Work Text:
When you came across Obi-Wan’s profile on Tinder, you stopped your mindless swiping to actually take in the information before you. No man who looked like that should rightfully be on an app typically reserved for finding hookups. How could this face and the man attached to it not be pulling all the pussy he wanted without the help of this “matchmaking service”? He could probably go to any bar in any town and walk home with options to choose from. You pressed his profile picture, desperate for more information, and you were not disappointed. “Obi-Wan (Obi) Kenobi. Fencing instructor, Ole Miss alum, proud uncle. 420 friendly. Not looking for anything serious, but we’ll see how it goes. Let’s get drinks sometime.” We’ll see how it goes. Yeah, how many times had you seen that line? Too many. Typically that line indicated you would get ghosted after you gave yourself up, but Obi’s stormy eyes drew you in. Perhaps it would be worth it, and it couldn’t hurt to try. You exited out of his bio and decidedly swiped right.
“It’s a match!” the app immediately alerted you. Your heart started pumping a little faster, the typical anxiety you got every time you made a connection. Not that there had been many of those lately; you only used the app when you were bored and needed some excitement in the form of meeting some stranger at some strange place, never to meet again.
As you were wracking your brain for how in the heck to start a conversation with this man who, by all rights and accounts, was well out of your league when he beat you to the punch. A new message was waiting in your inbox. He wanted to meet for drinks, and you agreed. At least this one was willing to meet in public. Tinder has never been the most reliable way to meet the people you think you’re meeting, and you had learned that lesson the hard way.
Four hours and a call to your best friend later (she was a dear and would not be to bed tonight until you texted her that you were at least safe, if not home in your own bed), and you were sitting in, yes, a strange bar, waiting for this strange man to appear. You had arrived early, as usual, out of anxiety, and were now sitting at the bar in a skin-tight cocktail dress, your favorite for occasions like this. The midnight blue fabric left enough to the imagination, but complimented your curves in the best possible way. You knew you looked good; the confidence this dress gave you would be enough to coast on should Obi be a no-show, which seemed to be a growing possibility.
“Hey baby, how you doin’?” You jump at the low voice at your left shoulder and look over. It wasn’t Obi-Was Kenobi as he was in the profile pictures, that much was certain. He was short, with greying hair, and already drunk enough to smell the booze on his breath. Off-putting to say the least.
“Just waiting for a friend,” you respond shortly, and turn back towards the bar, hoping the bartender would come back around soon. You would accept his offer for a drink this time; no point waiting for someone who might not show anyway. Besides, you needed an excuse to get this guy away from you.
“A friend, huh? Is she hot too?” His dark eyes looked you up and down as if surveying a buffet table, not sure which dish he should sample first. You cringed as he reached his hand up, not wanting to be touched but not knowing how to deny this stranger without putting yourself in potential danger.
“I don’t know, am I?” A new voice arose, this time from behind your right shoulder. You turned and were delighted and amazed to see the face you had started to think you would never behold.
The first man now had an offended look on his face, which melted into pure, unadulterated anger that this pretty boy had insinuated that he, a Very Manly Man, could possibly think another man was attractive. “What the fuck did you say?”
“I asked if you thought I’m hot,” Obi-Wan responded. “Go home and rethink your life. You don’t need to be hitting on girls half your age, especially when they are clearly not interested.” He wrapped an arm around your waist; typically contact this soon would be a red flag, but in this case you welcomed it, and leaned into his touch. He waved his arm, shooing the old pest away, then turned his attention fully onto you. “Sorry I was late. You shouldn’t have had to deal with that,” he apologized.
“It happens,” you replied. “Unfortunately, I’m used to it.” Despite being attracted to them, you had learned that by and large, men were dogs that would take advantage the first chance they got. “What are you drinking?”
“Hey, that’s my question. I’m buying tonight.” He raised a hand, two fingers extended, and flagged down the bartender, who until now had been conveniently elsewhere. “Are you a shots girl or a mixed drink girl?”
“Either,” you responded. Your drinking habits changed as often as the men next to you did; men liked you better when you could drink like them. “You?”
Obi smirked. “Shots, then. What’s your pick?”
You hesitated, then answered, “I’m a sucker for pickleback shots, if you’re down for that.”
The bartender sauntered up to the pair of you, and Obi ordered a whopping three shots for him, and three for you. “Just so we don’t have to worry about flagging him down later,” he explained.
The shots came back ten minutes later, enough time for the two of you to talk and for you to decide that yes, this had been a good idea, and if he asked you would willingly go to bed with him tonight.
“Shall we do a toast?” Obi had the first shot ready, one glass in each hand. You nodded, and he went on. “To meeting new people, to fine food and better booze!”
“Prost!” You clinked your glasses together, tapped them on the table, and downed the first shot and chaser. The pickle juice cut through the burn of the whiskey, leaving a salty taste in your mouth. It immediately warmed your belly like embers in a dying fire warm your hands.
The second and third shots disappeared quickly, and before you knew it, the background of the bar was swimming in and out of focus. The thought crossed your mind that you should have taken them slower, but the liquid courage was coursing through your bloodstream already, it was far too late to turn back. You asked Obi if another shot was in order.
“Well, if you’d be more comfortable in a quieter setting, we can continue this at my place,” he whispered into your ear, his hot, boozy breath tickling the skin at your hairline. His hands, until now respectfully kept to himself, were inching closer to you. Anticipation was starting to build deep inside both of you, it seemed.
“Let’s go then,” you whispered back, and he took your hand, helping you down from the barstool and leading you towards the exit.
Obi hailed a cab, and told the driver some address you couldn’t quite make out. On a sober night, you never would have gotten into a cab with a stranger, especially not knowing the destination, but there was something comfortable about Ben; you trusted him already somehow. Whatever happens, happens, you thought. Life isn’t worth living if you don’t take risks.
As soon as you were both safely in the back of the cab, the driver pulled out into traffic and Obi pulled you in. He held your chin with his forefinger and thumb for a minute, looking into your eyes as if the secrets of the world were hidden there, then closed the rest of the distance between you himself and kissed you. That kiss, hot and passionate, was more than enough to solidify in your mind that what you were doing was right somehow, and you fully gave yourself up to the experience. You leaned into his kiss, raising one of your own hands and tangling your fingers in the long, auburn hair that brushed the nape of his neck. One of his hands found your exposed thigh, and ran up and down the length of it, gently—so unbearably gently—then held your waist, pulling you as close as he could in the confines of the cab’s backseat.
By the time the cab pulled up at Obi’s apartment building, your panties were damp with anticipation of what was to come. Your head was still bleary from the shots, but you were sobering up enough to be lucid through the experience. He led you into the building, and, mentioning that he lived on the second floor, led you past the elevator—a piece of printer paper taped to the wall next to it read “Out of Order”—and towards the stairwell.
“Wait, wait, wait,” you mumbled, and bent over to slip off your heels. “You’ve got me fucked up if you think I’m walking up stairs drunk in these shoes.” You didn’t mind taking your shoes off; it beat a broken ankle, anyways.
His eyebrows drew together as he frowned. “I’m sorry, chickadee, I should have thought of that.” You started to tell him that it was fine, when suddenly one of his arms was against your back, the other against the backs of your knees, and just like that he was carrying you up the stairs princess-style. Shocked by the ease with which he was carrying you, you decided not to protest, and instead placed a gentle kiss on his neck.
Ben didn’t put you down until he tossed you onto his bed. “Would you like another drink, love, or shall we get down to business?” He stood above you, his eyes looking bluer and kinder than they had at the bar.
“I could go for a little more whiskey if you have it,” you replied, finally succeeding in removing both shoes.
He nodded, and made for the door leading to the kitchen. “Make yourself comfortable then, I’ll be right back.” He left your line of sight, and you took in your surroundings for the first time. The bed was covered in silk sheets and a luxurious comforter, and the mattress and pillows both felt like memory foam. Well, at least if the sex was mediocre, you would be comfortable during the fact. The walls of the room were covered with bookshelves filled to the brim, and a couple plants sat in the windowsill.
You were still turning over in your mind the possibilities for what kind of man Obi really was when he returned in the doorway, a glass of whiskey on the rocks in either hand. He handed one to you, and sat down next to you on the bed when you accepted. “I don’t want to break the mood, but can I ask you something?”
This break in Typical Hookup Routine caught your attention right away. “Of course, is something wrong?” You take an anxious sip of whiskey, wincing at the burn and regretting not asking for a chaser.
“No, no, nothing’s wrong,” he assured you, putting a hand on your thigh. “I just wanted to ask if you’re comfortable with this. I don’t usually do this; I’m still getting used to the rules.”
This time you couldn’t keep your surprise contained. “Really? I would have thought you do this all the time, the way you look.”
Obi laughed. “I’m not sure if I was just complimented or insulted, but really. Is there anything I should refrain from doing? Do we need a safeword?”
Now it was your turn to laugh. This impossibly sexy man was asking you of all people what the boundaries were. This was a new experience, but by no means an unwelcome one. “Look man, as long as you don’t try to stick it in my ass, I think we’re gonna be okay. I don’t do anal on first dates.” You tipped him a wink and downed the rest of your whiskey. “Shall we?”
He stood up, placed both glasses on the nightstand, and unbuckled his belt. As unfamiliar with hookup culture as he was, he was no stranger to the act of lovemaking itself. He knew exactly what he was doing and how to tease the object of his lust. His groin was right at eye level for the time being, and you could see that he, too, was anticipating the night ahead. His cock was straining the denim of his already tight jeans, and your pussy was getting warmer and wetter by the second. You weren’t sure how much longer you could wait.
He unbuttoned his jeans, stepping out of them when they fell around his ankles. Next to leave was his shirt, and you were glad to see it go. He was muscular, but not in the supermodel way. The years of fencing training and instructing he had done had clearly paid off. His chest and shoulders were broad, and his arms clearly held years of finely tuned movements within them. This was a man who knew how to use his body, and you only hoped that he would know how to pleasure yours half as well.
Knowing your usual role at this point in the encounter, you reached out to free him from the constrains of his boxers, ready to take his length into your mouth, but he grabbed your wrist before you even reached his waistband. “No, no, chickadee. You’re my guest. Guests get served first.” He pushed you back so you were lying on the bed, knelt on the floor between your legs, and slowly pulled your panties off from under your dress. Your thigh shivered as his fingers brushed it, and your breathing was starting to pick up.
He pushed your dress up out of the way, and you could feel his breath heating your already warm skin. He paused only for a moment, and then all the gentleness evaporated from him as he dove full force into your pussy. His tongue licked first at your clit, causing a precursory moan from your throat, then moved down to truly get a taste of you. He moaned, clearly pleased with the flavor, and you could feel his tongue moving inside you, flicking from side to side, up and down. As he switched back to pleasuring your clit, one arm reached up, trailing along your stomach, then caressing your breasts through your dress, which with each passing second you wanted torn off more and more. Your fingers found purchase in his long hair again, but this time you twisted the strands around your fingers, pulling him as close to you as possible.
Obi’s tongue didn’t stop moving until your hips were bucking under him, on the precipice of an orgasm, and just before you came, he pulled away, eliciting a small moan from you once more. He leaned up to you to place two of his fingers in your mouth, letting you suck on them for a moment before removing them and moving back towards your aching pussy. He entered you with first one finger, then added the other. Those fingers curled inside you, gently massaging the walls of your cunt. His mouth was back on your clit then, licking and sucking, and the combination of his movements was almost too much for you to take. Your back arched and you let out a cry as you came. Obi brushed his fingertips over your clit as he drew them out of you, and looked up. He was smirking again, and when he pulled up to kiss you, you could feel your juices on his beard.
“Take it off,” he mumbled into your lips, pulling at your dress. You didn’t have to be told twice. You desperately pulled the side zipper down, and wriggled out of the dress as quickly as you could while still lying down. In doing so, you turned your head and saw something you hadn’t noticed upon your initial survey of the room—a camera on a tripod stand.
“Is… is that on?” You asked. You weren’t opposed to being filmed, but never on the first date and never without being asked first. You pulled away from Obi for the first time that night.
“No, chickadee, I would have asked first. Why, do you want it on?” He reached out for your hand and held it, worried that he had overstepped his bounds.
You shook your head. “Maybe next time? I just wanted to make sure.” You laughed nervously and squeezed his hand.
“Next time?” Obi’s smirk returned. “I’ll have to be sure to leave you wanting more, then.” And with that, he abandoned your pussy entirely for the time being and finally revealed what was underneath his boxers.
He was big, bigger than you had imagined, and had girth to go with it. Your pussy, which was still recovering from your first orgasm, throbbed with anticipation once more, and this time it was you who pushed him back to lie on the bed. “My turn.”
Obi kept himself under control as you darted the tip of your tongue over the tip of his cock, up and down the shaft, but as soon as you finally took him in your mouth and began bobbing up and down, a moan much higher in pitch than you would have expected escaped his lips. “Yes, love, just like that, oh my—” He broke off into another moan as you began playing with his balls, still sucking his dick like the good little girl you tried so hard to be. You could tell from his breathing that he was already getting close, so you gave his cock one more perfunctory lick from base to tip, then readjusted yourself so you could straddle him.
He raised an eyebrow at this, clearly not expecting you to take charge, but said nothing. You guided his cock to your entrance, gathered up the natural lubricant that was still dripping from you, and sank down onto him, gasping at the size of him as you took every inch. Obi’s hands found your thighs yet again, clearly a favorite of his, and he caressed them as you moved on top of him.
You would never disclose this to any of your sex partners, but deep down you loved being on top, dominating the dominant, forcing them to look at your form as you controlled their pleasure. Obi-Wan was clearly enjoying himself, but it didn’t take him long to decide that this position was simply not enough for him. He grabbed your waist firmly, and without exiting you and almost without you realizing what was happening, he hooked a leg under yours and flipped you over. He leaned in close, and the smell of whiskey and your own cunt wafted towards you in an intoxicating cloud. He kissed you more passionately than you had been kissed in quite a while as he entered you again, this time with him fully in control. You grabbed his shoulders, digging your nails into his skin.
“You like that, love?”
You nodded your head, and he slammed into you harder than he had before, reaching the deepest parts of you that rarely saw action—unless you were home alone and had the assistance of one of the several toys that occupied the unassuming shoe box under your bed. The Pinky Doodle Thruster 9000 had nothing on Obi, however. His cock fit inside you so well, and every time he thrusted in or out, you came closer and closer to a second orgasm.
“Oh my god, Obi I’m gonna cum, don’t stop—” You moved your hips in rhythm with his as he pushed you over the edge and into an orgasm that you felt through your whole body. Your nails dug farther into the skin on his shoulders, but he didn’t seem to mind or even notice.
As soon as your body had processed the orgasm, Obi fully exited you, and by grabbing onto your waist flipped you over onto your stomach. You raised your ass in the air without being told; doggy style was one of your favorite positions. Obi teased your entrance, knowing how badly you wanted him and how badly he wanted you. Then, with a sharp slap to your ass, it was off to the races again. The only sounds in the room were your breaths, twisting together in lustful moans, and the clap of his body against yours with every thrust. It wasn’t long before you felt yet another orgasm building inside of you, and you reached down to pleasure your clit. You ran a finger over that little bundle of nerves, and kept stroking until the pleasure inside and outside of you burst like a dam, and you squirted all over his comforter.
“I’m sorry,” you gasped. Some men thought this was hot, others disgusting, and you hadn’t quite figured out which type Obi was yet.
“Do it again, chickadee.” His voice was gruff with arousal—he definitely thought this was hot. He had stopped thrusting when you came, but picked right back up, and it wasn’t long before you were able to follow his command.
The pleasure was becoming overwhelming, but you didn’t find yourself wishing for it to come to an end like you usually did after two or three orgasms. He gave you the chance to take a small breather and get repositioned, back onto your back this time.
“You’re so beautiful, chickadee,” he moaned as he entered you for the last time that night. “Cum for me one more time.” His hips moved against you hard and fast, and he held you tightly against him. Your walls tightened against his cock as you came hard enough for your back to arch and your eyes to roll back in your head. Unlike last time, he didn’t stop, but kept thrusting in full force, until finally it was his turn to grip you tightly, and let out a guttural moan as he came.
The gentle side of Obi came back out immediately. He gracefully slid out of you, spilling some of his cum out of your cunt and into the growing puddle on the comforter. He gave your forehead a little peck, then whispered, “I’ll be right back, chickadee.” He pushed himself off the bed, grunting as he did so, and walked out of your line of sight, presumably to the bathroom.
You were perfectly content to lay there, among the now rumpled comforter and the puddle of your mixed bodily fluids, trying to regain control over your breath and legs. Before you could muster the strength to move, Obi was back in your line of sight, but instead of whiskey he had a glass of water in one hand, and a terry cloth in the other.
“You’re welcome to take a shower,” he said, handing both items to you as you sat up. “I won’t kick you out if you’re too tired to go home, either.”
You thanked him, and agreed to both offers. Looking at the clock above the window, it was past 1am. By your calculations, you wouldn’t be home until well after 2:30. Obi-Wan seemed like a perfect gentleman; sleeping here for a night wouldn’t be the end of the world. And if it ended up being so, well, what a way to go out.
While you were in the shower, Obi snuck into the bathroom to lay out one of his T-shirts and a pair of basketball shorts for you to sleep in. This and a change of sheets were welcome surprises when you exited the bathroom. As you were laying in bed together, close but no longer touching, Obi said yet another surprising thing.
“This feels right somehow.”
You turned to face him. “Yeah, it does.”
“Will I get to see you again?” His eyes looked genuinely concerned, as if the thought of this only being a one-night stand would break his heart.
You smiled, and snuggled up to him so his beard was tickling your forehead. “I think you will.”
He kissed you in response, and you fell asleep in each other’s arms, both happy for the first time in a while.