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The largest and most original cheating and cuckold captions archive on Tumblr!

The largest and most original cheating and cuckold captions archive on Tumblr!

from protester to prostitute

From Punk To Prostitute

The Best Prostitute

T-bone’s Revenge

Transvestite Hooker: It used to be your fantasy.

The Great Escape

Don’t Borrow Your Sister’s Lingerie: Buy your own! Oh, and by the way, Tommy, it’s a trap. Your sister might be getting you the work, but she’s going to charge for training you to be a sissy and a finder’s fee. You’ll

Spring Break: I don’t know about you, but I’m going to South Padre Island for my Spring Break!

When in Thailand: Don’t forget to take advantage of the local nightlife, Caution: waking up in the body of your bed mate may lead to long term sexual addiction, prostitution, and various kinky situations with members of various genders.

Discounts for volume? That’s unheard of!

Role Playing: It takes a dedicated husband to really get into a character like this.

Man of the House: It’s great when a man is dedicated to his work.

Bringing Home the Bacon: A man’s got to do what a man’s got to do in this economy.

Not a Damn Bit: Uh-huh. Chelsea likes.

Happy Birthday! I want to have a present like this!

Turned Out: Sometimes you get lucky and your wife accepts who you are, and sometimes you get even luckier and she doesn’t. Then you wind up with your new master.

Earn Your Way to Femininity The Old Fashion Way!

Social Security: doesn’t pay to tip your hooker.

Just 200 more blow jobs to go and you can get them removed. Who knows, by then you might enjoy the new job!

Hold on… you got all her shoes? You win!

Escorts are just classy prostitutes. They dress classy and look rich, but it’s still the same risky job. The risk is that sometimes, they end up kidnapped, bound and gagged, when the gentleman isn’I a gentleman at all. Isn’t that right, Miss Tasha

minnie-love-sucking-huge-thing: I left the caption intentionally. This is the “World’s Worst Prostitute”!She couldn’t suck a single squirt outta dat O'l Man on Viagra?Really? Is this what is P.C. curve acceptance? We are accept

In the Deadpool movie, Morena Baccarin’s character, Vanessa, is quite the domme. She fucks Deadpool with a strap-on. She comforts him about his deformed appearance saying his is “a face she’d love to sit on.” And employes herself as a prostitute,

Today marks the release of my latest feminization guide, “From Pimp to Prostitute”, which as the name suggests, is a step-by-step guide for feminizing a pimp. It features the beatiful Chanell Heart, who I’ve been wanting to use for

Today, I published a new caption story called “Survivor”. It focuses on the son of an oil magnate who’s kidnapped, feminized, and forced into prostitution. When he’s finally rescued, his family and friends have difficulty coping with his

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