Olive Wood

Mommy gets more than she bargains for when she caves in to a late night craving

Based on a true story. VIEWER DISCRETION ADVISED.

Mommy feels hurt when you announce that you’ll be spending the holidays with your father and new stepmom. Jealous and horrified by the thought of being alone on Christmas, she does her very best to persuade you to stay behind with her.

When Mommy finds out you’ve been writing stories about her and uploading them to an erotic literature site, she makes a shocking confession—She’s been writing them too!

When your concerned therapist feels your sessions are no longer productive, she decides to refer you to a mysterious specialist known for her unorthodox, immersive treatments. Unsure of what to expect, you agree to a 48-hour appointment during which you establish a unique mother/son relationship. Who needs traditional therapy when you have a devoted Mommy to take care of you?

Mommy knows about the secret crush you have on your sister. Jealous and determined to be the most desirable woman in the house, she calls you both in for a family talk and explains that it’s time for your sex education. Mommy begins by letting you both suck her breasts before casting your sister aside and focusing on you. She reminds you that no other woman, including your sister, holds a candle to her and that mothers and sons are the perfect match. Enormously aroused by the feeling of your tongue on her breast, she bends over and instructs you to lose your virginity to her. You love the way Mommy feels from behind and the fact that your sister is watching makes it even more thrilling. Mommy pushes you down on a chair and climbs on top of you. As she begins to ride you, she beckons your sister over for a sloppy kiss before using your cock to achieve an explosive orgasm. She encourages you to finish inside her, congratulating you when you finish and suggesting that perhaps next time you can try your sister, but ONLY with Mommy’s consent.

*Warning. Contains taboo trigger words!*

Mommy is getting ready for a date when she spots you slumped in the corner of her bedroom looking ill. Although she’s already running late, she hurriedly rummages around for a thermometer and asks you to be a good boy and open up your mouth so she can take your temperature. After several failed attempts to get an accurate oral reading, she sighs and instructs you to remove your pants so she can insert it rectally. You protest, but Mommy assures you that it won’t hurt and that she’ll be careful with her delicate boy.

You lie down on the bed and obediently expose your anus for Mommy as she gently wets the thermometer in her mouth and prepares you slip it inside you. She counts to three and slowly inserts it. You attempt to remain calm, but to your embarrassment, you start to feel yourself getting an erection. Mommy laughs and ensures you that it’s nothing to be embarrassed about and that plenty of men enjoy anal stimulation. She anxiously checks the time before concluding that despite being late for her date, it would be wrong to leave you home alone with a fever and an uncomfortable erection. In order to absolve herself of the guilt she feels about leaving you, she offers to help you explore your newfound interest in anal stimulation. She slips one of her fingers inside you and begins to stroke your cock and tongue your tight hole. As you grow more and more excited, she adds another finger and brings you close to orgasm, stopping before climax to offer you her own body.

Mommy lies back and removes her dress, instructing you to mount her and push yourself inside her. Mommy has never looked more beautiful than she does as she looks up at you in ecstasy, her succulent breasts bouncing up and down with every thrust. Mommy orgasms and tightly wraps her legs around you, pulling you closer and begging you to finish inside her before it’s time for her to leave. You dutifully do as she says and fill her with your cum, secretly delighted by the idea that she will soon be out with another man who has no idea what you’ve just done.

You’re used to your special afternoon playtime with Mommy. When she explains that today’s session will have to wait because your grandparents are downstairs, you refuse to take “no” for an answer and insist that your cock absolutely must be milked. Although she’s terrified of what may happen if her parents find out what she likes to do with their grandson, Mommy gives in and nervously offers to suck and ride you until you finish inside her. You’d better hurry so you don’t get caught!