Tag: OLDER WOMAN / YOUNGER MAN

Fifi Foxx Fantasies – Sydney Paige – A Safe Space inside of Step-Mommy: Her Warm, Comforting Pussy – HD 1080p

Hey sweetheart, I called you in here because I noticed that you were upset. Do you want to tell me what’s wrong, honey? You barely touched your food during dinner…and I even made pie – I know it’s your favorite. You barely had anything to say today…even yesterday you were quiet.
Do you want to talk to me about it? Step-Mommy’s always here for you no matter what – you know that, right? You know it’s just me and you against the world, sweetheart. So, come on, have a seat and talk to Step-Mommy. If you’re having a bad time at school, if your friends are being mean to you, if you’re having other problems…Step-Mommy is here for you. I want you to always know that and always remember it.
So, tell me…what’s been troubling you? School? Friends? Are you just not feeling well? Are you sick? All of those things? I mean, adolescence is tough – I know mine was, so I understand. What can I do for you, sweetie? Um…do you want to maybe play hooky from school tomorrow and go out and do some fun stuff? Would you like that? We can absolutely do that!
We can go out and eat junk food, go to the beach…you don’t have to do your chores today or tomorrow – you can just have fun and not worry. How’s that sound? There’s other things we can do, too. If you’re having problems at school, I can help you with your homework and talk to your teachers. If you’re having problems with your friends, I can navigate you through that. There’s also some emotional and physical things I can do for you, too, sweetheart.
Step-Mommy’s always here for a hug, as silly as that sounds. You are a growing boy, so there are other things that Step-Mommy can do for you that always make a growing boy feel good – do you know what those things are? No? Well, there are some things that can de-stress you, and you know Step-Mommy can be here for that. You can always find a safe space inside of Step-Mommy.
And not just “inside” of Step-Mommy, but…I know you have a computer in your room and a smart phone in your pocket…you know what I mean. Step-Mommy can do things for you to help you release and de-stress. So, besides skipping school and eating junk food and all that, how about I show you how there’s always a safe space in Step-Mommy for you.
I want you to see that there’s a nice, warm space in here for you…so, come on in. Step-Mommy’s always here for you, in any way that you need her. I love you.

TABOO, MOMMAS BOY, OLDER WOMAN / YOUNGER MAN, MILF, VIRTUAL SEX, POV

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Fifi Foxx Fantasies – Reagan Lush – Biological Step-Mother: Step-Son Humiliates & Degrades Step-Mom Who Abandoned Him, POV – HD 1080p

“You have a really nice room here,” Step-Mom smiled, her eyes glancing around the bedroom, “it seems like your parents are taking good care of you. I saw some really cute family pictures in the hallway.”
It was the first time you had met her. She abandoned you when you were just a baby and you were lucky to be adopted by such a wonderful, loving family. “I appreciate you just letting me come talk to you face-to-face,” Step-Mom went on to say. “I know your parents were uncomfortable with me coming and talking to you. I just really want to build a relationship with my step-son…finally, and I’m not expecting you to just open up to me right away.”
Step-Mom wanted another chance. She rambled on about how she was young and stupid when she had you, that she couldn’t even take care of herself. She felt scared and she had no one to help her. She even admitted to having a lot of “partners” during that period of time and wasn’t thinking clearly. “I just needed time to grow up…” she said, “and I mean, look at you, you had plenty of time to grow up…you’re almost a man. They did a really good job raising you.”
Pathetic excuses…all of it. You weren’t going to sit there and listen to her sob story. She abandoned you – your own step-mother abandoned you. “I told you, my head wasn’t there, I wasn’t ready to be a step-mom,” she said desperately in response to your anger. “I am now. I’m sober, I don’t rest around like I used to…and I just want to be a part of your life if you’ll have me.”
She wasn’t your real step-mom. Your real step-mother wouldn’t do something like that to you. That was cold…cruel. “I’m here because I love you and I care about you,” she told you. “I know you’re angry, but you have to give me a chance to make this right. Calling me a slut isn’t going to help anything, you don’t need to yell at me.”
You were furious. This woman…this stranger thought she could suddenly come into your life? “Well, what do you want me to do?” she said out of frustration. “You…what? Listen, I’m your step-mother, you’re not going to talk to me that way. I am not going to strip for you! Calm down! That’s really going to help? Humiliating me? Having me strip down in front of my own step-son?”
You wanted to degrade her, humiliate her – you wanted to make her feel worthless and used. She was nothing to you. You’d grope her, then force her to do awful, sexual things with you. You wanted to make her feel disgusting. She’d beg you to stop, for you to accept her into your life, but she was nothing but a dirty whore. After all, this is what she deserved for abandoning you.

TABOO, OLDER WOMAN / YOUNGER MAN, MILF, VIRTUAL SEX, MOMMAS BOY, POV

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Fifi Foxx Fantasies – Ivy Secret – Step-Mother Shames Perverted, Lewd Step-Son, POV – HD 1080p

It’s just so disgusting…I can’t believe you think about your step-mother in that way. You know it’s wrong to think about me sexually, but you’re still doing it. Is there something wrong with your brain?
Where do you even get off being like that? Do you just sit around and jerk off thinking about me all the time? Do you fantasize about my body and the things you want to do to me? Do you even know how fucked up that is? It’s so gross.
You probably want to touch yourself now, don’t you? You jerk off to me all the time anyways, so why not do it now? You know it’s wrong, but you’re going to do it anyways. You’re going to pull out your cock and start jerking off…right in front of your own step-mother.
You want me to unfasten my robe, don’t you? You really want to see what’s under here? I’m your step-mother, don’t you know it’s fucking wrong? That it’s disgusting? I bet you fantasize about bending me over and shoving your big cock inside my pussy. Do you think about cumming inside of me? About pulling my hair? Do your friends know that you think about that? Do they know you fantasize about your own step-mother sexually? About seeing her naked? About walking in on me while I’m in the shower? Do you think that’s normal?
There’s gotta be something wrong with you. You’re always checking me out and telling me how good I look. At first, I thought you were just complimenting me, but now I see that you’re just a fucking disgusting pervert. How long have you been fantasizing about me, huh? How long have you been imagining touching my body…about grabbing me? How long?
Do you think about what kind of lingerie I’m wearing? I bet you have a specific kind you like, too. I bet you go into my room when I’m not there and you pull them out and rub them against your body, don’t you? Do you smell my panties?
You gonna cum? Keep going. Ah…now how did that feel? Do you feel like a disgusting pervert? You just jerked off in front of your step-mother…

TABOO, OLDER WOMAN / YOUNGER MAN, MOMMAS BOY, MILF, DIRTY TALK, MASTURBATION ENCOURAGEMENT

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Fifi Foxx Fantasies – Carmen Valentina – Step-Son’s Dick Size: Step-Mom Helps Step-Son Feel Better about His Dick, POV – HD 1080p

Oh…hey honey, what are you doing in here? Are you okay? You look kind of frazzled. Wha-what? I’m sure you’re fine, you have nothing to worry about. Don’t worry about other guys’ sizes, every guy brags about their dicks being so big, but most guys have a pretty normal dick – like your step-father’s, he’s average. Yours is probably not small at all. I think you’re just obsessing. Are you watching too much porn where the guys have really insane, big ones? It’s not realistic.
You wanna show me? No, no, I don’t need to see it, don’t show me. Why do you need me to see it? I’m sure everything’s fine, you’re probably average just like the other boys in school.
You’re not going to give up, are you? Okay, I…guess you can show me. I’m just going to give my opinion and that’s it, nothing else. And then you’ll know that there’s nothing to worry about. I guess you can go ahead and take off your pants…are your pants off?
You look average! I mean, it’s kind of limp, so I can’t really tell because some guys are growers, but even your limp dick looks average. Well then, you’re going to have to tug it a few times if you want me to look at it while it’s full erect. Give it a few tugs. I’ll look away to give you your privacy while you do that. There’s nothing to be nervous about, I’m your step-mother. You don’t have to be shy – you’re the one who wanted me to look at it!
It seems like you’re having a hard time…come over here, let Step-Mommy help you. Step-Mommy’s going to help you get it nice and hard, and once I give you my opinion, you can get up out of here with the understanding that your dick isn’t small. Let me know when it’s at full erection. I already feel it getting bigger and harder in my hand.
You don’t have to look at me, I’m not looking at you. It looks normal, it’s definitely not a small penis. You also don’t have a monster penis, which you should be grateful for, because you’d be scaring girls away. Your dick looks just like your step-father’s dick. And I’ve been with your step-father and we obviously had no problem with his dick because you’re here.
You should have no problem with girls. There’s nothing to worry about. In fact, you look a little above average – a lot of girls will like that. But now you have a hard-on. It’s going to hurt if you don’t take care of it, you know? You’re going to have to cum. You want Step-Mommy to take care of it? I can show you how a girl would enjoy someone with your dick size, and meanwhile, we’ll take care of that hard-on, okay?

TABOO, OLDER WOMAN / YOUNGER MAN, MILF, VIRTUAL SEX, MOMMAS BOY, POV

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Princess Ellie Idol – Sis Takes Your V-Card 1080p

I’m back in town for your birthday again and it’s been one year since the events in “Super Risky Blowjob From Sis” took place. You’ve changed a lot in a year, so MUCH of a man now and I can’t help but be super attracted to you. I play it cool though of course and snag your comic out of your hands and lay next to you on the bed. We’re catching up and I ask if you recall last year. Of course, you do, and it’s not long before I’m stroking and sucking on your grown cock. It’s SO big now! As I’m giving you a blowjob we almost get caught, TWICE. We’re informed that we’re to SHARE a room tonight as it’s a full house. I pretend to protest but deep down I’m excited to share a bed with you and take your virginity! When night rolls around, I make sure everyone is in bed before I hop into one with you. Are you ready for sis to take your v-card? Make me cum as you suck my nipples! I’ve been thinking about this all year long, bro!!

TABOO, BLOW JOBS, OLDER WOMAN / YOUNGER MAN, POV, SISTERS, VIRTUAL SEX

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Primal’s MILFS – Dee Williams – Paying off her Son’s Debt 1080p

Dee answers the door and an aggressive young man comes in. He explains that her son owes him ALOT of money and he is there to take everything the boy owns as START of repayment the loanshark even demands her son’s college tuition. Dee realizes her son’s whole future is on the line, so, she tries to make a deal…

MILF, BLACKMAIL FANTASY, OLDER WOMAN / YOUNGER MAN, TABOO, BIG TITS, FEMALE DOMINATION

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Primal’s MILFS – Sarah Jessie – Surrendering to the Repo Man 720p

Sarah can’t believe she walked outside to find her son’s car about to be repod. She’s kll him if he wasn’t at his dad’s for weekend. She tries to reason with the repo man, but he isn’t hearing it, he needs to collect something or the car is gone. She isn’t prepared for what he demands, but she doesn’t see a choice. She is ashamed but a little flattered that he thinks she looks good enough to want what he wants. She goes a lot farther than she wanted, but she never told him to stop even when he was rougher with her than she expected. And all she bought was a some time to come up with months of missed payments.
Sarah is coming out of the shower and is surprised by the repo man waiting in her bedroom. He is there to collect again, and this time he demands more than before. He uses Sarah every way he wants before he is done.

MILF, BLACKMAIL FANTASY, OLDER WOMAN / YOUNGER MAN, BIG TITS, BLONDES, TABOO

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Primal’s MILFS – Makayla Cox – Blackmailing your Friend’s Mom 720p

Makayla’s son’s friend Ricky shows up unexpectedly and when Makayla answers the door he just walks in. Makayly is more than a little annoyed, but when Ricky confronts her that he knows she has been having an affair with the neighbor she starts to panic. Ricky doesn’t want to ruin her life though, he just wants to know what it is like to be with a MILF

FEMALE TRAINING, POV, OLDER WOMAN / YOUNGER MAN, BABYSITTER, AGE REGRESSION

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Primal’s MILFS – Eva Long – Taken by the Boy Next Door 720p

Eva has no idea the boy next door knows the code to her door, has been sneaking in while she is napping, even watching her while she is awake. Finally the boy makes his presence known. Eva is filled equally with fear and arousal

MILF, SLUT TRAINING, BLACKMAIL FANTASY, OLDER WOMAN / YOUNGER MAN, DOMINATION, TATTOOS & PIERCINGS

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Primal’s MILFS – Ariella Ferrera – Bitchy boss Blackmailed by the Intern 1080p

Ariella is the queen bitch of the entire sales division. When her “stupid” intern shows her he found that he has documents showing she hasn’t been entirely, or even remotely honest in her reports she has no choice but to give in to his demands for a share of the money and taste of her other assets

MILF, BLACKMAIL FANTASY, OFFICE DOMINATION, OLDER WOMAN / YOUNGER MAN, TABOO, THROAT FUCKING

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