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Description

a little something while drawing with a friend for the first time
i love the idea that cheerilee is just a really really bad influence lol

safe2206677 artist:pinkberry251 cheerilee11348 earth pony518832 pony1636915 g42061783 aggie.io655 alcohol10373 bad influence27 colored sketch4839 doodle4847 drunk6073 drunk bubbles572 female1839527 glass6971 imminent foalcon171 looking sideways2103 mare764395 sketch84491 solo1452496 wine3616 wine glass2405
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Background Pony #D34B
Also, this leads me to ask…
Does Cheerilee disguise sex ed classes as a way to have sex with her students?
I could see that. Cheerilee goes to the parent, tells them that their little colt is falling behind, but with a little extra attention she’s sure they’d be able to get it, no problem. She gets the student alone, suggest a more… experience based method of learning, and then rides him until he can’t even get it up anymore.
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Power Play
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
Wallet After Summer Sale -

Non-Canon Game Horse
Also, this leads me to ask…
Does Cheerilee disguise sex ed classes as a way to have sex with her students?
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Background Pony #D276
The line “I won’t tell your parents” just makes me think she’s talking to Monster Kid from Undertale, because they repeatedly tell people not to tell their parents where they are.
@Background Pony #D34B
I also quite like the headcanon that Cheeri and Berry are sisters.
@NightWriter
Cheerilee already has her own harem, and they’re at just the age that she likes ’em to be.
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NightWriter
Wallet After Summer Sale -

Cheerilee better be careful, who knows what sorts of stallions might be angling for a date with her if they find out she’s sharing wine with colts.
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Power Play
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
Wallet After Summer Sale -

Non-Canon Game Horse
@mulbmerl
Don’t forget the possible implications if she lets him cum inside in that state…mmm…
Everyone would be wondering why Cheerilee’s belly is bigger all of a sudden
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