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Sissy Caption Roommate
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the good roommate
Caught by your roommate, Sissy
the good roommate
Prank your roommate by riding his big, straight cock. That'll show him.
Your roommates girlfriend broke up with him, So you decided to step up.
He didn't get the joke
Wish my roommate would walk in on me and fuck me rn~
Your roommate didn't expect the bet to end like this
Your roommate likes alt girls
Show him what a good roommate you can be ;)
Your roommate got your hints ;)
You've always wanted your roommate's dick
Your roommate was a little drunk last night and mistook you for his GF..
CaptionShorties: Crazy Roommate
You have the best roommates ever! ?
My Roommate Helps Me With My Girl Problem
Shout out to the best roommate! ♠️
Enough teasing
I was just playing I dare you with my roommate ...
I just didn't want him to be pent up
An amazing roommate!
I just wanted to know
He just wanted to practice massage on me
Handcuffed for your roommate
unemployment didn't seem so bad
Best decision ever...
You sure don’t mind losing anymore!
"our roommate is a WHORE!"
New roommate
you accidentally threw out your roommates fleshlight. So he turned you into one
I wish my roommate can read this and do it on me
Your roommate's Birthday... (Part 1)
Your roommate's Birthday... (Part 2)
Your roommate's Birthday... (Part 3)
Your roommate's Birthday... (The End)
You know he likes it
Trying to prove your theory
Surprising roommate with your Sissy Tranformation
Your roommate always provides a convincing argument
If anyone is gay here it's my roommate, right?
A helping hand
What else would you do for his silence?
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My GF's roommate needs a goon bud
I'm lucking to have such a generous dadd-- I mean roommate
Deal with roommate
Showering with your roommate
Things are different between you and your roommate
Your hung roommate is gonna catch you being a sissy slut!
My roommates gf broke up with him and now he thinks that means I’m free use
My femboy roommate wants help making goon fuel
Cheering up your roommate
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waking up with a weird taste in hour mouth?
I would love to dress up like my goon buds favourites so we can practice like this
he's just tying shoes
Wrestling with roommate is not gay
Still straight if we use a fleshlight
It's a win-win situation!
You were on an online interview when your roommate stumbles in saying he knows your "little secret"
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