Gangbang For Xdressed Fag Boy

mp4 461.72 MB

Twisted, hard core "Bi Encouragement" with your "MILF".

Custom vid. I'm excited to tell you about our upcoming night out dancing. I've decided to dress you up like a sexy lady, slutty dress, panties, stockings, wig, make-up. You will be so passable that men in the bar will treat you like a lady. They'll flirt with you, buy you drinks & dance with you. You'll make them really excited but when they figure out you have a penis instead of a vagina they'll get very rough with you. They don't treat faggots they way they treat ladies. They'll drag you into the washroom & have their way with you. Many of them. All running a train on your ass & mouth. They'll gang-bang you hard...but I know you well enough to know that you'll actually like it...

Length: 15 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

Feminized For MILF

mp4 361.55 MB

MILF puts a girly dress on her boy to encourage him to be more feminine. She wants him to like it so she arouses him by stroking his sensitive penis with the silky lining of the dress. She warms him up, gets him excited & eventually has him play with himself while she talks about her plans for his feminization. He's going to have to get used to the taste of cum so he has to eat up his mess at the end.
Length: 12 minutes

Crossdressed Slut For Me

mp4 360.19 MB

I want you to put on these frilly, girly things for me. These pretty panties, stockings, lingerie. I want you to practice being a sissy slut for me. I'll be pimping you out so I want to ensure you're not going to disappoint me...
Length: 13 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 Becomes Cock Sucking Cuckold

mp4 484.17 MB

Well, with a title like that & the images to match there's not much more to say. If you like cuckolding...& especially cuckolding with sissy/cross dressing cucks in chastity...throw in some ENCOURAGED BI COCK SUCKING & we've got a real winner here. Enjoy!
Length: 16 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