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You and stepmom spent all day at the pool. She had a great time— you two never get to hang out anymore! It's late so you say goodnight to each other. Stepmom starts changing out of her wet swimsuit without realizing you're clearly filming her without her knowledge. While she's peeling off the swimsuit, you see she has a butt plug inserted! She stands naked for a bit looking at her body in the mirror when she sees you and frantically tries to cover her body. She orders you to get out and wait for her in your room; She'll talk to you after she gets dressed. Stepmom comes into your room to listen to your apology. You couldn't help it. You're really turned on from playing around in the pool and you haven't been able to hang out with girls since this virus thing started. She's surprisingly understanding, but says she wants you to realize what a this was. She'll forgive you if you promise to spend the evening playing games...AND you have to undress in front of her right now while she takes pics so you can understand what she went through. You're reluctant, but she points out that she should really tell your step-father about this, so you comply. You strip nude as she takes pictures from multiple angles while you protest. She's trying to hide how attractive she finds you, but she's not doing a very good job.

After a bit, she has you put your swimming suit back on (nothing else), and tells you what game you ’re going to play. It’s called “ I ’ll Bet You Won ’ t ” which is like Truth or Dare with higher stakes. One person says “ I ’ll bet you won ’ t ” and the other person has to do it. The first person to refuse loses...and the loser has to be the winner’s personal sl*ve for a month! The game works because you each have nude images of the other, so if the loser doesn’ t agree to be a servant, the winner will send the pics to everyone.

The game starts with simple questions and dares. - Stepmom says " I bet you won ’ t tell me if you snuck out last week to hang out with the guys" (yes) - You say you bet she won ’ t tell you if she was from sneaking at the pool (yes) - Stepmom asks if YOU were a l*ttle from sneaking at the pool (yes!) - You say you bet she won ’ t explain what was in her *ss when she was changing earlier. (She explains what a butt plug is and why she likes wearing it—also says that when you were playing around in the pool she could feel you pressing up against her *ss and it seemed like you was aroused) - Stepmom asks if you liked looking at her *ss (yes) - You ask if she was flattered you spied on her (coyly...yes) - Stepmom sees lights coming down the street and says she bets you won ’ t moon the neighbors from the window (you do)—she comments that she never noticed that small mole on your *ss before. - You say you bet she won ’ t show YOU a mole—she does, showing you two—a mole below her left breast and a mole at the top of her *ss cr*ck. - Stepmom says she bets you won ’ t kiss her for 10 seconds on the mouth (French kiss) - She comments on you looking aroused, so you say, " I bet you can’ t make me c*m...twice in a row!" (Anybody can make a y*ung guy c*m twice) But with no touching! She’s reluctant and you think you've won, but then she strips down and begins gently talking dirty to you. She even takes out a dildo and f*cks herself while looking at you, encouraging JOI. You c*m pretty fast. She then starts encouraging you again, only this time, it’s all about her *ss—she's seen you staring, how you want her to spread it, how much she wants you to f*ck her *ss—she even does some *ss play with the dildo. You c*m everywhere. Stepmom is aroused and it’s her turn: She wants you to insert the butt plug. You refuse and she wins! Her first order for you as her sl*ve? To insert the butt plug. You say no, so she sends a naked pic of you to your cousin as a warning. You comply and slowly insert it as she takes pics. Then she orders you to go down on her. You thought a sl*ve meant doing the dishes! She says that’s not the case, and now, if you don't go down on her and do a good job, she’s going to send the butt plug pic to your crush. You eat her out as she talks dirty to you. She has you l*ck her *ss too, and every time you don't go deep enough, she reaches down and pushes on your butt plug. Stepmom is super turned on. Next she makes you turn over and stick your *ss in the air. She explains that she’s going to use the dildo she used on herself on YOU. It’s not an angry thing—she’s genuinely turned on. She tells you it’s a six-inch dildo, and she slowly inserts it with you breathing heavily and occasionally crying out. She assures you it’s okay, you can take it. She can tell you're aroused. When it’s six inches in, she tells you she has a confession: She shows you the dildo that was supposed to be in your *ss. She lied—it’s actually a 12-inch dildo she's pushing into your *ss. She still has another six inches to go! Stepmom loves the terrified look on your face when you realize how much is left. She inserts the giant dildo the rest of the way and f*cks you with it. She talks about what a dirty boy you are. You c*m hard. She removes the dildo but puts the butt plug back in—you're napping with her tonight, and she's doing what she wants with your *ss tonight too. Fulfills Your Fantasy For: MILF, Taboo, POV, Older Woman, Mommas Boy, Dirty Talk, Embarrassed Naked Female, Confessions, Strip Tease, Bl*ckmail Fantasy, Dildo F*cking, *nal Dildo F*cking, Virtual P*ssy Eating, Instructional, Female Masturbation, *rgasm, Prostate Massage, *rgasm

I Bet You Won't - High Stakes With stepMom (mov)