Crossdressing Caption Gallery

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Maybe a striptease and then a blowjob while he’s playing Overwatch?
Well, it’s obviously for science, so okay.
Wait, all I have to do is act really slutty and I have to stay in this position? Well, there definit
Isn’t it so cute, the sexy submissive of the family trying to assert himself… er, h
What kind of boyfriend would you be if you wouldn’t be her girlfriend and take the occasional
It’s perfect! I’m going to be a real life Barbie doll!
Patience makes all things possible.
Feminization is  so much easier when the boy in question is very willing.  Sometimes the r
The Devil is in the details.
The Newest Workout Craze! Be a dutiful spouse and help your wife out with daily exercises!
Don’t waste your life acting like a guy! You know where you truly belong.
Fem-bois are best when captured in the wild.
Better use a lot of lube when you get ready. It looks to be a very long night.
A sissy must know her place! foreversissy.tumblr.com
lyndseygurl: This says you are
Finding your place in life.
Always in your panties. Always denied.
One entire year, minimum. No problem.
Pick up that damn leash and give it back to her you sexy little sissy!
Role-playing: how else are you going to explore all sides of being a girl before settling on one. At
I love making all my boys lock themselves up voluntarily. It’s especially satisfying to watch
Friends don’t let friends be sexually frustrated.
Since the advent of the internet, today’s modern library has branched out into other helpful s
Denial: Keep telling yourself that you hate it. We know different.
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