Tiny-Dick Cuckold Sissy Boys Watch Their Wives Fuck Multiple Black Men

Latest Updates from Cuckold Sessions (Page 5)

Brooke Wylde - Cuckold Sessions

Brooke Wylde - Cuckold Sessions

29th September - Brooke Wylde loves to go clubbing, and she loves to bring her man along. Her favorite kinds of clubs are the "black clubs", which always makes her man nervous. "Honey, I'm afraid I'm going to get my ass kicked," is something Brooke's man has said more than once. And more than once, Brooke laughs and tells him to "grow a pair!" Today's situation isn't any different. Once in the club, Brooke's man is pushed and shoved and ridiculed while Brooke makes new friends. She loves all the attention she gets dressing like a slut and strutting her stuff, and sure enough, in no time she's back in the VIP section letting anyone and everyone have their way, while her man tries to simply survive. ...Read More
Alena Croft - Cuckold Sessions

Alena Croft - Cuckold Sessions

27th September - Alena Croft and her Hubby, Bob, have an interesting relationship. Bob is in his mid-fifties, and honestly, he can no longer keep up with his hot, horny wife. He quit trying years ago. Now he's accepted other men will enjoy her, so why not enjoy himself as Alena enjoys herself? Here's their trick: they call repairmen and have them come check whatever it is they say is "broken": the refrigerator, the AC, the pool pump...whatever. As Bob's showing the workmen around, they'll always catch Alena doing inappropriate things. Then they size up the workmen's reaction, and if Alena and Bob get a "good feeling", Alena makes the next move. Just watch and see Alena and Bob work their magic on today's plumbing crew! ...Read More
Brooklyn Chase - Cuckold Sessions - Scene 2

Brooklyn Chase - Cuckold Sessions

26th August - Brooklyn Chase loves her hubby very much, but a girl has needs, and Brooklyn's are generally big and black. Hubby's rule is as follows: as long as he can watch, the dudes are big, and they're black, then he's ok with Brooklyn being dicked down. He gets a little nervous when Brooklyn is hooking up with "randoms" on line, and Hubby can get really nervous when Brooklyn drags him to sketchy neighborhoods to help secure her "Bulls". Once back home, safe and sound, Hubby takes delight watching his lady being pleasured, and today's his lucky day! Sloppy seconds! Cause there ain't nothing better than fucking a very fresh creampie, unless, maybe, it's watching your wife taking a big facial from the other Bull. ...Read More

Maddy Oreilly - Cuckold Sessions

Maddy O'Reilly - Cuckold Sessions

17th August - They're always up to something kind of stupid. Take Cuckold Charlie. He loves sports. The only thing he loves more than sports is gambling on sports. He calls most of his bets "locks" and "easy money". Then why does he owe the bookie 10 Large? Trust me, The Bookie is tired of chasing Cuckold Charlie around for his money. After a sound beating, it's on to Cuckold Charlie's house, where, Charlie claims, is all the money he owes The Bookie. Once there, however, there's no money. There is his girlfriend, Maddy.Maddy's shocked to see what's going on. She thought Charlie was all done betting. Charlie's such a degenerate gambler, he's going to be OK with Maddy's mouth, pussy, and ass acting as "the vig" until Charlie comes up with some hard cash. Does it really surprise you, too, that Maddy's got some skeletons in her closet? They're big, black skeletons! ...Read More
Jasmine Jae - Cuckold Sessions

Jasmine Jae - Cuckold Sessions

5th August - Swingers. They're everywhere. Just ask Isiah Maxwell. He's just wrapped his first day on the job, and his new boss, Dominik, is going over how to close up shop when he drops the question: "hey, want to come over for dinner and drinks and you can meet my girl?" Isiah's new in town, so why not? What Isiah doesn't know is he's part of a set-up. Dominik and Jasmine have been searching for a new play partner, and specifically a black play partner. Before Isiah can shut off the lights and lock up the place, Domink's already instructed Jasmine to get on the tight, slinky dress, the hot, black lingerie, and get ready! There's a dinner guest tonight, and it's about to be one dinner date Isiah's never going to forget! ...Read More
Dava Foxx - Cuckold Sessions

Dava Foxx - Cuckold Sessions

13th July - We're all a little "off", especially if we're here, watching cuckold porn. This is absolutely OK, too, as one of our frequent cucks -- Ciccle Cixx -- is about to discover. He started seeing a therapist, Dr. Dava Foxx, to see if this whole cuckolding fetish he has is "normal". He's explained to Dr. Foxx about his obsession with interracial porn, as well as his constant worrisome behavior about things like his girlfriend cheating on him and his small penis. Dr. Foxx agrees with him that it's not normal...and all those behaviors are OK. Let's face it, the world needs cuckolds, so after Dr. Foxx drills that into Ciccle's brain, she calls in her assistant, Dr. Moe "The Monster" Johnson, and just like that, a typical therapy session turns into a not-so-typical cuckold session! ...Read More
Harmoni Kalifornia - Cuckold Sessions

Harmoni Kalifornia - Cuckold Sessions

2nd June - Oh, what these whacky cuckbois do to have a Cuckold Session! Take Jack, for instance. You might remember Jack as the overzealous fan during AVN's. Well, he's back, and he's back because he drove a few days, on his own dime, to join us for another session. This time it's with The Queen of Spades herself, Harmoni Kalifornia, and World-Class Bull Shane Diesel. Jack gets off on the wrong foot, as most cucks do, by trying to wank his teeny-tiny dinky. It might be one of the smallest ever seen here, and after lots of ridicule, Jack still insists on jacking off. Harmoni puts a stop to that by forcing cuck to strap on his male chastity device, and after that, all best are off. Harmoni and Shane put the whimp through all sorts of embarrassment and humiliation before they force poor Jack to perform the ultimate act of humiliation -- The Clean Up. Today Jack asks for permission to beat his tiny meat after clean up, and what happens here is just as humiliating as the clean up. Poor Jack! Did we mention he wants back...for more?!? ...Read More
Mena Mason - Cuckold Sessions

Mena Mason - Cuckold Sessions

22nd May - Meet Mena and Ciccle. They're "life-stylists". They live the cuckold lifestyle, and they're a very happy couple. Ciccle, who's got a dick that could never, ever satisfy Mena, knows his place in the relationship. He's there to support Mena and the quest to keep her satisfied sexually. So when Mena asks for Ciccle to accompany her to a business meeting, he knows it goes way beyond a "business meeting". Ciccle knows he's there to help Mena secure another Black Bull, and to be there as he's ridiculed, forced into chastity, and then asked to clean her up. Cause, after all, you can't expect a lady to leave a Cuckold Session a sticky, cummy mess! ...Read More
Hope Howell - Cuckold Sessions

Hope Howell - Cuckold Sessions

20th May - Warning: this scene is not for the faint of heart. It stars an evil cuckoldress, Hope Howell, and her pathetic, wimpy, sissy cuckold...whose name isn't even worth mentioning. Prepare yourself to watch as Hope puts him through the ringer. If Hope isn't whipping his ass, she's whipping his disgusting, little pee-pee. If she's not sissifying the Cuckold, Hope's degrading him. And, at random intervals, Hope's 11-inch Bull walks in to have his way. Hope's as submissive to her Bull as the cuckold is to Hope. My favorite part of this scene? Watch as Hope challenges her Cuckold to a cock-sucking challenge, one in which Cuckold will lose, of course. Cuckold will pay for that, too! ...Read More

Janet Mason and Misty Stone - Cuckold Sessions

Janet Mason - Cuckold Sessions

20th May - If you're hip today's lingo, you'll probably know "to catfish" means to lie about yourself during an online, "getting to know you" chat session. One of the biggest reasons to catfish? Dick Size, of course. That's what today's cuckold -- Ciccle -- is guilty of...catfishing Janet Mason and her man on one of those online, swinger websites. You know the "swinger" lifestyle -- married couples looking to "hook up" and have some adult playtime. Ciccle and Misty are brand new to the game, while Janet Mason and Rob Piper are seasoned vets. After a few hours of "getting to know you" time, it's back to the apartment for swinger time. That's when the clothes come off, and Ciccle's "8 inch thick rod" is exposed for what it truly is -- a 5 inch winkie. That's when Janet Mason takes control, teaching Ciccle a lesson for liars and teaching Misty what to do with a worthless, tiny wiener. ...Read More
Cindy Lou - Cuckold Sessions

Cindy Lou - Cuckold Sessions

10th May - Most of the time, it takes an "in" to get your foot into Porn Valley's door. Turns out Trent Daniels is lucky enough to know Moe "The Monster" Johnson. Turns out Trent's also out of work, and he musters up the courage to ask Moe for a favor: any way you can get me a try-out? Trent wants to be a Porn Star. Moe knows a freak named Cindy Lou, and she's always DTF -- down to fuck. Moe decides to swing by Cindy's with Trent in tow to see if he has what it takes. Poor Trent. Turns out his "10 inch python" is a 4 inch cocktail wiener, which means this Porn Valley try-out is, in reality, another white boy's Cuckold Session ...Read More
Holly Heart - Cuckold Sessions

Holly Heart - Cuckold Sessions

5th May - Who wouldn't want to be Holly Heart's cuckold? Just take a long look at her! Those beautiful, long legs. Her incredible ass. Those firm, round tits. And her pure blonde hair! What's it take to land Holly as your wife? Well, a lot of money, to start. If you had the chance to be Holly's man, you'll have to allow her to go out on weekends to be serviced by big, black bulls. If she wants to go to an adult bookstore to see what kind of trouble she can get in to, you better go with. You know she's going to find trouble, and you'll want to watch. When it's all said and done, you'll clean her up, too...because you can't allow your beautiful wife to walk out of that adult bookstore sticky with another man's cum. ...Read More
Amirah Adara - Cuckold Sessions

Amirah Adara - Cuckold Sessions

2nd May - We get a lot of e-mails from cucks all over the world wanting to partake in a session for the site. Recently, we had an issue with a cuck calling himself "Osiris". He's sent many, many e-mails requesting a session with our Number 1 Bull, Shane Diesel. We didn't think he was serious, and we called him out on it. Osiris replied with sending Mr. Diesel a check, which promptly bounced. You'd think such a loser would go away...but not Osiris. He came to our studios with cash in hand to make up for his grievous mistake. Shane responded kindly with a session for Osiris with none other than European Superstar Amirah Adara. You're gonna love this one! ...Read More
Madelyn Monroe - Cuckold Sessions

Madelyn Monroe - Cuckold Sessions

28th April - We live in the future, so to speak, where technology reigns supreme and "virtual experiences" are becoming the norm. I don't care if you're watching a concert or jumping out a plane, you can do it in a virtual setting now. Same goes with cuckolding. Ever wonder what it's like to have your own, virtual cuckold session? Well, grab your male chastity device (preferably a CB 6000), strap down your tiny little pecker, and let Madelyn Monroe guide you through a session with her! Madelyn has absolutely no problem with this: she'll remind you, over and over, what a pathetic loser you are; she'll ask for your debit card and PIN number so she can take her Bull out shopping on your dime afterward; and, finally, when it's time to clean up, Madelyn will make sure you use your tongue to clean Rico's fresh load off her ass. Cause, after all, you're pathetic ...Read More
Mary Jane Mayhem - Cuckold Sessions

Mary Jane Mayhem - Cuckold Sessions

11th April - The definition of a cuckold is simply a man who knows his wife in unfaithful, and he accepts it. He's OK with his gal getting banged out, so, if you're with a porn star, or an escort, guess what? You're a cuckold. Enter Alex. He's been in a years-long relationship with Mary Jane Mayhem, the porn star. He's also Mary Jane's biggest fan. He watches all her movies, and the sight of his woman being pleased by another man makes him jack off like a monkey in the zoo. His all-time favorite scene? Mary Jane's scene for the world-famous Blacks on Blondes, in which Rob Piper stretched her cunt to the max. The only thing better than watching the movie, of course, is to watch it all go down in real life. He knows Isiah, so he presents his beloved girlfriend to the black man in order to satisfy his own perverted needs. Mary Jane's reward? Well, it's two-fold: Isiah's three-day, backed-up load in her tight pussy, then boyfriend gets to spray it down her throat. The ultimate excitement for Mary Jane and Alex? No birth control for Mary Jane! ...Read More