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

Latest Updates from Cuckold Sessions (Page 2)

Natasha Nice - Cuckold Sessions

Natasha Nice - Cuckold Sessions

28th May - Natasha Nice is a Supreme Cuckoldress, and today's Cuckold Session shows off her awesome skills. Just look at the way she handles not one -- but two -- sissy bois. The first round of mental fuckery begins when the cucks think they're going to fuck a girl...which, they are. Once they blow her up! Natasha has her sissies take turns face fucking and fingering the blow up doll before it's warm-up time. Natasha is such a giving Cuckoldress! Round two includes sweet Natasha allowing her sissies to warm up both holes with their tongues, even though it bores her to tears! Thank goodness that's when The Bulls arrive. Time for Round Three: make no mistake about it, if either sissy looks at either Bull in any sort of "faggy fashion", it'll be time for a beat down! Natasha has already given her Bulls a green light to kick white-boi ass, and they both make it abundantly clear that's exactly what they'll do! Round four? All of Natasha's holes are pounded while the cucks helplessly jerk. Which, of course, leads to the final round and a grand finale: clean up time! Lucky Natasha has two cucks to clean her up, which she'll need, as both Bulls walked into the room with days of backed-up balls! Don't miss a drop, cuckie boi...or you might get that beat down after all!!! ...Read More
Alana Cruise - Cuckold Sessions

Alana Cruise - Cuckold Sessions

14th May - Alana Cruise has a controversial relationship with her step-son, Codey. If you've been to Cuckold Session's sister site, Watching My Mom Go Black, you already know all about Alana and Codey. Today things just get more..."controversial". Codey's on a hunt for BBC to satisfy Alana after a long day at work. Codey is striking out. No luck. This disappoints Alana, so she ups the ante: "find me two black bulls, and I'll suck your dick! I'll be upstairs in my room, putting on some sexy lingerie!" Codey can't believe his ears! What incentive! He's speed dialing every black guy he's ever known!! He strikes gold, too! Soon, we have step-mom sucking step-son before two hung bulls come to fuck all Alana's holes! After it's all said and done, Alana's got jizz all over her face -- from Bull 1, Bull 2...and, as a reward for work well done, her step-son's!! ...Read More
Nina Elle and Angel Smalls - Cuckold Sessions

Nina Elle - Cuckold Sessions

30th April - Indoctrination. You're about to witness it, first hand. Nine Elle and her hubby are in the middle of a cuckold session when their barely-legal daughter, Angel, came home early from a date. Angel is home early because she was sick and tired of watching her boyfriend check out all the other girls at the beach! Needless to say, Angel was shocked when she walked into the house to find her dad masturbating as he watched a black man fucking her mom!! The only thing she could do was shriek! Watch mom and dad rush to their daughter to "explain". Explanation? Indoctrination! Soon little Angel is on her knees with mom, sucking black dick, while dad enjoys the show! Warning: you're about to witness a new level of cuckolding...one so taboo it may leave you feeling disturbed -- or hungry for more! ...Read More

Chloe Couture - Cuckold Sessions

Chloe Couture - Cuckold Sessions

16th April - Chloe Couture is the biggest slut ever. Just ask her boyfriend. He likes to brag about Chloe and her slutty ways to all his friends. Just listen to him shooting hoops and blabbing about all the naughty things his girl will do! Which is just about the time Chloe comes out to do a little sunbathing. She'll go topless, too, and not care what her boyfriend -- or his buddies -- think. Chloe's boyfriend brags 'she'll do anything I say! Just watch!!' Soon, Chloe's on her knees in the backyard, sucking big, black cock...because her boyfriend told her to! Then, he'll command Chloe to offer up her sweet, pink cunt before moving to her back door. That's right, Chloe's boyfriend offers up her ripe, tight asshole to his buddies! They'll take it, of course, before all three dropping loads on Chloe's face -- or down her thirsty throat. Some call this very naughty...others call it true love. ...Read More
Gina Valentina - Cuckold Sessions

Gina Valentina - Cuckold Sessions

11th March - Gina Valentina has a Cuckold Sugar Daddy! It's the best of both worlds! BBC and money! Gina loves turning Sugar Daddy Cuckold into a Pay Piggie, and she drains his wallet all the time: shopping, nights out with the girls, bills, and taking her Bulls out to shop and have nice dinners as well! She even uses his place to fuck her Bulls, which, of course, Sugar Daddy Cuckold knows. That's why he "came home early", right in the middle of Gina's fuck session. What's that mean? A fuck session turns into a Cuckold Session! Of course Sugar Daddy Cuckold is gonna pay, cause no way is the Bull going to allow anyone to watch unless he gets paid. Gina's gonna get paid, too, right after she gets laid. Wow, does the Bull's thick, 11 inches stretch Gina out! Her pussy will never be the same after he's done...and when he is done, The Bull is going to spray Gina's ass down with a thick, hot load. Hey, Cuckold Sugar Daddy! It's time to clean your Sugar Baby up so she can take Flash out to dinner...using your credit card, of course! ...Read More
Lauren Phillips - Cuckold Sessions

Lauren Phillips - Cuckold Sessions

6th March - Our session opens today with Cuckoldress Lauren Phillips in a frantic mood. She's frantic because her Bulls are on their way over, and she likes being fucked on clean furniture. Her slave, Fluffy, isn't doing a satisfactory job. All he has to do is clean the damn furniture to her liking...and the worthless loser can't even do that correctly. Fluffy has his chastity device strapped on, and it's electrified! That's right...with the simple turn of the dial, Goddess Lauren can send a wave of electricity straight to his tiny ball sac! She'll utilize this, of course, before her Bulls arrive...and once they're there, Fluffy will be sent to his cage. He can watch, but they will be no jerking off for Fluffy today! Lauren's Bulls ravage her, too, taking all three of her holes whenever they please. The only time Fluffy is released from his cage is to secure Lauren on her fuck sofa as the Bulls take her ass and cunt at the same time. Oh yea...Fluffy will also clean the mess Lauren's Bulls leave, too! Fluffy's reward for a job well done? More electricity to his puny dick and balls!! ...Read More
Stella Cox - Cuckold Sessions

Stella Cox - Cuckold Sessions

6th March - Dirty talk. We all do it. We all love it. Stella Cox and her Hubby have a few fetishes they love to talk about as they fuck: Stella cheating; Stella with a well-endowed black man; Stella fucking the well-endowed black man while Hubby watches her. Guess what? It's their anniversary! Three years of marital bliss, with lots of sex and dirty talk. Hubby is treating Stella to an expensive dinner to celebrate. Stella has a few gifts to give, as well! The first? She's going to change into some of Hubby's very favorite lingerie and give him a lap dance. She'll tease and grind before bringing out The Big Gift: her well-endowed, black lover! Watch how Hubby reacts as fantasy quickly turns to reality!! Stella offers all three holes to her lover, even cleaning off his enormous black cock after pulling it out of her ass! The Bull drops his lads and leaves, which means "private time" starts with Stella and Hubby! ...Read More
Britney Amber - Cuckold Sessions

Britney Amber - Cuckold Sessions

26th January - You're about to witness the happiest couple in the whole world...and what makes them so happy? Britney's a cheater, and even though she craves BBC, she feels kinda bad lying to Hubby. Hubby, on the other hand, know's Britney's a cheater. It gives him a huge thrill to know Britney's unfaithful, and he's waiting for the right time to not only break the news to Britney that he knows she's a cheater...but to tell her it's OK. Hubby loves that he cheats, and all he'd like is to watch from time to time. Well, today's the day. The "work crew" is by to "fix something" when Hubby shows up early from work, so it's on! Hubby crashes the party, which freaks everyone out...until he let's everyone know it's OK. He instructs the Bulls to finish the job they started, right after he reassures Britney he's not mad at all. Britney's relieved to hear Hubby is a cuck, and she proceeds to give him the show of a lifetime. One of many to come. Like we said...the Happiest Couple in the World. ...Read More
Olivia Austin - Cuckold Sessions

Olivia Austin - Cuckold Sessions

26th January - Olivia Austin is a true Cuckoldress. Just look at her! She marches in from a day using her man's credit card to fulfill her desires, only to discover he's brought up a bottle of the wine she doesn't like! Can't he do anything right?! Of course he can, starting with a foot massage. Walking long hours in the mall with slutty heels can take their toll on any gal, and Cuckboi sure does a great job making them feel better! So much so, she's going to tag "CUCKBOI" across his chest right before Cuckboi does what he does best: locate Bulls for his lovely wife. Two are on the way, and when they arrive, Cuckboi is at the door to show them into his bedroom. It is on their marital bed in which both Bulls have their way with Olivia, fucking her all the ways Cuckboi can't. Don't believe it? Look at the mess both leave on beautiful Olivia! Who's going to clean it all? Do we really need to answer that? ...Read More

Katie Morgan - Cuckold Sessions

Katie Morgan - Cuckold Sessions

22nd January - What happens when you're a bored, freaky couple? Call in the black guy, of course! Just take a look at Katie Morgan and her hubby, Alec. They've been together for years, and as you probably know, years of monogamy will lead to boredom. Their handyman, Jax, is in the backyard working, and since he's pretty much done with the job, how about giving him some more work...in the form of Katie's beautiful, blonde cunt?!? Jax happily agrees, and soon he's on his knees tonguing her beautiful hole while Hubby starts jerking with excitement! Hubby gets more excited as Jax bangs Katie to multiple orgams, cumulating with a splattering of Jax's jizz all over his beautiful wife? What then? Hubby's turn! ...Read More
Kenzie Taylor - Cuckold Sessions

Kenzie Taylor - Cuckold Sessions

8th January - Mistress Kenzie Taylor is about to conduct a Cuckold Session, and you're going to witness the whole thing go down! Mistress Kenzie is a firm disciplinarian, and she's not shy when it comes to putting a white boy in his place. Her tongue is razor-sharp, and she's got no problem letting her white boy know just how pathetic he is, or how small his dinky is...all while allowing him the privilege of worshipping her feet. Which is when Mistress Kenzie's Black Bull arrives. He's a real Bull, too; tall, athletic, and packing 11" of man meat, Kenzie's Bull is no joke. He's going to rail the beautiful mistress while all her pathetic cuckold can do is watch -- when he isn't blindfolded. In the end, the cuckold's face is smeared in Bull jizz, and it doesn't really end there! Kenzie has the cuck's debit card, his PIN and her Bull, who she'll take shopping. Cuckold's treat!! ...Read More
Amara Romani - Cuckold Sessions

Amara Romani - Cuckold Sessions

25th December - Amara Romani is dating a degenerate gambler. You've probably known one in your life. All they seem to truly care about are things like the "over/under", the "money line"...the favorites and the "dogs". And how to profit off it all. Amara's man just had a terrible weekend, and he owes The Man "five dimes". Amara doesn't know what that means, but she knows what five thousand dollars means, and she knows her man doesn't have it. The guys coming to collect know it to, and instead of getting a beat down, Amara's man has offered up Amara's awesome blowjob skills, her tight, pink cunt, and her her tiny little butthole as a way to buy some more time. They're going to take him up on the offer, and why not fuck Amara right in front of her man? Remember, he's a degenerate, so he'll sit and watch and jerk his dinky as the two have their way with his woman. After they're done, he'll drop a load on Amara, just for being the best girlfriend ever! ...Read More
Dahlia Sky - Cuckold Sessions

Dahlia Sky - Cuckold Sessions

11th December - Dahlia Sky has a slave, and his name is Fluffy. Today, Fluffy's been a good slave, spending 8 hours (locked down in a chastity belt, no less) cleaning and scrubbing Dahlia's home...until it's spotless. Good slaves earn rewards, and today Fluffy earned a big one: a Cuckold Session. Dahlia leads Fluffy into her bedroom, where her Bull is patiently waiting. Soon, Dahlia's servicing her Bull orally while keeping Fluffy's tiny dick and baby balls locked up. She does allow Fluffy to remove her beautiful heels...and even sniff her feet! What a treat!! What happens to Fluffy when he tries to sniff his Mistress's ass? Or eyes the Bull's enormous black cock? Exactly what any disobedient slave gets! Dahlia spends ample time with her Bull, getting penetrated in all three holes, while Fluffy looks on, unable to jerk his little dinky. However, since he did such a good job cleaning Dahlia's home, he'll have no problem cleaning the jizz off Dahlia's fine ass! ...Read More
Jennifer White - Cuckold Sessions

Jennifer White - Cuckold Sessions

27th November - Nicky's a lucky dude. Just ask Isiah Maxwell. They're buddies, and Nicky's just got done telling Isiah a crazy story about his wife, Jennifer White. They're were out clubbing the night before, and the next thing you know, Jennifer's flirting on the dancefloor, grabbing and grinding on dick. Soon, she's in the parking lot, sucking off strangers as Hubby watches with approval. Isiah can't believe his ears, but he'll be a believer soon enough. He meets Jennifer in the kitchen, and within minutes she's dressed in lingerie and on her knees in the front room. Nicky watches it all go down, from Jennifer's superb oral skills to Isiah stretching out both her holes. She even cleans Isiah's dick right after it comes out of her tight, tight ass! Isiah then fills her white cunt full of his cream, and that's when Hubby rewards his proud wife! What a relationship!! ...Read More
Ashley Adams - Cuckold Sessions

Ashley Adams - Cuckold Sessions

8th October - Poor Nate! You remember what happened to him a few weeks ago over at our sister site, Watching My Mom Go Black? If not, his girlfriend broke up with him, and he was distraught. It was then his mom, Cherie, and his sissy, Liza, who showed him the "way it really is" out there. White men take care of their women...and black men fuck them. You'd think Nate would have listened! Because when he walked into the bathroom at his college and caught his new girlfriend, Ashley, fucking the start running back, well...he started a fight. And the football player ended it. Then, they all got busted! Enter the college administrator, Dr. Christensen. He's got a PhD and well respected, and he wants to see how it all went down. Literally. Of course Nate could get in big trouble for assault and battery...or, he could learn another lesson. A lesson Ashley and the Running Back will teach him. And, in the end, Ashley's going to allow Dr. Christensen to release his stress as well...cause, after all, if she gets in trouble again, the good doctor will have her back! ...Read More