Tag: Olive Wood

Olive Wood – Trained and Feminized by Mommy

Mommy knows your secret! You’re horrified when she confronts you about your obsession with massive cocks and the oversized dildo she found under your bed, but Mommy is understanding. She knows that the only way to help you is to fully feminize you, lock you in chastity, and train you to please masculine, superior men like the good little slut you are.

Olive Wood – Practice With Mommy

Mommy has explained the birds and the bees countless times to you, but when it comes time for your first big date, you still feel woefully unprepared.You rush to Mommy to ask for last minute advice and in your haste, you embarrassingly overshare. You explain that when you masturbate, you can’t last very long, and then the words spill out of your mouth before you can stop them—whenever you masturbate, it’s thoughts of HER that send you over the edge.

Olive Wood – Mommy Should Be Your First

You burst into Mommy’s room after an abysmal movie date and are comforted to see she’s waited up for you. Mommy prompts you to fill her in on your evening, and you tearfully admit to your date walking out on you halfway through the movie. You’re concerned you may have offended her by trying to kiss her and ask Mommy if you’re a bad person or a clumsy kisser. Mommy assures you you did nothing wrong, but just to be on the safe side, she suggests you demonstrate the kiss you gave your date. Mommy needs multiple kisses in order to properly assess your skill level, and determines you’re in dire need of coaching. The two of you kiss until she’s satisfied with your progress, but somehow neither of you feel satisfied. In order for this lesson to truly be a success, Mommy decides she ought to teach you how to properly handle breasts. As you fondle Mommy, she can’t seem to take her eyes off your obvious erection. She sighs and admits that if she wasn’t your mother, your cock would already be in her hands. She closes her eyes and pretends for a moment that you’re unrelated, but neither of you can hold it together for long. Soon, Mommy finds herself unzipping your pants and can’t seem to stop herself from leaning over to taste you. Mommy gently teases you with her mouth, but it isn’t enough for her. While she has you in her bed, she might as well take your intimacy lesson to the next level.

Olive Wood – Mommy Never Leaves the House

You arrive for a weekend cat sitting gig. The chatty brunette who greets you checks your ID and excitedly tells you that you have the same name as the original owner of the property. Your parents have never told you much about your family history, but you’re fairly certain you’ve never had relatives in the area. The brunette gleefully goes on to gossip about the home’s history, suggesting that it was once occupied by a mother and son who were very, very close. According to some, the pair had a secret son, but no one knows what happened to him.

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.