A/N: Leonardo's a tricky one, but she has some undeniable charm to her.

Do enjoy~


Ritsuka hadn't expected to be summoned by Leonardo de Vinci. Much less to her personal quarters.

Still, despite how enigmatic and odd the brunette could be he didn't see anything inherently suspicious about it and decided to go along with it – thus, the black-haired Master found himself walking down the long halls of the dormitory wing of Chaldea, pointedly avoiding crossing paths with the more yandere Servants lest they cling to his arm and perhaps try and interrupt his mystery meeting with Leonardo.

Mercifully no such yandere appeared, and Ritsuka made it to Leonardo's door unmolested. Banging his knuckles upon the firm wood he waited, idly pondering what was so important that Leonardo invited him to her room, rather than just the control room. A secret mission? A conspiracy at Chaldea she didn't want to share with anyone else? Planning for a surprise birthday party? The possibilities were endless, not least because Leonardo was behind it.

Ritsuka was snapped from his musings however as the door clicked open, bringing a reflexive smile to his face. ''You called?''

''That I did.'' The familiar voice of Leonardo responded; the mature woman smiling at him as she peeked out from around the corner. ''Come in, come in~''

Ritsuka didn't protest, a touch curious as she pulled the door opened and wandering inside. Her room was about as grand as he expected, sizeable both lengthways and in height. A grand bed was present at the far end of the room and numerous tables and drawers were present, various trinkets dotted about them. Compared to some other Servants though her room was rather tame. At least she didn't have countless portraits of herself like Nero.

Smiling amusedly at the thought Ritsuka shook his head, dispelling the thought as Leonardo shut the door behind him, tempting his gaze over to her. ''So what was it you wanted to speak with me about?''

''Well, it's a bit embarrassing.'' Leonardo chuckled sheepishly, brushing some dark brown hair from her face. ''I need your help with something. I didn't want to ask one of the other male Servants, and we're quite close...''

Ritsuka blinked in confusion. ''And that would be...?''

''Could you help me get used to this new body?'' Leonardo gestured at herself. ''I was a man before being summoned as a Servant, and while I've acclimated to this form, there's one sort of act I haven't partaken in...''

Ritsuka's lips moved, about to ask what she meant by that... right up until she lifted her skirt a tiny bit. Not enough to show any, but enough to get the implication across – she wanted to have sex with him. The idea made Ritsuka's jaw drop, disbelief on his face and earning a sheepish smile from the brunette Servant, one finger scratching her cheek.

''Aha, yeah, I knew you'd react like that.'' Leonardo said wryly. ''I understand if you're not up for it, though I'd appreciate it if you were. It'd mean a lot.''

At that Ritsuka blushed and looked aside, unable to look at Leonardo's surprisingly-pretty sheepish expression. He stewed in silence, mulling it over in his mind – part of him wanting to reject the idea outright... but part of him was tempted too. Though she might've been a man in the past life, Leonardo was effectively a woman now, and a very attractive one at that. He didn't have much experience but he doubted she did either, so that assuaged any concerns about making a fool of himself too. Really, at this point, it was just embarrassment holding him back.

Thus with a slow, purposeful inhale and exhale Ritsuka cleared his mind – before finally making his decision. ''Alright. Let's do it.''

Leonardo's expression brightened, her cheeks colouring pink as well. ''Thank you! Just wait on the bed for a moment, I'll go get changed into something a bit more... romantic~''

The slight teasing undertone burnt his cheeks, but with an embarrassed mumble Ritsuka obliged and walked over to her large double bed, sitting himself down on the edge. Leonardo smiled at that and hurried off into the bathroom at the far end of the room, the door clicking shut behind her – leaving him sat in silence for a long few minutes. If he listened closely he could hear the sound of clothes being unzipped, the idea darkening his cheeks and enticing Ritsuka to slowly start undressing too; taking his tie off and slipping his belt off of his waist, keeping his pants buttoned for the time being.

He was distracted though as the bathroom door opened, tempting his gaze over – and his breath caught his throat as he laid eyes on Leonardo. Gone was her fancy uniform and in its place was just a pair dark blue underwear with constellation patterns upon it. The bra pushed up her plump chest and her panties hugged her waist nicely, his gaze unconsciously roaming over her smooth thighs and flat stomach, wandering then up her cleavage and to her face, noticing the healthy blush on her face. With surprising demureness she tugged on a white button-up shirt, keeping it open and only loosely hanging from her shoulders, giving her some vague amount of modesty.

''So... like it?'' Leonardo asked sheepishly, approaching the bed. ''Thought I might as well wear something sexy.''

''Y-Yeah.'' Ritsuka coughed, looking off to the side. ''Looks great.''

Leonardo smiled at that and eased herself down onto the bed next to him, cupping his cheeks and tilting his head to face her. Ritsuka stared deeply into her eyes, losing himself in them for a brief moment before his gaze wandered south, unable to not look at her cleavage. Leonardo didn't seem to mind and even teased him about it; hooking her index finger into one of the cups and pulling it out, giving him a better look at her boob before she shifted the cup back into place.

A thumb across his lips lured his gaze back up though as Leonardo leaned in, his eyes shutting – and then at last they kissed. It was a bit awkward, both clearly not used to it and drawing back after a few moments... but without a word said they both leaned in and kissed once more. It was easier the second time around, enticing them to drag it out with a mutual hum. The hand caressing his cheek slid down to his left shoulder, enticing Ritsuka to touch her side with his right hand, sliding his fingertips along her taut stomach.

''Mm...'' Leonardo breathed as she drew back from the kiss. ''I'll let you be on top, alright?''

Ritsuka blushed and murmured an agreement, earning a smile from the brunette woman. Without a word she eased herself down onto her back, tempting Ritsuka to get on top of her, gazing down into her warm eyes. She slipped her hand down and grasped his wrist, guiding his hand down her stomach and soon into her panties – darkening Ritsuka's cheeks. He didn't resist her hold however, letting Leonardo lay her fingers over the back of his own and guide him, making him rub her slit.

''Mm... just like that...'' Leonardo breathed, shivering.

Ritsuka obeyed, face hot as he rubbed her off. His movements were slow and curious, having never done anything like that, but Leonardo was nothing if not patient – soft hums and groans starting to escape her. They rose in volume as he pushed two fingers into her, his digits sliding between her lips and into her inner heat with barely any resistance, her walls clamping down on them. The oppressive heat felt novel in a way that only excited him, encouraging the black-haired master to pump his fingers in-and-out of her.

Leonardo lured him down into a kiss at the same time, their lips mashing together with growing confidence. Daringly sliding his hand under her bare back Ritsuka held her close, deepening the kiss and working his fingers with growing excitement, thrusting them about her hot insides and fingering a moan out of Leonardo, her walls clamping around his fingers tightly. Craving more though Ritsuka broke off the kiss and leaned down; boldly burying his face into her cleavage.

''Ah~'' Leonardo moaned, a shiver travelling through her slender frame.

Ritsuka relished the erotic sound; keeping his face in her chest as he daringly pushed a third finger inside her pussy – the fullness coaxing another sweet moan out of Leonardo. He committed the sound to memory, feeling her breasts push against his face with every exhaled breath and enticing him to kiss the top of her tits, lightly motor-boating them but too shy to really commit to it. From so close though he could nearly hear her heartbeat, the quick thumps arousing in a way he couldn't describe.

He was distracted however as Leonardo gently tugged his hand back, speaking just after. ''Let's skip to the fun part now, eh?''

Ritsuka blushed at the suggestion, but after a second found himself nodding, shifting back. Squirming further back herself Leonardo lifted her long legs up and peeled her dark blue panties up them, his eyes glued to them as they slid up her ankles and off her feet; her legs slowly spreading open. His gaze went between her legs at that, heat creeping across his face until he looked akin to a tomato, his pants suddenly feeling ever so tight.

''Come on, take your clothes off too.'' Leonardo sheepishly said. ''It's embarrassing when I'm the only one naked. Nearly, anyway.''

Ritsuka blushed at that and murmured an agreement, sliding both hands down to his waist and undoing his pants. They ended around his ankles in seconds, his boxers soon following before both found themselves kicked to the floor alongside his shoes, leaving him clad only in his top. A top that soon found itself unbuttoned and slipped off of his shoulders, leaving him naked before Leonardo, her gaze running over his bare body with an approving hum.

Pushing down his embarrassment Ritsuka shifted between her legs, awkwardly fumbling for a moment until he planted his hands on either side of her, his right going down and grasping his cock, lining him up with her entrance. The tip slid along her lower lips, the slight friction coaxing a mutual shudder out of them; excitement throbbing down his cock and a soft moan lifting off of Leonardo's tongue.

''Put it in...'' She breathed sensually.

Ritsuka did; a slow roll of his hips pushing him inside. Wet, searing heat clamped down on him almost instantly, coaxing a stilted gasp from Ritsuka's lips – pure pleasure surging down his cock and encouraging him to sink even deeper into Leonardo. The curvaceous woman moaned at that, her slender hands gripping the sheets and gripping them tight, enduring the slight discomfort that came with him entering her – reaching deeper than her own fingers ever could, and deeper than any dildo she'd used thus far.

''Ahh...'' Leonardo slowly relaxed as he bottomed out inside her, his cock throbbing against her walls. ''Wow, that's a... bit of a strange feeling, but it's not an unpleasant one. What about you?''

''Yeah.'' Ritsuka grunted out, shuddering as he felt her walls practically massage his cock; gripping and squeezing with the slightest tensing of muscle. ''Mn, you're tight...''

''I'll take that as a compliment.'' Leonardo wryly said, biting her bottom lip as she felt him start to pull out. ''You can move now...''

Ritsuka jerked his head in a nod and planted his free hand on her thigh, steadying her as he slid his shaft out of her hot vice – and with a tight groan he sheathed himself straight back inside her, filling her womanhood back up to the brim. The single thrust coaxed a synchronised moan out of them, the sound filling the bedroom as he kept pumping into her, gradually finding a slow but firm rhythm that hilted him inside Leonardo.

As he got used to the movement Ritsuka became more confident; leaning over Leonardo more on both arms and thrusting his waist forth faster, fucking a surprised moan out of Leonardo – one he swiftly silenced with a kiss. The brunette held onto him in return, one hand clutching at the back of his head whilst her other roamed over his bare back, moaning hotly into his mouth as he went balls-deep in her, their mutual inexperience only making the act feel so much better.

''Mmph- ahh... Fujimaru-kun...'' Leonardo moaned, her lips leaving his long enough for them to catch a breath. ''That's it... keep moving like that...''

Ritsuka shuddered at her breathy, wanting tone – her needy voice burning itself into his mind. Desiring to hear even more sounds from the Servant Ritsuka sped up, his thrusts short and hurried and plunging himself between her lips, his pelvis clapping against her own with repeated fleshy smacks, the bed beneath them rocking from the force of the movement. Sharper, more womanly moans arose from Leonardo's throat, her inner walls clamping tightly around his girth as he filled her with it.

However Ritsuka's inexperience showed through in his stamina. Just being inside Leonardo, her vaginal walls clamping around him, felt far better than any amount of private getting-off could – hastening his end and hurrying his thrusts. His flesh smacked against hers and he pounded her like she was the last woman on the planet, railing her raw.

''C-Crap, Leo...'' He gasped out. ''Gonna cum...''

The Servant moaned, laying her hand on his stomach. ''P-Pull out then...''

Ritsuka didn't want to, but with a forceful groan he made his hips stop and pull back, letting his cock slide out of her drooling-wet sex. Compared to her pussy the air felt so cold, his gaze drawn down to her quivering folds, the urge to just stick it back in and ram her until he came ever so tempting – the only thing holding his lust back being he didn't want to upset her.

Leonardo was more than willing to entertain him in other ways though; sitting upright and rolling them over, leaving her straddling his lap. Cupping his cheeks the busty woman drew him into a deep kiss, her tongue prodding at his lips and enticing him to part them, groaning as she shoved his tongue into his mouth and explored. He fought back with his own tongue, their wet appendages wrestling with awkward, fumbling pushes and wiggles, neither quite sure if that was how to do it but aroused all the same.

''Mm- ahh...'' Leonardo exhaled as she pulled back. ''Here, let me...''

Reaching behind her back Leonardo hurriedly unclipped her bra, face flushed as she shrugged it off her shoulders and threw it to the side – a slight smile twitching across her lips as she cupped her breasts and pushed them together, as if offering herself to him. It took Ritsuka a moment to realise that was exactly what she was doing, enticing both of his hands up her stomach and cupping her tits from below. They fitted nicely into his hands, enticing him to grope the brunette and get a feel for her chest.

Smiling slightly Leonardo leaned down, their lips meeting in a kiss that both rapidly deepened, utterly melting into each other – her hands loosely wrapping around his shoulders and sitting comfortably on his lap, his cock pressed up against her pelvis. For what felt like a small eternity though all they did was kiss and grope, fingers never straying down to his cock and giving him time to calm down, the urge to cum waning, if only for a time.

''Mm...'' Leonardo pulled back from another kiss. ''You calm now?''

''Yes.'' He gave her a kiss to punctuate that, earning a light blush from the Servant. ''Can we keep going?''

''That we can~'' Leonardo responded with a slight, coy lilt. ''I'll top now~''

Emphasising that Leonardo lifted herself only enough to get his cock under her, the tip sliding along her lips – and with a relieved moan she impaled herself back down onto him. Ritsuka gritted his teeth and let out a stilted moan of his own, his hands landing on her hips and pulling her down until he was sheathed all the way inside her. With how aroused both of them were Leonardo didn't waste time taking it slow; her hips starting to rock almost right off the bat and stirring him around her slick insides.

Slender hands on his shoulders pushed him flat onto his back, a grunt escaping Ritsuka's lips and his eyes landing on Leonardo's flushed face as the brunette leaned over him – flashing him a coy smile as she kept riding him. The slight, playful glint in her eyes ignited something within him, enticing Ritsuka to buck his hips up and slam into her, fucking a moan out of Leonardo.

''Leo...'' The black-haired master breathed and moved his hands down her thighs, his touch aimless but simply admiring her smooth legs.

The Servant responded by leaning back slightly, a moan rolling off her tongue as she impaled herself onto his swollen cock. The angle let him get a good view of his dick disappearing inside her, the way her inner walls clamped around his cock never failing to make Ritsuka moan and thrust himself up into her – the two of them working together and smacking their flesh together in a ceaseless, increasingly-hurried cycle, heat climbing up his cock once more. Their brief break had delayed his orgasm for only a short time, and as he felt her quivering walls press down on his dick he found it increasingly hard to hold back.

Still he endured, gripping her thighs and slamming his hips up into her wet pussy, the resounding claps of flesh joined by throaty moans from the Servant herself - her insides tightly clamping his shaft as he filled her. Shudders travelled through her as they did him, their movements growing faster and jerkier as they succumbed to the mounting heat in their joined parts.

''Ah, yes, a-almost...!'' Leonardo gasped out, her hands clenching into fists. ''M-Mast- ah~!''

Slick flesh seized around his cock, a cry pierced the air – and in an instant Ritsuka saw white as he climaxed inside Leonardo. Throbbing pulses of pleasure shocked up his cock before he unloaded ropes of milky heat into her, squeezed out by the slick walls that pressed down on his shaft and making a total mess inside of the Servant's pussy. With gasping moans Leonardo kept working her hips, tightly squeezing him as she flexed her hips and squeezing ropes of heat up his shaft and into her womb.

''Ah, hah...! Haah...'' Her hips quaked before soon jerking to a stop – an explosive moan tumbling out of Leonardo's lips. ''Mm... it feels... so hot, inside of me...''

Ritsuka moaned dumbly in response, blinking away the spots in his eyes and dimly stroking her thighs. It took him a solid minute to come down from his orgasmic high, finally snapped out of it when Leonardo lifted her hips up and let his cock slide out of her with a dazed moan of her own, her slim hand covering her sex to stop his seed from leaking out.

''Wow...'' Leonardo breathed, sitting down on the bed next to him. ''Feels different than I was expecting, but I can say I don't like it, heh~''

Ritsuka just cracked a breathless smile and hummed, too busy catching his breath to say much else. Leonardo however was far from finished with him – something he realised as the buxom brunette flashed him a coy smirk and shuffled over the bed until she was flat on top of his legs. The reason why became apparent as Leonardo sensually curled her fingers around his semi-erect cock, pulling it to her lips and kissing it a wet kiss to the tip, easily coaxing a gaps out of him.

With a cheeky giggle Leonardo responded by kissing it again; her lips grazing over the head of his cock and kissing it more. Just feeling her lips press against his cock and smooch felt downright heavenly, his post-orgasm sensitivity only enhancing that; eliciting a string of stilted moans from his throat as the Servant teased him. The brunette took it further; her kisses soon interspersed with quick licks and cleaning his cock of their mixed fluids.

''Mn... Leo...'' Ritsuka moaned out, shuddering in bliss.

''Just lay there Master.'' Leonardo breathed, smooching the tip again. ''I want to please you this time~''

Any complaints he had instantly melted into a throaty moan as Leonardo followed up by taking his cock into her mouth; sucking on the tip of his dick. The wet heat that sucked on it, her lips sliding up to the very tip before she pushed her head down again, felt so good he couldn't resist the urge to lift his hips up off the bed and push his cock deeper into her mouth – enticing Leonardo to glide her lips further down his cock, grazing his girth until she had two-thirds of his cock on her tongue and prompting slurping back up to the head.

Squeezing the back of his cock in her hand Leonardo repeated the movement – finding her rhythm as she bobbed her head up-and-down his length, seductively slurping his cock and coaxing no small number of moans out of Ritsuka. He gripped onto the sheets but couldn't hope to hold back his voice, sounds tumbling off of his tongue as Leonardo's own tongue pressed itself flush against the underside, searing his shaft with her slippery appendage.

''Mmph, smch, smch~'' Leonardo attentively sucked him off, tucking some hair out of her face so it didn't get in the way.

Biting his lip Ritsuka laid his hand on the back of her head and pushed her down – instantly moaning when she obeyed, uncurling her fingers and deep-throating his dick with startling ease. He could feel her throat muscles clench around the tip of his cock like a ring of flesh, pressing down on it and sending jolts of warmth straight up his cock, a distinct urge mounting within his length. The Servant remained there for only a few moments though before she went back to bobbing her head and seductively slurping his shaft, the wet noises her mouth made driving him wild.

Doubly so when Leonardo got her knees under herself and stuck her ass in the air; seductively swaying it side-to-side as she blew him. His lustful gaze glued itself to her rear before sliding down her back all the way to her face, watching her pink lips snugly purse around his cock and slide along it, leaving it sticky and slick with her spit. Coupled with the tongue that lashed at the tip or pressed itself against the underside of his girth it felt downright heavenly, pleasure surging up his length and forcing a moan out of his throat.


Until with a tight moan Ritsuka blew his load; thick spurts of cum filling her mouth. Leonardo shut her eyes and sucked up to the tip, keeping it in her mouth whilst she jerked off his shaft with her right hand, coaxing spurt after spurt onto her tongue and audibly swallowing his cum without protest. A slower, stilted moan tumbled out of Ritsuka's lips as he gradually came down from his high, blinking away the spots in his vision and shuddering as he relaxed.

''Ahh...'' Easing himself back he relaxed into the sweaty sheets. ''That felt... good...''

''Heh, glad to hear that~'' Leonardo cheerily said, sitting on the bed next to him – wiping her mouth dry with the back of her hand. ''I think I'm really getting the hang of this new body too, so thanks for that.''

''It's fine.'' Ritsuka waved a hand half-heartedly, too out-of-breath to muster more than that.

''Hehe. Also...''

Leonardo leaned forwards slightly, a coy smile curling at her lips as she slid an arm under her breasts, emphasising their size.

''If you wanna do this again and help me get acclimated... heh, you know where to find me~''

Ritsuka just blushed and mumbled something incoherent.

But when he arrived at her personal quarters a few days later to 'check up on her', neither could say they were surprised.