A Sugar Baby’s Transformation

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Bailey was in trouble.

She’d recently graduated collage, but her post-school job search was turning up dry. If she wanted to stay in her apartment, she’d have to find another way to make money. Figuring it wouldn’t go anywhere but it was worth a shot, she made an account on a sugar daddy dating site.

The day after she made her account, her messages were flooded with older men. They loved her slim, toned figure, they loved the perky, bubbly persona she put on for them, they loved her sleek black hair in its choppy, wavy bob.

One man in particular, Mr. Greyson, was especially fond of her hair. Soon, he and Bailey were messaging daily. One thing led to another and he invited her out for lunch: on his dime, of course. They really hit it off, talking and flirting all afternoon. When Mr. Greyson offered Bailey an allowance in return for her services, she couldn’t resist saying yes. Sure, he was four decades older than her, but he was charming and affectionate and clearly enjoyed her company.

Bailey’s allowance was already quite generous, but a few weeks into their arrangement, Mr. Greyson made her a new offer. If she brought all her clothes, shoes and jewelry included, to his apartment and let him go through it all, he’d double what he gave her.

While Mr. Greyson was sorting Bailey’s clothes into a “keep” pile and a “get rid” pile, she lounged on his spacious couch, dressed only in a set of red lingerie he’d bought her.

“Damn, you’re gorgeous.” He grinned as he looked up from the stack of sweatpants and comfy tops he was about donate to charity. “Hold that pose, right there.” He pulled out his phone and snapped a few pictures.

“Look at yourself, Bailey.” He held the phone so she could see. “You look good, don’t you?”

“I–yes Sir, I look great.” She found herself blushing slightly.

“You could look even more amazing if you let me take charge.” She raised an eyebrow, unsure what he meant. Seeing her confusion, he went on. “I’m planning to replace your discarded clothes, so you’ll always look lovely and show that tight body off.” He leaned down to grope her chest, making her giggle. “But I’ll raise your allowance even more if you let me make some more… long-term alterations to your look.”

“What sort of alterations?” A doubled allowance sounded like a dream come true…

“Leave it all to me.” Mr. Greyson patted Bailey’s head like a dog, ruffling her short, choppy hair. “I promise you’ll come out the other end looking divine.”

Bailey tentatively agreed, submitting herself to Mr. Greyson’s plans. At first, his plans were fairly minimal and easy to comply with; she had to let him choose her outfit every day, she had a diet and exercise regimen to follow, and he made her take a daily assortment of pills. He hand-fed the pills every morning, while she sat naked in lap and played with her hair. At first, Bailey felt a little odd taking these pills without knowing what they’d do to her, and having to always wear tight, revealing clothes made her a little self-conscious. However, she soon started to like the attention she got from always having her figure on display, especially the extra attention from Mr. Greyson. He couldn’t take his hands off her, enjoying her every single night.

A month passed, and Bailey’s chest started swelling, her tits growing heavy. Her hair grew from its short, shaggy bob and fell down to her shoulders.

“The pills are taking effect.” Mr Greyson grinned, standing behind her and weighing her tits in both hands. “Just as planned…”

Now, he was inspecting Bailey’s naked body in the mirror every morning before giving her her pills. He spent an especially long time playing with her hair, combing it between his fingers. He did this every morning for an entire summer, until Bailey’s hair fell down her back in a dark, impressive cascade.

She was starting to wonder how long Mr. Greyson wanted to grow her hair. Would he take it to her ass? To her knees? Did he just want to see how long it would go before stopping?

Bailey never got the chance to find out.

One morning, Mr. Greyson was inspecting her, but instead of lovingly finger-combing her hair, he grabbed it in his fist and pulled tightly. Bailey yelped in surprise, trying to get away, but Mr. Greyson forced her to her knees.

“I’m sick of this mane covering your body, I don’t know why I let it grow so long in the first place.”

“You love my hair! You tell me that every morning!” Bailey cried out in protest.

“I’ve changed my mind; I liked it better shorter. Actually, it was never short enough.”

“But, Mr Greyson, Sir–”

“I’m cutting either your hair or your allowance. You decide.”

In that light, the choice was obvious. Still, Bailey fought back tears as Mr. Greyson cuffed her hands behind her back, shackled her ankles together, then chained her handcuffs and ankle cuffs together so she was stuck on her knees, on the floor of his luxurious bedroom, in front of the full-body mirror where she held her daily inspections.

“This is the last time you’ll have this much hair.” Mr. Greyson said ominously as he snapped a few pictures of Bailey’s bound, helpless form.

Bailey expected him to use scissors and then maybe send her to a salon, but she was completely wrong. Looking up into the mirror, she saw something that made her entire body shudder. Mr. Greyson had pulled a huge, bright red pair of electric clippers from his pocket.

He grinned as he turned them on, their harsh mechanical buzzing filling the room. Bailey bit her lip, clenching her eyes shut. The clippers whirred and roared, thrumming against her scalp.

She was used to Mr. Greyson being dominant in bed, but this was different. This was more intense. This was him taking total control of her body in a more permanent way than changing her clothes.

He was far from gentle, one hand gripping her neck and manhandling her head this way and that while the other worked the clippers in long, hungry stripes across her head. Long, silky locks of hair tumbled all around her kneeling form. The clippers crunched over the top of her head, devoured the back and sides of her lovely hair, crunched unpleasantly loud behind her ears, which Mr. Greyson had to fold down to get behind.

“Quite the pair of jug handles on you, pretty girl.” He burst out laughing, turning the clippers off. “Don’t be shy, open your eyes.”

Bailey had to obey him, but as soon as she looked in the mirror her eyes filled with tears. She was a mess; her scalp was much paler than the rest of her tanned body, covered only by the slightest, scratchy layer of dark fuzz. Mr. Greyson was right about her ears; she’d never noticed before because of her hair covering them, but they stuck out at almost ninety degrees. Now they had nowhere to hide, and they were huge compared to the rest of her face.

“Mouth open, Jughead.” Mr. Greyson pinched her cheek, standing between her and the mirror. “Damn, you look just like a fresh army recruit!”

Before Bailey had the chance to craft a retort, Mr. Greyson undid his pants and unceremoniously shoved his cock in her mouth. His hands roamed all over her head, feeling up the short buzz that had replaced her long, beautiful hair, keeping her from moving as he roughly fucked her face. She was expecting him to come down her throat, the way he usually started his day, but this time, he pulled out and aimed his load all over her head.

“Go on,” He uncuffed her hands “Take care of that mess.”

“Where– where are the towels, Sir?” Bailey was shaking.

“Not with a towel, silly, with your hands. Rub my cum into your head.”

As Bailey obeyed him, her face burning with shame and arousal, Mr. Greyson recorded a video. “I’m sending this to all my friends; can’t wait to hear what they think of your new look!” He grinned wickedly, clearly having the time of his life.

The rest of the day was spent completing Bailey’s transformation from classically beautiful sugar baby to bald sex toy, as Mr. Greyson put it. He lathered Bailey’s head in foamy, thick shaving cream, joking that now she looked like his elderly, white-haired friends, then took his sweet time scraping off all the cream (and what was left of Bailey’s hair) with a finely sharpened straight razor. Mr. Greyson did this not once, but three times, until Bailey’s head was as smooth as glass and completely bald. He made her not only feel the smoothness, but rub oil into her freshly shaved head, to make it shiny.

After he’d taken what seemed like hundreds of pictures of her transformed, bald self, he left Bailey alone in the bathroom, to spend some time in front of the mirror getting used to her new look. She turned this way and that, trying to get used to herself. As she took in the sight of her naked, oiled body, something occurred to her; not only has she lost all her hair since she became Mr Greyson’s sugar pet, she’d gotten a much bigger, heavier chest. Those pills he fed her every day had left her tits heavy, swollen, and several cup sizes larger than they’d been when she first made a profile on that sugar daddy site. She had to admit, she wasn’t mad at that part of her transformation. She quite liked being more buxom. Maybe this was a worthy trade-off for losing all her hair…

A knock on the door interrupted Bailey’s thoughts. Mr. Greyson was rock-hard, tenting through his boxer briefs, and he needed to use Bailey right then and there. Wordlessly, he bent her over the sink and took her hard from behind. He was incredible stamina for a man in his sixties, and Bailey was used to him keeping it up for a long time, but this time lasted for what really felt like an eternity. A delightful, beautifully submissive eternity, with Bailey feeling like he was going to split her in half.

Right before he was finished, Mr. Greyson pulled out and made Bailey sink to her knees on the bathroom floor. A few strokes later, he was coming in thick, white ropes, all over her swollen chest and her shiny bald head.

“Good girl.” The compliment made her smile for the first time that day. “Now clean up and put on your highest heels and tightest dress. I want to show you off.”

As Bailey was getting dressed, Mr. Greyson explained that he’d invited some friends over for cocktails, and they were very excited to see Bailey’s new look. They’d all loved the pictures and videos he’d sent them.

“Think you have it in you to take special care of them?” He quirked an eyebrow. “You know, some of my friends are very talented surgeons, if you’re good to them you might get a free add-on to your new look. What do you think of getting those pretty lips done?”


Six months later, Mr. Greyson had gotten his wish, and Bailey had fully embraced her new look. She now went bald with pride instead of humiliation, gleefully rubbing her head with oil every morning. Mr. Greyson’s surgeon friends have given Bailey a huge plastic ass, tits to match, and thick, pouty lips. Every two weeks, Bailey happily knelt at Mr. Greyson’s feet and opened her mouth, ready to suck his cock while he re-shaved her head. She settled in happily to her new life as his bald, plastic sugar bimbo, always in tight clothes and high swaying heels, and she loved the way he made her look and feel.

2 responses to “A Sugar Baby’s Transformation

  1. Good concept and a great payoff. However, shaving only every two weeks? Her hair must be getting afwully long. I’d increase the shavings to twice a day! Or maybe one of Greyson’s friends could come up with more permanent solution?

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