James woke up at around half nine and immediately wanted to return to slumber, knowing what cruel fate awaited him with its embracing arms of humiliation crying out to him. If he hadn't been the type of person he was he could keep his umbreon costume and tell Jessie her love wasn't worth all that much to him. He knew he'd never do this though, especially when he'd learnt all the lines he needed off by heart already and to learn other ones would almost certainly guarantee the failure on his part. He'd been eager to ring his parents and tell him of his performance, wanting to win a scrap of pride or maybe even love at the news, but now he just hoped it didn't get back to him from the parents of some of his schoolmates. His parents were distant enough from him without this unnecessary disgrace he was bringing upon himself to win the heart of a girl that wasn't the psychotic fiancée they'd selected for him. He stretched to pop a couple of stiff bones, standing up when he was refreshed enough. Panic flooded through his system when he peeled another sticker from his forehead, this time telling him she'd gone shopping to gather a few things to make him a better girl, and he could foot the bill when she came back. He swallowed nervously at her afterthought; he'd have to ring his parents and ask them for a bit of extra money to pay for whatever it was as he'd only enough to see him by for food for the next two weeks and that was tightly rationed as it was. He dressed casually, knowing he'd be changing later in the day anyway, depending when his torturer returned, and he cast a longing look at the bag that held the umbreon's outfit. Not exactly manly because it was made of spandex, but it was at least an evil character and not a girl in little to nothing in the way of attire. Suddenly he pictured Jessie in her new outfit—not quite as pleasing but still it would cling to her body—wait, if it clung to her body then everyone would know she was female, he was saved as her escape route wasn't feasible! He was safe and there was nothing she'd be able to do about it!

      He was just in the middle of deciding whether to leave learning his new lines before or after Jessie heard his inkling, when the said female walked briskly into their accommodation. She dumped a bag on the small table they possessed, telling him to strip off. She extracted a few items and it took her a few moments to realise he had yet to move from where he sat, then she quickly repeated her order. He explained his theory to her and she grunted, then informed him she'd got the situation in hand, and repeated her request with a harsher tone in her voice. He felt disheartened by this and carried out his orders, wondering how she was going to hide her body from an auditorium full of critical teenagers, no matter how well their parents raised them. Without glancing at him from her business, she requested he put on the outfit so she could figure out what she had to do to make it look like he was a girl. Two horrible thoughts split his dignity; he hated her degrading him to dressing in a skimpy girl's outfit and he wanted her to have it done as soon as possible. The other part wanted desperately for her to work on it for ages; otherwise it implied he was similar to the opposite sex, something else he didn't want.

      He'd never felt as stupid as he did then, standing in drag before the girl he wanted to impress was not a recommended route for high self-esteem. She eyed him up and stepped closer, kissing him lightly to loosen him up. When his hands were on her shoulders, she utilised her plan; she tugged at his underwear until it was at his ankles and demanded he stepped out of them. He sat on his heels and tried to reclaim them, even though it was almost completely futile as she had a grip like rigor mortis.

      "You can't wear them with that; you can't have the material coming down past the hem of the dress"

      "There is no way you're getting me to wear that without anything underneath, or something else will hang down that would be far more incriminating than boxers! I'm not Scottish, you can't make me!"

      "Now that you're finished your outburst, are you ready to listen? I never said you weren't allowed to wear anything, but you're going to have to trust me on this one okay?"

      "Depends"

      "Listen, you'll obey my every word unless you want me to cut it off myself"

      He fell quiet very suddenly and allowed her to finish what she'd started doing. He released an involuntary shiver from both the cold air and the threat she'd made. It was easy for him not to get turned on by this, as being in a dress killed the possibility entirely, in spite of Jessie kneeling and her head being at just the right level…now she was standing up. Now she was removing her own underwear…

      "NO, I'm not wearing any more drag, do you hear me?"
      "If you never lie then why did you agree to listen to me and then question your orders? You will wear these; otherwise you're even more prone to wrecking the plan than you are now. Do you want other men taking advantage of me because you couldn't dress up for a couple of hours? Remember what I'm doing for you, or rather what I'll do to you if you pull this off. And what I'll pull off if you don't"

      He ignored the last part of what she'd said and instead of thinking about neither of them wearing any underwear with the promise of them having sex that night. Well, if she kept her end of the bargain, that is. And with the thought of Jessie's height as she crouched to put the offensive item on him, his problem reoccurred, much to her despair.

      "Please stop doing that"

      "I've as much control over it as I do over my role, i.e. none at all Jess"

      "Is there anything you can do to stop it? I mean, if it happens during the play can you reverse it before anyone notices?"
      "Not a hope"

      "Anything you can do to stop it happening in the first place?"
      "Yeah, work with men"

      "Is there an option other than that?"

      "I'm not sure if you've ever heard about a little thing called mast--"

      "YES, and does it matter if it's you or someone else when the job gets done? I mean are the odds higher or lower of it happening when someone other than you did it"

      "They're about the same really, why?"

      "That's all I wanted to know and for the last time trust me"

      Twenty minutes later, James left the adjoining en suite with a look of thunder across his face. Whilst Jessie really had tried her best, her being an absolute novice and all, she'd managed to eliminate the problem almost straight away by scraping a couple of seven inch long trenches with her teeth, making him bleed almost the instant the cuts arrived. It was still incredibly tender but he returned to her making him over, in her underwear, to make sure they were prepared before the play rehearsal. He didn't need to veto wax at all it seemed, but the alternative was infinitely worse in his eyes, even though he needn't worry about anyone noticing stubble on his body after it. She'd bought him a set of black suspenders and a belt which she said was as much to cover up the fine hair on his legs as to keep the audience's eyes on his legs and not examining his chest or crotch too closely. He felt even stupider when he had them on, though he really wanted to see her in her red laced underwear with the belt, as he imagined they'd look really hot on her. There was no fear of him getting an erection no matter how filthy his thoughts got as it was sore just thinking about it, and for the first time, he was dreading the thought of sleeping with her. With her luck, she'd probably give him a vasectomy during sex or something.

      The suspenders were only the beginning of the torture she had planned for him, and it was probably the part that made him feel the straightest when compared to its stiff competition. She'd made him tie his hair back as sleekly as it would go and then she put an Alice band in it to keep the stray hair away from his face as it would be a dead giveaway to his identity. He'd hurriedly saved himself from voice training when he pointed out the only time their producers and co-workers had heard her talk was when she'd started to say she had a problem where they hadn't listened anyway, so a straight, passable falsetto as his abilities were best able to create should suffice instead of mimicking her perfectly. Then, she'd made him sit down because she wanted to put hooks on the inside of the hood to clip to the band so they needn't worry about the hood falling back or anything. She wasn't tall enough to do this standing up, and he fearfully held his crotch with both hands in case her knee hit off it as she pinioned one thigh. With this slight adaptation, the hood rested on the bridge of his nose and shadowed a lot of his face well. She ran her fingers along his face when she was finished, her soft caress sending waves of pleasure along his spine, until she opened her mouth.

      "Just as well you don't need to worry about shaving otherwise we'd have a problem with the rest of your skin"

      He irately informed her he'd shaved every other day for over a year and a half. She failed to meet his eyes again for several minutes as she could tell by his tense body he wasn't in the most affable of moods. She touched his lips lightly with her own then asked him to take it off, as she'd need to wear it herself in the dress rehearsals to make sure they weren't found out prematurely. If they were, then the damage caused by it could possibly be more catastrophic than if the truth came out later, as without a chance to prove themselves it would result in a scandal. He didn't move right away, feeling humiliated by the whole ordeal yet part of him felt like it was worthwhile since it was something she wanted. He moved his arms and pulled her closer, ignoring her knee touching his delicate area as the sweet taste of her lips more than made up for it. He still had no idea how she expected him to pull it off when the outfit ruled out stuffing until he had a chest, but he was glad she hadn't pointed out his Adam's apple wasn't very prominent. He couldn't deny that one, but it still made him feel self-conscious when she'd kept harping on about how various aspects of his body were effeminate. Her kissing became more passionate and he touched more of her this time, noting with interest she hadn't strapped herself down but because of his injury, he was unable to embarrass himself with the same problem he'd frequently suffered from since knowing her. He just wished he wasn't wearing clips in his hair as it was destroying the moment slightly for him.

      At the auditorium at the designated time, the two lust-filled teenagers joined their fellow cast members for listening to the producers telling them what to do, or more specifically, what Jessie should do for most of the time, and how her act should involve a lot of bending down and vigorous prancing. She felt inner disgust at displaying her body like that, even if the only people to see her doing it would be the production crew. James found it easy to once again deny his instincts from embarrassing him, as it would look even worse in the spandex he was wearing as part of his costume, plus he was too busy stifling laughter from Cassidy done up as an old woman to enthusiastically think about Jessie skipping about. Timothy, or Butch as he wanted to be referred to by all, looked quite respectable in the part as the weightlifting he supposedly did as a hobby plumped his muscles up sufficiently to make him look like he was a woodcutter as a profession. It was just as well it was the sour blonde he was laughing at and not him, as he was positive that he didn't want to be that person's opponent at any stage. James wasn't weak but he was far from being as strong as his muscle-bound co-star sitting opposite to him, as much as he despised him trying to see what lay beneath Jessie's outfit. If he was dressing in drag, he should be the only one to reap the rewards otherwise it made the whole thing a little pointless. The other girl looked fantastic as the mother, and it seemed she'd gained an infinite amount of confidence by getting into the character.

      When it came to practising the play itself, Jessie shot a fearful look at James when she realised she didn't know a single line for that character and she didn't have a valid reason for it. He luckily caught sight of her horror-struck face and covered up for her without missing a heartbeat, as if he'd already contemplated this possible outcome and planned a formula to work against it. She held onto her breath, only barely conscious of the men looking at her even more puffed out chest now, and that whatever James said would probably remain unheeded by the males. Especially since they liked her idea of wearing suspenders with it, it made it more interesting for them when she sat with her legs crossed.

      "Jessie has requested to save her voice for the dress rehearsal, as is a regular occurrence with most professional actors as it limits possible disasters, especially when you were so stupid as to set the play on the same day as the solitary rehearsal. Where's the time required to rectify any mistakes? You haven't allowed for it today in any event. If you have any qualms about her decision then please feel free to consult the academy I attended and tell them their star-producing system is wrong, knowing that if you do you'll lose two of your cast and my parents will want to know your valid reasons. You do know what they've done in the past don't you?"

      It seemed the producers were listening after all, as they shot each other a decidedly panicked expression, as if they knew what fate could befall them without another word from James' mouth. They both reluctantly agreed and the auditorium sprang to life as the rehearsal began. Jessie flashed him an appreciative grin and suddenly realised that he looked great in his skin-tight outfit (though less great now he wore the head of the costume) and wondered if he was wearing anything under it, as they both knew she'd have to swap with him again.

      The rehearsal consisted of little other than Jessie posing in various positions and preparing when she was supposed to jump in fright when her grandmother turned out to be an evil pokémon, as it made her body move but her dress stayed dangerously still. Halfway through the practice session, James told the producers he was going to give Jessie some private tuition to certify she'd be able to perform correctly in an hour's time. They reluctantly agreed to his condition as they could remember the threat he'd presented and so they let it be the only factor for the result where they didn't tell him to get stuffed. They longed to persist in watching her flaunt her body more, but thought they couldn't be too mean to him because he'd been the one to cast her in the first place. He led her into one of four changing rooms and locked the door behind them, craving it was something else they needed privacy for where they'd still be removing their clothing. She removed her overcoat carefully in case she knocked the pins out of place and took off her red shoes, instantly a couple of inches shorter than James, who was in the process of removing the umbreon outfit very carefully, not wanting to rip the flimsy material as it would cause irreparable trouble for them at this stage. He couldn't justify his thoughts, but he suddenly felt very vulnerable to her, and very shy about exposing himself to her even though her attire was hardly any better with all the tantalising hints it delivered.

      She sensed his discomfort and stepped closer to him, requesting he helped her remove the dress himself. He obliged, still feeling nervous at her presence. As he slid it down her body, she followed his hands with her eyes and caught sight of the heavy evidence her teeth had made on his body. She apologised and he knew what she meant from looking where her gaze was headed, feeling more out of place with her being there than before, and knowing he was about to put on the outfit she was wearing became more daunting as he suddenly understood the tickets had sold out to see a buxom lead, not a man in drag and the whole school could find out within seconds if there was any flaw in his acting or costume. She rested her body weight on her toes and kissed him, allowing his embrace as he held her against his body, and suddenly she felt nervous at him feeling her body with his torso, it was almost as if it was the final barrier overcome between them. As more heat generated in their bodies, Jessie wondered how long it would take for them to practice for the play, or if they could practice something else first.

      With little more than fifteen minutes left before the play, the couple were in major trouble. Not only was neither in any of their outfits, they seemed to have forgotten about a little thing women possess called a hymen. There was blood everywhere and they had nothing to clean themselves up with except a yard's length of white material that didn't look too clean. It was only after James used it to clean himself up a bit (he wouldn't let Jessie put it anywhere near her as it could cause her damage, not because he was selfish) that he discovered it wasn't just her blood—his cuts had reopened and spilt liquid with a vengeance. It had been a total disaster as neither had climaxed and neither had made it through without a shred of agony. In fact, both were crying at one point from the absolute pain, well, James' eyes had teared up atrociously and it was unclear whether or not any fell. Then a terrible realisation sprang into James' head; since he'd been banned from wearing any underwear and they were both bleeding, who was going to go commando? He had a horrible sinking feeling in his stomach from what he assumed the answer was and he didn't want to hear it. He assumed this is how he received unjust punishment when his parents and fiancée weren't around to deliver it personally.

      He'd held her trembling body against his own for as long as they could spare the time, and he was glad her role wasn't going to be active right away like his would be in the hope some time on her own could sedate her. He kissed her deeply and thanked her even though he wished they hadn't done anything as it wasn't remotely close to how he'd visualised losing his virginity. The only part similar to it was that it had been with her. Neither had really thought about what they were meant to do, and their mutual pain had almost stunned James as he knew their sudden lust shouldn't have been the reason for them doing it in the first place. He felt irresponsible and wished they'd rehearsed for another half an hour where they wouldn't have had the time to even consider it or put a hideous rift between the two. He kissed her again when she didn't reply, this time feeling her respond more than last time which was a relief in itself as it showed she was dragging herself out of her depression. He decided to go out on a limb and told her how he truly felt about her, and then he stood up to put the foul outfit on, hating the suspender belt even more than he had the night before. He helped his friend up, not caring that the only thing she'd done was stare at him when he'd said he loved her. She was completely right to hate him after the pain he could only begin to think he must have caused her, as he felt squeamish even at the thought of piercing almost dead-to-the-world skin like lower ears. She shakily stood up and went to put on the umbreon outfit, knowing she'd spoil it with blood and was grateful it was dark so it at least wouldn't show up easily. She just hoped it wouldn't drip through the material and leave a crimson trail behind her. She noted his attempts at getting dressed without her aid and she informed him he should have put the suspenders on after her underwear, where he pointed out his decision she needed it more, as spandex would absorb the fluid quickly and if it clotted it would stick to her and make matters a whole lot worse than if blood appeared on his costume through it—who'd be man enough to make fun of a 'girl' who was on a period without being personally grossed out? Plus it would stop people looking at him in that way if they noticed it. She smiled appreciatively and fixed her appearance as quickly as she could.

      She strapped herself down with more pressure on her chest than usual, and by the time she'd finished doctoring her appearance she looked almost masculine. She took the used cloth and as much as that action revolted her, she folded it to a certain thickness and stuffed it along her crotch to absorb more blood as much as to make here look like she possessed something in that area which she physically did not. His feet felt like he'd lose an inch or two through chafing as they didn't fit him and he hoped the stockings would ladder at the ankles to keep people from looking at the other end of his legs too closely. She commanded him to sit down and he did so, knowing he was far too tall for her to assist him otherwise. She fixed his hair with the same method she'd used that morning, checking there were no tight hairs to create a headache, ultimately distracting him to the point his falsetto would drop and he'd forget a line or something else guaranteed to construct a gaping hole in their well thought out plan.

      With five minutes left she kissed him fervently, lulling him into a false sense of security before she dropped the bombshell he'd never considered; make-up. He said he didn't need or want any as his face would be hidden by the hood, but she insisted in case the light hit him, as a sparkling eye shadow would draw attention to that and not his male features as likely as not, and since he'd have at least half his face on show, lipstick was certainly necessary. He reluctantly saw her point of view and allowed her to work on him so they wouldn't have another long argument over it as they didn't have the time to spare for it. He nearly cried with shame when he thought about him wearing a tiny dress and make-up…hang on, Jessie had gotten rid of her own chest but never gave him one! They had less than a minute to go and he still looked masculine in that sense, it was never going to work…

      She smiled as she applied the finishing touches then touched his chest gently when she was just about to get up. He jumped in fright when she did that, sending her to the floor as he did it unintentionally, as she'd activated some sort of device he didn't know she'd sewn into the insides of the dress, and two small balloon-type contraptions stopped swelling when they were the size of a convincing pair of breasts, and looked real enough to a natural woman. He was scared, not because of their sudden appearance as much as he was almost a female and hadn't enjoyed sex as a man, was she turning him gay? Would he become a transsexual after this because he became accustomed to his appearance and ways of acting throughout the play, or worse would she turn lesbian because of her strange infatuation with him in drag? He furiously prayed against both, though he was caught between two thoughts on this. If she was with another man if she decided she didn't want to go out with him anymore, he'd be forever comparing him to her and wondering how much better the new person was, but if she went out with women, even though it would be a turn-on for him, he'd think about she turned homosexual after a brief spell with him, and after sex as well. He was already in so deep it was as easy to wade further than to turn back, so no matter what happened the damage was already done. He might as well make a better woman than Jessie would have, and hope she'd learnt some of the lines so he wouldn't have to think of something to ad lib and maintain a falsetto when he thought of something to fill the gaps with.

      He opened the door again with determination as they left together, his face nicely shaded and they strode towards the hall where the curtain was down, waiting to begin and their fates would be put to the test with the following performance. The pain was subsiding in his organ, and he felt like nothing could make him show up his true gender in the play, nothing. Jessie was covered up, had the wrong types of genitalia for his pleasing and her skin tight outfit would have no bearing on him. Or so he thought, unaware of how horribly wrong it was all about to become when it was so close to perfection. They'd forgotten to check out the other props first, too consumed in their own to think about foreign factors worth worrying over.

      If only the worst part of it all was someone realising 'she' was a he within a few minutes…