Olive Wood - Mommy Follows the Doctor's Orders [FullHD 1080P]

Video Description: At your last checkup, your doctor prescribed a very special penis treatment. You’re a little bit embarrassed about what it entails, but Mommy takes your health seriously and won’t let you skip a single session. You know you should be mortified by your own Mommy helping you with such an intimate procedure, but it’s undeniably pretty exciting to watch her lovingly caress your exposed penis as she guides you to your daily “release”. Maybe going to the doctor isn’t so bad after all…

Olive Wood - Mommy Takes Care of You Down There [FullHD 1080P]

Video Description: Mommy loves the comfort and intimacy of skin-to-skin contact with her special boy. Though you're self-conscious about the way her naked body makes you feel, she gently reminds you there's nothing wrong with a healthy erection. Would you like her to take care of it for you?

Olive Wood - Mommy Leaves step-Sister in Charge [FullHD 1080P]

Video Description: You’ve always been Mommy’s little baby. When she heads out of town for a week, she leaves you in the care of your (slightly) older step-sister, Olive, and begs her to keep you safe. Mommy delivers Olive a brief lecture about responsibility, emphasizing that under no circumstances is she to invite any boys over.
The moment Mommy shuts the door behind her, Olive swoops in and suggests the two of you plan something reckless. You staunchly refuse to do anything dangerous, but Olive reminds you that she’s in charge, so you must obey her. She lights up and asks you to relay what the two of you did last time Mommy left you alone. You begin to blush and pretend you can’t remember, but she orders you to say it aloud. As you begin to nervously stutter about how the two of you had sex, Olive insists you unzip your pants and expose your cock. She demands that you stroke yourself to her and explains that since Mommy won’t let her have her boyfriend over, you’ll have to entertain her instead. Once she’s satisfied with your state of arousal, she instructs you to lie on the sofa and prepare to be used.
Olive climbs on top of you and begins to tease your cock with her hands and mouth. She rubs herself with the tip of your cock before sliding it all the way inside her, praising you for your ability to properly fill a woman and admitting that she may have a *slight* thing for sibling sex. Olive rides you until she climaxes several times, alternating between multiple positions to give you the best show imaginable. She reminds you that her own pleasure is paramount, and you’ll be in big trouble of you finish before she’s had her fill. Your mind begins to melt as you try to contain your orgasm, but somehow you manage to make it past the finish line. After what seems like an eternity, Olive comes one last time before rewarding you by letting you finish inside her. You doubt you would have made it another minute if she’d kept going, but you accept her high praise of your stamina and eagerly agree to prepare yourself for another round tomorrow.

Olive Wood - Family Movie Night [4K 1440P]

Video Description: It’s time for your filthy weekly ritual with Mommy. Let’s hope Daddy doesn’t wake up...

Olive Wood - Finally Married Mommy 2 [FullHD 1080P]

Video Description: You love being married to Mommy. The two of you are more in love than ever and certain the honeymoon phase will never end, but there’s one thing step-Mommy can’t get off her mind. Now that you’re a married couple, it’s time to start growing your family, and she’s DESPERATE to begin. She’s not as young as she was when she had you and you don’t have a moment (or a load of semen) to waste...

Olive Wood - Alone with step-Mommy [FullHD 1080P]

Video Description: You’re alone with Mommy, miles from home in a town where no one recognizes either of you. Free from any interruptions or the risk of being caught, you can finally enjoy each other in all the ways you’ve always wanted to try...

Olive Wood - Mommy Plays Favorites [FullHD 1080P]

Video Description: When Mommy finds out you don't think you're her favorite boy, she does EVERYTHING she can to prove her devotion. Mommy doesn't just love you, she's OBSESSED with you.

Olive Wood - Sister in Captivity [FullHD 1080P]

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)