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

Latest Updates from Cuckold Sessions (Page 4)

Nikki Benz - Cuckold Sessions

Nikki Benz - Cuckold Sessions

25th February - Don't ever let your wife talk you into "dance lessons". Why? There's always a handsome, toned-up (and horny) dance instructor, and he's waiting to bang your better half. Unless you're a cuckold. If you are, then you know what dance lessons mean. Take Nikki Benz and her man, for example. She's freaky, and he's even freakier. So when the lessons turn into sex, then time for Hubby to pull his dick out and stroke while Wifey gets her holes stretched wide open. Today gets interesting, because not only is the Dance Teacher pounding his wife, so is his business partner. They're both big and black and all holes are open, so don't be surprised if Wifey gets a big cum load dumped deep into her tight ass. Then, watch as the second bull paints his wife's tits with his enormous load! Hubby knows to cherish Nikki Benz...and their special relationship! ...Read More
Cherie Deville - Cuckold Sessions

Cherie Deville - Cuckold Sessions

29th January - Cherie DeVille is a world-class cuckoldress. While Hubby is out of town on business, not only does she have her personal cuckold over to play...but her well-endowed Bull decided to swing by for a piece of Cherie Pie. First, watch Mrs. DeVille run her whiteboi cuckold through the wringer: his chastity belt is secured, and in addition to the humiliation, he'll get some much-needed cock sucking coaching from Cherie. Then, it's on to her Bull. He's almost a foot long, and sure enough, he's uncut. After pounding Cherie to orgasm, he drops a 3-day back-up into (and all over) Cherie's ripe cunt. I think you know what's next....clean up time, Cuckboi!!! ...Read More
Keisha Grey - Cuckold Sessions

Keisha Grey - Cuckold Sessions

21st January - No matter how hot your girl is, sooner or later things get stale in the bedroom. Take Max, for example. He's got a great house and a beautiful girl and he's bored to tears. After all, how long can someone be expected to fuck in the missionary position with the lights off before it grows old? Max has had this talk with his girl, Keisha Grey about this, and now he's gonna get serious. He just got home with his bro, Isiah, and Max puts it bluntly: "fuck my girl! I want to watch!" Since Max is down, Isiah is down...the only issue? Keisha isn't. All it takes is a little "talking to" and before you know it, Isiah is balls deeps in all three of Keisha's holes, which is a surprise for Max, cause he's never had the chance to bang that sweet ass! Some say it's better to leave fantasies as fantasies...but not here. We make fantasies real! ...Read More

Jada Stevens - Cuckold Sessions

Jada Stevens - Cuckold Sessions

13th January - Degenerate gambler Jesse owns a bar, and he's about to get shaken down for the money he owes The Man. His girlfriend Jada is his barkeep, so she gets to deal with the Hired Guns -- Sean Michaels and his understudy Isiah Maxwell -- when they first walk into Jesse's joint. They're here for the 30 Large, and they're going to do whatever it takes to get it. Jesse's about to get fucked up in a bad way when Jada comes to his rescue. At Jesse's request, Jada will offer up her mouth and white pussy to the boys before she swallows both of their over sized loads. But don't think that's going to get Jesse off the hook...you know they'll be back, and you know they'll get another taste of Jada Stevens...which doesn't bother her one bit! ...Read More
Aaliyah Love - Cuckold Sessions

Aaliyah Love - Cuckold Sessions

4th January - Like most women who are married to wealthy men, Aaliyah Love has a "personal trainer". You know...these are the guys who put their client-wives through a "workout" and make them sweat. Aaliyah's "PT", Isiah, sure does make her sweat. Too bad they've never once used her in-home gym for its intended purpose! All they use it for is another room in the house to fuck. Isiah puts all his MILF "clients" through the same, sweaty routine: drop to the knees to suck, then bend over to get stretched out. This time things are a bit different. Hubby comes home early! At first, he tried to put Aaliyah in her place; however, it's Aaliyah who is the "A Dog" in this relationship, and before you know, Hubby's getting indoctrinated into the cuckold lifestyle. It's a lifestyle he must accept, or it's time for Divorce Court, where he'll lose a hot wife...and half his net worth. ...Read More
Krissy Lynn - Cuckold Sessions

Krissy Lynn - Cuckold Sessions

14th December - You've suspected your wife's been cheating on you for a long time, but you just need to catch her, red-handed. Or, in this case, black-handed...black hands all over her, and today you're about to witness what you've suspected all along as it goes down. Starts with the black dude leaving your house. A stranger to you for sure...but there to fix the modem? So you sneak up to the window, and sure enough...two more black dudes just got there, and it's going down in your kitchen. In the sitting room. In the family room. In your house! Not some cheap motel...the house you pay the mortgage on! Add to this the fact you're conflicted! You do nothing to stop it. In fact, you watch. You watch as men with much larger penises violate your wife in ways she'd never allow you to do...and you're ok with it. You're even ok with the lies when you do confront her, as well as the denial. Let's face it. you're a cuckold. ...Read More
Alexa Grace - Cuckold Sessions

Alexa Grace - Cuckold Sessions

26th November - It's always interesting to watch the initiation process, especially when it's an initiation into the cuckold lifestyle. Meet Alexa and Rex. They're about to get married, and poor Rex has no idea what he's about to get himself into. Alexa has chosen to break the news to Rex as they're meeting with the wedding photographer. Rex is confused, too: why would Alexa choose the most expensive photographer in town? This is going to end up costing thousands more than it should...but Alexis has her reason. The photographer is one of many Bulls Alexa entertains, and today she's going to give her fiance an ultimatum: either embrace the cuckold lifestyle...or find another bride! ...Read More
Nina Elle - Cuckold Sessions

Nina Elle - Cuckold Sessions

16th November - There's something incredibly hot when another man is banging her out in front of your very eyes. Especially when that man is a black man with a dong twice as big as yours. It's so hot, in fact, some couples go to extreme measures to make it happen. Take Nina and her hubby Anthony. They're an open-minded pair who love this sort of activity, and they love to "set up" the Bull. For example, they'll call for a repair man to come fix a broken water line in the master bath...but there's no broken water line. There is, however, one hot and horny wife sitting in a tub ready to seduce the Bull. And Hubby isn't far behind, ready to watch it all go down as well as reward Nina for a job well done. Swallow it all, honey! ...Read More
Anikka Albrite - Cuckold Sessions

Anikka Albrite - Cuckold Sessions

2nd November - Let's face it, you've been on the road too much lately, but your work demands it. You know your wife, Anikka, has been a little dissatisfied lately...but you haven't had much time to even think much about it. And the times you do manage to pay attention to her while you're home, well...the sex is getting a little mundane. What you didn't expect is Anikka's next move. Let's call is "Anikka's Surprise". While you're far away on another business trip making money for your family, your wife took the family camcorder and placed it on a tripod. Then, she pressed record. What starts out as a teaser video for you as a gift when you return quickly turns into something you're not sure you can handle...but you watch anyway. Anikka's invited a black man into your bedroom, and she's going to fuck him on your marital bed. She'll even do things with him she'd never do with you. For example, she takes him in her ass then swallows his cum. After it's all said and done, your head is spinning. Time for a divorce? Or have her invite more men in next time you leave town? ...Read More

Anna Bell Peaks - Cuckold Sessions

Anna Bell Peaks - Cuckold Sessions

27th October - Shane and Ana Bell have come to an agreement. It's time to tell Ana Bell's Hubby (who also happens to be friends with Shane) that they're fuck buddies. They're not sure how Hubby is going to take it. Will he be pissed? Will there be a fist fight? Will he file for divorce? They've decided to do the right thing and tell Hubby right to his face, but first they're going to fuck. Indeed, it would have been the right thing to do...if Hubby didn't come home from work a couple hours early. Ana Bell is freaked out until Hubby makes his confession: he's had a gut feeling they've been banging. After all, Hubby sees how they behave when they go out as a group: holding hands and flirting and kiss-on-the-mouth goodbyes. It turns Hubby on, and he doesn't want to fight or get a divorce; he just wants to watch them get it own while he jerks his little white dinky. Ana Bell's reply? "Oh honey, I love you!" ...Read More
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