May 302013
Lady Anabelle Strict Dominatrix Fucking A Tranny With Strapon Dildo

Lady Anabelle dominate tranny Kitti and fucks her up the ass with a big black dildo in this video at Vintage Crossdressing

Lady Annabelle had Kitti just where she wanted her… Trapped in the dungeon and bent over so she could give her tranny slave the fucking she deserved.

Kitti was dressed up like a filthy whore in her seamed nylon stockings, multi-suspender belt and stiletto heels and ready to take strap-on punishment from her Ladyship.

Lady Annabelle was in a bitching mood, dressed in her generals uniform, her pretty face framed by a peaked cap, her waist held tight in a leather corset and her legs covered in tight, shiny latex.

Her Ladyship had a thick, black strap-on cock buckled around her hips and forced it into poor Kitti’s mouth and made her suck on it good, in preparation for where it was going next…

Lady Annabelle stood behind Kitti and grabbed her cock between her legs and milked it in her firm hand, then she mounted Kitti and forced the strap-on dildo inside her filthy, tranny fuck hole.

Kitti screamed as Lady Annabelle rode her tranny arse and thrust the huge black cock deep inside her shitter, the thick latex dildo reaming her anal passage and rubbing against her prostate felt extraordinarily exquisite.

Oh,what bliss it was, having her ladyship riding her ass and taking pleasure from it; sending Kitti wild with lustful abandon and filled with the desire to be a perfect slave to her mistress.


Sep 092008

Look who’s wearing the trousers and ordering her sissy PVC Maid around – It’s Strapon Jane!

Everybody needs their own maid, especially when you can demand what they wear and do! Jane’s very own maid does everything she demands. Having her maid dress in PVC, stockings, panties and heels, Jane makes her sissy slave bend over so she can fuck that tranny ass with her strap-on didlo!

See this movie where Jane first disciplines her maid with the cane here at Strapon Jane.

Jul 232008

A trio of Mistresses takes on our little maid jack in a 47 minute domination festival. Mistresses Kendra, Mika and Jacklyn surround the little maid in a sea of long, pantyhose clad legs as he licks up a plateful of their spit before worshiping their feet as they smoke cigarettes. He takes Mistress Kendra’s hand in his ass and then Mistress Mika fucks him with a huge dildo while Mistress Kendra finds and then jams another one in at the same time. Mistress Jacklyn uses Her strap-on to finish the job as the other two Ladies make him lick their dildos clean.

Mistress Mika has Her pussy wrapped around the face dildo strapped to little maid jack’s face as Mistress Jacklyn and Mistress Kendra are hawking and drooling spit into the clear plate. Mistress Mika makes several contributions as the plate becomes loaded with their saliva and snot. Mistress Jacklyn takes Mika’s place over his face as Kendra sits between his legs and spikes his little balls. The Ladies rotate to torment him with their high heels and tease them with their pussies.

With his cock and balls hurting from their sharp heels, maid jack is ordered around and made to start feeding from the spit plate. Mistress Mika encourages him with a crop from behind as Mistresses Kendra and Jacklyn supervise in front. He licks and slurps as Mistress Kendra replaces Mistress Mika with a red cane. Facing the Ladies now he begins foot service, working his way down the line.

Little maid jack has the taste of their shoes and toes in his mouth as Mistress Kendra announces She has to pee. Mistress Jacklyn orders him to hold the pee bowl directly over his face as Mistress Kendra pulls Her pantyhose down to her knees and squats over the bowl. After she has relieved herself, she wipes and then stuffs her toilet paper into the maid’s mouth. They make him savor the paper and then turn him and order his face into the bowl. The Ladies flip him to his back and all three light up cigarettes, using the humiliated sissy maid as their footrest.

The three Mistresses all enjoy a smoke, using their little maid as their ashtray and spittoon. Ashes, gobs of spit and finally cigarette butts go into the little maid’s used mouth hole as the Mistresses enjoy his ashtray service. All three finish their cigarettes at his expense. Now bent and tied, little maid jack has himself used by three, now topless Mistresses. Mistress Kendra stands by with an enormous rubber cock as Mistress Kendra lubes him and begins a deep prostate massage. Mistress Jacklyn scrawls obscene writing on him in lipstick.

Mistress Kendra has manually stretched out the little maid’s ass and now Mistress Kendra fills the hole with a giant dildo up to the balls. Mistress Jacklyn has put on Her strap-on and sits in front, forcing him to suck cock while his ass is filled. Mistress Kendra decides to see if Her hand will fit along with the cock and this very much stimulates the little maid. Mistress Kendra produces a second dildo and now She and Mistress Mika both have dildos in the sissy maid at the same time. Mistress Jacklyn then uses Her strap-on to fuck him as he licks both dildos clean for Mistress Kendra and Mika.

Find out how you can watch Maid To Order and other sissies being dominated by females for a little as 8 cents per minute at Fetish Movies