Work Text:
If you had become a teacher you would already be home in bed, probably asleep, but instead you had to become a lawyer and lived in in the D.A.'s office, never sleeping, drinking too much coffee, and being buried in paperwork. This case was wrecking you, you wanted to cry but were too tired to bother, you felt like an overtired toddler.
Pushing yourself up you shuffled to Jack's office to say you were going home, but Jack was passed out on his couch. Better for you, he couldn't say anything about you leaving. He did look cute sprawled out and exhausted though, it wasn't like people in this building didn't all date or fuck each other, it could be in the realm of possibility. And you were too busy to even think about dating or having a friend with benefits since you barely saw your friends anyway.
"What are you doing?" Jack asked, you had been standing and staring at him thinking about how horny and tired you were. "I'm going home," you rushed out embarrassed at yourself, it was because you were tired you weren't normally this weird and horny, it was just the long hours and being in the same vicinity as the same guy day and night. Totally understandable.
"Good morning," You waved to everyone on the way to your desk, you let yourself into Jack's office, "Hey good morning, what time did you go home last night?" "Just after you finished staring at me," he passed you a stack of papers, "I need you to go over these and go talk to that witness." "Yeah sure thing."
Back at your desk you were looking at the documents but not actually reading them, you were so horny but also embarrassed with yourself, it had been probably 15 months since you last did anything. This weekend you would get out and do something, so you wouldn't be such a weirdo at work.
Friday evening finally rolled around, and you could not be happier to be free of this place for the weekend. You stopped by Jack's office on your way out, "Hey I'm heading out now." Jack looked up from his desk, "Any plans for the weekend?" You shrugged, "I'm thinking of going out, maybe going on a date." Jack laughed, "It shouldn't be too hard for you to find a date." You laughed sitting down, "It's way harder than you think it is, but then again I haven't bothered in trying for over a year." "Well I'll save you the trouble, I'm heading out too. Let's go get something to eat." Not exactly the kind of date you were looking for but whatever you have to start somewhere.
"So you haven't been on a date in a year?" Jack questioned, "You're a pretty girl it shouldn't be too hard to find a willing guy." You sighed, "I don't know I had a boyfriend in law school but he went to Chicago and I stayed here so I just haven't felt like it." "So if it's not a boyfriend why are you so distracted at work?" You blushed sipping your water, "I guess it's just been a long time." Finally the food was here, you could eat half your pad thai, say you were tired and run home, plus leftovers. "Why are we focusing on me, you never have a date either." "But I don't let my lack of dating get in the way of my work." He had a point, "What's really going on, I need you to use your mind for something other than sex." You might as well be honest it wasn't like you didn't spend all day every day with the man anyway, "I mean it's embarrassing but I'm just pent up, haven't had sex since my breakup like a year ago and haven't dated anyone since," your ramble trailed off, the awkwardness setting in. Jack laughed, "Does that have anything to do with you standing over me the other night? Anything interesting going on in there?" he tapped his head.
You shrugged, "Maybe," maybe he was also pent up and horny? "Why? Does it interest you?" He shrugged back at you, "I wouldn't be mad if you showed me what was on your mind." "I live a 20 minutes walk from here if you're really that interested in finding out." Jack signaled the waiter to bring the bill, "You lead the way."
The two of you walk quietly, arms linked, as you lead him towards your apartment. Maybe it was a mistake, you were nervous but tingling all over at the idea of fucking Jack. Reaching your apartment you pushed the door open leading Jack up the stairs, "Sorry there's no elevator, but luckily I'm only on the 4th floor." You had become more anxious climbing the stairs, once inside Jack closed the door as you stood awkwardly before him. "You know we don't have to do anything you don't want to." "No!" you rushed out, stepping closer, "I would be this nervous no matter who I was with with." Brushing your hair back, Jack kissed your cheek, "Whatever you want."
Jack had stripped you down to nothing and spread you out on your bed, gently easing a finger into you, "Oh you weren't lying about it being a long time for you." You whined softly as he nibbled your inner thigh and dragged his tongue over your clit, pumping his finger while running his fingertips over your stomach. You're so overwhelmed it had been so long, you trembled when he added a second finger. Grinding your hips against Jack's face you needed more, running your hands through his hair, "Oh fuck!" He curled his fingers hitting such a good spot inside you, his tongue was so soft, it all felt too good you couldn't do anything but lay there, hips twitching in pleasure, and let him lick and suck your swollen clit. Your lower belly was tingling, a tight feeling building there, you grabbed at his hair as the tightness in your belly burst. Your orgasm washes over you, leaving you whimpering in pleasure as Jack laps at you, loving your taste.
"Get up," Jack instructs, undoing his pants as you scramble to kneel in front of him. You're so desperate to please him, you're aching for him, eagerly waiting for him to tell you what to do, "Open up baby." You gasp at how big he is, you lick up the underside of his taking him in your hand as you suck at his leaking tip. He groans pulling all your hair back admiring how pretty you look with his dick in your mouth. You suck him deeper stroking what you can't fit in your mouth, he shudders when you take his balls in your hand gently massaging as you suck and stroke him.
Jack can feel his balls tightening, your warm wet mouth and soft hands pushing him over towards the edge. He moaned pulling you off him, "Come up here." You practically jumped up, kissing and pulling him onto you, wrapping yourself around him. Jack lined himself up with you, slowly pushing in, you gasped feeling the stretch of his dick. Jack pressing kisses into your cheek to distract you from the almost painful stretch of him until he bottomed out. "Shhh sweetie I've got you." He whispered trying to calm you as you whined and twitched under him. It felt like he was in your stomach, it had been so long since anyone had been inside you, it was almost overwhelming but you wanted him to move so badly, "Please Jack, move."
He huffed, pulling halfway out before pushing slowly back in testing the waters. You moaned grinding back into him, you were so warm and tight Jack set a slow pace pulling you into him by the hips so you could grind your clit against him. Jack groans barely pulling out, your grinding on his dick feels so good, you squeeze him rolling your hips down until you burst, warmth spreading through your body as your orgasm hits. You squeeze Jack's dick, your pussy gushing as he continues fucking you, now chasing his own orgasm, happy to listen to your soft sighs and moans encouraging him to finish inside you. He feels his balls tighten his orgasm on the tip of his tongue, you kiss and lick into his mouth running your nails up and down his back, begging him to keep going. You push him over the edge, his cum bursting into you in bursts, he moans into your neck hugging you tighter to him as he rides out his orgasm. "You're so sweet," Jack whispers kissing your hair, you hum happily the tiredness setting into your body as you rub his back letting him rest on top of you for a while.
Your shower had been a little tight fitting both of you in there but surprisingly Jack was still in your apartment with no signs of leaving. You looked into your room from the kitchen, Jack was dozing off in your bed. Honestly you were a little shocked he hadn't gone home by now not that you minded in fact you were happy he stayed. Crawling under the covers Jack pulled you into him, kissing you goodnight.