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After hours training

Summary:

you ask Leon for sex advice before a date with another coworker, only expecting him to talk you through your nerves. when the conversation turns into something far more hands-on, both of you realize the problem was never really about another man. Maybe you trusted Leon for a reason and maybe he wanted you long before either of you knew what to call it.

Notes:

This is an older request by an anon on Tumblr that has been sitting in my inbox for a while, so thank you so much for your patience. I’m slowly making my way through requests one by one, even if it takes me some time, and I really appreciate everyone who waits for them. I hope this was worth the wait ♡

Work Text:

You and Leon had been working together for some time now.

At the beginning, he had intimidated you. Not because he was rude or cold, but because Leon Kennedy had the type of presence that made anyone feel tense. He was older than you, more experienced, and annoyingly calm in situations were anyone else would have been losing their mind.

Over time, things became easier. You got used to his tired jokes, to the way he leaned against your desk when he wanted to hear gossip but pretended he didn’t, to the quiet way he checked if you were okay after rough missions. He got used to you too, even if he acted like you tested his patience for a living.

You were not best friends in a childish way. You did not tell him every thought that crossed your mind, and he was not the type to overshare either. But he had become one of the few people you felt comfortable around without needing to perform.

That was probably why you ended up at his apartment more often than you planned.

He lived close to the office and you usually ordered takeout. His couch was comfortable enough that there were times you had fallen asleep on it while some terrible movie played in the background. Leon always complained about your film choices, you always told him his taste was depressing, and somehow that had become part of the routine.

You had noticed he was attractive, obviously. You were not blind. There were days when he came back from training with damp hair and a tight shirt that hinted at the defined muscles underneath and you had to make a conscious effort to look normal. But noticing was not the same as doing anything about it, and you had never allowed yourself to take the thought too seriously. Leon was Leon: older, complicated, your coworker and a friend in a way neither of you had ever bothered to define.

Besides, lately there had been Carlos.

Carlos worked in Intelligence, and he had been flirting with you for weeks. He was handsome, charming, maybe a little too aware of both things, but he made you laugh and he was easy to talk to. When he finally asked you out, you said yes mostly because there was no real reason to say no.

Leon found out during lunch, because Carlos had walked past your desk and asked if Friday still worked for you and you said yes. Leon had looked up from his coffee.

“Don’t,” you had said, pointing at him immediately.

“I didn’t say anything,” he said, lifting his eyebrows in a defensive way. “I was just drinking coffee.”

You had rolled your eyes, but the truth was, the date was not what made you nervous. You could go out with Carlos. You could flirt, have a drink, kiss him if the night went well. That part did not scare you. The part after that did.

Because maybe nothing would happen, but maybe something would. And if it did, you hated the thought of getting there and suddenly feeling like you had no idea what to do with your own body.

It was not that you were ashamed of sex. That was the frustrating part, you wanted it, you just did not have as much experience as people assumed you did, and you were tired of feeling like women were expected to automatically know how to be confident in bed without anyone ever explaining anything.

By Thursday night, it had been sitting in your head for days and Leon noticed before you even said a word.

You were at his place after work, sitting on his couch with your legs tucked under you, a half-empty box of takeout on the coffee table and your phone lighting up every few minutes with messages from Carlos. Leon had changed into a dark shirt and sweatpants, his hair still slightly damp from the shower, and he was watching you with that annoying look that meant he knew something was up.

“What’s on your mind, rookie?” he asked.

You looked at him as he brought you out of your thoughts “There’s nothing”.

Leon leaned back against the couch, one arm resting along the back of it. “You’ve barely touched your food.”

“I’m not that hungry.”

Leon scoffed “You’re always hungry.”

You glared at him, but it did not last. He knew you too well, and the worst part was that he knew when not to push. After a moment, you sighed and pushed the takeout box away.

“I need to ask you something,” you said, hands twitching as you thought about what you were about to say.

Leon’s expression shifted, just slightly. “Okay.”

You looked down at your hands. “I need sex advice.”

Leon went still, like his brain had taken the sentence, turned it over, and decided it needed more information before reacting.

“Okay,” he said slowly.

You shifted on the couch, feeling ridiculous now that the words were out. “I don’t want to ask my friends. They’ll make a big deal out of it. I want someone to be normal and explain it without making me feel like an idiot.”

You exhaled, forcing yourself to be clear because you were tired of dancing around the thing like saying it directly would kill you.

“I don’t have as much experience as people think I do,” you said. “I can flirt, I can kiss, I can act confident, but when it gets to actual sex I get in my head. I start thinking about whether I look awkward, whether I’m doing it right, whether I’m supposed to move a certain way, and then I’m not even enjoying it because I’m too busy trying to not look stupid.”

“Is this about that guy, Carlos?” he asked after a moment.

You made a face. “Why do you say his name like that?”

Leon gave you a look. “Is this about him?”

“Partly.” You hesitated, words coming out in a low tone. “I mean, yes, I have a date with him tomorrow, and maybe it goes somewhere, maybe it doesn’t. But it’s not really about him. It’s about me not wanting to feel clueless if I decide I want to sleep with someone.”

Leon nodded once, slow, like he was choosing his words carefully. “What do you want to know?”

God, were you really about to say this?

“I want you to teach me how to ride,” you said finally, cheeks burning. “Like… how to be on top, how to move... Basically, how to fuck someone without feeling like I’m doing a bad job.”

Leon’s eyes stayed on yours, but something changed in his face.

“Oh,” he said.

Despite yourself, you laughed, still hiding behind your hand. “God, this is humiliating.”

“It’s not,” he said, nervous but certain. “It’s really not.”

You lowered your hand enough to look at him. “You’re telling me that because you’re nice.”

“I’m telling you because it’s true.” Leon leaned forward, elbows on his knees, his voice calmer now. “It’s not humiliating to ask how something works.”

“I’m not asking you to do anything you don’t want to do, really,” you said. “But you are the only person I know who won’t make a big deal out of this”

Leon’s mouth twitched faintly. “You did choose a pretty effective way to make things weird.”

You groaned. “Leon.”

“I’m sorry,” he said with a small laugh. “I’m listening.”

You took a breath, then said it before you could lose your nerve.

“I’m asking because I trust you with this. I know you won’t make me feel dirty for wanting to learn,” you added. “And I know you won’t laugh if I’m awkward… So, what do you say?”

He took a few seconds to answer “Okay,” he said.

You smiled at him, feeling hopeful that your sexual frustration might finally ease tonight but that smile faded slowly when he shifted closer. He was giving you time to move back, to laugh it off, to say no, actually, never mind, let’s pretend I didn’t ask my coworker to teach me how to fuck.

You did not move back.

“Can I kiss you?” he asked, his voice a little lower.

The question was simple, almost too simple after everything you had said.

Your heart still kicked.

“Yes.”

He kissed you carefully at first, one hand coming to the side of your face, his thumb resting near your jaw. It was testing, warm, slower than you expected. You had kissed people before, but this felt different because it was Leon, and he seemed to understand your body before your head did.

You moved closer. That was when his hand slid to the back of your neck and the kiss deepened.

It still did not feel like he was rushing you. If anything, he let you set more of the pace than you expected. When your fingers gripped his shirt, he followed. You found a place on his thighs, where he made you comfortable by putting one of his hands on your thigh, pretty close to your ass.

When you opened your mouth under his to deepen the kiss, he made a low sound that went straight through you. When you pulled back to breathe, he stopped immediately.

“Still okay?” he asked.

You nodded. “Yes,” you said, breathless. “Still okay.”

“Do you want to take this to the bedroom?” he said, caressing your thigh, a faint blush crossing his face as he asked.

This was unbelievable, half an hour ago you were talking about unfinished reports and now you were making out and about to sleep with your coworker.

You looked at him for half a second.

Then you nodded again. “Yes,” you answered with a shy smile.

He stood and offered you his hand, which somehow made you laugh under your breath.

“What?” he asked, his cheeks still red from before.

“Nothing. It’s just very gentlemanly for the situation.”

That finally made him laugh, quiet and real, and the sound helped dissolve the last sharp edge of your nerves.

His bedroom was dim and simple, lit only by the lamp on his nightstand. It felt more private than the living room, but not in a scary way.

Leon turned toward you once you were near the bed.

He let go of your hand, and touched the hem of your shirt instead with a calmness that made your stomach twist. “Can I?”

“Yes,” you said.

He took it off slowly enough for you to help, revealing your breasts in a light pink see-through bra, then kissed you again before you had time to feel too exposed. That worked better than any compliment could have. You relaxed into his mouth, hands finding his shoulders, then his chest, then the edge of his shirt.

To your touch, he realized he was still clothed, so without making a comment, so he took his shirt off. When his shirt was gone, you tried not to stare too obviously.

“Don’t look so surprised,” he said.

You rolled your eyes, but your hands were already on his chest, tracing over warm skin and old scars with more curiosity than hesitation. Leon’s breathing changed slightly under your touch.

He sat on the edge of the bed and guided you closer, not pulling, just giving you somewere to go. You stood between his knees, and he looked up at you while his hands rested at your waist. You laughed quietly, and he kissed your stomach, his stubble tickling your skin, just above the waistband of your pants, cutting the sound off in your throat.

Leon looked up at you for approval to continue, checking for a second.

You did not tell him to stop, so he kissed you there again, this time, slower.

Your hand slipped into his hair without thinking, and the second your fingers touched him, something in his face shifted. Then, his hands started finding the clasp of your bra and unhooking it, removing it carefully from your skin, revealing your full breasts, nipples already sensitive from his attention. He then started kissing them and leaving small bites and warm kisses over the soft skin. His eyes flicked up to yours again, and for a second the whole thing stopped feeling like some strange lesson and started feeling like something you both wanted very badly.

His eyes were darker, with his gaze revealing that he was seeking something more.

He then guided you down onto the bed, opening your thighs, slowly taking off your pants first.

“Can I?” he asked, settling between your thighs, fingers on the waistband of your thong, matching the bra that was now on the floor.

You nodded, arousal growing in you because of your view: Leon Kennedy, between your legs, topless and asking you if he could give you oral. There were good dreams, and then there was this.

He slowly removed your underwear, kissing the path the fabric left on your skin until he reached your ankle, giving it a small peck too.

He settled now between your legs, giving sloppy kisses to your thighs, stealing repressed moans that you were keeping in your throat.

“Rookie, please, let me hear you” he said in a tone that felt like he was begging for your sounds.

Then, he went for your pussy. First, he started kissing it with his tongue, which gave you an electric shock through your spine. Then, he worked his way through your folds, making sure he reached everywhere.

You weren’t very experienced at sex, but you knew instantly that nobody ever was going to eat you up as well as Leon was doing.

He then penetrated you with his tongue, making you moan in pleasure, your hand going straight for his hair to make sure he wasn’t going anywhere.

“L-leon…” you managed to say in between your noises, which filled the room along with the wet sound of your pussy being eaten “I’m close…”

“Then I’ll get you there, angel” he said with a deep tone still on your pussy, making you moan at the vibration of his voice.

His pace quickened, devouring you with each movement his mouth made.

Finally, you reached your climax, coming against him. He didn’t pull away right away, he continued sucking your fluids until your legs fully relaxed.

By the time Leon came back up to kiss you, you were not thinking about Carlos.

That realization arrived quietly while your fingers were still tangled in Leon’s hair and your breathing had not quite gone back to normal. It should have made you feel guilty, maybe, but it did not. Carlos suddenly felt like a different conversation, a name on your phone in another room, something you had been using to explain nerves that had very little to do with him.

Leon kissed the corner of your mouth, his cheeks wet from you.

“You okay?” he asked.

You let out a small breath, almost a laugh. “You really just asked me that?”

“I told you already, I’m a gentleman” he said, with an ironic tone.

“Yeah,” you murmured. “I’m okay.”

His thumb brushed over your cheek, and for a second he looked at you in a way that made your chest tighten more than anything physical had.

Leon noticed, obviously, but he did not push. He only shifted beside you on the bed, giving you space, and that made it worse somehow. You had expected sex to make things messy. You had not expected his restraint to feel intimate.

Leon looked at your mouth, then at your eyes, and the silence between you became less awkward and more aware. You had spent months sitting beside him on couches, in cars, in briefing rooms, in quiet corners after work. You knew how he looked when he was tired, annoyed, amused, focused. You had never seen him look at you like he was trying not to want more.

You touched his chest lightly “Can I?” you asked, your eyes indicating between his legs.

Leon’s eyes flicked down to your hand “Yes.” He answered.

Before lying on the bed, he took off his boxers, revealing his cock.

You knew Leon was a big guy; you had seen him without his shirt more than once, but you still felt intimidated when you looked at him like this.

You sat beside him. First, you stroked it with your hand, stealing Leon some uneven breaths.

Once you saw drops of precum dropping out of his pink tip, you knew it was time. You spat on it, making sure it was wet enough and then, you started working your way on his tip with your mouth, your tongue going through every inch of his length.

Every time you sucked on it, it made Leon let out a moan. When you started to pick up your pace, you could tell it was getting harder for Leon to hold back, grabbing your hair tighter so you wouldn’t leave him unattended.

“Shit… Rookie are you sure you are the one who needed sex advice?” he said, his voice cracking with each moan. “You are going to suck the soul out of me if you keep going like this.”

Each thrust on your mouth was quicker, sometimes making you gag around him. When he felt he was close, he signaled you to stop what you were doing.

When you finally looked up at him afterwards, Leon had one hand over his mouth and the other tangled loosely in your hair, his breathing uneven.

You climbed onto the bed properly, kneeling beside him, and for a moment neither of you moved. His hand came to your waist, casual at first, then more certain when you leaned into it. You liked his hands there.

“So,” you said, trying to sound braver than you felt. “The actual lesson.”

Leon’s mouth twitched. “You still want it?”

You gave him a look. “That was the whole point.”

“Was it?” The question was not teasing, not completely.

You both knew it was not really the whole point anymore. Still, you nodded.

“I want to learn,” you said. Then, after a second, because the truth kept pushing its way out, “With you.”

Leon’s face softened at that. He lay back against the pillows and guided you over him, his hands steady at your hips. The position made you nervous all over again, but it was different now. You placed your hands on his chest for balance. Leon looked up at you, his hair messy, lips parted slightly, eyes darker than usual.

“Start slow,” he said. “And don’t think about what you look like.”

“That is impossible,” you said with a nervous laugh.

“It’s really not” he answered.

“It is when you’re looking at me like that.” You revealed.

He paused, doubt growing on his expression. “Like what?”

You swallowed, then said it before you could lose the nerve. “Like you like me.”

Leon went still. For a second, you thought he might dodge it. Make a dry comment, shift the mood, turn it back into something easier.

“I do, rookie” he said.

Your breath caught. Leon’s hands stayed on your hips, warm and careful. “I didn’t plan to say it tonight but well, things come how they come”

You let out a nervous laugh. “I didn’t plan to ask you to teach me how to fuck, so I think we’re both improvising.”

That made him laugh properly, and the sound loosened something in your chest.

“Fair enough,” he said.

You looked down at him, feeling suddenly less embarrassed than you had all night. “I think I like you too.”

“You think?” he gave you a funny look.

“Don’t push it, Leon,” you rolled your eyes back.

His mouth curved, soft and amused. “Okay.”

You leaned down and kissed him. You were both smiling a little, and your balance was not great, and one of his hands had to catch your waist when you nearly shifted too far to one side. When you pulled back, Leon brushed your hair away from your face.

“Ready?” he asked.

You nodded. “Yeah.”

You settled yourself on top of him, Leon guiding his cock to your now dripping wet entrance. Slowly, you started to sit on it, taking his inches inside of you, making you moan at his thickness and making him groan at how tight and wet you were. Once he was fully inside, Leon put both of his hands on your hips, grabbing onto your fat.

“Once you’ve adjusted to it you can start moving, take your time, baby” he said, holding back a moan. Him calling you baby only made you even wetter.

When you started moving it was kind of complicated, you were struggling to find your rhythm, getting tired at the position of your legs, starting to feel frustrated with each thrust.

“Hey,” Leon said. “Try using your hips rather than your legs, it doesn’t have to be quick… just find your sweet spot.”

His words reassured you, and as he said, you started moving your hips in circles, starting to feel better with each movement, and you noticed Leon was feeling that too, as his sounds were getting louder.

Of course, you were doing a great job so far, but the view he had of your breasts bouncing with each movement, hair strands getting on your face and the sound of your ass cheeks slapping against his skin was also turning him on.

He moved your hands from your sides to on top of his chest for you to feel more comfortable. When you moved in that position, with your back arched, you felt how you reached that sweet, spongy spot you heard everyone talk about but you didn’t know till this moment, with the tip of Leon’s cock hitting right deep inside you.

That’s what made him basically melt. With each one of your following movements, Leon only kept getting louder and louder, his muscles twitching below you, hands grabbing your ass cheeks as hard as he could. What started as a class for you to learn how to ride, turned into a session of Leon losing control to the woman above him.

After a few minutes like this, you both felt your climax getting closer. It didn’t take long for Leon to get there, finishing with a broken groan as you followed him over the edge, both of you giving in completely.

Afterwards, you collapsed against him with a breathless laugh you could not hold back.

Not because it was funny, exactly. More because the whole thing felt unreal in the most human way possible. You had come to Leon’s apartment worried about a date with another man, and now you were naked in his bed, tucked against his chest while he tried to catch his breath under you.

Leon’s hand moved slowly up and down your back.

“You laughing at me?” he asked, voice tired and warm.

You lifted your head. “Maybe.” You smiled, then hid your face against his shoulder because it was easier than letting him see how happy you looked.

Leon’s fingers paused at your back. “Hey.” You hummed. “You okay?”

You nodded against him. “Yeah.”

For a while, neither of you moved. The room was quiet except for your breathing, the lamp still on, the sheets tangled around your legs. It should have felt awkward now that the heat was fading, but it did not. Eventually, Leon shifted and pulled the sheet higher over your back.

There was a softness in him now that you had only seen in small pieces before. In the office, it appeared for a second and disappeared just as fast. Here, in the low light of his bedroom, he seemed too tired to hide all of it. His hair was messy, his expression calmer, his hand still tracing idle lines along your spine. You touched his chest with your fingertips.

“So,” you said. Leon looked mildly suspicious. “What happens now?”

He took a breath, then let it out slowly. “I was hoping you’d ask something easier.”

You smiled, but your nerves returned a little. Leon noticed, because of course he did, and his hand moved from your back to your jaw, his thumb brushing lightly near your cheek.

“I don’t want this to be weird at work,” he said. “And I don’t want you to feel like you have to decide everything tonight. But,” he added, eyes on yours, “I also don’t want to pretend this was just me helping you with a problem.”

Your throat tightened.

“No,” you said softly. “It wasn’t.”

His gaze searched your face. You were the one who looked away this time, but not because you regretted anything. Because saying the truth felt more vulnerable than everything you had done in that bed.

“I didn’t think I liked you like this,” you admitted. Leon was quiet. “I knew I trusted you. I knew I liked being around you. I knew you were attractive, obviously, I’m not blind.” His mouth twitched. “But I didn’t think about it properly,” you said.

Then your phone buzzed somewere in the living room, both of you froze. Leon looked toward the door, then back at you. “Carlos?”

“Probably,” you said, staring at each other for half a second.

Then you buried your face in his chest and groaned. “Oh my God.”

Leon’s chest moved with a quiet laugh. “You do need to answer him eventually, but preferably before tomorrow and… maybe don’t mention the lesson.”

You lifted your head and hit his shoulder lightly. “Leon.”

“What? I’m helping.” He looked far too satisfied with that one.

“You’re insufferable,” you muttered.

You rested your chin on his chest, trying to look annoyed and failing completely. “I’ll cancel the date.”

Leon’s expression shifted, the humor fading into something more careful. “You don’t have to because of me.”

“I’m not doing it because of you.” You paused. “Well. Not only because of you.” His eyebrow lifted. “I don’t want to go,” you said honestly.

Leon did not smile immediately, but his hand moved gently over your back again. He leaned in and kissed you softly. A quiet, unhurried kiss that made the whole night feel less like an accident and more like the beginning of something neither of you had planned well enough to stop.

When he pulled back, you stayed close.

“I like you,” he said, so plainly that your heart tripped over itself.

His fingers brushed your hair away from your cheek. “I’d like to see were it goes, if you want that too.”

“I want that too,” you said.

Leon nodded once, like he was trying to keep his cool, but the little relieved breath he let out betrayed him.

You smiled. “You were nervous, Kennedy.”

He sighed. “Maybe a little.”

That made you like him even more. You curled against him again, your body warm and tired, his arm settling around your waist beneath the sheet.

“You know,” you murmured, already half-asleep, “you’re a pretty good teacher.”

Leon’s arm tightened around you. “Don’t say that at work.”

You laughed against his chest. You kissed him once more, soft and sleepy, and settled back against him while he reached over to turn off the lamp.

Work was surprisingly normal after that night.

Leon still treated you the same in front of everyone: the same quiet looks across the briefing room, the same habit of leaving coffee on your desk when he knew you had skipped breakfast. The difference was in the little things no one else would have noticed unless they were paying too much attention. His hand brushing your lower back when he passed behind you, the way his eyes softened when you looked at him from across the room.

A few days later, you were by the training rooms, filling your water bottle after a long session, when Carlos leaned against the wall beside you.

“You did good in there,” he said, giving you an easy smile.

You glanced at him. “Thanks.”

“I mean it. You’ve gotten better.” His gaze lingered for just a second too long. “Stronger too.”

You gave a small laugh, polite but not encouraging. Before you could answer, Leon’s voice came from behind you.

“She’s busy.”

You turned your head just as he walked up beside you, calm as ever, holding a file in one hand and your coffee in the other. He did not make a scene. He did not glare. He simply stopped close enough for his shoulder to brush yours and handed you the cup like it was the most natural thing in the world.

“Forgot this,” he said.

You took it, trying not to smile too much. “Thanks.”

Leon’s hand settled briefly at your waist, light and familiar, just long enough to make the message clear without him having to say anything else. The other agent looked between you both, understood, and pushed himself away from the wall.

“Right,” he said, smile fading into something more awkward. “See you around.”

When he left, you looked up at Leon.

“Am I busy?” you asked.

His mouth barely curved. “You are now.”

You rolled your eyes, but you were smiling when he leaned in, just enough to press a quick kiss to your temple before walking away like he had not just made your whole stomach flip in the middle of the hallway.