Genre: Family, mommy, Mommy Roleplay, POV, Role Play, Taboo, taboo mommy, Virtual Sex, Olive Wood
Video Description: Your step-sister is worried about Mommy. Although it’s hard to keep track of her dating life, your step-sister suspects she’s been dumped by one of her much younger boyfriends and the rejection has hit her hard. Sis knows Mommy thrives on the validation she receives from young men and thinks you ought to help boost her spirits by paying her a compliment. You don’t particularly enjoy dealing with Mommy during her depressive episodes, but Sis makes you an offer you can’t refuse (a blowjob) and sends you off to Mommy’s room with a kiss. Mommy throws the door open half-naked and demands to know if anyone has come to call for her. You shake your head and she sighs, ushering you in as she attempts to cover herself with a robe and apologizes for her sorry state. As she begins to lament about her recent breakup, you blurt out your step-sister’s request verbatim and tell Mommy you think she’s beautiful. Mommy immediately perks up and begins to fish for more compliments. She goes on about her love for younger men and adds that if you weren’t her step-son, she’d date you in a heartbeat. You assure her the feeling is mutual and the two of you embrace. You’re humiliated when Mommy pulls away and gleefully points out your growing erection. She promises you it’s nothing to worry about, in fact, one of her favorite things about young men is their insatiable appetite for sex. It’s perfectly natural for a boy your age to find her arousing, so perhaps it wouldn’t be wholly UNnatural for her for tend to your urges. Mommy steps closer and unzips your pants. She gets on her knees and begins to suck your cock before climbing onto her dresser and ordering you to stroke yourself as she fingers her pussy and gets it ready for you. She teases you for what feels like an eternity before pulling you in and wrapping her legs tightly around you as she guides you inside her. She uses lots of everyone’s favorite “I” word as she reminds you you’re back inside the body that birthed you, and climaxes as she enthuses about her new family kink. Mommy flips over so you can take her from behind and watches herself in the mirror as you push yourself inside her even deeper than before. She turns around and begins to kiss you, dragging you into bed as she encourages you to continue in missionary position. The two of you take turns on top, and you find you especially enjoy watching Mommy’s big round breasts bounce up and down as she rides you. When you can no longer hold in your orgasm, Mommy rolls back over and begs you to come inside her, which you do without hesitation. You leave Mommy’s room and suddenly remember the deal you made with your step-sister. She corners you as you head towards the bathroom to clean up and demands to know how Mommy doing. You explain that Mommy is doing well, in fact, she seemed to be glowing when you left the room. Sis is so proud of you that she offers you your payment on the spot. She takes your cock between her hands and notes that you taste and smell especially good. Although she can’t quite pinpoint the flavor, the combination of your semen mixed with Mommy’s pussy drives her wild with desire as she hungrily slobbers on your cock and brings you to orgasm once more.
Genre: BDSM, Bondage, chained, Family, OliveWood, reluctant, Role Play, siblings, Taboo, Olive Wood
Video Description: Custom commission. TRIGGER WARNING. While studying to become a therapist, your struggling step-sister takes on a job at a sketchy "lingerie therapy" company. After moving to the other side of country to get away from you, she'd never suspect that her strange, masked client is YOU. She tries to run, but it's too late. You've had your entire life to plan her captivity and there's nothing she can do but surrender control. (Not a ton of sex in this one, as the customer who commissioned it specifically did not want any)
Genre: Family, mommy, Mommy Roleplay, POV, Role Play, siblings, sister, Son, Taboo, taboo mommy, Virtual Sex, Olive Wood
Video Description: You have no memories of your mother. Mommy left you with your big sister when you were young and all youve ever known is Sis. The two of you have developed a unique bond as shes grown into the role of your caretaker and more recently, your lover.
Genre: Daddys Girl, Family, POV, Role Play, Taboo, Virtual Sex, Olive Wood
Video Description: There's only room for one man in her life and it isn't her new husband, it's you.
Genre: Aunt, Family, first time, Mommy Roleplay, Older Woman Younger Man, Pantyhose, POV, Role Play, Taboo, virginity, Virtual Sex, Olive Wood
Video Description: Your aunt has never approved of her sisters strict parenting style. When you come to stay for the weekend, she makes it her mission to get you out of your shell and teach you what it feels like to finally be treated like a real man.
Genre: cumshot, Cumshots, Facial, GFE, MILF, Olive Wood, POV, Role Play, wife, Witch
Video Description: Your witch wife struggles to find an antidote after an erection spell goes awry and lands you with a boner that wont subside.
Genre: Bondage, Family, lingerie, Olive Wood, POV, Role Play, siblings, sister, Sisters, Taboo
Video Description: Your sister is furious when she wakes up and finds youve chained her to her bed. What a CREEP you are. This was a custom commission in which your name is Jeremy. VIEWER DISCRETION ADVISED.
Genre: daughter, Family, niece, Older Man Younger Women, POV, Redhead, risky, Role Play, Taboo, uncle, Virtual Sex, Olive Wood
Video Description: Your sister has invited you to crash on her sofa while youre in town. Concerned the accommodations her mother has offered might not be up to par, your niece tiptoes into the living room in nothing but a T-shirt and offers to share her bed with you. You begin to panic. Since arriving for your visit, youve tried your hardest to avoid direct eye contact with her. Shes far too pretty for comfort and letting your guard down in her presence takes your mind to places youd rather not go. Now cornered and defenseless, you begin to babble a slew of excuses that seem to do more harm than good. You attempt to express how uncomfortable her offer would make her parents and she demands to know why. She insists that only a guilty old lecher would be too fearful to accept and as long as your intentions are pure, you have nothing to worry about. Unable to free yourself from the hole youve dug, you sheepishly follow her to her room. As your niece urges you to undress for bed, your sister and brother-in-law arrive home earlier than expected. Your heart sinks into your stomach but youre trappedthe risk of getting caught leaving their daughters room is too great. Seemingly delighted by the added risk, your niece confesses shes completely infatuated with you. She lifts her nightshirt to reveal her bare cunt and urges you to use her little body however you desire. Utterly helpless and no longer able to ignore your carnal instincts, you climb into bed and surrender yourself to her.
Genre: brother sister, Cheating, Family, Home Wrecker, homewrecking, POV, Role Play, sister, sisters, Taboo, Virtual Sex, Olive Wood
Video Description: Your sister is delighted when you decide to visit for the weekend and leave your wife at home. Although your motives are innocent, Sis assumes youve arranged a solo visit so that the two of you can rekindle the relationship you had growing up. As you prepare for bed, she loiters by your side and waits for you to make a move. She reminds you that as your hostess for the weekend, shes happy to spoil you and give you ANYTHING you want. When you politely refuse special treatment, she removes her robe and begs you to use her body like you once did. You panic and ask her to get dressed, but she sweet talks you into giving her a little kiss like you used to do. She pulls you closer and slips her hand down your pants, begging you to let her taste your cock. You cant refuse her, and she gives you a slow, seductive blowjob while stroking her eager pussy. When she lies on the bed and spreads her legs for you, you dont hesitate to give her just what she wants and thrust yourself inside her raw. She feels SO much better than your wife but you know you should pull out. Sis will hear none of it and enjoys multiple orgasms on your cock before begging you to finish inside her. If your wife cant give you a baby, maybe she will.
Genre: Bukkake, Family, Role Play, sister, Sisters, Taboo, Virtual Sex, Olive Wood
Video Description: Its the last day of your parents vacation and your sister is desperate to spend the the day with you. When you explain you have other plans, your sister spins a tall tale that brings the two of you closer together than youve ever been.
Genre: Family, GFE, Girlfriend Experience, MILF, Missionary, POV, reluctant, Role Play, sneaky wife, Virtual Sex, Olive Wood
Video Description: Youre staying with your wifes parents in the bedroom she grew up in. Despite her parents being on the other side of a thin wall, you cant help but paw at her until she can no longer resist you.
Genre: Cougar, MILF, mommy, Older Woman Younger Man, POV, POV Sex, Role Play, Taboo, Teacher, Therapist, Virtual Sex, Olive Wood
Video Description: Its your last week of high school and your guidance counselor has a special, secret gift for her favorite student.
Genre: Cheating, daddy daughter, Daddy Roleplay, Daddys Girl, daughter, Family, Home Wrecker, POV, Role Play, Taboo, Virtual Sex, Olive Wood
Video Description: Your daughter hasnt visited much since you moved in with your new wife, but given your scandalous former fling, its probably for the best. When she spontaneously arrives in town you put on a brave face and assure yourself you wont give into temptation, but its fruitless.As you get her settled in on your sofa, she congratulates you on your wholesome, age appropriate wife. She assures you she has no hard feelings for your new partner, but shes surprised by your choice given your proclivity for dating younger women. She begins to reminisce about your past together, but trails off when she notices your discomfort and suggests you head to bed. All she needs from you is a little kiss on the forehead to help her sleep. You hesitate and she takes your reluctance as a sign that youd prefer a REAL kiss. Before you can object, she wraps herself around you and presses her lips to yours. One thing leads to another and you find yourself with your cock down her throat. She promises you your wife wont find out if you take things further and lies down on the sofa, spreading her legs and guiding you inside her. Your anxiety heightens as she repeatedly forgets her promise to be quiet and loudly moans for you, but you dont want to stop. It takes every bit of willpower you can muster not to cum inside her, but when she bends over and offers you her ass, all bets are off. She feels so good you cant help but explode inside her. Your post-orgasm clarity tells you to hide the evidence of your affair as quickly as possible, but she isnt finished with you yet. She insists you watch her as she writhes around on the sofa and makes herself cum for you. She finishes herself off and throws a blanket over body with moments to spare as your wife stumbles into the living room and asks you what youre doing. Your daughter smirks as she wishes you both goodnight, and you head back to bed with your unsuspecting wife.
Genre: Boss Employee, Face Sitting, POV, Role Play, Smell Fetish, Virtual Sex, Olive Wood
Video Description: Olive cant seem to get a break. After losing her job at a high profile law firm and being dumped by her fiance, she finds herself facing dire financial crisis. With no one else to turn to, she reluctantly calls her lecherous former boss and offers her services in exchange for cash. Olive soon finds herself ushering him into her home. It feels odd to have such a bulky, pompous man standing in her effeminate little bedroom and even odder to be standing half naked in front of her former boss. Olive expects to lie back and take him inside her, but to her surprise, he demands that she sit on his face. He admits to having sniffed her chair every night after shed left the office, and wants nothing more than to inhale her essence fresh from the source. Olive does as he asks, alternating between wrapping her thighs around his face and pushing her backside into his nose. When hes had his fill, he instructs her to rub herself on a pillow until its soaked with her juices and hold it over his face as she rides him to completion.
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