Supernatural Smut Oneshots

Waiter/JackxStranger!Sam

Sam is 18 in this and doesn't have the kind of relationship he does with Jack in the show. In this essentially everything is the same with Jack, but he's being raised by Dean and Cas who are together. Jack is also older than he was in the show so he's much more mature. You also may be able to tell I took a little from the diner scene in S12E12

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Dean and Cas have been taking care of Jack for a few years now, the Nephilim slowly coming into his own in the world. Now he's starting to show interest in men and women, constantly asking Dean questions he doesn't want to answer. For example the time he called Dean and said he's going to need to know everything about sex. Since his dads are two men that are together, he feels like that's the default and his questions usually go towards what it's like being with other men.

When Dean has had enough of answering these questions and feels he's taught Jack as much as he can without actually demonstrating for him, he decides he'll pass this job off to someone else. Anyone else. He takes Jack and Cas into town for the day, hoping to find someone for Jack to pick up.

They go to a diner to eat first and once they've sat down Dean starts to explain his thoughts to Jack and Cas. "I've decided since you're showing so much interest in boys and girls that we're gonna help you pick someone up," Dean says.

Jack and Cas both do the head-tilty-squinty-confusion-face. "Pick someone up? Why would I need help to do that? I'm very strong," Jack says.

"It means finding a boy or girl that you think is cute and convincing them to let you take them home or out so you can.. well do all that stuff you've been asking about with them," Dean says. The topic of sex usually doesn't make him uncomfortable, but when it comes to Jack it does, so he had trouble getting the words out.

"So like asking someone on a date so that you can have intercourse with them?" Jack asks.

"Yeah, but don't call it intercourse when you're on the date," Dean says.

"Dean are you sure this is a good idea? I mean he doesn't know what to do, what if we send him off with the wrong person?" Cas asks shifting in the booth uncomfortably.

"We'll just pick someone who seems experienced, but not too experienced. Someone that looks around his age...well the age he looks like," Dean says. Cas looks uneasy at Dean, but allows him because he trusts his boyfriend.

"Hello, I'm Sam. What can I get you gentlemen to drink?" they're interrupted in their conversation by a waiter coming to their booth. Dean smiles when he looks up at the waiter, oh this is perfect.

"Coke for me, water for him and what do you want Jack?" Dean says.

"Do you guys have smoothies?" Jack asks, missing Mrs. Butters smoothies despite their poisonous nature.

"Yeah, the flavors are right here," Sam leans in to point at a section of Jack's menu. Jack notices that the boy is very beautiful and finds himself having a hard time not looking at his eyes. Sam blushes and steps back.

Jack glances at the menu, "Mango please." Sam nods and heads off to get their drinks.

"What do you think of him Jack?" Dean asks.

"Huh? Oh, well he's very beautiful and he seems sweet," Jack says, not even considering their previous conversation, but simply voicing his honest thoughts.

"You should try and pick him up," Dean says.

"You don't even know he likes guys," Cas says.

"That twink? Oh he definitely likes guys. It's in his body language, his voice, he has painted nails for Chuck's sake," Dean says.