Tag: OLDER WOMAN / YOUNGER MAN

Meana Wolf – Cheating Mommy

I know you saw me with that man today. Are you going to tell your father? I know you’re upset. I didn’t think you would see me. I want to be a good mother, but your father and I don’t love each other anymore. I would never leave you… you’re everything to me. I know you are confused… I’m trying so hard to stop how I feel. Are you jealous? He reminded me of you… that’s why I did it. I want you so badly… I’m trying to be a good mother… I want things that I shouldn’t want… And I know you do too.

TABOO, MILF, MOMMAS BOY, OLDER WOMAN / YOUNGER MAN, CREAMPIE, ASMR

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Bettie Bondage – Fucking Your Best Friend’s Mom

Oh, hey there honey. What’re you doing down here? I thought you boys were having a sleepover, shouldn’t you be up there playing with that new console I just got my son? A fight? Oh, well, I’m sorry to hear that. A fight about what? Was my boy making fun of you? He can be so cruel. He was?! I’ll have to talk to him about this…what was he making fun of you for? Come on, honey, you can tell me. I can’t help you unless you talk to me. I don’t want you to feel badly about something silly my son poked fun at you for…
…your…oh my! Your penis? Well, there’s nothing wrong with having a smaller sized penis, you know what they say, its the mo…oh. Not small. So, my son was teasing you for having a…big penis? My my. Well. How big are we talking? Like…this big? Oh, bigger…oh, well. You know, I think I might need to see what’s going on with your penis. To really help you. Oh, it’s alright. I can tell you’re excited, and I’m not upset. In fact, I’m quite happy. I love knowing you like me that way. It’s very sweet. And it makes me very excited. Aren’t you excited?
There, that’s better, isn’t it? Wow, you certainly are big, aren’t you! You know, lots of girls love a bigger penis. Myself included. Now, why don’t you get a little closer, and I’ll show you all the ways that a big, fat cock like yours can make a woman like me very, very happy!!

MILF, POV, VIRTUAL SEX, ROLE PLAY, OLDER WOMAN / YOUNGER MAN, CREAMPIE

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Tammie Madison – JOI from Your Girlfriend’s Mom

It always a bit awkward when you have to spend time alone with your girlfriend’s mom. She is hot and doesn’t seem to be aware of the effect her cleavage and revealing outfits have on you. Usually you can cover up or hide your erection from her, but tonight she notices. “There is no way I am letting my daughter go on a date with you while that thing is fully loaded. You better get to work relieving g yourself of that hard on. What are waiting for? Whip it out and get to work.” You cannot believe that she is serious! How can you possibly masturbate right in front of her? When she calls up to her daughter to slow her date prep, you realize this milf is serious. Your girlfriend’s mom wants you to masturbate for her. She starts touching herself, revealing more, and teasing you. There is no way you want to pass up the opportunity to stroke and cum with an older woman, so you start doing as she says. The only difficulty now, is holding back so that you don’t explode before she counts you down. Clip contains: taboo jerk off encouragement and instructions from your girlfriend’s – stroking for an older woman while your girlfriend is upstairs – cumming with your girlfriend’s mom.

TABOO, JERK OFF INSTRUCTION, MILF, MOMMY ROLEPLAY, OLDER WOMAN / YOUNGER MAN

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Fifi Foxx Fantasies – Whitney Morgan – Wasted Mommy Wants Son’s Cock, POV – HD 1080p

After a night out with her friends, Mom drunkenly slammed down onto your bed. “Hey baby,” she slurred obnoxiously, a big smile on her face. “How was your night? Oh, I’m sorry…were you trying to sleep? I just wanted to come in and check on you and see how you were doing…”
“I know I was being a super bad mom by letting you stay in the house all by yourself tonight,” she rambled, “but Mommy needed to go out and have some fun with her friends.” Her hand caressed your face and she pinched your cheeks, “Aww…you’re so cute. You’re growing up to be such a handsome boy! Do you know how handsome you are?!”
Mom started rubbing your chest, then sat up and puckered her red lips. “Oh my sweet baby boy, why don’t you give Mom a little kiss?” her warm breath hit your face and you shoved her away. “Don’t push me away! You used to give Mommy goodnight kisses, morning kisses, and good-bye kisses all the time…come on, give Mommy a little kiss. Oh, you think you’re getting too old and grown up for kisses?”
“Yeah, you’re feeling really grown-up, aren’t you?” she smiled devilishly as her hand brushed against your cock. “Did you just bat me away? Mommy’s just having a little touch…just a little touch. Mommy might have had…a few too many glasses of wine. Can I just sleep in your bed with you?”
She continued to drunkenly rant as her hands explored your body. “Oh, you look uncomfortable…I feel like…you got a little chub going on. Don’t push Mommy away…” She was sloppy as she stripped down, giggling and smiling stupidly as her head spun from the wine.
“How about you touch Mommy’s titties?” she slurred. “Look, Mommy got a new bra…” She shook her tits in you face, then insisted that you touch them. She went on to tell you about how lonely she had been, and all she wanted was to be touched.
Her hand wrapped around your stiff cock, and she could see the red on your cheeks from blushing. Eventually her warm, wet mouth would bob up and down on it, and she would beg for your throbbing cock inside of her. Her moans would be wild and loud, and after the two you came, she’d ask if she could lie in bed with you.
“Don’t worry, there’s room for us to snuggle together…” she’d tell you with a warm smile. “Good boy.” A few seconds later, she’d be fast asleep. What would she think when she woke up?Would she even remember what happened?

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

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MoRina – Helping Mommy Relax HD

Your mom just arrived home from work, wearing a pretty red blouse, short skirt and high heel pumps. She’s tired and her feet hurt, so you offer to massage them for her. She lies back on the couch and as you massage her feet you are surprised at how good it feels and how excited you are getting. Mommy’s short skirt is riding up and you can see her red panties and she can tell you are looking… Mom is starting to get worked up too, so she says she is going to change into something more comfortable. She returns wearing only her panties and a sheer robe that doesn’t seem to want to stay closed. As you continue the foot massage, your hands slowly drift to her wetness. The look on your mother’s face tells you what she wants, so you tenderly finger her to orgasm. After her orgasm, it seems like you’ve really helped mommy to relax… she’s glowing from that… um…. massage… (2 scenes, intimate and sensual solo video, POV, no male voice)

TABOO, POV, ORGASMS, OLDER WOMAN / YOUNGER MAN, MILF, MOMMAS BOY

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MoRina – Mommy Loves You

Have you had a stressful day? Having trouble getting to sleep? Mommy comes to tuck you in, and as always she has lots of positive affirmations for you. She’s so proud of you and thinks the world of you. There is no love greater than a mother’s love and you’ll always be momma’s boy, her little baby. She helps you to relax by talking softly and taking you through an anti-stress relaxation exercise. Night night sweetie! This is not a “taboo” video, it’s a sweet, loving video to help you feel good about yourself and get some rest! Watch it when you are lying in bed and suffering from insomnia, anxiety or your thoughts are racing and you just can’t settle down for the night.

MOMMAS BOY, MESMERIZE, LOVE ADDICTION, OLDER WOMAN / YOUNGER MAN, SLEEP FETISH, ASMR

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Fifi Foxx Fantasies – Ivy Secret & Sydney Paige – Aunt Guides Mom & Son Through a Sexual Experience, POV – Mom Confesses Her Loving & Sexual Feelings for Son – HD 1080p

It wasn’t okay…it wasn’t right, but she needed someone to confide in. “I’ve been having these feelings and they’re so wrong, so immoral…and it’s been giving me so much anxiety,” Mom said nervously to her sister. Although she reluctant at first, she finally confessed that she felt like she was in love with her son. “I’ve been having these sexual thoughts and feelings…and so much love and attraction and it’s all I can think about,” Mom explained to her. “I can’t even be around him because I just want to touch him and kiss him and do all these things…and it’s so wrong and it’s so gross. I don’t know how to get over it, I don’t know what to do…”
Yes, of course, it’s wasn’t normal, but Sydney did the best she could to make her sister feel better. “What we should do is find a solution,” she told her. “Maybe you should just do it…just do it once and maybe all these feelings will stop. If it’s stressing you out this much, it’s bad for your health.”
Mom was nervous, but Sydney promised to stay and guide her through everything. “Hey nephew,” Auntie called out to you. You entered the bedroom to see them sitting closely to one another. “I’m gonna let her do the talking…” Mom said shyly, “I’m feeling a little embarrassed and awkward.”
Auntie was blunt about everything. She told that Mom was attracted to you and the man that you had become. “And who could blame her…” Auntie tried to make things sound reasonable, “you are the spitting image of your father when he was younger – you look just like him.” And in order to help ease the stress of this awkward situation, Auntie suggested that maybe the two of you should have some intimate time together and get past this.
And, of course, no one would talk about this outside the family. It was only to help Mom get better. So, under Auntie’s watch and instruction, you and your mother began to experiment. You started off slow. First you and Mom would kiss, then you’d try longer, more passionate kisses. “That did feel kind of nice,” Mom blushed.
“Maybe we should take it a step further,” Auntie told her. “Um…maybe show off a little? I mean, you have a beautiful body.” Mom pulled down her lingerie and invited you to touch her big, perky tits. After that, Auntie told Mom to touch something of yours. The two of you went back and forth touching one another – groping, stroking, fingering, licking, sucking – until it was time to have sex. Mom didn’t want to feel too awkward, so she faced the other way and let you fuck her from behind.
After everything was finished, Auntie made sure the both of you were okay. Mom was still embarrassed, but she shyly mumbled, “Maybe can try it again sometime…just whenever I’m feeling stressed out…”

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

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Fifi Foxx Fantasies – Reagan Lush – Mom & Son Become Friends with Benefits, POV – HD 1080p

“Well sweetie, I wanted to talk to you before you have your game later tonight,” Mom said warmly, “and I was hoping you’d keep an open mind here…” She went on to explain that her and Dad were having some issues, and since he wasn’t around much because of work, that the both of you needed to be there for one another.
“You know I need you, sweetie,” she smiled, “you’re my one and only son. You’re the person I can count on…and let’s face it, you’re pretty much the man of the house now. You’re getting older, going on a lot of dates, have a lot of friends…but Mom really needs you now.” And because you were maturing, you were becoming more sexual, and there was no need to be shy about it. Your needs were becoming more drastic, you were jerking off more, and Mom didn’t want you to be afraid to talk to her about it.
“Now that I’m lonely all the time, I feel like we should be able to count on one another,” Mom caressed her inner thigh. And since you were going out on dates all the time, Mom figured you probably had had sex, too. “I feel like you and I should be able to talk about these things – have you ever heard of a friend with benefits? It’s not really a fuck buddy, I’m sure you’ve heard of that thing from your friends, but a friend with benefits is a lot closer…”
Mom went on to explain that a friend with benefits could be someone you were really close to, like her, that you could get sexual with, fool around with, have fun with – someone that could help you out before your big dates. “You think Mommy is sexy, don’t you? You like looking at Mommy, don’t you?” she asked seductively as she unbuttoned her pink blouse. “I mean, if you’re going to have a friend with benefits, it should be with me, shouldn’t it? You’re always looking at Mommy…you know this would be the perfect situation…I wouldn’t tell anybody…”

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

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Princess Ellie Idol – STEPMOM CONFESSES TO BLOWING ALL YOUR FRIENDS 1080p

I have a confession… You see, every time one of your friends comes over, I tell them to meet me in the bathroom so I can suck them off or give them a titjob. I’m just so horny with your dad away for work so much and there’s just something about teasing these hot younger inexperienced guys that really turns me on. Say, is this turning you on? Do you like hearing what I do to your friends? I think you do. I think you want your stepmother to take your virgin cock into her mouth and suck on it, huh? I can’t WAIT to corrupt you… Guys your age just can’t resist women my age because we know just how to take care of you. Then, when you finish in my mouth, I’ll swallow it down to hide the evidence…just like I did with all your friends before you. Don’t worry, we’ll keep this our dirty little secret. 😉

MILF, BLOW JOBS, CUM IN MOUTH, CUM SWALLOWERS, OLDER WOMAN / YOUNGER MAN, TABOO

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