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Everyone totally agreed that Mrs. B was the best senior class ski trip chaperone...

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Wancho - Le Petit Chaperon rouge

Lolicons

Chaperoned

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Brother, are you sure you wouldn't introduce me to some of your friends? I've seen the way they look at me...you can chaperone our date too!

DirtyFamilyPhotos

Would m'lady like to be chaperoned to the bathroom?

justneckbeardthings

Chaperoning my Daughters Third Date.

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When I started seeing her best friend, sis demanded to play the chaperone.

gifcest

When I started seeing her best friend, sis demanded to play the chaperone.

Incest_Gifs

With me as chaperone, my sister keeps from getting into too much trouble with her new boyfriend.

IncestGifs

Mom insists on chaperoning when my girlfriend comes over. But more so that I live up to expectations.

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With our religious parents, I'm the only boy my sisters are allowed to see without a chaperone. Which isn't as bad as it sounds.

IncestGifs

Milfy Chaperone

milf, OnlyHotMilfs, dailymilf

Mom looked to be having fun chaperoning your prom

mommybully

Your mother had been scheduled to chaperone the freshman dance, halfway through the dance your bullies showed her who was boss and fucked her right on the dancefloor

mommybully

After chaperoning the school prom, Mom joined my bully's after party

mommybully, pornID

Mom chaperoned our school camping trip

mommybully

Your Mom volunteered to chaperone at the school dance. And your bullies took her to a back room...

mommybully

Mom stumbled home with my bully after chaperoning our prom

mommybully

I followed your Mom to her hotel room after she chaperoned the prom

mommybully

Your freshmen class went on a trip to Hawaii for a week and your Mom was one of the chaperones...

mommybully

[M/S] She claimed someone had spiked the punch at the school dance she was chaperoning.

taboocaptions

Le nouveau Chaperon Rouge

SexyGirlsInBoots

Chaperoning for her son's senior school trip.

taboocaptions

“Do it before the school trip chaperone comes back here!”

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She could be a little wild sometimes, so they came up with a solution. [humour] [exhibitionism] [useless chaperone]

xxxcaptions, VanillaCaptions

My wife's chaperoning field trip. Just got this from one of the other parents. I guess she's enjoying herself

Cuckold, Hotwife

When you are the reason the school has to have a dress code for chaperoning field trips... ?‍♀️?‍♀️?

realmoms, amateur_milfs, BBW_Chubby

At Church Camp... one of the adult chaperones...

KneesUpFeetDown

Le petit chaperon rouge

NSFW_Outdoors

Mom chaperoning their child's trip to the zoo [OC]

TittyDrop, Amateur, RealGirls

Young sister needs a chaperone

keyholdercaptions, IncestCuckCaptions

The haptic feedback on my chaperone boundary is a little too good. My first VR injury.

VRtoER

Napalm Chaperone (kimmy77)

RWBYecchi