immediately that in spite of the pain of trying to rip out all my leg hair, I'd developed a serious erection. Clara and I had been very good friends a long time - strictly platonic - and I'd never envisaged being trapped in a bathroom with her, my underwear poking ridiculously out in front of me, while we tried to get me ready to wear her clothes.

"It's OK," she said quietly, and to my shock, patted me directly on the source of my embarrassment!

"Jesus! Clara!" I said.

"What? Mike, get over yourself, OK. It's normal. Just get on with it, or we're going to run out of time."

Mentally shaking my head, I did as I was told, and thankfully, we were just about ready with about 15 minutes to spare. I found myself standing with her in front of the mirror, admiring her handiwork - she'd done a great job, really. I don't think anyone would have mistaken me for a female, but the outift looked sort of cute in a way.

"Brilliant," she said, "Now just wait there a sec." She went out into my room, and after some scuffling noises, came back. To my surprise, she was twirling a pair of white cotton panties around her finger. "Ta-da! Solved." she said, and then flicked up the hem of her skirt and laughed.

I have to say I was completely speechless. What could you say at this point? I just stood there and gaped a little. Clara tossed them to me and said "Come on, get ready. I'll wait outside if that makes you feel better."

I stood for a moment, then shrugged - well, what the hell. I took off my calvins and picked up her panties. As I went to pull them on, I looked inside and realised they were even a little damp in the crotch - there was a silvery patch right in the middle. Had Clara been turned on? I wondered. I sure couldn't help it - if I'd been getting an erection during the waxing session, I was sporting an enormous one now. But at this rate we were going to be completely late. I grit my teeth and went for it, stepping into her underwear and pulling them up. Of course, even with my relatively modest penis length, there was no way those things were going to fit me properly. The back went on snugly around my ass; perhaps a little awkwardly, as the sides seemed to ride up my crack too far, but the front would barely fit over my cock.

"Mike, hurry... Oh!" said Clara, walking back in. "Well that's not going to work, is it."

I must have looked strange; makeup, wig, white blouse, stay-up tights and a shool skirt, but the front of it held up with one hand while I wondered what to do with a penis sticking out. I looked at her with a grimace, shrugging helplessly.

"OK, look I'm going to help you once here, and believe me, you owe me big time," she said. "Big time, buster." Clara stepped up against me, tugged the front of her panties off my cock, and wrapped a hand around it.

"What?! No!" I said, but her hand went immediately over my mouth. "Shut up, Mike." she whispered into my ear. "Isn't this exactly what you like? A nice, hot little hand wrapped around your cock?" She had started tugging on my cock, stroking it gently back and forth, and was breathing into my ear as she spoke.

"Don't you like how you feel in my underwear, Mike?" Stroking, up and down.

"You know, I've been wearing those all day, Michael." And up, and down. I think I might have whimpered at that point.

"They're very..." stroking

"Hot..." squeezing

"And..." jerking

"Wet..." and suddenly my legs buckled and I exploded a jet of cum into the air. Clara simply stood to one side, still jerking me quietly, until my orgasm had completely finished.

"There you go, done!" she laughed, suddenly all business again. "You can clean up, see you downstairs."

Leaving me in stunned silence, she headed down to the living room.

By the time I was cleaned up and downstairs, there was no time to even talk - we rushed to grab all our things and get in the car. Clara was helping with the lighting, so we had several boxes of her gear to fit in the car. I found myself next to no help - tottering around in a pair of heels, struggling with even the lighter boxes. Clara's friend Rosie was driving, and was no help either - she stood around sipping a glass of wine and giggling. I realised this happened mostly when I tried to pick something up, and she'd clearly noticed that not only was it making Clara's skirt ride up my backside, but the panties were also flashing every time. The sides were also riding up still, and I wondered how much of my freshly waxed ass was waving around.

I'd had enough. "Rosie, it's for the fucking play, OK?" I snapped. "If you're not helping, go outside."

"But you look so cute, Mikey!" she tittered. "I'm enjoying the show."

I gave an exasperated sigh, and got on with it. I hadn't made eye contact with Clara since the episode in the bathroom, and there wasn't an opportunity to discuss it with Rosie there. What the hell was going on, I wondered to myself.

We managed to get things sorted out just a little late, and rushed to get down to the school in time for the pre-rehearsal.

"Clara, seriously - when we get there you stay with me." I said. "I'm not walking around like this by myself."

"OK Mike" she said.

"Mikette" added Rosie.

"Shut up!!" we both said at once, and thankfully she did for the rest of the drive.

The school carpark and grounds were already bustling with kids and parents making their way in, but fortunately we didn't attract too much attention heading to the theatre hall. There was a large backstage and downstairs area, and I was thankful to see a couple of other guys there playing the female parts. Though I had to say, they'd done a somewhat half-hearted job.

"Wow... Mike you've, uh, gone all out!" said Steven, one of the 'backup dancers', who had gone for a wig and no makeup, looking pretty much like what you'd normally see in a joke video.

"Well, I'm trying to do the lead..." I said. Just then, one of the other 'girls' bent to open his bag, and I saw he was wearing literally a pair of boxer shorts. I mentally groaned, and tried to surreptitiously tug the sides of Clara's panties down over my ass a bit better. How humiliating.

Stuart arrived with some of the other actors, and surprisingly looked just as uncomfortable as the rest of us. After a minute, he came up and whispered, "Mike, can I talk to you please - out the back?" I went with him to the separate dressing room. "What's up?" I said.

"It's the dancing..." he started, then interrupted himself, "Jesus, you look... great!" He'd been preoccupied, and suddenly noticed my comprehensive outfit, which included some moulded breasts stuffed into Clara's bra. I raised an eyebrow, and he stammered "Oh, like... great for the part, haha. Fuck, I didn't mean like, great looking. You know what I mean."

"Right," I said, "Anyway - so what about the dancing?"

"I just can't do it, man. I can't dance in front of people, and with someone... I think someone else will have to do it." He looked down at his feet, which made him look strangely small for a guy who was nearly 6 foot tall and built for football.

"Stuart, I don't want to do it either - I mean look at me - at least you're not going on stage in girl's clothes in front of the whole school!"

"Yes but you can at least do your part Mike! I can't do it at all."

"Dude come on, I've seen you dancing at parties before, you're fine. The girls all like it. You gotta be doing something right."

"Yes but..." he thought for a moment, then gave me a slightly guilty look. "I'm usually drinking... I feel fine dancing when I've a few drinks, you know?"

"Right, but that's not an option..." I trailed off, as he now had a sneaky smile on his face. "Stu, you're not... what are you thinking about?"

"I've got a bottle of vodka with me - you wouldn't tell, right?"

I stood there contemplating this for a minute, and thought, well, what the hell. "Go on. In fact..." I paused, "I could use some myself." Maybe flashing your best friend's panties to the world would make a bit more sense under the appropriate influence. Stuart went out and came back with the bottle, turning the door lock for safety.

"How long til it starts?" he asked, checking his watch and taking a quick swig from the bottle.

"About 20 minutes I think. But people will want us up backstage."

"Nah, I told Mr Edwards we're practising that final dialogue we kept stuffing up".

"Oh, nice" I said, taking the bottle and gulping some. It was a fierce shock, but I already was thinking this mightn't be a bad idea.

"Dude, did you wax your legs?" Stuart said, as we passed the bottle back and forth. "You did do a really good job of the costume."

"Yeah well I had Clara to help."

"Oh right. You guys are... like..."

"No, we're not."

"OK."

There was a slightly more comfortable silence as we proceeded to swig our way through about half a bottle. By the time I was ready to go backstage, I was just about reeling, and hoped the rest of the group wouldn't notice. We dashed ot get ready, the lights came on, and the curtain went up.

I'd have to say, the first half of the musical was pretty much a blur. The dancing parts looked pretty terrible from what I could see, but as the leads, Stuart and I were trying to put up a good front and not show up that we were both well intoxicated. Thankfully, the parts didn't really call for much co-ordinated dancing - yet - and we didn't mangle all the dialogue too badly. There were the predictable whistles and catcalls from the audience, but at the end of the first part, a big round of applause, and we escaped backstage again.

"That went OK!" he said, clearly relieved.

"Yeah - hope so," I said, "I'm just not looking forward to the next part."

"Um... yep." he said, glancing at the stairs to the dressing room. I smirked.

"Mr Edwards, we're just going to cut out and re-do that scene - is that OK?" Stuart said, and got an acknowledging thumbs up from the teacher, who was preoccupied trying to sort out the backing dancers, who he'd declared were pretty hopeless. We scuttled off, and I grabbed the bottle from Stuart's bag, not paying much attention as I did it.

"Mike, what..." he said from behind me, "have you got panties on?!" Oh. Shit.

"They're... they're Clara's," I stuttered, "she reckoned everyone would wear them."

"Oh"

"Yeah. And I got here and the guys are all in boxers and stuff."

"Figures... um, do you want to borrow some of mine or something?"

I looked at him sceptically; it was pretty clear he was a larger build, and the last thing I needed was a pair of boxers falling down my hips during the dancing.

"Don't worry about it," I said, "Just don't remind me, alright? It's really embarrassing."

"It looks fine - don't worry," he said, taking a drink.

"Obviously it doesn't look fine," I said, "I probably look like a ridiculous tranny."

"No, really," he said, "that's a pretty decent outfit dude. I've seen girls with a way worse ass than that!"

"Err..." he said, "Sorry - I mean I'm just trying to..."

"Never mind, man," I said, trying to change the topic.

But in the corner of my mind, I now had the odd idea stuck in my head that maybe my ass didn't look too bad after all. Clara had of course been right, this wasn't the first time I'd tried on a pair of panties - Melissa's drawer had been raided many, many times over. But having the whole costume on display to the world with a fresh wax job made it a completely different experience. In the spirit of trying to get the dance right and not just get hammered, we had a couple of attempts at the final scene, and went over the dance steps. It felt a bit less awkward with the benefit of now being fairly drunk, although I couldn't quite work out where to put my hands, and I think Stuart was equally struggling, as my fake boobs whacked into his arm and so on.

"Stu," I said, "Look, this isn't going to be great. But just picture like we're at a party and I'm the girl, OK? Try to forget it's the school play."

"Right, I'm trying," he said, and was interrupted by a knock on the door.

"Guys - two minutes!! Get up here!" called Mr Edwards.

"Shit. OK, one more time. Like a party, OK?" I said. To my surprise, it seemed to be the right advice, and Stuart and I stepped a lot closer together, moving with some sense of co-ordination finally. We got to the part where Rodrigo finally moves in on Celia, which had him dancing behind me and getting a little steamy with his hands. I almost recoiled when his crotch brushed against me, and I was almost certain I felt his dick pressing against my ass.

"Stuart, what the..." I pulled away.

"What, man?" he'd turned half away so now I couldn't be sure I'd felt it after all.

"Uh... no sorry - I thought we'd got that move wrong," I stammered. Jesus, what was I thinking! "Come on, we'll be late."

We rushed back upstairs, bottle mostly dealt with, and got ready for the second part. One of the other 'girls' Joe caught the serious waft of vodka on my breath and laughed. "Gee you could have shared with the rest of us. We look just as silly." We both laughed, relieving the tension a bit.

The musical progressed, and I thought Stuart was doing a lot better overall - he even ad-libbed some lines, and got right into the dancing. I hadn't really paid much attention earlier, but I was sure that he must have gone through a lot more of the vodka than I had. But he was pretty well-built and muscular. As I danced in the group, I spotted Clara waving and giving a thumbs up, which was also encouraging. I grinned and got into the swing of things, hoping I wasn't so drunk I would clatter over in the heels I had on. By the time we got to the finale, I'd forgotten about the incident in the change room, and we flung ourselves into the dance, too much hooting and encouragement from the crowd, who were finding the whole thing hilarious. But now there wasn't any doubt at all about it, Stuart was 'getting into it' a lot more than planned, and I had an erection grinding into my ass as he 'pretended' to feel me up. Worse, I could feel my own cock spring to attention, which was going to be bloody obvious to the audience if I didn't do something quickly. At least he had his jeans on, although it didn't seem they were helping a great deal to restrain what was going on.