✨Welcome To Hell✨

• A little hard to talk to at first, gruff but kind. The type of guy you’d be nervous to ask for help, but once you did he’d do it without expecting anything in return. If he’s had a bad day- good luck, that shell is a lot harder to crack, but not impossible.

• Easily won over by people who show they’re 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? You’ll make quick friends with him.

• He’s either a good liar or a terrible liar depending on the situation. Tells them confidently and hopes no one notices. Unfortunately they’re 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. Wasn’t big on reading until he’d met his wife, and she talked so much about the places she’d like to go someday that he couldn’t 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, wouldn’t 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 “oh man that was so stupid of me to do” way that makes you both laugh.

• Is not picky about his cigarettes, nor his alcohol, which has made it very difficult to quit either. He’s tried multiple times but can’t fully commit to doing it without help.

• Like all good people, desires to someday be behind the wheel of an automobile. (Specifically the ‘06 Ford Model N)

• Seen by the other carnies as a guy who’s 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 can’t.

• 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.

—Dating/ Relationship—

• Would like to take things slowly depending on how long he’s known you. If you’ve known him for a while he’ll probably be more comfortable with the idea of dating as opposed to someone who’s just visiting the carnival. (Though I don't think he's opposed to the idea of quick flings if you're just visiting)

• Because he’s observant, he will get to know the things you like fairly quickly. If you’re already traveling with the carnival you’ll 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 you’re kind enough to pop/ rub his back after a long day he’ll 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 they’re in the corners and out of the way so it doesn’t impact the function of the mirror. But sometimes, if you leave him for long enough, he’ll 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, you’ve 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 won’t 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 he’s surprisingly heavy and difficult to move when he’s asleep (unfortunately it’s because he’s so damn tall there’s so much more of him to move around). If you half wake him up and ask him to move off of you, there’s a good chance he will think you’re joking, laugh, and fall right back asleep.

• 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 he’s 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 you’re doing regardless of whether or not you’re 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 you’re thinking about him all day.

^ Would love it if you did the same to him.

• Likes to check in on you, make sure he’s not being too rough (even if you tell him you want him to be a little rougher), doesn’t 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. He’ll 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 he’ll leave red greasepaint kisses on your mirror so when you stand and look at your reflection you’ll 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 he’s 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, it’s inevitable you will fuck in the Pennywise outfit at least once. Whether it’s intentional or not, it’s going to happen. If that’s something you’re really into (who among us wouldn’t be), he thinks it’s very endearing once he figures it out and will go out of his way to make it happen more often.

^ Fun little bonus: if you’re the one fucking him and his makeup gets messed up he will ask you to fix it. Tells you it’s only fair even though you made him cum so hard he’s having trouble standing.

• Is much more comfortable being the one doing the penetrating and would be pretty hesitant if you asked to switch positions. Won’t outright tell you no, but there would need to be quite a bit of trust between the two of you before he’d 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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