How to Train Your Brother by Jessajess99

After a recent development disorder leaves him much shorter than he used to be, Reese has become academically demotivated, and worries he won't receive his diploma in his final few weeks of high school. But his sister, a recent college graduate who's twice as tall as him, moves back home. Her arrival sparks a change in Reese's attitude to start treating his family - and particularly his amazon of a sister - a lot nicer than anyone would reasonably expect. Eventually his sister realizes she might be able to save him from failing his senior year, and Reese does his best to more than thank her in return.

There was some kind of spam attack on the website which is why I have over a thousand reviews now. I don't know who all was targeted but I know Step Monster by Asukafan2001 also got a thousand spam reviews too. The site's owner deleted them but I guess it still thinks we have a bunch. That's all I know :/

Categories: Giantess, Teenager (13-19), Young Adult 20-29, Breasts, Butt, Entrapment, Feet, Footwear, Gentle, Humiliation, Incest, Instant Size Change, Legwear, Muscle, Odor Characters: None
Growth: Amazon (7 ft. to 15 ft.)
Shrink: Dwarf (3 ft. to 5 ft.)
Size Roles: F/m, FF/m, FM/m
Warnings: This story is for entertainment purposes only.
Challenges: None
Series: How to Train Someone in 23 Days or Less
Chapters: 61 Completed: Yes Word count: 169935 Read: 530396 Published: November 15 2019 Updated: October 09 2021
Day 1 by Jessajess99

Chapter Notes: So for those of you who are unaware, I've been planning on writing three versions of this story since before I even published the first chapter. The name of the series (How to Train Someone in 23 Days or Less) basically came as an idea because I wondered, if someone was initially shrunken at different sizes, would you be able to subtly and unawarely them into submission quicker? But also, would you be able to make them do a lot more things you wouldn’t ordinarily get them to do? Like would they be more submissive to you? So I basically wanted to make multiple variations of the same story, with the same characters and backstories and life events and everything, but have one that’s like the baseline version that gets a little fun but is rooted in realism, and a second (and eventually third!) version that’s a lot more wild. Then people can choose which version they want to read (or, if they’re like me, they’ll read both). But based off what people seem to like on this site I’m sure most will enjoy the second version a lot more lol 

Basically, if you stuck around this far, you'll probably like what I have in store next. I'm starting the story over, but a LOT of new stuff is added in. And everything happens in 19 days instead of 23 so there's less "filler chapters." Reese is now half of Olivia's height, and she's a bit more mischievous. The first two days are mostly the same, but some stuff changes up on the third day, so I’ve published the first three chapters. But it's also been so many months since I published the first chapters that a re-read of them might not hurt since there's some new details. My hope is that if you were patient enough to stick it out through this first version, then you’ll be willing to give the second a try. It’s a lot faster-paced I think and some fun stuff happens early on. 

Thanks to all the fans!



Sunday, May 16


     “Hellooooooooooo!” A clean red Camry pulled up next to the curb of an upper class American home, positioned squarely in northern Oregon suburbia, as the voice of a rambunctious girl cried out, alerting the house's residents. A well groomed couple in their late 40s came rushing out seconds after the youthful cry, smiles wide. 

     “You’re finally here!” called out Tracy, a conservatively dressed woman with bootcut jeans and a grey knit cardigan that hid beneath a large apron with flour spilled all over it.

     “She’s back!” announced the man, excited to see his daughter return to live with them again, like a trip down memory lane. Stuart perfectly matched his stereotypically suburban cookie cutter wife. Situated like any classical interpretation of a man, he held tongs in one hand and a spatula in the other, the top few buttons to his plaid shirt open from having worked too closely over a grill for the last half hour.

     The driver side door opened, and out stepped the child that the two parents had eagerly been awaiting all day, a 22 year old exercise physiology major freshly back from college named Olivia. She was dressed similarly to her mom, but with enough difference that anyone who knew what style was would be able to identify she was the more chic of the two: her thin pink sweater more than complimented her form-fitting, pale blue jeans and black and white checkered sneakers. She was a mix of Urban Outfitters and Forever 21, while it was evident that her mom still frequented Nordstrom Rack.

     A set of small, anxious eyes watched from the window as the recent graduate gave her parents a warm hug that nestled their heads against her shoulders. Her parents were both of average height for their age, but Olivia stood taller than even most men at 6’6. 

     “You haven’t grown again, have you?” Stuart asked, stepping back to adore his statuesque daughter. 

     “Just an inch,” she said, her rolling eyes communicating the frustrating familiarity she had with that question nowadays, no matter the level of acquaintance from the people who would ask. But a proud smile let her parents know she didn’t mind. Not for them. 

     The pair of eyes belonged to the last member of the family: Reese. His body had manifested a developmental disorder a year ago that left him at an unfortunate 3’2. He was lucky that it had stalled there, but he was still over two feet shorter than most of the other guys his age, and less than half the height of his sister. Both facts had been incredibly demotivating for him. His family had been unaware that he was genetically predisposed to develop the illness, and he was the only person at his school who had it. Reese had just started to feel like he was growing into himself and his personality as his junior year of high school came to a close, so to have had this problem come about right as he was starting his senior year had meant a major blow to his self esteem. The last time he had seen Olivia, just a month after the disorder had started its work, he had only lost an inch of his previous 5’11. He was optimistic that it wouldn’t be that bad. Most with the disorder only shrunk a few inches, which obviously, while not ideal, wasn’t the biggest of problems. But the disorder worked its worst over the winter, and even though he seems to have stopped, he was legally classified a dwarf. Hell, even most little people were taller than him though. Dammit. He hadn’t attended his sister’s graduation last week with his parents because he didn’t want to have to face his sister given his new height (and, unbeknownst to him, her recent addition of ‘just an inch’). She was twice as tall as him. Even the most athletic players at his school couldn’t boast the naturally given height of 6’6, although a few came close, so Olivia was literally the tallest person in his life, and now he was about to live with her for the next month. It shouldn’t have come as a surprise that she would want to travel back home for a few weeks before setting off on wherever her adult life took her, but it irked him nonetheless. She was never that far from home anyways; she loved her hometown, her little place in the Pacific Northwest. Would he really have been able to avoid her for the rest of their lives? A normal, close family like theirs? Of course not. It’s only a height difference anyways, he told himself. She didn’t kill anyone. I didn’t kill anyone. It's no big deal. I have to face tall people all the time in school anyways. But those people weren’t more than three feet taller than him. And they obviously weren’t the sister he grew up with.

     Reese opened the door slowly and made his way out onto the driveway. His sister and parents heard the door opening and turned around, beckoning him over. Olivia stretched out her arms, even though she wouldn’t actually be able to hug someone of his size. But she smiled widely at the sight of her little brother nonetheless. Don’t act like it’s a big deal and it won’t be, he thought. 

     “Reese!” she called out lovingly. “I missed you at graduation.”

     “Hey, yeah” he said, with a convincing smile as he walked towards her. “I had an important essay to finish for AP Lit, sorry.” 

     “Reese has been working a lot on his homework lately,” Tracy chimed in. “I figured his final year of high school would be a breeze since he’s almost done for good, but his report card had a lot of C’s and D’s when we checked.”

     He hesitated, slowing slightly as he approached his sister. His sister would've had some of the largest boobs he'd ever seen on a person if she was normal size, but the fact that she was basically 25% bigger than all the other women around her made her tits even more massive. But now, as he stood at only half her height, they were so big that he felt awkward just looking anywhere near her upper body. Her thighs, poised firmly before him, were thick - easily wider than his own torso. Normally, he’d do his best to hug his sister; despite their new height difference, he had always gotten along well with Olivia. But even after a year with the disorder, the height difference was a lot to take in. Reese recalled a tweet he had seen that one day everyone’s parents put them down and never picked them back up again. One day I gave my sister a normal, ordinary hug, and didn’t realize I’d never be able to do that again. His big sister’s imposing frame was enough to give him pause, but the main thing causing him to hesitate giving her a hug was that he was right at eye level with–

     “Oh, come here!” squealed Olivia as she bent over, gently placing her hands his upper back and head, and pressed him into her lovingly. She didn’t want to squat down to hug him like people do with children, since she figured that might be humiliating for him. But as she cupped his head instead and nuzzled his rough, curly hair her body, she didn’t realize he was feeling humiliated in another way. 

     Reese was startled but barely polite enough not to recoil as he his sister softly pulled him into her ‘embrace,’ squishing his head against her crotch. How does she not realize how weird this positioning is? he thought, just the littlest bit scared, as his head was forcefully snuggled against the rough texture of her jeans. He looked up at her in an effort to change his head’s awkward positioning, but her large breasts jutted out just far enough away from her body that he couldn’t even see her face. She’s not even wearing a bra, he noticed. Or maybe she is, but I can’t really tell since I’m too short to even see if her nipples are poking through. He quickly shuddered upon this thought, trying to wipe the image of his sister from his mind. But he was right, she hadn’t been wearing a bra. Spending several hours on a road trip (just as summer was starting to heat up) with nobody else around tends to make any sane girl realize there’s no point in constraining herself.

     Reese gave the hug a few more seconds, his arms wrapped around her hips but unable to reach around while her hands laid against his neck, before he started to pull back to give himself space again. Olivia wasn’t quite done though. “I was worried about you,” she said, her eyes closed as she remembered back to her days of college. She really had worried for him, and her hands increased their pressure on him just a little. “You barely snap me nowadays. You can still use a phone right?” Of course I can use a phone, he thought bitterly. I’m not THAT small. But he couldn’t put it in his pocket like normal. He had to buy the smallest iPhone version, and even then it was sort of like using a tablet for him.

     “Oh, he’s probably nervous about his new height,” Tracy chimed in. “It probably isn’t easy being small either.”

     “No, you can’t tell my height from a selfie,” Reese retorted defensively, successfully escaping Olivia’s grasp this time. “I’ve just been busy. Or something. I don’t know.” Tracy had been spot on.

     “Too busy that you can’t spare 30 seconds to take a picture every few weeks?” Olivia said, hands on her hips as she looked down on him disapprovingly. He gulped, slightly off-put by this intimidating gaze and judgmental stance from his amazonian sister.

     “You don’t snap me either. So… we’re both at fault, if you’re mad.”

     “You’re back for barely two minutes, and the two of you are already bickering again,” Tracy commented, unsure whether to chuckle or sigh out of exasperation.

     Olivia sighed and rolled her eyes, but Reese couldn’t tell if it was from resignation or frustration. “I’m not mad, I just missed you. You don’t need to be so defensive.” He wanted to fight back but knew better. He hated when people called him that. Defensive. Even if he was in the right, disagreeing with them would only seem to prove their point. Besides, he was trying to keep a good attitude lately. His mom was right about his last report card, it did have several bad grades. But now they were lower. He was flunking in his art, history, and literature classes, the latter two of which he had to pass in order to qualify for his diploma when school ended in a month. He wasn’t sure what he’d do if he didn’t. Retake the year and be a super senior? He could only imagine the taunting he’d get then, being the oldest student and the smallest too. Or would he study up for a few months and just take a GED test? That second option didn't seem like it would be a good use of his time anyways, if he was already having trouble studying for his current classes. Why did he even need to pass high school anyways? Because networking and social skills won’t get me a good job at this height, he thought, not for the first time. I still need to go to college. Either way, his parents’ attitudes were normally pretty reflective of their environments, and he was confident that if he was at least a “good kid”–not just good, but someone happy and obedient, who they liked to have around for more than him just being their son–then they might be lenient on him come this summer and whatever came after it. So for the past couple weeks, and for the next month or so, he was committed to being as good of a son (and brother) as he could be.

     Reese smiled as he looked back up at his sister. “Yeah, sorry. I’m glad you’re home though,” he said, and gave her a second quick hug, this time around her thigh since it was closer to his size (and wasn’t as awkward of a position, obviously). 

     Olivia smiled back, nothing but love and sincerity in her voice: “Me too.”

     “Do you need any help with your bags?” Tracy inquired. “Reese, why don’t you get her stuff for her.”

     Olivia spun around, eyeing the allotment of duffel bags and suitcases in her backseat. “If he wants to, I won’t complain, but are you sure he’s even big enough to–”

     “OK,” Reese intervened, eager to make himself seem useful and rid everyone’s memories of his small but argumentative spirit just a minute before. And I absolutely AM big enough to help her out, he thought. His parents hadn’t even said anything, or so much as changed the joyous expression on their faces, but he knew from past experience that they shared Olivia’s general stance that he could be stubborn sometimes. Who’s the nicest celebrity? he wondered as he pulled hard against the door handle to open it, taking in all of Olivia’s stuff. Tom Hanks? Taylor Swift? Terry Crews seems to be a good dad. Maybe Ed Sheeran's just faking his nice guy persona to sell more albums. There were two suitcases stacked on the back seat across from him, with a third leaning against it, and a cheer bag on top of that too. Fuck, they’re almost as long as I am tall. Maybe longer. Olivia barely had enough room to look clearly through her rear view mirror while she was driving. “When I go on vacation I just have the one bag,” he mentioned, climbing onto the first step of her car so he could reach a duffel bag on the top of the luggage pile, emblazoned with years of memorabilia across it. “Hell, sometimes I just pack everything in a single backpack.”

     “Yeah, I’m sure it’s easy for someone your size to get away with that,” she giggled. He blushed, rationalizing that he was like that before he shrunk, but he didn’t want to argue. “And I’m not going on vacation,” Olivia reminded him, watching him try to situate himself so he could safely pull at the straps of her bag without accidentally falling from his step. “I’m staying here until I can find an apartment downtown. Or maybe in another city. I don’t know yet.” She paused, watching him give the first few tugs at her bag. “Here, I don’t want you to fall backwards and hit your head.” She scooped her hands under his armpits and lifted him up and off. 

     “Hey!” he shouted, startled as his feet suddenly left the ground and he was moved from his position like a child. “What the fuck?! You — that’s — don’t,” he stuttered, utterly humiliated at having been easily picked up and set aside while he was trying to help.

     “I told you, I don’t want you to accidentally fall,” Olivia explained. She stepped in front of him so she could reach into the car, and bent over, sticking her head in the sedan. “I’m sorry if I embarrassed you or something, I didn’t mean to make you feel bad.” As she bent over, her butt suddenly jutted out, nearly hitting Reese in the head. Great, so I’m eye-level with my sister’s crotch AND her ass. His attention couldn’t help but focus on its sheer size. Even wearing jeans it was still painfully obvious to Reese that her butt was toned - hell, it was thick, he just felt uncomfortable admitting it to himself. He looked to the side after a few seconds, paranoid that his parents might be watching, or a neighbor. As she stepped back with a suitcase in one hand and a duffel bag in the other, her butt bumped into the side of Reese’s head. “Oops, sorry,” she mentioned, blushing along with Reese, who was just glad he wasn’t still facing forward to receive a face full of his own sister’s butt. She turned around, almost bumping into him again despite having just done so literally seconds ago. “Oh, right,” she said, looking down at him. She set a bag down, then turned and quickly grabbed another one, smaller, but still big compared to her brother. “Here,” she said, holding the smaller one out to him. He tried to stick his arms out under it, but that proved too risky with how wide it was for his shorter arms. It was also too long for him to be able to grip it at the sides. So he instead grabbed it by the strap at the top, his hands facing him like in a chin-up position. Olivia let go and he grunted as the weight of her stuff suddenly strained on his arms. She smiled and pivoted her heels as she grabbed her stuff back up and briskly headed towards the house, unbothered by the weight of the bags. 

     Meanwhile, Reese breathed shakily, struggling to carry just the one, as he slowly trudged his way inside. He was beating himself up inside for having agreed to help bring in her luggage, but despite having gotten used to the new sizes and weights of objects after his shrinkage, he didn’t anticipate just how heavy her stuff would be. Just because I’m half her height doesn’t mean I’m only half her strength and weight. It was a truth that he had learned at the doctor’s (and in math class). His height was nearly half what it used to be, but also his width, and length, whichever directions those pertained to. Three times the reduced distances. It wasn’t an exact science, since he wasn’t fully half his old size, something more like 55%. But generally everything weighed about 6x as much as it used to, according to something his math teacher taught him a few months ago. “Another six inches, and everything would be about 10x as heavy!” he excitedly proclaimed, as if it wasn’t a miserable, annoying fact of life for Reese to suddenly be incomparably weaker than even the scrawniest girls in his classes. “And if you had shrunk to 2’2 instead of 3’2, the world would be TWENTY times as heavy!” Reese was at least thankful he had shrunken even more, since some people got hit by the disorder far worse than him. Just to imagine having to use a ten pound iPhone, to struggle just lifting a glass of water to drink; as he finally reached the house and made his way inside, he thanked God that he didn’t have it worse. 

     As his parents followed Olivia back towards the house, he did his best to match their speed, but quickly realized that’d be impossible due to the weight he was managing. He glanced up the path towards Olivia, who didn’t display a single hint of a problem with carrying her two bags that were each much bigger than Reese’s. Her arms weren’t even straining, and he knew from having seen her in the past, she definitely had muscles under that skin. She wasn’t buff per se, but like most cheerleaders–and certainly one who was taller than 99% of people, girls and guys–she had to be quite physically fit, while still retaining the glow of stereotypical feminine beauty. 

     As soon as he got inside, Reese let go of the suitcase. Seemingly to close the door behind him, but really to give him respite for a minute. After turning back around, he saw his parents were back in the kitchen, tending to the food again, but he didn’t see Olivia. Or her bags. Is she already in her old room? He let out a big sigh, bending down to pick the suitcase back up before slowly making his way up the stairs.

     The sound of opening zippers came down the hallway, confirming Reese’s assumption. He brought back up his fake smile, then toned it down a few notches to not seem like it was too much, as he turned the corner into her room. She was kneeling, but was so tall that she still had to bend over to reach the clothes in her suitcase. He hadn’t realized how big the neck hole was to her sweater until now. Definitely not wearing a bra. 

     He faked a cough. “Um, here’s your uh, stuff,” he stammered, setting her bag down carefully as Olivia whipped her head up, oblivious to her chest’s display. 

     “Thanks!” she said cheerfully, and went back to ruffling through her clothes. Reese stood in her doorway awkwardly for a second, before stepping back to head towards his own room. “Wait!” called Olivia, looking back up. “You’re gonna get the boxes in the back too, right?” 

     Reese breathed in slowly, but not quite a deep breath, and not enough to make it evident he was any bothered. “Yep,” he said simply, and changed his course towards the stairs to head back down to her car.

     “Alright good,” she said with a smile, and stood up to start putting clothes away in her old, empty dresser. Reese bound down the stairs with the hundredth sigh of the afternoon, still able to manage using every other step on his way down. I can be nice for my sister. This will only take a few minutes. He arrived at the car and popped the trunk. A dozen boxes of different sizes had been hiding back there, and there wasn’t any room for a single more. Actually, truly nice people don’t have to tell themselves to be nice. Or give themselves ultimatums or reasons or whatever. They’re just nice. He grimaced to himself as he loaded a heavy box into his hands, unable to carry a second, and looked up at his sister through her bedroom window pacing around her room. I wanna be nice. 

     About 20 minutes later, most of Olivia’s belongings had made their way back to her, but there were a couple parcels on the bottom that he couldn’t even begin to lift. “There’s uh, a few other ones that I… couldn’t carry,” he admitted, knowing that if he were back to his normal size, they wouldn’t have been a problem.

     Olivia tilted her head, registering his the shame her harbored from his inadequate strength. “That’s OK, Reese, I can tell you got most of them,” she said with a smile. “Everyone’s got their limits, no need to feel bad about yours.” She squatted down to his level and gave her brother another quick squeeze, albeit still too long for his comfort as his cheek was pressed up against her breast this time instead of nearing her ass. Unfortunately for Reese, Olivia’s bubbly personality resulted in being a pretty touchy-feely person too. At least I won’t be able to see her careless fucking cleavage when all I can do is look from below. Maybe in a perverted, alternate world inspired by the likes of the front page of Pornhub, he would squeeze her right back, and savor her hug for more than was emotionally healthy for their sibling relationship. But Reese’s mind was in a good, rightful place, and each embrace he had shared with his sister today grossed him out. They weren't even and equal hugs, like hugs should be, heads close and hearts beating near each other. It’s not even that he was turned on by sharing that kind of literal headspace with his sister’s chest or with her crotch from earlier, but respectful enough to deny those feelings and allow them to gross him out. He just viewed his sister the same as he did any of his guy friends: a great person, sometimes with a bond as close as family (obviously in a literal sense in Olivia’s case), but with no sexual feelings whatsoever. He hoped that once she was more settled in, he wouldn’t have to hug her as much, but at least he didn’t have any doubts as to whether or not he was disgusted by any artifacts of his sister’s sexuality. 

     “You know I lived in an apartment at college?” Olivia asked him, interrupting his train of thought. 

     “Yeah I know,” he replied, “we visited a few years ago, remember?” 

     “Do you remember who my roommate was?”

     Should I have? he thought, trying to recall any and all of the people he had met while he visited. “Uh…” Shit. “Roberta?”

     Olivia scrunched up her face in confusion. “I don’t even know a Roberta. No, it was a trick question, I didn’t have a roommate.”


     “It’s just been awhile since I’ve had to actually live with someone.”

     “Oh. Okay.”

     “It’s a weird feeling I think. Like a step backwards.” Her thoughts trailed off into the conversation with her brother as she continued hanging up clothes in her oversized closet.

     “It’s just for a little while though, right? So, shouldn’t be a big deal, I guess.”

     She sighed. “Yeah.” There were certain freedoms that anyone who lives or has lived alone knows about. Even among her fellow college students, they were freedoms that she didn’t think were very common, since most of her friends had lived in the dorms, or saved some money by living with someone else. But she had appreciated the liberty that living alone provided. She hardly was alone anyways, always inviting people over and throwing parties and get togethers every other week (one such advantage: not having to worry about someone else’s night schedule). But still, the ability to be by herself and live independently was great. Watch whatever she wants. Listen to whatever she wants, cook whatever she wants. Say whatever she wants. 

     Wear whatever she wants. 

     She had read in a BuzzFeed article titled “23 Things To Do When You Live By Yourself For The First Time” that walking around naked was one such liberty. She only did it a few times though, despite the thousands of chances she had. It was certainly an… interesting aspect of independence. But she would obviously never do that at home. Hell, she didn’t even think she could walk around in her underwear around her family, especially her mom. Or dad. Or brother! Whenever she watched shows on Netflix where guys didn’t wear their shirts around the house, she always felt so confused. She couldn’t understand it. But that was OK. She never felt socially trapped by her clothes when she was younger like some nudist. Another advantage of living alone for several years means one can try out a lot of things for herself to know if they like them. It had been a few years since she last experimented with the idea, but yeah, that just wasn’t one of them for her. Not for now.

     “Oh yeah,” Reese announced, the one to interrupt her thoughts this time, “we have a new internet service by the way. The password is in dad’s office.”

     “Cool,” she said. “Actually, I think I’ll take a nap before I do anything else. Lotta driving today. Way too much. My legs are fucking sore.” She collapsed on her bed, sprawled out on her stomach. “Thanks for your help today. I definitely don’t remember you acting his normal when I was in high school.”

     “Oh, haha” Reese chuckled nervously. “Maybe it was hormones, probably. Or something like that.” 

     “You’re only 18,” Olivia reminded him, as she closed her eyes and nestled her head deeper into her pillow. “You’re still going through puberty. You’re just nice for whatever reason now.”

     He smiled weakly at her, even though she wasn’t watching him anymore. She was right. He was just a nice little brother now.

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