Sally's Sugar Daddy - 1/3 (Patreon)

Contains: Breast Expansion as Weight Gain, Stuffing, Feeding

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Sally’s Sugar Daddy

I

Sally stood in the hallway of her apartment building, digging through her purse for her keys. Feeling the cold metal on her fingertips, the gorgeous Asian woman pulled the keys from her bag, slid one into the lock, and swung the door open. Stepping into her dark, empty apartment, Sally fumbled for the wall switch and flipped it on. Kicking her low black heels into a corner with the others piled there, Sally pulled the door shut behind her.

Another crappy first date.

It was the third such date this month alone. In her mind, Sally replayed all her ‘red flags’ from the evening.

“Charles” wore small hoop earrings in each ear, and his salt–and–pepper hair was more salt than pepper. Sally didn’t mind either of those things per se— she often pursued older men. They tended to be a little more old–fashioned, a little more mature, in all the best ways.

Sally stepped into her living room. The walls were bare, but the room was clean. She unfastened her skirt and let it drop to the floor.

The night started poorly when Charles suggested they meet at the restaurant instead of picking her up. Then he’d spent the whole evening talking about his crypto portfolio, never asking Sally anything about herself.

Sally unbuttoned her short navy blazer and tossed it over a nearby chair.

When she’d handed Charles her phone and asked him to take a picture of her, he’d grimaced, mumbling about working her older smartphone.

“Make sure to get all our food in the frame,“ she’d said. The man actually rolled his eyes.

Sally ducked into her bedroom to grab a pair of baggy sleep pants and an oversized T-shirt.

Sally tried to enjoy the food during their meal while Charles yammered about random tech celebrities and their ‘endorsements.’ When she asked if they could get more wine, he’d quirked one eyebrow at her like an uptight, WASPy mother–in–law.

Sally undid the buttons on her low–necked blouse in dusty rose. She knew full well that her healthy breasts were two of her best features and often showed them off in photos or on first dates.

Slipping on her sleep pants, Sally tossed the blouse on the chair with her blazer. She popped the loose tee shirt over her head, pulling out her glossy black hair to let it hang halfway down her back.

The coup de grâce had come at the end when Charles suggested they split the check. Not only was the man so fucking judgmental that he’d made disapproving noises and ‘looks’ at her while she ate — instead of appreciating her cleavage — he didn’t even have the decency to offer to pick up the check!

Undoing the hooks on her 34G bra, Sally slipped the large undergarment from under her sleep shirt and tossed it onto the chair with the rest of her date outfit. She draped herself across the couch with an exasperated sigh and flipped on the TV. She considered ordering a late–night snack to ease her lousy mood; but remembered with annoyance that covering her share of dinner had tapped out her budget for the week.

Suffice it to say Sally did not consider herself a feminist. Sure, she appreciated the opportunities in life that her mother or grandmother never got, but did those things have to come at the expense of chivalry? All Sally wanted with a nice man with a good job who would treat her right… Maybe even spoil her a little. Was that too much to ask?

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The next day, Sally sat in the office break room eating lunch. She held a giant sandwich in one hand and her phone in the other. Feeling her suit skirt pinch into her soft tummy, Sally wished for about the hundredth time that they’d been allowed to keep working from home after the restrictions were lifted. She’d gotten as much work done from her apartment as the office, if not more! As many reports were filed, as many appointments were kept, not to mention sitting through every single asinine meeting the managers and executives needed to justify their salaries.

Sally swiped left on one man after another as she tried to enjoy her lunch. One wore a beer hoodie in his main profile pic: swipe left. Sunglasses and a baseball cap in every photo: swipe left. Some kind of linen tunic and a Gandhi quote on his profile: hard swipe left.

Are there no men left in this city?

Finally, Sally saw a profile that met with her approval. “Percy” was 43, and he was a small business owner. That could have been a red flag, but Sally could tell his suits were high–end— one or two even looked tailored. Sally took a huge bite of her ham and swiss and swiped right.

Sally’s phone pinged before she finished eating. She grinned like the Cheshire Cat. Her dating profile featured only her best photos; sundresses, bikinis, and just one of her signature “smiling while surrounded by plates of food” shots. The unifying theme, of course, was her chest— every photo showed off some cleavage, and she was spilling out of the bikinis.

While Sally often struck out on first dates, she rarely had trouble securing the next first date.

[Hello Sally, you seem like someone I’d like to know. Can I buy you dinner this Friday?]

Sally’s pupils dilated, and she couldn’t stop the grin from widening across her soft cheeks. Percy was off to a pretty good start.

<What did you have in mind?>

[Do you know Antonio’s on West Fourth?]

<I’ve never been, but it’s on my list of places to try.>

[Excellent. Shall I pick you up? Or if you’d prefer not to give your address, we can meet at the restaurant.]

Sally sent the address of her building, adding <Just so you know, I carry pepper spray and have many brothers…>

[Haha! I promise I’ll be a perfect gentleman. Pick you up at 7 pm?]

<Sounds great!>

[I’m looking forward to it. Enjoy the rest of your day, Sally.]

<Thanks! You too!>

Sally tried to temper her excitement through the rest of the workday but couldn’t help wiggling in her office chair every now and then. Antonio’s was an Italian place that got almost all four and five–star reviews. It was very high on Sally’s list; but much too pricy for her to justify visiting alone. She could already taste the garlic bread and marinara.

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II

Sally checked her watch for the dozenth time, checking herself in the full–length mirror a third time. A few strands of hair framed her face, while the rest was pinned back to show off the white gold earrings dangling from each lobe. Her dress was black with spaghetti straps, and the layered skirt reached almost to her knees. She’d left the low heels in her closet in favor of a pair of black pumps that added two inches to her height, getting her almost to 5’3.

Sally ran both hands along her sides, flattening imaginary wrinkles in the little black dress. It was one of her more modest dresses despite being sleeveless. The puffy skirt made it hard to tell how big her hips and bum were, though her ample bosom usually distracted from those. The neckline of Sally’s dress was high enough that she only showed off three to four inches of cleavage, but the straps of her black bra peeked out under those of the dress. The way the fabric clung and stretched over her torso made it obvious she was packing a formidable pair of chest canons.

Sally touched one hand to her stomach and rotated in the mirror, making sure the relative smallness of her waist was apparent. She felt a twinge of hunger and furrowed her dark, thick eyebrows. She’d intentionally eaten a light lunch in anticipation of this meal date.

Seeing a message from Percy light up her phone, Sally slipped it into her small black purse and headed down. Outside her building, she found the man himself, wearing a very well–cut charcoal suit. He stood nearly six feet tall, and though his hair was starting to thin, he was more than a little handsome, with bright blue eyes and a close–trimmed beard. He stood outside a large black town car, holding the door open for her as she approached.

“Very nice to meet you, Sally.” He flashed a smile of perfectly straight white teeth and held out a hand to her.

When Sally took his hand, he brought it to his face and brushed her fingers with his lips. He helped her into the car, climbing in behind her. Percy had a driver, or at least had hired one for the evening. This was going well.

During the short drive to the restaurant, Percy and Sally made small talk. He asked all about her job, her life, and her hobbies. He offered little info about himself; but showed great interest in Sally. She told him all about her tedious job, then gushed about her hobbies, which mostly centered around social media and food.

“So you write reviews, like a food blog?” He asked.

“I started a blog, but it’s pretty light so far. I mostly just put little blurbs in some of my social posts.”

“Well, everyone has to start somewhere. It’s cool that you have something you’re passionate about.”

“Ha ha, yeah… I guess I’d call myself a foodie, but really I just live to eat…” Sally tittered, sending her breasts jiggling in her tight dress.

She caught Percy’s eyes dart to her cleavage for a millisecond, then dart back up to meet her own. She smiled up at him warmly.

“Well Antonio’s is one of my favorites, so I hope you brought your appetite.”

“Don’t tempt me with a good time.” Sally teased.

This was going very well…

Sally’s mouth watered as the mélange of aromas hit her nose. The darkened restaurant was lit primarily by candles on each table. Percy had made reservations, so they were seated right away. The rolls were still steaming when a busser set the basket on their table.

“Do you prefer red or white, Sally?” Percy asked when the server arrived with the wine list.

“Either is fine,” Sally said, spreading whipped butter on a warm roll.

Percy hadn’t looked at the list but said, “A bottle of the 2019 Palm Rocca please.”

“Excellent choice signore.”

Sally bit into the perfectly baked roll and complimented herself on also making an excellent choice.

Percy kept up his amiable conversation, seeming entirely unaffected by Sally’s visible enjoyment of the simple dinner rolls. The server returned with a bottle of Italian red, pulling the cork and pouring a sample for Percy. He sniffed, sipped, nodded, and the young man poured for them both.

The server left them to enjoy the wine for a while— Antonio’s did not rush their guests. Sally took a sip of her wine. She was no expert, but this was easily the best she’d ever tasted. She savored the long–lasting flavor of the bread and felt the heat of the wine warm her insides while she perused the menu.

“You must come here a lot… any recommendations?”

“I’ve never been disappointed at Antonio’s; choose whatever you like.”

“Hmm…” Sally’s mind reeled with possibility.

When the server returned, Percy — again having not looked at the menu — ordered a Caesar salad and lobster linguine. Emboldened by his extravagant choice, Sally said, “Could I have the Half & Half with crab ravioli?”

“Of course signora, and—“

“And the arancini?”

“Of course.”

“And the bruschetta.”

“Excellent choice.”

“Oh, I should get a salad too… the waldorf chicken salad, please.”

“Very good, signora.”

The server took their menus, leaving them alone again. Sally’s cheeks brightened.

“Sorry…”

“That’s quite alright, Sally. After all, you need to try different things to review for your blog, right?”

“Right!” Sally smiled at Percy and took another sip of her wine. She could hardly believe he’d made the excuse for her, though she wondered if he’d be quite so understanding when she devoured every last bite.

Sally stopped herself at three rolls but was very close to grabbing a fourth when the salads and appetizers arrived. The waldorf was loaded with grapes, apples, and candied walnuts— it could easily have been a meal in itself. The greens and fruits in her massive salad were all fresh, full–flavored, and bright; Sally struggled to think of a time she’d had a better salad. Percy politely declined the bruschetta and arancini, so Sally snacked on both while working her way through the massive salad and another glass of wine. Each bite was better than the last, and Sally found it difficult to keep up her side of the conversation while all the fantastic flavors danced across her taste buds.

Her entrée was almost large enough to share. The ravioli were plump and shiny, each delectable square packed to bursting with cheese and lobster meat. The spaghetti was perfect al dente, piled high with thick sauce and gorgeous meatballs. There was a brief moment where Sally thought she might be reaching her limit, but everything tasted so good that with the help of another glass of wine —and a fourth dinner roll— she was soon sopping up the last drops of luscious red sauce.

Between each starter, Percy took photos of Sally with her plates. The sheer ecstasy of her meal was apparent in Sally’s bright eyes and gleaming smile— when she looked at the photos later, they instantly went into her favorites folder. When the entrees arrived, Sally didn’t even have to ask; Percy simply smiled and held out a hand for her phone.

“How was everything, signore, signora?”

Percy answered for them both, “Excellent, thank you.”

“Would you like to see a dessert menu?”

Percy glanced at Sally. She was more than full, but he seemed to read her mind.

“No need. Gelato, please, strawberry, and the cannoli.”

“Very good signore.”

“You saved room for dessert, didn’t you, Sally?”

“Al–hic–ways.”

Just like everything else Sally had eaten, the desserts were flawless. Percy offered to share, taking only a tiny taste of each before letting Sally enjoy both. Between the flavors on her tongue and the tightness in her stomach, it was all Sally could do not to whimper at the unparalleled dining experience.

Percy was true to his word. After walking Sally to the door of her building, he leaned in to kiss her on the cheek, then squeezed her hand tenderly before releasing it.

“I had a great time tonight Sally. I hope I’ll see you again soon.”

Feeling the heavy load in her belly squeeze tightly into her dress, Sally resisted the urge to jump the man’s bones right there on the stoop.

“I’d like that, Percy. Have a good night.”

He favored her with another brilliant smile. “Goodnight, Sally.”

Two minutes later, Sally was spread out on her couch. She slid the elastic band of her sleep pants under the swell of her packed tummy, running one hand slowly over its surface beneath her oversized shirt. She could still taste the incredible flavors that had passed her lips.

“I don’t even care what the catch is. I’m sticking to this guy as long as I can, and I’m gonna –urp– fuckin enjoy every bite…”

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