[TG] The Humbling of David - Part 1 (Commission) (Patreon)

Commissioned by dash666 on DA.

~

“Come on man, it was one rejection. You can’t keep letting it eat you up like this.”

David sighed, poking at his meal unenthusiastically; Pat had invited him out for dinner tonight under the guise of cheering him up; he meant well but it had been a terrible idea. Being the third wheel on a date was hardly the best way to get your mind of being single. What’s worse is that it was obvious from the moment he stepped into the restaurant and met the couple it had been obvious Pat had not told his wife, Rachel. She’d spent the entire meal surly, clearly annoyed that her romantic evening had turned into a boys catch up.

Perhaps the polite thing to do would have been to excuse himself and give them back their evening but fuck it, Pat was the one who invited him, why should he feel bad? They would all be having a better time right now if she just got over it and tried to enjoy herself; her mood was only making him feel worse.

He’d tried picking up one of the waitresses; nothing sleazy, just a few compliments here and there but despite her warm smiles and apparent reciprocation, she’d switched tables with another a few minutes later and was now stubbornly refusing to meet his eye.

“It wasn’t one rejection.” David said finally, “It was four. Every time I ask a woman out, I get rejected. Soundly. All because I’m not some hot to trot, gym obsessed asshole with muscles where his brains should be.”

Rachel made a face; the kind women always made when they had something to say but for whatever reason, chose not to. There was judgement in her eyes and after a shitty day and an awkward dinner David felt it lighting a spark beneath him. She was baiting him, like all catty women do. She wanted him to snap and say something rude so that when she retaliated, everybody would say he started it and take her side. Well, he wasn’t falling for it. He fixed her with a hard look in return.

“See, women have it so easy, even if they aren’t supermodels. All they have to do is smile and do their hair and boom, instant boyfriend.” He added, “If I were a woman, I’d have men falling all over me but because I am an average looking guy, I have to work that much harder to even get a second glance.”

“Maybe we should just eat.” Pat chuckled nervously, his eyes slipping between his friend and wife. David really didn’t have it in him to feel sympathetic.

“Have you ever thought,” Rachel said finally, placing down her fork, “That perhaps you might be the constant in all this? If multiple women turn you down, maybe you’re the problem. Not them.”

“The fact of the matter is, if I were a woman all I’d need to do to not be lonely is show a little boob. Men have to do all the work. I am perfectly nice. I’m decent looking, I make good money, I’m smart; what more could women want in a partner?” David argued.

“Somebody who doesn’t harass waitresses for one.” Rachel sniped.

“She was smiling, she flirted back and lead me on!”

“It’s her job to be nice to you, you dolt.” Rachel sighed as if talking to a child, “You really have no idea what it’s like on the other side of the fence.”

David looked over to Pat, was he seriously going to let his woman talk to him like that? His so called friend had buried himself in a dessert menu, stubbornly pretending not to hear the argument; whipped coward. When he caught David looking, he cleared his throat awkwardly.

“I’m just going to the bathroom.” He mumbled, fleeing the table so fast he almost ran into another waiter. David turned his ire back to Rachel.

“You’re just annoyed because nobody would ever try to pick you up.” David threw down his napkin.

Chair legs scrapped across the wooden floor, the whole restaurant fell into a hush as both Rachel and he stood. Her hands were planted firmly on the table but her shoulders were tense, David had to resist the urge to laugh; was she going to try and fight him? He’d never hit a woman, even if she did have it coming. Instead of raising a fist though, she seethed in a quiet voice so only they could hear.

“You think it’s so easy? We’ll see about that.”

Like a snake her arm shot out, palm an inch from his face where she clicked her fingers. Despite himself, David jumped, the noise and action taking him by surprise but then he scoffed, was that supposed to be scary?

“Wow, a snap. I bet you feel really cool.” He rolled his eyes, “Good evening, Rachel.”

He turned and strode out of the restaurant, ignoring the self-satisfied look on Rachel’s face as he went. Let her think she wont that argument, deep down they both knew he did. Maybe he should swear off dating all together, even the nice girls would end up shrews like Rachel one day, it was basically a rite of passage from what he’d seen. He tried to look on the bright side, at least he’d gotten a free meal out of it.  A flash in the storefront mirror caused him to do a double take; for a second there, he could have sword he’d seen something flowing behind him, like a dress or hair but when he looked back it was just his usual self-staring back. He must have been more tired than he’d realised, an early night was in order.

He kept walking, only to find himself struggling; there was a burn in his calves and a strange weight forming on his chest. His eyes went wide in panic, was this a heart attack? Frantically he tried to remember the signs when suddenly, an overwhelming sense of dizziness washed over him and David found himself stumbling forward, saved barely an inch off the ground by somebody grabbing his arm. He was lowered gently and just as quickly as it had come, the light headedness faded leaving him blinking blearily up at a concerned looking construction worker.

“Are you alright ma’am?”

“Ma’am?”

Voices whispered all around as a small crowd began to form, kept at bay by the worker. Somebody was talking about calling an ambulance when suddenly, Rachel appeared over the man’s shoulder. For just a split second, as their eyes met there was a malicious grin on her face and then, it turned into one of concern.

“Donna! Oh, dear I told you that was one glass too many!”

What on earth was she talking about?

Rachel reached down and helped him to sit, Pat appearing a moment later and passing her a cup of water somebody had fetched from a nearby shop.

“It’s alright, we’ll look after her.” Pat told the crowd.

“We had a bit too much wine with dinner is all.” Rachel laughed, forcing the cup against his lips so that he was forced to take a sip.

His head was spinning in a way that had nothing to do with the dizzy spell. She? Her? Ma’am? What on earth…?

A distorted reflection in the water, sloshing around in the paper cup. It was hard to make out but David could see the general outline of his feature and was shocked to see a dark halo of hair framing his face where before there was nothing but stubble. He dropped the cup, hands flying to his cheeks and meeting soft locks which he pulled forward; dark brown, almost black and wavy.

“Are you sure she’s okay?” The worker looked concerned, “She isn’t saying anything and what is she doing to her hair?”

“She’s a bit of a silly drunk. I’ll get her home don’t you worry, come on Donna.”

An arm looped through his own and Rachel gave him a smile, that same knowing look in her eyes.

“What have you-“ That wasn’t his voice! A hand flew to his throat and Donna smiled.

“You said it would be easier to be a woman well now you can prove it.” She whispered, pressing their heads together like he’d seen so many girls do on tv. “In this reality, David doesn’t exist, but my best friend Donna does.”

~

Pat and Rachel walked him back to his house in a daze; Rachel’s arm looped around his own the whole way. He wasn’t drunk, he’d only had two beers with dinner and yet his body felt so odd; heavier in the chest and rear, with long hair tickling his nape, and a flight sway to his hips that no matter how hard he tried, he couldn’t stop. Rachel seemed to understand what was going on, whenever Pat glanced away for a moment, she fixed him with a salacious grin that made his stomach churn with anxiety. But every time he opened his mouth to demand answers she shushed him.

“Wait till we get home Donna, I think you need to sit down.”

There was that name again. Donna. It rattled around in his skull; on some instinctual level it felt right; the name seemed to suit him somehow and yet, his name was David so how could that be? The feeling of wrongness continued when they reached his house. He shook his head slightly in confusion, taking in the flower filled garden and white brick front; it was his house, the walls and windows were all the same but the trappings were all different. It was like visiting your childhood home, ten years after somebody else had purchased it; the bones were familiar but the details were all wrong. Inside the air was perfumed with more flowers, in vases and bundles hung from string, Pat coughed slightly.

“I don’t know how you ladies stand the air smelling so sweet all the time.”

“I think it’s lovely.”

The words slipped out before he could stop them and his cheeks dusted pink. It was true, but were he not so befuddled he’d never have admitted so.

“Of course, Donna, sorry. That was a dickish thing to say in somebody else’s home.” Pat apologised, “Rachel why don’t you sit her down and I’ll go find some ibuprofen.”

He disappeared from view as Rachel sat him down on the couch, holding both his hands in hers like sisters.

“What have you done?” He whispered, “How have you done…this?”

“A little reality warping.” Rachel smirked, “I just changed a few things around that’s all.”

“How am I going to explain this to work? And why doesn’t Pat seem weirded out? Was he in on this?”

“Hush, let me explain.” She patted his hands, “Pat isn’t ‘weirded out’ because he, along with everybody else in this reality besides myself, remember you as Donna. My best friend and co-worker down at Shoeless Joes.”

David felt as though he’d been struck by thunder; he’d have laughed were it not obvious she was telling the truth. Questions burst forth, about how she’d attained such power but Rachel stubbornly refused to answer each one, instead offering him a deal.

“You think its so easy to be a woman well, here is your chance to prove your point. Find yourself a long-term boyfriend in three weeks and I’ll admit you were right; women have it easier and change you back.”

The idea of dating a man was…not appealing to say the least but he had no way to change back without Rachel and once he had been put right, nobody would ever have to know, right? Besides, getting a guy wouldn’t be that hard, bat a few eyes, laugh at a few jokes and he’d have his pick. Easy done.

“You’re on.” He hissed, confidence brimming just as Pat returned with a blister pack of headache pills ‘for the morning’.

Once Pat was convinced she was fine they moved to leave, Rachel looked confident as she bade goodnight to her ‘best friend’.

“I’ll see you for tomorrow’s lunch shift, ten o’clock, don’t be late!”

“Oh, I won’t be!”

He smirked as the door closed behind them. By eleven tomorrow morning he’d have the customers drooling at his feet; Rachel really had no idea just how simple this was going to be, he’d be back in his body before the end of his first shift.

~

Sleeping had proved difficult, at first, he simply could not get comfy. A lifetime stomach sleeper, his favourite position was all of a sudden off the cards. His breasts got sore in seconds with his body weight on them, yet when he laid on his back, he couldn’t get used to the slightly raised angle of his hips. His ass was wide, and with that wideness came extra roundness that moved in odd ways every toss and turn.

It didn’t help that he was still in the clothes he’d worn out to dinner. Stretchy yoga pants over a tunic style dress shirt made from a light flowy material that, while walking had provided a nice breeze but under his blankets only bunched and irritated. The obvious solution was to remove them but when he’d returned to his bedroom, his earlier confidence left him. He’d looked down at the body Rachel had placed him in with concern; he wasn’t exactly bikini model hot. At least not from the outside, he had a little extra weight here and there. Glancing over to the mirror showed a slightly round face, with dark hair and wide shoulders; not unattractive by any means, but no 10/10.

His eagerness to ogle at his naked body evaporated and was replaced with trepidation. In the end, he’d opted to not change at all just deal with the discomfort, knowing full well in the morning he’d have no choice but to face the music, or more accurately mirror, when he showered.

Eventually, just as the sun began to rise, he managed to fall asleep. Only to have his phone alarm blare a scant few hours later. With a groan he got up and grit his teeth; it was time.

David decided to take the ripping the band aid off technique; tearing the clothing from his skin and chucking it all into a pile so that he stood completely naked in the bathroom. He ran his hands along the length of his body, from shoulders to hips finding the new form thick but still erotically curvy. His figure was Rubenesque, rather than hourglass but still beautiful. With a smile he looked down to note that for the most part, the weight was exactly where it should have been. A round ass and heavy breasts explained the extra weight he’d been feeling; his cleavage was truly fantastic. The dark hair, while mussed from sleep was thick and wavy, a little brushing and it would really help frame his face.

The eyes were almond shaped, with long lashes and bright blue eyes; though the effect was somewhat detracted by the dark circles his bad night of sleep left. Still, this body was by no means bad; getting a man to fall for him would be a cinch. David just hoped he could do it without having to kiss them too much.

He showered; trying to ignore the warm rivulets of water running down his curves and how lovely they felt. The moisture clung to the hair between his legs and once or twice as he stretched, he felt the water run between his folds. The feeling that elicited was…not worth dwelling on, lest he do something foolish.

Instead, he focused on getting dressed, Donna so it seemed, wasn’t the best at organisation and it took him twenty minutes of pulling clothes from hooks until he finally found the uniform. Black and white striped shirt and a short dark skirt to match. David had always loved the uniform, it was sporty while also fairly sexy on the girls. Though as he pulled the skirt up his thighs, he couldn’t help but feel somewhat uncomfortable. The skirt felt a lot shorter than it looked, or maybe that was just the sheer rotundness of his ass. It felt as though it would just take a small lean in the wrong direction to show off his panties to the world.

He gave the mirror a quick glance; the woman who looked back at him was pretty. It would be enough, no doubts. At least, that’s what he told himself.

~

Clocking in felt surreal; everybody here seemed to know him and as he picked up a tray and notepad and faced the steadily filling restaurant floor David realised.

He had no idea what he was doing.

He’d never been a waiter before; he didn’t know the computer system or even half the menu here! Across the room, Rachel entered, in a matching uniform to his own yet, somehow, it looked better. He watched as her eyes found him, looking him up and down once and then smirking. His temper flared; he’d show her, how hard could it be?

David scanned the crowd, seeing a group of guys all gathered together for an early lunch, easy pickings. Putting on his best, perky smile he walked over, letting his hips sway just a little bit more.

“Hello darlings.” He greeted, “I’m Donna, I’ll be your server, what can I get you.”

Three mumbled orders, barely any eye contact, not a single indication or arousal or even a second glance before they went back to chatting. He kept up the tight smile and walked to the kitchen, placing down the order while telling himself not to panic. It was just the first table, maybe they were were gay or something. No matter, the next one would be different.

Except it wasn’t. No matter how widely he smiled, how long he lingered or laughed; none of the men looked remotely interested. One had even complained when he’d laid a hand on his shoulder.

“Desperate, huh?” One whispered as he walked away, “I’m better she works the graveyard shift, judging by those eyes.”

“Graveyard shift the whore house maybe.” Another snickered, “She’s throwing herself at every guy in the place.”

“Hopefully she’s better that that than she is waitressing.”

Humiliation burned across his features and her fingers shook, sending the tray of drinks tumbling to the ground. Ignoring the yell of ‘taxi!’ he bent down and started moping furiously, glad his long hair hid his face away. It was those damn trays! His fingers were just too dainty to spread across them properly, how was he supposed to balance four drinks at once? A dustpan and broom appeared in his peripheral vision and when he took them, he found Rachel smiling down at him.

“Here, Donna. Let me help.” She bent down and began mopping up the spilled drink in a way that didn’t just spread the mess around as he’d been doing.

“So super easy, isn’t it?” She teased a second later.

“I’m at a disadvantage, I’ve only been a woman for a day I just need to learn to use my wiles.”

Rachel snorted.

“Your wiles? Absolutely brilliant, tell you what, if you do manage to master them, I’ll sweeten the pot this a thousand dollars.” She stood, confidently helping him to his feet. It would have made David’s blood boil he after a morning of constant humiliations he didn’t have the energy.

“You know, maybe if you actually put some effort into your appearance things might go better, those granny panties aren’t turning anybody on.”

It was only then the sound of wolf whistles registered and he shot to his feet, pulling down his skirt where it had bunched up. He knew the damn thing was too short.

~

By the time his shift ended David found his confidence totally depleted. He flopped onto the couch in defeat, trying very hard not to think about how much extra cushioning he had compared to normal. He fished the TV dinner and beer he’d picked up on his way home and set about making himself a pick me up. Maybe an hour of soccer and a good drink would be the thing he needed to get motivated and start formulating a plan.

He picked up the remote, fully intending to turn the TV on to channel six where he knew a game was playing but for some reason, he was hit with a sudden burst of curiosity to see what was on channel five. Cheery pop music poured out the speakers as ‘If You Are The One’ started up; a vapid, stupidly girly tv show he hated. Normally at least, the contestant this time caught his eye; she was young and pretty, with bright eyes and talked so passionately about her gardening hobby and how badly she wanted a man to share it. He’d always assumed these shows were fake but something about the way the woman on screen talked, it spoke to him. She just wanted to find love and struck out so many times; just like him.

He found himself enthralled with the show, even excited to see it was a double feature. He was so enraptured it took a sip of some horribly bitter drink to break his focus. His nose scrunched up and he glanced down at the can; it was his favourite brand and it tasted the same as always yet…bad. He couldn’t put his finger on it, the flavour hadn’t changed, perhaps his tongue had? It wasn’t out of the question considering all the other changes Rachel had made.

Oh well, he was sure there was something better to drink around here somewhere. He placed down the can and found it forgotten in an instant as the next stage of the game show started up.

~

The next morning he woke late; he was on dinner shift tonight, that meant he had the entire day to come up with a new plan of attack. The first thing he did was get out of bed and stand in front of the mirror, investigating his body from all angles. He hated to admit it but Rachel had a point, the large, somewhat baggy panties he’d worn yesterday weren’t going to entice anybody when his skirts slipped. The obvious answer was to get a longer skirt but, if he wanted to attract a man a short skirt was the way to do it; he that well enough from personal experience. He was musing on this when a thought occurred, strangely enough in Rachel voice:

‘Guys love G-strings…’

They do. Him included, if he had another incident like today where his skirt rose up nobody would complain about seeing this fantastic ass on display. The thought made butterflies dance in his stomach and soon he was rifling through the drawers and pulling out exactly what he sought; a pretty purple G-string with a lacy front. He slipped it on immediately, kicking the ugly white panties to the side and savouring the scratch of lace against the inside of his thighs. He looked down at himself and smiled, balancing on his toes and twisting back and forth; already this had made a huge improvement. He could see his beautiful, peach shaped ass in the mirror, thin strip of purple fabric down his cleft perfectly framing his cheeks. And the lacy front cupped his pussy perfectly, the dark hair pressing up against the design enticingly.

How good would it look, to have that fabric peeled away, it was loose enough that a finger, maybe two could fit without even removing it. What would it be like to look down and see another hand slip inside, finger stroking down his folds. Without even realising it, David’s hand began creeping toward his crotch, only stopping when he felt the digits brush the lacy surface, snapping him out of his trance. Now was not the time to be getting turned on!

Refocusing he turned back to the drawers, intending to find a nice bra and then get dressed. The first he tried on, black and simple, looked nice enough but something didn’t quite feel right. He picked up another, then another; before he knew it David had been modelling in front of the mirror for over and hour, purely for his own pleasure. He’d never realised how fun it was to play dress up! Once he had a matching bra picked out, he went through several outfits before it even occurred to him that he would be wearing his uniform tonight. An embarrassed blush crept across his cheeks at the realisation; even then he couldn’t help noticing just how pretty that made his face look in the mirror.

His face!

Those tired circles hadn’t quite gone away yet. He was going to have to figure out at least some basic make up skills if he was going to attract a boyfriend. A quick look through Donna’s bathroom drawers provided a plethora of options and just as much confusion. What the hell was lip liner and how was it different to lipstick? And was concealer and bronzer the same thing, they looked similar. For a moment an image filled his mind, of himself walking into work with a face full of clown make up. No, he had to get this right; he was not about to let Rachel humiliate him again.

David fished out his phone and typed ‘make up tutorial’ into youtube only to be floored by the sheer number. How many ways could there possibly be to do make up? Clicking on one at random he started watching with an analytical mind, trying to copy each instruction carefully but then, once again, distraction hit. He found himself really liking the host, she was so funny and her make up was incredible. In one video she collaborated with a different make up youtuber, one who specialised in making her own lipstick! How fun! Soon he had tried several looks, having fun smearing the various creams and powders across his skin. He was just finishing up a cat eye look when his alarm went off, his shift started in fifteen minutes! Had he really spent the entire day trying on make up and clothes? A small twinge of humiliation returned, though not as strong as before. It wasn’t like he was hurting anybody doing all this and it was really fun. He clicked save on the playlist; he'd finish it tonight after his shift.

~

Now it was his turn to walk in and see Rachel’s shocked face. David smirked, he looked like a million dollars and he knew it, everybody in here knew it. He basked in the attention, the way men’s eyes lingered on his ass as he walked or slipped to his cleavage when he leaned over. As he shift started, he was sure he’d have no trouble getting asked out now and yet, nothing was happening. Oh, he was getting a lot of appreciative glances for sure but by the end of his shift David realised he’d made a mistake.

Rachel had told him he needed to find a boyfriend, not a one-night stand. All of the hungry eyes watching him felt good, wonderful even but none of them were asking him out for a drink or date. And when one man he’d been flirting with cornered him on the way to the bathrooms, placing a hand across his ass and squeezing; David truly realised what sort of message he’d been putting out there. And what’s more…

A part of him liked it.

A small moan had escaped as that man touched his rear, it had felt so lovely, even through his skirt. So when he’d winked at her and whispered to meet out behind the restaurant when his shift finished it wasn’t disgust that coiled within him but desire. The man was young, cocky, clearly not looking for a relationship. It would be a waste of time and a blow to his personal pride to take him up on the offer. Even a day ago he would have recoiled but now, he was spending the rest of his shift in a day dream. The warmth of his hand still imprinted on David’s skin.

After clocking out David found himself moving, almost in a trance towards the back of the restaurant. There was wetness soaking into his thong, with each step his thighs squeezed around his pussy slightly, sending a thrill through him. The man was waiting, as promised.

‘I’m just getting rid of nervous energy’ David promised himself as he walked up to him, ‘I just need to blow off some steam.’

Without a word the man’s lips were on David’s and he was yielding with a moan escaped as teeth scraped against his plump lips. In seconds he’d wrapped a leg around the man’s waist, pulling them together so that the bulge pushed up against his pussy. He felt as though he were on fire; a deep need was growing, burning inside him and it needed to be sated. With trembling hands he was unbuckling the mans belt while he in turn slipped off his skirt. A hand brushed against his bare ass, tracing down the stripe of fabric between his cheeks.

“Fuck, Donna…” The man groaned and a new thrill went through him, David’s mouth acted before what remained of his brains.

“Say my name.” He ordered, pulling the man’s cock free and pumping it.

“Donna, oh fuck, Donna that’s so good.”

He didn’t know why, but hearing that name said in such a wonton way turned him on even more. He couldn’t wait any longer, he needed release. He pushed down the man’s pants, shivering as he peeled the G-string away from his damp hair. Moments later the item was discarded, laying on the alley floor as the man pressed David into the wall, he raised his hips, letting the man’s weight hold him up against the brick work as he thrust up into his hole.

The stretch of his inner walls was delicious, he threw his head back and moaned, unable to process anything but the intense pleasure that movement caused. Once he was buried deep inside, the man didn’t hold back. He started to thrust, hard and fast and David felt his eyes roll back. It was too good, too much, he could feel every muscle in his body tensing already. Despite that he’d told himself, he tried to hold back, he didn’t want it to be over so soon, he needed more…

And then the man said his name one more time. It echoed in his very soul, that name that was so sexy, so right; it pushed him over the edge and he was cumming. Squeezing that cock as his pussy pulsed rhythmically. It was so much better than cumming as a man, it just seemed to keep going. A few moments later his partner shuddered and a wet splash touched his deepest parts, sending an entirely different kind of gratification through him. He felt glorious. The man pulled out, thanking him for a good time and turned to leave, zipping his fly and barely paying him another look. David looked around and gathered his things; he’d acted like a streetwalker, he should feel ashamed. Yet all he could feel was his pussy pulsing with residual pleasure.