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Becoming Debbie [Jock to Hot Babysitter TG]
🕑 Added 2025-09-13 00:42:52 +0000 UTCFor Anonymous
~
Tyler is a college footballer home for the holidays. Unfortunately, he gets roped into babysitting the child of a family friend who wants him to do everything just like her usual babysitter, Debbie. A task that gets strangely easier as the night goes on.
~
It was barely noon on a Saturday, and Tyler Beckett had already run five miles, downed a protein shake, and done a full circuit at the gym. He was home for summer break, but that didn't mean he could let himself go. When the new semester started up in the fall, he had to make sure he earned that football scholarship. It was his final year, and that meant looking his best for talent scouts when they came looking for the draft.
Still, it was hard work, and he was ready to spend the rest of the day exactly how he liked it: parked on the couch, Xbox controller in hand, and enjoying the lack of term papers. Which is why it was so irritating to find his mother waiting for him as he stepped up onto the front porch with that look in her eyes. The one that she always got when she was expecting him to argue with what she said.
Tyler braced himself, expecting her to demand they spend 'family' time together, or that they were going to meet up with his aunts. What he didn't expect was;
“You’re babysitting this afternoon.”
Tyler blinked. “What?”
“Valerie, my friend from yoga class, her usual sitter bailed last minute. She’s desperate. You’re going.”
“I’m not a babysitter. I’m a linebacker.”
“You’re also her only hope. She’s paying well.”
“I don’t even like kids!”
"Madison is a good girl; she's only six. I am sure you can handle it."
Tyler had never babysat before in his life; he was an only child, and when it came to earning pocket money in high school, he'd gone the paper boy route.
"If she is your friend, can't you do it?" but his mother shook her head.
"I have plans myself, with Valerie. You have arms, legs and a car. You're going. It'll be good for you, you'll get paid, and you can put it on your resume."
Tyler made a face, thinking of his future in the NFL, babysitting was the last thing he wanted to put on his resume.
~
Of course, his mother got her way; she always did. He pulled up to the address she'd given him just as the sun was going down. The house was tidy, modest, with pink chalk drawings scrawled across the driveway.
Valerie met him at the door, all frazzled hair and apologetic smiles. “Tyler! Oh my god, thank you so much for coming. I know you’re not—uh, you’re probably more used to tackling people than finger painting.”
He forced a smile.
“That’s… accurate.”
A little girl in a pair of bedazzled leggings and a paint-covered shirt peeked out from behind Valerie's legs. Valerie patted the girl on the head.
“Madison, this is Tyler. He’s going to look after you tonight.”
Madison narrowed her eyes. “You’re not Debbie.”
Give this girl an award for observation.
Tyler nodded. “Nope.”
“I like Debbie.”
“I’m sure she’s great.”
“She does the voices when she reads. Do you do the voices?”
Tyler would rather put a hole through his head, but Valerie was looking at him expectantly, and if he had to do this, he wanted as much cash as he could earn.
"...sure."
Valerie smiled, already grabbing her purse and keys. “Madison’s very used to Debbie. Debbie’s wonderful. Just do what she does. The schedule’s on the fridge. Snacks are in the cabinet, organic only! Oh, and no screen time. Debbie never allows it.”
Tyler blinked. “Right. Got it. Be Debbie.”
Valerie clapped his shoulder. “You’ll do fine. Just think like Debbie!”
Tyler wanted to argue that he'd never met Debbie, but something told him Maddison would fill him in, whether he wanted her to or not. Valerie disappeared out the door, and Tyler stood awkwardly in the entryway, facing a six-year-old who already looked like she was rating him on a scale of one to Debbie.
“So,” he said. “Wanna draw or something?”
Madison crossed her arms. “Debbie always starts with a puppet show.”
Of course she did.
Maddison showed him to a cardboard box that had been badly painted to look like a little theatre stage and handed over a basket full of soft, well-loved, puppets.
“You get in there, then start the show.
“In the box?”
Tyler blinked. Whoever Debbie was, she was clearly smaller than him.
“I don’t think I’ll fit.”
“Debbie fits, and you’re supposed to be just like her! You said so.” Maddison crossed her arms and pouted.
Tyler could already see it in his mind's eye: this little brat crying, talking about how mean he was, Valerie sending him away with no money, and only to get chewed out by his mom. Not worth it. With a sigh, he stepped behind the box and tried to squeeze inside. He curled his broad shoulders in so tight he felt them click. Then, he tried to squeeze his meaty hands into the puppers, the poor princess looked like she’d had too many cream buns.
Tyler tried to think of a good story and ended up going with a classic prince, dragon, princess rescue plot. Maddison complained almost immediately.
“That princess sounds like a man!”
“I am a man.”
“Well, change your voice, like Debbie!”
Tyler gritted his teeth; if any of his teammates saw this, he’d never live it down. He forced his voice to go higher.
“Oh my prince, please save me!” He cried, making the little puppets dance across the stage above him.
Madison laughed and clapped as the story went on, and Tyler found himself oddly getting into it. The voices came more easily, and the puppets felt less tight, even the box felt less claustrophobic by the end. Still, it was a relief to slip the puppets off his hands. Tyler cocked his head in confusion; the princess was thin again, odd. His hand almost looked…smaller.
“Debbie! It’s time for dancing!”
“Tyler.” He corrected, grunting a little as he got to his feet.
Maddison was holding out a tutu from her dress up box, and he baulked.
“Uh, no. No tutus for me, thanks.”
The little girl put her hands on her hips and pouted. Tyler sighed.
“Let me guess. Debbie always wears the tutu.”
“Yes!” She replied, “And it's ballet time.”
“What if I teach you a new kind of dancing? Ever seen break dance moves before?”
Maddison shook her head, bottom lip trembling.
“Debbie does ballet! You do it too!”
“...fine.”
Tyler slowly pulled the tutu up his legs, feeling the stiff material scratch against him. It was tight around his waist, squeezing and cinching it in. Tyler felt the air leaving his lungs and then, the squeezing seemed to stop. He looked down at himself and winced; thanks to the tutu around his middle, he almost looked like he had an hourglass figure. Maddison hit play on her little speaker, and soft piano music began to play. She planted her legs and started dancing.
“Here, copy me, I’ll teach you to dance like Debbie.”
Tyler sighed and tried to do it. Hips moving back and forth, shoulders shimmying. His body was still aching from the workouts today, and the movement was only making his body look stranger.
As the song went on, Maddison added jumps. Tyler leapt into the air and to his shock, his toes pointed all on their own, making him land softly, just like a ballerina. Maddison clapped in delight.
“That’s it!”
Tyler twirled and blushed when he felt his ass jiggle a little from the movement. Maybe he needed to up his workout, if his ass was heavy enough to move like that. When the song finally came to an end, Tyler let out a sigh of relief and gripped the tutu, eager to get it off. Only, it wouldn’t come off. No matter how much he wiggled and tugged, the tutu just couldn’t get past his hips all of a sudden. It was as if they’d stretched out while he was dancing somehow.
“It’s okay, you can keep it on.” Maddison smiled sweetly. “It suits you. Now, snacks please!”
Tyler felt a smile form on his face, and he leaned down so they were eye level.
“Do you want your favourite organic veggie chips?”
“Yeah!”
Maddison ran for the kitchen, and Tyler’s mouth opened and closed in shock; what had been that sickly sweet voice? And how had he known her favourite snack? He followed her to the kitchen in a daze, seeing the note laid out detailing exactly what Debbie did when she babysat. There it was, plain as day, Maddison’s favourite snacks.
“I guess I must have glimpsed it from the lounge.” He muttered, reaching up to the top shelf for the snack, only to wince.
His chest had hit the lower shelf, and it hurt way more than it should have. He grabbed the chips and poured them into a bowl. As he leaned over, he noticed something else, weight, where there hadn't been before. Tyler placed the bowl down in front of the excited six-year-old and rubbed at his sore, heavy chest, only to freeze.
The skin under his shirt felt different; soft. He looked down to see the fabric of his shirt being pulled taut as two mounds slowly pressed outwards. A yelp of shock escaped him, and Maddison looked up innocently.
“What’s wrong?”
“Nothing! Uh, I am going to the bathroom, don’t choke!”
Tyler ran, now intimately aware of how his ass was bouncing with the movement, and how his chest was growing so much it threatened to do the same. He stumbled his way into he bathroom and shut the door, leaning heavily on the sink and gasping for breath. With each inhale, he felt his shirt getting tighter. All it would take was a single glance up to the mirror, but he was terrified to look and see. Instead, he stared at his hands gripping the sink.
His soft, delicate, feminine hands, nails perfect little ovals with French tips. They gripped the sink so tightly his knuckles went white. What was going on? His breathing got ragged as his shirt got tighter. There was no other option; he had to take it off.
Tyler struggled out of the stretched shirt and felt his new breasts fall back against his chest. The hard pecs he’d worked for were gone, replaced with supple curves and dark pink nipples.
“What the fuck?” He breathed, poking the side of his new breast, half expecting it to disappear.
The skin was still tingling and stretching; it sent a shiver down his spine.
“Debbie! What’s taking so long?” Maddison called from the other side of the door.
“Tyler, Maddison, my name is Tyler. I uh, spilled water on myself. Do you think you could bring me a new shirt?”
“Okay!”
He listened to the sound of skipping footsteps disappearing down the hall and bit his lip hard enough that it started to swell. What was going on? His body was changing right in front of him. What would be next? A tiny knock at the door made him flinch, and Tyler grabbed for the towel on a nearby rack to cover himself as it opened. Maddison’s hands appeared, dropping a bundle of clothes on the floor before closing the door again without entering.
“Here you go!”
Tyler paled: a pale pink shirt with a sweet heart neckline and capped sleeves, and a pair of skinny jeans, clearly cut for somebody with a curvaceous figure. There was even a bra hidden between them.
“Debbie left them last time! You can have them!”
Tyler wanted to argue. He couldn’t wear these! Then again, what else could he wear? There was no way his shirt would go back on, and even if it did, it probably wouldn’t look very appropriate. He swallowed and slowly stripped down to dress in his new outfit. The jeans hugged his legs perfectly and sat low on his now wide hips. The bra was a struggle; he could only get the hooks done up with the help of the mirror, but when they finally clicked, he sighed in relief. The weight on his chest was much easier to bear with it; the only trade-off being that the bra had some sort of pads in the cups, making his cleavage practically fall out.
He hated how comfortable the clothing felt, almost like a second skin. Tyler didn't want to like it, but he did, even if he felt a bit ridiculous as he looked in the mirror. His body was that of a beautiful woman, save for the shape in the front of his tight jeans. But his face and hair were still his own. What would Maddison say when he came out? Would she laugh? Or worse, call somebody?
“Come ooooooon!” Maddison cried, “It’s time for makeovers!”
“Kill me,” Tyler whispered to himself before opening the door.
He expected a scream, not a squeal of delight.
“Yay! You look just like Debbie! Come on, I will do your make-up just like hers, then you can do mine!”
The little girl grabbed his hand and dragged Tyler down to her bedroom; it was a pink frilly nightmare. Tyler was beginning to suspect he had offended some demon and they’d crafted this place especially to torture him. Reluctantly, he sat himself down on the floor, feeling his now plush ass cushion and sink into the thick carpet. Maddison collected a box from her dresser and set it down, lifting the lid with a little ‘tada!’. Inside was a messy collection of lipsticks, compacts, brightly coloured pencils and tubes. Tyler bit his lip again; he had to stop doing that, it was starting to feel swollen.
“No, I am putting my foot down.” He shook his head, “I can't let you do my make-up.”
“But Debbie always does!” Maddison pouted, “You promised to be just like her.”
“No, I didn’t! Look, why don't we watch TV?”
“Mommy said no screen time.”
Tyler groaned. “Come on, no screen, kids love having a babysitter who lets them get away with stuff. Don't you want to watch some cartoons or something?”
“No!” Maddison crossed her arms and pouted even harder. “I want you to be just like Debbie! So you are going to let me do your make-up, or else!”
Her bottom lip wobbled, and Tyler caved.
“Alright, just don’t cry, okay?”
“Hurray!”
Maddison’s hands dove into the box and produced a thick stick of dark pink lipstick. The little girl held his chin with one hand and the lipstick in another, then carefully painted the pigment onto his plumped lips. It felt odd, not as odd as the blush she dusted over his cheeks, though. He swore he could feel them moving, and his jawline softening as she painted his skin. Tyler realised, to his horror, that he could; she stuck little stickers on his earlobes and a second later, there was a prick of pain as they became real studs.
Maddison was painting his face, and it was changing. She didn't seem to notice, though; she just went about humming to herself as she transformed him. Tyler sat, frozen in fear as she reached for a hairbrush.
“Time for hair styles!”
“But…my hair is short…” He stammered.
Maddison didn't care; she reached up with her soft brush and began to run it over his skull. With each stroke, his hair began to grow until she was holding great handfuls of it as she brushed.
“Your hair is so lovely, Debbie, so soft.”
“Ty-Thank you.”
His eyes went wide; he’d tried to correct her, but couldn’t bring himself to do it, just like he couldn't bring himself to stop humming a little tune under his breath.
“Yay! Will you sing me a song?’
Tyler wanted to say he didn't know any songs, well, not any songs that would be appropriate for a babysitter to sing to a six-year-old. But then he saw Maddison’s face and felt compelled to make her happy.
“Twinkle twinkle, little star~”
His voice was soft and musical. Tyler hadn’t sung a note since grade school choir, and yet, here he was with the voice of an angel. A female angel, too. As he sang, he felt his Adam’s apple melt away, and Maddison smiled and clapped. Her joy made happiness spark in his own chest. A strange sort of fulfilment he’d never experience before. He felt the strangest urge to do whatever it was that made Maddison happy, which meant being just like Debbie. A smile spread across his lips, and he gave the girl a quick hug.
“I look so pretty, you’re such a clever girl, Maddison.” He cooed, “But it’s getting late. Go brush your teeth and get ready for bed.”
“Awwww, but you haven’t done my make-up yet!”
“Oh, of course.”
Tyler had never done make-up before, but he had to learn fast; Maddison would be sad if he did it wrong. He had to do it just like Debbie would. Luckily, his charge told him exactly what to do. Soon, they were a pair, with the same pink lips, though Maddison’s look was a lot more childish.
“There you go, sweet girl. Now, go brush your teeth.”
Maddison grinned and skipped off down the hall, leaving Tyler alone, and all at once, reality hit. What was going on? Why was he so compelled to act like…Debbie, he assumed. He’d never even met her, and yet it seemed like the universe was somehow conspiring to turn him into Maddison’s favourite babysitter!
He got to his feet and stumbled up to her dresser; a stranger looked back at him, a beautiful, busty brunette with soft lips and wide hips. She had a gentle, girl-next-door aura about her. Tyler knew it instantly; he’d become Debbie. But he wasn’t perfect yet.
There was a suction that formed between his legs, and he whimpered, feeling the last sign of his manhood disappearing. He was becoming Debbie, the perfect babysitter, and there was nothing he could do to stop it. The sensation ended, and Tyler was left gasping. Now fully transformed into a woman.
“I have to get out of here,” he muttered, heading for the door, only for Maddsion to step out of the bathroom with an innocent look on her face.
“Is it story time?”
‘No!’ Tyler wanted to yell, ‘It’s time for me to get out of this house!’
The words wouldn't leave his mouth, though, the compulsion was too strong. Instead, he opened his arms. The desire to see his little angel smile was too much. He wanted nothing more than to make Maddsion happy.
“Of course it is, sweetie! Let’s go pick a book!”
Maddison skipped up to him, wrapping her arms around his legs with a cherubic look on her face.
“I’m so happy you’re back, Debbie.”
“Me too,” Tyler smiled sweetly, “me too.”
