Tag: OLDER WOMAN / YOUNGER MAN

Fifi Foxx Fantasies – Mom Sells Daughter’s Virgin Body to Perverts, POV – HD 1080p – Carmen Valentina

“So, I see you were interested in the ad…” Carmen started to say, “seems like you’re a little pervert.” Beside her, she had a number of dirty panties that belonged to her young, pure daughter. “A nice, young, wet, bald pussy was on these – don’t you want to sniff them?” she asked.
She laid out the stained panties for you, letting you examine each one before deciding which ones to buy. “So, you can fork up the cash if you want some of these,” the woman said bluntly. Being a single mom, Carmen needed some extra cash, and what better way to make some by selling her daughter’s panties to some sick pervert.
“Look at those pussy juices,” she pushed the different colored panties towards you. “I’ll make sure to put them in ziplock bags so you can savor the scent.” And that wasn’t all she was selling. “For an extra fee, you can fuck me,” she said exposing her perky tits, then penetrating her juicy, pink pussy with her fingers.
And if you wanted her daughter? Twice the price. Carmen knew what type of guy you were – what you really wanted. She knew that you wanted to take advantage of her innocent, naive, virgin daughter. You constantly fantasized about all the twisted things you would do in a situation like that. And seeing her mom give her up without a care in the world was too arousing – Mommy was pimping out her little, sweet girl to be someone’s dirty whore.

TABOO, DIRTY TALK, LINGERIE, MILF, OLDER WOMAN / YOUNGER MAN, POV

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Fifi Foxx Fantasies – Mom Helps Son Relax – Son is Stressed over Big Test & Mom Makes Him Forget about It, POV – HD 1080p – Roxxxie Blakhart

Enjoy this taboo experience with a brand new Mommy…
“Hey honey,” Mom said sitting down beside you on the bed, “how are you feeling?” She knew that you had a big test tomorrow in one of your classes, and was worried that you were over-exerting yourself trying to study for it.
“Have you had something to eat today? Are you drinking enough water?” she asked concerned. “You don’t need to stress about the test – we can get through this. Maybe…there’s a little something I can share with you that helps me relax. I know it might be a little weird because I’m your mom…but self-satisfaction is really important and stress relieving.”
“I know it’s a little uncomfortable, but just trust me,” Mom said offering to help loosen you up. She unfastened your pants and wrapped her warm, soft hands around your cock. “See, that feels better already, doesn’t it?” she smiled as she stroked your cock. “This is all you’ll be able to think about it – you won’t even be able to think about the test. This can your little euphoria.”
“Just relax,” she repeated with a gentle, soothing voice. To make you feel more comfortable, she stripped down and showed off her beautiful body to you. “Get close to Mommy…I’ll make you feel all better…I’ll help you. Go ahead and put it in Mommy’s pussy…”
You penetrated her tight, pink hole, and she moaned loudly as you fucked her. “Such a good boy,” she smiled warmly, “I’m so proud of you.” After you had cum, she told you to get a nice, cooked meal and a big glass of water. “Don’t worry about your test anymore today, okay? You feel all better now, don’t you?”

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

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Fifi Foxx Fantasies – That’s My Mom! Wait, That’s Me?! – Son Discovers He’s Inside His Mom’s Body – HD 1080p – Christina Sapphire

He woke up in an unfamiliar room. His blurry, tired eyes looked down to see painted fingernails and smooth, shaven legs. “I don’t remember this happening at the party last night,” he mumbled to himself. “This is a little weird. And my toenails, too?”
His fingers pressed against his throat. “My voice is lower than this…” he said confused. “I mean…I think it is. Everything sounds funny.” He quickly realized he was wearing lingerie, and underneath that, he had female body parts in place of his usual male parts. “Uh…dude, what the hell happened?” he asked examining his feminine figure. “These are not mine.”
His fingers ran through the long, straight, dark hair that fell past his shoulders. “Smells good, too. Girls use nice shampoo,” he said smelling its pretty scent. “And the ears are pierced….and a wedding ring? What the hell is going on?”
He walked off to find a mirror to see what he looked like. “Glasses? Well, I wear glasses so that’s okay. Lipstick? Am I wearing eyeliner?” he said with his face pressed up against the glass. But then it hit him. “Wait…” He pulled back from the mirror and stared at his reflection. “That’s my mom! That’s…that’s…my mom. That’s…I’m not supposed to look like that,” he said in shock. “Oh my god…”
Although he was surprised, he couldn’t help but continue examining his new, beautiful, mature body. He had never seen Mom in this way before, and being inside of her made it that much more interesting. He walked back out to the bedroom and began to strip off his lingerie. He fondled, groped, grabbed, and licked his new female body parts. Everything felt so good…so different from his own male body.
He would eventually learn how to masturbate as a woman, rubbing his fingers against his clit, and then penetrating himself. There were so many exciting things to explore – even Mom’s tight, little asshole.
He wasn’t sure how this happened…why it happened. All he knew was that he loved being inside a woman’s body and all the pleasures that came with it – even if it was his mom’s.

GENDER TRANSFORMATION, TRANSFER FETISH, TRANSFORMATION FANTASIES, TRANSFORMATION FETISH, TABOO, OLDER WOMAN / YOUNGER MAN

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Fifi Foxx Fantasies – The Naughty Game: Mom Manipulates & Tricks Young Son into Fulfilling Her Perverted, Sexual Needs, POV – HD 1080p – Nikki Brooks

Warning: this is an extreme taboo clip. Intended for those interested in an intense & “disturbing” mom/son experience. One of my favorites by far.
“Hi honey…” Mom said with a big, warm smile, “whatchu doing? You cleaned your room! Thank you for being a good boy. You’re a big boy now, you cleaned your room all by yourself.” She held out her hand for a high five, then pulled back with a sweet giggle.
“Hey…do you wanna play a game with Mommy?” she asked charmingly. “I came up with this really, really cool game – do you wanna try it? I’m telling you…you’ll have lots of fun with this. You know, me and Daddy used to play this game all the time, but you’re probably not a big enough boy, right? I guess maybe we should play with one of your board games…”
Of course you were a big boy. You wanted to play whatever game Mommy was talking about. What you didn’t know, though, and what you didn’t understand…was that Mommy was horny, and she was manipulating her sweet, young, innocent boy into touching her in a very naughty, sexual, and immoral way.
“Now that I really think about it…you really got to be a big boy to play this game,” Mom started to say. “I wouldn’t want you to, you know, be too shy or something. It’s okay, we can play another game or something. You sure? Okay, I’ll see if you can handle this big boy game. Like I said, your dad was really good at this game…”
She went on to explain that it was a kissing game. And if you won? She’d give you a nice, big bowl of your favorite ice cream with everything on it – chocolate syrup and sprinkles of every color. “That’s, of course, if you win,” she smiled, then shook your small hand. “Challenge accepted!”
There were three strikes for each person. You’d start at Mommy’s feet, kissing your way up, and if she started to giggle, she’d get a strike – then it would be her turn to do the same to you. Mommy knew exactly what she was doing – she knew what to say and what to do to get you to fulfill her perverted needs. The best part? You wouldn’t even know you were doing it – it was just a game you were trying to win….
“Feels good, right? Uh oh, are you going to give up? Are you gonna be a big boy?” she said as the game progressed into something much more. Your pee-pee was inside of hers, and she was bouncing up and down on it. “That’s right, you’re just like Daddy…and you play the game so much better than he does – cross my heart!”
And don’t forget, big boys keep secrets.

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

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Fifi Foxx Fantasies – Just Use My Body, Son – Mom Helps Son – Son Takes Too Much Viagra before Date, POV – HD 1080p – Ivy Secret

“What’s the matter?” Mom asked with a concerned look on her face. “Why are you sweating so much, honey? Are you okay? Are you nervous about your date?”
In an attempt to “impress” your date, you had taken two of Dad’s Viagra pills, and now you had a rock hard, throbbing cock that you couldn’t control. “I know you’re nervous about your date, but you’re young, you don’t need that,” Mom lectured. “That’s for older guys that need help. How many did you take? You’re supposed to take, like, half – how much did you take? You took two? That is way too much! No wonder.”
She looked down at your erection in disbelief, her hand pressed against her head, and sighed. “Did you try to jack off? The only way you’ll feel better is if you cum – you have to cum. Your date is in an hour, you have to get rid of that thing. This is a really nice girl, you can’t screw that up,” she said bluntly.
Of course you tried to jerk off, but the Viagra was so strong, it didn’t do anything. “Alright, we’re just gonna get you off so you can go on this date,” Mom started to say, “and don’t you ever do this again, and we’re not going to talk about this, okay?” She sat up, wrapped her hand around your cock, and started stroking it. “How does that feel?” she asked. “Does it feel like you’re going to cum? Not sure?”
“Maybe if I take my top off…” Mom thought out loud, then pulled off her shirt, “just trying to help.” She encouraged you to take deep breaths, but the stroking wasn’t doing much for you, so she decided to try her mouth. “Still nothing? That always works for your father – that’s like my go-to move when I’m trying to get him off,” she sighed.
“Okay, this is what we’re going to do…you’re not going to like it, I’m not going to like it, but it’s what we gotta do,” Mom began to say. “I’m just going to let you use my body, just use it, put your penis inside of me, and I’m going to let you cum.” You pushed yourself into Mom’s pussy and she let out a soft moan.
“It’s okay, just cum…” she said in-between breaths. “Yes, just use me, fuck me…yes, there you go.”

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

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Primal’s Taboo Sex – Son’s Crush – Part One – Diamond Fox

Diamond has been noticing her son looking at her very strangely. Then, as she is exercising in her room she feels his eyes on her. She starts to scold him but realizes it is natural for sons to have…feelings, especially at his age. She is his first crush and she wants to handle it the right way

TABOO, MILF, COUGAR, OLDER WOMAN / YOUNGER MAN, SLUT TRAINING, DOMINATION

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Family Manipulation – Aunt Addie is Cooler Than Your Mother – Addie Andrews

My Aunt Addie decided to check up on me, but on thing lead to another and next thing I know, she’s groping my balls! I had no control over what happened next, my cock grew bigger and she just wanted it in her mouth. Watch me fuck my Aunt deep inside her MILF cunt. She looks so good as she slides her wet pussy all over my big shaft. It’s so hot seeing her throw her head back and moan with pure satisfaction from juicy big cock.. I finally fill my aunt’s pussy up with my cum and make her promise not to tell my parents!

TABOO, MILF, POV SEX, OLDER WOMAN / YOUNGER MAN, CREAMPIE, BLONDES

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TabooHeat – My Hot New Stepmom – Vanessa Cage – Scene One: Mom is Horny – Scene Two: Cheating on My Husband – Scene Three: My New Girlfriend – Scene Four: Video Revenge – Scene Five: Phone Call Revenge

Scene One: Mom is Horny
My step-mom Vanessa has been going through a lot lately and she really needs someone to vent to… Late one night, after my dad falls asleep, she sneaks in to my bedroom and decides to vent to me about my dad… “Your dad just hasn’t been pleasing me lately,” she begins to tell me… But I saw that he bought her a new car just last week and he’s always taking her on vacation and giving her money for girls trips! What else could she want?! She explains to me that she really wants someone to please her sexually. She starts to rub my cock over my pajama pants… “whoa, whoa, whoa!!” I shout, but I can’t help the fact that my cock is getting harder… I can see her nipples through her nightgown as well, and I can’t stop staring at them… “Have you ever gotten a blowjob from a girl at school?” she asks me… “Not from anyone who looks like you!” I tell her. She pulls my cock out and then she pulls her big tits out from underneath her nightgown and I can’t help but play with them… She starts to suck my cock while I play with her big, natural tits and I can’t help but explode inside of her pretty mouth! She swallows every last drop of my cum and even lets me grab her big tits again before she goes back to bed, next to my snoring father…

Scene Two: Cheating on My Husband
I am doing my homework in my bedroom one afternoon when my step-mom comes storming in! Vanessa starts screaming about how my dad has been cheating on her with his assistant and THAT is why he hasn’t been having sex with her! “She’s older than me too! She’s some MILF with big, fake tits and glasses! I didn’t even think that that was his type!” she keeps shouting… “Screw your homework and screw me instead!!” She pulls her army green dress off of her body and asks me to take my pajama pants off, so she can suck my dick for a little bit… She tells me that I don’t have to go to school tomorrow and that makes me happy, so I want to make her happy as well! “You know what would be funny? If I creampied you and then we saved some for him…” I tell her. “Yeah, I’ll rub some of your cum on my lips and then kiss him when he gets home!” she says to me. Damn, she must be really mad at him!! “Come and fuck your step-mommy,” she says, as she lays back on the bed and spreads her legs for me. My cock is so hard just looking at her pussy and her big tits. I shove my cock deep inside of her pussy and it feels so warm and tight! “Can we try it from behind?” I ask her… She gets up to move in to the doggystyle position but she sucks my cock again before she does. God, my step-mom is SO hott! My dad is crazy for cheating on her. “You’re such a good step-son making sure your step-mom is happy!” she moans, as her ass shakes back and forth on my cock… “It’s so wrong but it feels so right! I want you to give me that huge load inside of my pussy!” she begs… I cum deep inside of her pussy and it feels so good!

Scene Three: My New Girlfriend
My dad is in the shower before work, and my step-mom Vanessa is hanging out in some sexy, turquoise lingerie. She pulls me in to her bedroom… “Your dad takes the longest showers! Don’t you want to have sex with your step-mom?!” she asks me. At first I am hesitant because I am really nervous about my dad coming out of the shower and catching us! But she pulls her big tits out from under her lingerie and I am easily convinced… She starts to suck my cock and I am getting really turned on! I ask her if we can do it from behind first, but then I change my mind… “Lets do it with you on your back first!” I tell her. I start to fuck my step-mom, and she promises me that if my dad catches us and disowns me then she will take care of me. That makes me feel a little bit better about doing this behind my dad’s back… “That’s a good boy! Fuck your step-mommy!” she moans. “It’s so hott knowing that your father is just a couple of feet away from us!” Her big tits keep bouncing up and down while I fuck her hard. I keep fucking her until I get close to cumming… then I pull out and explode all over her face!!

Scene Four: Video Revenge
My dad is in the shower before work, and my step-mom Vanessa is hanging out in some sexy, turquoise lingerie. She pulls me in to her bedroom… “Your dad takes the longest showers! Don’t you want to have sex with your step-mom?!” she asks me. At first I am hesitant because I am really nervous about my dad coming out of the shower and catching us! But she pulls her big tits out from under her lingerie and I am easily convinced… She starts to suck my cock and I am getting really turned on! I ask her if we can do it from behind first, but then I change my mind… “Lets do it with you on your back first!” I tell her. I start to fuck my step-mom, and she promises me that if my dad catches us and disowns me then she will take care of me. That makes me feel a little bit better about doing this behind my dad’s back… “That’s a good boy! Fuck your step-mommy!” she moans. “It’s so hott knowing that your father is just a couple of feet away from us!” Her big tits keep bouncing up and down while I fuck her hard. I keep fucking her until I get close to cumming… then I pull out and explode all over her face!!

Scene Five: Phone Call Revenge
Vanessa calls me in to my parent’s bedroom to tell me how she hasn’t sent my dad the pictures or videos yet. She tells me how they’re really hot but she is also really nervous to send them. She wants to send him the pictures and videos right now, because she knows that once he sees them he will be very upset and probably call her… and she wants me to be there fucking her, as she talks to my dad on the phone! I start laughing and I agree to go along with her evil plan. “Do you wanna see my tits?” she asks me, and of course I say yes… She rubs her hand over my boxer shorts and my dick starts to get harder and harder. She pulls my cock out and starts to give me a blowjob, “Don’t you love it when your step-mom sucks your cock?!” she asks me. “There’s nothing better!” I tell her. My dad starts to text her back and tells her that he is coming straight home from work! But he does have an hour long drive home… so she keeps sucking my cock! She picks up her phone again and starts to call my dad as she is sucking my cock… “Hey babe! Do you know what I’m doing right now? I’m sucking your son’s cock and I’m doing it in our bed!” she says to my dad on the phone! She knows exactly how to get revenge… and she tells him that she is going to divorce him! “Hey sweetie, do you want to put that cock inside of me?!” she asks me, while she is still on the phone with my dad!! I start to fuck her on my dad’s side of the bed, while she keeps moaning in to the phone. She also tells my dad that she is going to take me with her when they get divorced! I definitely can’t say no to that! She hangs up the phone so we can keep fucking before my dad gets home from his long drive home from work… I keep fucking her hard until I cum all over her face… and then she takes pictures of my cum all over her face! “I can’t wait to send these pictures to your father!” she says…

TABOO, OLDER WOMAN / YOUNGER MAN, MILF, HANDJOBS, BIG TITS, FUCKING

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Vanessa Lee – Naughty stepmom fucks stepson roleplay

You are my stepson who is home on break from college. Without bothering to knock, you enter my bedroom while I’m in the middle of changing my clothes. I pretend to be mad at first, but I am secretly turned on. My hubby is away on a business trip and this can only lead to trouble. I use a realistic dildo and masturbate in this fun roleplay.

TABOO, ROLE PLAY, BIG TITS, MILF, MASTURBATION, OLDER WOMAN / YOUNGER MAN

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Bettie Bondage – Wet and Blackmailed MILF

Oh! I didn’t realize there was someone in the bathroom with me! What’re you doing in here? I think perhaps its best if you use the guest bathroom downstairs…hello? Please leave! I need to get dressed. Hmm. Alright, well at least pass me that towel…ok fine, I’ll get it myself. My goodness, you’re a strange boy, aren’t you? Ok then, let’s get out of the bathroom, I need to dry off and get dressed.
Excuse me? My…phone? Oh, no, have you been looking through my cell phone? Listen, I will not be talked to in that manner. I knew you weren’t the best influence for my boy but this is too far, mister – get out of this bathroom! What? Wait, are you…blackmailing me? My God, I can’t believe this is happening. Some guest you are! So, you’re saying you’ll tell my husband about all those pictures you found, if I don’t…show you whats under my towel? God, I can’t believe I’m even entertaining this…ok, fine, but quickly, just a flash.
Good enough? Ugh, of course it isn’t – I’ve only made things worse for myself by showing you my dripping wet, naked body, haven’t I? I might as well have stroked your cock to full mast myself! Of course, now you want more…I can hardly blame you, young boys like you are so eager to put their young cocks to use! God, I can’t believe this…ok. We need to be quick, so just sit down and take it ou – woah! Wow. No, it’s ok I just didn’t expect you to be so…wow. Ok, well, let’s get ot work then…let me just wrap my hand around this fat, young cock and, mmm, stroke it just like that. Do you like that? I’m a very talented woman, I’m sure you haven’t had a beauty like this handling your cock yet, have you? Well, to be quick about it I should probably use my mouth, huh? What about dirty cock? Do you think you’ll cum quickly if I tell you to let that young jizz shoot all over my face, my tits, my pussy? Mmm…

BLACKMAIL FANTASY, MILF, TABOO, OLDER WOMAN / YOUNGER MAN, VIRTUAL SEX, POV

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