UPDATED Wendy Raine Mega Collection
38 Videos | 50 GB
Wendy Raine (born 1972) is a pornstar from Virginia, United States. She is 5'5", weighs 140 lbs and her measurements are 38DD-28-36. She started her porn career in 2022.
Wendy Raine - Forget About the Rent, You Can Be My Pussy Tenant
Released: March 28, 2026
Hoping to earn a little extra cash, Wendy puts up an ad to rent a room in her house. What she doesn’t expect is that Arin, a young and handsome student new in town, will quickly become her obsession. With him staying for a week while he’s taking a course, she will do whatever she has at hand to have him inside of her. To succeed in her kinky plan, she plays an unapologetic seduction game, making sure Arin knows how much she wants to savor his cock. Slowly yet effectively, Wendy eventually achieves her goal and gets a pussy-pounding of a lifetime while Arin takes an “extra course” on how to please a real milf.
Wendy Raine - Don’t Tell Wedny’s Husband — Cheating Wife vs. BBC!
Released: January 27, 2026
I adore my husband, and I would do anything to protect him. He was about to take on the biggest fight of his career. My husband versus the heavyweight champ, Will Tile. I knew this fight was dangerous. His competitor was huge. My husband would never beat this big, black, handsome, muscular boxer, so I made a deal. I asked him not to be hard on my husband, but instead, he could be as rough as he wanted with me. He could put his hands around me and shove his big black cock inside me anywhere he wanted: the table, the couch, the floor, nothing was off limits. As long as he honored our deal, I would obey him.
Wendy Raine & Yaya Gingersnatch - cum comp 09-27-25
Released: September 27, 2025
In our newest Cum Compilation at Gloryhole Secrets, we have Wendy Raine and Yaya Gingersnatch, who love to swallow loads of cum. Wendy Raine is a sexy MILF who loves giving blowjobs with her huge tits out, and she enjoyed nine loads of cum with us. Wendy Raine loves a good titty-fucking too, and took her fourth load all over her beautiful tits. Yaya Gingersnatch loves a bunch of sexy cocks, and her visit gave us 11 loads of cum she enjoyed. As well as swallowing her loads, Yaya Gingersnatch took her tenth load all over her tits and body. She loves a huge load of cum, and her POV scene showed her cum swallowing dreams given to her. Enjoy Wendy Raine and Yaya Gingersnatch today in our latest Cum Compilation only at Gloryhole Secrets.
Wendy Raine - “I Can’t Believe We Spit-Roasted Nana!” Grandparents’ Day Gets Weird
Released: September 7, 2025
I knew my step-grandparents were excited to have me spend the weekend with them for Grandparents' Day, but I didn't know how much. I realized what I'd gotten myself into until my step-grandma started stripping for me while my step-grandpa was talking to me! Sure, he didn't notice, and her body was smoking hot, but I didn't know if that was better or worse. She went underneath the table and sucked my cock dry like a pro! I guess she learned a thing or two in all her years of experience, and I could feel it in every inch of my body.
Sofie Marie - As Seating
Sofie Marie - Elegant Blowjob
Sofie Marie & Stacy Strings - Sofie Meets Stacy Strings
Sofie Marie, Alaina Taylor & Wendy Raine - Famous Orgies 5 With Alaina Taylor And Wendy Raine
Released: August 1, 2025
Harley Love, Jessica Aaren & Wendy Raine - I'm Still in My Stepdaughter's Body, Fuck Us Again (Freakier Friday Parody)
Released: August 3, 2025
No, no, no! This can't be happening. When I woke up today, my body felt weird, so I touched myself, trying to figure out why that might be. My tits were massive! Don't get me wrong, my boobs are beautiful and perky too, but these were not mine. Then, I grabbed my ass, and it was bigger too. Even fingering my pussy felt different. When I looked at myself in the mirror, I understood what was going on: I was in my step-grandma's body! I ran to find her, and she was also trapped in a different body: my stepmom's, which meant... that my stepmom was in my body. Looking at myself in front of me was one of the weirdest things I've ever experienced, and also one of the hottest. All I could think of was whether it was possible to have sex with myself. Everything got even more complicated when my stepmom's old fling came to pick her up for a date. We all tried to pretend to be each other so the guy wouldn't freak out, but eventually, our little secret slipped out. Nobody knew who he was supposed to sleep with, so we made a new deal. Until we got back to our bodies, he had to fuck all of us. After all, if we wanted to go back to normal, we had to walk in each other's paths, and what better way to get to know each other than through a foursome? I'm so glad we did that because nothing has ever felt as good as licking my own pussy.
Wendy Raine, Sophia Sterling & Selina Imai - We Just Want to Make You Feel Better" - My Best Friend's Parents Woke Me Up to Fuck
Released: July 17, 2025
I knew my best friend's family was a little bit weird, but I didn't know how much until they invited me to go on vacation with them. At first, everything was fine, but then her dad made a toast at dinner, thanking his wife and daughter for everything. But when he got to me, he said in front of everyone that it's impressive how much I've blossomed and that he would fuck me if he were 18. Everyone laughed, but I kept thinking about that joke for the rest of the day. My best friend said that I was overreacting, so I apologized and tried to let it go by going to sleep. Then, late at night, my friend was nowhere to be seen, but both of her parents were next to me on the bed. The wife started caressing my hair so slowly and intensely that I got turned on. They said I was having a bad dream and just wanted to make me feel better. I didn't know what to think, but as the wife touched my lips and her husband moved his hands all the way up my thighs, I just wanted them to make me theirs. They said they wanted to show me how special I was to them as they took off my panties, so I let them. Based on the way the dad went down on me, I could tell he's been dying to eat my pussy. Then, he just asked, "Are you ready for me?" Yes, I was. I've never been more ready for anything.
DD White & Wendy Raine - "Do Your Step-Grandma Just Like You Did Me" - Gilfs Don't Want to Clean, They Want to Fuck
Released: July 13, 2025
When I went to my step-grandma's place to help her with her spring cleaning, I had no idea what I was walking into. Her friend came to the house, and I knew right away that she was there to check me out. She looked at me as if I were a piece of meat she couldn't wait to devour and didn't hesitate to show me her massive tits! I'm not going to lie, she was looking really hot wearing a tight summer dress, but she looked even hotter when she raised it so I could lick her pussy while my step-grandma was in the other room. When she entered the kitchen, I hid behind the counter, thinking we should stop or we would get caught, but her friend made me keep going.
Wendy Raine - Mommy Swap 4 - Swapping Horny MILFS
Released: July 11, 2025
It's a hot MILF swap! Playtime was horny moms are about to be explosive! Nasty play becomes wilder than ever!
Wendy Raine - Justice is Best Served Hot
Released: July 11, 2025
Wendy, a sexy lady in a uniform, is the new police officer in town, and for once, justice will be served her way. She just got a call about a serial masturbator, a guy that’s been jerking off in front of his open window and the neighbors have had enough of his indecent exposure. What they don’t know is that the offender is none other than Nick, Wendy’s stepson! Worried about losing her job, she intercepts the call as quickly as possible and barges into her own house to catch her stepson red-handed.
Another mix of selected scenes from OnlyFans, ManyVids or other creator platforms released recently.
Wendy Raine & Eva Nyx - Memories Cumming to My Mind
Released: March 28, 2025
Eva is tying the knot today and despite being happy about it, she can’t help but feel a little anxious. Her stepmom Wendy accompanies her while she prepares for the big event. To add some tension, she is also trying to find out who her biological father is, and the news might break any moment now. Luckily, Quinton, her loving stepfather, arrives in time before walking her down the aisle. Noticing how tense their baby girl is, Wendy and Quinton decide to tell her a story about how they met in the hopes of preparing her to get married.
Sarah Jessie, Fiona Frost, Crystal Clark, Wendy Raine, Amber Summer, Isabel Love, Lizzie Love, Krystal Sparks, Sasha Pearl, Whitney OC, Andi Avalon & Bree Brooks - Milfs Tutor Teens
Released: March 26, 2025
What’s up MYLF lovers? Feeling distracted lately? Do you need a kinky milf teacher who can show you a thing or two about life’s sexiest lessons? Then you’re in luck, ‘cause we’ve got a steaming hot new compilation featuring the nastiest and raunchiest milfs tutoring young naive students. Featuring the likeness of bodacious babes such as Andi Avalon, Crystal Clark, Sasha Pearl, and Whitney OC, these stunning tutors know how to keep their students engaged with their god-given gifts and their frisky pedagogy. Nothing like a good pair of juicy tits to make study sessions worthwhile, or a hands-on sex ed class for students to participate actively. The wild milfs tutors will make you cum while they teach everything that is to know about the kinkiest subjects. So get your pencils and cocks ready for one hell of a study session with the most beautiful teachers!
Wendy Raine - You Cunt Shy Away From Me
Released: February 26, 2025
Jewell was super worried. Her son Rion was so shy; it was like he wasn't even there sometimes! School had started ages ago, and Rion still didn't have any friends. She was heartbroken. Desperate, she talked to a friend who suggested a special professional known for her crazy methods. Known for dragging the most stubborn teens out of their shells, Wendy shows up at Jewell’s door and asks to meet Rion. In the young man’s room, Wendy notices that Rion has a knack for drawing. After looking at Rion’s art closely, she realizes one thing: the boy is OBSESSED with pussy. Drawing cunts in all shapes and sizes, it becomes fairly obvious for Wendy that her new patient needs a push to manhood to snap out of his shell. Determined to end Rion’s social awkwardness once and for all, Wendy teaches him all the right moves to become a master in the art of pussy-pounding.
Wendy Raine - College Admission Deception
Released: February 19, 2025
Wendy Raine is flabbergasted that her brilliant stepson, Elias Cash, isn't hearing back from the various colleges he's applied to. In fact, she takes personal offense to it. Not only is he at the top of his class, but he also does tons for the community and is even valedictorian for his year! When she discovers a hidden stack of acceptance letters in Elias' bedroom, however, she confronts him about it and demands an explanation for this senseless subterfuge. In a surprising turn, Elias admits that he doesn't want to leave home just yet... because he's got the hots for his stepmom! Wendy is flattered and, wanting him to get exactly what he needs to move on from the nest, gives him exactly what he's been craving.
Wendy Raine - Wendy Raine Gives Her Hapless Stepson Advice for Attracting Women
Released: August 28, 2024
Busty blonde MILF Wendy Raine heard her stepson fiddling away with his guitar and decided to check in to see how the lessons she's helped pay for have been working out, only to find out he's unable to play much of anything. When he confesses his interest in the guitar is solely to attract girls, Wendy decides to change tact and teach him how to attract them on his own. Sitting on his bed in her low-cut blue dress, she asks him bluntly what he has to offer these girls he's after. When his only answer is that he has a dick, she encourages him to take it out for her and is delighted by what she sees and wants to make use of it while they're alone in the house. She starts by sucking and stroking his cock, then strips naked and spreads wide for him to fuck her good and hard - missionary, doggystyle, and back to missionary, until he fills her up with a nice big creampie load.
Wendy Raine - Mature MILF Wendy Raine Cheers Up Her Jock Stepson With Wild Sex
Released: July 19, 2024
Busty Mature 51yo Blonde Wendy Raine makes her dazzling debut as a sexy stepmom, trying to console her stepson who's upset that his team just lost the game this afternoon - and he think if she'd been there, it may have turned out differently. Feeling bad and wanting to help cheer him up and get some confidence back in his step, she wastes little time in her seduction of him by just stripping off her tight green top to expose her heavy cleavage in a lacy purple bra, then pulling out her tits for him to suck on.
Wendy Raine - Big-titted, 51-year-old Wendy Raine fucks her son's big-dicked friend
Released: June 27, 2024
After a long day, 51-year-old Wendy Raine is in bed, about to use a toy on her pussy. She thinks she's alone. She thinks wrong. Her son's friend has come looking for him. Sonny isn't around, but that's okay with Wendy.
Wendy Raine - THE MISSING BATTERIES
Released: June 4, 2024
If masturbating is a crime, then GILF Wendy Raine is guilty as shit. This gilf is not only hot and horny but doesn't take kindly to strangers fucking up her masturbation time. That stranger would be Anthony - the younger stud who happens to hear a weird buzzing sound in the next room.
Wendy Raine - Wendy Raine is an impressive 51-year-old. Her sex skills are impressive, too
Released: April 25, 2024
James can't believe that Wendy Raine is 51 years old. The man has fucked a lot of MILFs, but he seems especially impressed by this hot wife. She likes that he's 29 because she likes young meat. She's going to get some in her mouth and pussy, and then she's going to get a young load on her face and in her mouth.
50PlusMILFs.com: What kinds of guys do you like?
Madison Wilde & Wendy Raine - 18th Birthday Gangbang Tradition
Released: April 25, 2024
TeamSkeet fans, you know we love you and your jaw-dropping ideas. That’s why the following scene originated from a fan-submitted idea we just couldn’t resist. It’s Madison’s 18th birthday and her family has a unique special tradition. Everyone participates in this rite of passage which involves fucking the birthday girl as a cleansing ritual to transform her into an adult. Madison couldn’t be more excited as her stepdad, stepmom, and other close relatives gather around her to have raw sex with her. All her holes will be pounded in this vital ritual/fuck session that will change Madison’s life forever!
Dee Williams, Andi James, Cyndi Sinclair & Wendy Raine - Gilfs & Young Studs Compilation
Released: March 29, 2024
What’s up, MYLF lovers? If you are here, it’s because you know that women are like fine wine. At MYLF, we don’t only feature the hottest milfs but also the wildest gilfs in the biz, especially those who love to teach young men a thing or two about pleasure. For this compilation, we have pieced together some of Andi James, Cyndi Sinclair, Dee Williams, Wendy Raine, and other vivacious vixens’ wildest moments, a true testament to how pussy gets better with experience.
Alexia Anders, Wendy Raine & Suki Sin - Everyone Cums Everywhere, All at Once
Released: March 11, 2024
Sukis life has become mundane. She cant quite remember when her happiness faded and every day became a slog, but nothing excites her anymore. Her stepfamily upsets her more than anything. They used to be the light of her life, and now theyre more like strangers occupying her melancholy world. Her stepdaughter, Alexia, is someone she doesnt recognize anymore. Alexia is brash and mysterious, and it only seems the rift between them is widening. Her husband, Leo, is aloof and out of touch with reality. Suddenly and without explanation, Sukis life seems to change.
Alexia Anders, Wendy Raine & Suki Sin - Everyone Cums Everywhere, All at Once Part 2: Everywhere
Released: February 25, 2024
Everyone Cums Everywhere, All at Once (Part 2 of 3): Suki has recently learned her universe is in great danger. After a sexual encounter with her stepson from another universe, things in her world are quickly unraveling. Suki is the only one who can save all the multiverses from imminent peril. Her next challenge comes as a surprise. Suki comes face to face with her stepdaughter, Alexia. Only this Alexia is all-powerful, and her sexual prowess is beyond imagination.
Alexia Anders, Wendy Raine & Suki Sin - Everyone Cums Everywhere, All at Once Part 1: Cum
Released: February 20, 2024
Everyone Cums Everywhere, All at Once (Part 1 of 3): Suki’s life is heading down a less-than-fortunate path. She has lost much of the joy she used to experience, and her stepfamily seems to be drifting further apart every day. Suki is a tough Tiger Mom, always demanding the best from her stepfamily and doing whatever it takes to keep them afloat. Her tough love has created a wedge in her relationship with everyone, and finding a resolution is getting more difficult. The family business and home are in danger of repossession, and unless they can sort out their taxes, they’ll lose everything they own...
Nicole Nichols, Sydney Paige, Maria Kazi, Jade Kimiko, Wendy Raine, Asia Lee, Reyna Belle, Lucky Anne & Bailey Blaze - Messy Cumshot Compilation
Released: February 18, 2024
What’s up, TeamSkeet fans? We love a Selects update, and this one is about to get a little messy. We’ve put together some of our favorite cumshot moments showcasing ultra-fine babes getting showered in jizz. It’s always fun seeing your favorite pornstars taking loads all over their bodies. Whether they’re getting pumped full of cum, or taking loads to the mouth and their tits, seeing them drenched in a hot sticky load is always a good time. See performances by Asia Lee, Bailey Blaze, Maria Kazi, Wendy Raine, and more!
Alexia Anders, Wendy Raine & Suki Sin - Everyone Cums Everywhere All At Once
Released: February 8, 2024
Suki’s life has become mundane. She can’t quite remember when her happiness faded and every day became a slog, but nothing excites her anymore. Her stepfamily upsets her more than anything. They used to be the light of her life, and now they’re more like strangers occupying her melancholy world. Her stepdaughter, Alexia, is someone she doesn’t recognize anymore. Alexia is brash and mysterious, and it only seems the rift between them is widening. Her husband, Leo, is aloof and out of touch with reality...
Wendy Raine - Raine To The Rescue
Released: December 7, 2023
Wendy gets a call from Principal Miles, and things are not looking so good at the school. Apparently, Wendy’s son has been causing trouble and could face severe consequences for his tomfoolery. Wendy is willing to go to any length to save her son, and it seems the length this time around is probably around eight or nine inches. Franky put, Miles, wants to fuck this bodacious milf, and if she does, he may be able to pull some strings. Wendy is all game and takes dick like a champ, so this is a no-sweat situation. The two get right to fucking, and Wendy has some fun getting fucked in the office. She knows what she’s doing is taboo, and things will look even worse if they get caught. But that’s half the excitement, and she loves every second of their wild sexcapade.
Wendy Raine & Lucky Anne - The Lucky Rebel
Released: November 9, 2023
Wendy has always been careful about introducing Lucky to her step-uncle, Nicky. Wendy explains that Nicky has always been a turbulent guy - someone who is mischievous and takes what he wants. However, when Wendy and Lucky get a flat tire, they have no choice but to call Nicky for help. Nicky takes immediate notice of Lucky. She’s a curvy babe with an ass so mouth-wateringly intense that it barely fits in the skimpy shorts she is wearing. Lucky notices Nicky, too. Her step-uncle is kind of hot, and maybe he’s got a big dick...
Wendy Raine & Aaliyah May - Resort MILF Loves A Squirter
Released: September 25, 2023
Hot blonde MILF Wendy Raine thought she and her husband would have some quality time together on their resort vacation, but all he wants to do is play games on his phone. Luckily, hot redhead employee Aaliyah May strolls by and gets Wendy's attention. She tips the waitress with a flash of her big tits, then walks in on her in the employees-only bathroom and licks her pussy! She brings the sexy teen back to her room and makes her squirt, and they lick each other and scissor around a vibrator. Best vacation ever!
Wendy Raine - Sexy Redhead Milf Wendy Raine Takes Her Son's Friend's Cock For A Ride
Released: September 8, 2023
Wendy Raine is making breakfast for her son and to her surprise he's not home, but his friend, Logan, is and boy is he hungry. Logan and Wendy's son have an inside joke going that they'll fuck each other's mom's when given the chance. Wendy over hears about it and wants Logan's cock to see if it's up to the task. Watch this sexy milf fuck and suck this hard cock and make it explode with hot juicy cum.
Wendy Raine & Renee Rose - Not-So-Bad News
Released: August 17, 2023
Gi Joey’s day couldn’t get any worse. First, he found out that Renee is not his biological daughter, and to make matters worse, she has just told him his wife Wendy has been cheating on him. Depressed, he decides to forget about it all and have sex with Renee, something they both desired for a long time. Even when Wendy finds the girl giving Joey a blowjob, he just doesn’t care–he will get a taste of that sweet pussy now that he is free to do it.
Wendy Raine & Jade Kimiko - MILF Cleans Up Gamers Act
Released: July 10, 2023
Blond MILF Wendy Raine may only have been a stepmom for a month, but she's already fed up with how her stepdaughter, Jade Kimiko, spends all her time gaming instead of doing her chores! Dark-haired Jade doesn't want to hit pause to clean the bathroom, but she enjoys it a lot more when Wendy comes in to play with her little tits and rub her pussy! The hot stepmom licks Jade, and the teen returns the favor. Good thing Jade just cleaned the floor so they can scissor on it!
Wendy Raine - Wendy Raine Jizzed Sprayed
Released: April 21, 2023
Wendy Raine wishes to have a big hard cock and guess what: That’s exactly what she gets! This blonde GILF gets naked and starts sucking that handsome guy’s dick before riding it on the couch of her house.
Wendy Raine - Shady Spa - Wendy
Released: April 19, 2023
Today is Wendy’s first day at work and she wants to make a good impression. When her first client asks for a happy ending massage, that sexy milf can’t say “no”, so she grabs his cock and starts to suck it while massaging his balls. Soon that handsome man is going to explode with cum and Wendy will get a 5-star review.
Maya Woulfe & Wendy Raine - College Slut Gets Anal Dildo For Dinner
Released: March 13, 2023
Blonde MILF Wendy Raine doesn't care about meeting her boyfriend's daughter--she just wants to get fucked. But when hot coed Maya Woulfe shows up while Wendy's playing with herself and sucking a dildo in the kitchen, she decides to do both! Maya's immediately in as her new stepmom pulls her face into her big tits and rubs her pussy, then gives her a dildo to sit on at the table. Wendy brings the little slut upstairs to penetrate her tight ass with a dildo and then puts on a strap to give her a nice hard fuck!
Wendy Raine - Busty cougar Wendy Raine is amazed by her boyfriend's son's big cock
Released: January 21, 2023
Parker is printing some pics to give his sweetheart for Valentine's day when his dad's girl, Wendy walks in. As Parker is printing the pics, Wendy catches a glimpse of a dick pic. She refuses to believe that a cock that big can belong to Parker so she demands to see his member. Parker finally agrees and it is as big in real life as it is in the picture. Wendy can't help herself so she takes that cock right there and then.
Wendy Raine - Fresh Nana
Released: January 17, 2023
Wendy is newly single and she’s dying to get back in the game but it’s been a while since she last saw a young cock so she asks her stepgrandson Nicky for help. Nana has some huge tits so it’s not hard at all for Nicky to finger-bang her and let her blow him!
Slay Savage & Wendy Raine - Horny Daughter Steals Hot MILF's New Husband
Released: December 29, 2022
Mandy comes home from nursing college and meets her new stepdad, Brickzilla. Her mother Wendy thinks she is being sneaky as she jerks off her new husband, but once Mandy catches on – she has some plans of her own. She sneakily teases and taunts Brick until she has full control of her new stepdad’s massive cock!
Khloe Kapri & Wendy Raine - Nana's Kinky Secret
Released: December 10, 2022
Nicky has been having trouble with making his girlfriend Khloe cum so they meet with Nicky’s Nana Wendy to get some guidance. Nana offers to show Nicky exactly what to do to pleasure Khloe and her hands-on approach leaves everybody thoroughly satisfied!
Seka Black & Wendy Raine - Neighborhood Cougar Rivalry
Released: November 18, 2022
Seka is the high queen of her suburban neighborhood, until social climber & new challenger Wendy moves in across the street. Seka has hired local hunk & oddjobber Hollywood to mow her lawn & provide her with some afternoon eye-candy. But as Wendy spies Hollywood, she has designs of her own. As the girls plot to undermine each other, Hollywood gets persecuted with various teases & sexual favors from the neighborhood cougars. One thing leads to another & naturally the women decide to share their prey in a highly inappropriate threesome with anal!
UPDATED Wendy Raine - Step Mommy teaches me a Lesson
Released: October 21, 2022
Johnny has been home for a long time and Wendy told him to clean up his mess before she arrives problem is Johnny forgets and doesn't feel like it so his stepmom decides to give hm a lesson he will never forget. You wanna be a dirty boy Johnny, Step mom is gonna clean you right up.
