#caught sissy | Explore Tumblr Posts and Blogs

louise-swell · 11 days

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A challenge with the lovely @alwayscute

#caption challenge #caught sissy #sissy desires

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miss-bridget · 6 months

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When Alan took early retirement, he was looking forward to playing golf, holidays, fine wine and generally all manner of new experiences. His wife had her own ideas about his new life after work…..

#cd #caught sissy #bound #maid

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josef851226 · 3 days

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8 inch dildo

#dildoplay #pantyboy #beta sissy #small dick humiliation #transgender #feminine sissy #feminization captions #gay #caught sissy

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sabrinaocumps · 3 months

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kiyana3692 · 2 months

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Can I seat on you ?🥺

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louise-swell · 3 months

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Are you Gay enough yet, or are you ready for more @sissymissyxox

#caught sissy #sissy desires #what a sissy wants #how to make a sissy smile

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miss-bridget · 2 months

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Many unexpected things happened to the boys this weekend. Being caught and enslaved by the sissy traffickers was a nightmare that they couldn’t ever conceive.

But the long hours in their new attire and makeup, tied and gagged together, brought up some strange feelings. The attempts to remove the gags resulted in some very heavy groaning and squirming. Maybe they have a promising future in the world of sissy whoring. Maybe they’ll get sold as a pair…..

The damp panties will certainly give us a clue to their thoughts about it all.

#cd #glam girl #caught sissy #bound

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goddessnelley321 · 2 days

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CAGED HUMILIATION.

#caged chastity #sissy caged #locked in caged #caged foot slave #sissy caught #chatity #sissy bitch #lock in chastity #submisive sissy #sissy tasks #feminine sissy #panty sissy #beta sissy #sissy cd #serve me #humiliated sissy #humilated slave

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sabrinaocumps · 3 months

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whiteboi-inferiority · 3 months

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Cassie moved out later the same day, shamefaced and embarrassed. You didn't exchange another word. What was there to say, really?

...but on the upside? New panties and dildo! So.. Yay?

#loser humiliation #pathetic loser #beta faggot #whiteboi feminization #beta sissy #bnwosissy #pussy free whiteboy #caught with consequences #white bois #white boys

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profmdiaries · 8 months

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Do you like pain? No? Well...don't worry. I'll train you to beg for it ~

#humiliated sissy #feminine sissy #sissyfeminization #feminization captions #feminized husband #sissy domination #humiliation sissy #sissy tasks #panty sissy #faggot sissy #submisive sissy #sissi femboi #feminine boy #feminization kink #forced feminized #sissy caged #hypnotized #hypno fantasy #sissy caught

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louise-swell · 4 months

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#caught sissy

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miss-bridget · 2 months

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Gender Gap. Part 2

I laid the latex maid outfits out for my new toy to look at. I had taken the liberty to include contrasting cages too. He gurgled a protest around the ball gag and I slapped him hard across the face. He whimpered a little bit and I grabbed his shrunken balls roughly….

“Now, you little streak of rat’s piss. This is what will be happening. I’m going to give you a choice. It will be the only one you’ll get while you’re in my company. Pick a dress and a cage. We’re going to film a little video and it will be uploaded to every account you have…..LinkedIn, Facebook, tinder…..Grindr. I say that, because you might get a lot of new followers who like sissy cunts.”

He cried in pain as I then spitefully twisted his nipples. When he stopped snivelling he grunted and nodded his head toward the black dress. It was predictable, but at least the cage would be nice and pink for my little whore. In truth, he would be wearing both at various points, but we had to start somewhere. I locked the cage on his disgusting cock and tugged it once in place. Another gagged yelp escaped his mouth and another slap followed.

I stood him up and forced the dress on his body. The glossy latex clung to him, with the skirt flitting out nicely at the bottom. I spun him around and inserted a matching pink anal plug up his ass. His eyes widened as the toy invaded his rectum and he slumped in resignation. I was disappointed, I was expecting this ‘alpha’ prick to put up a fight…..but he was cowed and humiliated already.

I produced the black stockings and put them on his legs….one of them was laddered….enhancing his look of a used slut. The high heels were too small, but I wedged his trotters in them and dragged him to his feet. He tottered unsteadily, more groans of pain emanating from his drooling lips.

“There. We’re almost done. But you look far too ugly and I want a pretty maid, don’t I? So, I think we need to see if I can perform a miracle and turn you into something even I might want to fuck.”

I grabbed the make up bag and started to apply the rouge and the lipstick. His lips were perfectly wrapped around the ball gag, making it easier to paint him into a tart. Next, the garish blue eye shadow, mascara and false lashes.

I stood back and checked my work so far. “My goodness, you really are a wanton sissy aren’t you? If I check your cage I wonder if you like it so far.”

Of course he had a mirror in his office and I shunted him over to look. He struggled and tried to curse at me….so I stuck my hand up his ass and started to manoeuvre the plug around. He shrieked like a bitch and guess what? The dreary little cock was straining in its prison. I chuckled and brought him back to the chair to continue his makeover. The auburn wig wasn’t quite his colour, but he looked presentable from behind at least. The setting up of the camera took time, but at last we were ready as I got him on all fours….crawling around his office and shaking his plugged ass for me. I lifted the skirt and the base of the squat plug was firmly on show, along with the cock cage dangling uselessly in front.

The leather slave collar was buckled on and I led him around the office a few times. When I bent him over his desk, i made sure his cuffs were tight. He saw me take the strapon and step into it….i did it slowly and deliberately just to give him time to beg….but it wasn’t going to change my mind.

The camera was set and so was I……the plug would be removed and there would be no doubt, the little slag’s mascara would be running down his face….

TBC

#cd #glam girl #caught sissy #bound #punishment #gender gap

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goddessnelley321 · 9 days

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