Disclaimer: All characters are 18+. This is a slower story with buildup, don't read expecting for a quick fix. Enjoy!
Rachel had always loved fashion. When she was younger she would dress up, asking for the prettiest pink princess dresses for her birthday or begging her mom to take her to the mall. Now that she felt like she was all grown up at 19, she figured it was time to start dressing more mature and to ditch her old clothes she'd throw on for high school. Now that she was going off to a university about 40 minutes away from home, Rachel wanted new clothes to "reinvent" herself. She was always too focused on her studies and never had time for anything else.
The good news was that her mom, Iona, loved fashion as well. With two walk in closets in their house mostly filled with Iona's things, Rachel should've had a plethora of outfits to choose from. Iona would constantly change styles and shoved her old clothes into the back of her closet, never to be seen again.
The bad news was that Rachel couldn't fit in any of her mom's clothes. Rachel was only two inches taller than her mom at 5'7", she was heavier than her. Iona's jeans never comfortably went over Rachel's plump ass and some of her shirts never completely covered her stomach. Thankfully, they were both C cups, but all of Iona's bras rarely reached all the way around Rachel's back.
While Rachel could've just bought her own clothes, she quite liked Iona's old outfits, whose styles' didn't seem to be sold anymore. University was also expensive. Very expensive. So outside of spending money on textbooks, school supplies, parking, and much more, she didn't have any extra for clothes.
Thankfully Iona's clothes were in various sizes, and with just a little weight loss Rachel felt that she could fit in some of them. But she just loved food too much and working out was exactly that, too much work. She had tried before, feeling that it was just too hard by herself. She did have one person she could turn to. Her older brother Flynn.
Flynn was 23, fresh out of college and working as a physical therapist. He had been a little chubby during high school, but at the end of his four years in college, he was in great shape. If anyone could help Rachel slim down, it would be her brother. They'd always had a close relationship, even going as far as to talk to each other about their dates as well as some more... intimate details. Flynn had more than once shamefully thought about his sister getting felt up while stroking his cock right before bed. He thought she was beautiful with her nice round ass and a handful of tits. Rachel had modeled her mom's clothes for him before and he had more than once had to hide his erection after seeing her bend over in a miniskirt or the one glorious time the buttons had popped from a too small blouse.
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He was working out in the gym when Rachel came in, sporting some flowy shorts and a tank top with a built in bra. Their summers got hot at times and he could see sweat glistening on her forehead, at the edges of her black hair which was pulled back into a ponytail.
"Hey Flynn," she said, covertly admiring his straining muscles.
He finished standing up out of his squat and dropped the bar back onto the rack before replying.
"Hi Rach," he said grinning, happy that something broke the monotony of his workout but mostly because he truly enjoyed talking with his sister.
"So... I've been thinking. I want to lose weight so I can fit into mom's clothes."
"And..." Flynn replied, waiting for her to continue.
"And I was hoping you could help me. Keep me accountable and whatnot."
Flynn laughed. "You sure? Remember what happened last time?"
Rachel, thinking about how the last time she asked him to help left her running to her room crying, nodded her head.
"I've got four months till university starts up and I'd like to be able to wear mom's stuff. Look like a proper college girl and whatnot."
"It's gonna be hard," he said thinking. "If I do this, then no quitting. You do it until you reach your goal or you don't do it at all."
"You have to commit as well then. No quitting on me."
Flynn stuck out his hand at Rachel, happy to be able to help his sister out. She didn't ask for much. Rachel shook his hand with a smile on her face, blissfully unaware of where this agreement would take them.
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"Try and keep your back more straight," Flynn instructed, standing on Rachel's toes. She'd wanted to start with abs even though he had planned a full week split full of a mixture of weightlifting and cardio. He didn't know where she got the notion that abs and legs were all that mattered when women trained.Β At least she had shown up in something cute. She'd decided to spend her hard earned money on some quality olive green biker shorts and a matching sports bra. With pockets of course as she'd proudly showed him. She figured that if she had to suffer, at least she would do it in comfort and style. The shorts were high waisted and had a 2 inch inseam, showing off her longer legs. It had a seam in both the front and back and accentuated her butt. Her top completely covered her cleavage and gave her some much needed support.
Flynn had been impressed with the quality of the clothing, "inspecting" it for any flaws but finding none. There weren't any visible panty lines either. He spent half the workout trying to find any, impressed at the quality of her shorts. He knew she was wearing panties too; Rachel wasn't the type of girl to go commando. But Flynn on the other hand, was the type of guy to go commando. He was in a gray t shirt and black shorts, refusing to change his normal workout clothes even if his sister starting working out with him. His briefs felt too constricting while working out.
He was a shower, not really a grower and most of the time it was too uncomfortable to tuck his cock into his waistband, and he risked flashing cause his head was always poking out. Instead he just let it hang, usually down the left side of his shorts. It left a little bit of an outline, a detail that Rachel almost immediately noticed, blushing at the fact that she did. Flynn would have to be careful about how he demonstrated his planned lifts.
Their workout ended with Rachel face down on her yoga mat, exhausted by just a 30 second plank. Her arms were up and her legs spread, giving Flynn a nice view between her legs, telling himself he was just checking out her new clothes. He concluded that they truly were of high quality as he couldn't see even a hint of cameltoe despite the shorts being pulled up tight.
He patted her back, his hand touching the slightly sweaty part between her shoulder blades and bra straps.
"That was a good first workout. Make sure to refuel with the meal prep I left you in the fridge so you're ready for your cardio session in the afternoon."
Rach just groaned in response, comforted by the fact that at least she could wear her cute new running shorts which would pair nicely with her mom's old sports bra. A looser black pair of shorts with some blue accents and a light blue sports bra that showed a little more cleavage than the one she was currently wearing. She hobbled inside to see what Flynn had made her.
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After a trip to the mall with her friends she'd gotten back home to eat her dinner, her last meal for the day. She sat at her regular spot between her mom and Flynn, her younger brother Max, and her dad, Carl, sitting across from her. Despite their one year age difference, Max was the same grade as Rachel and was going to the same university as her. The family had been surprised at his choice; he was a bookworm with almost perfect grades and could've gotten into more prestigious schools with his accomplishments. He had stated that he wanted to be close to home, but Rachel felt that he wanted to be close to her. They had a close relationship just like between her and Flynn, albeit a little differently. They'd talk about books and she'd ask him any questions that popped into her mind. They strayed away from talking about dating, with the exception of his ex girlfriend who he dated right after turning 18, but that only lasted a couple months.
Everyone stared at Rachel's plate as she sat down with it. Iona was a wonderful cook, part of the reason why Rachel couldn't fit into her clothes. The family was sitting there, large plates of prime rib with various sides, even Max had a sizable chunk. Rachel's plate was dwarfed in comparison, just a small mound of rice, a couple slivers of prime rib, and the other half of the plate filled with unseasoned green beans. Rachel looked up at her family.
"Don't ask," she grumbled, digging into her meager meal.
An hour and a half later, Rachel and Flynn were stretching on the sidewalk in front of their house. Flynn had reluctantly put on compression shorts since they were running, though he had to stuff his cock down the left leg of the shorts and still left a slight outline when he brought his left leg forward. Rachel had noticed again.
"Just an easy half mile walk to warm up, a mile jog, and then a half mile cooldown walk back home," Flynn said.
Rachel nodded, trying to psych herself up for the workout, already thinking about new cute running sets she would need if she regularly ran.
The first walking part started off well. Only halfway through the mile Rachel was breathing heavily, not that Flynn really noticed. He was too busy watching his sister's breasts bounce in her mom's sports bra to notice. This pair didn't nearly have enough support and he kept glancing over. He probably could've flat out stared at her chest with how focused she was.
She'd barely recovered by the time they got back to the house. Still exhausted, she looked into her brother's green eyes and nodded.
"Thanks," she said sincerely.