Olive Wood

Olive Wood – Sis Needs You to Help Mommy

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Olive Wood - Sis Needs You to Help Mommy

Olive Wood – Sis Needs You to Help Mommy

Your sister is worried about Mommy. Although it’s hard to keep track of her dating life, your 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.
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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 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 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.
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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.
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You leave Mommy’s room and suddenly remember the deal you made with your 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.

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Olive Wood – Sister Won’t Let You Go

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Olive Wood - Sister Won't Let You Go

Olive Wood – Sister Won’t Let You Go

Concerned that your clingy sister may be holding you back, your parents arrange for you to head to school out of state while she stays behind and attends the local community college. Devastated by what she considers a heartbreaking betrayal, she throws herself at you and insists that your parents only want to separate you because they know you once had sex. She gropes you and begins to unbutton her sweater, announcing that no matter where you go, she’ll follow. Taking your cock into her mouth, she promises you that her body belongs to you alone and that if you take her with you, she’ll be your personal toy. Will you accept her offer?

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Olive Wood – Unexpected Evening with Your Daughter and Your Girlfriend

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Olive Wood - Unexpected Evening with Your Daughter and Your Girlfriend

Olive Wood – Unexpected Evening with Your Daughter and Your Girlfriend

Concerned that your clingy sister may be holding you back, your parents arrange for you to head to school out of state while she stays behind and attends the local community college. Devastated by what she considers a heartbreaking betrayal, she throws herself at you and insists that your parents only want to separate you because they know you once had sex. She gropes you and begins to unbutton her sweater, announcing that no matter where you go, she’ll follow. Taking your cock into her mouth, she promises you that her body belongs to you alone and that if you take her with you, she’ll be your personal toy. Will you accept her offer?

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Olive Wood – WARNING THIS SIMPLE TRICK MAY CAUSE YOUR SISTER TO WANT SEX

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Olive Wood - WARNING THIS SIMPLE TRICK MAY CAUSE YOUR SISTER TO WANT SEX

Olive Wood – WARNING THIS SIMPLE TRICK MAY CAUSE YOUR SISTER TO WANT SEX

With your sister’s help, you discover the secret to growing your penis three times its natural size. Although the experiment begins innocently, she soon discovers she can’t control herself around your massive member and begs you to test it inside her body.

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Olive Wood – Where in the World is Mommy

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Olive Wood - Where in the World is Mommy

Olive Wood – Where in the World is Mommy

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.
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As you’ve gotten older, you’ve become fixated on the idea of finding your mother. Despite Sister’s pleas to leave the matter alone, you’ve secretly spent hours searching for answers and feel you’re getting close to a breakthrough. Sis catches you skimming through records in your bedroom and does her best to distract you, briefly putting all thoughts of Mommy out of your mind as you enjoy an intimate brother/sister date night.
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Sis heads to bed happy, but your thoughts wander to your mother again and you find yourself unable to sIeep. You stroll into the kitchen and begin combing through a stack of junk mail on the counter. You find nothing of interest until you reach a letter you’d missed days before. Your home town’s county clerk has finally granted your request to unseal your mother’s name change record. The woman formerly known as Cherry Wood now goes by OLIVE, your sister’s name. You read on to learn your request for both of your birth records has been denied. According to the county clerk, your sister has never existed. After years of searching, it seems as though Mommy has been with you all along.
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Sis (Mommy?) tiptoes into the living room and urges you to come back to bed. Upon seeing you distraught, she offers you her body to help clear your mind. You recoil at her advances and confront her about your findings. Although she tries to deflect, she’s left with no choice but to admit her true identity. She begs for your sympathy as she confesses to abandoning you as a young mother. She explains that after several years of sowing her wild oats she returned for you, but she couldn’t face the thought of being labeled a neglectful mother and spun a fanciful story to paint herself in an innocent light. She changed her name to Olive and sold the court a phony story about a stalker in order to have the record removed from public access before taking on the identity of your caring, selfless sister.
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Mommy begins to weep and demands pity. She reminds you that today is Mother’s Day, and after all the years of ignoring the holiday, you can finally give her the love she deserves. She throws herself at you and implores you to continue your romantic relationship with her. Blinded by shock and confusion, you give her exactly what she wants.
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Mommy pulls her nightgown down for a special Mother’s Day massage and you soon find yourself with your hand between her thighs. She leans over and urges you to give her your cock and have sex for the first time as mother and son. You oblige, and somehow she feels better than ever. You love being inside Mommy, in fact, you’ve never loved her more than you do right now. The two of you passionately make love on the living room rug and she begs you to finish inside her. Now that the truth is out, it’s about time that the two of you start over once more with a family of your own.

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Olive Wood – Mommy Gives You The Talk

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Olive Wood - Mommy Gives You The Talk

Olive Wood – Mommy Gives You The Talk

You missed countless days of school growing up and somehow managed to slide by without taking a single human biology class. When your older sister announces her first pregnancy, it suddenly occurs to you that you still haven’t the slightest idea how babies are made. Horrified that she may have failed you as a parent, mommy wastes no time in sitting you down to have “the talk”. Although your sex education is over a decade overdue, Mommy’s hands-on parenting style has you covering all the bases in no time.
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(This fabulously educational video contains all sorts of sexy little trigger words you’re sure to love)

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Olive Wood – Mommy Knows What You Did

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Olive Wood - Mommy Knows What You Did

Olive Wood – Mommy Knows What You Did

You’ve really done it this time, Son.
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Olive plays your mother. She talks to you in private about what you did and confronts you with pictures you have taken of her while she was sleeping. Now she will punish you with her strapon and pegging.

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Olive Wood – Pillow Talk and Poor Decisions

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Olive Wood - Pillow Talk and Poor Decisions

Olive Wood – Pillow Talk and Poor Decisions

Sorry, I didn’t mean to wake you. I’ve just been having these vivid fantasies. Do you think…do you think you’d want to cum inside me? Make me a mother? It feels so naughty, doesn’t it? But there’s nothing hotter, nothing more natural than leaving your mark on me forever.

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