It’s your senior year and you’re finally coming into your own: more confident, more in shape, and ever since word got out about what you’re packing, you’ve been getting a lot of attention from some of the hottest girls at school. Tonight, it’s Allie, this really hot girl on the tumbling team. Fit, petite, and from what you hear, pretty slutty. Your curfew is 10 and it’s 11:30 now, but you can’t risk missing this opportunity. When you get home, you quietly open your bedroom door to find…your mother, in your bed…and her face…is…buried in your dirty boxers? What the fuck? You try to be quiet but the door clicks behind you and your mother snaps awake, demanding to know where you’ve been. You try to turn it on her, asking why she’s got her face in your dirty boxers but she pretends like it was an accident because you’re so messy. You just hope she doesn’t notice the pair of dirty panties you stole from her hamper, buried under your comforter. You’ve always loved jerking off to her. She starts to lecture you on curfew but then, her tone takes a turn. She mentions the pictures you’ve been sending, and you realize that your cell phone is next to her. Fuck, you left it behind. Your mother went through your phone and found out where you were going…and saw all the photos you’ve been sending. How fucking embarrassing. Even more so is when she tells you how nice your cock is. What?? You’re starting to think there’s more than just your messy habits behind her having her face in your boxers… You try to stay focused but its hard – you can practically see her nipples through her nightie. She’s always been that way, walking around flaunting her breasts and body. Even as she’s tearing into you, you can’t help but stare at her breasts, the way her silk robe falls open to reveal the lace cups of her teddy. She knows. You know. You try to redirect the conversation, back to what she said about your cock. She knows what you’re doing. You know what you want, same as she does. “We can’t do anything about it, you know,” she says, “even if it were true – even if my face was buried in your boxers and I was masturbating to the videos of you jerking off on your phone…even if that were all true, what good would talking about it do? It’s not like we can act on it…right? It’s not like you can take that cock out and stroke it…not like I can lie back and touch myself, watching you stroke…it’s not like you can take that cock and rub it against my pussy, push it inside of me, and finally do what we both want…”

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You’ve been having problems with your Bully at school for a while now and because I felt bad I decided I would rather the Bully punish me instead of you, and he agreed to do it but only if you watched it the whole time. I start out explaining to you that I am going to sacrifice myself to save you the trouble because I know that men just need an outlet for their masculine aggression and I’d rather it be taken out on me than on you. He starts by roughing me up a bit before he collars and leashes me to take complete control. Once the collar is on he moves on to paddling and spanking me as hard as he can while I whimper and cry out, looking at you the entire time. After beating up my holes and ass he brings me to my knees in front of him to give him a rough and sloppy blowjob before he sits down and starts shoving my face into his ass. I’ve never licked a guy’s ass before so this was especially difficult for me but I did it because I want to protect you. He made sure I was really in there by pushing my head down with his hands and sometimes even his feet. After nearly 20 minutes of pleasing him that way he stands up and covers my face in a massive load that is bigger than any cumshot I’ve ever seen, and I mistakenly thought that was the end but he had other plans in mind. As I sit there utterly defeated, he then covers my face and dress in his piss while I hold back tears from being so humiliated. By the end of it I am soaked, bruised, and covered in fluids but it was all worth it to protect you from your Bully.

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You’ve come over to your best friend’s house and his mother greets you and invites you to sit in the kitchen while she cleans up. You’re going with your friend’s family on a weekend getaway, and your friend and his father are out running errands. While your hanging out with your friend’s mom, you can’t help but notice that she’s barely dressed, hard nipples poking through the thin fabric of her robe. After a few minutes of talking her big beautiful breast pops out and you can’t help but notice it. Your friend’s mom notices the bulge rising in your pants and starts asking about your experience with women. She’s actually quite delighted to find out you’re still a virgin, and muses about how much she could teach you. Well, she has a nice surprise for you on the weekend getaway…consisting of lots of closeups of her beautiful big tits, her wet, hairy pussy, and her moans of orgasmic bliss while she lets you cum inside of her! This is a virtual sex tape you aren’t going to want to miss.

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Sweetie, I wanted to talk to you about something… Since I’ve been living with you and your fâther, I noticed no girls ever come over to visit you. Is it safe to assume you don’t have a girlfriend? And that you’re maybe still a virgin? Oh that’s ok darling, you can tell your step-mommy. That’s what I thought, you’ve never had relations with a woman. I would hate you to stress about it and pursue girls, so I’d like to propose you and I enter a special kind of relationship – MOMnogamy. It’s a relationship where you stay my virgin boy forever. You seem apprehensive about it but I can see the erection in your pants, sweetie. Why don’t you just give it a chance, take your cock out, and stroke for step-mommy? You’ll love it, I promise.

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I’m hanging out in my hotel room stuck on a lame vacation with my step-mom. She apparently thinks it’s lame too when she gives up on the pool and comes to hang out with me. I thought she was hoping to have a vacation fling or something but I didn’t know how bad she needs “it” until she starts to tell me all about it

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