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Caught by you roommate

Your roommate was drunk & you were dressed up...

Pro's and Cons

Bullies should get paid by the government to feminize

The origin story of half of this reddit's users

Im just a cock hungry slut

Everyday's plan

A new slut is born

Don't stop daddy...

Totally straight goon session | By Str8BroacaptionX

I fall harder for him, everytime he drills me

All your mouth is good for is sucking cock

Anime convention | By u/captionporn2000

You grew up dressing as a girl | By wxhluyp

If you can't decide...

Your buddy walked in on you dressed up in his girlfriends clothes

The halloween party

Aaahhhh

On my time off - By AskMe

Getting a teaching job - By MisterSyn

It probably runs in the family

You are nothing more than a hole for daddy to fuck

"Talking" with the coach - By SissyRoshnii

It's hard to fight aDICKtion...

However they want

Your supportive girlfriend

It were just two stupid words...

Daily reminder to get pretty & practice

The first date

Daddy likes it

Popped

Got arrested for speeding 😔

Requirements for dating

Sissy Caption Hypno

Just a few photo's

Once you become this sexy...

I'm not leaving, this party is way to much fun!!!

Asking for help...

You had to admit, they were right...

Sissy life is miraculous

Starplayer Pt.1

Don't make it easy - By John-Bear-Jr

I'm not gay, just curious.

It's supposed to be a punishment

How he changed my life

He made sure you knew your place

Boy clothes are so boring...

Don't give him idea's

My best idea yet

You probably should stop betting that your cock is bigger...

Saving your dad | 25K captions 7

You seem a bit too happy...

Free vacation | by u/captainporn2000

It's not cheating if she is sleep

A BBC know where to hit...

It was supposed to be a straight goon session...

Remember the first time the repairman came over?

He could look straight through you...

A new role in your life...

A sissy balletstudio - By MysterSyn