Sissy Training

Turning Hubby Into A Sissy - Part 2

mp4 237.95 MB

...after convincing my husband to cross dress for me I get out my strap-on & start training him to be a sissy slut. I'll be pimping him out so he needs to learn to suck cock & take it in the ass like a champ.
Length: 9 minutes

Turning Hubby Into A Sissy - Part 1

mp4 478.96 MB

I manipulate my devoted husband into dressing up in women's clothing to amuse me...I tell him that it will turn me on because I've started to like women & I've been having a lesbian affair...but then I drop the bomb: that I'll be pimping him out...
Length: 18 minutes

Cum Drinking Cock Sucking Sissy

mp4 285.84 MB

That's exactly what you are, isn't it? A "Cum Drinking Cock Sucking Sissy". Get down on your knees before me & show me what a hard working mouth you have. Show me what a good sissy you can be.
Length: 10 minutes

Sissy Ass-Fucking Cock-Sucking Training

mp4 263.92 MB

This cross-dressed sissy gets some lessons on cock sucking as well as getting 'her' ass stretched and broken in. I'll be pimping 'her' out so I need ensure she won't disappoint me.
Length: 9 minutes

Be My Sissy Crossdresser

mp4 363.06 MB

Custom vid (no name mentioned) of me, Mistress T, talking about "the rules" of what I require from a sissy, cross dressing slave. "Recently I have opened a special social club that caters to cross dressers and the men who admire them. I will need you at the club as a sissy and be prepared to pleasure men (or women) as I see fit. You will need to wear full makeup & ladies attire. I'm sure you know what most of these men want: first and foremost a good blowjob. Do you know how to give a good blowjob? I hope so because that's important in this role. Also we get couples who need a submissive." I guide you in a MASTURBATION INSTRUCTION explaining your role at the club, in particular all the sissy cock sucking & cum eating you'll be doing.
Length: 12 minutes

Sissy Boy Wanked Before School

mp4 297.45 MB

I always wanted a little girl, not a I dress my boy up like a girl. Before sending him/her off to school I milk him to ensure he doesn't pop a woody at school, which would raise some questions. While stroking him I tell him how I'll have to train him to be the perfect cock sucker in case a man tries to diddle him. That way he can keep them from going into 'her' panties by making him cum in 'her' mouth.
Length: 10 minutes

Humiliating Cock Sucking Training For Sissy

mp4 322.14 MB

I'm turning my cuckold husband into a sissy. He's going to learn to be a good cocksucker for fluff my lovers cocks & then I'll pimp him out. I've invited my friend Nikki over to see what has become of my husband & to assist me in the training. He'll need to learn to suck more than one cock at once so we have him practice going back & forth servicing both of our cocks. My young, hot lover watches and laughs adding to the humiliation. (Click to see more of Nikki Whiplash)
Length: 11 minutes

Sissy Cuckold and Stud

mp4 186.9 MB

My sissy cuckold kneels & watches while I stroke off my young, fit stud. I sensually milk a nice load of cum out of that gorgeous cock to feed my sissy. As part of her training she needs to learn to love the taste of cum so she can be a better cock sucker for me.
Length: 6 minutes

Sissy Extreme Chastity Tease

mp4 280.29 MB

*** UNIQUE CHASTITY! *** Cock piercing locks to piercing behind balls, locking cock in a downward position making an erection painful & impossible. My sissy comes into the clinic to have her transformation monitored. We discuss male urges & I unveil my reasoning for piercing that is now healed. I bring out a lock & key explaining to my sissy that arousal will become so painful I will now gain complete control over all male urges. I lock his/her cock to a ring between the scrotum & anus (perineum) then sensually tease him to demonstrate how painful erections will now be. This is a very sexy tease & denial vid with extreme chastity.
Length: 9 minutes

Humiliated Sissy boy

mp4 171.76 MB

Sidonia & Amica join me to see my boy off to his first day of school as a GIRL. I've always wanted a daughter so I decide to dress him up in something pretty. Before his big day we decide to milk him so he won't get an embarrassing bulge under his skirt. Can you imagine, being dressed like that in front of MILF'S pretty friends, then exposed and jerked to release?! How humiliating! (See more of Sidonia Von Bork from The English Mansion here: The English Mansion ) ~~~ (See more of Amica Bentley here: KinkyDirtyBitch)
Length: 6 minutes