https://jerkwell.com/categories/roleplay-costume/ Sun 25 Oct 2026 06:45:07 +0200 https://jerkwell.com/videos/8206/surprise-dinner-for-step-mom-jodie-johnson-monica-minx/
Jodie Johnson comes across his mom Monica Minx clattering plates around. He learns that his dad flaked on her for date night and offers to help her out by putting the dishes away. Later, Monica walks in and finds Jodie setting the table. He ordered pizza to make up for his dad being a dick. Monica rushes to change into a dress fit for a dinner date. When Jodie apologizes that he forgot to order dessert, Monica knows what to do. She claims he can eat her for dessert, and sweetens the deal by popping her big tits out. Soon, Jodie has moved from squeezing his mom's tatas to being buried face first between her thighs. Wanting some dessert of her own, Monica sucks her step son's fuck stick. There's no question these two are going to go at it like bunnies. Monica kicks their after-dinner delight off leaning forward on a chair to take Jodie in doggy. Then she gets on the table so Jodie can step between her thighs and keep her pussy party going. After riding Jodie in reverse cowgirl and then cowgirl, Monica hops off the D and strokes the cum right out of Jodie's hardon so she can enjoy a real treat. ]]> Fri 09 Oct 2026 00:24:34 +0200 https://jerkwell.com/videos/8206/surprise-dinner-for-step-mom-jodie-johnson-monica-minx/ https://jerkwell.com/videos/8185/are-you-man-enough-to-be-with-me-step-son-jessica-aaren-rion-king/
Jessica Aaren is getting all stretched out and ready for her yoga workout. Dressed in clothes that highlight her huge tits and big ass, she's on her knees on the ground with her booty up when her step son Rion King comes in. Rion takes that opportunity to confess his feelings for his step mom. Fortunately for Rion, Jessica had earbuds in and she claims she didn't hear him. Rion won't repeat it. Later, Jessica comes to Rion's room to share that she did in fact hear him but she wanted him to be man enough to say it to her face. She also needed to wait until they were alone because she wants him. She puts Rion's hand on her tits, then shrugs her robe open to show that she's nude. Jessica doesn't waste time before stroking Rion's hardon and then leaning in to suck him down. Straddling Rion's hips, Jessica sinks down to ride in cowgirl. She turns around for reverse cowgirl, then gets on her knees so Rion can dick her down from behind. On her back, Jessica splays herself out so Rion can eat her pussy and then shove back into her. Now that Jessica is sated, she gives Rion a nice titty fuck and handie that leads him to blow his load on her big tatas. ]]> Thu 08 Oct 2026 19:00:53 +0200 https://jerkwell.com/videos/8185/are-you-man-enough-to-be-with-me-step-son-jessica-aaren-rion-king/ https://jerkwell.com/videos/8181/mom-is-jealous-of-my-girlfriend-rion-king-savanah-storm/
Rion King promised his mom Savanah Storm that he'd fix the leak under the sink, but he's busy on the phone with his new girlfriend. Savanah is bitchy about the lack of help she's getting from her step son. Rion points out that she's acting jealous. Although Savanah claims that's totally not true because she's a real woman, she does get an idea of how to fix the situation. Dressing up in a sexy outfit, Savanah comes to try to coax Rion into staying in with her for the evening. When that doesn't work, she claims she lost her earring and asks Rion to help her retrieve it from where it's stuck in the couch. As soon as Savanah can tell Rion has a boner, she reminds him that he needs a real woman and then tugs his dick out to suck him off. Rion is putty in Savana's hands as she gets on the couch and spreads herself wide open to get him to eat her pussy. After another BJ and titty fuck, Savanah sits Rion down and climbs aboard to ride him in cowgirl. A reverse cowgirl ride comes next, with that big ass there for the squeezing as Savanah goes to town. Doggy style is next, and then Savanah gets on her back to let Rion bring her off one final time. Another titty fuck gets Rion to blow his load. ]]> Thu 08 Oct 2026 17:43:38 +0200 https://jerkwell.com/videos/8181/mom-is-jealous-of-my-girlfriend-rion-king-savanah-storm/ https://jerkwell.com/videos/8125/welcome-home-baby-matty-mila-perez-francis-x/
Matty Mila Perez greets her boyfriend Francis X in a tight pink dress, but the real treat comes when she hikes it up to show off her matching thong. The dress barely covers anything, and the Asshole Fever series makes sure you get a clear view of what's underneath. She's all smiles, ready to give him a very personal welcome home. ]]> Tue 06 Oct 2026 21:02:09 +0200 https://jerkwell.com/videos/8125/welcome-home-baby-matty-mila-perez-francis-x/ https://jerkwell.com/videos/8115/mistaken-mouthful-andi-avalon-selina-bentz-taylor-wild/
Andi Avalon invites Taylor Wild over for a hookup while her step daughter Selina Bentz is out. Things get messy when Selina comes home early, blindfolded Andi mistakes her for Taylor, and they start going at it. Once Taylor returns, the shock makes her bolt, but Andi and Selina laugh it off and keep going. This one's from Girlsway's Mommy's Girl series, and the mix-up leads to some wild roleplay turns. ]]> Tue 06 Oct 2026 17:41:08 +0200 https://jerkwell.com/videos/8115/mistaken-mouthful-andi-avalon-selina-bentz-taylor-wild/ https://jerkwell.com/videos/8041/learn-to-love-easter-family-slut-punished-anastasia-shades-debut-anastasia-shades-gia-ohmy-nicky-rebel/
Anastasia Shades gets called out by her mom Gia OhMy and step dad Nicky Rebel for acting too slutty around Easter. The Family Strokes series takes it further with a threesome punishment at home, all about teaching her how to honor family traditions. The whole thing's a holiday-themed taboo mess with roles played out hard. ]]> Mon 05 Oct 2026 14:58:00 +0200 https://jerkwell.com/videos/8041/learn-to-love-easter-family-slut-punished-anastasia-shades-debut-anastasia-shades-gia-ohmy-nicky-rebel/ https://jerkwell.com/videos/7977/you-can-t-keep-dressing-like-this-danielle-renae-tyler-cruise/
Danielle Renae keeps pushing the limits with her outfits in Mommy's Boy, starting with side-boob and no bra, then no panties with a bikini top that barely covers anything. Tyler Cruise can't take it anymore and finally snaps, ending the tension with sex. The build-up is as good as the payoff, with her revealing clothes driving him wild. ]]> Mon 05 Oct 2026 14:05:19 +0200 https://jerkwell.com/videos/7977/you-can-t-keep-dressing-like-this-danielle-renae-tyler-cruise/ https://jerkwell.com/videos/7945/the-tale-of-slutty-mary-juan-el-caballo-loco-scarlett-alexis/
Scarlett Alexis tells Juan El Caballo Loco a spooky story in the Bratty Sis series, teasing him until their parents interrupt. The next day, he summons a ghostly figure, and Scarlett in a costume takes over, leading to sexual acts in the mirror. The setup is playful, then it turns into something hotter than expected. ]]> Mon 05 Oct 2026 13:37:24 +0200 https://jerkwell.com/videos/7945/the-tale-of-slutty-mary-juan-el-caballo-loco-scarlett-alexis/ https://jerkwell.com/videos/7925/open-house-reunion-isa-bella-jazmin-black-donnie-rock/
Jazmin Black recognizes her old college bestie Isa Bella at an open house, and the vibe between them gets extremely flirty. Isa drops the bomb that Jazmin is bi and they used to hook up, so the women start kissing and undressing on the couch. Before long, Donnie Rock gets roped into a threesome, fucking both of them in this Property Sex reunion. ]]> Mon 05 Oct 2026 13:20:02 +0200 https://jerkwell.com/videos/7925/open-house-reunion-isa-bella-jazmin-black-donnie-rock/ https://jerkwell.com/videos/7878/naughty-nurse-femboy-gets-physical-from-boyfriend-leo-louis-jazzz/
Jazzz is just hanging out in his bedroom when his boyfriend Leo Louis walks in with a gift for getting into nursing school. It's a nurse costume, and Jazzz laughs because it looks more like a gift for Leo, but he ends up wearing it anyway. They have a fun, physical time together, and Jazzz calls him good girl a few times. It's part of the Femboyish series on AdultTime, so you know exactly what kind of fun they're having. ]]> Mon 05 Oct 2026 00:59:41 +0200 https://jerkwell.com/videos/7878/naughty-nurse-femboy-gets-physical-from-boyfriend-leo-louis-jazzz/ https://jerkwell.com/videos/7873/neighbor-s-needs-emma-rose-alison-rey/
Emma Rose gets all dressed up for a date that falls through, and her neighbor Alison Rey comes over to borrow a cheese grater. She notices Emma's outfit has no panty lines, so Emma admits she's not wearing any. That leads to a quick, no-strings hookup right there in the Transfixed series. The setup is simple, but the payoff is obvious. ]]> Mon 05 Oct 2026 00:39:03 +0200 https://jerkwell.com/videos/7873/neighbor-s-needs-emma-rose-alison-rey/ https://jerkwell.com/videos/7833/stepmoms-secret-life-s25-e3-desiree-dulce-rion-king/
Desiree Dulce dresses up in a way that makes Rion King suspicious she's working as a call girl. When he confronts her, she takes him to the bedroom and shuts him up with oral, multiple positions, and vaginal sex. After he finishes on her, she reminds him he can't tell his dad now that he's involved. It's all in Moms Teach Sex. ]]> Sun 04 Oct 2026 22:34:38 +0200 https://jerkwell.com/videos/7833/stepmoms-secret-life-s25-e3-desiree-dulce-rion-king/