Includes stepmom - sissy training - sissy coercion - exposed sissy - sissy training - encouraged crossdressing - mindfuck - femdom pov - female domination - ebony female domination - ebony - interracial    

Stepmom Ava is full of questions!

But before she dives in too deep she wants to know the kinds of thing that turn her wee lass on

Does she enjoy being manhandled?

Or does she really want to be treated like nothing more than a fuckhole?

Stepmom Ava spreads this pussy all the way out!

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Jonathan has been secretly dressing up for a while now. At first he only used to secretly wear the clothes and enjoy how lovely they felt on his skin.

But more recently he has been delighting in how the material feels on his skin. In fact it made him so horny he started researching what other people do when they crossdress. And when he discovered chastity he fell in love!

The beautiful feeling of the cage, restraining his cock so that he can't think of anything other than edging and enjoying the sensation.

Jonathan's turned into a real slut.

It's on one of these little nights in when he has dressed up as Jessica (his alter ego) that he is edging, so very close to cumming. 

And he doesn't realise that his stepmom Ava is looking for him.

And when she bursts into his room he doesn't react fast enough to stop what he is doing!

She sees it all!

But her reaction is unlike anything he could have ever imagined!

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Have you ever seen a sissy transformed into a cock-loving whore?

Well, this is one of those such times

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Now Jessica must learn to ride cock like a pro!

The better she is the more the money will just flow in!

And everyone knows, every sissy needs real cock to feel like a real woman.

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Mistress knows Jessica has more potential. Potential to make Mistress heaps more money!

So she needs to LEVEL UP her game if she's going to pull in the numbers that will keep her Mistress happy.

So today she has to start her training. Start to move more gracefully, learn to tease, how to seduce... in short, how to get their cocks so rock hard that their brains turn to mush and they want nothing more than to pound her for pay!

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When I get my feet worshipped I expect them to be worshipped properly! That means using the correct etiquette and learning how to treat and caress my feet like the valuable items they are! It would appear that Jessica Dee needs a few lessons! Watch and learn as my very well behaved footboy shows you how to go about this act of complete servitude!

Me and Ruby Onyx strap up our sissy Jessica Dee and ensure we cant hear her whining as we shove a ball gag in her mouth! Now firmly affixed and unable to move we go to work in teasing this sissy bitch into complete submission! All locked up in her cage and totally helpless we take great pleasure in subjecting her mini manhood to our orgasmic wands! Its time to play until we finally reach Sissygasm! Sadly for this little slut, it wont be as pleasurable for her! Ha!

Sissy girl Jessica has been locked away in her tight pink chastity cage for 100 days. Today I promised her that she could have an orgasm - but with a twist! Her ankles tied to her ankles and her hands behind her back in pretty pink rope leaves her chaste clit exposed to my cruelty. Firstly, she must open her mouth nice and wide (she is used to that!) so I can slip a blue Viagra pill onto her tongue for her to swallow down. This blue pill will keep her girl-clit rock solid, swollen and pushed up against her cage whilst I tease her with feathers and my vibrating wand - but can I really stick to my pledge of allowing her to cum?

I am running late for my date at the opera with my lover, so I must utilise my chaste sissy husband Jessica to help me get ready for the occasion. It is Jessica's job to silently rub lotion onto my long, slender legs as I brush my shiny hair and apply my make-up. There will be no room for jealousy here - my cuck husband knows the only way I will allow her to remain in my life is as my maid. She must prepare the perfect bed linen and ensure the house is immaculate before I arrive home with my well endowed lover. Jessica knows her pathetic little cock has never satisfied me, so we have removed it from the equation by keeping it locked away by the key that lies delicately and foreboding around my neck. My pleasure is all that matters.