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Love at first sight.

Sweet dreams

Your lips are sealed... most of the time

He's awfully sneaky

[M4M] RP as my roommate who takes advantage of me when I get stuck under the coffee table while crossdressing
![[M4M] RP as my roommate who takes advantage of me when I get stuck under the coffee](/thumbs/e6/31/GlassLightcyanBagworm.jpg)
You're the Perfect Roommate!

Your girlfriend joked that your roommates cock was at least twice your size. Time to break up with your girlfriend so you can worship his Huge Cock instead!

[Reddit] I love teasing my roommate
![[Reddit] I love teasing my roommate](/thumbs/83/89/IdleDarkgreenPlainsqueaker.jpg)
You got your roommate a "gag gift." it was a bunch of silly coupons... one was where you had to dress and act like a girl for a full day.

[M4M] RP as my roommate who finds me stuck in the new handcuffs I was trying out
![[M4M] RP as my roommate who finds me stuck in the new handcuffs I was trying out](/thumbs/de/1e/ExtrasmallAdorableVirginiaopossum.jpg)
Roommate stressed out? No problem. Its your job to let him use you

Accident prone

He knows what you are now

You'll always help a roommate in need

Thursdays are the best! It's the day when your roommates take turns blowing their loads on your face!

Interrupting your roommates workout was the best thing that has happened to you in ages!

Your roommate caught you practicing on a Dildo in the shower.. so he offered you something MUCH better to practice with!

Your GF & Your roommate are always horsing around in the other room..

Maybe you should show him that you could be an even better roommate and service his massive cock like the good slut you are!

Your roommate showed you his huge cock and it triggered something inside of you.

Moments after I walk in on my roommates jerking off

Every sissy should have roommates like these :) :p

CaptionShorties: Idiot Roommate

Oh no! My roommate is gonna catch me fucking myself!

Roommate just couldn't hold back

your roommates girlfriend never rims him or sucks his dick..

Getting blackmailed by my roommate and girlfriend ❤

Making things clear to my roommate

Sissy helps a pent up roommate

Ever wondered what your roommates cum tastes like? (part 2)

Best roommate

Anal Caption Roommate Sissy clip

Frotting Roommate Sissy

Lazy roommate sissified

Sucking cock breaks a sissy's brain

He certainly kept his promise

He just helped me explore myself

There was only one way

Poor guy, luckily i could help him

You are a good roommate aren't you?

Roommate's Sister (Part 2)

Roommate's Sister (Part 1)

Roommate turns you into a cumslut

Sharing the shower with your roommate

Amateur GIF by boyhole22

free use sissy roommate

Cum smarter, not harder

Chastity Key

my roommate's so stinky! 😠

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your roommate was out, or was he?

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The Ring part 4

The Ring Part 3

The Ring Part 2

The Ring Part 1

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Roommates
