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You sigh as you circle the city block for the second time in a row, trying not to brush shoulders with the other bar crawlers populating the sidewalk as you look at your phone, wishing you’d worn something warmer. Your ears are filled with the quick clicking of your heels and the distant sounds of lively crowds and bass beats escaping through the doors of each bar you pass, somehow none of them being the one your friends claim they’re at. You’re absolutely on the right street, and you’re getting increasingly annoyed at their drunken attempts to guide you there through text, and your own navigation abilities aren’t their best at two drinks in, regardless of how the cold has sobered you. You pull off against a building to stand out of the way and put your phone in your purse, and see your pack of cigarettes half-smashed in the bottom. Why the hell not. Maybe a minute to yourself will put you in a better mood.
You hold one in your mouth as you rummage through your bag for a lighter. Which helps your sour mood less and less with each unsuccessful second.
You duck into the alley next to you, knowing it was well-lit and where someone must be smoking. And your assumption was correct; your first stroke of luck tonight.
He was leaning against the wall, a darkened figure in his boots and leather, grown-out hair covering his expression. There was definitely a voice in your head saying stranger danger, but you were well within someone-will-hear-me-if-I-scream distance from the street, and this wasn’t exactly a shady alley, more of a shortcut to the other side of the block. So you approached.
“Excuse me, do you have a light?”
He looked up like he was surprised at being approached, but nodded his head and searched his jacket pockets, finding it second try. He flipped it open and lit it for you, holding out his gloved hand for you to light it over. A zippo, very classy, you thought.
He was older than you, you could tell for certain. The deep lines in his brow and the salt and pepper in his short facial hair gave away his age, and gave away some years of hard living too, but he really didn’t look half bad. His hair was a touch lighter than it looked from afar, ash blond instead of brown, which somewhat softened his overall appearance. But it’d be hard to look anything less than handsome with bone structure like that.
Not that you were staring. You nursed your cigarette against the wall adjacent to him, settling into a silence that was only a tiny bit awkward, slight enough to ignore as you watched each exhale turn to fog in the cold air. But still, you wanted to talk to him. It was nice to have your mind on something other than your night thus far.
So you broke the silence to tell him your name, not quite looking at him when you did, but you could feel his attention turn to you. “Leon,” he offered in return.
“Leon,” your tried it out for size, “that’s a nice name.”
“Thanks, it was a gift from my mother.”
You chuckled at that. Okay, so he’s not a total creep, he’s making nice and normal jokes. This is good.
“So, what brings you out tonight, Leon?”
“I… guess I kind of got stood up.”
“Oh,” you said, a little surprised, “I’m sorry to hear that.”
“Don’t be,” he replied. “Just a lesson I needed to learn again, I guess.”
You nodded like you understood more than you did, but it seemed like a topic you shouldn’t get too much into with a man you just met, and the silence lingered a bit more than you wish it had this time. He put his cigarette out against the wall and pulled out his pack, trading the filter for another that he lit to continue talking. “And what brings a nice girl like you here with me?”
You couldn’t help a small smile creeping out at the corner of your lips at the flattery. “I don’t really like my friends,” you said sarcastically, rolling your head against the wall to look at him. “I had to take a phonecall and they went to another bar, and I haven’t been able to find them.”
He asked where you were trying to go, and learned that it’s a 15 minute walk away. You liked your friends even less now.
He offered to walk you, but at this point you’d rather walk back to your car and sit until you’re sober than rejoin them just to fuss them out and spend the night drinking with people who clearly didn’t like you all that much. You’d known them for a few months now, but no matter how often they invited you out, you never felt like they truly wanted you in their years-established friend group. And when you thought about it, you didn’t have much in common with them. It felt like they invited you out for their entertainment more than anything.
You explained this to him in more surface-level terms and thanked him for his offer anyways. And you did appreciate it. You could probably walk in the shadiest places and be treated with the utmost respect with a man like him by your side. He could probably look pretty scary if he was mad. And probably pretty hot. You were always a sucker for male RBF.
You made small talk, not really learning much about eachother in the process, but the conversation flowed easily until his second cigarette was burned through.
“Is this the part where I buy you a drink?” he asked.
You looked back towards the street, thinking about it. You definitely weren’t going back with your friends now, and you weren’t quite sober enough to drive home, so you’d have to call a cab whether you had another or not. He’s been nothing but a gentleman so far. He doesn’t litter. And you’re really interested in knowing what’s under that leather jacket. So you agreed.
You followed him back out onto the street, trusting in his choice of bar. “There’s a little place upstairs at this hotel, I think you’ll like it.”
And wow, you did. You had to take an elevator up, so you were wonderfully far removed from the cold unforgiving air outside, and the bar’s ambience was as cozy as its temperature. The whole floor was a dimly lit lounge, with the bar placed in the middle and floor to ceiling windows all around, giving you a panoramic view of the skyline twinkling as far as you can see. And since the seating was ample, although there was a healthy number of people there, it felt like you were in your own little space on the velvet couch you settled into. It had been a while since someone had taken you somewhere so nice. You were glad he was paying, and you were suddenly grateful you chose fashion over function when you got ready tonight.
And you were not let down by his physique. You think you went a little slack-jawed when he took his jacket off and tossed it on the arm of the couch. You’ve never seen a man make a sweater look tailored purely by how obvious his muscle tone is underneath it. When he pushed up his sleeves to look at the menu, you nearly bit your fist. You picked up your own menu to at least stop staring.
He asked you what you wanted and you went with the first thing that seemed to fit your taste, and took in the city view while he went to the bar to order, thanking god you had a minute to think about your next move in peace, because your night had taken an unexpected turn. What was supposed to a night of bouncing between dive bars with your shitty friends has turned into being at an upscale speakeasy with a stranger who also happens to be the hottest man who’s ever so much as looked at you. He also happens to easily be the oldest man you’ve been out with, but you couldn’t possibly care less when he looks like that. You sent your bestie your location with a text that said wish me luck and put your phone on silent.
Time seemed to fly after Leon returned with your drinks. He was easy to talk to, and good at making conversation even though there were plenty of things he didn’t want to share about himself, which is fair. His vague “military-adjacent” career explained that along with the great shape he was in. He subtly made it known that dating was basically out of the question for his lifestyle, which was honestly fine by you. It was a breath of fresh air to be out with a man for the first time and not feel like you’re being interviewed for the role of their wife, or having to turn into their therapist, which has been the bulk of your recent dating experience with men your own age.
And he was quite worldly. You weren’t at a point in your career where you could travel to all the places you’d like to go someday, and he’s been all around the globe, offering you little bits of advice on where to go and where to avoid at all costs that you hope you remember to write down tomorrow. You felt a little uninteresting in comparison, but he seemed genuinely engaged in your anecdotes, telling him about the concerts you’ve been to, your adventures working in the arts and how it brought you to the boring office job you have now, and all the things you want to experience next. None of which happen to involve a man, and none of which made him insecure in the slightest. You were having the best date of your life, and it was totally by accident, with the kind of man you never thought you’d go for but was making you want to jump his bones from respectfulness alone.
So much so that when he took your empty glasses to trade them for another round, you shifted to sit closer to the center of the sofa to be closer to him. Between the alcohol-induced confidence, how badly you wanted this to go somewhere tonight, and the clock ticking towards midnight, you were being much braver than your usual self. And when he returned, he sat closer, too, with his body facing towards you and an arm ever so slightly around you where it lay on the backrest.
“I hope you’re not trying to liquor me up,” you said playfully as you took your drink from him.
His eyes went a little bit wide as he drank his. “No, no, that’s not what I’m trying to do.”
You laughed coyly at his earnest reaction. “That’s alright. I just thought I’d tell you that you don’t have to.”
“Oh,” he said almost as a question. “I won’t lie, I figured your friends must be really unpleasant if you came here with me.”
He must be absolutely clueless to how good he looks, and you had to stop yourself from fully laughing at him for it. “No, really,” he continued. “Maybe when I was your age, but I don’t know why you’re here with the man in front of you.”
“Well, I don’t normally go for men in alleyways, but you were being so polite and looked so good, it was an offer I couldn’t refuse.”
“I’m glad my charm hasn’t faded entirely,” he said lowly, and moved his hand to gently pet your hair. He was looking at your lips, but he wasn’t moving an inch further. So you shifted to sit even closer, your knees now able to touch, and put down the remnants of your drink. You looked at his lips and squeezed your thighs together, noticing just how turned on you’d become, and then looked back in his eyes expectantly until he finally closed the distance.
It was too soft and restrained to be full on making out, but it was close enough. With each pressing of your lips he’d pull away after as if he was pulling back on the reins with great effort. He tasted like bourbon and smoke and salt, and you could smell the cologne on his clothes, leading you to hold his sweater in the gentlest fist to get him just a tiny bit closer. You looked down between kisses and looked at the bulge in his pants and the belt buckle you were dying to pull off.
“Is this the part where you take me home?”
He looked into your eyes like if there was any less of a lustful cloud over him, he’d tear you in two. “Yeah,” he breathed out. “Please.”
He stood up quickly to put his jacket on and take out his wallet, throwing cash on the table and offering you his hand. You took it and followed him back to the elevator where his arm moved down, first to your waist and then your hip and up your jacket, just enough to breach the hem of your shirt and feel your skin underneath, and you let yourself be pulled tightly against his side. In the reflection of the chrome walls, you could see that his eyes were impatiently fixed upon the floor numbers descending until they opened on the ground and he was pulling you hastily out the door and into the streets.
It was thrilling, letting him rush you towards an unknown location while the first bits of snow began to fall around you, trying to keep up with him in your heels while you were kept warm by your closeness. You hurried across the street and into a parking garage until he was holding open the passenger side door of his car and rushing to turn over the ignition. As soon as he did, he hit your seat warmer on and crashed his lips into yours. Nothing about him was holding back now.
Finally your hands were able to explore to their content, unzipping his jacket and grabbing him underneath it, feeling how warm and how firm every muscle was, from his sides to his chest and shoulders, until the heat was coming through the air vents and he shrugged it off of himself. All the while you traded spit in open-mouth kisses, neither of you wasting time to apologize when your teeth gnashes against eachother, because you really didn’t care. Your own coat had come off at some point and he had one leg travelling up your thigh closer and closer to your crotch, and the other holding tight to the skin under your shirt, travelling up to run his thumb across the front of your bra, not yet daring to take either off. You grabbed at this belt to give him the hint, but he broke away from your mouth, both of you breathing hard.
“You sure you want to do this here?”
You nodded fast and only got halfway through the word “yes” before he’d pulled you completely over the center console and into his lap, pressing you down to grind against him while he fumbled with the controls to push his seat back and give you more room. When you grabbed at his belt again, he pushed his hips up and ripped it off himself, giving you a head start on unzipping his jeans and pulling him out.
And oh god were you almost scared at his size. He was more than average length, but he was thick, and it had been so long for you that you were actually a little concerned about it fitting. At least you were already in his lap and weren’t able to attempt to take him in your mouth, as much as you’d love to, because you were sure you’d lose your voice tomorrow if he fucked your face like you wanted him to. How small your hand looked on it only exaggerated it.
If he was insecure about his looks earlier, he wasn’t insecure about this, because he knew exactly what thoughts were making your movements slow down. He pulled you in by the nape of your neck and kissed you before saying, “don’t worry, I’ll start slow,” and that was all the reassurance you needed.
You fervently tore his sweater over his head and threw it in the backseat and he did the same with yours, your hand only leaving his cock when it absolutely had to, and he started working on your bottoms, only bothering to take them off of one leg so you could move freely and he could pull them down enough to grab and spread your ass in his big hands.
And now that he was as naked as possible given the circumstance, he did not disappoint in the slightest. You could see every muscle flex distinctly as he shifted beneath you, moving you further up in his lap until his fingers could find their way in between your folds.
You held onto his shoulder for purchase as he worked them in, first with one, periodically pulling it out to rub your clit before plunging in again. “Shit, you’re tight,” he said through his teeth, “even tight on my fingers. You really gonna let me ruin this tight cunt of yours?”
Words could not describe what that did to you. He was taking care to get you ready, and it’d been so long since you’ve been fucked into oblivion, and at this point you’d beg for it from him if he asked.
He pulled his fingers out of you and took them into his mouth, furrowing his brows closed and moaning at the taste of you. “I wanna eat you out so bad,” he said, and reclined his seat as horizontal as it could go, “wanna spend hours making you cum. Get up here.”
You have no idea how you were able to contort your body to sit on his face, but you did. You put your arms behind you on the dash so you wouldn’t fall back on the horn, using the little leverage you had to grind down on him as he held your hips even tighter to his face.
You were trying to keep your moans to a reasonable level but it was a failed effort. When he wasn’t sucking on your clit, his nose still pressed against it while he buried his tongue inside you, the stubble of his facial hair adding an extra layer of friction between your thighs. Reaching up, he blindly unclasped your bra and took your breasts in his hands, thumbing your nipples and squeezing them just enough to barely hurt. The sheer amount of sensation sent shocks throughout your body until you were saying his name and he lapped up your cum like a madman dying of thirst.
When you’d just begun to catch your breath, he let you bring your hips back to his throbbing dick, leaving a wet spot on him as he pulled you into your filthiest kiss yet. When you pulled away from his mouth, it was only to find enough focus to return the favor and reach down to line him up with you. He let out a shaky breath as you lowered yourself slightly, just enough to take in the tip, and then back down to fit more of him inside each time.
“That’s it baby girl, you can take me. Take your time.”
And you did until you were finally able to fully sit on him, feeling every inch as full as you were. With him all the way inside you kissed him again, grinding down in a way that maybe only felt good for you, but let you fully adjust while he pressed against the deepest parts of you.
He grabbed your hips and lifted them up just a little, then guided them all the way back down, nice and slow, your foreheads resting against eachother.
“That feel good?”
“Mmhmm,” was all you managed to whimper out.
“You ready for me to fuck you now?”
“Yes, god, yes.”
He wasted no time to thrust into you sharply. You gasped. Then he did it again. And again. And again. With each pause between the hard force of his cock leaving you an absolutely desperate mess. Only when your hands were scrambling across his body and all you could say was “please, please, Leon please” did he finally let himself fuck you with all the force he’d holding back.
He had one arm holding you close across your back and the other on the back of your thigh keeping your legs apart as he drilled into you hard and fast, your mouth open slack against his neck and you focused on breathing and just taking the punishing pace he was dishing out to you, whispering filthy things into your hair, like, “your cunt is so goddamned good,” “I can’t believe you’re letting me wreck you like this,” “couldn’t even wait to get home, had to have it right here in public, didn’t you?” “You’re taking it so well baby, such a pretty pussy, you gonna let me cum inside? Yeah? Gonna let me fill you ‘til you leak?”
He moved his hand from your thigh to your clit and that was all it took to make you cry out again. His other hand grabbed you by the nape of your neck. “Look at me, look at me when you cum.” And it was game over.
His face twisted into a snarl as he teetered on the edge, and if that was the face you’d first met tonight, you would have run screaming in the other direction. But here in his car with him fucking you absolutely dumb until the windows fogged up and his suspension shook, his otherwise scary expression made you scream his name and cum even harder around him than before, his orgasm following with a mangled shout. He threw his head back as his thrusts lost their rhythm and his grip on you tightened, and you saw a bead of sweat glisten down his neck at the same moment you felt his cum spill outside of your walls.
You sat there huffing, glued together, teeth buzzing and borderline lightheaded as you came down from it. When he looked forward again you watched his eyes trace their way from where your bodies connected all the way up to your undoubtedly fucked-out face. He grinned devilishly when his eyes met yours, and you sighed out a single laugh, smiling until he finally pulled out. You moaned again from the loss and the feeling of so much cum spilling out of you and onto his lap. Good thing he had leather seats.
He rubbed your legs soothingly until you looked for your discarded clothes, and he reached into the backseat to find them and hand them to you, finding his own and offering it to you to wipe off with. You got yourself halfway-decent again, putting your top on and combing your hands quickly through your hair, trying to fix yourself at least somewhat, because it was more than safe to assume you looked at least half as ravaged as you had been.
He adjusted his seat back to half sit so there was still room for you in his lap. “Hey,” he started, replacing your hand in your hair with his own, running his fingers through it softly. “That was incredible.”
You took a minute to look at him, taking him in. His hair was tousled and pushed out of his face, a light sheen of sweat painting his entire form, the flush on his chest revealing scars you hadn’t noticed before. You ran a hand up his torso, appreciating his body and the warmth emanating from it once more before you’d have to climb off his lap and into the passenger seat. “Yeah, it really was.”
He brought you in for one last kiss before he let you switch seats and fully dress yourself, no choice but to sit in your soaking underwear and feel how sore your pussy would be tomorrow. For now, you thanked god for the soothing powers of heated seats, and blushed as you imagined him cleaning them tomorrow.
The drive to your place was quiet but comfortable, with the radio playing low and his hand on your thigh. He pulled into your driveway just after 2am. Before you got out he asked for your number, but said he couldn’t give you his. Something about only having a work phone, “but if you need me to take you back to your car tomorrow I will, or if you need me to uh, take you to the pharmacy, I’ll pay.”
You smiled and assured him it was alright, you wouldn’t have let him cum inside if it wasn’t safe, but he was welcome to call you on a pay phone or whatever it was he used instead of his cell anytime. He waited in the driveway until you were safely inside where you promptly kicked your heels off and passed out.
You woke up at noon with a persistent headache, a million texts and a hundred missed calls, none of which from an unknown number. When you found the energy to leave your house, you discovered a little brown gift bag by your door. You opened it to see a plan B and a notecard:
“Next time I’ll take you out to dinner first. -Leon”