https://www.transhero.com/tags/supervised-sex/ Tue 14 Apr 2026 19:04:01 +0200 https://www.transhero.com/videos/347782/my-deepest-secret-sex-lessons-from-stepmom-stepsis-aaliyah-love-gigi-sweets/
I shouldn’t be writing this down because I don’t think I’ll ever be able to really tell anyone about it… Recently, I’ve started fucking around with my stepmom AND my stepsister. They found out that I’m not Mr. Popular at school and that my experience in the realm of girlfriends is less than satisfactory. It’s not that I’m a nerd or anything… I’m just shy and never really know what to say. I guess my stepmom had an immediate plan, though, because she and my stepmom showed up in my bedroom and jumped into bed with me. I knew right away something was up, but when I had my stepsister’s tongue in my mouth, that was the clear sign that things were about to get way, way more fucked up. Is it wrong that I never want this to end? That I wish I could fuck my stepmom and stepsister forever? Everything about them is so familiar and perfect. Finally, getting to see Gigi’s perfect rack has been like heaven, and I’d give up all the riches in the world to fill up my stepmom’s pussy for the rest of my life. I know it’s wrong, but holy fuck - I am in love with their pussies! ]]> Mon 09 Mar 2026 00:19:00 +0200 https://www.transhero.com/videos/347782/my-deepest-secret-sex-lessons-from-stepmom-stepsis-aaliyah-love-gigi-sweets/ https://www.transhero.com/videos/242088/game-night-gets-steamy-when-stepsiblings-play-pristine-edge-romi-rain-dana-vespoli/
Murder She Moaned (part 3 of 4): This investigation keeps getting kinkier and kinkier. But I haven’t seen enough yet. I need to see things play out in front of my very eyes. Luckily, I think Axel and Rion can help me in that department. I have a fucked up little swap plan that’ll give me a clearer picture of the fucked up dynamic in this stepfamily. But will these guys really fuck their own stepmoms? Of course, they will - once they see those beautiful bodies, they won’t be able to resist… ]]> Sat 28 Feb 2026 03:43:37 +0200 https://www.transhero.com/videos/242088/game-night-gets-steamy-when-stepsiblings-play-pristine-edge-romi-rain-dana-vespoli/ https://www.transhero.com/videos/161044/kiss-and-make-up-then-we-fuck/
Venus and her stepbrother are always bickering. The pair seem to have some sort of weird attraction towards each other, but their sibling rivalry gets in the way. Their stepmom, Madison, is tired of hearing the two of them arguing all the time and finally puts her foot down. After reading a TeamSkeet book on family discipline, Madison has all of the answers she’s been looking for. She starts by making Venus and Parker kiss. It’s a weird sensation, but it makes Venus super horny. She can’t believe she’s doing something as wrong as kissing Parker, who she has known forever as her stepbrother. Parker is also turned on but knows it’s wrong. Madison sees that their kiss has made them hot and heavy, so she leans into it and makes the stepsiblings go all the way. Plus, Madison likes it just as much as they are, and the horny milf is feeling slutty and down to see how far she can take this fling. Parker sucks on his stepsister’s perfect tiny nipples and fits her titty in his mouth. It’s weird and fucked up, but no one wants the threesome to stop because everyone is feeling extremely turned on. Parker moves downstairs and goes to town on his stepsister’s pussy, lapping up her juices and sucking on her clit until he has her shrieking with delight. The petite chick has never known pleasure like this and is feeling super kinky and slutty at this moment. Madison watches as her perverted plan unwinds. Soon, the group can’t stop fucking around with each other, and it isn’t long after that Venus has Parker’s cock deep down her throat. He pushes himself deeper, and Venus doesn’t stop blowing him until he shoots his load. Madison watches, and she can feel herself getting wet. She wants a turn with Parker, and it would be even hotter if she could mess around with Venus, too. In the bedroom, Venus and Madison tend to Parker’s throbbing cock. Never in a million years did he imagine he’d be getting his cock sucked by his milf stepmom and cute stepsister, but he knows he has to prove himself and fuck the both of them as they’ve never been fucked in their lives. The girls prove to be total powerhouses, and they ride his cock like pros, taking every inch, building him closer and closer to climax. Venus thrusts her sweet hips around as she rides him, knowing she’s making it hard for her stepbrother not to cum. Madison is impressed by her stepdaughter’s slutty skills and can’t wait to get a taste of her dripping wet snatch. When Parker can’t hold his load any longer, he cums hard for the girls, giving them a frothing shot of hot white nut. ]]> Mon 23 Feb 2026 10:56:33 +0200 https://www.transhero.com/videos/161044/kiss-and-make-up-then-we-fuck/ https://www.transhero.com/videos/342994/starring-nickey-huntsman-pristine-edge-romi-rain-more/
Nickey Huntsman, Pristine Edge, Romi Rain, Dana Vespoli, Aderes Quin, Jack Vegas, Mike Mancini, Rion King, Axel Haze ]]> Sat 21 Feb 2026 02:40:21 +0200 https://www.transhero.com/videos/342994/starring-nickey-huntsman-pristine-edge-romi-rain-more/ https://www.transhero.com/videos/328571/the-step-mom-swapping-talk-show-takes-a-wild-turn/
Welcome back to the hottest show on television, where we take a look at the lives of the kinkiest MILFS in the world. Today, we are joined by Harper and London, who decided to rebel against society’s most outdated norms by letting their hot stepsons fuck their brains out. After all, if these hunks are gonna go around fucking whatever slut hey encounter, why not pound their horny stepmoms first? To make it even more interesting and kinky, we challenged both of them to swap stepsons for the evening… and oh boy, things are about to get really dirty over here! ]]> Fri 20 Feb 2026 18:17:48 +0200 https://www.transhero.com/videos/328571/the-step-mom-swapping-talk-show-takes-a-wild-turn/ https://www.transhero.com/videos/256907/fucking-my-boss-in-front-of-his-wife-yes-please/
I thought these people were crazy! Having sex with my boss in front of his wife was not on my Bingo card. I've always been in love with him, and I knew he was married, but that didn't stop me from wearing revealing clothes in front of him. When he finally took me to dinner, I was so excited that my pussy was wet the entire time. Then, he took me to his house for dessert, and that's when I learned his wife knew about us and was waiting for me in the bedroom: My pussy was the dessert! At first. I was nervous, but I've always wanted to fuck my boss, and his wife was making me wet just by wearing the most revealing, sexiest lingerie I've ever seen. If they both look like that, they can use my body however they want. ]]> Thu 12 Feb 2026 11:10:26 +0200 https://www.transhero.com/videos/256907/fucking-my-boss-in-front-of-his-wife-yes-please/ https://www.transhero.com/videos/121786/hot-milf-films-with-top-stars-ride-hard-cum-harder/
What’s up, Mylf lovers? You know the feature films here are always balls to the wall. Murder She Moaned, Motherfucker, Everyone Cums Everywhere, All at Once, The House Bunny - you name it, it’s here! The most captivating Milf superstars, like Cory Chase, Pristine Edge, Romi Rain, & Sheena Ryder, are getting fucked out of their minds, riding hard cock until they’re covered in a hot sticky load. It doesn’t get better than MYLF Features, as these movies are us at our zenith. When you’re done with this Selects scene, head over to the MYLF Features page for round two… ]]> Sun 08 Feb 2026 15:23:53 +0200 https://www.transhero.com/videos/121786/hot-milf-films-with-top-stars-ride-hard-cum-harder/ https://www.transhero.com/videos/386722/cuck-girlfriend-catches-cum-dumpster-bff/
Sona lives in a fairy tale world. Her boyfriend Peter is just the best, and her BFF Aria loves her like no one. Yet, Sona wants them to get along too, so she plans the perfect date night with them. The plan goes too well, as Aria and Peter can’t get their eyes off each other. At a moment of distraction, Peter and Sona go to the room, leaving Sona behind. Worried, Sonia goes to see what’s going on, only to find her boyfriend filling out her best friend. At first, she is mad and jealous about the whole situation. She doesn’t know if she should interrupt the whole kinky show, so she watches from a distance. As the room gets hotter, Sona decides to film the treason, but she starts to become aroused by seeing Peter play with Aria’s pussy. He never showed that rough side of his with her, so watching him fuck Aria in the kinkiest way possible makes Sona hornier. Finally, she decides to come in, but she doesn’t join them, as she prefers to watch the scene and comment on it. ]]> Sun 08 Feb 2026 13:56:46 +0200 https://www.transhero.com/videos/386722/cuck-girlfriend-catches-cum-dumpster-bff/ https://www.transhero.com/videos/120297/exercising-trust/
Amber and Luxe are best friends, but got into a huge fight during class over a boy so now they both got detention. It’s up to their counselor, Mr. Rock to make sure these two make up and get along. The counselor senses that the two girls lost trust in each other, so he tries some exercises so they can rebuild their friendship. Each new exercise is more physical than the previous one until Amber and Luxe find themselves so close that they are playing with each other’s pussies. Happy about being friends again, the girls decide to thank Mr. Rock with a hot double blowjob. The counselor sits back as the horny gals relish his dick together, eager to let Donnie plow them during detention. ]]> Tue 03 Feb 2026 09:31:21 +0200 https://www.transhero.com/videos/120297/exercising-trust/ https://www.transhero.com/videos/136760/swap-to-make-amends/
Roxie and Pierce are always bickering, and that’s no way for a stepdad and a stepdaughter to behave. To mend their relationship, they seek help from Quinton and Natalie. Quinton is trained in helping families get their acts together, and his stepdaughter Natalie is always there to help. Quinton’s methods are beyond unorthodox, but somehow, he always knows the solution. Quinton’s tactics for Roxie and Pierce continue to become more and more sexual until, eventually, he has the two right up against one another, with Pierce’s cock essentially edging Roxie’s pussy. Pierce has to try not to get hard while Roxie’s perfect tits are pressed up against him. It’s a wild sensation, being skin-to-skin with his stepdaughter, and both Roxie and Pierce are feeling turned on, even though they know it’s wrong. To make the exercise a little easier, Quinton proposes a Daughter Swap. Pierce can get comfy and sexual with Natalie, while Quinton gives Roxie attention. Soon, both girls are sucking cock, and it isn’t long after that they’re riding cock. When Roxie and Pierce feel ready, they swap back, so now Pierce will have the opportunity to fuck his own stepdaughter. They know it’s taboo, but the exercise brings them closer than ever. ]]> Tue 03 Feb 2026 06:04:44 +0200 https://www.transhero.com/videos/136760/swap-to-make-amends/ https://www.transhero.com/videos/265334/dana-vespoli-and-mike-s-scandalous-secrets-revealed/
Murder She Moaned (Part 2 of 4): It’s time to shift my focus to Dana and Mike. They’re just as suspicious as everyone else, and I want to know every dirty detail of their fucked up sex life. It turns out that Mike and Dana like to have a little fun in the bedroom with other women. I knew Dana was freaky, but I didn’t know she liked to watch her husband fuck other women… They filled me in on every detail of how Mike filled up Aderes’s sweet pussy. Getting to cum inside of a personal assistant to the family must have been fun for Mike. Just imagining Aderes taking Mike’s cock, submitting to him completely. I could feel my pussy getting wet again… This case just keeps getting steamier and steamier. ]]> Thu 22 Jan 2026 01:38:44 +0200 https://www.transhero.com/videos/265334/dana-vespoli-and-mike-s-scandalous-secrets-revealed/ https://www.transhero.com/videos/338691/anal-dare/
Trinity, Nicky, and Melody play a game of truth or dare on the couch. They pull from a hat to lead their game, but things start taking a vert sexual turn. Soon, Nicky finds himself with his cock out in front of his wife and her stepmom. Trinity isn’t going to do anything she’d save for the bedroom in front of her stepmom, but Melody has no such reservations, and after seeing Nicky’s cock, the horny milf wants a piece for herself. Nicky fucks Melody in the ass, shocked that he’s fucking his mother-in-law at all. Never in a million years could he suspect that he’d one day pound on his mother-in-law’s backdoor, all in front of his wife. The babes love the sexy fling that’s happening, and their pussies are dripping wet. Nicky cums hard for Melody as his wife watches on the sideline. ]]> Wed 21 Jan 2026 04:58:57 +0200 https://www.transhero.com/videos/338691/anal-dare/