Video Description: You'd think someone on house arrest would be terrified of their parole officer coming around. But when it comes to Dana Vespoli, she absolutely loves it. You see, Dana and her parole officer, Penny Barber, have a special arrangement... Dana 'steps' outside of the perimeter of her home, her ankle bracelet goes off, and then Penny comes by to 'punish' her... with rough, sensual sex including naughty facesitting and plenty of strap-on fucking.

Video Description: Penny is happy to have an affair, but she isn't willing to risk getting caught for a chance at some dick. For a chance at two dicks, on the other hand...

Video Description: Penny Barber has invited her old friend, Lexi Luna, over to her house to catch up. It's been ages since they've seen each other, so they have LOTS to talk about. After making themselves comfortable in the living room, they start dishing out all the hot gossip that they've amassed over the last few years. It turns out that they've both gone through messy divorces, which isn't that bad since they both ended up with lovely stepdaughters, whom they love dearly. The hottest piece of gossip yet, however, is that they're both currently in relationships with sugar babies!After bragging about each other's sugar-babies for a bit, Penny reveals that HER sugar-baby stayed the night. In fact, she can hear her stirring upstairs... Would Lexi like to meet her? Lexi says that she'd LOVE to, so Penny calls her sugar-baby, Natalie Brooks, downstairs. But when Natalie comes into view, Lexi and her are shocked to see each other, since Natalie just happens to be Lexi's STEPDAUGHTER! To make matters worse, Penny's stepdaughter, Chloe Surreal, comes home from work and immediately recognizes Lexi, who happens to be her SUGAR MAMA! Oh no... this can't be happening... Penny and Lexi's sugar-babies are each other's stepdaughters! What are the odds?!All four of them try to sit down and diffuse the situation, but it only ends up making things more awkward. Having had enough, Natalie runs off to Penny's room, with Penny following her in desperation. Lexi lingers for a moment, but then runs off to follow Penny and Natalie, leaving a stunned Chloe downstairs. But when Lexi stumbles into Penny's room, she finds Penny and Natalie making out! Wow- the nerve on these two! Things take an interesting turn, however, when Natalie invites her stepmom Lexi to join in for a threesome. It's a wild suggestion, but Lexi can't help but eventually give in to temptation... having a steamy sex session she'll never forget.

Video Description: Jewell has issues with her stepson, Anthony. Hes a total perv and cant control his cock, hes looking to fuck 247, and its become an issue. Luckily, perv therapist Penny Barber is there to help. Penny is the best in the business, and her unorthodox tactics have been helping perverted stepfamilies conquer their issues for years. Jewell explains her concerns about Anthonys behavior. Penny sees a different side of things. Pennys guess is that Jewell and Anthony may need a little stepfamily playtime. After all, maybe Jewell is jealous, and she wishes it were her getting the dick down from her stepson. Jewell had never thought about it before, but having Anthony deep inside of her, pleasing her pussy, and making her squeal did sound like a good time, even if it was completely fucked up and taboo. Penny puts the stepmom and her stepson right to work. Its a wild sensation, but Jewell loves having Anthonys cock in her mouth. Its a weird blowjob, but easily one of the best Anthonys ever had, it being forbidden adds to the thrill. Penny joins in on the fun, making for an incredible and heart-pounding threesome. Anthony has his work for him to keep up and please both milfs, but he puts his best foot forward. Anthony cums hard on his stepmoms tits, shooting rope after rope of jizz onto her.

Video Description: A teen, Tyler Cruise, has recently begun dating a girl, Freya Parker, and Freya has mentioned that she likes dirty talk. But Tyler is TERRIBLE at dirty talk, and goes to his stepmom, Penny Barber, for tips. That's when Penny hatches a WILD plan Tyler will secretly wear an earpiece next time he and Freya have a date. Penny will hide nearby, watching and feeding Tyler dirty talk lines through the earpiece. With her help, Tyler will be able to give Freya all the juicy dirty talk she could ever want...When they enact their plan the next day, everything goes smoothly at first, with Freya really getting into it. But eventually, Tyler flubs one of Penny's lines, comically saying that he wants to KICK Freya's tits instead of LICK.Caught red-handed, Penny comes out of hiding and they explain their plan to Freya. But, much to the surprise of Tyler and Penny, Freya isn't mad. In fact, she's so turned on by Penny's silver tongue that she invites her to put that tongue to good use in a threesome!