Well what do I have here? Did you have to take some time to yourself away from your aunts pool party? Why could that be? Is it because you couldn’t keep your eyes off of me still… after all of these years? I saw you slip away… what state you were in. Honey, I am going to teach you what to do about that.
Your best friend’s Mom runs into you right after your workout in the home gym and offers you a protein shake and some muscle building advice. She thinks you look great, so grown up and asks if you can help her move a heavy package. Afterward she wants to give you a tip but says she will have to give you a kiss instead since she doesn’t have any cash right now. She is definitely flirting and asks you not to tell her son and says you’re her favorite boy in the neighborhood. She goes right down to give you another kiss – on your penis! She says it’s a french kiss but you know what’s happening – she’s gonna blow you – and she does. This leads into her on top, doggystyle, sitting and cumming on your face, and a missionary/cowgirl cum inside. Shhhh Don’t tell our secret Thank you for getting this taboo cougar first time MILF roleplay fantasy film. Thank you!
You are innocent, cute and you have your first erection in my class! What am I to do? Luckily for you, I am a very hands-on teacher and used to dance to pay the University, so I give you a lapdance to help you cum, which you do, but you are still hard! and I cannot let you walk the hallway like that, so I give you an oral you will like for once and then ride you until you cum again and your -not so little- problem gets resolved.
Your new work buddies talked you in to coming out for your 18th birthday. You thought maybe you’d go to the sports bar down the street and get some wings, maybe someone would have a fake ID you could use or something, but instead? They take you to the strip joint downtown, have you pick out a dancer, and they get you a champagne room. You gravitate to this one woman, older, more mature, curvy, sexy. When she takes you back, she seems into how young you are. She teases about the sparkling cider they sent for your time together, although you can’t imagine guys open it even when it’s the real stuff. Not when she’s there, rubbing on you, making your dick harder and harder…and, you don’t think she’s supposed to do this, but…she can’t help but reach into your pants. She keeps talking about how big you feel, how its huge, how she’s never felt a guy get this big and hard…before you know it, your monster cock is pressing into her mouth while she worships your enormous dick right there in the champagne room!
You and Step-Mom have been flirting with Taboo play ever since she saw your erection and when Step-Mom asks you what you’d like to do tonight she is not that surprised at your answer. You tell Step-Mom that you want to FUCK and CLAIM her PUSSY as yours tonight! She tells you that she can’t, it’s … taboo … You continue to convince her why she should be the first to feel your stiff cock and you guilt her with the, “Don’t you love me Step-Mom” line. Step-Mom decides that if you’re going to claim her pussy that you need to be trained to do what she wants and how she likes it! Step-Mom teaches you to fuck her better than any man. She tells you to smell and taste it, fuck it from the back, and she rides you until she demands you to cum inside.
You did what she told you to do. You pushed him and bullied him and humiliated him until he just couldn’t take it anymore. Finally, he snapped and punched you in the face. You had to admit, it hurt. Everyone saw it too. They all cheered and clapped when his fist connected with your face because you deserved it. But it hurt a lot less knowing you’d get to fuck his hot mom.
You knew it was coming. The consequences of your actions. You never should have hit him that hard. You even felt a little guilty about it. But bullying him was just a regular every day thing now and it was hard to stop, even if sometimes you wanted to. Then his mom walked in. You knew you were gonna get an earful. But she doesn’t want you to stop. She wants you to keep going. And she’ll make it worth your while.
Becky’s jealous step-son, Jay, catches her laying by the pool taking sexy selfies and he is not happy about it. When she comes inside he confronts her about it. He doesn’t understand why she needs to take pictures of herself looking like a whore. Becky gets very offended and tells him that she is a grown woman and she can do whatever she wants. Jay disagrees and shows her that only he is in charge of her body.
Becky is on the phone with her girlfriend excitedly talking about the barbecue later that day when Jay comes in and takes the phone from her. She can’t believe how rude he is but he doesn’t care. He wants to know where the hell she thinks she’s going in those daisy dukes and skimpy tank top. She tells him, but he’s not having it. Instead, he yanks her clothes off, fucks her and fills her mouth with cum.
TABOO, MILF, SWIMSUIT, BIG TITS, OLDER WOMAN / YOUNGER MAN, COUGAR
COUGAR, DUEL MASTURBATION, MILF, OLDER WOMAN / YOUNGER MAN, POV, TABOO
You get home to find out the principle already called Step-Mom and told her you tried looking up the teachers skirt. Step-Mom checked your room and pc and knows all your dirty secrets – your search history about MILF’s and her panties under your pillow!!! She tells you repeatedly how you’re a fucking pervert while berating you and she’s also pissed that you are into the teacher instead of her. How dare you flirt with that bitch – do you know how much trouble we could get in? No more dirty boy at school You have to start cumming before school every day with a proper dirty MILF – Your Step-MOM! Step-Mom teases you with dirty taboo talk about you listening to her fuck guys and jerking off outside her bedroom door for years and how now it’s your turn to be a big boy. She teases you about how you listen to her masturbate in your room and has you lick her pussy while she cums in your mouth. Now that this pussy is wet stick it in and CUM FOR Step-MOMMY – YOU FUCKING PERVERT.
MILF, TABOO, COUGAR, DUEL MASTURBATION, POV, OLDER WOMAN / YOUNGER MAN