Tag: MASTURBATION ENCOURAGEMENT

Cassandra Cain – Step-Mom JOI

Dad is coming home late again so stepmom finds a way to take up some time. She gets a naughty idea and starts flirting and suggesting we get a little closer. She wants to see what you’re working with so she entices you to pull out that cock and helps you get hard by showing herself off and pulling out her big tits. Just as she expected, you have a nice big cock. She starts encouraging you to jerk off to her, rubbing her tits and showing herself off more. Giving you JOI while she touches herself and showing her big round ass and taking off her panties. She shows you how to please a woman by masturbating and pulls out a vibrator. Mommy can’t take it any longer and has to cum. Jerk that cock for mommy and blow a big load.

TABOO, MOMMY ROLEPLAY, JOI, JERK OFF INSTRUCTION, MASTURBATION ENCOURAGEMENT

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Butt3rflyforu – Mommy Knows Best

You have been dating a girl from school and she is just a big tease and bitch that usually leaves you hard, sore and blue balls! Today is no different. You come running home with an aching hard on because your girlfriend was teasing you under the lunch table at school. Mommy knows exactly what is wrong. She just has to look in your pants to see your huge erection that can’t go down!!! Mommy tells you , “I told you to get rid of her”, “she never does anything good for you”!!!!! Mommy tells you to unzip your pants and let mommy work her magic because mommy knows best how to make that aching boner go away. Mommy turns on some sexy strip music and begins her erotic dance moves telling you to jerk your cock to her tight body and huge tits!!!You begin listening to her every word and slowly you start seeing precum dripping. Mommy shakes her big tits and lovely round ass right in your face and you feel like you are about to explode. Mommy gets on her knees and opens her mouth wide and you begin ejaculating right into mommy’s warm mouth. Her eyes open wide as you drain yourself and she swallows!!!! Now go back to school and stop talking to that girl!!!! Mommy knows best!

MILF, TABOO, STRIP TEASE, MASTURBATION ENCOURAGEMENT, CUM IN MOUTH

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Ashley Alban – Mom’s Eggs and Hams

This is a follow up to “Step-Mom Shows you her New Bikinis.” Your step-mom is making you breakfast while she explains that even though your dad is out of town, she has a lot to get done, and she wants you to focus on your own tasks. As she rambles on about what she needs to do, you can’t help but stare at her ass showing through her see-through leggings. She chides you for not listening and responding to her. After she gives you toast and scrambled eggs, she starts loading the dishwasher. You can’t even eat as you watch her bend over. She catches you staring and says that she doesn’t understand why you’re so obsessed with her butt (she knows why). Eventually she gets frustrated and gives you a full view of her booty, she even pulls down her leggings, and tells you to get an eye-full so you can focus for the rest of the day. She mentions that she made a mistake showing off her ass to you previously, and just because she let you fuck, doesn’t mean it can happen again. After, she walks into another room and you pull out your hard dick to start stroking to the memory of that ass. She walks back in and catches you. She decides that something needs to be done, and she tells you to meet her in her bedroom after you finish eating.
When you go into her room, she’s now wearing lingerie and a lace robe. She tells you that you’re not in trouble. She explains that since you are obsessed, she’ll fulfill your little fantasy one more time. She tells you to pull your dick out again, and she shows off her body. She mentions that she has a surprise, and when she bends over, you find out that she has a buttplug in. She says that she’s getting her ass ready so you can fuck it again and get everrrrryyyything out. You’re rock hard by now, so she gets on her knees and sucks your dick. Once your dick is lubed with her spit, she gets up, bends over the bed, removes the buttplug and tells you to slide your cock in. She gets into it and starts begging you to fuck her ass hard and drain your balls. You oblige and fill her asshole up with cum.

TABOO, ASS WORSHIP, BUTT PLUG, VIRTUAL SEX, ANAL, MASTURBATION ENCOURAGEMENT

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Goddess Tatum Kelly – Silky Slip Taboo Fantasy

Honey, what’s wrong? Mommy heard you crying in your room. Is it because my new boyfriend is in my bed right now? I know this is a difficult adjustment, but I promise you that he’s wonderful. You still look sad, which means Mommy is going to do something extra special for you. My boyfriend can wait. Right now, it’s all about you, honey. Do you see what I’m wearing? It’s a silky slip. Mommy is going to tease you with this slip and you’re going to jerk to me. I know how much you love stroking to my hot body so not only am I going to play with my slip, but I’m also going to take it off. There’s that smile! That’s what Mommy likes to see! Now get your dick in your hand and start stroking.

MOMMAS BOY, TABOO, SLIP FETISH, SILK & SATIN, MASTURBATION ENCOURAGEMENT, JERK OFF INSTRUCTION

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Daras Daily Taboo – Asking Step-Mom For Dick Size Advice

You’re coming to stay with me for one week! That’s such great news! Oh dear, it seems you always catch me when I’m still in my dressing gown. So, how are you? Yes, your Dad is at work today. It’s just the two of us.
Oh dear, is it ever hot out these days! So, you said there was something you wanted to talk to me about? What is it sweetie? You have another date? That’s wonderful! So, tell me then!
Honey, you don’t have a small dick, silly! Is this really what you wanted to tell me? Oh sweetheart, don’t worry!
Ok, I’ll tell you this, just to help you feel better… You’re dick is the nicest and biggest I’ve ever had. Yes, bigger than your dads! Remember when I helped you with your erection? I told you then too!
This is silly, oh dear, you’re showing it to me right now! Oh boy, this is getting out of hand. Oh yes, I’m looking at it. Yes, I do think about it all the time. You’re making me horny now, stop it! Is this all you wanted to know? Is your dick big enough? Yes, it is! And this girl you’re going on your date with is very lucky! And I’m a bit jealous, I hope she deserves you! Your dick is so nice, and it is bigger than your Dads. You like when I tell you that don’t you!
You’re making me really turned on… You know I have a hard time controlling my urges! You like mummy’s big tits? You don’t mind if I touch myself a little bit here, imagining that big dick? Can you imagine it? Putting it right between my bum cheeks? Oh hunny, look at what you’re making me do. Is this the kind of advice you wanted from me? Acting all crazy and horny in front of you! Oh yea? You want me to touch myself before you fuck me? Ok, look at this then.
Why don’t you put your dick right in front of me here. Let me show you how big it looks in my hands and between my boobs. That’s it, unzip your pants. mmm. I see you’re nice and hard already. Oh dear, I’m getting really flustered! I should cover up! I can’t help myself though! Your Dad’s not home for another hour or so, so lets make it quick!
See, look how big and hard you are? Do you believe me now? I bet this feels good baby, you like that? It’s so big hunny! Just a quick hand job ok? It feels so good in my hands! Lets put it between my boobs. Mmmm, good boy! You can always come to me for advice. I bet you’d love to cum all over mummy’s tits wouldn’t you? Oh good boy.
We should count you down because your dad will be home soon with his small little cock. You better cum soon! No honey, I told you, just a hand job today. But you can cum on mummy’s tits, ok? In a few seconds, not yet, just a little bit longer.
Ok baby, ready… 5, your dick is so big! …. 4, mmmm ….. 3 …….. Oh I’m gonna cum too baby!…. 2 ……..oh, oh , yesss … 1 … cum all over me! Cum on mummy’s tits! Mmmmm! Good boy! Keep cumming, lots and lots and lots of cum for me! Mmmm

TABOO, MASTURBATION ENCOURAGEMENT, VIRTUAL SEX, HANDJOBS, MILF, MOMMAS BOY

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Amedee Vause – Crazy Mother – Taboo, JOI

Hey, you just arrived from school, didn’t you? How was your day? Any news on marks, or that essay you had? Oh, that’s good! Wait, don’t go to your room, I wanted to ask something. I thought about it these past few months and didn’t find a suitable answer, maybe you can clarify that for me. You’re so hansome, and I’m not saying that because you’re my boy, but because you really are, handsome and attractive. Why don’t you get a girlfriend? You’re handsome enough, you’re not shy… Because I know that boys your age have… needs. And you have to take care of those needs properly, they are the signals your body gives to you, you can’t postpone them or ignore them! I’m asking all this because I saw you in the kitchen yesterday, and you, mister, had a… boner! I was not looking, but it was so visible through the fabric of your pants! And I get it, you are young, you have desires. Your kind of desires might not be the most ethical ones, but they’re natural, that what every psychologist will tell you. I know that you are thinking about the forbidden fruit and you can’t focus on anything else since. And I understand it, with boobs like mines, you don’t feel the need to approach girls. I understand you baby, that’s why I’m showing you my big boobs, but nothing more. You should take advantage of this unique situation and take care of that cock for Mommy, now you can see them full naked, you don’t need to peek when I change my clothes, huh? Go on, I won’t stop you, on the contrary, I’ll encourage you!

MASTURBATION INSTRUCTION, JERK OFF INSTRUCTION, TABOO, MASTURBATION ENCOURAGEMENT, MOMMAS BOY, BIG TITS

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MoRina – Mom’s Birthday Love

You love your mom and since it’s her birthday, you decided to give her a special gift – a sexy sheer bra and panty set. It’s an awkward moment when she opens it up, but your mom is always so appreciative of your heartfelt gifts. When you ask her to try it on for you, there’s more awkwardness and some nervous laughter. But when she realizes you are serious about wanting to see her in the sexy lingerie, you can tell she’s sort of getting turned on. She agrees to model the sexy lingerie for you as long as you turn around while she changes. She’s very hesitant about letting you see it on but definitely wants to hear what you think. When she spots the bulge in your pants she tells you something you never thought you’d hear your mom say, and goes back and forth between feeling like this is so wrong and being completely turned on by it. Enjoy the intimate journey as mother and son explore their fantasy of forbidden love.

TABOO, MASTURBATION ENCOURAGEMENT, MASTURBATION, MATURE, FANTASIES, MOMMAS BOY

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Miss Gia Love – Mommy wants to watch you Jerk it

Mommy knows yor secret. She’s heard yoru phone calls and all of the things you have said to your friends at school… like how much of a boner she gives you! It’s ok. It’s not your fault that you have a hot mom. In fact, she kinda likes that kind of attention, and that’s why she has made this video for you! She slowly strips down and reveals her sexy lingerie and teases you. Mommy encourages you to take your cock out and stroke for her. Don’t be so shy and embarassed. She wants watch you, it turns her on! She even pulls her tits out for you and spanks her ass! Now that really gets you going and leaking pre cum. Mommy love to watch you stroke, and she even gives you a cum countdown to let you know when she wants to watch you blow! Mommy knows best!

JOI, MASTURBATION ENCOURAGEMENT, JERKING OFF, MILF, MOMMY ROLEPLAY

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Goddess Tatum Kelly – Sexy Step-Mommy JOI

I am your Step-Mom and I love seeing you so hard for me, especially when I wear my pencil skirts. I know they’re your favorite! You know what’s even sexier? What’s UNDERNEATH my pencil skirt. Your biggest fantasy is to watch me walking around the house without any pants on because you love the way I look in my bra and panties. Today, I am wearing red, which is your favorite. I slowly slip off my pencil skirt and turtleneck to reveal what’s underneath, all while giving you very tantalizing jerk off instructions and teasing you with my sexy body. I tell you I am going to do chores and read you bed time stories in nothing but my bra and panties. You like that, don’t you? You’re really going to like the cum countdown at the end. I want you to blow your load to my sexy body, but only when I tell you to. Step-Mom knows best.

MOMMAS BOY, STRIP TEASE, JOI, CUM COUNTDOWN, JERK OFF INSTRUCTION, MASTURBATION ENCOURAGEMENT

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Ms Paris Rose – Study Hard for Mommy

Mommy has noticed that her son’s grades are slipping in school so she goes into his room to talk about it. After a few minutes she realizes that he is sexually frustrated and needs to get off. She strips down to expose her MILF tits to her son and gives him jerk off instruction till he blows his big load for Mommy.

MILF, TABOO, JERK OF INSTRUCTION, MASTURBATION ENCOURAGEMENT, MOMMY ROLEPLAY

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