[TG] The Humbling of David - Part 2 (Commission) (Patreon)

Commissioned by Dash666 on DeviantArt

~

David had gone home an emotional wreck; full of gratification and residual pleasure but feeling so very deeply ashamed of it. He was supposed to be an alpha male, inside and out and yet he’d fallen into that other man’s arms so willingly, let him fuck him in an alleyway like a common whore and liked it. Even now, as he drowned in his own self pity he wanted to do it again; it had felt so good to be desired like that. He’d bitten his lip, letting the pain centre him; trying his best to quash such desires. He had to start taking this seriously, if he didn’t turn back soon who knows what he might do, what urges he may give in to. Picking up a serious boyfriend at the restaurant was clearly not going to work so he’d have to resort to more direct methods.

Opening his phone, he downloaded the five best rated dating apps he could find, desperate perhaps, but then again, he was. He started filling in profiles at a rapid pace, making sure to select the option for serious relationships only, even if his finger did hover over the hook up button longer than he’d care to admit. When it came to the hobbies and interests’ section he hesitated; as David he’d liked the usual, soccer, hockey, a good action film from time to time but typing it out felt…wrong.

‘I like to garden…’

That strange voice in his mind again, a thought that was his own and yet not quite. He glanced around his new living room, at the many vases of flowers and his thoughts flowed to the garden beds outside, all filled to the brim. Donna clearly did like to garden and the more he focused on it, the more appealing it became. He tucked away a mental reminder to get out there on his next day off, the petunias were looking a little dry. Before he knew it, he’d filled in the interest section with talks of flowers, gardening and romance novels. It almost seemed generic but honesty was the key to a good relationship, at least that’s what they all say, whoever ‘they’ were. Besides, what guy didn’t expect a woman on a dating app to have an interest in romance films?

The last thing all these new profiles required was a photo, a simple task for most women whose phone were already filled with vapid selfies. He’d have to pose for one, it couldn’t be too hard but he had to make sure it was good quality, a photo is worth a thousand words and nobody was going to read through his profile if they didn’t like the picture attached. Grateful for all those make up tutorials he sat down in front of the mirror, wiping his skin clean so that no trace of his smudged lipstick and eyeliner was left to remind him of his slutty behaviour. Then, he propped open his phone to a tasteful make up tutorial and began to follow along, enjoying the slick feeling of gloss across his plump lips. His face was a bit chubby, but with the help of some bronzer and something called ‘contouring’ he was soon looking beautiful. He resisted the urge to doll himself up further, pushing the smokey eyes or lash wings; he needed to look good, but not desperate.

He lifted up his phone, pointing the camera at his newly made-up face and grimaced; he looked good but a straight on shot just looked…dull. He needed to look fabulous if he was going to attract anybody. He began to walk around the house, trying different backdrops, angles and poses until finally he found the perfect shot, slightly pouted against the blankets of his bed. He grinned and took another, then another; he’d never realised just how fun it was to take pictures of himself! It wasn’t vapid or shallow, it was fun! Soon he had an entire folder full, some slightly racier with his cleavage showing prominently. Perhaps if he started chatting to a man on one of these apps, he could send it to them. The idea of a man getting hard looking at his picture, pleasuring himself to Donna’s face; fuck it made him wet just thinking about it. David had to resist the urge to slap himself to snap out of it. What the hell was wrong with his brain lately? He put down the phone hard on his dresser and went to go take a cold shower.

~

David couldn’t help but feel he was doing the walk of shame entering work the next day, his embarrassment flaring as Rachel caught his eye in the break room as she arrived. Her smile was like the cat that got the cream as his humiliation showed clearly on his face.

“Hey Donna, have a nice night?”

“It was fine.” He replied, trying not to give anything away.

“Really? Just fine, you didn’t happen to meet somebody and have a little fun, no strings attached?”

Was he that obvious? How could she know? Surely, she was just fishing, yes that was probably it. He shook his head confidently, only to have that gravitas fade as Rachel fished her phone out of her apron pocket and opened a video. David’s stomach dropped into his toes; it was security footage of the alley behind the restaurant and there he was, moaning as that man ploughed into him, a look of ecstasy etched across his features. Despite his best efforts, just looking at those images made him ache, a now familiar burn of lust starting to form between his legs.

“Did you forget about the cameras, sweetie?”

David felt as though he was going to die of humiliation, face beet red as Rachel threw an arm around his shoulder.

“Honey, you’re worth so much more than a quick fuck, you deserve a guy who will treat you right. Don’t worry, I deleted the footage so nobody else will see it. It’ll be our little secret.”

Anybody who would overhear it would think Rachel a good friend, one trying to increase Donna’s confidence. But he knew better, he could hear the slight edge in her voice, see the teasing self-righteous smile. As if to add insult to injury his phone pinged, the image of one of his new dating apps lighting up the screen with a push notification; ‘Nobody has selected you yet, try these five tips to make your profile more appealing!’.

Rachel practically squealed with delight.

“You’re using dating apps! How brave, I know some people think that’s a desperate measure but I’m glad you’re putting yourself out there.”

“You’ll see, I’ll have a boyfriend in a few days, no problem.” He swallowed, most of his fire extinguished by embarrassment.

“Well, I want to help you do that of course.” To his surprise she sounded genuine.

Rachel then turned to face him fully, a serious and sympathetic look on her face.

“Honey, tough love time. I really think you’ll struggle to find a man until you lose some of that chub.” She grabbed a handful of his ass and squeezed, “Why don’t we start going to the gym together! Doesn’t that sound fun?”

It sounded like hell but, as much as he hated to admit it, she was probably right. It was odd, despite all the nasty comments Rachel was throwing his way he felt a sense of camaraderie forming between them, as well as a strange desperation to prove himself right and win not only their bet but her approval. That would be the ultimate revenge, wouldn’t it? Not only proving himself right but having her be jealous of him at the end.

“Let’s go after work today! We’ll make a girl’s night of it, get some dinner, watch some a romcom after, sound good?”

“Yeah!” It really did and David found himself blushing even more at his enthusiasm.

‘This is a trying time for me, there is no shame in enjoying being girly just a little…’

His smile turned genuine. He was right, he should try to find joy wherever he could in this strange new life; why force himself to be miserable? He worked his shift with a soft smile on his face counting down the minutes until girls’ night could begin.

~

Putting on workout gear felt…wrong. Rachel was standing in the doorway to the changing room, arms crossed and impatient as he squeezed his huge tits into the sports bra. It and the cropped yoga pants felt so tight to his skin he felt practically naked. There was so much skin exposed and while he didn’t think he looked bad, there was no denying that next to Rachel’s toned body he looked like the stereotypical chubby friend. His lovely curves were so heavy, they stuck out so much he’d almost knocked over a pile of paper cups by the water machine with his ass turning to quickly.

“Are you sure this is what I should wear?” He demurred, “I feel a little…exposed.”

“It’ll motivate you to work hard!” Rachel insisted, grabbing his hand dragging him out onto the gym floor, “Now come on! We need to get started!”

David had never been to a gym, he had no idea what a ‘set’ even was or how to do it so he was thankful when Rachel pulled him over to the treadmills, a machine even he knew how to work. He started off with a gentle walk only for his friend to scoff and turn up the dial quick enough he almost fell.

“You wont loose any of that weight if you don’t push yourself.” She chided, “Now jog!”

He didn’t have much of a choice in the matter. At first, he even enjoyed the slight burn in his muscles as they started to stretch out and work but then he felt something all together different. This sports bra was doing nothing to support his breasts and soon they were bouncing, as was his ass. Unlike Rachel, whose butt was firm and tight, his was fat and peach shaped. Short of reaching behind himself he could do nothing to stop the jiggling display and judging by the looks he was getting from other gym goers; it wasn’t subtle either. His eyes found the mirrored wall to his left and David found himself mesmerised by his own body; each of his curves was moving, bouncing, almost hypnotically. It wasn’t an obscene display but it was hardly classy either.

A man wolf whistled as he passed, cocky grin on his face.

“Yeah, shake it babe!”

At first, he was horrified but then one of those strange intrusive thoughts slid into his brain once more.

‘I like that attention. I want more.’

He blushed, giving the man a demure smile; eyes raking over his muscled torso. He was nothing like the reedy, thin man he’d been with behind the restaurant last night. How might it feel to have his tits squeezed by such strong hands? To have those broad shoulders wrapped around him, pressing him into the bed as he thrust deep inside…

Wetness began to leak from his hole, soaking into his thin panties and then straight into his skin-tight pants. He was thankful for their dark colour; nobody would be able to tell but the glint in Rachel’s eyes told him she suspected. God, his hormones were out of control! He had to snap out of this. He may be in a woman’s body but he was a straight man under it all…right? Last night, and his horniness just a second ago they were flukes, stress manifesting in different ways. Yes, that’s what he told himself, for the alternative was far too frightening.

They continued their gym work out, each station finding a new way to show off his body. The leg press had his ass on full display, the weights his chest, even the exercise bike had his skin glistening and pink, moistening gathering in his cleavage making them shine under the harsh florescent lights. And each time a man winked at him or gave him an appreciative stare, David found himself glow with pleasure.

~

Dinner had been a healthy salad selected by Rachel, his stomach grumbled for more but then she’d laid a hand across his stomach and shook her head.

“Don’t undo all that hard work.” She’d cooed, “Now, let’s watch the movie.”

It was some silly, completely unrealistic fare which would normally bore him to tears but for whatever reason, this time he found fascinating. As Rachel’s eyelids began to droop a plan began to form, if she fell asleep, perhaps he could snoop through her things and find a cure for all this! He just had to stay awake longer. Something that was easier said that done; his body was exhausted after a day of work on his feet followed by the gym. Not only that but this film was so captivating he kept getting distracted and forgetting to check if Rachel was still awake.

By the time the couple embraced, soaking wet in the rain as the credit rolled David had sympathetic tears burning in his eyes. It had been so beautiful, if only his life could be like that, swept off his feet by some rich handsome stranger with a heart of gold. No, what was he saying, he was the stranger with a heart of gold waiting to sweep a girl off her feet, not the other way around. A buzz at his thigh; his phone. He opened it up and felt his eyes widen, a message!

‘Hey, saw your profile, I think we could be compatible, want to hang out some time?’

Not exactly a romance for the ages but David forced his disappointment down, he didn’t actually want a real romance. He just needed a guy to take him out a few times so that Rachel would turn him back. He eagerly messaged back, clicking on the man’s photo and swooning. He had dark skin and a chiselled jaw and those eyes, so intense. James Figero, such an exotic name too! He couldn’t help but squeal a little to himself as his message was returned and soon, they were chatting away amicably about nothing, all the usual first touch stones, weather, films, work. David couldn’t help but gush about the film they’d just watched, it was sure to be considered a classic in the years to come, though James seemed to think he was exaggerating. He made a mental note to invite him back to watch it after their date in a few days’ time.

His heart felt light and hope began to bubble in his chest, perhaps this was the one, he’d be back to his old self soon enough if this went well and he was actually excited for the date! Another excuse to dress up and doing his make up properly, and since it was a dinner date, he could apply it more heavily than if he were just going to work. He was so caught up in his excitement he totally forgot to check for clues in Rachel’s bag.

~

David entered the restaurant with a wide smile on his face; things were finally looking up. All he had to do was smile, laugh at James’ jokes, and bat his eyes and he’d be home free within a few days! He recognised his date immediately, already seated at a romantic little table for two in the corner. He was just as handsome as his picture; that strong jawline decorated by a handsome, short cropped beard and his suit perfectly accentuating his broad shoulders. David felt something stir in him, true attraction; not just pent up sexual desire but actual romantic and physical attraction…to a man. He’d been so caught up in this little game between he and Rachel he’d mistaken his excitement for his first date as nothing more than impending victory but now, he was sure there was something more.

He didn’t just want James as a means to an end, David wanted him to truly desire him in return. He wanted this man to look at him with more than just the lust of that fellow behind the restaurant. He bit his lip, trying to get himself under control but suddenly there were butterflies in his stomach and he was filled with a need to make a good impression.

In his excitement, he called out a little louder than he probably should have, causing several people nearby to jump, including James. He blushed, sending the other patrons an apologetic look before heading in James’ direction. With each step he felt his hope fading; James didn’t look impressed with what he saw. David watched as the mans eyes flicked up and down his form, not a hint of a smile to be seen.

Had he not dressed properly? He’d tried on almost everything in his wardrobe before settling on the small black dress; even he knew the reputation of the little, black, dress, it was supposed to be perfect for every occasion! So why wasn’t James looking at him with desire or even happiness? Before he’d even sat down David could see the regret in the man’s eyes.

“That was quite the entrance.” James mused and David giggled nervously.

“Sorry, I was just excited to see you. You’re my very first date from the app.”

Inwardly he cringed, James outwardly. What a stupid thing to admit! He needed to be confident and in control, no wait, he was the woman now he needed to be submissive and demure. Yes, that’s what he wanted in a woman, it’s what every man wanted, right?

“Can’t imagine why.” James answered politely, “Though I do have to admit, you do look a bit different from your photo.”

Did he? David looked down at himself and felt his stomach sink. It was obvious from this angle, the dress was a size too small, rather than being tight and shapely it was hugging him in all the wrong ways. Bust practically spilling out and not in a sexy way. His mind flew to the pink lipstick he’d painstakingly applied; he could see it now, reflected in his water glass. He’d selected the shade because he thought it was fun and flirty, now it just seemed garish.

No matter, he had to reel this back in. He could do it; he knew he could. David put on his best, most charming smile and leaned forwards on the table, hoping it would cast his cleavage in a better light.

“So, James. Tell me about yourself.”

Men loved to talk about themselves, he should know, he was one. No matter what Rachel, this body or even his own brain said sometimes he was a man deep down. Yet James’ replied were clipped and to the point. He spent more time looking at the menu than his date and David couldn’t help but notice when they did order, James chose the soup. The smallest and quickest to eat meal on the menu.

~

His date with James had not gone well. He had feebly attempted to set up a second only for the man to go radio silent before his profile discretely disappeared. The genuine hurt that filled his heart surprised David; rejection always hurt of course but he didn’t expect it to feel so…personal. For the first time in his life, self doubt began to creep into his consciousness; whenever his dates had gone badly before he’d blamed the woman but now that he was the woman that mentality was twisting in on itself. He couldn’t help but feel he simply hadn’t been good enough for James.

When Rachel had casually asked how the date went, he couldn’t help it. He burst into tears, sobbing like a school girl rejected by her crush. It was humiliating but Rachel had taken him aside, let him cry on her shoulder and wiped away her tears.

“Don’t worry, there is always next time.”

He’d let that buoy him for a while; being more proactive on the apps and messaging men first more often. He secured another date, this time with a body builder names Josh. It had not gone well. Nor had his one with Phil, Jack or Steven. He’d started being more forward, messaging men with some of the alluring photos he’d taken and had a litany of rejections and unanswered messages to show for it. The ones that did reply he found hard to hold onto, after two weeks of trying he was yet to secure himself a second date with any of them. He found the handsome ones easier to get along with but for some reason, they were always curt and quiet, leaving at the end of the night with no intentions of seeing him again.

And with every rejection David felt himself steadily being filled with a new desperation; a yearning to be desired and loved. It started with those photos, sending them to people on the app in a despite hope for some form of approval and when that failed, he made them more sexual. He took photos of himself wearing nothing but a towel, then nothing at all. All the while fighting the urge to take another stranger out back after work and let them fuck him, just to feel some semblance of gratification.

He doubled his efforts at the gym with Rachel’s encouragement but nothing seemed to be working. No matter how hard he tried he only seemed curvier and more heavy set; especially next to his much more attractive friend. He found himself increasingly horny as well, keeping all those urges repressed was becoming a daily struggle; each glance at his reflection filling him with a mixture of arousal and shame. He found this body so sexy, why didn’t anybody else? The women in those films they watched seemed to have it so easy. He found himself increasingly enraptured by romance; reading and watching everything he could find on the subject. Becoming enamoured with the worlds and lives of women who seemed to stumble into love and sexual escapades without ever trying. How he longed to be one of them.

He knew his self pity was turning men away. Each time he got a date he was so clingy and desperate they practically had to peel him off their arm at the end, but he just couldn’t help himself! His confidence was at rock bottom and causing a never ending cycle of clingy, over eager behaviour. It was while scrolling through romance advice forums that he found a potential solution. It was an article on dressing for your body type. He’d become increasingly interested in clothing over the last few weeks, having spent much of his pay cheque each week on new outfits, justifying them as part of his cause to be turned back. So, when he clicked on the article and was met with a picture of a voluptuous, curvy woman just like him looking like a million dollars. He was hooked and soon after was saving picture after picture of 1950’s style pin ups. Back then, curves were in, so all he had to do was cater to that audience. Less jeans and more flared dresses and skirts, with pumps and maybe even some gloves.

The next day he dove head first into shopping, checking out every vintage and second-hand clothing shop in the area for new clothes, even finding a few recreation websites online. He spent a stupid amount but it was worth it when he slid that first red polka-dot fit and flare dress on and turned to see his reflection. His cleavage was ample, his hips wide but both things were utterly gorgeous in this attire. He paired it with a smattering of bright red lipstick and spent the rest of the day feeling hot and confident, strolling the streets looking like a pin up.

He couldn’t help but flush with pleasure when he met with Rachel and Pat for lunch wearing a similar, peach pink, number. Pat’s eyes had almost fallen out of his head much to Rachel chagrin; he couldn’t be sure but judging by the sudden wince and way Pat picked his jaw off the floor, it seemed his wife had kicked him under the table. Still, she had nothing but kind words to say about his newfound look which only fed his confidence more. Was it strange, to feel pleasure knowing his former friend found this new body attractive? No, it couldn’t be. After all this body wasn’t really ‘David’, Pat was attracted to Donna, not him and there was nothing weird about letting that boost his confidence a little.

It did have one added side effect though; he was getting picky, if men were judging him by appearance alone why shouldn’t he do the same? Yes, he just needed any old boyfriend but to secure them he was probably going to have to kiss and touch the person in question and well…he didn’t want somebody unattractive. But still a hot date eluded him and with only a week and a half left before the deadline he was starting to feel the noose closing.

“Why do none of the hot guys like me?” He whinged, laying across the couch with his feet on Rachel’s lap, arm swung dramatically over his face. “I’m cute as a button, especially now that I have learned a thing or two about appearances, the guys should be falling all over me!”

“Not as easy as you though, eh?” She teased. “You can always admit defeat…”

“Never!”

That smug grin would never go away if he did that!

“Maybe you should lower your standards a little, physically.” Rachel suggested, picking up his phone and swiping through today’s list of matches. “How about this guy?”

He was thin, a little pale, with thick set glasses and a shirt so crisp it made him itchy just thinking about it. He wasn’t ugly by any means but he certainly wasn’t what David would consider ‘hot’.

“I don’t know he seems a little…nerdy.” He shrugged, “I want passion, real romance, y’know?”

It was funny, he hadn’t even realised he did want those things until he said it. Without meaning to he’d started taking this find a boyfriend thing a lot more seriously. He furrowed his brow; why didn’t he just look for some ugly, desperate guy on one of these apps and say yes when he asked him to be his girlfriend? It was the obvious answer to his problem and not against the rules Rachel had put down. So why couldn’t he bring himself to do it?

It would be immoral to play with a guy’s feelings like that yes but his entire life was at stake. Since when was he such a wuss? Maybe it was all the feminine hormones in his system now but he could not help but imagine how hurtful that would be. He’d been a guy just looking for love not long ago if a girl pretended to be interested in him for her own self gains it would have crushed him. He couldn’t do that to somebody else.

It was more than that though and he knew it. He was loath to admit it but…being Donna was growing on him. Especially his body and the wonderful sensations it was capable of feeling. He wanted more of that; he wanted another man inside him but not just that; he wanted a man to truly love him. He didn’t just want sex, he wanted to make love as Donna and that required a man whom he was actually attracted to.

“Are you okay, honey?” Rachel asked, putting an arm around him, “Do you need to talk? The men on these apps aren’t giving you a hard time, I hope? If any of them abuse you, tell me and I’ll set them straight!”

He gave her a grateful smile. Despite the strange circumstances, Rachel had actually been a good friend all things considered.

‘My best friend…’

As much as he wanted to be right and win their little bet, David had to admit he would be sad to lose this bond between them if he turned back. When he turned back. He had learned a little from this experience though, he wasn’t going to rub it in her face; well, not too much.

“No, nothing like that I’m just…tired.” He stood up, “Sorry, I am going to head to bed, I’ll see you at work tomorrow.”

Rachel made a face, clearly not believing him but getting to her feet anyway and gathering her things. With a wave goodnight, David closed the door and leaned against it with a sigh. He didn’t know how to feel; was he gay now? Had he always been and covered it up? No that couldn’t be right, he’d never had these urges before, it was this female body that was messing with his mind!

‘Look at that profile again…’

Almost in a trance he opened up his phone, the strong desire to see that man’s face again washing over him like a wave. To his surprise though, this time upon viewing it David felt desire coil in his gut. The man was nerdy, the world bespeckled came to mind, but there was an earnestness there. A sort of gentle kindness in his eyes which he found attractive all of a sudden. All those muscle bros suddenly seemed so shallow to him; all brawn and macho bravado. This man, Sean his name was, he was the sort of man to really treasure a woman. He could imagine him really taking his time in the bedroom, giving his partner all the attention she desired during their lovemaking. He’d treat Donna, treat him, right.

Biting down on his lip, David swiped the profile up and hit the message button.