The news of the shiest boy in all of UA obtaining a girlfriend took the school by storm. Not only did Tamaki Amajiki score a girlfriend but he scored with the one girl who played the most difficult game of hard to get. (Y/n) practically threw herself at Tamaki. So... What made him any better than UA's resident dream boy?

Even Tamaki's best friends questioned that very same mystery. One thing for sure is that they've noticed Tamaki's anxiety levels skyrocket ever since and they weren't gonna stand for it. Luckily, only Mirio Togata had the guts to speak whatever came to his optimistic mind. "Are you sure that being in a relationship is helping you Tamaki?" The blonde narrowed in on the ravenette.

"How could you ask such a thing Togata!?" Neijire squeaked in astonishment.

"He's even more shy than usual though," Mirio gladly explained. He'd be lying if he said that Tamaki and (Y/n) weren't the perfect couple. They're downright adorable together! Even Tamaki felt little to no stress around her. He could laugh and smile and just be himself and she did the same for him.

"Oh man..." Tamaki sighed and forced himself into a corner of the room. At least walls were always there for him. They'd offered up the support and solace he'd need without complaints. Sometimes, Tamaki would find a corner and pretend he's being hugged, much like right now as his sides were sandwiched into a right angle. He can't stand tension as it was but now his best friends were fighting and about him too!!! Talk about awkward!!! Looks like inanimate objects will continue to hold up to their names as Tamaki's best friends.

Neijire began to float within the air with her balled up fists rattling parallel to her head. "He just has the new boyfriend jitters!!!" The girl cried out in her friend's defense. Although appreciative, Tamaki could sense that the girl was drifting ever closer to him making everything just that much more uncomfortable on his end.

"I've already taken care of the problem everyone , thank you!" Tamaki squeaked and forced hands to his elfish ears to block out the arguing as best as he could until everything was a muffled mess..

Mirio heard his friend loud and clear. "Problem..."

"Solved?" Neijire tilted her head.

"How... Seriously Tamaki what do you mean?" Mirio stepped forwards lying a strong hand upon his friend's shoulder. Tamaki, expectedly, flinched and spun around with a mouth all scrunched up. "Are you sure you're okay?" Mirio refused to leave his best friend hanging yet Tamaki's eyes were filled to the brim with glossy vexatiousness.

"Me and (Y/n) made a proposal..." The boy's voice shaked nervously. "OH WAIT NO!!! That's not what I meant! Not a real proposal!!!" Tamaki shook violently as he too began hiding his face behind two shell morphed hands. I'm a clam! I'm a clam! Hide and everything will go away eventually.

His two friend's could more than tell that something was eating at Tamaki and it wasn't the red glow of his elf ears that said that either. "What proposal?" Mirio questioned.

"To take the edge off... (Y/n) told me that we can... That we... That we..." Inhumane noises leaked from Tamaki's being.

"Spit it out Amajiki!!!" Neijire couldn't wait any longer.

"We're gonna have sex this weekend!!!" The boy shrunk himself down until he sat upon the floor in a ball. He can't believe he just admitted that for the whole world to hear. The most shy boy in the universe was gonna have sex! Come one come all for a front row seat. Scenarios like this were common for Tamaki. It's part of the reason why he shelters his own self to extreme degrees.

"Even I haven't done that!!!" Mirio exclaimed.

"I didn't think you actually swung that way," Neijire said whatever came to her scatterbrained mind. She didn't have a filter did she? "I thought you were only dating (Y/n) to hide the fact you were crushing hard on Mirio."

"WHAT!?" Tamaki was about ready to pass out. "I never- Mirio!? Why!? This whole time everyone thought I was gay?" No wonder why girls never like me...

"To be fair... You have a weird fixation with Mirio." His hero name was inspired by Mirio, he's best friends with Mirio, claims that if Mirio were to die that his happiness and hope would die with him. Sorry Tamaki but the facts are there.

"Awe... You do buddy?" Mirio was oddly touched by Nejire's false assumption and pats his friend over the back.

"Change the subject before I pass out..."

"Hope you and (Y/n) have fun this weekend!" Mirio exclaimed.

Neijiro was thrilled, "If the bed's rocking we won't come knocking!" DID SHE REALLY JUST SAY THAT!?!?

"I need new friends..."

The weekend came and the only thing it brought was Tamaki's skyrocketing stress levels. The thought of having sex sounded amazing even in Tamaki's anxiety ridden mind except it was even more anxiety that turned the very mention of sex into a nightmare. Tamaki's never seen a naked woman before, he almost always plugs his ears at the mention of porn and admittedly besides morning wood Tamaki has never been successfully turned on before. Tamaki's so afraid that his lack of knowledge in the sex genre will turn his girlfriend against him. If not that, his lack of knowledge will just straight out embarrass him in front of her! To top it all off, unless Tamaki's fighting in combat, he strays away from the idea of touching another human being. How exactly would you have sex without touching your partner? Exactly, it's impossible.

"So it's your first time huh?" Tamaki's girlfriend, (Y/n), just got done listening to Tamaki's ever growing list of insecurities and questions about today's activities. Although it came as no surprise to (Y/n) that Tamaki was a virgin, she was ever welcoming of the idea. His first time shall be the best! Luckily, Tamaki was completely honest and comfortable around her or else she never would've suggested sex in the first place.

Tamaki's mouth scrunched up a little at (Y/n)'s question and nodded justly. (Y/n) sat down beside the boy and held his hand. "Well, I can guide you through it! I really think that if you have sex every so often, your anxiety might get better. Sex and masturbating is the best stress relievers out there afteral!"

Tamaki was amazed with such a tiny little fact, "Do you really think my anxiety will lessen?"

"It might," she shrugged. "Again, Never know unless we try."

"H-How do we start the... The sex?" Tamaki's face flushed red. Everything he just said was wrong and sounded even worse coming out than initially thought. How do we start the sex? What am I, five? Even I should know how to english at a time like this...

"I want to make sure you're fine having sex with me. Or sex... In general. I know a lot of this is new to us- You especially." supportive and reassurring. Tamaki knew he chose his girlfriend correctly. Or, rather, she came to him and he rolled with the punches. Of course she'd never punch him unless he asked.

"I'm fine (Y/n)... I l-l-l-love you! I'm I'm glad you're not forcing this onto me!"

(Y/n)'s verbally awed before embracing Tamaki by his neck. The shy being returned the embrace. For some odd reason, Tamaki's fingers began to tingle, like he was dragging them over the screen of a tv, but he didn't think much of it before (Y/n) parted the embrace. She immediately got down to business much to Tamaki's surprise. Her sinful fingers undid the buttons on her blouse, one by one, top to bottom. Tamaki's orbs remained transfixed upon her chest, all saw was flawless skin beneath that white blouse. One thing he knew for sure was that (Y/n) wasn't wearing a bra beneath as most girls should. So scandalous! Maybe too scandalous? Tamaki shook frantically and diverted his gaze as it was all overwhelming. Tamaki expected everything to move forward in steps, not one huge leap forward!

(Y/n) sat her shirt elsewhere, yet she highly debated putting it back on. If Tamaki's gonna act this immature then was it even a bright idea to make him take such a huge step forward? "Tamaki?" (Y/n) hummed, her forearm concealed her breasts for the most part. Tamaki peeked his eyes out from between his fingers and was refreshed to find that she was still PG13. "Tamaki... I need you to take this seriously or else I'm just gonna leave."

Leave? Oh no!!! I don't want you to leave! Tamaki heard (Y/n)'s warnings and mentally told himself to put on his big boy pants. (Y/n) felt refreshed once she saw Tamaki's face go all serious as if he was marching into battle. "I-I promise to take everything seriously from now on," it was a promise that (Y/n) believed through and through.

"Okay," the girl shrugged and peeled her arm from her chest. Her mounds were perky, the buds hardening within the air.

Tamaki gulped loudly, before he went to make his first big step into adulthood. Boys are supposed to please the girl... Right? They use their hands and mouth to do it... I think. Tamaki was mentally facepalming as all the questions were attacking him at once. Just do it! A mental tug of war and beads of sweat later, Tamaki gained enough courage to allow his right hand to inch forward. The limb was mere inches away from grazing the soft flesh of (Y/n)'s mounds but the meat beneath his fingers were vibrating like crazy! Before he knew it, Tamaki's fingers began to morph into slimy red tentacles. His stomach lurched, his throat squeaked, his entire body jolting backwards. Tamaki had lost all control over his quirk and no matter how badly he didn't want his fingertips to be tentacles they kept their shape. "M-M-Maybe today isn't a good day-"

"You can use your tentacles to please me Tamaki!" (Y/n) stressed to get her point across but her boyfriend was petrified at the thought of using tentacles to please his girlfriend when he strictly views them as food and weapons. "Tamaki... Sweetie... I get that you're nervous. Your tentacles can please me though. I promise you that. Use them to... I don't know... To wrap around my arms for starters?"

"I... I can try," Tamaki, although against the idea, tried incorporating his tentacle fingers into today's activities. The idea of using them gave Tamaki an ease of mind as well. (Y/n) wanted to try new things and he viewed his tentacles as an extension of himself, the brave and courageous part of himself he deeply envied. It sounded less, well, nerve racking on his end.

Tamaki pointed his entire hand at (Y/n), his vine like fingers elongated and reached out toward (Y/n). Tamaki wanted to see just how much control he had over his tentacles and used them to comfort his lady. His index finger, or rather his index-icle, grazed her cheek. Although it was slimy to the touch, the skin was oddly soft and she enjoyed the texture enough to press the limb to her cheek with a shallow laugh. Tamaki took (Y/n)'s reaction as an affirmative to continue. A mental command told the tentacle to keep moving. The suction cups gripping against her cheeks released leaving the sensation of a million tiny kisses trailing down her exposed neck. As the limb traced her throat, her skin began sprouting goosebumps one after the other down her forearms. The limb continued to inch lower before his other digits joined in. One explored her collarbone, tracing the bone from shoulder to neck in an exploration as another found comfort in wrapping loosely around her neck like a scarf. While Tamaki's thumb tentacle remained immobile at his side, the last two slithered across (Y/n)'s chest to weave and rise with the shape of her breasts. (Y/n) found Tamaki's touch to be oddly comforting as each touch was as delicate as a feather.

"Does... Does this feel good?" Tamaki, as adorable as ever, sought approval at such a pivotal time. He couldn't fight the burning sensation in his face and ears or the growing strain in his trousers. He's barely done anything yet (Y/n)'s beauty and the odd sensations of his tentacles showering atop her skin propelled him to be better. Tamaki's tentacle could feel everything. From his understanding, (Y/n) had plush and soft skin that he wanted to scour more.

"It's... Different," the girl admits while glancing down upon herself. The oily slime from the tentacles sat atop her skin with this oddly ocean-like scent. Never had she ever imagined being pleased by tentacles of all things, "I kinda like it."

"Then... Let's try this," Tamaki mentally told his fingers to try something else. A coil of arousal tickled (Y/n)'s stomach at the thought of what Tamaki had planned. Tamaki's free hand finally joined in on the party. A coil of flesh ghosted over her stomach, another gliding over her ribcage. The bones beneath the skin of her ribcage were oddy ticklish and she giggled in delight. Finally, one tentacle was daring enough to go somewhere the others refused. It slithered from her ribcage, following the curve of her chest, to brush against a lone nipple. (Y/n)'s breath hitched to the new sensation, squirming a little on the spot. She's feeling good, Tamaki thought and changed his direction entirely. The tentacle coiled around (Y/n)'s breast, another followed the same protocol. The fleshy tips delicately coiling her perky sensitive buds and her breath hitched once more. The suction cups from each tentacle firmly hugged her skin and her breath grew heavier by the second.

(Y/n) squirmed under Tamaki's touch and dare she say she wanted more of it. "H-How come I'm the only one feeling good?" She whimpered and collapsed upon the nearby bed as her legs gave in.

Such a compromising position. Tamaki could only imagine what she'd look like completely naked. NO NO! Don't think about that now! (Y/n) wants to please me too? I'm actually happy enough touching her... "H-How would you make me feel good (Y/n)?" Tamaki quipped for a lack of knowledge.

"I-I can touch you too!" (Y/n) moaned out sweetly as her hold under the tentacles were pleasurable enough to make her come undone anytime now. Nevermind, she's so close, she wants Tamaki to claim her body as his. "T-Tamaki! Can you stick it in me?" The girl begged like a dog. Her chest rose and fell with each breath she took, quick and shallow.

Tamaki struggled to bring himself to undo his pants when his fingers were tentacles. All ten of them. I want to make (Y/n) happy! I can't let her down! Tamaki, now with a peaked interest and an objective in mind, allowed his tentacles to do the talking. His tentacles began taking possession over (Y/n)'s body one limb after the other. Two tentacles targeted (Y/n)'s skirt after long holding back from her precious core.

The tentacles wanted to rip the clothes clean off her body, Tamaki wanted to spare them. They fought with one another and soon gave into Tamaki's desires and settled on a compromise. The tentacles hiked up (Y/n)'s navy blue uniform skirt and disposed of her panties by shredding them. The same tentacles gave Tamaki a hand by unbuttoning his trousers and fishing his penis from the fly of his underwear. The boy found it odd how he's fully clothed while his girlfriend was nude spare for her skirt, but as long as she's happy he doesn't need to care about his own needs.

Tamaki treasured the sight of his woman without the urge to look away. He'd finally come to terms with sexual desire and might he admit it felt great. There's nothing to fear, no shame, and he's never been this comfortable with anyone in all his life.

A coil of flesh around the girl's waist, the tentacles drew (Y/n) to the edge of the bed. Tamaki approached his girlfriend meekly, his thin frame positioned before her lower end. The tentacles braced (Y/n)'s legs apart, the lips of her swelling pussy on full display. Her wet folds were glistening in her own love juices as it practically flowed out of her as they had a hunger for Tamaki's erect cock. The boy gave his tentacles a mental command to bring his girl further to him, his knees already pressed to the end of the bed. The vines guide (Y/n) onto Tamaki's cock effortlessly until it was sheathed within. So warm... So gooey... It's like she's hugging my... My... Oh just (Y/n) feels amazing, Tamaki's head was lulled backwards to sit upon his nape. Hot breaths brushed past his lips. The initial penetration was almost what did him under. No doubt he wasn't going to last long.

Actions speak louder than words. The tentacles followed Tamaki's inner desire and progressed to pull (Y/n) off of Tamaki's length almost to completion before pulling her back under. Something began tickling at (Y/n)'s clit to help edge her over in time with Tamaki. The couple was succumbing to the pleasure that racked their bodies. They moaned and twitched and came together. Tamaki emptied himself within (Y/n), her juices all over him. Tamaki didn't want to remove himself from her hot core as such an idea made his attitude damper. The tentacles slowly retracted back towards their owner, becoming human fingers once more.

The boy frowned at the sight of (Y/n)'s once flawless skin. Red circles littered her body, especially her neck and chest. Those damned tentacles. Painful, that's all Tamaki had to say. "You know..." Tamaki's voice was shaky as his throat burned from overuse. "I feel better than I have in... Forever."

"Didn't I... Didn't I... Tell you?" (Y/n) curled herself up within the covers of the bed. "Wanna make this into a weekly thing? Only if you're okay with it of course-"

"C-could we?" Tamaki's eyes lit up with delight. He thought she'd never ask.

"Anything for you."