Educating A Bitchboy: Episode 4 - Last Chance Waller
Cast: Jason Miller ,Bobbi Starr
Genres: Fingering ,Slave ,Orgasm Denial ,Athletic ,Femdom ,top ,CBT ,Pegging ,Chastity Play ,Corporal Punishment
Video language: English
Jason Miller desperately wants to serve Maitresse Madeline and he will get his chance but not until Mistress Bobbi Starr has one last day with him, and good thing because he really needed it. Mistress Bobbi Starr teaches Jason what true submission to a women is all about. He goes through a transformation and you can tell in the closing interview. This shoot was extremely difficult for Jason. Strict bondage, CBT, objectification, humiliation, strap-on ass fucking, caning, flogging, ass worship then stuffed back into chastity! Does this get him in line for the next day when his dreams finally come true and he is allowed to serve Madeline? Tune in to Jason’s final day of training and find out!
Format: mp4
Duration: 1:02:19
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps
File size: 681.0 MB
DOWNLOAD FROM FILESMONSTER: Educating A Bitchboy: Episode 4 - Last Chance
The prospective maid Kitwe
Release Year: 2016
Studio: Captivechrissymarie
Genres: BDSM, Spanking, Fetish, Bondage, Glamour
I run a local housecleaning business on the side, but things have been particularly slow lately, so I went on a few new websites and after some searching found an ad for someone needing a maid on a regular basis. This could be a great steady income, but he requires and interview before he can guarantee the job. I arrive right on time, dressed ready to do some cleaning in my shorts, tank, sneakers and bandana to keep my long hair out of my face when I'm working. I knock and an attractive man answers the door. We seem to get along well as we start discussing the job, but he does mention that he has some strange requests for his maids, which is why he pays so highly. I tell him no problem, with my experience I'm sure it's nothing I can't handle. I get to work cleaning the dining area and I must admit it's a little disconcerting to be watched so closely, but he reassures me that I'm doing a great job. Then he brings up his first request: He likes his maids to be nude while cleaning. I hesitate as I am not that type of housecleaner, but he mentions he knows my business is struggling and that I really need the money. Unfortunately I really do, so I decide it can't be that bad, as I strip down to just my socks and get back to work. Next he brings up another surprise, that after his maids are finished cleaning, he likes to tie them up for his viewing pleasure! This really makes me uncomfortable, but I don't want to lose the cash now that I did all that work, completely naked, that would be so humiliating! I tell him it's a really strange request, but I guess I'll try it. He throws me a rope and asks me to start tying my ankles, before going on to tie my wrists and thighs for me and cleave gag me with the bandana off my head! He moves me back to the living room and orders me to struggle while he watches me. Then he decides he wants to see my bare feet, so he removes my white ankles socks to expose my soles. I keep struggling but really start to get tired of it and ask to be let out, but he doesn't listen, and instead starts fondling me! This was not part of the agreement! I try to fight it, but being all tied up, I can't really do anything about it. Then his touch starts to involuntarily arouse me, and I start to think about how it is kind of hot to feel so helpless as this man controls me. My moans start to turn less distressed and more pleasured as he gropes me, and before I know it he has me under his spell and I'm telling him that I'm a very bad maid who needs to punished!
In Part Two, it's time for the next part of the interview and to see how well I can endure a harsh punishment. I've spent the majority of the interview up to this point feeling quite uncomfortable with the whole situation. I even asked to be untied at one point, however he did not let me go and instead started fondling me until I reached the point where I was under his control and actually started to enjoy it, begging him to punish me for being a naughty maid! He bends me over on the couch and starts whipping me with a flogger on my ass and thighs. The combination of pain and pleasure is unlike anything I've ever experienced. As he gets rougher and rougher, my faint moans start to turn more agonizing. I know if I can just endure this last part of the interview, I will definitely get the job, and I really need the money. If I have to endure it, I'm going to try to enjoy it as well. He moves on to whipping ass and bare soles before flipping me over on my stomach and giving me a good old fashioned hand spanking to finish it off, leaving me with a bright red behind and nearly in tears, but then he gives me the great news that I'm hired and will be back same time next week. I ask him if perhaps I'll actually do some more cleaning next time, and he says we'll see about that!
Format: mp4
Duration: 22:15
Video: 1920x1080, AVC (H.264), 8388kbps
Audio: 241kbps
File size: 1.4 GB
DOWNLOAD FROM FILESMONSTER: The prospective maid
Sissy Maid Slave Rankin Inlet
In the ever-expanding world of sexual fetishes, feminization is quickly gaining in popularity. Acquiring a sissy may be all the rage, but getting one to do all your bidding can prove to be tough work. You have to be a determined Mistress with a firm hand like Dita Rose, the no-nonsense Femdom of Sissy Maid Slave. For those curious, this Transfetish Production is a very thorough look into the life of a sissy maid. From training to complete servitude, this movie has it all.
If you’ve ever had an interest in sissification, the talented young Mistress Dita gives us a firsthand look at how to properly dress, train and handle your own sissy slave. Her prey is the sexually confused Jade Madison. He’s posing as a computer repairman and claims to have a girlfriend, but Dita can see right through that act. She knows he was born to live his life as an obedient little sissy slut. Watching Jade become a submissive tranny is a long and, thanks to Dita, very enjoyable journey. If you’re a fan of domination and humiliation, you can’t pass up these first three scenes, which deal with the submale’s intense training.
Not one to waste any time, we dive right into the transformation. Stockings, a new frilly outfit, some makeup – they all play a big part in turning this average straight male into a sissy. As part of his girly change, Jade is also thoroughly educated on how to please his fickle Mistress. This includes how to properly clean her filthy heels with his tongue and the daily upkeep of the house, which as a sissy maid he’s obligated to do everything a regular maid would only in a kinkier way. For example, for sissy maid Jade, cleaning a toilet isn’t a simple act. No, in the hands of Dita it’s a fetish treat, as he’s to clean it with a toilet brush attached to his mouth gag. It’s the only way to ensure a proper cleaning. Of course no one ever said training a sissy was easy. These worthless subs are bound to mess up. But don’t worry; Dita knows that when a sissy makes a mistake, the only way to correct him is with an intense spanking session.
Jade endures a lot, but ultimately becomes a sissy maid Dita can be proud to show off. She invites Mistress Ashley and her husband Damian over to check out her new acquisition, and the couple are only too eager to put him to the test. Jade is clearly nervous, but she’s been properly trained. She knows she has to do anything to make Dita’s guests happy, and that includes getting on all fours to suck on Damian’s cock. When she first pulls his dick out it’s small and flaccid, but with a few strokes of her tongue it soon grows to fill her mouth nicely. Since it’s not massive in size, Jade is able to properly deep-throat him. That may not seem like a difficult task, but it’s a little more challenging when you have his wife fucking your tight sissy ass with a strap-on. Mistress Ashley is outstanding at doing just that while she barks orders on how to properly suck her husband’s cock. Jade does outstanding work and is rewarded nicely with a mouthful of cum. Pleased with the obedient sissy, the couple decide to take her with them on their vacation.
The rest of this film is dedicated to the various tasks Mistress Ashley gives their weekend sissy. She’s much more aggressive than Dita, but Jade handles herself nicely. From massaging her new Mistress’s tired feet to allowing herself to be suspended as she gets probed with various anal toys, Jade is a model submissive. She takes on every task with gusto, but she’s really at her best when taking care of Damian. The beefy straight man makes a last appearance at the end and we get another chance to watch Jade suck on his cock. Jade really is a talented cocksucker, giving Damien another mind-blowing orgasm.
Cuckolding, bisexual acts, – Sissy Maid Slave touches on all these fetishes and many more. Sissification may not be for everyone, but this feature offers plenty of titillating acts to satisfy all fans of kink. Exploring a new fetish is always an exciting adventure, so jump right into the action with this quality Transfetish production.
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Format: avi
Duration: 1:02:47
Video: 720x480, XviD, 1263kbps
Audio: 125kbps
File size: 644.3 MB
DOWNLOAD FROM FILESMONSTER: Sissy Maid Slave
Mistresst - Anal Abuse And Humiliation Pine Lake
Release Year: 2016
Studio: Mistresst
Cast: Mistresst
Genres: Female domination
Video language: English
This is probably the most authentically abusive anal vid I´ve done. I had instructed this slave to train his own ass to take a larger toy. He swore he was ready, he begged & begged me to film with him. He even sent me money to show he was serious about being a good film slave. He whines about the pain as I fuck his ass. He keeps trying to get me to stop & each time I get him on his knees & make him suck his ass juices off the cock (ass-to-mouth) as punishment. I verbally degrade him, his small worthless cock & his lousy performance. I banish him & tell him I´ll never see him again. cruel, cutting humiliation.
Format: mp4
Duration: 15:00
Video: 1280x720, AVC (H.264), 3762kbps
Audio: 153kbps
File size: 430.8 MB
DOWNLOAD FROM FILESMONSTER: Mistresst - Anal Abuse And Humiliation
Stefanos' Brunch Chenango Bridge
Cast: Dylan Ryan ,Beretta James
Genres: bottom ,Discipline ,slim ,Humiliation ,master ,Rough Sex ,brunch ,mixed ,BDSM ,natural boobs
Video language: English
The House has another Brunch filled with amazing BDSM debauchery. Tramp and pistol are punished in front of the guests by the Steward, and tramp is made an example of. The party moves to the lounge, pistol is put in a cage and the guests are allowed to have their way with her while tramp services another guest.
Format: mp4
Duration: 57:54
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps
File size: 632.9 MB
DOWNLOAD FROM FILESMONSTER: Stefanos' Brunch
Lady Nala Screams and Begs For More From Mona Wales Lake Arrowhead
Cast: Lady Nala ,Mona Wales ,Juan Lucho
Genres: Blowjob ,Stocks ,Submission ,Humiliation ,Corporal Punishment ,brunet ,foreskin ,Public ,BDSM ,Brunette
Video language: English
In a field near the coast on a bright and sunny day Mona Wales leads Lady Nala toward a dilapidated house covered in graffiti. Nala stands firm as Mona flogs, shocks her with a zapper and uses clothespin zippers on her soft flesh. She teases orgasm after orgasm from Nala in the hot sun! Soon, Mona tires of this teasing and decides to make a spectacle of Nala in front of her friends at Rosas5, a local BDSM club. The crowd is ready to see this young lady squirt as they do not get to see her dominated often. Nala is suspended by her ankles from the ceiling and as she is shocked and spanked her friends and guest chant, ready to see her get dicked down like the slut she is! Juan Lucho is ready and face fucks the little beauty until spit is running down her forehead, she is hungry for more and the guests pull out cupcakes to smash on her tits, ass, and face while Juan continues to feed the hungry cumslut his fat cock. Nala is taken down from the ceiling and thrown into the stocks where she will stay still as she is fucked long and hard from behind. Her friends hold her face in their hands as they tell her she fucks better when Juan cannot see her face, instead, a guest rides on her back and teases Juan while her uses Nala’s wet pussy. She begs to be let out from the stocks and once she is, the real work begins! They push her body to the limit commanding her to stay strung while she bounces up and down on Juan Lucho’s throbbing dick, as the crowd works into a frenzy Juan pushes her down and makes her spread her big ass so he can cover her pink hole with cum. Mona pulls her into the street where she is made to spread her messy cheeks by the street so the world can admire her from the inside out, as passersby look on in disgust, Nala is proud to be such an exposed whore!
Format: mp4
Duration: 55:33
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps
File size: 608.8 MB
DOWNLOAD FROM FILESMONSTER: Lady Nala Screams and Begs For More From Mona Wales
Shocked Achaguas
Cast: Calico
Video language: English
Calico's cable-tied, bagged, dragged into the basement, and humiliated as PD trains her to be his dog. Shackled to the floor of the basement, she has to stay in the doggy position. Disorientation is one of the most difficult feelings. Putting someone in a position where they cannot see their own body and cannot touch their own face is very disorienting. Calico is just a body and just a head. What a sexy body and beautiful head. She can't see what is about to happen to her body. She has to wait, feel it, process it, and recognize that it's pain. It's so much worse than pain all on it's own. The dusty old mattress. It's seen a lot of pussy in it's time. What's one more? Calico is strapped down, latex hooded, and her breath is restricted. Her slit and asshole are perfectly exposed for use. So inviting.
Format: mp4
Duration: 58:08
Video: 1920x1080, AVC (H.264), 4654kbps
Audio: 119kbps
File size: 2.0 GB
DOWNLOAD FROM FILESMONSTER: Shocked