Chapter 40
by
Helforster
Next
Shopping Spree!
The next morning, Aaron was woken up again. This time, Sarah stood over her father and tossed a bra and a pair of panties over to him right off the bat. Aaron slowly got up and tossed the underwear aside and caught a quick shower, using the girly products again, getting out, and almost on autopilot, he put some pink lipstick and mascara on. When he got back out, Sarah was laughing.
“Did you put makeup on all by yourself?” She asked, mockingly.
“I..I don’t know why..” Aaron stammered. Maybe all this girly stuff was getting to him.
“Awwwww.... my mom is becoming a big girl!” Sarah joked, but gave her dad a hug as he slipped the bra and panties on.
Aaron’s cheeks were red, and Sarah helped him get his clothes on. He was still pretty groggy, so he kind of jut let Sarah put whatever she had onto him. Sarah took full advantage of this, dressing him in a pair of denim booty shorts and a white crop top. The tight lacing on the corset had really smashed Aaron’s waist inward, so his figure looked good, even as his midriff was visible.
He was almost asleep for the whole drive over to the mall, and when he got out, he felt a cool breeze wash over him. That was enough to make him look down and see the revealing outfit his daughter had put him in.
“OH MY GOD, what did you do?!” Aaron’s yell turned quiet as they walked into the mall.
“You look good, mom.” Sarah put her arm around her father’s shoulder and squeezed, whisking him into the building.
They made a B-line to the Franny’s, a discount department store that took up several floors of the mall. Sarah was on a mission and sent the pair all the way to the formalwear section. The racks were covered in pantsuits, blouses, skirts, and everything a working girl would need to succeed. Sarah grabbed outfit after outfit off of the rack and started piling them on Aaron’s outstretched arms.
Sarah smiled before pushing her father into the dressing room.
The first outfit that Aaron saw on the stack was a simple one. It was a modest, pleated black pencil skirt. He slid it up his waist and held it as he grabbed a light pink blouse, which he buttoned up and tucked into the skirt. The skirt itself rode high, settling in the middle of his waist and giving a really nice tapered in figure appearance, and the blouse was cut low, a little too low for Aaron’s comfort.
He looked at himself in the mirror and he could barely recognize himself. He looked like a woman, and a woman that a younger version of himself might’ve been attracted to. Hell, he was attracted to the woman standing before him. With that thought, he moved out of the changing room to meet Sarah, who was standing outside. When she saw him, she immediately started clapping.
“You go, mom!” She cheered.
This continued for some time, with Aaron trying on more and more different styles of skirt, saying no to some, a begrudging yes to others. The stack was getting pretty big and the girls went to check out, carrying a ton of big bags over their shoulders as they moved on.
Next was the shoe store, and the same basic routine occurred. Aaron’s foot was feeling much better, which wasn’t good because that meant it was heel time.
“Don’t worry, they’re cute” Sarah said as she watched her father stumble around in a pair of 5-inch platform boots.
“Please, no” He responded, trying to keep concentration.
Sarah nodded, handing her father a pair of much smaller heels. A pair of patten leather pumps, the kind of classic looks you’d expect from a secretary or a particularly attractive teacher. Aaron internally cursed his small shoe size and slipped them on, walking out only to realize that he had kind of gotten the hang of it. The shape of the shoes **** him to swing his hips side to side as he walked, but as he did, he never felt off balance. Sarah was almost as shocked as he was to see her father absolutely rocking that pair of heels, and she cheered him on before getting a few different, similar pairs of shoes to the checkout.
With even more bags in hand, Sarah smirked at her father, “What’s that look?” Aaron remarked.
“Let’s go get you some lingerie!” Sarah looked devious.
“Why the fuck would I need that?” He scowled.
“Well, girly. You’re pretty well endowed.” Sarah grasped his breast forms, “And my bras simply won’t cut it for you, plus I don’t have enough to share with you, since you’ll be in girl mode for the foreseeable future.”
Those words burrowed into Aaron’s mind, “Foreseeable future”
It hadn’t really occurred to him that he’d have to stay as Erin for any amount of time, but she was right. Aaron didn’t have much at all, but Erin had responsibilities. She had a job, debts, a pretty creepy boyfriend of sorts. The thoughts took over, and Sarah grabbed him as she dragged him to the store.
Aaron was in a haze as he was brought into the store, piles of bras and panties piling up on his arms. Sarah brought him to the changing rooms, and his mind was still in a haze. He didn’t even hear it when the attendant said, “There is some drying paint in the fitting room, so be careful.”
He snapped out of it when he was in the room, and he took off the booty shorts, crop top, bra, and panties, hanging them up on the wall, not realizing that they were now covered in wet paint. He looked down and grabbed the first pair of panties and bra that he saw. It was a thong, and he slipped in on over his first pair of underwear that kept his junk from showing itself. He winced a little as it naturally rode up his ass crack, but he kept going, adding the lacy push up bra to his chest, clipping it on in the back.
As he was doing this, he heard something from outside the fitting room. It was Sarah on the phone.
“Right now?? Fine, I’ll be there in a second” Sarah said, and Aaron heard footsteps.
Oh shit.
Aaron grabbed the clothes from the wall and looked at them in horror, seeing the wet paint staining them. He couldn’t wear them anymore, but he had to think fast. He was still wearing the heels, so he figured he’d at least have shoes on to find her. He burst out of the fitting room and the attendant was super confused. Aaron looked around and saw that she took the bags with her.
“Where did she go?” Aaron said.
“I.. I think she went to the food court, Ma’am” The attendant was still weirded out by this, but Aaron booked it.
The heels slowed him down substantially, but with a click, click, click, he was moving fast enough. His adrenaline had kicked in, thinking about what would happen if Sarah had just abandoned him. He noticed a bunch of heads turning as he ran, and fully realized that he looked like a really attractive woman in lingerie and heels running through the mall. He tried to power through, but that thought made him lose focus and trip. He braced for impact, but something, someone caught him.
He looked up to see a heard of high school jocks standing over him, one of them holding Aaron in his arms. “Why hello there, babe. What’s the rush?” One of them asked, winking.
“I..I” He tried to get out, but a finger of that boy touched his lips.
“Don’t speak, it’s ok.” The boy said, coming in hot for a kiss.
Aaron, being held, didn’t have much recourse so he just closed his eyes, letting this boy’s lips touch his. It was gross, and Aaron gagged as he tried to stick his tongue down his throat, but he accepted it, trying desperately not to make it last any longer than it needed to.
The boy pulled away, and Aaron bounced up, continuing on his run. He went to the food court and saw something out of the corner of his eye.
It was the jocks again. Aaron started running, bursting out the front door looking like a madwoman in his bra and panties. As he took a breath, he saw a car pulling up. It was Sarah’s car. The door opened and he hopped in.
“Oh my god, mom. Why are you in just your underwear!” Sarah questioned.
“Wet...paint” Aaron exclaimed between pants. He looked up and saw another girl. Madison. She was Sarah’s best friend, and she laughed a little bit.
“So, like, this is your dad?” Madison asked
“You told her?” Aaron’s face went red.
“Yeah, she knows the whole story. Don’t worry, mom, she’s cool!” Sarah said.
“But why did you leave me?” Aaron asked, red with anger.
“I’m sorry, mom. Madison called saying it was an emergency, but she was really just waiting outside the mall.” Sarah explained.
“Hey, at least we got all your cute clothes!” Madison squealed, gesturing to the giant pile of bags sitting next to Aaron.
“Where’s my phone?” Aaron asked.
Sarah pulled it out of her pocket, “Hey, Ted seems super sweet. I’ve been texting him all day while we’ve been shopping! You got a date with him tomorrow after work!”
“Like hell I do!” Aaron yelled, and Sarah handed him back his phone.
He looked down at the screen and a DING rang out. Opening it up, it was from Ted.
The text read “So excited”
And the picture of his dick attached confirmed it.
Next Day?
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Becoming his Daughter's Mother
He becomes a single mother...but single for how long?
A man and his daughter move to a new town to start a new life but he didn't plan for it to be so drastic.
Updated on Feb 22, 2026
by takacube
Created on Jan 31, 2018
by Dayeandknight
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