Whitney Wright is a very hot and extremely slutty student in Tony Orlando’s class. He’s trying to play it cool while she fingers her own pussy while sitting on her desk in his classroom. The Principal (Britany Andrews) storms into his class and confronts him about fucking his students. He swears he would never… Then Principal Andrews tells him it’s ok, he should fuck his hot student. Whitney spreads her legs wide on her teacher’s desk while Principal Andrews shoves Tony’s face in her young pussy. Whitney asks, “Principal Andrews, is this like the last teacher who you told me to fuck and then we cut his balls off after…?” Right then Whitney clamps her thighs around her teacher’s neck, trapping his mouth on her pussy. Principal Andrews explains that he will be fucking his student, but after he cums they will be destroying his balls for good… Whitney begs for his cock, and smiles when he quickly wants to cum. She knows her young pussy is too much for him to handle. Every time he gets close to cumming, Principal Andrews pulls him away and the two ladies torture his balls with hard squeezes and bites. Eventually they let him cum all over her pussy. They make him lick it all up while they discuss a few terrible ways to castrate him in the shop class with power tools.

All Tony wants to do is watch his game which would be fine except the big game happens to be on Valentines day and his woman, Penny Barber, expects to be wined and dined.

Jet Setting Jasmine sits at her leather throne looking gorgeous and powerful. Graveling at her feet in a latex hood is Tony Orlando. She makes him clean her black high heeled shoes with his tongue and so he licks them clean including the soles. Jasmine tells Tony to remove her shoes and worship her stocking covered feet. He sniffs and licks them and she shoves them in his mouth. Next he's told to remove Jasmine's stockings and he does it slowly and continues licking her now naked feet and sucks her toes. Jasmine shoves both of her feet into his big mouth. She makes him remove his leather jock and she presses her toes against his cock and scolds him for producing pre-cum without permission. She feeds it to him with her feet and he tells her he's sorry. She commands him to sniff and to lick her underarms and as he does, she traps his nose and mouth in there, gets him in a headlock and squeezes. In the next scene, Jasmine wields a giant dildo attached to her strap-on. She has Tony bent over a leather padded cage in a black straight jacket, with a blindfold covering his eyes and a ball gag in his mouth. She flogs his ass with a flogger in each hand and after his ass turns pink, she slides the huge dildo into his asshole and fucks him deep. Jasmine puts Tony on the floor with his ass in the air. She slides on latex stockings, lubes them up and shoves almost her whole foot into Tony's ass. He backs up onto his Goddess' foot, trying to fit the heel in, and she takes her foot out and makes him clean it off with his mouth for being such a greedy slut. Next, Jasmine has Tony on his back, on top of a padded table, covered in layers of plastic wrap, unable to move. She cuts a hole, made only for his cock and pulls it out. She lubes up a sounding rod and shoves it deep down Tony's urethra and fucks his pee hole with the metal rod. After that, she relieves her full breasts on to Tony's face, squeezing them and showering him with her breast milk. He frees one of his hands to jerk off and cums while them warm milk rains from his Goddess.

Tony Orlando is in the hospital. Dr Charlotte Sartre tells him that he doesn’t have long to live. He asks if there is anything that can be done and she tells him there is one very risky procedure…. It involves him getting fucked hard in the ass with a huge strap on while someone sits on his face… Fabiana Fox strolls in with a giant pink strap on and slides it in his hole while Bunny Colby assists with the face sitting and also some feet in his mouth.

Why You Shouldn’t Cheat on Pissed Off Hotties Olivia Jay and Mia Molotov. Olivia Jay and boyfriend Tony Orlando are enjoying a quiet evening of basketball and chill. But Tony keeps getting text messages, which he insists are from GrubHub about their food delivery. Olivia is suspicious, so when Tony goes to the door to get the grub, she checks his phone — and discovers he has a side piece! She arranges a meeting with other girl Mia, who insists she had no idea Tony wasn’t single. The two women vow revenge. On his birthday, Olivia blindfolds Tony and takes him to a secret location for an extra special surprise treat. But once they arrive, Tony is shocked to see he’s in a dungeon, and Mia is there, rope in hand and really angry. The women bind Tony to a metal chair and proceed to torment him with crops, flogger and clothespins on his dick and nipples. Tony thinks his punishment is almost over, but no! Next thing he knows, he’s tied to the top of a cage with ass up for easy access with paddles and strap. Once his butt is good and red, it’s time to attach him to a spanking bench. Mia and Olivia return wearing strap-ons, and pound him on both ends till he’s helpless and drooling. Finally, Olivia lets him see her pussy one more time before kicking him out of her house — and then she squirts all over his face before leaving him there for the dungeon Mistress to find.

Lola Fae lives with Tony Orlando. He gets really gropey and grabby with her and she’s sick of it. She dresses up in a tight bodysuit with shiny tan pantyhose and sneakers because she knows it will drive him crazy. Then she dances in the kitchen and waits for him to notice her. When he grabs her ass and puts his hand on her throat she smiles and grips his balls hard then kicks him in the chests and puts him on the floor. Lola explains that from now on, he won’t get to use her pussy anymore. She’s going to use his. She pulls out a giant pink strap on cock and tells him that it might be rough at first, but he’ll be begging her for more dick soon. When she’s balls deep inside him she tells him that while he’ll never get her pussy again, he will be watching her new boyfriends fuck her a lot. If he’s good, he can lick their cum out of her perfect pussy when they’re done. She proceeds to fuck his brains out all over the kitchen and make him call her Daddy by the end of it.

When latex whore Tony Orlando comes sauntering into Julia Ann's dungeon, he's convinced he knows it all. He's convinced he's seen it all before. Like all men, Tony is cocksure and entirely confident that he knows exactly how best to serve his mistress, without ever listening to what his mistress actually wants and needs. Lucky for Tony, Mistress Julia is patient and kind, and willing to teach her self-assured bitch boy his place in the world. In a deliciously sultry voice truly unique to the latex-clad goddess, Julia Ann humiliates Tony - breaking him down slowly and methodically. Tony endures over-the-knee spankings, licks in between every single one of Mistress Julia's stocking enshrined toes, and is smothered in her voluminous, soft, and radiant tits before being edged into psychological oblivion. Julia then binds her pet, parading him on elbows and knees for her pleasure before delivering a heavy dose of corporal. Tony's cock begins to drip as Mistress Julia then teases his greedy pink hole, plunging her gigantic dick suddenly into her meat toy, drawing deep moans and yips from the nasty slut gobbling up every inch. After thoroughly fucking Tony in doggy until he gapes and cries out from the overwhelming sensation of being entirely full of cock, Mistress Julia mounts her whore's face, using Tony only for his tongue. Fully immersed in her own pleasure, Mistress Julia smothers Tony with her divine ass, giving him taste after heavenly taste of her glorious wet cunt. Julia then uses her other pussy - her foot pussy - to edge Tony, who thrusts desperately between her delicate arches, trying to cum as Mistress Julia taunts and laughs at him. Finally, finally, she allows her pet to release his disgusting, sticky shame all over her divine toes. Tony, of course, has to lick up every single drop.

Hired for a photoshoot, Helena Locke and Tony Orlando are both dressed in tight shiny latex. The photographer snaps pictures as they portray the roles of Dominatrix and Submissive. Tony, head-to-toe in all black latex has his hands tied to a St. Andrew's Cross. Helena Locke, dressed in a sexy blue and black latex outfit, holds a thick chain attached to Tony's neck. When the photographer takes a long break, Helena takes advantage of Tony's predicament and indulges in a little play session for real. She teases his cock and rubs it through his latex pants. Helena heads over to the table full of toys and grabs the leather flogger. She flogs his body and sticks her hand down his throat. She pulls down Tony's latex pants, grabs his balls and tells him that it looks like his tiny male brain. Helena slaps his dick with her hand and then with the flogger. She teases his cock with her mouth then bites down hard. After that, Helena goes to the table again and returns to Tony with a leather "balls gag". Instead of attaching the belt around someones head who is then supposed to be gagged by the balls, Helena adds weights to it and turns it into a ball stretcher. She kicks the weights with her latex boots and they swing like a pendulum. Helena rubs her bare ass on Tony's pathetic cock and gets it dripping with precum. In the next scene, Tony is stripped naked and tied face down with rope, to a leather stool. A spreader-bar keeps his legs apart and a ball gag keeps his mouth quiet. Helena enters his ass with her huge strap on and fucks it well. She grabs the Fucksall and with a big lubed up dildo at the end of it, she slides it in his ass and pulls the trigger. Tony's eyes get big as he gets his ass rammed harder and faster than he ever has before. Then Helena gets a glove and shoves her whole fist in Tony's ass. In the final scene, Helena lounges on a leather bench while she makes Tony watch her get fucked by a fucking-machine. She tells him to get on the floor and lick her feet while she gets fucked. Tony deep throats her foot and licks all her toes while he watches her climax from getting machine-fucked. Tony cums on her feet and she makes him lick it off.

Aiden Starr teaches all about pegging: how to fuck a male with a strap-on dildo in the ass. This tutorial discusses preparation for the male, selecting and wearing a strap-on, anal sex safety and warm-up, prostate play, butt plug training, pegging techniques, first-timer considerations, advanced tips, and cleanup.