Work Text:
You stand nervously at his office door the case files clutched to your chest. John had never asked you to come back to work on his cases in the evening and honestly, you hoped he had an ulterior motive. You certainly would if you had invited your devastatingly handsome boss to stay after business hours. Then again it was probably a good thing your date canceled for tonight because you would have canceled to help John anyway. You’d been working as John Winchester’s secretary for nearly two years. It was hard work but enjoyable and John was respectful and one of the hardest working men you knew. You’d fallen for him fast and even though you told yourself as your boss it could never happen it didn’t stop the fantasies you entertained.
Adjusting the case files you knocked on the large wooden door taking deep breaths as it swung open. You swallowed looking over John his tie undone, his hair looking teased from where his large hands had probably run through it, and surprisingly he was barefooted. Although half his office did look like an apartment. John didn’t believe in treating everything like a business so instead of a conference table, he had put in a large couch opposite from where his desk sat. It was a warm office and to be honest it worked people trusted him a lot and were always at ease.
“J, thank you so much for coming back. I’m useless without you and this stupid dinner Bobby made me go to, took too long,” he waved you in and you sat the file on his desk pulling out your laptop setting up shop to work. You watched as John moved to pour himself some of his whiskey and a second glass, “I know technically it’s work but may I tempt you?”
“I’m not one to ignore temptation,” you quip holding out your hand for the glass. He chuckles hand you the glass clinking his against yours. You keep your eyes on him swearing there is something else there but he sits down behind his desk and it’s all gone and business John is back.
An hour later you excuse yourself to go to the ladies’ room. You were nearly finished and frankly, you were ready to never type up another memo again. Something shifted once John got to work he seemed moody and twice he had snapped at you when you asked him about a note on the document you were working on. You had heard he snapped at people but this was a first for you. You wondered if you had done something wrong or messed up somewhere but at this point, you were too afraid to ask. Whatever it was you were ready to call it a night and go home enjoy a beer or two and sleep through the weekend.
John was sitting on the couch his elbows on his knees dangling another glass of whiskey in his hand. You said nothing as you returned to the chair in front of his desk and continued working on the last page of the report. John said nothing and you made no move to ask him anything else in fear that he would snap at you again.
“I’m sorry J. I’m really am,” his voice made you stop and you saved your progress turning to him surprised to find he was already behind you. He set the drink down taking your hand pulling you up to him. Your hands landed on his chest as you swallowed nervously looking up at him. “Tell me you don’t want this J. I can’t keep fighting it but if you don’t want it please tell me now.”
“John, shut up and kiss me,” you growl pulling him to you. His hands hook under your thighs and you jump wrapping your legs around him his arousal pressing into your core. He walks you back to the couch but when your feet reach the ground you push him back onto the couch. He looks stunned as you slowly slip out of your skirt and pull your shirt off.
“Jesus,” he gasps. “You always wear stockings and garters?”
You blush looking down, “No I had a date tonight actually but he canceled this morning.”
“Whoever he is he’s an idiot,” John lips his lips standing up his hand brushing your stomach as he moves behind you kissing along your neck and shoulder. His hands undo the clasps of your bra and you slide the bra off. John’s hands slowly caress your sides lighting a fire along your hips where they rest.
“You are so beautiful J,” he spins you around retaking your mouth in a heated kiss. His hands twist into your hair while you work on the belt of his pants. He stands back sliding out of his pants and your eyes widen at the tent of his pants. “Lay down on the couch J.”
“Yes sir,” you lay back as he pushes his pants off and begins unbuttoning his shirt. John may be older than you but he’s in great shape and is definitely gifted below the belt. He settles on the edge of the couch spreading your legs as he leans forward resting over you trailing kisses down your chest his tongue swirling over each nipple, “John, fuck.”
He chuckles against your stomach and kisses along your hips, “You attached to these panties, sweetheart?”
“No, why?”
John answered by ripping your panties and burying his face into your core. His tongue working you into a frenzy as you grabbed his hair pressing your core into his tongue as he licked and sucked at your lips. His thumb came down on your clit unexpectedly and you screamed out as your orgasm washed over you bringing tears to your eyes as John sits up, “You with me J?”
“I don’t think I’ve ever cum that fast before,” you laughed leaning up to take his cock in hand. You pumped him a few times before he stopped you, “What’s wrong?”
“This is about you J. Lay back again. I want to feel you wrapped around me,” John orders and you moe without argument. He picks up one leg resting it on his shoulder and the other around his waist as his cock head teases at your pussy, “You are so fucking wet for me J. Hold on baby girl.”
John teases you while you clutch the pillow and backseat cushion allowing him to slowly press into you. You can feel his girth as he fills you amongst your own whimpers and small moans his heated growls adding to your arousal. Once he is fully seated inside you he slows kissing along your calf and ankle murmuring words you can’t hear through your lust filled mind. Part of you can’t believe this is happening but when you look up at him you are so thankful it is, “John, please, move, please move!”
“Hold on J,” he flashes you a smile before he begins moving his hips forcing himself in and out of you. He somehow manages to hit every sweet spot you have as you moan and writhe against him. He increases his pace and you grip tighter as you moan calling out for him, “God why did I wait so long? You are so beautiful all stretched out like this for me.”
“Yes, sir, all for you. God feels so good,” you moan then cry as he pulls all the way out. “No sir, please.”
“Get on your hands and knees J,” he stands fisting his cock and you quickly turn to get into position as he wants. “Fucking beautiful,” he whispers slowly re-entering you. His hand rests on your hip and his pace this way is slower but no less pleasurable. He drags his cock in and out of you making you moan and bite your lip against the feeling.
“God John,” you practically sob as he pulls you up against his chest using his hands to caress your breasts while still thrusting into you. “Sir, please let me cum. I need to so bad.”
“Hold on J. I want to watch you come apart,” John pulls away sitting back onto the couch helping you climb onto his lap. He holds his cock as you slowly sink down onto him your eyes closed in ecstasy. “Ride me J. Make yourself cum,” John orders. You can’t deny him as you begin moving up and down his cock his hands moving back to your breasts.
“John, I’m so close,” you whimper feeling the warmth build in your body begging for release. “Sir, please.”
“I got you beautiful,” one hand remains on your breast but the other trails down his fingers finding your clit. “Cum for me and I’ll cum for you.”
“Yes, please, inside me, John. Please cum inside me,” you gasp moving faster as you feel your climax grow closer. “Please, sir!”
“Fuck,” John growls and you feel his cock tighten and suddenly he cries out and you feel him coming. He increases his work on your clit and seals the deal taking a nipple into your mouth when you grasp his biceps your orgasm hitting you hard making you scream his name. “That’s my girl. That’s my J!”
You slump against him kissing his neck lazily feeling him still twitch inside you. You panic momentarily realizing he didn’t wear a condom, but it’s too late now. Hopefully, your medicine works. His hands move soothingly up and down your back when he helps you lay down on the couch letting his now soft cock slip out. You cringe at the feeling of your joined spendings drip from your hole but John is transfixed but it watching with delight before standing pulling his pants back on. You throw your arm over your eyes with a sigh waiting for John to make the next move.
“Don’t fall asleep on me yet J,” John settles next to you. He takes out a cloth and spreads your legs cleaning you. “Do you want to take these stockings off? I can’t imagine it’s still comfortable no matter how gorgeous you look in it.”
“Yeah mind helping me, sir,” you tease and he leans forward kissing you before helping you out of the garters and the stockings. He hands you his shirt and you button it enough to cover you as you sit up. “So what now?”
“Well, it’s almost ten o’clock on a Friday evening and I thought I might persuade you to join me for a late dinner. Then if you are free the weekend we can spend it in my bed at my condo.”
You smile with a nod before looking up at him nervously, “So this wasn’t just a one-time thing?”
“J, do I look like a stupid man?” you shake your head and he chuckles pulling you onto his lap. “Well, as long as we can behave ourselves on the clock then yes this is a more than one-time thing. I’d like to date you, to be honest.”
“Are you serious?”
“I thought me fucking you in my office was pretty damn serious. It’s why I was kind of snappy earlier. This work we did could have waited until Monday but I just wanted an excuse to see you. I didn’t plan for this to happen but God I’m so glad it did. I’ve been smitten with you since I hired you.”
“Seriously, me?” you question and he frowns.
“Yes, you J. Now will you please have dinner with me?”
“I’d really like that John,” you answer taking your chance to kiss him again. He leans into it but breaks it off pressing his forehead to yours before it becomes too heated. After a moment of silence, you both stood quickly dressing and you allowed him to lead you out of the room to the elevator. He held your hand the entire way even in the car to his condo. Once inside the late dinner turned into you finally getting to feel his cock in your mouth and him seeing how many times you could come apart on his tongue.
“J, you comfortable?” John asks as you snuggle closer against him your head resting on his chest as your fingers twirl in his chest hair.
“Never felt better,” you sigh. “Are you comfortable?”
“Never felt better. Goodnight J,” John kissed your forehead as you mumbled back before you both slowly fell into a deep sleep. Neither one of you realizing this was the beginning of a very happy ever after.