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If you have a picture that you think is begging to be captioned, send it my way and I’ll see what I can do.

Caught in the act all dressed up in her lingerie.

The woman next door came over and caught you cross dressing in your wife’s clothes and now your secret is about to become public knowledge

Hi, I caught my cross dressing boyfriend dressed up in my clothes, again, and I want you to come over because I have the bitch tied up and I think we can have ourselves a little fun.

Caught shoplifting from her lingerie store

Caught stealing laundry from the basement of a sorority house

Caught by your wife

Text from your girlfriend

Caught cheating with a shemale series

Caught cheating with a shemale

Caught cheating with a shemale

sissyforcock: My brother accidentally caught me dressed up. I figured now was a good time to tell him I’d always wanted his cock, especially ever since I found those magnum condoms. I told him I’d be practicing on a big dildo pretending it was

What the fuck, roomie?Going through my panty drawer, really? You’re so fucking pathetic.Oh my god, are you wearing a pair right now?!Give those back you sissy freak! Those panties get to rub my perfect little pussy, something you’ll only ever dream

Have you really been wearing my panties?!

Not the Opera Gloves!

The Wife’s Return

Webcams: The Bane of Sissies Existence.

Greedy Mothers: They’re always cockblocking the the good stuff.

Panties: A woman’s panties are sacrosanct. Buy your own… unless the plan was to be caught and forced into feminine servitude.

Dare to Dare: Are you sissy enough to take all those dares?

The Trap: You should have known she put those clothes in there just for you, sweetie. Welcome to your new room. And don’t worry about all your nasty man clothes; she’s already thrown them out. Enjoy your new life of servitude, you lucky sissy.

Coming Clean: Why do sissies always try to hide who they really are from their wives? They always get found out in the end and then there is all the humiliation to deal with. It’s best just to tell them up front and get it over with.

The Beginning: this is how it almost always starts; sloppiness on the sissy’s part. Or maybe it was purposefully sloppy. Hmm.

Accidental Self-Outing: I know I’d by more insurance policies off of a latex sissy.

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.

Strong Women: they know exactly what they want.

Humiliation: all closeted sissies crave it. Make sure to let everyone in your neighborhood aware of his new situation!

Bridesmaid Dresses: There should be a law or something.

Backstory? It’s the truth!

Isn’t modern technology great? No more awkward conversations with your sissy husband. Now you can arrange it for him to come out of the closet on your schedule. Take your sissy by the balls today!

You never know who is watching, so make sure to always put on a great show!

ppsperv: Follow my tumblr—> Pretty Pink Sissy Perv

cicistories: You thought you did a decent job of putting all her lingerie back in the drawer but it seems like she caught on. She found your alter ego though, someone so cute and naughty she had to help you bring them out so you could both enjoy it

sissyjustbitch: humiliation sissy bitch captions My gf just caught me I just wish she was more of a dominatrix time will tell

sissy-panties said:Will you make a caption of a guy getting caught in his sisters panties by his sister

Goddess Candice caught you dressing up

Threesome Thursday: You’re a chastity slave to college girls now

Threesome Thursday: Goddesses Josephine and Taylor saw your panties and now they’re going to feminize your sissy ass.

Model caption request: Mistress Kendall makes you her strap-on sissy slave.

Model caption request: Goddess Alessandra wants to make you her sissy bitch and peg you

Model caption request: Mistress Kendall spanks her sissy slave and makes him lick up his cum

Caught and UsedIf you want a lot more captions every month, then visit my Patreon! We are very close to the 񘈨 goal!!!https://www.patreon.com/katyscaptions

Sissy Caption - Caught in the Act

Sissy Caption - Caught

Crossdressing Caption - Caught in a Trap

marycocumslutoriginalcaptions: CAUGHT SPYING ON SISTERS AND MOM – NOW YOUR THEIR CUM EATING SISSY – ANOTHER QUICK ONE INSPIRED BY BROWSING TUMBLR GIFS – CAPTIONED VERSION TO FOLLOWYOU WERE CAUGHT RED HANDED YOU HAD BEEN CAUGHT IN THE PAST SPYING

Mommy caught you wearing her panties.

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