A/N: Jean and Armin's first time.

"I'm finished showering," Armin said as he walked into Jean's bedroom; hair wet, towel around his shoulders, and donned in nothing more than one of Jean's button up shirts. He flushed, "And I… finished with that too."

That was some of the steps he had to take in preparation for tonight. Tonight being the first time they tried to… y'know… do it.

Armin had read probably a hundred online articles (and he always deleted his browser history right after) and even went so far to flip through health catalogues and anatomy books just to make sure he knew everything there was to possibly know about sex between two guys.

Tonight would be their second attempt, though the first time hardly counted because it had been in the heat of the moment and Jean had just tried to slid right in, and hadn't been able to even get the tip in – thank god he hadn't been using too much force, otherwise Armin would have been in for a world of hurt; or at least that's what all the facts seemed to state.

Jean was sitting on his bed, clad only in boxers, with his legs crossed and was fiddling with a box of condoms. When he looked up at Armin he gulped audibly, cheeks a deep red, before he was practically flinging the box of condoms at his wall – he hadn't expected Armin to walk in just when he did.

"O-oh… that's good," he said, trying to sound confident as he wiped the sweat accumulating on the palms of his hands onto his boxers.

The blond lingered in the doorway a little bit, knees trembling ever so slightly, before he made his way across the room and gingerly sat on the edge of the bed, "My hair is still a little wet. Is that okay?"

"Yeah," Jean nodded before patting the space next to him – an invitation for Armin to crawl over to him and settle with his legs tucked under him. The two leaned in for a kiss, a chaste touching of lips that lasted for a mere second, and Jean placed his hands on Armin's hips through the thin fabric of his shirt and Armin pulled back – jittery from his nerves.

"We should start," Armin whispered and Jean nodded again – scooting over some so Armin could lie back on the bed. He handed him a pillow, which Armin took gratefully before slipping it under his hips – propping himself up a bit.

Even though Jean had seen him naked hundreds of times, he was suddenly very bashful and it took all of his willpower to spread his legs and even though the shirt was long and fell down to his thighs, at this angle Jean could probably see everything and so Armin covered his private areas with his hands the best he could.

Typically, Jean would have grabbed his hand, made a teasing comment and then kissed the blond senseless but he was feeling a bit modest today too and so he just crawled on his knees over to Armin and sat directly in front of Armin's spread legs. He gave Armin his best reassuring smile, who returned it half-heartedly, before he was reaching for the small tube of lube he had bought at the supermarket last week (and the cashier had given him a wink and a thumbs up and Jean had just chuckled nervously before taking his purchases and walking bow-legged to his car, where he proceeded to sit for several minutes with his face on the steering wheel – horribly, horribly embarrassed).

Armin had explained to him how all this would be going down tonight and so he fumbled with the cap before squeezing way too much lube onto the tips of his fingers. He cursed – something that drew a forced laugh from Armin – before he was tossing the bottle aside and then grabbing Armin's left thigh and pushing his leg up and out a little bit more.

"You gotta move your hands. I need to see," Jean said, right hand dripping with lube and Armin hesitated briefly before he was lifting his hands and not knowing what to do with them, just holding them straight out into the air. And Jean might have laughed if he wasn't so distracted with the task at hand; he brought his pointer finger to Armin's hole and prodded the entrance a bit before putting the tip inside. He wiggled it a bit, glancing briefly at Armin, who (after taking several deep breaths and just relaxing) was propping himself up with his elbows so he could look at what Jean was doing – and since he looked okay, Jean pressed forward a bit more – up to the first knuckle.

"It feels weird," he commented and Armin scowled.

"That's mean." He said before adding, "It feels weird for me too."

"But it doesn't hurt?"

"Mm mm," Armin shook his head 'no' and Jean puffed out a breath of air he hadn't realized he was holding before twisting his finger as he pushed the digit in all the way, "It doesn't feel very deep," the blond said as Jean just kind of twisted his finger a bit – feeling around – it really did feel odd.

"Maybe you should try moving it in and out?" Armin offered tentatively, once it seemed like Jean wasn't going to do anything more than prod around.

"Right. Sorry," and then he was sliding the finger out, almost all the way, before sliding back in – staring intently as his finger disappeared inside Armin, before looking up at the boy who seemed to have calmed down a lot and was nowhere near as tense as he had been earlier.

Armin scrunched his nose up in confusion, "It feels…" and when he didn't answer, Jean tried slowly sliding back out, before sliding back in once, twice, and then three more times.

"I wouldn't say it is pleasurable, but it isn't bad?" Armin offered and when Jean frowned he quickly tacked on, "Don't get me wrong – I like it."

"That's good. I think I'll add the second one now," and once Armin nodded his consent; Jean pulled his finger back out – all the way this time – before placing two at Armin's entrance and wiggling the tips of his fingers inside. There was a bit more resistance with this one, but it still went in fairly well and Jean worked his fingers back and forth inside Armin who was beginning to pant.

"I actually… I actually like it more than I thought I would," he confessed and Jean had to bite his cheek to avoid the smug grin that almost slipped on his face.

"Awesome. I'm gonna spread my fingers now," Jean said and Armin nodded, eyes sliding shut as Jean opened and closed his two fingers in a scissoring motion, "… I liked it better when you weren't doing that."

Jean chuckled, "This – it's actually harder to do this than I thought. It's a great finger work out—owch!" Jean glared at Armin who was scowling at him even though he was the one that had smacked Jean upside the head.

"Don't say something like that – its indecent and rude."

Jean just shrugged, going back to stretching Armin, who after several moments told Jean, "Do it in the other direction as well – so it's stretched properly."

Finally, moments later, "Can I put in the third one?" he asked as he slid his fingers out, before pressing three inside. Again, nothing too challenging – this was actually going pretty good. Better than expected – he didn't feel nervous at all anymore. If anything, staring down at Armin sprawled out on his bed in nothing but a loose shirt, legs spread, and cheeks flushed – was kind of hot and Jean let go of Armin's thigh briefly so he could unzip his pants and relieve some of the pressure in his pants, before grabbing the boy's leg again.

Armin was actually feeling fairly confident himself, though he knew the next step would be a big jump from a few fingers, and tried not to let his hopes get up too much.

"I think I like it best when you don't move your fingers – just the feel of you inside me is making me pretty excited,"

Jean jerked a bit – the action causing Armin to look up at him, he had felt it after all – the blond's words making his cock twitch in excitement, "I have to move though – otherwise it isn't sex."

The brunet watched as Armin pulled the shirt up a bit, before wrapping slender fingers around his half erect member.

"I thought you said you were excited," Jean said – worried that maybe Armin had lied about liking it.

"I said its 'making' me excited. It's fine now though," and gone was the modesty from earlier (because now his nerves didn't seem to be on fire) and he moved his hand up and down the length of his cock – showing Jean just how 'excited' he was.

Jean swallowed, "I think you're ready," before he was pulling out his fingers and grabbing the box of condoms from earlier and taking one out before removing it from its wrapper and smoothing it down his cock with practiced ease (literally practiced, because back when he and Armin first started dating he must have went through an entire box of condoms trying to use them efficiently so Armin wouldn't think he was a loser) before reaching for the tube of lubricant from earlier and squeezing some out onto himself and hissing, "Fuck that's cold."

"I know," Armin gave him a dead-pan look, as (for added security even though the condom was lubricated) Jean spread the lube all over himself.

"You ready?" he asked, and he slid forward so he was closer to Armin – pressing Armin's leg up even more, his lower half lifting off the bed some. He placed the tip of his erection against Armin, "It's okay right?"

And Armin nodded, taking deep breaths once more because he could feel his confidence slipping away, "Yeah – I'm good."

And then Jean was moving forward and, "… It's not going in."

"You have to use some pressure. You can't just expect it to go in that easily."

"My fingers did,"

"Yeah well your fingers are a lot smaller than your – your thing,"

Jean raised an eyebrow, "My thing?"

Armin flushed, "Shut up - just get on with it."

The brunet nodded, before pressing forward once more and fuuuck it was really tight and, "Relax Armin," he grunted when Armin tightened around the head of his erection.

"I'm sorry," Armin apologized, sucking in deep breaths through his teeth and when he had unclamped himself around Jean, the brunet started moving forward once more – achingly slow. Achingly because he wanted to just thrust forward because it was so hot and tight, and achingly for Armin because holy hell it hurt like a bitch and, "I think I'm going to die."

"You aren't going to die," was Jean's response, grinding his teeth a bit as he kept pressing forward.

"No really," Armin gasped, hand wrapping around Jean's wrist, "I'm dying. Stop."

And with more will power than Jean thought he had, he stilled his hips – panting above Armin – only half way in; and then he was looking at Armin, whose cock was lying limp against his stomach and had tears running down his face.

"Fuck. Armin are you okay?" there was panic evident in his voice – was it supposed to reduce his boyfriend to tears? Maybe he did it wrong? Shit.

"Oh god. Armin I'm sorry. Shit, should I pull out? I'm taking it out," and he started to pull back only for Armin to tighten his grasp around his wrist.

"I swear to god Jean if you move, I will kill you."

Well damn. Who knew Armin could be so frightening.

"What… What do I do?"

"Just, just let me catch my breath," and honestly Armin felt like quitting right here and now but they'd already gotten so far and he knew if he stopped Jean probably wouldn't want to try it again for months and even though it really hurt, he wanted to do this.

"Okay," Armin gasped after what felt like hours, Jean trembling above him because he really, really needed to move because it was unbearably good inside Armin, "Maybe try rocking your hips a little? Like maybe you could shimmy out a little and then like… wiggle back in?"

Jean didn't think he had ever heard Armin say the word 'wiggle' before. Typically he was all about using more scientific terms, and he was tempted to tease him (he liked teasing Armin – he really did) but decided against it and instead moved back a little bit, all the while watching Armin's facial expressions; who didn't seem to mind the movement much at all, before 'wiggling' forward and cue the small gasp from Armin. He repeated the process, left hand rubbing soothing circles on Armin's thigh, and right hand rubbing up and down Armin's side – murmuring whispered apologies and promises that it would be okay.

When he was finally in, they both let out a relieved sigh – Jean because damn did it feel good, and Armin because good lord he had finally stopped moving.

The blond breathed harshly through his nose, biting his lip as he allowed himself to relax – a feat in and of itself – and just adjust to, he hated to admit, the intrusion.

Jean took it upon himself to start stroking Armin's cock, offering a bit of a distraction from the throbbing ache inside of him, and coaxing the appendage back to life. After a couple short strokes – Jean knew exactly how he liked it – he was eliciting gasps of pleasure from the blond.

"Okay, I'm gonna move now."

And Armin whimpered, "Slowly please. And shallow too! Don't pull out all the way! Start with like a quarter and then work your way up from there."

"I will," Jean placed a soft kiss atop Armin's nose, before pulling back – not too much – and then rocking forward – letting out a grunt of his own.

"Fuck," he cursed, "It feels so good." And Armin grit his teeth because it didn't feel so good on his end, but he wasn't telling Jean that.

Jean pulled out more, this time half way, before he was sliding forward once more – as slowly as he could manage without torturing himself, "So good," he rasped and Armin had to bite his wrist.

He liked it more when Jean just stayed still, but he knew he couldn't just ask Jean to not move. The moving forward part wasn't too bad, but he didn't care too much for the pulling sensation he experienced every time Jean slid out.

Armin brought his unoccupied hand to his cock, stroking himself once more and he supposed it wasn't too bad if he distracted himself. It wasn't good though either. But Jean seemed to be enjoying it, and so he'd just have to grin and bear it – it would feel better in a little while – or at least he kept telling himself that.

"Armin," Jean groaned, thrusting in and out of Armin slowly, "Can I go faster?"

The blond didn't answer for a moment, thinking it over. It was no longer that crippling, sharp stinging sensation but rather a dull throb and a slight burning and so he thought maybe he could handle it, but…

"Remember what I said about the prostate gland?" he asked tentatively and Jean looked confused for a moment - likely wondering why Armin would ask him an anatomy question in the middle of sex – before he remembered just how important of a role the prostate played; he nodded 'yes'.

"Could you… could you find it first please?" Armin asked, still teary eyed and Jean's own eyes softened before he was moving Armin's wrist away from his mouth and kissing him.

"Yeah, okay."

And now Jean was hesitating, "Uhh…" now how did he ask this without sounding like a complete idiot, "Where is it? How do I find it exactly? I mean… I can't feel around with my dick. It doesn't swivel."

Armin wasn't sure if he should laugh or cry, "It's the angle of your thrust. The shape and size of your penis affects what angle you need to use. So it'll be trial and error."

"Right." And so Jean pulled back, no too much – he was on a mission for Armin after all – and then thrust forward in a downward motion. Judging by Armin's hiss, that wasn't right.

"No, ah. Let me help," and with aching hips, he arched his back a bit, "Hey give me a another pillow," which Jean blindly reached for, trying not to jerk out of Armin as he reached behind him.

"Here," he stuffed said pillow under Armin, "Should I let go of your leg?"

Armin thought about it for a moment, before shaking his head 'no', "I'm going to put my other leg around your waist," and then he was raising his leg – the appendage trembling – before he was hooking it around Jean's waist.

"I feel like we're playing twister," Jean commented softly and Armin smiled, "Only you would think something like that."

"Okay," Armin said, settling into his pillow a bit, "Try again, but pull out more this time. And thrust upwards."

Jean nodded eagerly, before he was pulling out more than half-way and trusting forward once more, "Good yet?"

"Not yet – but I think I'm getting used to you moving," it still didn't feel good though, but it was no longer unbearably painful. For Jean, he could put up with it. And Armin thought maybe that was half the battle – he needed to stop telling himself it hurt and try to focus on the good things. The way Jean smiled at him, the way he grunted with every thrust, the way sweat dribbled down the side of his face. Jean looked really good and seemed to be enjoying himself, so Armin would do his best to enjoy this as well.

Jean pulled back once more, this time angling his hips a bit differently and then swiftly thrust forward once more – the action causing Armin to cry out and his whole body to tremble.

"Fuck, did I hurt you?!" he practically screamed and Armin shook his head in a circular motion – yes? No? Jean couldn't tell.

Armin had to catch his breath before answering, "Yes, no uhm… I'm not sure. It was different from before and I can't… I think I'm too sensitive."

"Should I try it again?"

"Uhm… yeah, but maybe a bit more gently and not exactly right against it? I think maybe you jabbed the prostate and I've always been a bit sensitive so maybe if you could… Actually could you get my anatomy book from my bag?"

Jean squeaked, "What? No. Come on Armin, let me try again – I'll be more careful."

And Armin figured, if Jean had to pull out all the way, he probably wouldn't want Jean to enter a second time and so he reluctantly relented, "Okay."

The taller boy sighed in relief, before pulling back out once more and this time thrusting gently and at a slightly different angle and, "Ah!" Armin's leg tightened around his hip.

It was probably the single most arousing sound Armin had ever made and Jean suddenly wanted to hear it again, and so he pulled back once more – going for the same angle and again Armin was crying out.

Oh god he could get used to that, "Is it good?"

And Armin nodded his head, mouth agape – which Jean took as a signal to do it again.

"Don't – please not too much," Armin cried, bringing his wrist to his mouth again so he could bite it. Armin couldn't explain it – it was good, but almost torturously good. He still had that ache every time Jean moved and there was that burning tugging sensation every time he pulled out, but now there was the added addition of Jean rubbing against him in a way that was… he couldn't explain it. But it was too much, "I'm too sensitive."

"Should I not do it anymore?" Jean asked, shallowly thrusting against Armin because like hell he was going to stop now – not when Armin had moaned like that and god the way he had tightened around him every time Jean rubbed him in the right way – if he had thought Armin was tight before – it was even crazier when the blond was enjoying it.

"No, just… every once in a while?"

Jean nodded, before he was thrusting again – this time not sliding against Armin's prostate and instead downwards more. And now that Jean had free reign and didn't have to stop every thirty seconds because he was hurting Armin - and yeah Armin felt good, but he couldn't exactly get off if he knew he was hurting the boy – Jean lost himself. He was pulling out as far as he dared and sliding forward as fast as he could and it was good – really, really, really good and at first he tried to remember to rub against Armin's prostate but sometimes he got the angle wrong and sometimes he didn't and sometimes Armin would cry out in the way he had when Jean had accidentally jabbed Armin's prostate the first time and pretty soon his ears were ringing and he wasn't sure how much longer he'd last.

Armin seemed to be getting used to it if his facial expression were anything to go by and Jean took comfort in that and before he knew it he was cumming and it had to have been the single most amazing orgasm he had ever experienced and his whole body shook and he pulled out of Armin shakily before pulling off the condom, tying it, and tossing it in the trash bin by his bed. And then completely spent of energy, he plopped onto his back (after having let go of Armin's leg and unhooking the other one from around his waist) and just trembled from how good he felt.

He turned his head to look at Armin who was lazily batting at the pillows beneath him – uncomfortable but too tired to move them. So Jean pulled them out from under him and tossed them to the top of the bed. He smiled at the boy, eyes soaking up his flushed face, damp hair, the way Jean's white button up clung to his heaving chest, and – Jean's eyes narrowed in on Armin's half erect member and seeing no stain anywhere on Armin's thighs or on the shirt, "You didn't cum?"

"Ah… no." and the blond sounded a bit guilty and Jean suddenly felt bad.

"Was it that bad?" because he had thought it was the best thing in the world and now he kind of felt like crap.

"No, it wasn't bad." Armin whispered.

"But it wasn't good either?"

The blond hesitated, before rolling over to face Jean, "All the things I read said it isn't uncommon for a guy to not enjoy his first time being penetrated."

"But I thought – I found your prostate – isn't that supposed to like make it amazing or whatever?"

"Well… I guess so. And it was, but I just don't think I was used to the whole thrusting business. You didn't hurt me or anything…" Jean frowned and Armin corrected himself, "Well it did hurt but it wasn't your fault."

"It started feeling okay towards the end there," Armin said, snuggling against Jean's chest tiredly, "… I think if you had lasted more than a minute I might have had a chance to enjoy my… self…" the blond trailed off as Jean stiffened against him and looked up at him and noticed the horrified look on his boyfriend's face.

"A minute?" he asked, "A minute?" because it had felt like a lifetime to him and seriously a minute? That was so embarrassing.

"Well I mean if you count all the time it took for you to get inside and let me adjust and for you to locate my prostate and what not; it was actually a very long time. But we had to keep stopping and going and so when we finally did it without any interruptions you were pretty much done within a minute."

"Nooo," Jean groaned, burying his face into his hands.

"Well we should probably count it from the start because it felt good the whole time for you right? So really you lasted a really long time!"

And Jean felt worse now because here Armin was trying to stroke his ego when the blond himself hadn't even been close to cumming.

"Ugh, this is the worst," he cried and Armin rubbed his shoulder.

"You'll do better next time – we both will."

Jean spread his fingers a bit to peek at Armin through his hands, "Next time?"

The blond nodded.

"Even though it wasn't very good and you didn't cum?"

Armin nodded again.

"You don't hurt right now?"

Armin shook his head, "Not really. I feel a little weird – empty maybe? But I'm not as sore as I thought I'd be."

Jean smiled, looking relieved, "Good, I'm glad."

Jean was startled awake the next morning by a pillow harshly thwacking him in the face – was it possible for a pillow to hurt that much? He groggily blinked up at Armin, who was sitting up and glaring at him.

"Never again," the blond hissed and Jean sputtered in shock before sitting up as well.

"But I thought you said it didn't hurt—"

"Well I hurt now!" Armin cut him off, "My hips and my back and everything hurts – I think I'm dying."

"Armin you aren't dying, you're just a little sore from last night."

"A little?" Armin asked incredulously before he was groaning in his hands – too tired to argue, "If you ever want to have sex with me again…" he shook his head, "Just… Please bring me some pain medicine and a heating pad if you have one."

Jean smiled tenderly at Armin, even when he was apparently dying from pain, he still didn't have the heart to be mean. He leaned over to kiss the blond gently, before ruffling his hair and rolling out of bed.

"I'm miserable," Armin whined and Jean figured he really must hurt because typically the blond tried not to inconvenience anyone when he wasn't feeling well.

"Sorry," Jean apologized, "I'll make you breakfast in bed. What do you want?"

"… French toast?"

And Jean smiled, "That's my specialty."