Olive Wood - Sis Needs You to Help Mommy [FullHD 1080P]

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.

Olive Wood - Sister in Captivity [FullHD 1080P]

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)

Olive Wood - Where in the World is Mommy 4K [4K 2160P]

Video Description: You have no memories of your mother. Mommy left you with your big sister when you were young and all you’ve ever known is Sis. The two of you have developed a unique bond as she’s grown into the role of your caretaker and more recently, your lover.

Olive Wood - Sex Lessons With Your Aunt [FullHD 1080P]

Video Description: Your aunt has never approved of her sister’s 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.

Olive Wood - The Everlasting Erection [FullHD 1080P]

Video Description: Your witch wife struggles to find an antidote after an erection spell goes awry and lands you with a boner that won’t subside.

Olive Wood - Your Niece is in Love with You [FullHD 1080P]

Video Description: Your sister has invited you to crash on her sofa while you’re 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, you’ve tried your hardest to avoid direct eye contact with her. She’s far too pretty for comfort and letting your guard down in her presence takes your mind to places you’d 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 you’ve 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 you’re trapped—the risk of getting caught leaving their daughter’s room is too great. Seemingly delighted by the added risk, your niece confesses she’s 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.

Olive Wood - Sister Tells A Fib [FullHD 1080P]

Video Description: It’s 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 you’ve ever been.

Olive Wood - Your Wife's Parents Will Hear [4K 1440P]

Video Description: You’re staying with your wife’s parents in the bedroom she grew up in. Despite her parents being on the other side of a thin wall, you can’t help but paw at her until she can no longer resist you.

Olive Wood - School Counselor Says You're Special [FullHD 1080P]

Video Description: It’s your last week of high school and your guidance counselor has a special, secret gift for her favorite student.

Olive Wood - Smoking Hot Mommy Needs Your Seed 4K [4K 2160P]

Video Description: Mommy catches you quietly watching her smoke. Noting your arousal, she decides to seduce you into giving her exactly what she wants.