Alice In Sissy Land - Crossdressing

Breast Worship Pt 5 Sissy Sex Training FemDom Strap-On

Sissy Sex Training Part 5 -
Breast Worship in Stockings and Garters

Now that Monika is wearing makeup and dressed in sexy merrywidow lingerie and garters, she is really ready to loose her virginity like a real slut!

I have to teach her about the proper ways to be a good girl and please her partner. She will have to learn all about my breasts and receive special instruction in how I like to be touched in order to become my perfect sissy sex slave.

I also dress her in sexy sheer stockings to make her as sensitive and sensual as possible while my friend takes photos of her ongoing transformation.

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Ass Fingering a Virgin Pt 4 Sissy Sex Training FemDom Strap-On

Sissy Sex Training Part 4 -
Ass Fingering a Virgin

My insistent probing slowly starts to open up Monika's virgin ass and soon my whole finger is buried inside of her.

I am going to teach Monika to enjoy her little sissy pussy and it won't take long before she will learn to have orgasms from being fucked that way, by women's strap-ons and eventually even men's big hard real cocks.

Her sissy clitty cock is certainly massive and hard, too big to fit into her stolen panties, so I pull them aside to stroke it.

The more I probe and stroke, the harder and more helplessly aroused my sissy sex trainee becomes. I think she will learn to enjoy her role as sex slave!

... especially once I start leaving lipstick prints all over her hard cock and force her to pleasure my breasts!

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Slutty Red Lipstick Pt 3 Sissy Sex Training FemDom Strap-On

Sissy Sex Training Part 3 -
Slutty Red Lipstick

I think my sissy will look great in makeup. When we were making out, I accidentally smeared my red lipstick across her lips. I liked the way it looked so much that now I'm going to give her a full makeover!

Before I take my sissy's virginity, it is time to dress her up like a sexy big girl in red, instead of an innocent virgin in pink. I want her in slutty red lipstick and dark eyeshadow before I take advantage of her!

She covers my breasts in red lip prints before we go back to kissing in our sexy red clothes and matching slutty bright red lipstick.

All this transformation play, makeup and girliness has Monika helplessly aroused. I know that now she is ready to do ANYTHING for me...

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Probing a Virgin Pt 2 Sissy Sex Training FemDom Strap-On

Sissy Sex Training Part 2 - Punishing & Probing a Virgin

My little sissy Monika confesses that she's never had anything in her sissy pussy?

And what exactly is a sissy pussy? It is when a sissy is specially trained to take Mistress' and men's cocks up her tight little ass. When a sissy is properly trained her ass becomes just like a real girl's pussy, sensitive and pleasurable to the point of orgasmic!

The more I play with her tight virgin hole, the more erect Monika becomes. We make out and she gets harder and harder until I can tell that she is ready to have her cherry popped.

I fondle and probe her through the pretty pink stolen panties until she begs me to take her sissy pussy virginity with my big strap-on cock. She blushes so preciously as I get her ready to be deflowered.

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OTK Spanking Pt 1 Sissy Sex Training FemDom Strap-On

Sissy Sex Training Part 1 -
OTK Spanking

When I come home unexpectedly early, I catch my sissy boyfriend dressed up in my clothes and jacking off! He's wearing my favorite pink rose print sundress and is wearing my favorite pair of pink satin panties.

Leave it to a sissy to steal the girliest clothes in my wardrobe!

Instead of interrupting her masturbation right away, I decide to spy on Monika for a little while and wait until she's fully erect and as turned on as possible. Then, I barge through the door.

I was only gone for twenty minutes and already she's dressed up like a prissy sissy and jacking off without permission!

I make Monika show off her pantied hard-on before punishing her with an over the knee spanking... so that she learns what happens to naughty little girls when they play with themselves without permission.

My love of spanking discipline is obvious as I correct my sissy's behavior the old fashioned way!

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Sissy Sex Training FULL MOVIE Oral Sex Slave Strap-On Training

Sissy Sex Training FULL MOVIE

Monika's first time is captured here on camera. Enjoy this "breaking in" scene as I teach her how to take it in the ass... but not until she properly worships my pussy!

I catch my boyfriend dressed up in my panties and sundress and it changes our plans for the afternoon... instead of going out, we are going to stay in for a very special lesson in the charms of his "secret sissy pussy."

First, spankings and humiliation, but then makeup and sexy clothing. In the end, I am so turned on that I get off using her mouth before strapping one on.

She is so desperate to have an orgasm as I give her a teasing blowjob that soon she agrees to loose her anal viriginity to my strap-on if it means I will allow her to have an orgasm!

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Public Humiliation Pt 8 Rubber Mistress Femdom Training

Mz RubbaDubDub Pt 8
The Morning After... Alice Gets Her Turn

Mistress Minax's rubber slut has no idea what he has gotten himself into... now he is locked into chastity and has no idea when he is getting unlocked again!

With no idea when he will ever have an orgasm, I schedule a "morning after" meeting with him over coffee for some public humiliation play at Wicked Grounds (an 18 and over kinky coffee shop).

I force him to show off his locked-up-cock in public (shocking a few of the other patrons but making a lot of women laugh) before escorting him to the public bathroom to investigate his predicament further.

This daring and embarrassing public scene has reallys stuck with this poor slave (and I don't just mean the bruises on his dick).

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Chastity Lockup Pt 7 Rubber Mistress Femdom Training

Mz RubbaDubDub Pt 7
Hitatchi Lockup

Simple chastity cannot satisfy Mistress Minax's sadism... first her rubber slave must be driven to the edge of orgasm and sanity with a vibrator!

She weilds the Hitatchi Magic wand as a weapon of pleasure and frustrated lust in this delicious latex tease-and-denial video that culminates in a sexy chastity lock-up.

Mistress pleasures him with her hand and her toys but won't permit a release. Before he looses control, it is time to lock her slave up in a silicone chastity device loaded with spikes to punish erotic thoughts.

This poor slave has no idea if, when or how he will be let out of chastity!

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Tease Handjob Pt 6 Rubber Mistress Femdom Training

Mz RubbaDubDub Pt 6
Tease Handjob

Mistress Minax's rubber slut has one last chance to have an orgasm before he will be locked into chastity... so she sits back and orders him to masturbate while she watches, dressed in rubber, on her throne.

He suffers so beautifully for her that she is moved to play with him more, but Mistress teases and torments him mercilessly instead of permitting him to have that coveted release.

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Orgasm Control Pt 5 Rubber Mistress Femdom Training

Mz RubbaDubDub Pt 5
Orgasm Control

Mistress Minax has kept her rubber slave hard and aching for his release all afternoon... but maybe she will finally let him have an orgasm.

First she gives him a sexy, teasing handjob... alternating stroking and spitting on his helpless hardon, but soon she turns her attention to his tender ass and a much larger metal didlo.

She fucks him with the stainless steel dildo relentlessly and humiliates him further by forcing him to communicate only in duck quacks while he begs for release.

Will Mistress Minax allow her slave to have an orgasm or will she lock him in chastity overnight? Tune in to find out!

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