(Here are some scenarios while you wait for the juicy stuff)
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Bill- He Fingers you while he sucks your clit, he's gentle at first to make sure you are able to feel the sensation of pleasure then goes rough and then starts slowly pushing inside your pussy
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Roman- He's rough, he'll force your legs open and bites the lips of your cunt to make them bleed, he licks the blood while licking your sensitive pussy and then roughly shoves his tongue inside you
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The Kid- He doesn't know what it means by 'Eating you Out' at first. He gently licks your pussy, every time you squeak when he touches a sensitive spot he stops and looks up at you with worry in his innocent eyes thinking he's hurting you, and he constantly says 'Oh my god, I-I'm sorry, I didn't mean to hurt you.'
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(I know it isn't Matthew The character, but that's all I could find on my phone)
Matthew- He kisses the lips of your cunt before he starts licking your sensitive pussy and shoves two fingers inside of you, he knows how to make you moan loud when he's eating you out
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Pennywise/Bob Gray- He freaky when it comes to eating you out, to him, you're a different kind of meal, he won't really eat you like he eats children along with their fears, you're like a dessert, like a sweet treat to him, to him, your pussy taste like caramel and Cotton candy
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Merkel- Let's just say, if you're his good princess, he'll give a hell of a lot of pleasure, he'll be gentle with you unless he's super horny it's rough, but if you're a bad girl he'll tease you a whole lot, so it's best to be his good little girl
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(No gif I'm sorry)
Axel/Zeitgeist: He says he can't because he's afraid to burn the flesh of your pussy off you, due to him to have the ability to vomit out Acid power. Although you both wish for things like that more than anything. So you tease him about his power of limitations to get him pissed yet horny at the same time. He'll pinned you against wall, first he'll give you hickies while fingering you, he'll be cautious about eating you out, he'll then kiss you from your lips to the lips of your cunt, and stroke his tongue along your sensitive pussy and then thrusts his tongue inside you.
Holy shoot, I'm sweating now heha, *sighs* okie bye
