Videos Tagged with jerk off encouragement

FionaDagger - Step-Sis Makes You Wear Her Panties 4

Mon 27 Jul 2026 08:37:06 +0200

You walk into your step-sister's room expecting to find her alone, but you're surprised and embarrassed to find her hot friend Amber is also there! Your step-sister asks if there's anything you wanted, and you immediately say no and start backing out of the room, but before you can escape your step-sis says she thought you were here for your daily wanking-whilst-wearing-her-panties session! You're so embarrassed to have your secrets spilled in front of Amber, who you have a huge crush on, but they both just giggle and inform you that Amber is already aware of your kinky little habit - in fact she's fascinated, and has brought her own panties for you to wear today! Your step-sister passes them to you and bullies you into putting them on, and the two of them giggle and tease you as they admire your hard cock in the little cotton pair of panties! Your step-sister tells you to go ahead and stroke yourself while they watch and enjoy, and the two of them take off their shirts to show you their breasts, and pull up their skirts to flash you their own panties whilst you jack it! After a while Amber whispers to your step-sister that she wants to rub your cock through your panties, and she moves closer to you to stroke your cock through the fabric while your step-sister watches in fascination! They both keep laughing and giggling, even as they give you lots of compliments and tell you how hot you look in your little panties, and Amber keeps rubbing your cock until you explode cum everywhere - even getting some on her hand, which she licks off! Your step-sister tells you that if you're good and you keep wearing panties every day from now on, she'll think about bringing round even more of her friends to have fun with you!

FionaDagger - Step-Sis Makes You Wear Her Panties

Mon 27 Jul 2026 07:56:08 +0200

Your step-sister catches you in her room, looking through her panty drawer!! She's shocked and immediately starts mocking you for being a gross little pervert, asking you what you do with them and imagining how you probably smell them and use them to jack off with! She decides to punish you by making you put on a pair of her panties, and laughs at how you look spilling out of the lacy fabric! You can't stop yourself from getting hard as she giggles and humiliates you, and when she notices she seems immediately turned on! She tries to hide it at first but asks you if you like how the knickers feel, and if you like wearing them for her... She apologises for getting so mad before, and even offers to show you some more of her collection, so you can see her model them! She tries on a few pairs, relaxing and getting more and more flirty each time she shows you a new pair or her panties - teasing you and even dirty talking about how you probably like being able to smell her cunt in her dirty knickers... She finally says that you look uncomfortable being so hard, and tells you to stick your hand into the panties and jack yourself off in front of her! She does the same and plays with her clit while you stroke your cock in your lacy little panties, and she even gets her tits out and laughs in your face when you can't look away from them! She bossily tells you to stroke your cock faster and faster, demanding to see you cum in the knickers! You release a huge load into the panties as she watches in fascination, then she informs you that from now on you're ONLY allowed to wear panties - no more men's underwear for you! She also tells you that from now on, you can only cum if you're doing it while she watches and while you're wearing your panties - AND, you're doing all the panty laundry from now on, hers as well, and you'd better start right now with the pair you just made messy, as step-mom and step-dad are going to be home any second!!

FionaDagger - Step-Sis Makes You Wear Her Panties 3

Mon 27 Jul 2026 07:46:10 +0200

Your step-parents have gone out and your step-sister is horny! She tells you she was shopping earlier and bought a cute new thong, and she can't wait to see you in it! She watches and giggles as you put it on, laughing at how your cock gets instantly hard. Then she surprises you by saying she wants to try jacking your cock for you! She reaches into your panties and starts stroking your cock, giggling at how weird it feels to be touching her step-brother's dick - but just as you're starting to get close she takes her hand away, saying she doesn't want you to get jizz on it! She tells you to start stroking it again, but gets hornier and hornier watching you, until just as you're about to cum she grabs your cock back and jacks it hard and fast everywhere; making you spurt all over her hand and all over your cute little thong!

FionaDagger - Step-Sis Makes You Wear Her Panties 2

Mon 27 Jul 2026 07:34:11 +0200

Ever since your step-sister caught you being weird with her panties, you've had a strict arrangement that whenever you need to masturbate you'll put on a pair of her panties and go ask her for permission! Today you tell her you're horny and need to jack off, so your step-sister inspects the panties you're wearing, teasing you for being such a horny little panty pervert, then instructs you to stroke your cock for her! She plays with her clit and keeps teasing and gently mocking you, taking off her top so you can admire her tits as you jack your cock. She makes you hold your cum until she says; making you desperate and horny until you beg her for release and she finally gives in and grants you her permission to cum - before reminding you of the rules and how you're not allowed to jack off by yourself anymore, so she's sure she'll see you and your panties again soon!

FionaDagger - Stroking It For Your Step-Aunt

Thu 25 Jun 2026 20:49:00 +0200

You're visiting your favorite step-aunt, and she's been feeling very concerned about how her step-sister, your step-mother, has been treating you lately!She knows that your step-mother has always been quite strict with you, but she's recently heard that you've been banned from closing your bedroom door, so you have no privacy, and that there's a lock on the internet so you can't watch any porn, and that you've just been banned outright from masturbating at all! Your step-aunt is horrified by this and tells you how she believes it's absolutely necessary for everybody to touch themselves regularly, but it's especially important for young men who risk getting backed up otherwise! You admit that it has been hard recently, and that you can't even remember the last time you were able to masturbate without getting caught. Your step-aunt thinks for a moment and then decides that clearly the best thing for you to do would be to take advantage of your time at her place, where your step-mother can't see what you're up to - so she thinks you should take this time to masturbate right now, so that you can at least go home feeling some relief! You're surprised and embarrassed at the suggestion but your step-aunt tries her best to make you feel comfortable with the idea, even offering to do the same herself, so that you can understand how natural and normal it all is. You shyly agree and your step-aunt begins to strip off her clothes, encouraging you to take your cock out and start stroking it. You can barely tear your eyes away from her as your step-aunt gets fully naked and begins fingering her wet pussy in front of you, as she talks softly to you and tells you just how you should be stroking it. She tells you that she expects you're desperate to cum quickly, as it's been so long, but she insists that you try and edge yourself as much as possible, so that you'll have a nice big orgasm and can go home to your step-mother with your balls really empty! You keep following her instructions until you're absolutely bursting and begging her to say you can cum, so your step-aunt gives in and allows you to shoot your load as soon as she herself cums! You jerk yourself quickly as she rubs her clit, and the two of you cum hard together! Your step-aunt asks if you feel better now, and tells you that you can come and visit her whenever you need to drain your balls!

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

Sun 11 Jan 2026 07:46:00 +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 06:01:07 +0200

Watch Kayla Kiss in I Forgot To Hang Up He Saw Everything Part 2. Cum get your fix of FREE family xxx porn videos only on tabootube.xxx.

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 17:35:00 +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 17:37:00 +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 03:40:06 +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

Mon 03 Nov 2025 18:20:05 +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!

NicoleBelle - You Are Mom's Pervert

Fri 25 Jul 2025 13:22:04 +0200

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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!