Should Have Stayed in Bed

by:	Kristina.L.S.

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Rating: G	Add Review   Read Reviews, Last Review 06/20/07 (4)	Added: 06/20/2007
Complete: yes
Synopsis:	Bill was a nice guy. Everyone said so... all the girls thought he was cute as. But cute wasn't exactly what he hoped for... at least sometimes. Today was a big day, presentations... possible promotion. But well... Bill, he's having one of those days.
Categories:	Crossdressing / TV  Humor  Workplace Situations
Keywords:

Bill was a nice guy. Everyone said so... all the girls thought he was cute as. But cute wasn't exactly what he hoped for... at least sometimes. Today was a big day, presentations... possible promotion. But well... Bill, he's having one of those days.

This is a work of adult fiction. No resemblance to reality should be inferred or expected.
Copyright KLS 2007.

Should Have Stayed in Bed

By Kristina.L.S.





The radio came on at 6 with a hyperactive, bubbly, just slightly (ahem) over the top girl guy team doing their best to spruik the customer's product and edge a little higher in the ratings. He didn't really like this station at all, some of the music was ok but the announcers made him want to throw things and kick the cat... if he had a cat. Not that he actually would of course. He listened because they ran several of his teams ads. 'His team', what a joke, he was one of a half dozen junior copywriters trying to get noticed by their wit and skilful brevity.

Get the message across, make it brief, direct and memorable. That last one was the toughie.

Sighing he dragged himself out of bed determined to go for a run and shake out the cobwebs. He'd had a lousy night's sleep, much more night than sleep and was already nervous even though the meeting was hours away. His slogan had caught the boss' eye. She had smiled with a twinkle in her own as his idea was floated in the group meeting 6 days earlier. A simple line, that just skirted the edge of rude and got almost everyone smiling and nodding...'clever'.

So this morning at 11 he got to attend the presentation, meet and greet and give his line while the others sketched the campaign outline in more detail. This was what he wanted, to get noticed, a slight promotion. More money. But public speaking was never his best thing and nerves were already trying to gnaw his belly button, from the inside.

He dragged the old Olympics T-Shirt over his head, stained and worn trackie pants and his beaten up old Brooks. He grabbed the Multi-V from the fridge and took a few big gulps straight from the bottle, then patted his lips with a wash towel. He stopped still and smiled ruefully, 'Mr Macho he was not... got the sculling out of the bottle right and then went all prissy with the cloth. Should have used the back of his hand or something'. Sighing he tied his door key in the waist string and trotted down the stairs.

The sigh got bigger as he emerged on the front lawn to find his downstairs neighbour stretching in preparation for a run. He liked Carl. Carl was a nice guy... but next to Bill... well he made Bill look like his much younger brother... or even worse. He began his own stretch routine as Carl smiled and nodded his way. Damn... now they'd have to run together. What really bugged him was that Carl... adjusted. If Bill ran flat out on their usual route he would do a 35 to 40 minute circuit. Carl had mentioned before they had run together that he could do the same thing in just on 30 minutes, without really straining. Once he had discovered Bills time he never mentioned it again and in fact ran to Bill's pace every time they met up.

Standing side by side as they readied to head off the differences were apparent. Carl had two years on Bill's 22, a solid, just over 6 foot easy masculinity against Bill's slight and almost delicate 5 foot 7. Carl's trimmed almost spiky reddish blond collar length hair against Bills long and wavy, soft blonde ponytail. Standing there Bill flashed on a previous run and what was one of the most embarrassing experiences of his life... the even worse. The two of them had run 2 thirds of the circuit when a street sweeper truck had forced a temporary mark time stop. Two gorgeous girls running past on an opposing route called out in passing... "Hey Carl... who's the new girl?" He hadn't even registered that they meant him until Carl had turned his way shaking his head.

"Don't worry about those two Bill. A pair of leso's... take any chance to put down us guys." Still shaking his head side to side he headed off again as the truck cleared the road. It took another few seconds for Bill to regain his wits and catch up. Carl of course had held his pace until Bill did just that.

After they'd run a few times Carl had asked about the hair.

"Well I'm not the biggest and strongest so I need to make the most of what I have. Everyone says I have beautiful hair... and the girls just love it. It's sort of a standout feature..." he had finished lamely. Carl had nodded and smiled. That smile had not quite reassured Bill that his masculinity was unquestioned.

So they headed off, chatting idly every so often. Ten minutes along the sky opened up and within 30 seconds they were both soaked to the skin. Catching a reflection in a shop window as they waited for the lights to change Bill noted a slight difference in appearance. Carl looked sort of windswept and objectively, pretty good. He on the other hand looked like a drowned rat.

Climbing the 148 stairs from the street below to the one just behind their block he stumbled in near exhaustion as Carl trotted on the spot waiting for him to clear the final step. He'd counted those steps more than a few times, a final hurdle, before... breakfast.

If he did that more than once a week or so he might actually get fit, a stray thought quickly dismissed. Tried to ignore Carl as he waved, smiled and shook his head at the oft-repeated shaky legged stumble up the stairs. Made it inside and flicked the switch in the kitchen...

"Oh just great. No power." 'So much for a hot brekky... or coffee. At least there'll be hot water.'

After a good long soak and hair wash Bill carefully selected his outfit. He had in fact done that days ago, but here he was, second-guessing himself. The light pure wool suit was a given. It was the only one he owned. Shoes... easy, only one good pair. Shirt? Hmmm... The royal blue cotton, or the creamy white chamois silk?

He took a good look in the mirror... soft charcoal black jacket and trousers with the fluid silk shirt. Glossy black Oxfords and belt. Hair pulled back in a loose ponytail... it would dry in an hour or so. 'Not bad', now he needed coffee.

The place down the road was also blacked out so he had no choice. The half hour bus ride was even more tedious than usual not having been fortified. As always he sat and waited till the scramble to get out had slowed and then wandered out and began the 4 block walk. Having waited till now he decided to hold out till he got to Sasha's just down from work. They did a much better coffee than any of those near here and he'd tried them all over the last nine months.

His mind wandered over the coming meeting as he walked. Anxiety over what to do and say, how his idea and himself would be received and whether it might mean a jump, albeit a small one, up the ladder. Thankfully it had stopped raining but there were puddles everywhere so you needed to watch your step.

"Hallo Beelly," crooned Sasha as he came through the door. She playfully teased him about his looverly cloths and gorrrgeeus hair and called him her bootifull boy. He usually came in wearing nothing more flash than jeans and shirt, maybe a light jacket if it was cool.

He had never quite understood why but she always played up her accent to him. After he had been in a few times he had got her talking and gradually discovered she was University educated and probably smarter than he was. A Chilean émigré that had escaped to a better life after her entire family had been wiped out in a minor, long forgotten, riot. Twelve years later she was running her own little business and doing quite well.

He suspected she believed him gay and a little too shy, more than a few did. Such thoughts never bothered him as he knew who he was and it was harmless. Even the morning she had jokingly introduced him to an outrageously effeminate man that happened to be sitting and sipping as he had entered. It seemed he was a regular latecomer customer, stopping on his way to the night shift at a local gay bar. In this case he hadn't been home yet. Bill doubted he had ever blushed so much in his life and Sasha practically collapsed with laughter at his expression as... he couldn't remember the name had lisped that, ..'you should come in and say hi some night blondie. The bulls would just luuurrvvve you.'

That little encounter had almost prompted him to cut his hair. Hair that he'd kept long since he was 14. And apart from the odd moment like that he enjoyed the look and feel of it, as well he privately admitted, the slight ambiguity it gave his appearance.

Today was just the usual mild teasing that he took with good grace. He headed out the door a few minutes later with his long Columbian cappuccino. Unfortunately as he sipped he didn't notice the seemingly flat reflection of that puddle was not as light as the others. A fact that became very clear as his right foot sank to the ankle in cold water.

Stepping out and closer to the curb he began to mutter curses quietly to himself. As he shook his foot he heard a call...'hey Billy' and looked up to see Dianne coming toward him. She was his immediate boss and truth be told he fancied her something fierce. She was his height, though a few years older, a lovely bubbly brunette with a mischievous streak a mile wide. She had a slight thing for practical jokes but was always careful to keep them away from any possible serious embarrassment or humiliation. She was an equal opportunity jokester; everybody copped it from time to time. She even took it in stride when someone managed to get her back. Bill was NOT a fan of practical jokes but at least she was always 'gentle' with them. She never let anything get out of hand and could crack the whip quite effectively if she needed to. It was seldom necessary. The gang was always pretty easy going and had no major hang-ups or worries about any of their fellow workers. Gay, straight, whatever didn't really matter. They had one each side in the gay camp and Bill often suspected he fell into the 'whatever' group.

He turned further toward her to call a response as a bus cruised past close to the kerb. It was just unfortunate that a pile of leaves had caused a bank up. The resulting puddle suddenly became airborne and Bill found his mouth full of gritty water and his almost dry hair was once again saturated. He blinked once or twice and coughed the water out his nose and mouth. As he stood dripping and silently cursing the universe he noted that the lid on his cup had at least saved his coffee. He took a sip as Dianne hurried toward him, her expression showing the difficulty in trying to decide whether to laugh or commiserate. He shivered slightly as a freezing cold trickle ran down his spine.

Dianne got to him a few seconds later, stopping a pace or two back to look him up and down with mirth flickering in her eyes as she took in his bedraggled state.

"Oh dear me Billy boy, you look a sight. Um, come on, we'll see if we can find you a towel and maybe something to put on. If your lucky someone will have some spare clothing while your suit dries out. Why all dressed up anyway? Oh... the meeting right."

"Well yeah. I thought I'd go a bit more 'dressy' and look what happens. I think the gods are trying to tell me something. I should have stayed in bed."

"Oh come on. The brief glimpse I had you looked great. We have a couple of hours so maybe the Drycleaners can get you pressed and dried in time. If none of the girls has a hair dryer maybe Mag's can fit you in for a quick style and dry."

She chuckled as she saw his expression, "Maybe a facial and manicure too eh. We want you to look your best after all."

His blush caused her to laugh out loud as she took his hand and led him into the building to the lift. For some reason no one wanted to share and they had it to themselves. Something to do with the squelchy trail they left perhaps. Dianne too kept him at arms length. She felt sorry for him but was still trying, not completely successfully, to stop the giggles.

As the lift rose to their floor he glanced across at his boss and noted the pursed lips and the small hiccup as she tried to hold back a laugh. He smiled a little ruefully at her.

"I guess I look a mess huh. Go on, have a laugh. If I wasn't standing here dripping all over the carpet I'd probably be chuckling too. I just hope my suits ok, it's the only one I own. Don't want my shoes stretched out of shape either. Of course if I get a rise maybe I can afford another pair." His sideways under hair look caused her to lose it and she laughed loudly.

"I'm sorry Billy but yes, you do look a mess and it is sort of funny, as long as it's someone else of course. So you think you're up for a raise do you?" She cocked her eyebrow at him with that last question causing him to blush again. Smirking she answered herself, "...well ya never know Billy boy."

Rita was standing in the lunchroom making a tea as they headed in; she smiled and called a soft hello. Then did a double take as she took in Bills appearance. Rita was Sri Lankan though you'd say Indian if you didn't know. The slender, graceful young woman had fled an abusive marriage and now made up the girl side of their gay teammates. Paul was the guy half; he wasn't in yet.

"Billy, you need to get out of those clothes immediately, you will catch a chill. I have my tennis gear with me from my game this morning... let me get the track suit... and the socks too I think."

She bustled out and returned a moment later with a pair of pants and a hooded top in a washed out pale pink and grey. The socks were shortie ankle huggers with pink pom-poms at the ankle tendon.

"Here Billy. I am sorry it is not more masculine for you, but you will at least be dry. I promise not to laugh very much." She smiled at him as Dianne smirked in the background.

"Oh I don't know Rita. I'd say pink and grey will look just splendid on our Billy boy. Pity those shoes of yours won't fit... that big pink stripe... just loverly." She smiled widely at them both and winked at Bill to say she was just teasing. "Go on then Billy, into the bathroom and strip off. Toss your shoes up on the windowsill there; maybe they'll dry off. We'll take the rest down to the cleaners; see if they can get them dry in time. Be fun to see you walk down the road in that getup."

Her smile got wider as Bills expression turned to horror at the thought. With a laugh Dianne shook her head. Rita just smiled slightly and said nothing.

"Oh Billy, Billy. I wouldn't do that to you. I'll take them down as soon as you're stripped off. Come on then, times a wastin'."

A few minutes later a rather sheepish Bill emerged from the bathroom in a well fitting if a 'little' girly looking tracksuit.

Dianne smiled widely as Rita nodded and pronounced as precisely as she said everything. "It fits you very well Billy. I am sorry it is so girlish a style but you will at least be dry and warm until your own clothes are returned."

"Oh I think he looks just scrumptious Rita. Just a shame about the shoes, you do have tiny feet. Those pom-poms at the heel are a nice touch. Maybe I can find a pink scrunchie to set it off."

She grabbed Bills wet things and shoved them into a little white garbage bag. Smiling widely all the while as Bill shifted from rueful self- amusement to outright embarrassment every few seconds.

At that precise moment in walked Paul, a tall athletic guy that the word impeccable was seemingly made for. He stopped for a moment and took in the scene, before turning to Bill to pronounce with a totally straight face, "Trying for a new look eh Bill. Not sure it's quite you, you're more a powder blue person I think." He nodded sagely and proceeded to make a coffee.

Bill blushed, Dianne smirked and Rita just stood quietly observing.

"Well best get this lot down the road for you Bill, see if they can get them dry in the next hour or so. Back shortly."

"Thanks Dianne, I appreciate it. You too Rita, for the gear I mean."

Both ladies nodded and everyone headed to their respective desks to begin organising the day.

Over the next 20 minutes the rest of crew wandered in and after brief explanations ignored Bills outfit. Gillian, the Boss, noted the anomaly as she walked through saying 'hi' to all and sundry. She took in the wet hair and obviously borrowed clothes and assumed she would get an explanation shortly.

Funny how that goes sometimes.

It was about 15 minutes later as Dianne came back in she was waved to Gillian's office and emerged a few minutes later, called for hush and said, "..the meeting has been moved forward to 10. Everyone that's involved get it together, now. You have an hour." She then walked up to Bill.

"Your stuff won't be ready in time Billy. The earliest they could give me was 12, so we need to get something a bit more appropriate sorted."

It was Rita again that came to the rescue. She overheard Dianne and came over to Bills desk.

"It is perhaps not perfect as a solution Billy but my black suit is there at the cleaners with my white blouse. I think it would fit you quite well and is not too womanly in styling. Also the waist has adjustable tabs and will be made to fit. I am just a bit thinner than you there I would suspect. It is a solution you may consider. I have not picked it up from last week so it is ready. Then all you would need is shoes. There I cannot help I am sorry."

Dianne just stood quietly with her eyebrow cocked at him as he thought.

He knew the suit Rita was talking about. It was a nice tailored woman's jacket and trouser suit; the blouse was a crisp white cotton with French cuffs. Not exaggerated in the styling just classic tailoring. But... it was still a woman's suit.

He struggled mentally for a moment trying to make a decision. It was Dianne that posed the kicker.

"Not sure you have a choice here Billy boy. Your own stuff won't be ready in time and Gillian won't let you in the room looking like that. I think I have an idea for the shoes too. Up to you but it's either sit it out, or... Rita's suit."

He struggled mentally for another moment or two before sighing resignedly. "Ok, thanks Rita, I'll give it a try. If it looks ok I owe you one. But if I look stupid... well I guess I'm out."

Rita nodded and turned to her desk to dig the ticket from her purse. Dianne smiled at him and nodded to Rita as she headed out the door.

"Hey don't worry Billy it'll be fine. I'm sure it will look ok. Be a shame to miss this meeting, I happen to know that if Roger Donaldson is happy you will get that raise you mentioned. So..."

She watched the expression of joy followed by fear flit across his face. She felt a little sorry for him and gave him a gentle hug around the shoulders.

"Don't worry so much... it'll be fine."

He didn't need to get anything ready; he'd done that days ago. All he had to do now was sit and sweat.

A few minutes later Carole the receptionist wandered up to him.

"Hi Bill, I hear you have a slight problem, maybe I can help. Plonk your right foot up here."

She patted the edge of his desk, then as he complied she stepped back and pressed her own stockinged foot against his sole. They were almost exactly the same size. Nodding she headed back to the front counter and returned a moment later with a pair of patent slip on flats, "There ya go Billy, they should get you out of trouble for the next few hours. I usually run around the office in those rather than my heels, but I'll survive for a little while."

She leant over and gave him a peck on the cheek, leaving the shoes sitting on the corner of his desk. As he sat staring at them, admittedly they weren't too girly, except for that little bow on the edge of the instep, he became aware of one or two people watching, somewhat amused expressions evident. Blushing again he grabbed the shoes off his desk and placed them on the floor near his rubbish bin. A few quiet chuckles could be heard, he chose not to look up and see who.

'God, can this get any more embarrassing. I should have stayed in bed.'

It was just then that Cathy, the other member of this particular team came up.

"Hey ya Billy, I hear you have a problem."

She leant across and pulled his hair tie off his still wet hair. And proceeded to run her fingers through it. "Ooohh, I've been wanting to do that for ages", she grinned widely. "Come with me honey bun, I'll give you a quick blow dry in the lunchroom, must have you looking your best for old man Donaldson. You look just a pinch bedraggled at the moment and that will never do. Gillian would have you in the mail room for the next five years if you turned up looking like that."

For the next ten minutes Bill sat and it must be said, greatly enjoyed himself as Cathy ran her fingers back and forth through his hair as she gently blow-dried it. She had it all nice and styled and went to put his elastic back on, but taking one look at the sodden thing took a black satin scrunchie from her bag and used that instead.

"Perfect. There ya go Billy, lookin' good."

He stood and looked in the mirror on the wall turning a little. The ponytail was a bit higher than he usually did it, but it looked good and was dry and shiny, that was the main thing.

"Thanks Cath, that looks great, I really appreciate it."

"You're quite welcome hon. Just knock 'em dead in the meeting huh."

Just then Rita bustled in and presented him with the suit and blouse.

"Here you are Billy, try this on and see what you think. I believe it will suit you quite well and will not look out of place."

He took the plastic wrapped hanger a little gingerly and headed to the bathroom. Somewhat reluctantly he stripped down to his briefs and with a wry smile was glad that they at least were guys. Probably a good thing he wore skimpies instead of shorts. Then proceeded to slip on the blouse and button it, hoping no one would notice that it 'flapped' the wrong way, pulled on the slacks adjusting the tabs to the end buttons and then slipped on the jacket.

The shoulders were just a pinch tight, but ok. Otherwise as he stood back to get a look in the mirror it fit quite well and looked pretty good. He hoped it was just his knowledge that it was a woman's suit that coloured his perceptions. He thought he looked a bit too girlish. But...

Sighing softly he headed out to find Cath, Rita and Dianne all waiting for him. They looked him up and down and made him turn around a couple of times. Then they all looked at each other and smiled.

"Just one thing Billy boy, off with the socks they don't work at all."

Dianne took the tracksuit from him and proceeded to fold it up as Rita handed him a little packet. He glanced at it and went pale. Anklet stockings in 40 denier, black.

Rita shrugged in gentle apology, " I am sorry Billy but that is the best we can do, they will look very much like socks and will not be likely to cause any stretching of Carole's shoes."

Nodding resignedly he returned to his chair and pulled off the pink and white socks, slipped open the packet and gently pulled the anklets on and tried to believe they were in fact just very fine socks. Then he slipped on the shoes and stood again so the girls could get a look.

They all smiled and nodded approval as he stood and turned at a gesture from Dianne.

"Ok guys Billy's sorted, I hope the rest of you are ready, 20 minutes."

He sat and quietly fretted as the others went about the final pulling together of folders and double-checking the laptop link on the internal server and screen. Mostly just nervous fussing that accompanied any presentation slash proposal to a client.

It seemed like only a couple of minutes later that Gillian led 3 well dressed and fit looking men through to the conference room.

Roger Donaldson was a big, gruff but gentle man that ran his company like a family business. It worked very well for him, so he stood just inside the door with Gillian and greeted each member of the presentation team as they came in, smiling a greeting and a rumbled 'hello' to each, he had met most of them before. As lastly Dianne led Bill through the door, she was called up short as Mr Donaldson nodded to her with a murmured 'Dianne' and smilingly took Bills hand, "... and this young lady is? I don't believe we've met."

Gillian stood momentarily speechless with a raised eyebrow look, that for her, was akin to shouting...'just what the hell is going on?!'

She looked at him and still with that questioning, not quite angry look, "Bill?"

Roger Donaldson looked momentarily surprised, until Dianne took Bills other hand, "Bel, short for Belinda, meet Roger Donaldson. Belinda came up with the main slogan on this one."

Bill was almost ready to faint as Gillian's eyebrows rose a bit further and her look turned just a pinch more toward angry.

Bill managed to pull himself together and murmur quietly, "Pleased to meet you Mr Donaldson, I hope you like what we have for you."

"Oh I'm sure I shall young lady." Then clapping his hands together pronounced, "Ok, let's get this show on the road", took his seat as most everyone else did likewise and began getting themselves organised.

It took Gillian another moment to follow as she shot Dianne a look, that very clearly asked...'WELL!' Which Dianne responded to with a rueful shrug and small smile, followed by a Gillian headshake as they in turn, sat.

Then it was business as usual; this was bread and butter stuff after all. Gillian did the initial pitch and then stumbled ever so slightly as she introduced, 'Bill... Belinda', for 'her' part. After a small terrified, rabbit in the spotlight moment, Bill managed to do his bit and get across the feel and tenor of the slogan, sat as Cath took over, followed by Paul. The rest of it went by in a blur as Bill tried to maintain a low profile, read invisible and not draw any attention. The next hour and a half seemed like weeks.

Eventually Bill was roused from his introspective trance as Mr Donaldson clapped his hands together, dry washed and smiling widely looked to his two offsiders in turn, who both nodded.

"Well Gillian I think we have a go here, excellent work from your team, I'm impressed."

Gillian smiled and looked around to her people and smiling nodded to each. Including Bi.. er, Belinda. As she got to him he smiled a little crookedly and she shook her said slightly and then smiled, "... good job Belinda, I think you got your raise."

Words he'd wanted to hear so badly. But... well, not 'exactly' that perhaps. He shrugged ever so slightly and then blushed a deep scarlet. That got a smile from his Boss so he guessed he was safe, but explanations would be wanted he suspected.

Mr Donaldson stood and toasted the group with his water glass.

"I want to thank you all for the fine work you've put in on this campaign. My two colleagues here and indeed I, look forward to working with you all. Now as a gesture of respect and friendship, I believe Gillian has already asked you to keep tonight free, I wish to take the 8 of us to dinner at Tetsuya's. The table was booked 2 months ago, bloody hard to get in, too damn popular, but it is supposed to be brilliant, anyway..." he looked around the table as though checking and counting heads, then... smiling...

"Perfect, 4 boys and 4 girls. Best glad rags kids, tonight is on me and I want you all to enjoy. Two limos are booked, one for the gents and one for the ladies. Pick up times according to where you are and you'll be dropped home afterwards..."

The rest of the short speech went right past Bill as he suddenly went cold and he was sure turned as white as a ghost. 'Oh crap, crap, crap... he's counting me as one of the 4 'girls'. Now what do I do. Just what the hell else can go wrong...'

He looked up to see Dianne and Cath looking at him in quiet appraisal. Dianne had that eyebrow cocked again... now he knew he was in trouble.

The end?



Any thoughts or comments,
I can be contacted - kristinals@ozemail.com.au
Anything short of abuse welcome.