#responded on an actual wednesday (in some timezones at least)

[dyed-red]

Happy WW! What do you think about Sam’s and Dean’s safe sex practices? Do they use condoms with each other? Do they *talk* about it? Have they ever been cavalier with strangers? What about Robo!Sam and Demon!Dean?

you sent this like 3 weeks ago, i started replying, got distracted by work, went to a conference, got covid, finished teaching for the term, and now we're back!

(sorry about the delay omg, and thank you for asking!! i love asks! i'm just distractable af with replying)

Happy Wincest Wednesday!

Okay I definitely had to think about this one and separate what i like to write or think is hot (no condoms, nothing between them and marking each other with cum) versus what i think actually suits their characters.

Starting with how they are with other people (because I don't headcanon them as especially monogamous in their relationship with each other, especially dean), I headcanon that they both have fairly careful safe sex practices -- once again, especially dean.

he wasn't entirely shocked by the idea that he might have a kid running around out there when he met Ben, so i think sometimes something slips (condoms aren't fool proof, and whatever he and lisa were up to sounded bendy and memorable so maaayyybe he was skipping the safety just a little, he was still pretty young when he would have had that memorable time with her, i think 19?). but i also think he's really damn careful because he knows that if he had a kid, that would consume his life in a huge way. family is everything to dean and given his lifestyle and the fact that sam's safety (or continued survival and humanity, at least) is typically his #1 priority, i imagine the thought of getting someone pregnant would terrify dean as much as he might also want that, on some level.

sam, i imagine, is incredibly practical about these things, which means careful safe sex and condom usage. at the same time, sam is undeniably kinky, and if we assume he has as big a dick as is typically headcanoned and at times implied (by jared and by that ridiculous dick joke of a promo with swords), i also think sam wouldn't really... like condoms. (i mean, does anyone?). getting the right size feels almost egotistical, and he might be really particular about ordering from a select brand or something. i also think he'd definitely get off on not using one, on being bare with his lover and finishing inside them and the fear/danger/possibility of that as well as him leaning into the possessive and territorial side of marking someone. sam is a jealous guy, even if it tries to paint himself as cool headed.

so - i think sam is practical but also... reckless. he's canonically got a blindspot for his own reckleness, because once he's decided something is a calculated risk, he's 110% in. driving the impala through the side of a house? check. turn into a zombie with dean to loophole dean's deal? check. sam dgaf, and i have to imagine he takes calculated risks with sex too.

so condoms are assumed, but with a long term partner (jess), once they're exclusive and she's on the pill (or patch or iud or whatever), he's seeing if condoms can exit the equation.

even more casually though, he's not hard to convince to just... skip it. the girl says she's clean and on the pill (or whichever)? sure, yes, great, no condom needed. maybe not for the more incidental of hookups, but he also prefers to get to know his partners, even his hookups, at least a little before sliding into bed with them, which i think would also lend him more confidence in what they're claiming about their birth control and sti status.

(he's also had the clap courtesy of that joke from Patrick the witch, if i remember the episode correctly, so like... there's that. tbh i headcanoon that both sam and dean have both had stis at least once, dean because condoms aren't 100% perfect in mitigating sti risk and he really enjoys hooking up, so it's just a numbers game. and sam because he's not as careful as he likes to think he is)

for demon!dean, he's using condoms. he does not want to have to deal with any of that shit. if demons can get pregnant and carry the antichrist (as per season 5), they can sure as shit get others pregnant, and that is a headache and a half. he might not bother when he's hooking up with crowley and twins or triplets and things are getting wild, because it's not like he can get an sti this way (the same way demons can't really get human injuries, right?), but i also tend to think dean is... not a germophobe, not actually, but there's a limit to what other people's body fluids he wants on or in him or wants to have to deal with in general, and condoms are just easier, including and especially when doing anal (regardless of the gender of his partner).

for soulless!sam... that man gives zero shits. you want him to wear one? cool. you're cool with him not wearing one? no likely issues or infections? great, condoms are a nuisance anyway. if you get pregnant he'll pay for the abortion. he doesn't need a brat walking around but he's not above shooting you if it becomes a headache. if you show up with a kid, he also might decide that's cool and he has a little mini me to train up, since having a hunting partner is preferable than not, especially if he can mould them into a useful tool.

now the most interesting part... what does that mean about their safe sex practices with each other?

(under a cut because this got long and ever so slightly filthy)

depending on how they start hooking up and the trajectory here, i can envision that when they get to the penetrative stuff (regardless of who tops and who bottoms), dean being confused and a little... affronted? that sam wants to do it without condoms?

"what do you mean you like it better that way? you're doing this with other people? you're skipping condoms? what the hell is wrong with you, did you learn nothing from the safe sex talk when you were 14?? that talk was 98% about no glove no love! where did i go wrong? aren't you worried about diseases? about kids? sam what the fuck?"

i jest but like... this is sending dean, a bit. sam is the responsible one, what the fuck is happening here. sam, unless he's pissed about dean being over the top, would just shrug and say condoms numb some of the sensation. poor dean is stuck between the reality of sam's stupid big dick and the perfect responsible sammy image he has in his mind cracking into a million pieces.

(not like he didn't know sam is a freak in bed but that's one thing and this is another. but well, sam has literally drank blood, what's a few other bodily fluids in the mix after that? but dean doesn't want to think about that. and sam reassures him that he gets tested regularly for stis when he's sexually active, regardless of whether he's using condoms or not, because he is diligent and responsible in his own way)

anyway, they come around on it, both willing to try it the other guy's way and accomodate. assuming they're both vers, which is my headcanon on their dynamic, they fall into a pattern where whoever bottoms essentially determines what safe sex practices are gonna be used that day.

when sam bottoms, except when things are quick or sleepy and he doesn't want to deal with any prior or post cleaning, he typically prefers when dean skips the condom because it turns him on when there's nothing between him and his brother, and dean gets into that as well and gets a bit kinky with it, with having all of his brother and leaving some of himself in sam's guts. sam eats his fibre and this doesn't present either of them much issue.

when dean bottoms, he generally makes sam glove up, but there are plenty of exceptions. one of the things he enjoys about it is that sam will go a little caveman and pull out to cum, pulling off the condom and cumming on dean's skin instead, whether that's on his back and ass and on his hole (dean doesn't mind, kind of likes when sam rubs it in there a little, with his dick or his fingers, but he's not about to admit that out loud), or whether it's all over his stomach, or if sam is in a Mood and he grabs dean by his short hair and cums on his face.

(which is another thing that turns dean on like whoa, but only when sam does it, he hates taking it on the face from anyone else. and it's half because of how sam looks when he does, and looks at dean, and there's so much heat and possessiveness in the action that it slides down dean's spine, the naked reality of just how much sam wants him, how he can't hold back or hold himself in check, how he wants devour dean just as assuredly as dean wants to devour him).

when sam is needy or jealous though, or when they have a bit of time, dean invites him in without a condom and and and - and he feels a little deranged and unhinged with sam all the way in there with nothing in the way, and it's really fucking good just skin on skin (better, he's willing to admit, even if it's not worth the added effort all the time), and sam invariably cums first when they do it that way and sometimes dean trips over that edge with him because sam hammers in so fast and deep when he does and because knowing sam is spilling inside of him scrambles something in his brain.

other times though, sam pulls out and goes down on dean and fingers his cum back in there and dean feels absolutely filthy and almost embarrassed and exposed and it's an entirely different kind of orgasm. almost always leading to cuddling that they don't discuss because things are a little raw when it plays out this way, for reasons neither can quite articulate.