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Cuckold Sessions – Octavia Red – Octavia Red Get Fucked By A Real Man

Octavia Red – Octavia Red Get Fucked By A Real Man
Released: February 7, 2026

Octavia and Tony are meeting with their Lawyer Kris. When they first married Tony was a trust fund dude and Octavia saw this as a way to a much better life. But over time Tony never raised to be good with money and a chronic masturbator/sex fiend blew through all the money except for enough to put his wife through school and now she is the executive and the real power in the relationship now. Being a powerful Woman she wants a Powerful man in bed as well. Now that Tony is totally reliant on Octavia, things have to change.

In the meeting with their attorney Kris, the original Prenuptial agreement will be torn up and Tony offered a choice of a cuckold contract instead or out on the street it is. Being a massive pervert that he is, Tony is turned on by the ideal of being locked in chastity and watching his wife be regularly fucked by Real Men. Once he signs the new contract Octavia will be ready with her strap-on to slam home the meaning of his new place in life much to the laughter and ridicule of Kris. Once done with Tony, huffing and puffing she jumps Kris to his delight and swallows his cock and impales herself onto a Real Man’s Cock to seal the deal of their new life together.

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Cuckold Sessions – Angelina Moon – Angelina Moon Is Ready For a Load

Angelina Moon – Angelina Moon Is Ready For a Load
Released: January 31, 2026

Angelina Moon has had the hots for her Stylist at the Salon for a while but knows that her Dominant lifestyle is not for everyone. So before she even really needs it she makes an appointment to go see him again but this time to bring her cuckold with her and gauge his reaction. Boswell Black is a bit shocked you can say to see this obviously submissive boy following along behind one of his favorite customers, a bit more even when he drops to his knees to worship her feet while he gets started on her hair.

Seeing that she was just in to see him and comments on this, Angelina lets Boswell know that she is here to see him just as well. Angelina makes no pretense from this point on grabbing at his cock and commenting on how it’s just as big as her arm. Boswell, a bit confused asks what is the relationship between her and her cuck Taylor so she makes Taylor stand and display his very tight chastity device to which Boswell has a good laugh and now knows Angelina will be his. Just for her own enjoyment Angelina compares to her arm to Boswell’s huge cock and it is indeed bigger than her arm in places, and just the right size for her Pussy.

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Cuckold Sessions – Cassie Del Isla – Getting The Job

Cassie Del Isla – Getting The Job
Released: January 24, 2026

Cassie Del Isla has finally been promoted to a position at work to which she deserves, as a partner in the firm and now truly a position of power. Being married to Des Irez, the cute boy from the mailroom, has certainly not helped to pay the bills of the kind of life she likes to lead. So when it comes time to celebrate Cassie recruits a couple of studs (Will Tile and Goldey) from the sales department who really know how to go balls deep in all of her holes. Des loves his sexy and powerful wife and tries to show it the best way he is capable of but flowers are just not going to cut it this time. He comes home just in time to see her hands are fully wrapped around two big throbbing solutions to her needs.

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Cuckold Sessions – Liz Jordan – Liz Jordan Gets Spanked By Her Boss

Liz Jordan – Liz Jordan Gets Spanked By Her Boss
Released: January 10, 2026

Liz Jordan has been working for a very strict boss as of late and finds that she enjoys his discipline so much she is making deliberate errors to get her spanking fix when she needs it. Well it’s one of those days with many errors on purpose that she has assumed the position over her bosses desk when her weak ass boyfriend comes by calling her name to take her to lunch. She calls out that she can’t make it followed by a firm swat to her ass and then another.

Her intrigued boyfriend takes a look through the cracked door and starts to touch himself to the very sexy sight of Liz’s ass red and warm. Her Boss Justice Nice is laying it down when he spots Pony Boy the bitch BF spanking his wiener and decides to give him a show and pulls down her sexy panties as well. Followed by his thick cock into Liz’s sexy mouth. Justice let’s Liz know that her BF is watching and she orders him to lick her getting her ready for a True Man Sized Cock from Justice to use her while the pathetic Pony spanks his terrible two inches and eventually cleans up the Real Man’s Cum.

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Cuckold Sessions – Harley Love – Wants To ‘Model’ In Front Of Her Hubby

Harley Love – Wants To ‘Model’ In Front Of Her Hubby
Released: December 20, 2025

Harley Love and her husband Cole Church have recently moved to the area and she has been looking for a job. She answered an ad for modeling work and the agent Will Tile thinks she has lots of potential. He wants to signs her up for all kinds of work, especially a fans program but he is not sure about her husband and if he will be ok with it. So Harley brings Will to her home telling him privately that Cole has some cuck tendencies and she thinks he will go along with the plan.

When they first talk to Cole he is very supportive of his wife’s plans but when Will tells him exactly what she will be doing his tone changes a bit when he finds out she will be fucking lots of other men. Both Harley and Will want to be sure he will be ok with this by fucking each other in front of him which Cole was very much not prepared to but his strong cucky nature will not allow him to stand up for himself and his own hardening cock gives him away too. Harley is quick to tell her husband Cole that after taking Will’s Giant Cock she will likely never be able to feel his much smaller penis. Will finally seals the deal, shooting his load all over Harley and Harley asks Cole to clean her up with his tongue and kiss her to show his acceptance of the new path for her life.

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Cuckold Sessions – Alexis James – Alexis James Meets Her Goal To Fill Her Holes

Alexis James – Alexis James Meets Her Goal To Fill Her Holes
Released: December 6, 2025

Alexis James has been out all night leaving her cucky boy Tony Orlando at home worried sick about her. She has been getting railed in the bathroom at the club by two hot guys and even in the cab on the way home. But for Alexis that was not enough for a Woman with her goals. After dealing with her whiny cuck for a moment she gets right back to her plan to fill all of her holes at once. She keeps a chaste little cuck at home to be a house bitch and cook and clean for her but Her real needs must be met by men with Giant Cocks.

Ace Hardz and Goldey are just the men for the job and put her through her paces quickly moving on from just fucking her pussy to having her ass opened up and then even more with both cocks inside her at once. This is the moment Alexis has been waiting for and her eyes roll back in her head with joy. Both men bang her with abandon until ready to drop their loads on her face and chest with cucky right there to orally worship and clean up the sticky mess.

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Cuckold Sessions – Olivia Madison – Olivia Madison Gets Her Fix From Plumber Kris Kixxx

Olivia Madison – Olivia Madison Gets Her Fix From Plumber Kris Kixxx
Released: November 29, 2025

Olivia Madison has been nervous about having a plumber come over to fix the sink in one of her bathrooms. Well because it just happens to be attached to her playroom. When she informs the Plumber Kris Kixxx he seems unfazed, that is until he gets a peek inside and then he is full of questions for Olivia and he likes all of the answers. But the best moment comes when her naked cuckold slave Jake Alexis comes asking if he can do anything and Kris can’t help but have a full laugh seeing this tiny manboy naked with a pink cage locked onto his tiny little thing that passes for a cock.

Kris immediately asks him how do you call yourself a man to which both he and Olivia laugh. Seeking his opportunity to be the Man of the house Kris makes his move much to Olivia’s delight. She needs a strong large cocked man in her life with a tiny cucky Jake around. Olivia gobbles up Kris’s enormous cock with vigor before spreading this Goddesses 6 foot 4 legs wide, wide enough for Kris to fuck the daylights out of her and cucky to still worship her feet. Finally Kris fucks her to a mighty pop all over her ass and cucky finally knows he has some worth as a cum lapping little bitch to lick clean her luscious ass to Kris’s combination of recoil and amusement with a very long winded ….Damnnn!

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Cuckold Sessions – Brittany Andrews – Brittany Andrews Penetrates His Ass With Strap-On

Brittany Andrews – Brittany Andrews Penetrates His Ass With Strap-On
Released: November 8, 2025

Brittany Andrews is finally engaged to a very sweet man and she plans to break him completely. Her final test for him before getting married is to see if he can handle her needs for more and more cock than even he can provide for her. She has arranged to bring one of her Studs Will Tile over to service her needs while her Fiancé Pierce Paris, who has been a bit feisty about this plan is safely tied to a chair at least at first. Right on time Will enters and takes charge of the situation helping Brittany to strip out of her stylish MILFY wardrobe and immediately she drops to her knees to worship his enormous Cock.

But Will is quick with the plan and bends Brittany over to be face to face with Pierce so he can see her face contorted in Passion. But after a bit of riding that fat cock she finally let’s Pierce out of his bondage so she can play with is cock and balls as she is fucked on her back and finally loaded up deep inside with Will’s Manly load. With something less than enthusiasm Pierce licks his Fiancé’s cream filled pussy as she taunts him with the rest of her plan to penetrate his ass with her strap on until he too cums, sealing the deal of their future together.

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Cuckold Sessions – Ashley Tee – Birthday Fuck For Ashley Tee

Ashley Tee – Birthday Fuck For Ashley Tee
Released: October 25, 2025

Ashley Tee thought her Husband had again forgotten all about her Birthday and was off on a business trip not to be heard from. This has been going on for a while now and Ashley has been turning her attentions to the studly man from London down the street. For about 6 months now his giant cock has been stretching Ashley’s pussy out wide without her husband Oliver Clothesoff the wiser. Well after inviting Oliver over and wearing her pretty pink party dress for him, well Oliver knows what time it is to sink his fat cock deep into this lonely housewives pussy.

Just as she is trying to crack her jaw open wide on that Huge Cock does her Husband Oliver come in carrying roses and balloons for his wife’s Birthday. Never even taking her hand off the cheating cock she asks her husband what did he expect? For her to wait around for his tiny cock to come home, maybe if he remembered. A bit crushed but aroused at the same time of seeing his wanton wife, lips dripping fresh from her sucking cock. He quickly admits that when he is so often on the road these are the kinds of movies he rents in the hotels. Ashley jumps right back to what she was doing and soon jumps on Mannie Coco’s cock again for her first time ever squirting, inspired by her slutty behavior of course. Ashley uses her husband and sex furniture all while telling him this is the slut he can expect from now on. Oliver’s descent is complete when Mannie sits on Oliver’s back to have his wife suck his cock as well. Mannie’s load is soon all over Ashley’s tits and her husband rushes to kiss and lick her clean followed by kissing his lovely bride.

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Cuckold Sessions – Savanah Storm – Savanah Storm Can’t Resist Her Personal Trainer

Savanah Storm – Savanah Storm Can’t Resist Her Personal Trainer
Released: October 11, 2025

Savanah Storm has been wanting to fuck her personal trainer for some time now and finally decides to bring him home when she thinks her husband is not there. She walks in immediately grabbing his cock and talking oh so dirty to her trainer Will Tile, not knowing that her Husband Silas is just around the corner in shock at her betrayal. Savanah drops to her knees to taste that giant cock slurping away and promising him that her husband is not there.

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Cuckold Sessions – Whitney OC – My Husband Watched Me Fuck With The Masseur Cole Church

Whitney OC – My Husband Watched Me Fuck With The Masseur Cole Church
Released: September 13, 2025

Whitney OC and her husband Cole Church have an appointment with a very naughty massage parlor. Cole heard about this place from some friends of his who were married and they said it really spiced up their sex life. So he called them up and asked for a special sexy massage. Goldey, the masseur on duty, and he is not used to a couple quite so good looking coming in and pulls Cole aside and asks are you sure about this? Cole assures him this is exactly what they want.

Goldey starts off light but teasing the sexy wife, playing her body with years of skill to coax the slut right out of her. But once he flips her over and massages her breasts then drops even lower to lick her pussy with his special technique. Cole has his cock out now watching his beautiful wife Whitney succumb to Goldey’s ministrations. By the time his cock spreads Whitney’s pussy open wider than ever before she is pulling Goldey all the way in with need. Whitney needs cock in so many ways and tries to get it as far inside her with each position. Suddenly Goldey pulls from her heated pussy to jack a fat load onto her stomach only for Cole to jump in and taste it and share it with a kiss with his beautiful wife.

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Cuckold Sessions – Sophia Sterling – Double Dip Treatment For Sophia Sterling

Sophia Sterling – Double Dip Treatment For Sophia Sterling
Released: August 30, 2025

Sophia Sterling and her BF Jake Alexa have what most couples wish for. A loving caring relationship, but what they do not have is sex. Sophia’s boyfriend Jake has a micro penis, a labia nudger, a cockette not worth the two fingers he uses to play with himself. Sophia of course has needs and finally got Little Jake outfitted with a very special chastity device that resembles what he really is to her. See it looks like a pussy and since he is really more of her GF than a BF it is very suited to him. On this special occasion they have decided to have a cuckold date with a couple of Bulls she has been keeping on the side. So out comes little Jake with his pussy shaped chastity on much to Sophia’s delight. Jake is so embarrassed but then he should be even if his cockette was showing. After a quick subby foot rub the Bulls are here and she sends Jakey to answer the door wearing only his device. Goldey and Jaxson Briggs come in laughing with delight at such a ridiculous sight. But with Sophia raring to go they quickly take her body very seriously. For Sophia this is a special night to get all of her holes filled and will not be satisfied until she gets the double dip treatment. Little Jakey is in for the sight of his life seeing his special girl split wide open with real Cock. These guys used her hard until they both dump their huge loads of cum on her for Jakey to dutifully clean up.

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Cuckold Sessions – Bad Bella – Cheating Wife Bad Bella Needs More Cock!

Bad Bella – Cheating Wife Bad Bella Needs More Cock!
Released: August 16, 2025

Bad Bella has been so very Bad lately, She has been hooking up at the Club she works at with the hot DJ named Chocolate God. She is obsessed with his Huge Cock and how it makes her feel. Her Husband Jesse has commented about how her pussy has tasted different as of late but still has no idea that she has been feeding him her Lovers creampies. Finally things got out of control and she stayed out all night with ‘DJ Choc’ and her Husband was staring at his phone all night worried sick about her as she did not respond.

Well her phone had died and she did not notice as she was Choc full of cock and cum. Walking in, Jesse exclaims to her where has she been and there was no hiding this any longer. Choc follows her right in and she whips out his cock to show Jesse why she can’t help but devour this massive meat he has. Even Jesse, who is not small of cock can not deny this thing on his wife’s Lover is Huge. And Bella starts sucking and showing Jesse why she can’t live without this dick. Once Choc has dicked Jesse’s wife down in front of him and dropped another load inside her, Jesse realizes he has come to enjoy the taste of his wife’s pussy Choc full of nut.

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Cuckold Sessions – Hime Marie – Teaching Her Boyfriend Not To Be Jealous

Hime Marie – Teaching Her Boyfriend Not To Be Jealous
Released: July 19, 2025

Hime Marie is determined to break her new boy Bentley Lane of his jealous habits. He has always been a vanilla boy and struggles with his need to please his Mistress and her need for lots of Cocks other than his little wiener. But nothing a little tease and training can not solve. Himes has some serious Bulls, Don Prince and Musa Phoenix, who know just how to help her train her boy to accept his position in her life. She has committed to keeping him pussy free, well that is only used pussy for Bentley.

Hime’s Bulls, Musa and Don get right to work on her as she orders Bentley to strip and drape himself over the bondage rack to watch. Her mouth and pussy are well used by both big studs but when it comes time to stretch her ass out Musa grabs the back of Cuckie’s head and shoves it deep into his Mistresses ass to open it up and lube it for their Huge cocks. Once she mounts Musa huge weapon it slides right into her tongued out hole. From then on Bentley is kept close as the best mouth for lube and eventually cleaning up the loads of cum the studs leave behind.

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Cuckold Sessions – Taylor Rae – Taylor Rae Seals The Deal

Taylor Rae – Taylor Rae Seals The Deal
Released: July 5, 2025

Taylor Rae is so happy to be engaged and ready to seal the deal with her good little BF Buck Richards. She thought today she was going to be going to visit his lawyer to sign the marriage license when in fact she was blindsided by being asked to sign a prenuptial agreement. Outraged, she sits up on the desk and tells the attorney in no way is she going to sign this without some changes to reflect their very specific relationship. She launches into telling the attorney Boswell Black about all of Buck’s twisted fetishes and cuckold needs, especially knowing the attorney client privilege is in play.

How Buck just loves to see her fuck as many guys as she wants, she does this while stroking Boswell’s cock though his slacks. Telling Buck the Cuck to worship her feet she fishes Boswell’s Huge cock out of his pants and begins to slurp on that enormous member. Buck is even more excited to see his darling Fiance have her pussy stretched out as Boswell fucks her deep. Buck knows he can never make her feel that way and just hopes she will slap his cock and balls around like the useless appendages they are. But when Boswell reaches the climax of his involvement and shoots his load all over her bald pussy Buck takes not a moment to dive into her pussy to lap up that other man’s cream as a good cucky sub will do.

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Cuckold Sessions – Jill Taylor & Tiffani Madison – Jill Taylor And Tiffani Madison Show How To Handle Cock

Jill Taylor & Tiffani Madison – Jill Taylor And Tiffani Madison Show How To Handle Cock
Released: June 7, 2025

Jill Taylor and Tiffani Madison met at the local nail salon and have become fast friends and as girls do they talk about their relationships. Jill has confided that her BF is having a lot of cuck fantasies but she doesn’t know how to handle it. Tiffani has advised her that she and her BF Don Sudan, who has an enormous cock, know just how to help her out. So they all meet for a couples dinner and right away Don and Tiffani spot how Dante, Jill’s BF is quite the little house husband setting the table and catering to all.

Jill is just adorable in her very Trad Wife outfit and soon she is sitting on Don’s knee wiggling her ample ass onto his Huge Cock. As Dante notices how flirty and very friendly this new couple is he gets more and more flustered. When he comes back in the room with Don’s cock deep into Jill’s mouth he gasps with shock. But Jill reminds him she knows this is his fantasy and he should just relax and take a seat in the corner. But when the girls start taking Don’s Huge Cock in their asses Dante asks Jill that he thought she didn’t want that. Of course her reply is something he will get used to hearing. ‘Honey Just not With you.’ But when it comes time for Don’s creamy mess to be cleaned off of Jill , Dante is informed he is now gone Full Cuckold.

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Cuckold Sessions – Laura Bentley – Tutoring Assistance With Goddess Laura Bentley

Laura Bentley – Tutoring Assistance With Goddess Laura Bentley
Released: May 24, 2025

Laura Bentley is a lonely professor at the local College who has taken a Fancy to a sweet and obedient boy named Sage Roux who loves to worship this blonde Goddess in every oral way she will Tile allow him. It’s during just one of these trysts with Laura and Sage that Coach Will Tile and his star player Neptune come seeking her tutoring assistance walk in on Laura with Sage caressing her stockinged legs and his tongue all the way up her pert little ass.

Coach and Neptune see the look of lust in the teacher’s eyes and she looks at Sage telling him isn’t this just the fantasy that we discussed. Sage nods his head with his mouth still dripping from Laura’s dew. Being the natural Coach that he is, Will Tile takes charge and takes Laura’s panties off and places them on Sage’s head and shoves him out of the way to drip his substantial cock inside Laura’s tight pussy. Laura’s eyes quickly glaze over as she is fucked silly several ways and finally her tight little ass is stretched out as well. But this teacher who by now is deep into her own desires demands that both of her holes be fucked at the same time for the very first time in her life. Will and Neptune are more than happy to take and stretch and fuck her wider than she ever has been. Sage, ever the obedient boy on standby, is there to lick up the men’s salty loads and make out with his Goddess, sealing his submission to her.

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Cuckold Sessions – Natalie Brooks – Two Huge Cocks Fucking Slutty Natalie Brooks

Natalie Brooks – Two Huge Cocks Fucking Slutty Natalie Brooks
Released: May 10, 2025

Natalie Brooks has been seeing a new boy for a little over a year now, she could sense his need to please and how he enjoyed her being assertive, which she loved. By the first date he was worshiping her feet and the second she had her strapon in his ass just as she planned. But today is different as she wants to up the game a lot, so as Pony Boy kneels before her putting on her stockings and heels she tells him about the two huge cocks that are coming over to fuck her.

But she doesn’t want him to be left out so she takes him into the playroom to drill his ass first. When her studs arrive, Boswell Black & Goldey, they are a bit thrown aback not sure they want to get down this way but she assures them that her didk is only for her sub. Dripping with eagerness she drops to her knees to suck their cocks and they quickly take over from there drilling her pussy out with passion. Pony Boy has a hard on and stroking away watching his hot Girlfriend completely used by them. But then he knows how it feels with his ass still burning from the pounding he took moments ago. As her studs start to drop their loads on her she gets even more excited waiting for her good little subbies tongue that will lick her completely clean after.

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