I have so many of these bouncing around in my brain I figured Iâd write some down. These are all for cis, widower, single dad Bob. Might write out my hcâs for trans Bob at some point too. I was going to write some masc/ male specific headcanons too but ended up saving those for later bc I didnât have a lot. Pls ignore the shitpost image I thought the text was fitting.
^ stuff you hear mid-conversation with him ^
âGeneralâ
⢠A pretty observant guy, quiet in most conversations because he thinks before he talks, likes to speak fairly directly. Great listener.
^ Funny as hell because of this. Bob might not be quick to make a joke in conversation, but the jokes he does tell always land. Has a habit of making people laugh so hard they cry with just a few words. Fantastic at âyes, andâ-ing situations, lets other people build the joke a little before he adds that final touch that makes the whole thing so funny you canât help but laugh your ass off.
⢠A little hard to talk to at first, gruff but kind. The type of guy youâd be nervous to ask for help, but once you did heâd do it without expecting anything in return. If heâs had a bad day- good luck, that shell is a lot harder to crack, but not impossible.
⢠Easily won over by people who show theyâre equally as observant as he is. Figure out his favorite things just based off of passing comments he makes? Or better, without him ever having to tell you? Youâll make quick friends with him.
⢠Heâs either a good liar or a terrible liar depending on the situation. Tells them confidently and hopes no one notices. Unfortunately theyâre so bad sometimes they make everyone who hears them visibly cringe.
⢠Big reader, likes biographies and non-fiction books about far off countries and places he might like to visit someday. Wasnât big on reading until heâd met his wife, and she talked so much about the places sheâd like to go someday that he couldnât help but get interested too.
⢠Also, really good at reading aloud. He and his wife used to sit and read to Ingrid before she went to bed. After she died he fell out of the habit, both of them unable to bear the thought of reading without her. Ingrid asked him for a bedtime story a couple months later and of course he read her one, wouldnât deny her that. But stepped out of the trailer once she was asleep and bawled his eyes out the minute he was out of earshot. Made it a habit to read to her every night after that.
⢠Fantastic storyteller, goes big with his stories without making them unbelievably big. When he does tell personal stories the cause of the trouble/ butt of the joke is usually him, not in a self-deprecating way but in a âoh man that was so stupid of me to doâ way that makes you both laugh.
⢠Is not picky about his cigarettes, nor his alcohol, which has made it very difficult to quit either. Heâs tried multiple times but canât fully commit to doing it without help.
⢠Like all good people, desires to someday be behind the wheel of an automobile. (Specifically the â06 Ford Model N)
⢠Seen by the other carnies as a guy whoâs not trying his best but is trying to make the best of a bad situation. Most of them make a mild effort to keep an eye on Ingrid when they know he canât.
⢠Bob is fairly protective of his daughter, especially because they move towns so much. Does get a little paranoid right after his wife dies about something happening to Ingrid too, but as time goes on he relaxes. Very much a "what would my wife do" kind of guy.
âDating/ Relationshipâ
⢠Would like to take things slowly depending on how long heâs known you. If youâve known him for a while heâll probably be more comfortable with the idea of dating as opposed to someone whoâs just visiting the carnival. (Though I don't think he's opposed to the idea of quick flings if you're just visiting)
⢠Because heâs observant, he will get to know the things you like fairly quickly. If youâre already traveling with the carnival youâll find little things waiting on the top step of your trailer occasionally. Flowers you like, books he thinks you might enjoy, things your eyes lingered on a little too long the last time you all went shopping.
⢠Part of his love language is doing things with you. Walking through the towns you visit, grocery store trips, making dinner together, everything and anything in between. Big on experiencing things alongside you, pointing things out that you otherwise might not have noticed, enjoying when you do the same for him.
⢠Absolute sucker for a good massage. His act involves a lot of repetition, and most of it really takes a toll on his mid and lower back. If youâre kind enough to pop/ rub his back after a long day heâll give you everything you could ever ask for and more.
⢠Will leave red greasepaint kisses on your mirror if left unattended in your trailer. Robert will not admit to, apologize, or offer to clean them off, but only because he knows you like them.
^ Most of the time theyâre in the corners and out of the way so it doesnât impact the function of the mirror. But sometimes, if you leave him for long enough, heâll take the time and leave them in spots on the mirror that line up with your body. That way, when you stand in front of the mirror, youâve got kiss marks on your cheeks, neck, anywhere he feels like you need them.
⢠Sleeps like a rock, and likes to fall asleep cuddling/ in some way touching you. He wonât ever ask for it out of sheer embarrassment, but he adores being the little spoon. Bob also really enjoys when you run your fingers through his hair.
^ Snores. Loudly. RIP if he falls asleep on top of you because heâs surprisingly heavy and difficult to move when heâs asleep (unfortunately itâs because heâs so damn tall thereâs so much more of him to move around). If you half wake him up and ask him to move off of you, thereâs a good chance he will think youâre joking, laugh, and fall right back asleep.
⢠Very comfortable showing physical affection with you, wants it to be known that you are his and that youâre loved.
These are all for cis, widower, single dad Bob; though that doesnât matter as much for this post as it did the last. Again ignore the shitpost I thought it was funny lmao
v NSFW under the cut v
⢠Average length, a little on the thicker side but not enough to make it uncomfortable, uncut, next question
⢠Gentleman on the streets, gentleman (and loverboy) in the sheets. Really gets off on getting you off and takes pride in the fact that heâs making you feel this good. Prefers to have you in a position that allows him to see your face so he can kiss you and watch you fall apart for him. Missionary/ cowgirl are his favorites.
⢠Huge on praise, absolutely loves telling you what a good job youâre doing regardless of whether or not youâre actively doing anything. In turn also loves to be praised.
⢠Enjoys teasing you with little touches and comments throughout the day until neither of you can keep your hands off each other. Pulling you behind buildings after shows to kiss you silly, ghosting his fingers along your neck and down your back just to make you shiver, walking up behind you and pressing his body flush to yours so he can better kiss your neck, sneaking his fingers up and under the hem of your shirt just to feel your skin against his. Anything to hear the flustered little noises he can get out of you. Really likes to get you worked up so youâre thinking about him all day.
^ Would love it if you did the same to him.
⢠Likes to check in on you, make sure heâs not being too rough (even if you tell him you want him to be a little rougher), doesnât enjoy the thought of hurting you.
^ If you do want him to be rougher, he's very good at being just rough enough that you'll feel him for days after. Wants you to feel the space he's carved in you for himself and get worked up just thinking about it.
⢠Very doting during aftercare and appreciates if you are in return. Heâll spoil you with kisses and help clean you up before pulling you close and massaging any sore spots you might have.
⢠I mentioned in the sfw headcanons that heâll leave red greasepaint kisses on your mirror so when you stand and look at your reflection youâll have kisses on your cheeks and lips. Absolutely will leave kisses lower on the glass to mark your neck all the way down to your hips if heâs feeling suggestive. Will not apologize, admit to, or offer to clean those off either.
^ If the two of you ended up fucking in front of the mirror he might have a little fun with it and leave red kisses in the same spot on your body either as foreplay or during aftercare.
⢠You live busy lives, itâs inevitable you will fuck in the Pennywise outfit at least once. Whether itâs intentional or not, itâs going to happen. If thatâs something youâre really into (who among us wouldnât be), he thinks itâs very endearing once he figures it out and will go out of his way to make it happen more often.
^ Fun little bonus: if youâre the one fucking him and his makeup gets messed up he will ask you to fix it. Tells you itâs only fair even though you made him cum so hard heâs having trouble standing.
⢠Is much more comfortable being the one doing the penetrating and would be pretty hesitant if you asked to switch positions. Wonât outright tell you no, but there would need to be quite a bit of trust between the two of you before heâd agree to trying it. Bob will try it, though, and does end up enjoying it once he does. Might take him a while to work up to actual penetrative sex, so expect a couple sessions of fingering before anything bigger gets involved. If you do end up using a strap for whatever reason, he will treat it like you can feel it.
^ He does not, however, have any issue with you fucking his thighs, so feel free.
⢠A switch, usually takes the lead in bed but is happy to let you have control if you so much as hint you want it.
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A/N: Might write out my hcâs for trans Bob at some point too. I was going to write some masc/ male specific reader headcanons too but ended up saving those for later bc I didnât have a lot. Anyway Iâm working on those and the next chapter love yâall see u later đ¤
We can all agree that Antony Starr was the highlight of whole show and he gave this show his absolute everything. His performance from season 1 to 5 was spectacular
this is because they write with their mind penis and have terrible childhoods and horrible luck, which seems to be the key factor in writing shakespeare level smut
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