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

Latest Updates from Cuckold Sessions (Page 5)

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
Ava Dalush - Cuckold Sessions

Ava Dalush - Cuckold Sessions

1st April - With keeping it real in mind we spoke to Ava Dalush and her boyfriend for this latest update. Ava's guy is completely and 100% cool with his girl fucking and sucking on camera. In fact, the icing on the cake is when she does interracial shoots like the one she did for BlacksOnBlondes.com. The English couple live life on the edge with his voyeuristic ways and her slutty manner. You can see the twinkle in her man's eye as she begins to get down and dirty with resident woodsman Rico Strong. Ava's mouth wraps around Rico's big black cock while her man's grin gets wider and wider. Ava's blowjob soon enough turns into a fuckjob via the black monster Rico carries around on a daily basis. What's the cuckold/boyfriend/future husband doing? He's enjoying every minute of taking in the sights and sounds of his little woman getting the Dogfart treatment. Ava's pussy is rendered useless for the cuckold after Rico's done destroying it. And there's not much left to do except for Ava to welcome Rico's sauce--much to the delight of her guy. ...Read More
Chloe Chaos - Cuckold Sessions

Chloe Chaos - Cuckold Sessions

19th March - We recently invaded Las Vegas for the annual AVN show. We were shooting a chance encounter with Chloe Chaos and Shane Diesel when a fan/attendee broke past security and exclaimed his excitement over encountering the two performers. The cuckold's excitement spills over when he agrees to watch Shane plow into Chloe's cervix. The cuckold gets roughed up right before his eyes fixate on Shane's big,black cock doing some damage. You can bet there are numerous guys in sin city willing to trade places with the cuckold....and he knows he's fortunate to witness an actual Dogfart shoot--let alone participate in one. Shane continues the assault on Chloe'scunt ,right before the cuckold gets his dessert ...Read More
Valerie White - Cuckold Sessions

Valerie White - Cuckold Sessions

6th March - Valerie White's introduction to the world of cuckolding comes in the form of her boyfriend. Jimmy loves the fact this his woman fucks other men; scratch that, it's BLACK MEN that he wants to watch her fuck for his own sick amusement. Jimmy and Valerie make their way to Dr. Johnson for a last-ditch effort to save their relationship. Valerie succumbs to her man's wishes by taking her sexual frustration on Dr. Johnson. the cuckold, as if it needs mentioning, is completely overjoyed at the fact that his girlfriend has honored his request of fucking black cock in front of him. Dr. Johnson risks his license by fucking the eager white slut in his office--and he doesn't seem to give one fuck about it. Actually, the only fucking going on is Valerie's white pussy taking the good doc's big black cock. Jimmy's grin is now as wide as his woman's pussy, since Dr. Johnsons's massive black dick is doing some damage. The chastity belt now on Jimmy is preventing that tiny dick from getting hard. However, it seems not to matter when that black cock makes a mess out of Valerie....and guess what happens next. ...Read More
Ash Hollywood - Cuckold Sessions

Ash Hollywood - Cuckold Sessions

20th February - Ash Hollywood has a problem--you! The sexy blonde knows that it's your wish and pleasure to watch her get fucked by a real man,i.e. someone black and NOT YOU. Rob Piper is just the man to show you how a white slut needs and must get fucked. So, sit back, relax, and watch the black man do something far superior than what you can ever do. Ash's verbal humiliation of yourself knows no bounds. And Rob Piper is there to add insult to injury. The deviant blonde sucks down Rob's rob as she continues to hurl insults in your direction. Can't stand it? Wanna tap out? Well, Ash Hollywood isn't stopping until she feels that big, black cock ravage her white pussy. The furniture nearly collapses (like your soul) while Rob pounds that sweet, white pussy , and, of course, you could never measure up to the mayhem that you're watching. Ash can't take it anymore and has Rob unleash her spunk right on that pussy....and gets who's on clean-up duty ...Read More