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Free! Headcanon - How They React When You Blurt Out Your Insecurities
(A/N: I will likely, at some point in the future, write one for characters such as Kisumi, Momo, Nitori, Sousuke and any other character requested. For now, enjoy this one for the Iwatobi boys and the Matsuoka siblings.)
Makoto Tachibana
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He hadn’t expected you to blurt out your feelings of insecurity about yourself.
You were one of the most confident people he knew, even if he did know about your frequent anxieties over what he viewed as quite minor things (he knew and understood that they felt massive to you).
But, never in a million years did he imagine you’d be insecure about yourself, more specifically your body.
After all, you were his girlfriend. Even if his opinion may have been biased, he believed that you were the prettiest girl in the world, and there was no changing that for him.
Due to not expecting this outburst from you, he has no idea what to say.
He sits silently in place beside you, just watching your tears cascade down your puffy face.
That broke his heart.
Acting on impulse, he lifts your face and brushes your tears away with the backs of his fingers, before pulling you onto his lap (even if you protest).
He wraps his arms around you securely, resting his chin on your shoulder.
“(N/N), I know it doesn’t matter that I think you’re the prettiest girl in the world, and I know that I can’t change how you feel about yourself, but I at least want to help. I’ll do anything if it helps you, okay?”
You nod, and he kisses your temple again, smiling faintly.
Gou Matsuoka
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Gou freaks out a little.
Did she make you feel this way about yourself?
Did she do or say something to make you feel less than the perfect person she saw before her?
Regardless, she still feels like she has some responsibility as your girlfriend to make you feel like you are gorgeous. She feels bad for not being attentive enough to see that you were insecure.
“I think you’re beautiful, (N/N). How could you think so low of yourself?”
She wraps her arms around you, almost suffocating you in a warm, tight hug.
Like Makoto, she feels like she needs to help you feel better about yourself in some way.
“How can I make you feel better about yourself? What do you need me to do?”
“I-I don’t know.” you mutter in response. 
“Do you want me to tell you how pretty you are?”
“...I guess so.” you say sheepishly, cheeks heating up as you wipe away your tears. “Th-thanks, Gou.”
Rei Ryugazaki
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As one could guess, Rei isn’t amazing at comforting people.
Not to say he didn’t want to help you, or that he didn’t have the ability to make you feel better.
He so desperately wants to articulate how beautiful and wonderful you are, at least through the lenses of his red-rimmed glasses, but he just can’t.
However, he is caught so off guard, that he can’t help but blurt out: “Why would you think that about yourself, (Y/N)?”
“Because, I’m just not as pretty as other girls. It doesn’t matter if you think I am...Doesn’t change how I see myself...”
Rei just isn’t having this. In a moment of improvisation, he allows his thoughts to escape his mouth without thought.
“...You are beautiful, (Y/N). But, you’re human too, just like everyone else. All humans are imperfect to some degree, even if we all try to be as perfect as possible. But...your physical imperfections don’t denote your value as a person. They don’t make you any less beautiful, and anyone who treats you otherwise is no where near as perfect as you are.”
This brings a smile to your face, which had initially held an intrigued yet shocked expression. Sure, it couldn’t completely solve your problem forever, but it makes you feel a lot less insecure in that moment, and a little less insecure in the long run.
Though Rei had insisted no one was perfect, you can’t help but think that Rei is a perfect boyfriend.
Haruka Nanase
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Haru knows that you’re insecure long before you tell him.
As the most attentive and perceptive boyfriend you could’ve ever dreamed of having, he noticed every little thing you did, be it as subtle as a whisper caught in the wind.
This meant he’d observed, on numerous occasions, you pinching at your chub when you thought you were alone, or at least when you thought he wasn’t looking. He noticed how you always made sure to wear clothes that concealed as much of your body as humanly possible, even when you’d end up wearing what seemed to be winter clothes during the summer.
He simply listens as you lament about your self-hatred. His heart sinks a little with every word, but he’s glad you are comfortable enough to tell him about how insecure you are.
Haru’s always been a guy of few words, which is why he expresses his love for and adoration of you by wrapping his arms around your shoulders. He knows you’re smart enough to understand what he was saying. Whether you’ll listen to what he was saying through his actions is something he can’t predict.
He quickly realises that you listened when you bury your face in his chest, which soon became drenched by your warm tears.
Using his thumb, he caresses the back of your hand, and you feel a little more okay.
Nagisa Hazuki
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When you express your feelings of low self-esteem, Nagisa seems a lot more upset than you are.
You watch the tears prick in the corners of his eyes, thoroughly confusing you. 
“Why are you crying?” you question. Sure, you were upset, but not to the point of tears. Is he really that upset about what you’ve said?
“Because, (N/N), you’re so amazing. How could you not like yourself?!” he said between sobs.
“Look...you thinking I’m amazing doesn’t really change how I feel about myself.” you explain, holding back tears of your own; Nagisa being so upset about it breaks your heart just a little. “Raising my self-esteem’s something I have to do for myself, but you can still help me feel better when I’m upset about it, okay?”
Nagisa wipes away his tears and nodded.
Before you can do or say anything else, Nagisa pulls you into the tightest hug of your life. A few moments later, he holds you at arms-length. 
“I love you so much, (N/N).” he tells you, causing your heart to skip a beat.
“I love you too, Nagi.” you respond.
He grins at you and presses a kiss to your nose, causing you to giggle.
Your insecurities melt away for that night.
Rin Matsuoka
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Rin is overwhelmed when you blurt out your insecurities.
He’s always known you to be insecure, but he never knew how badly your insecurities affected you, especially because you often acted arrogant and confident.
Like Makoto, he doesn’t quite know what to say at first. Like Gou, he’s consumed by guilt, thinking he could’ve, somehow, prevented you from feeling this way. Like Haru, his heart sank. Like Nagisa, tears prick in the corners of his eyes. Like Rei, he’s not that excellent  at comforting people.
He just watches as you bury your reddened face into his pillow, as the both of you are sat on his dorm’s bed; you are completely embarrassed that you’d just cracked so badly in front of your boyfriend to the point of not wanting to look at him.
He really wants to stop you from crying and feeling so bad about yourself, but he just doesn’t know what to do nor say. This just amplifies his guilt.
How come he, the guy who was supposed to make you feel like the greatest girl in the world, couldn’t make you hate yourself any less?
You tense up when you hear a quiet whimper. You look up and see Rin watching you with tears rolling down his cheeks.
You look back at him.
“What’s wrong?” you ask shyly.
“I...I just wish there was something I could do to show you how I see you...” Rin says in a low voice, which wavers a little.
“There’s not much you can do or say to change how I feel, Rin.” you sigh, eyes locking to the pillow. You slowly look up at him. “But...I could kinda do with a hug...”
Within moments, Rin as his arms locked around you. He kisses your cheek and gently rubs your arm with his thumb. The hug’s enough to make you feel a little better.
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MASTERPOST
Lol I actually finished this, well as promised... a little late tho haha
Free!
Yamazaki Sousuke
realizing his s/o is his sibling
his crush confessing to him before leaving japan
Matsuoka Rin
comforting his s/o during a panic attack
his s/o rejecting his proposal
Giving his s/o a bj (NSFW)
Tachibana Makoto
scratch marks on his back (NSFW)
asking his friends to teach him how to cook
Mikoshiba Seijirou
Random fluff
Shower sex (NSFW)
Haikyuu!!
Akaashi Keiji
First bj (NSFW)
Kuroo Tetsurou
seeing his s/o flirting with Oikawa (NSFW)
Kageyama Tobio
soulmate as Oikawa’s cousin 
Iwaizumi Hajime
Soulmate AU (Butterfly)
Hinata Shouyou
As a nekoma student
Inu!Hinata (NSFW)
Oikawa Tooru
Prince! Oikawa with a penpal
having a thigh-high kink
Birthday sex (NSFW)
his s/o modeling lingerie (NSFW)
Jealous! Oikawa
Shimizu Kiyoko
Soulmate AU (tattoo)
Sugawara Koushi
Yandere!Suga
his s/o kissing his beauty marks (NSFW)
Sawamura Daichi
daddy kink (NSFW)
Shower sex (NSFW)
Yamaguchi Tadashi
getting a date as a dare
Azumane Asahi
Acidentally going rough (NSFW)
Tsukishima Kei
having a playlist for sex (NSFW)
being a tease (NSFW)
Tanaka Ryuunosuke
Sharing lunch with his s/o
Kyountani Kentarou
his crush liking foreign music
Aone Takanobu
sex with smaller s/o (NSFW)
Karasuno 3rd years at the beach Iwaizumi x Reader x Oikawa Aone and Ushiwaka Soulmate AU  Karasuno comforting their male s/o  Kageyama and Kyoutani first kiss  Kuroo, Oikawa, Kageyama and Tsukishima with their s/o random angst Kuroo, Oikawa, Kageyama and Tsukishima with their shorter s/o in the shower (NSFW) Iwaizumi, akaashi and suga breaking up with their s/o because of an arranged marriage  Karasuno with their s/o accidentally hitting a serve at the back of their head 
Kuroko no basket
Takao Kazunari
winter fluff
confessing to his crush
Aomine Daiki
Bubble bath with pregnant wife 
giving advice to his son
Werewolf!Aomine (NSFW)
Prom AU (NSFW)
Cheating on his pregnant s/o 
Soulmate Au (sharing physical pain)
comforting his s/o afraid of the dark and storms
falling for a tsundere and them trying to get him to class
Valentines
being insecure about not being romantic enough
Affectionate Aomine (NSFW)
Akashi Seijurou
his s/o having a club
Parent AU
Arranged marriage with his s/o
King!Akashi and Bodyguard!Reader (pt.1, pt. 2, pt. 3)
S/o similar to his mom
Helping his s/o sleep
Circus Date
Kuroko Tetsuya
having an s/o with less presence
Soulmate AU with momoi’s best friend
his s/o wearing his jersey (NSFW)
confessing to his crush
Meeting his s/o at the park with nigou
Kuroshitsuji Au (NSFW)
Hara Kazuya
having a vocalist s/o
Kise Ryouta
Arguing with his s/o
Quoting from movies
trying to cuddle with his s/o
liking the tsundere kaijou team manager
meeting his singer idol
his crush liking kasamatsu
Mibuchi Reo
Body worship (NSFW)
Kagami Taiga
having a sensitive chest (NSFW)
Rough sex (NSFW)
Gentle sex with rape victim!s/o (NSFW)
Midorima Shintarou
using his lucky item to shut up Takao
his crush liking his eyes
Kasamatsu Yukio
his first kiss being interrupted
his small s/o beating someone up
Kiyoshi Teppei
Casual sex (NSFW)
his s/o giving him a lap dance (NSFW)
his s/o giving him a massage
Izuki Shun
liking someone who likes his puns
casual fluff
Murasakibara Atsushi
Bakery Au
having a smaller s/o
Hanamiya Makoto
confessing to his crush
Hayama Koutarou
Dry humping his s/o (NSFW)
GoM x Reader KiriDai x Reader Seirin reacting to their manager liking Riko’s cooking Kagami x Reader x Aomine (pt. 1,pt. 2) Akakise Parent AU Gom and Kagami with their s/o having affectionate friends Imayoshi, Aomine and Kiyoshi with stressed s/o Kasamatsu and Kagami liking the same girl Kiyoshi and Kasamatsu asking their team for advice to ask out someone Akashi, Hanamiya and Murasakibara finding their chubby crush being bullied Akaashi, Kuroo and Hinata with Dom s/o (NSFW) Iwaizumi and Akaashi realizing they are in love Someone being interested Akashi’s (Bokushi and Oreshi) skills GoM with their foulmouthed s/o being catcalled GoM, Kiyoshi, Izuki and Hanamiya and their sweet s/o having a darker personality/side UK, Kagami and Kasamatsu with their s/o being buried in snow GoM, Kagami and Imayoshi and their s/o beating up someone during their date GoM (- Midorima), Kagami, Kiyoshi with their cuddlebug s/o Kagami, Nebuya and reader having an eating contest  Aomine, Imayoshi, Akashi, Midorima, Takao, Kise and Hayama with their s/o pulling the cheating prank GoM, Kagami and Himuro with a yandere gf  (pt. 1,pt. 2) GoM and Kagami and their s/o using their gift to kill a bug
pillow talk
Kasamatsu, Takao and Izuki
Gom, Kagami
GoM, Kagami and Himuro finding something their crush lost Gom and Kagami deciding with their s/o to adopt a baby  GoM (-Murasakibara), Kagami and Kiyoshi inviting their s/o to their house UK and Akashi trying to get the attention of a shy foreign student GoM jealous of their s/o befriending (Haikyuu!! Guys) Makoto, Sousuke and Mikoshiba Seijirou underwater kiss Midorima, Kiyoshi, Himuro, Aomine,Oikawa, Daichi, Sousuke and Mikoshiba Seijirou with their insecure s/o GoM and Nijimura, being attracted to a girl’s smell in the train  GoM, Izuki and Kagami with their s/o pushing them down then cuddling them GoM and Kagami climaxing before their s/o (NSFW) GoM reacting to their crush actually dating Nijimura  Aomine, Kise, Kagami and Akashi with their s/o in a onesie
YoI
Victor Nikiforov
skating with his clumsy s/o
cuddling (NSFW)
liking a skater who practices before Yuuri
teaching his s/o how to skate
meeting his s/o in hasetsu
Yuri Plisetsky
pet shopping with his intimidating-looking s/o
jealous yurio and drunk s/o
30 day writing challenge (1.1, 1.2, 2, 3, 4, 5.1, 5.2, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21/23, 22/24, 25, 26, 27, 28, 29, 30) *NSFW for day 5 and 25*
Oikawa and Kise finding out their crush has a long-distance relationship with the other
Haru and Kuroko, Midorima and Rei, Makoto and Suga, Nagisa and Hinata, Rin and Aomine liking the same girl
Sousuke, Bokuto and Kageyama being teased (NSFW)
Hayama, Akaashi and Kise Yakuza AU
Mikoshiba Sei, Kagami and Kiyoshi College AU
Haru, Momo, Kisumi, Kageyama, Kenma, Kuroko, Murasakibara, Himuro, Hanamiya and Mibuchi and their s/o jokes about breaking up
Kasamatsu and Iwaizumi’s crush confesses to them
Suga, Kageyama, Kiyoshi and Makoto with their sickly childhood friend
Makoto, Kiyoshi and Suga comforting their s/o after a conflict with their parents about college true
Oikawa, akaashi, kuroo, aomine, kise, Akashi and nijimura found cheating by their fiance
Makoto, Sousuke, Mikoshiba Seijirou, Midorima, Himuro, Mibuchi, Kiyoshi, Oikawa and Daichi cuddling with their s/o in the shower/bath
Tokyo ghoul AU
Kuroo, Tsukishima and Rei
Oikawa, Kise and Rin
Sousuke and Kiyoshi with chubby reader
Haru, Momo, Kisumi, Kageyama, Kenma, Kuroko, Murasakibara, Himuro, Hanamiya and Mibuchi confessing to their crush
Oikawa, Daichi and Mikoshiba Seijirou random fluff true
Makoto and Suga liking someone boyish and intimidating
Akashi and akaashi breaking up with their s/o because of an arranged marriage meeting them years later
Rin, Oikawa and Aomine finding out their s/o’s passion but is shy to show to others
Otter ask(s)
Mitobe, Izuki, Kogane, Kasamatsu, Sakurai and Imayoshi
Mibuchi, Hanamiya, Hayama, Nebuya and KnB girls
Midorima, Karasuno 3rd yrs and 1st yrs (-Hinata)
Bokuto, Kiyoko, Nijimura, Kiyoshi, Nitori and Gou
Aomine, Murasakibara, Nagisa and Kenma
Mikoshiba seijirou, Sousuke, ennoshita and Oikawa
Tanaka, Kuroo, Kagami, Akashi, Rin and Momo
Kuroko, Kise, Hinata, Noya, Makoto and Haru
Midorima, Kiyoshi, Himuro, Aomine, Oikawa, Iwaizumi, Daichi, Mikoshiba Seijirou and Sousuke with their s/o falling asleep on their chest
Himuro, Aomine, Midorima, Kiyoshi, Makoto, Sousuke, Daichi and Iwaizumi reacting to their s/o asking for cuddles
Makoto, Sousuke, Mikoshiba Seijirou, Oikawa, Daichi, Midorima, Kiyoshi and Aomine modeling for their artist s/o
Sousuke, Akashi, Himuro, Nijimura, Tsukishima and Kageyama react to being rejected
Oikawa, Daichi, Sousuke, Mikoshiba Seijirou, Makoto, Aomine, Kiyoshi and Midorima with their s/o modeling lingerie for them
Haru, Nagisa, Nitori, Kageyama, Hinata, Kuroko, Imayoshi and Aomine reacting to their gf not wearing underwear 
Kuroo, Aomine and Sousuke with their s/o falling asleep in the middle of kissing
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