Tag: OLDER WOMAN / YOUNGER MAN

Audus Isaiah – Stepmom Swimming Pool Secret TABOO

Whenever you come home for the summer, it’s always a relaxing time. Visiting your family house and lounging by the pool makes your mind relax and give you the vacation time that you really need. This time, your very cute stepmom wants to join you by the pool. You haven’t really been talking to her because your life has been getting so busy. But this time you cannot help but notice her breasts shining in the sun and her tummy rolling out from her wedgie. Should you really be noticing these details? It definitely does not feel right… She invites you to rub her feet – just for old time’s sake. Her feet playfully splashing in front of your face. As soon as you finish rubbing suntan lotion into her skin, something has definitely changed. Your hard-on is obvious and such an embarrassment. Don’t you worry – your loving stepmom definitely noticed. She must be a bad parent to get you so excited. She can’t help but tease you and let you worship her cute, lotioned breasts. She gives you to the count of ten to take care of your erection before anyone else notices your horrible secret.

FEET, LOTION/OIL FETISH, MILF, OLDER WOMAN / YOUNGER MAN, TABOO

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Raven Winter – Giantess Mommy Riding Her Dildo

You wear your dress and heels, your shrunken son is on the ground below you. You don’t know where he is so you hike up your dress and start riding a dildo thinking you’re alone at home. You spot him but don’t stop riding. You act very nice and eventually lean down to pick him up.

GIANTESS, UNAWARE GIANTESS, MOMMY ROLEPLAY, OLDER WOMAN / YOUNGER MAN, SHRINKING FETISH

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Tammie Madison – Exercise with Mom

Before going for a run Mom likes to stretch legs and back from the comfort of her bed. However, today she has a little mishap when trying to get a deeper stretch in her back. Still determined to get out for her run, Mom calls you into her room to give her a helping hand. Each time Mom tries to target her lower back and thighs while stretching she gets a little stuck. If you could just help manipulate legs and push your body against her for a bit more pressure it would really help.
As you help move Mom’s body around and lean into her legs, you cannot help but get a little excited. The moans she lets out with each stretch a bit too much to take. When Mom accidentally pushes back into and feels your growing bulge she gets another idea. Maybe it would be easier if she were to just remove her shorts for stretching.
Finally, Mom decides that you two should forego the stretching altogether. It would be far better for her warm-up if she were to do something more energetic, like jumping or bouncing. The best way to get that type of movement is for you to be inside of Mom. Mommy wants you to be fucked and to ride you. She has decided that being pumped full of your cum would be the best possible warm-up and why would you ever want to deny Mom of what she wants?

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

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Fifi Foxx Fantasies – Sonia Harcourt – Redhead Babysitter Teaches Young Boy How to Flirt & Pleasure Girls, POV – HD 1080p

“Hey, so how was your day?” the babysitter had greeted you warmly when you came back from school. “That bad, huh?”
Sonia tried to make you feel better. Although it was still just the beginning of the school year, you were already starting to have girl trouble. “Oh, gotcha. So, what’s the trouble? Are you just really awkward or are they mean? Or…?” she tried to help. “Oh, just don’t know how to…you know you can talk to girls like normal people. But you mean the ones that you like?”
You had an extremely difficult time flirting with girls. You didn’t know what to say, how to act, and you often embarrassed yourself because of it. “To be honest, there’s no magical secret for you,” Sonia explained. “I mean, I could give you some tips to at least boost your confidence – confidence is a big key. Confidence vs. cocky.”
Sonia then went on to tell you a few pointers on how to talk to girls. “I mean, if you want,” she proceeded to say, “I could show you the way I like things and the way I know a lot of girls that I’m friends with like. Yeah? Okay, yeah, if you’re cool with that. Maybe don’t tell your mom and dad? Just keep it between us – I hate to see you so sad. I want you to feel confident and secure.”
She started off explaining kissing while she stripped down. Her fingers caressed her pink, pretty nipples, showing you exactly what girls found pleasurable and how they liked to be touched. “Just less is always more, especially at this age when everybody’s hormones are going crazy and everything is sensitive,” she told you. “Do you wanna try? Yeah, see? Good, nice and gentle.”
Once you understood how to touch boobs, she explained how to kiss and suck them. “Imagine like a snake with the tongue out,” she said as she flicked her tongue for demonstration. “Do that kinda stuff on nipples. The lighter touch will get things going. Again, I can only imagine what porn has taught you about vaginas, but probably not anything you’re gonna wanna do with your girlfriends, so…”
The babysitter stripped down completely, exposing her bare, shaven pussy to you. She explained the different parts of the vagina, then introduced you to the clit – “the magic button.” She showed you how to rub a pussy, how to warm a girl up, then talked about how to lick a pussy. “Always listen to her breathing, to her body – try and play along. Everybody is different. So, do you wanna try?” she asked.
“I think you’re going to be just fine,” she comforted you as you ran your wet tongue against her pussy. Once you got a feel for how that worked, she moved onto the next lesson – sex. “Oh yeah, you’re hard,” she giggled, “that’s good. I love a man who gets hard from licking vagina. Alright, ready? I’m just going to stick it in…”
“Yeah, go nice and slow to start it, you don’t have to rush it,” she instructed. “This isn’t a porn, this is real life. You’re just here to make you both feel good. Yeah, you’re getting close. I know, it’s okay, it’s a lot for your first time, go ahead.” She told you that it was okay to cum inside of her, so when you were ready, you filled up her tight pussy.
“Oh wow!” she smiled. “There you go. Wow, that was a lot. Okay, so? You feel a little better now, a little more confident about going to school and talking to girls? You got this.”

BABYSITTER, OLDER WOMAN / YOUNGER MAN, VIRTUAL SEX, REDHEADS, SEX ED, INSTRUCTIONAL

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Fifi Foxx Fantasies – Sydney Paige – Dad’s Ultimate Taboo Fantasy: Watching Mom Corrupt & Fuck Their Young Son, POV – HD 1080p

A very forbidden, taboo experience…
“Hey sweetie, how was work?” your wife asked you, her petite, beautiful body exposed in red, lacy lingerie. “I dressed up for you today, I thought we could have some time together.”
You loved how hot and horny your wife was, but you had something else in mind – something far naughtier. “What do you mean? What did you have in mind?” she asked. “Inc*st fantasy? I did hear that was popular. So, did you want me to, like, pretend to be your sister or something? How would you like to play this out? I mean, I know you married me because I was open-minded.”
“Our son? Oh, um…well, I wouldn’t be totally opposed to that – I mean, he does need to learn how to pleasure a woman in high school and college,” she went on to say. “Is that what you really want to do? Is there anything you specifically wanted to see?”
She was up for it, as long as your son was, and it wouldn’t be hard to convince him. You wanted to see your beautiful wife corrupt your sweet, innocent boy – a real life mom and son experience. So, the two of you called him in.
“Hi sweetheart,” Mom smiled at your boy. “How was your day at school? Well, Daddy has brought you in here because there’s something we wanted to do today. We wanted to teach you some of the things you’re going to need to know further in life – things of a sexual nature, if you will. Isn’t that right, honey? So, your father would be observing to make sure I educated you properly – what would you think if Mommy showed you a few things?”
Of course he agreed. Your wife knew exactly what to say to make him want to engage in such a forbidden, taboo act – she knew just how to lie and that turned you on even more. “First thing I’m going to do is take my hand and rub it over your pants and naughty parts,” she told him.
“Just like that, honey?” she smiled devilishly at you. “Is that what you wanted to see?” She turned back towards your son, who now had a hard-on, and offered to help him take care of it. “You know, you’re going to see plenty of these through-out your life,” she said as she exposed her perky, beautiful breasts. “Now just take a look at these and I’m going to rub you a little bit more.”
“Our baby’s cock is getting so hard, honey,” she said to you, then stripped him down. “He’s got such a big cock – I guess he got that from you. You like watching me stroke our son’s cock? Your father’s just making sure I do this correctly.”
God, what a turn-on. Watching your wife pleasure your son’s cock. “So, what I’m going to do now is grab the base of your little cock and I’m going to put my mouth on it – is that okay, honey?” she asked before wrapping her warm, wet mouth around his virgin cock.
“Mm…are you enjoying this, baby?” she turned towards you, then went back down. She giggled at your son’s twitching body, “Our son is so turned on.” Things only progressed from there – she wanted nothing more than to fulfill your inc*stuous fantasy.
Her voice was sweet and seductive as she manipulated and corrupted your son. She wanted him to feel comfortable, to trust her, so that he’d give himself to her. “Come here, baby,” she motioned him. “Take your hands and caress my soft skin, feel my breasts – oh, don’t be shy, sweetie. Maybe I should teach you the ultimate? What do you think, hubby? Should I let our son inside of me?”
She laid back, guided his cock inside of her, then let him fuck her. She moaned and then giggled, “Oh, his cock might feel better than yours…” When she felt him throbbing, she looked at you lovingly, “What does Daddy think? You want our son to cum in me, Daddy? Cum in Mommy, baby, and let Daddy watch.”
So, he did. He filled her pretty pussy with his huge load, and she licked his cock clean. “My baby’s cum tastes so good,” she purred. “Maybe we can have some more lessons later, sweetie.” She then told him to clean up and to finish his homework.
“So, honey, what’d you think?” she sat naked in front of you, your son’s cum dripping out from her pussy. “His cock felt so good.”

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

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Fifi Foxx Fantasies – Nikki Brooks & Anastasia Rose – The Man of the House: Son’s Violent Sexual Behavior, POV – Mom & Sister, Forced Sex – HD 1080p

By far, one of the most intense & disturbing taboo clips I’ve ever released…
“Lately, I’ve been thinking about getting him a therapist,” Mom told her daughter. “Someone who is well educated, or at least someone who specializes in special cases.”
“Maybe he will be okay with it…” Mom went on to say, “he has to know that what he’s doing is wrong.” They were scared of you. Ever since Dad was out of the picture, you declared “man of the house” and made sure that Mom and your sister, Anastasia, knew who was boss.
You had become terribly sexually violent. You didn’t care how many times they cried, how times they begged you to stop – you got what you want. They couldn’t defend themselves against you, and it happened quite often. So much that they sat together quietly trying to find a solution to the aggressive, inappropriate behavior.
“Hey,” they put fake smiles on their faces when you entered the bedroom. “I was just talking about you,” Mom quickly said. “Your sister is going to go to her friend’s house, and why don’t I invite your buddy over and order some pizza? You guys can rent a movie…”
Friend’s house? No, she wasn’t going anywhere – they knew the rules. “Why can’t she go to her friend’s house?” Mom let out a nervous giggle. “It’s her friend…Dacey. You know Dacey’s mom likes taking the girls to the mall and…excuse me.” You had snapped at your mother, telling her that your sister was dressed like a slut, and she defended her.
“She does not look like a slut,” Mom said angrily. “No, there’s not going to be any boys at the mall. Why are you concerned with your sister’s life like that? Let her do her thing, okay? Sweetie, we’ve had a really tough couple of months and I understand everyone is re-adjusting to everything. Just let your sister go have some fun.”
They tried really hard to get you to hang out with your friend – a little too hard. “Why don’t you call him, huh?” Mom repeated, but that only pissed you off more. “I’m not trying to get rid of you, sweetheart.” You violently yanked on her arm and Mom comforted your worried sister who now wanted to stay to protect her.
“Your sister is going to go, okay?” Mom said sweetly. “Listen to me, sweetheart, you don’t run her life, okay? She’s growing up and she just…” Another arm jerk for the stupid bitch who thought you gave a damn what she thought. This, once again, upset your sister, but you knew there was nothing she could do to stop it. That neither of them could do.
“You know, bro, I’m not going to Dacey’s tonight or anything,” Anastasia blurted out with a smile on her face. “We were talking about a sleepover, but we didn’t set a date or anything.” Things were getting awfully suspicious, so you decided the both of them needed a reminder of who was in charge.
You yanked down your sister’s dress revealing her young tits, and she embarrassingly tried to cover up. “D-did you hear him? He wants me to…” Anastasia turned towards Mom with a shocked face, and Mom attempted to cover her up. That was until you told Mom to take them back out, and she did so obediently. “It’s okay, Mom…” Anastasia comforted her.
Mom tried the whole “rent a movie” bit again, which only caused you to become more frustrated. It was time for them to pleasure you again – it didn’t matter if they were willing or not. You’d yank on their bodies, shove their heads down on your cock, then push them back so you could see the tears in their eyes from gagging on it.
Mom and Anastasia tried to defend one another – how sweet. It didn’t matter, though, you always got what you wanted in the end. It didn’t matter who sucked your cock first, who you forced your cock into last – they both got it.
They needed to respect you as man of the house. They’d do everything you said, no matter what it was, or they’d be trained into obedience. It didn’t matter how many times Mom cried, “It’s not right.”

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

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Shiny Cock Films – Jane Cane – Mom and Son Summer Vacation – Complete

Mom and Son Summer Vacation Together, Part 1 – 6:00 Wade has had a hard first year in college. He studied hard, didn’t party or let girls distract him, and his hard work paid off. He made the president’s list! Mom is so proud and wants to reward her son’s hard work, so she rents a RV for them for the summer. They will be driving to a remote resort in the woods where they can relax and unwind and spend some much needed bonding time together. When they arrive, Wade goes to check things out and comes back with a shocking revelation to tell his mother. They are actually in a nudist resort. After being shut in all year focusing on his classes, he can’t help but be immediately aroused looking at all of the beautiful people. He is so embarrassed of his boner that he doesn’t want to go out. Mom feels awful. She had no idea what she was getting them in to. She doesn’t want to ruin their summer, but if she leaves, she will lose all the money she paid for them to stay there for the month. She has no choice, it was her mistake, she should have read more about the resort. She strips to her bra and panties to show her son that it’s natural and he shouldn’t be ashamed, but this makes Wade even harder. He never knew how hot his mom was. Seeing the distress in her son’s face, she knows the only thing to do is to get her hands dirty. She strokes her sons cock until he shoots a big load all over her tits. Now he feels like he can go out and explore a little more. Jane Cane, Wade Cane, Shiny Cock Films, hand job, handjob, nudist colony, family, related Mom and Son Summer Vacation Together, Part 2 – 6:57 Wade and his mom come back from dinner at the resort. He is all flustered. He had a rock hard cock all through the meal. Everyone around them was either half naked or barely clothed. He can’t get his erection to go down. His mom knows what a problem he is having. He just wants to go home, but mom isn’t giving up. She is determined to have a nice summer with her son. She missed him all year while he was away at school. She would do anything for him. And to be honest, she is a little aroused herself being in this atmosphere. She tries to sooth her son by talking to him, but it doesn’t work, all he can think about is his raging boner. Mom had a few sips at dinner and suggests she do what she did earlier that day to help him out. He agrees and she starts to stroke his cock. She can tell he really likes it, he is moaning and she can feel how hard he is. She gets even more turned on and starts to suck his cock. Wade can’t believe that his mom has his cock in her mouth. He can’t take it anymore and explodes down her throat. Jane Cane, Wade Cane, Shiny Cock Films, blow job, blowjob, cum in mouth, nudist colony, family, related Mom and Son Summer Vacation Together, Part 3 – 9:00 It’s been a week since Wade and his mom arrived at the nudist colony. His mom made a mistake when reserving their spot and didn’t know what she was getting them into. She doesn’t want to lose her money so they decide to stay. Mom has been giving her son handjobs and blowjobs regularly to keep him happy. Anytime he goes outside he gets so turned on by all of the beautiful people. Wade has had an idea for the past few days, but doesn’t know how his mom will react to it, so at dinner he makes sure she has a couple of glasses of wine. When they get back to the RV, he sits her down and tells her how much he appreciates what she has been doing for him. He starts to massage her shoulders, then down inside of her dress, up her legs. Mom knows this is wrong, but she is so turned on. Her pussy is dripping wet. Wade whispers to her that he wants to make love to her. At first, mom is reluctant, but her son is really a smooth talker telling her how much he loves her. She can’t resist any longer. She takes off her clothes for her son and gets in the bed. She lets him have his way with her body riding him, letting him on top of her, and ultimately cumming on her perfect ass in doggystyle.

MILF, MOMMY ROLEPLAY, OLDER WOMAN / YOUNGER MAN, PAWG, TABOO

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Fifi Foxx Fantasies – Whitney Morgan & Carmen Valentina – Wasted Mom & Aunt Need Son’s Cock, POV – HD 1080p

A taboo experience where mommy & auntie are heavily inebriated…
“Cheers!” Mom smiled, her glass clinking against her sister’s. “I’m glad we stopped by the store and got some more wine.” The two were still dolled up after a night of heavy drinking and dancing.
“That guy was so cute and now I’m horny,” Aunt Carmen slurred, her legs spread and her bare pussy exposed. That’s when you walked in. “Oh! Oh honey,” Mom was startled, but let out an embarrassed laugh.
“You didn’t see your Auntie’s pussy,” Carmen blurted out. “I’m sorry, should Mommy offer you a drink?” Mom shook her glass at you. “It’s only wine – it’s like grape juice but with a little bit of a bigger kick.” As the two rambled on, Mom caressed Auntie’s skin with her fingers.
“Oh, that feels good,” Carmen told her, then saw the surprised look on your face. “Oh don’t worry, your mommy touches me like this all the time.” Mommy agreed it was okay because you guys were “family.”
But things progressed right in front of you. They started making out and you felt your face grow hot. “Did you want to give Auntie a kiss? Cause you look jealous! You want to give her a kissie kissie? You don’t want to give her one? Maybe you want to give Mommy a kiss?” Mom said coming up and pressing her lips against yours, then plunging her tongue inside your mouth.
“Why don’t you give Auntie a kiss right here?” Carmen said spreading her legs and pointing to her pussy. “What’s the matter?” Mom slurred, then began joking around. “When a man and a woman love each other in a very fun way, they give each other kisses in their downstairs area.”
“Give me kissies, show me you love me. I couldn’t find any man to give me kisses down here tonight,” Auntie told you. “I love my nephew!” Mom instructed you on how to do it better as she watched you pleasure Auntie. “You gotta put your tongue in it, like you’re french kissing!” Mom told you.
“Do…do you want to suck on Mommy’s tits?” Mom asked, then struggled to get her tight, white dress off. You went back and forth between the two wasted women. Aunt Carmen shared Mommy’s tits with you, and the both of you sucked and flicked your tongue against her nipples.
Next, you shared Aunt Carmen’s tits with Mommy. You were throbbing hard, and Mom and Auntie noticed. They shared your cock, stroking it together, then took turns sucking it. “I don’t even go down on Daddy anymore, but you, baby boy, I could suck that cock all day and all night…” Mom confessed.
“Have you ever been inside a pussy?” Auntie asked. “Or is he still a virgin?” Mom had no idea. “I bet he’s been fucking cute girls left and right – have you?!” Mom blurted out.
“Why don’t you come over here and give Auntie what she wants…” Carmen told you, “what she’s been craving all night long. I’ve been trying to find a man all night to fuck me and your mommy, and we just didn’t have any luck tonight…until you came in!”
The two rushed to get their clothes off, then laid back. You started off with Aunt Carmen, making her orgasm, then switched over to Mom. “Good boy,” Mommy moaned, “right there. Cum with me, my baby boy.” Mommy was wild as you fucked her, and eventually, you came inside of her.
Mom and Auntie asked for more kisses, then slid their tongues against one another’s. They were so wasted, but wanted even more wine to share with you. As you left the room to get them some more drinks, you saw them caressing and kissing one another.

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

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Katie71 – Stepson’s BBC

My stepson has a nice BBC and I love fucking him when his dad leaves. This particular day I was headed to play tennis when I walked in on him watching some porn. After getting a closer look I noticed he was watching my porn which I had no idea he knew about. Anyways, that really got me in the mood after seeing he was jacking off to me so I made my move on him and had some really good sex riding front and back on his huge BBC. After we were done I told him to keep watching my porn and smelling my panties until I get back when I want him to give my ass a good beat down. I love my stepson.

TABOO, OLDER WOMAN / YOUNGER MAN, BBC, VIRTUAL SEX, POV

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Josie Cairaway – Stepmom Say’s: Edge First Then Cum

Hey stepson. We have the house all to our selves for the night. You know what I want to do. I want to play with your big, rock hard cock. I want you to cum in my mouth. I need to taste a really big load from you so first I’m going to edge you over and over. I want your balls to be really full when I finally let you cum. I’m going to suck, lick, stroke and tease your cock and balls until you’re twitching. Then, when I’ve tasted your pre-cum over and over, I’ll give you a cum countdown. I’m going to lick your balls and show you my tits until I get to one and then you’re going to unload in stepmommy’s mouth so she can swallow your yummy cum.

TABOO, BLOW JOBS, CUM SWALLOWERS, CUM COUNTDOWN, OLDER WOMAN / YOUNGER MAN, REDHEADS

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