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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

safe2242419 artist:pinkberry251 cheerilee11467 earth pony535515 pony1673052 g42103832 aggie.io662 alcohol10622 bad influence27 colored sketch5082 doodle5026 drunk6180 drunk bubbles592 female1880820 glass7143 imminent foalcon175 looking sideways2184 mare788420 sketch86269 solo1484472 wine3680 wine glass2481
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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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