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Olive Wood - The Secret Inside Me

Sun 21 Jun 2026 21:06:00 +0200

You come home to find stepMommy heartbroken. She's just learned that step-Daddy has canceled his business trip and decided to take the next few weeks off so he can be present when she goes into labor. stepMommy HATES that step-Daddy plans to intrude upon your cherished time together. You're the one who put your seed inside of stepMommy and you're the only one she wants by her side during the birth. stepMommy also hates the thought of step-Daddy ruining your chances to be intimate with each other during the final week of her pregnancy. She's insatiably horny and wants nothing more than alone time with YOU. You promise stepMommy everything will be okay and remind her that there's still time to have sex before step-Daddy gets home. Seeing your beautiful cock seems to melt her troubles away. stepMommy gives you a passionate blowjob before spreading her legs and begging you to fill her pregnant body. You're more than happy to oblige and push yourself inside stepMommy as she praises you for being such a perfect lover. As you feel your orgasm mounting, stepMommy decides she wants to ride you. She climbs on top of you with her round belly and engorged breasts on full display as she squirts milk and wildly grinds on your cock. Seeing stepMommy bouncing up and down with your little creation inside her drives you wild. You wish you could impregnate her over and over and imagine using her as your breeding slave as finally climax inside her. stepMommy feels MUCH better now and your remedy came just in time! As stepMommy climbs off of you, step-Daddy walks in and nearly catches you! You'll have to be more careful next time...

Olive Wood - Don't Trust Your Homewrecking Aunt

Sat 20 Jun 2026 19:57:00 +0200

You’ve been unexpectedly declared the heir to your family’s substantial fortune. When you and your wife throw a party to celebrate, your bitter, frigid, Aunt pays you an unexpected visit. Although she’s not so frigid anymore…in fact, you’ve never seen her act this friendly with anyone before.

Olive Wood – Nights with Mommy

Thu 11 Jun 2026 05:15:08 +0200

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Nighttime with Mommy is the best. She always lets you stay in her bed, pressed tightly against her, skin-on-skin. With her body so close to yours, it’s not unusual for you to wake up with an erection. She doesn’t mind, though. Mommy knows it’s normal for boys your age to get hard, and she’s always happy to help. No matter what time of night it is, she ALWAYS wants you to wake her up and use her body to your liking. That’s what mommies are for.

Olive Wood - Smoking Hot stepMommy Needs Your Seed

Wed 03 Jun 2026 17:15:06 +0200

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

Olive Wood - Only For Daddy

Sat 30 May 2026 23:00:07 +0200

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Your wife has told your stepdaughter that her dress is too revealing to wear out. You agree that it's revealing, but it's not too revealing to wear around YOU! Some things are best kept between the two of you, and her risqué little outfit is no exception.

Originally a custom video, but no names are used.

Olive Wood - Aunt Blackmailed into Weird Potty Training Roleplay

Fri 29 May 2026 23:18:05 +0200

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You’ve been blackmailing Aunt Olive for months. After convincing your parents you (a fully grown adult) STILL need a sitter while they’re out of town, Aunt Olive has been coming over to watch you. You’ve put her in all sorts of uncomfortable situations, but this weekend you’ve decided to try something new—potty training role play. Auntie Olive is horrified when she learns she’ll be responsible for “potty training” you, but she has no choice but to comply. All weekend long, Aunt Olive dutifully sits in the bathroom with you when you need to go. Since you’re only just “learning”, accidents happen, and things might get little messy…oops.

Olive Wood - We’re Not a Normal Family

Fri 29 May 2026 23:06:07 +0200

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Desperate to keep your sister from returning home to her wife, you have no choice but to show her the video you have of her having sex with your dad! You agree to delete it IF she gives you the same treatment, and it doesn’t take much convincing. The two of you have always felt you might end up in bed together, and now you both have the perfect excuse. sis pushes you down onto the mattress and thrusts her tits into your face, ordering you to suck on them as she rides you raw. After using your cock to make herself climax, she returns the favor with an intimate blowjob. You both agree that you’re NOT a normal family, but that’s okay. You wouldn’t have it any other way.

Olive Wood - We're Not a Normal Step-Family

Tue 26 May 2026 16:31:07 +0200

Desperate to keep your step-sister from returning home to her wife, you have no choice but to show her the video you have of her having sex with your step-dad! You agree to delete it IF she gives you the same treatment, and it doesn't take much convincing. The two of you have always felt you might end up in bed together, and now you both have the perfect excuse. Step-sis pushes you down onto the mattress and thrusts her tits into your face, ordering you to suck on them as she rides you raw. After using your cock to make herself climax, she returns the favor with an intimate blowjob. You both agree that you're NOT a normal step-family, but that's okay. You wouldn't have it any other way.

Olive Wood - Only For Step-Daddy

Tue 26 May 2026 16:15:05 +0200

Olive Wood - Let Me Love You

Tue 26 May 2026 15:53:05 +0200

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Your stepdaughter has come home to visit, and you can't help but notice how womanly she's become since you saw her last. She excitedly goes through the clothing you kept for her in her old bedroom and tries on a few dresses for you, showcasing how well she fills them out now. You try to stifle your guilty arousal as she twirls for you and caresses her curves, but it's...hard. As she seemingly teases you, she confesses she's ready to be your LOVER! You attempt to deflect, but when you realize how much it upsets her, you can't help but cave in. She really is your special girl, and it's time to finally admit it to yourself.

Originally a custom video but no names are used.

Olive Wood - THE PURITY BALL (2026)

Tue 26 May 2026 15:52:06 +0200

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In an impulsive attempt to impress your new boss, you decide join his church and RSVP to attend the congregtion’s annual Purity Ball with your stepdaughter. Though you raised her an atheist, she’s supportive of your spiritual journey and agrees to be your wingwoman.

When you arrive at the function, you’re pleasantly surprised to see the female attendees are all adults around your step-daughter’s age. After co-mingling with some of the guests, the two of you begin to suspect things aren’t as they seem. Many of the duos don’t appear to be related, and their relationships seem too intimate to be familial. As the night progresses, the truth is revealed—the “Purity Ball” is really a fetish event! You’re humiliated to have missed the memo and invited your own stepdaughter to a sex party, but she insists the two of you should act cool to avoid making waves. Your boss seems to view you with newfound respect and is finally giving you the attention you feel you deserve. If you walk out early, you may burn bridges and lose the one chance you have to advance yourself professionally.

Your boss seems especially enchanted with your step-daughter, so she suggests you might seem more “impressive” to him if she plays the role of your dedicated lover. The role play begins benignly, but as the party guests’ behavior grows lewder around you, the only way to fit in is to follow their lead. Your stepdaughter gets on her knees and begins slowly sucking your cock. Though initially uncomfortable, your boss’s approving glances in your direction dissolve your apprehension. She strips off her dress and offers you her body. No one here knows she’s your real stepdaughter, so you might as well put on a show. She lies back and pulls your cock inside her. Having taboo sex in a crowded room feels utterly surreal, but better than you want to admit. She erupts in explosive orgasm before bending over for you and demanding you take her from behind. She loves feeling exposed with her own step-daddy penetrating her. Though you’ve never considered yourself an exhibitionist, the sheer depravity of the act excites you too, and you finish INSIDE her. Though you should feel guilty, you’re full of too much adrenaline to fully digest the situation. Your boss now respects you, you’re closer to your stepdaughter than ever, and you finally feel as though you’re part of a community. Though you know what you’ve done is wrong, it feels too good to turn back now.

Olive Wood - Mommy Can Fix You

Sun 24 May 2026 01:55:09 +0200

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MOMMY has always hated your wife. When your weekend solo visit concludes and you pack up to spend the rest of the holidays with your in-laws, Mommy stops you at the door and insists you remain with her. She knows your wife will never love you like she does and without her diligent care, you’re a very sick boy. You promise her you can handle yourself but she won’t listen. She orders you to drop your pants so she can examine your penis and determine for herself whether its getting the special attention it deserves. You obediently pull your pants down for her and her suspicions are confirmed—your penis needs care ASAP!

Mommy rushes you into the bedroom you grew up in and tucks you into bed where you will remain until your treatment is concluded. She warns you that the road to recovery will be arduous. In your dire condition, the only way to save you is to drain as much semen as your body can produce. No matter how sore or tired you become, she plans to bring you to climax repeatedly until all the negative energy has left your body. It may take days or weeks, but she WILL fix you.

Originally a custom vid but no names are used.