Videos Tagged with jerk off encouragement

Natalie Wonder - Uh Oh What’s Your Stinky Mom Gotten Herself Into Now

Sun 11 Jan 2026 15:02:05 +0200

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Oh sweetie what a long, hard day this has been for me. I had the great idea to start organizing the garage which turned into an all day decluttering session. I was in there for hours! I’m hot, sweaty and tired. Not once did you come down and ask if mommy needed any help. You were studying in your room all day, you say? Okay at least you were doing something productive. Proud of you.

Oh goodness I stink! Honey, trust me, you don’t want to get too close. Why do you seem so anxious? Everything ok? You feel anxious and stressed? Go masturbate. Always does the trick for me. So take mom’s advice, go to your room and jerk off. Sorry, you don’t want to hear me talk about this but I live in reality and want to give you helpful advice. I’m not embarrassed.

Why you still standing there? What does my pussy and ass smell like right now, you ask?!!! Sweetie! No I was not trying to talk dirty before it was only a suggestion. You’re curious as to what I smell like? Come take a whiff. I bet one sniff of my armpits will totally turn you off. You love it?!! Oh goodness, what have I gotten myself into.

Kayla Kiss – I Forgot To Hang Up He Saw Everything Part 2

Thu 08 Jan 2026 15:04:03 +0200

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Part 2

Features: taboo role-playing; older woman and younger man; outfit changes with dresses, heels, and a silky blue robe; flashing and teasing with the multiple views and angles in front of my mirror; dirty talking, peeping and voyeur fantasy.

This picks up where Part 1 left off! Your aunt has just found out that you have been watching her through the video call that she forgot to hang up. You overheard her fantasizing about all kinds of hot, dirty things that she wishes she could do with you. Your aunt wants to get you naked on her bed and ride your cock! But right now, the extreme look of embarrassment and fear on her face has you worried that you may have blown your chance to make that happen! Why hadn’t you just stayed quiet on the call? She would have never known you were still on and watching.

Your aunt tries her best to cover her curves and massive tits up with whatever she can find. And she scolds you for watching, grinning, and enjoying the show she was unknowingly putting on for you. But when she sees just how hard you are, she begins to forget her embarrassment and worry, and let’s her horny MILF hormones take over instead!

Your aunt decides to use this moment to put on a show for you that you will never forget. And she encourages you to touch yourself and have an orgasm while she watches! Watching an older, experienced woman touch herself while she enjoys the sight of your cock is driving you wild. Which part of this video call will make you blow your load? When your aunt climbs on top of her favorite thick sex toy? Or when she tells you that she wishes it was your cock she was riding every night!?

FionaDagger - Mom Makes You Eat Dads Cum Part 2

Sun 28 Dec 2025 14:59:04 +0200

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Your mom and dad recently decided that because you’re so pathetic and unmanly, you were going to start eating your dad’s cum out of your mom’s pussy every day, in the hope that that would let you absorb some of your father’s strong masculine energy, and help you become less of a loser! Today you’re ready to eat another load of cum from your mother’s pussy as she encourages you by telling you how much she loves you, and that she’s only making you do this because she wants the best for you, and wants to help you not be such a pathetic virgin loser anymore… Once you’ve cleaned that load up thoroughly your mom tells you that your father will be home from work in a little while and will probably want to rail her and give her another load at that point, so you should come upstairs to get another load of cum to eat once he’s home! But later, when you come up to your parents bedroom again, they instead inform you that they’ve decided to try making you eat it directly from the source instead – so straight from your dad’s cock! Your mom reassures you that there’s nothing gay about this, it’s purely to make you a more manly version of yourself, so you don’t need to worry! She makes you stick out your tongue and rest it under the head of your dad’s cock as she jacks his cock into your mouth, but soon decides that actually it will be much simpler if you suck it yourself (but remember, it’s not gay!) Under your mother’s close instructions you begin sucking your father’s large, manly cock, struggling to take it all into your mouth! Your parents can’t help but laugh and tease you about how pathetic you look right now, but remind you that even though this may be humiliating at the moment, it will all be worth it when it helps you grow your tiny cock bigger, and to become an impressive, strong figure of masculinity! Your mom makes you squeeze and then suck your dad’s balls, and then even makes you rim him and lick his asshole while they both giggle at how ridiculous you look! Your mother then tells you to get on with it and suck his cock properly, and it doesn’t take long for your dad to be cumming into your mouth – as your mom watches closely and commands you to hold it in your mouth, not to spit it out or swallow it just yet! She then makes you jerk yourself off as you hold your dad’s hot, salty load in your mouth – explaining that making yourself orgasm while you’ve got your dad’s cum in your mouth will surely increase the effects and make you manly even faster!!

FionaDagger - Mom’s Bisexual Encouragement Punishment

Thu 25 Dec 2025 14:24:03 +0200

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Your mom arrives home early and catches you and your friend in her bedroom, masturbating with her dirty panties! She’s horrified and starts laying into you and promising to inform your friend’s mother of this disgusting behavior, and then decides she’s going to punish you right here and now – and since you both seem to love masturbating so much, you can keep doing it – but you’ll be masturbating each other while she watches! She insists that you take back her dirty panties so you can both smell them as you stroke each other’s dicks, and berates and humiliates you as you both reluctantly jerk each other off! She informs your friend that she’s going to make sure his mother punishes him every day by making him suck and lick her dirty panties clean at the end of each night, and then wash them all by hand – and as for you, you’ll be cleaning your mom’s pussy out with your tongue every night – even after she’s let your father fill her up with spunk! She keeps making you stroke each other faster and faster, telling you both that if she catches you doing anything else like this ever again she’ll be making you suck each other’s cocks next time – and as you both get close to cumming, she warns you that the first one to cum is going to eat both loads off the floor! Your friend jacks your cock furiously to get you to cum first, and you can’t stop yourself shooting a load all over the carpet! Your friend starts cumming just after you, and your mother gleefully commands you to get on the floor and start licking up both loads before they stain her nice carpet!

Amber Hahn – Horny Mommy Needs Cunnilingus

Sat 29 Nov 2025 12:52:09 +0200

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Mommy needs some help!!! & you are the only man home ???? I have a very important evening.. I am not confident this is the right dress. I cannot zip it, my tits keep falling out, it is too short… can you see my ass? Do I look hot? Ugh..frankly, I am just horny and that is not the state I wanna be in, while going out tonight..Showing my hot body off to you, I can see you are hard.. I mean.. can we? should we? Maybe just a little bit? Make Mommy cum, baby.

AimeeWavesXXX - A Fertile Future with Mommy

Tue 04 Nov 2025 11:10:03 +0200

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Mommy thinks it’s time to take this relationship to the next level. After today, mommy wants you to breed her over and over and over again! She wants you to reproduce with her and keep her pregnant for years to come. Let’s do our part to repopulate the world!

Spunky Cat Has Intense Orgasm on Halloween

Fri 31 Oct 2025 13:34:08 +0200

NicoleBelle - You Are Mom's Pervert

Fri 25 Jul 2025 08:56:03 +0200

Watch NicoleBelle in You Are Mom's Pervert for Many Vids. Cum get your fix of FREE family xxx porn videos only on tabootube.xxx.

You are mom’s pervert

I am wearing a robe and suspender crotchless nylons No bra. No panties. My hair is in a bun and I have on glasses.

I am your mom waiting for your return. “Where have you been???”

As I listen to your explanation, I put my hands on my hips inside the robe exposing my bald pussy. I sit in a chair across from you so we can talk (Here I give accidental upskirt views of my bald pussy while we talk)

“The son I am mad at you is because our neighbor Mrs. Jones was over today looking for you. Her husband is out of town again this week, and she needs you to come over and fuck her in the ass again.” I am so angry!! I cant believe you! I have decided I am going to spank your bare ass” Drop your pants and lay over my lap”

I continue to scold you as I swat your ass I reach into the robe and rub my nipples as I continue swatting your ass

“Stand right now”. I make you stand, and I stand and open my robe then sit again for more swats I tweek and pinch my nipples to make them hard.

“Omg! This is disgusting! I can feel your hard on pressing against my thighs!” I am going to get rid of this hard on! STAND!

I make you stand, and I put both knees in the chair facing away from you..

“jerk off while you look at my butthole” (and I spread my cheeks)

“You are such a pervert! you want to look at your moms butthole!” (I continue scolding you) “Okey, this is not working to get rid of your hard on! I have the solution” (I am going to stick a dildo in my ass for you to watch) You are a pervert! Watching your step-mom fucking herself in the ass! I cant believe this is not working either!! Your cock is still hard! You are just going to have to fuck me in the ass! (While you fuck my ass) You are such a pervert! I need to cum —with your cock in my ass (as I rub myself to orgasm) Did you shoot your cum in Mrs Jones ass? You will do the same to me! I stand, straighten and close my robe, and tell you to go to your room. You are grounded!

Krissi Pookie - Sister's Slutty Diary

Sat 03 May 2025 05:14:03 +0200

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⋆˚✿˖° Your Sister's Slutty Diary ⋆˚✿˖°

In this video you're my brother. You have been reading my journal and I've caught on. You know you can't hide anything from your sis! The video opens up with me calling you into my room to confront you. I noticed it was out of place, and some pages were even folded down. The dirtiest pages. You deny it, but I wear you down until you confess to me. You admit to having read the dirty details of just how slutty your sister is. And you LOVE IT. I can see you're getting hard just thinking about it.

Today's your lucky day, bro! Get your cock out. Your sister is actually very curious... show me what you do when you read my journal? It's a JOI so I guide you a long a bit while you get lost in your sisters voice telling you how slutty she is in person. I show my tits and my hairy bush. I ask if you like what you see, but of course you do. I give you all the encouragement you need but since I'm a huge whore, I am getting so turned on seeing your cock and watching you stroke it for me. I tease you, and tell you what a perve you are for being so turned on by your sister and for getting off to merely reading her diary.

It's time to get serious. I come over to really help you out. I jerk you off, showing you exactly how your sister would do it. I even put it in my mouth. Before too long, you're getting the best blowjob, from your sister! I suck on your cock, continuously reminding you how perverted you are and how much of a cock hungry whore I am... Until you blow a huge load right on my tits!

⋆˚✿˖° Details // Themes ⋆˚✿˖°

It's me guys, of course it's taboo as fuck!

Miss Malorie Switch - Oily Step-Daughter

Sun 27 Apr 2025 04:47:03 +0200

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You creep in on your stepdaughter in the shower, watching her rub oil all over herself. You get hard and start stroking, but when she catches you, she quickly confronts you about it. She is shy, but she likes the idea of her stepdaddy stroking to her. She knows she should’ve moved out when she graduated, but she can’t help but stick around, especially with you now obsessed with your stepdaughter. Seeing her rub herself in oil, she urges you to continue for her. No touching, she says, but she encourages you as you stroke to her tight, oily body, thinking of how tight it must feel… She rubs herself all over until she cums, urging you to cum for her as well… Maybe next time, you two can do much more than just watch each other…

FionaDagger - Stroke It For Mommy's Tights

Wed 03 Jul 2024 18:51:06 +0200

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(This video is a bit cheaper because it’s shot on my phone rather than my filming camera!) Your mother has something to ask you… She’s been noticing that all her pairs of tights keep going missing, and she’s wondering if you have anything you need to tell her about it! She kindly explains that she won’t be angry, but she just wants you to be honest… Have you been taking them?? You shyly admit that you have, and your mother tells you that’s fine, she’s not mad, she just wants to know – is it a sex thing?? You’re very embarrassed but admit that it is, and that you have this weird complusion and can’t stop yourself from stealing her tights and using them to masturbate! Your mother says she suspected it was something like that, and that it’s totally fine and quite common for young men to become obsessed with their mothers in ways like this; but the thing is, she can’t have you continuing to steal her tights, as she needs them for work! She tells you that you can keep one pair to enjoy yourself with, but that she’ll need the rest back – and that in exchange, and to help you get over your obsession, once a week she’ll let you watch her modeling the tights for you, and you can wank off and try to get it all out of your system as much as possible. She strips off her skirt and gets you to drop your trousers, telling you not to be embarrassed and that masturbation is completely normal. She encourages you to stroke your cock as she shows off the tights for you, letting you have a good look at her legs, feet and ass encased in the shiny material. She gives you lots of gentle encouragement and kind words as she tells you how to stroke your cock, and when you warn her that you’re getting close she tells you it’s fine and to go ahead and cum while you’re admiring her tights!

Miss Malorie Switch – Your Pillow and Mommy

Wed 03 Jan 2024 02:25:11 +0200

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You walk in on your mom grinding against your pillow in your bed, and she is shocked when you find her. She apologizes, but once she notices how hard you are, she tells you to stroke while she finishes herself off. You watch, jerking to her as she grinds and rubs your pussy all over your pillow, marking it with her scent. Rubbing from the front and from the back, you get closer and closer, holding your orgasm for her until she cums. Finally, you let it all out, cumming for your own mother grinding into your pillow… She was going to change your pillowcase, but now I think it’s better if it stays on…