Latest updates featuring Tommy Toscano

Leena Sky in 'Inadequate Slave'

Leena Sky - Inadequate Slave

Mistress Leena?s boots are filthy, fortunately, she has Tommy Toscano to lick them till they shine. When he?s done with the boots, Mistress has a strap-on that needs cleaning too. Once everything is clean, Mistress warms Tommy up with a. Cane and flogger before checking on his anal training by fucking his ass with her strap-on. Not happy with how his training is progressing, she makes him beg for her to use a larger cock on him and then flogs him until she gets the obedience she deserves. But Tommy?s misdeeds continue in his off hours. Mistress Leena catches him jerking off in the shower, which is strictly forbidden. And now he?s due for a humiliating ass pounding with her big strap-on as he struggles to keep his footing under the running water.

Kiki Daire in 'Cuckolded by a Sideshow Carny'

Kiki Daire - Cuckolded by a Sideshow Carny

Cuckolding with sword swallowing and we mean that literally! Kiki D'Aire is fed up with her boring husband Tommy Toscano. It seems that he would rather pay attention to a book than his incredibly sexy wife. She got all dressed up to go out on the town on a Friday night and he just wants to sit there and read. Realizing that Tommy's not going to be any fun, she calls up her girlfriend and they decide to got to the carnival that's in town.Later Tommy is fast asleep on the couch when she returns home, tipsy and accompanied by a carny named Murrugun the Mystic! She is going to have fun tonight, with or without Tommy. Kiki is OK with having fun in front of her husband, and Murrugun doesn't seem to mind, but Tommy is all upset, because he's a square! Kiki tells Tommy to shut up and she and Murrugun start making out. Then they decide to show Tommy some tricks. Murrugun pulls out a long steel needle and shoves it right through his bicep! At this point poor Tommy doesn't know what to think. As entertaining as all of this is, Kiki has a different kind of trick in mind. She grabs Murrugun's belt and starts rubbing his cock through his pants, then, to Tommy's horror, she pulls it out and makes it disappear- right down her throat! Kiki and Murrugun decide to have' a contest to see who can swallow more. As she takes his cock balls-deep, he pulls out a sword, 22 inches of gleaming carbon steel and proceeds to swallow it to the hilt! Kiki is choking on his cock, but Murrugun didn't gag, so he wins! Now its time for him to collect his prize! Tommy is stunned as she keeps sucking his rock-hard cock. With her mouth fresh off the cock, she gives Tommy a nice, deep kiss. She peels off her dress and drapes it over her pathetic husband's head before bending over the end of the couch. Ever the showman, Murrugun slides the sword back down his throat and slides his dick deep into Kiki's soaking wet pussy. Murrugun lies back on the couch and Kiki rides his pole until she squirts! He reaches up and grabs big, beautiful boobs as she bounces on his lap. Meanwhile, Tommy just watches, doing nothing!Then, Kiki pulls out a dildo and waves it in front of Tommy's face. As Murrugun fucks her, she fucks Tommy's face with the dildo. At this point Tommy doesn't know what to think as Kiki orders him to fuck it with his tongue, so he obeys. Kiki starts screaming in ecstasy as Murrugun fucks her harder and faster. She makes Tommy admit that he's a good little cocksucker before she rams the dildo back into his mouth! Tommy is shocked when Murrugun eats Kiki's pussy, since he never does that. When Murrugun states that Kiki is one of the top-five dick suckers in the country, she gets offended and starts slapping his balls- she wants to be number one! She has Tommy go back to sucking the dildo while she climbs on top of Murrugun and takes him for a ride. Finally it's time to get her carny off. Kiki makes Tommy watch as she strokes Murrugun's cock, squeezing his balls and jerking until he shoots his big, hot load right into her mouth. He has her spit his cum into his hand and then rubs it all over her well-fucked pussy. She teases Tommy with her cum-filled mouth before taking Murrugun off to bed.

Kiki Daire in 'Creepy Gynecologist Gangbang (3 of 3)'

Kiki Daire - Creepy Gynecologist Gangbang (3 of 3)

Dr. Dee Severe, nurses Ivy Thornton and Ashlee Graham and patient Kiki D'Aire are teaching Dr. Tommy Toscano a lesson! When they are done with him he will no longer be rude to his partners, sexually harass his nurses or his patients. As Kiki fucks his man pussy asshole, Ashlee explains that she's hidden his clothes, and if he ever does get to leave, it's going to be naked. The ladies slap his pathetic little cock as Kiki drives her much bigger strap-on in and out of his ass. They make him squeal like the male chauvinist pig he is, and when his oinks aren't good enough, Kiki fucks him harder, until they are acceptable. Dee sticks another dildo in his mouth, but that doesn't mean he can stop oinking. Soon his mouth is stuffed with three plastic penises. After making him beg to stop, they give him a plant to cover himself with and send him on his way! (Part 3 of 3)

Kiki Daire in 'Creepy Gynecologist Gangbang (2 of 3)'

Kiki Daire - Creepy Gynecologist Gangbang (2 of 3)

Dr. Dee Severe, nurses Ivy Thornton and Ashlee Graham and patient Kiki D'Aire have ganged up on Tommy Toscano, the worst gynecologist ever! They are teaching him a lesson for being rude to his partners, sexually harassing his nurses and his patients. Nurse Ashlee orders him to suck her strap-on cock while nurse Ivy rails him from behind. Ashlee makes him gag on her plastic penis, but the ladies aren't convinced that it's real. Kiki wants to see more passion, after all, he said that he enjoys anal sex! They tease and humiliate him, letting him live out his dream date of having all four women at once, only this dream is his worst nightmare! Kiki comments on how pretty and loose his hole is as she prepares to drive her dildo into his waiting hole!

Kiki Daire in 'Creepy Gynecologist Gangbang (1 of 3)'

Kiki Daire - Creepy Gynecologist Gangbang (1 of 3)

Tommy Toscano is the worst gynecologist ever! Not only is he rude to Dr. Dee Severe, he makes nurse Ivy Thornton do menial tasks that aren't part of her job – as well as sexually harassing hottie nurse Ashlee Graham. Not to mention, he gives patient Kiki D'Aire a wildly inappropriate breast and pussy exam!But when Dr. Severe discovers evidence he's also perpetuating Medicare fraud, the women get together – and get even! They pretend they're all going to seduce Dr. Toscano, but once he's naked, they whip out their strap-ons. The doctor is going to get fucked, but good – just not in the way he had in mind! To start with, he gets to perform a humiliating strap-on blow job, as the nurses amuse themselves by seeing how many dildos he can get in his mouth at the same time. And Dr. Severe is slamming his ass, so all his holes are violated. And they're just getting warmed up!

Holden Holliday in 'Strap On Idol (Part 3 of 3)'

Holden Holliday - Strap On Idol (Part 3 of 3)

The winner is crowned! Our pegging epic concludes as one more contestant, Jimmy Broadway, gets put through the semi-final paces by super critical Simon(e). Then, the final four gather and the judges pick the two finalists. The judges table is cleared so everybody can ram both finalists' holes with ease. The contest seems pretty evenly matched until one of the guys claims he can perform a double anal - and does, all the while sucking yet another dildo.

Holden Holliday in 'Strap On Idol: The Semi-Finals (Part 2 of 3)'

Holden Holliday - Strap On Idol: The Semi-Finals (Part 2 of 3)

Our AVN nominated feature continues with pegging, pegging and more pegging! The semi final round of Strap On Idol brings our more promising contestants on stage, stripped naked and displayed on a spanking bench, their assholes in a prime position for reaming. The judges take turns testing the eager guys on their dildo blowjob skills as well as seeing how well their butts respond to getting fucked for real. The big surprise turns out to be Slut Bottom Chris, who brings his own huge dildo to get fucked with. (behind the scenes note: Chris was actually hired to be one of the extras who doesn't make it past the first round, and turned out to be one of our regular performers for years.) Overconfident Tommy Toscano barely made it to the semi finals, but redeems himself here. Who will go on to the finals, and the strap-on orgy? (Parts 2 of 3)

Holden Holliday in 'Strap-On Idol (Part 1 of 4)'

Holden Holliday - Strap-On Idol (Part 1 of 4)

Introducing vintage features! This AVN nominated parody of OG American Idol stars Zoey Holloway as Simon Cowell, director Dee Severe as Paula Abdul and Sinnamon Love as Randy Jackson. In round 1, the judges check out the first crop of contestants by making them strip naked, bend over and spread their asses for inspection. The judges wield dildos and butt plugs to determine who is worthy of going on to the next round. Some pass inspection, some prove over-confident, and some just didn't pay attention when they were applying. And that's just the beginning - in subsequent rounds the lucky semifinalists get their butts reamed by the judges, while the finalists participate in a full on pegging orgy. (Part 1 of 4)


AJ Applegate in 'Disco Cuck (Part 2 of 2)'

AJ Applegate - Disco Cuck (Part 2 of 2)

Old fashioned 1970's bar owner Tommy thought he was hiring a bartender so that wife A.J. could stay home and get pregnant. But once A.J. got a look at hot stud Moe, she immediately had other plans, and now the two are fucking hard and fast. Tommy is worried that Moe's giant pole is going to hurt his wife, but all she feels is pleasure. They move over to the lounge so she can ride him, and then she gets on her knees, mocking her husband as Moe pounds her from behind. As they fuck A.J. begs Moe to turn her into a Cock slut! Finally Moe pulls out and A.J. starts stroking his monstrous cock. She tells Moe to shoot a big, fat load all over her, and when he does she shocks Tommy - and answers the question of, how did T.J. come into the world?(Part 2 of 2)

AJ Applegate in 'Disco Cuck (Part 1 of 2)'

AJ Applegate - Disco Cuck (Part 1 of 2)

A.J. and her son T.J. have come to the cemetery to pay their respects to Tommy. Now that Tommy is gone, T.J. wants to know who his real father is, and that's where our story begins. Flashback: It was the 70s. Tommy Toscano and A.J. Applegate own a small club in the Valley. Tommy is happy with their situation, but A.J. has dreams of being the Studio 54 of Van Nuys. When Moe Johnson comes in to interview for a bartender's position, something clicks. Moe is a man with vision and enthusiasm, and A.J. doesn't care what Tommy thinks, he's hired. Its obvious that Moe and A.J. are hitting it off, and there's nothing that Tommy can do about it. He's made to stand back and watch as Moe takes charge, spanking A.J.'s beautiful round ass. She makes Tommy kneel behind her and worship her shoes and feet as she and Moe make out. When Moe pulls down his pants and reveals why they call him The Monster, A.J. gets excited and Tommy starts to panic. She licks up and down the shaft of Moe's giant cock before taking as much as she can in her mouth. She strokes and sucks and Tommy has to watch. How far is this going to go? Moe takes charge, smacking A.J.'s luscious ass with his huge cock. She has Tommy help her take her shoes and jeans off, then humiliates him further by bending over in front of Moe so he can fuck her tight little pussy. (Part 1 of 2)