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AU where Jack is a paper boy, he delivers papers on his route and when he has to drop off newspaper at a certain house, the owner is always flirting with him. It’s Benny and Benny is always gives him a tip while saying so many sexual Comments towards Jack. One time Jack nearly drops his whole bag of papers when Benny sneaks up behind him and slaps his ass while Jack was putting the paper on the door step.
OH, FUCK.
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Hi, princess!👑💕 I hope you had a good day and you're fine! I always try to find the perfect partner for Jack. So I always think about which of our supernatural-boys would be the perfect lover for the cute Jack. Maybe Gabriel? I dont know. I never really get a result for myself. Do you have any other suggestions and ideas for me? Many warm hugs and I love you!💖💞
Hey there, beautiful! 💋 My day is SO much better now that I've heard from you! I hope you are having a great week and that you're doing well, my darling. 💕💕
As for your question, I have SO many suggestions for you. I ship that adorable angel with pretty much everyone.
I'd have to say that Dean is my preferred choice though. He's (my favorite) Daddy af and baby boy needs that dominant, I'm gonna make you cry for all the right reasons energy in his life. 👌 I'm here for bratty Jack getting his guts rearrange by Dean who has his hand over the kid's mouth to stop him from talking back, voice low and gritty when he whispers in Jack's ear, "Shut up and take it, slut." 🔥
That being said, I also LOVE him with Sam. 💕 They are so soft together and I just want Sammy to give Jack all the eskimo kisses and tight hugs baby boy deserves. Oh, and to eat Jack out until he's a sweaty, babbling mess and the only words that he can remember are "Sam" and "please". 👌
Ah! I can totally dig him with Gabriel too! I feel like he'd make Jack laugh and give him soft neck kisses that would have baby boy weak in the knees. (Also, I can totally see Gabe exploring his food kink with Jack. Like blind folding his adorable little nephilim and having him taste all sorts of sugary foods like chocolate covered strawberries, whipped cream, caramel sauce and anything else he could think of that left Jack all sticky and made that curious pink tongue of his work so hard to taste the sweetness on Gabe's fingers.)
God, and don't even get me started on the deliciously filthy potential of Jack and Benny. Just the size difference alone. END ME. Ugh! Baby boy's thighs would stay sore from the beard burn and he'd love every minute of it. Yep, definitely want that bear to destroy everyone's favorite blue eyed blonde twink. Please and thank you. 🙏
And of course, as you saw from my post the other night, I'm DOWN with Jack and John Winchester. 👌
Also totally game for:
Jack/Adam (Need some twink on twink action every now and then. 🤙)
Jack/Young John (Because the mental image of Alex licking Matt's flawless fucking abs is A++)
Jack/Lucifer (Y'all know why, judge me not!)
Jack/Balthazar (Because I'm trash!)
Jack/Gordon (Okay, but like b r o. Gordon leaves baby boy all bruised and fucked up and begging for more just so he can send him back to Sam. Jack gets wrecked AND he gets angry, protective, I'll kill him for putting his hands on you Sammy? *chef's kiss*)
Honestly, as long as Jack is getting fucked within an inch of his life then
(P.S. I know you said boys but I'm hella into the idea of Jack/Meg 2.0 and how dirtybadwrong Jack would feel when her eyes flashed black as she fucked him hard. (With the biggest strap he could take.) 🥵
ANYWHO. Sorry for this word vomit, my lovely. I guess in conclusion my answer is, anyone with a pulse. Lmfao
Sending good vibes and lots of warm hugs your way! I love you too! 💕💕
Benny taking jack to a bar to show him a good time and eventually Benny takes him to the bathroom to rim him over the sink and fuck him, telling jack how other men in the bar were eyeing him and how good jack would look taking all those men like a whore.
It’s just dirty talk, of course - as if Benny would let anyone else lay hand on his beautiful, obedient boy.
Coming back from the dead was worth it just for this kid.
;)
what d’ya wanna write about? We haven’t talked about Benny in a while, if you’re thinking about ways Jack can finally have some fun
“Well, aren’t you cute as a button?” Benny drawls, dragging his eyes down Jack’s body.
Jack flushes, biting his lip hard. “D-Dean must be so happy you’re back. He talks about you a lot.”
“Don’t go changin’ the subject now, sugar,” he murmurs, coming closer. “I want to talk about you. ‘Cause I noticed that you haven’t been able to keep your eyes off me ever since I stepped foot in here.”
“Maybe I’m making sure you don’t bite me,” Jack shoots back, his body tingling with anticipation.
“Oh, but you’d love to be bitten, wouldn’t you? Such a sweet, virgin boy.” Benny grins, his teeth glinting in the light. “I could show you a good time, you know.”
“How do you know I’m a virgin?” Jack asks, shivering.
“Got that look about you. The - you know - ‘not yet entirely ruined’ look.” Benny’s pressing him against the wall now, covering Jack’s small body with his big one. “What do you say? How about I help you relax?”
“I - I don’t know. I don’t know you. And -”
“Is sex really important to you?”
“I mean - a little, yeah.” He squirms. “Sam and Dean both told me that, um - it’s a completely okay thing to do, and that I should just make sure I’m ready or want it.”
Benny strokes his cheek. “Well - no pressure, then, cher.” He grins, pecking his forehead. “You just let me know, huh?”
About Benny and Jack- when they get down to it, Jack on his hands and knees, Benny behind him, Jack is the one to guide Benny's big cock inside. Inch by inch, totally in control until he's comfortable enough to let Benny thrust on his own. Comfortable enough to climb on top and ride the vampire at his own pace, head thrown back in pleasure.
F u c k.
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Benny stretching out jack’s hole with his fingers and tongue, he’s had a long day and needs to take it out on jack’s cute ass.
God. I SHIP IT.
Jack is a cute little twink with a size kink a mile wide. In walks Benny & Jack's drooling just from looking at those long, thick fingers. They'd stretch him out so good. And that cock... Jack knows it'd rearrange his insides & make his belly bulge. He's desperate to be under this mountain of a man, split open as he's filled so full he can't hold it all. And when Benny calls him, "cher," one hand heavy around his throat, Jack cums so hard he almost passes out, begging him for more.
YES.
Destroy him, Benny!
Benny playing and teasing jack’s cute little hole until he begs real pretty. He just rubs it and presses his fingers lightly against, making jack almost go crazy.
Fuck - Jack loves it so much; acts like such a little slut for it.
