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If she can cum from ityou will learn to cum too
Not the Opera Gloves!
Trapped and Trained: Can you be envious of a sissy like this? I think you can.
So Sad: when a sissy-wanna-be just can’t make the grade. Always listen and follow the instructions of your trainer. They know best.
Acceptance: It’s usually better if you simply accept that you were born to be a caged sissy-boi for the rest of your life. Quit fighting against what nature made you. If you were meant to be musclebound and have a large cock then you would have
Dildo gags: One of the most insidious devices known to sissy-kind. Made to suck on a realistic rubber cock while fucking your mistress with the other end, and made to watch her take it only mere inches away. It gets you used to being under her and watchin
Intelligent Sissy-boi’s: They’re out there and they’ll play you like a piano. It’s best to just encourage them.
Prostate Milking: Milk that sissy bitch! Milk her hard!
Frustration: It’s best to keep your sissy as high strung and sexually frustrated as possible.
BBC: Now you too can have your cake and eat it too! Keep your sissy locked in firm chastity and not have to worry about stopping your seduction in order to fit a strap-on him for your pleasure!
More Cute Shoes: a sissy has to have her standards.
Imagine how the sissy will feel when she see’s that pic. Sublime torturous humiliation.
Bad Sissy!
What’s the point in being a pretty pink sissy if you don’t act like one?!
Just wait until phase four!
Proper state of mind is important when feminizing your sissy!
Constant Positive Reinforcement is the only way your sissy will learn to enjoy being used as nothing but a sex toy.
The trials and tribulations of a kept sissy-slut.
Sometimes your keyholder has other plans for the evening. That leaves your weekly milking to you. You’ve been teased mercilessly for the last week and you’re fit to burst. What’s it going to be, sissy? Real cock or even more pain?
Girls=no ass fucking. Sissies=ass fucking anytime you want it. Why exactly do some of you prefer girls again? It boggles the mind.
Super Sissy Slut: able to walk around in public without all the hangups of mortal men.
Toss out all those guy clothes and commit!
He’ll do absolutely anything to have just one orgasm, even if it means taking his new wife’s strapon up his sissy pussy.
Once you’ve tried the really big cocks, nothing smaller really satisfies you anymore. Beware, little sissy. You’ll be craving giant cocks for the rest of your life!
Always reward your new sissy if she’s done something exceptional, but make sure it’s always in line with further feminization.
Four easy steps and your life can be so much more comfortable with your very own sissy!
Trust your mistress; she has your best interests at heart… and it’s best that you be stuck in chastity for the next five years. Although that clitty is very very cute.
Not even a sissy clitty? Hmm. That is a very pretty picture.
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cuckold-pictures-captions:Poor sissy comes before the cage is taken off.
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chastepantyboy: tenaciouscomputercoffee said:Hi! First of all, i’d like to say a big thank you for your work! I really enjoy it! Second, could you make a caption with these themes: became a caged 4inched sissy cause the envy for normal sized penis
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Anonymous said:Caption of a man who’s tormenters are group of Asian girls possibly the K-Pop Group Chi Chi. The catch is that the girls only speak their native tongue (Which would be translated for easiness) and the poor man is subject to countless
Singer caption request: Ariana Grande is looking for a new slave. Who’s interested?
Threesome Thursday: You’re a chastity slave to college girls now
Jaclyn Swedberg Week
I don’t think he’ll notice the difference…
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