Tag: MASTURBATION ENCOURAGEMENT

Its a Good Size Son – Bettie Bondage

So embarrassing. Your mother found the wrapper to these dick pills you were curious about, and now she wants to talk to you about it. First off, she thinks you used it with a girl…which you aren’t jumping to correct her on. Then, she wants to talk to you about penis size! Yeah, this won’t be awkward…
She reassures you that size doesn’t matter, that the average if 5.5″, that she’s sure you come up over that, considering your father…hmm. This talk is turning kind of interesting, made more so by her lowcut blouse and tight pencil skirt. Your mom has always been a total fox – your friends are all too happy to tell you this often, and you’ve always secretly agreed. Sitting across from you, she looks so sexy. You decide to push this, see where you can take it.
You tell her that you were using it on yourself, curious what it would do. You admit that you wonder often how you measure up, that you’re a bit preoccupied. You just don’t know! You’ve never shown it to a girl before…
She plays right into it, telling you that if it will quell your insecurities, she’d be happy to take a look and let you know. Before she can even finish telling you to take it out, you have your rock hard cock in hand, displayed for your mother. She gives you a timid but obviously impressed once over as you begin to stroke, not sure how she’ll react…her face blushes. She seems intrigued. You keep stroking, and she mentions the pill’s claim on stamina…
“Perhaps we should test that out too? How? Oh, you know…with my hand. Perfectly natural, totally not sexual. I’m your mother after all…”

Category: TABOO
Related Categories: MASTURBATION ENCOURAGEMENT, MILF, POV, CUM IN MOUTH, VIRTUAL SEX

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Happy Anniversary, Mom – Bettie Bondage

Your mom is always fighting with your father, even on their anniversary. He’s been cheating for years, but on their wedding anniversary? You walk in on her crying on the bed after hanging up on him. You tell her that you’ll stay in with her tonight, keep her company on her anniversary. She tells you that you don’t have to do that – so sweet of you, but she doesn’t want you staying out of pity. You reassure her that you’d love to stay. You can tell she needs you.
You talk about everything. Even things that you maybe shouldn’t. She tells you how scared she is of leaving your dad, how she doesn’t think she could find someone else. She doesn’t know if she could flirt or be sexy. You tell her what you’ve always thought, that she is sexy. She blushes and your eyes fall to her chest. She’s breathing a little more rapidly and her soft, pillowy breasts are nearly pouring out of her top. You get the urge to reach out and touch her but instead you just stare. She notices you, noticing her. Wanting her. She can tell you’re looking at her with lust and you can see a struggle rising in her eyes, whether she should act on these thoughts. You’re her son, after all…
When she finally reaches down and touches your hardness, you want to roll her over and mount her. Take her. Show her how sexy and wanted she still is, but she backs away immediately. It’s wrong, she insists. We can’t touch each other! She says. Well, what about if we don’t touch each other? Just watch?
You grin as your mother’s hand falls between her thighs and begins to rub over her white cotton panties, while you begin to stroke your cock. She’s gone, consumed by her lust for her own son, the second she starts to play with herself. You watch, stroking, as she takes her panties off and passes them to you, telling you to wrap them around your cock and jerk for her. You can smell her on them, feel her wetness. You can’t wait to cum all over your mother’s dirty, wet panties.

Category: TABOO
Related Categories: JERK OFF INSTRUCTION, MASTURBATION ENCOURAGEMENT, POV, ROLE PLAY, VIRTUAL SEX

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MOTHER LURED YOU INTO HER ARMS HD (MOTHER AND SON POV TABOO ROLE PLAY) – Raven

YOUR MOTHER ASKED FOR A FAVOR.SHE WANTED YOU TO TAKE SOME PHOTOS OF HER.SHE’S BEEN SINGLE FOR A WHILE NOW AND SHE DECIDED TO MAKE AN ONLINE DATING PROFILE,SO SHE NEEDED SOME NICE PHOTOS FOR HER PROFILE ALBUM.YOU FELT A BIT WEIRD ABOUT IT,BUT YOU COULDN’T SAY NO TO HER,YOU DIDN’T WANT TO DISAPPOINT HER.PHOTOGRAPHY IS YOUR HOBBY AND YOU HAVE A PROFESSIONAL CAMERA.YOU STARTED SNAPPING FIRST PHOTOS ,AND SHE POSED WITH A SMILE ON HER FACE.THEN SHE MOVED TO THE BED.SHE OPENED HER LONG CARDIGAN,REVEALING A SEXY ONE PIECE BODY SUIT.”DON’T WORRY, THIS PICS ARE FOR THE PRIVATE ALBUM,IT WON’T BE AVAILABLE TO EVERYONE”SHE SAID. IT DIDN’T MAKE YOU FEEL BETTER.YOU FELT UNCOMFORTABLE TAKING THAT KIND OF PHOTOS OF YOUR MOTHER,YOU NEVER SAW THAT SEXUAL SIDE OF HER.THERE WAS SOMETHING ELSE.YOU WERE JEALOUS.YOU DIDN’T KNOW WHY,BUT YOU WERE.SHE STARTED POSING IN A DIFFERENT WAY.SHE WAS SEDUCTIVE,SHE ACTED LIKE SHE’S FLIRTING WITH THE CAMERA.ONE OF THE STRAPS SLIPPED OF HER SHOULDER,REVELING HER NIPPLE.YOU FELT TOO UNCOMFORTABLE TO TELL HER,BUT SHE NOTICED,AND SHE DIDN’T CARE.SHE LET THE OTHER ONE SLIP TOO,REVEALING HER BIG BREASTS.”WHY DID YOU STOP?WHY ARE YOU JUST SITTING THERE”?SHE ASKED.YOU WERE SITTING FOR A GOOD REASON.TO HIDE IT.TO HIDE WHAT SHE’S DONE TO YOU.YOU WERE HARD.YOU GOT TURNED ON BY YOUR OWN MOTHER.YOU REALIZED WHY YOU’RE JEALOUS,YOU WANTED HER TO YOURSELF,YOU COULDN’T STAND A THOUGHT OF ANOTHER MAN TOUCHING HER. “GET UP AND CONTINUE,THIS PICS WILL BE FOR YOUR EYES ONLY.I WANT YOU TO GET UP,RIGHT NOW” YOU DID WHAT SHE ASKED YOU TO.YOU CONTINUED TAKING PHOTOS,WITH A HUGE BULGE PRESSING ON THE INSIDE OF YOUR PANTS.SHE UNBUTTONED THE BOTTOM PART AND STARTED RUBBING HERSELF.”DO YOU LIKE WHAT YOU SEE BABY?LOOK HOW WET I AM,YOU DID THAT TO ME.NOW I WANT YOU TO DO THE SAME.I WANT TO SEE WHAT I DID TO YOU.I WANT YOU TO PULL YOUR PANTS DOWN AND STROKE YOUR COCK WHILE I’M WATCHING AND RUBBING MY PUSSY” YOUR COCK WAS THROBBING,YOU GRABBED IT AND STARTED STROKING IT EAGERLY.SHE TILTED HER HEAD BACK,BREATHING HEAVILY,SPREADING HER LEGS WIDE OPEN,ASKING YOU TO COME CLOSER,TO GIVE IT TO HER,SHE NEEDED IT.SHE WANTED TO FEEL HER SONS HARD COCK SLIDING INTO HER WET PUSSY,AND YOU DID WHAT MOMMY ASKED YOU TO….

Category: TABOO
Related Categories: MOMMAS BOY, POV SEX, MILF, MASTURBATION ENCOURAGEMENT, ROLE PLAY

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Spying on mom AGAIN! – Lovely Lilith

Honey… what are you doing in here? Nothing? Why are you hiding on the other side of the bed? Does this have something to do with the shower the other day? It does?
Okay, honey. You know I said that was the only time. Why are you trying to sneak another peak? You like to see Mommy naked? I understand, but this has to stop.
I’ll let you stay in here and help me pick out a dress for my date, okay? But that’s it! No touching yourself either, promise?

Category: MILF
Related Categories: TABOO, MOMMAS BOY, JERK OFF INSTRUCTION, MASTURBATION ENCOURAGEMENT, MASTURBATION INSTRUCTION

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Primal’s Taboo Sex – Mom’s Fantasy – Krissy Lynn

Part One:
Your Mom comes in your room while you’re laying in bed. She wanted to check up on you. As she slowly climbs onto your bed, she asks if you were sleeping. Answering the question for you, she says she knows you weren’t. Her body language tells you she didn’t come in here just to tell you she knows you’re masturbating. She starts to slide the skinny straps from her shirt off of her shoulder, teasingly undressing herself in front of you. It becomes very clear to you that your mom wants to be with as close with her son as she an tonight.

Part Two:
As you are about to leave to catch the bus for school, your mom notices you have a “raging hard on”. Realizing you can’t leave the house like that, your mom takes care of you again, like she did the night before.

Category: TABOO
Related Categories: MILF, OLDER WOMAN / YOUNGER MAN, POV SEX, MASTURBATION ENCOURAGEMENT, MOMMAS BOY

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Mommy Is Going To Teach You Masterbation JOI – Raven Winter

What’s wrong with my sweet boy? You can tell Mommy anything. It’s personal and embarrassing, never feel that way in front of Mommy. Well what exactly is it? Girls? Really? Why? You want to have sex, Oh I understand my sweet boy. Have you ever tried masturbation? No, well my dear boy, Mommy is going to show you how to masturbate and encourage you to masturbate. I will have you start with removing your pants, and letting me see your penis. I am going to help you get a nice hard cock. I will tease you with my big boobs, and I will even show you how Mommy likes to masturbate. But most important I am here to show you and let you release your cum anywhere on Mommy’s body. Oh great job sweetie, you blew your load all over Mommy’s tits, what a mess you have made. Don’t you feel better?

Category: TABOO
Related Categories: JOI, MOMMAS BOY, MASTURBATION ENCOURAGEMENT, OLDER WOMAN / YOUNGER MAN, CUMSHOTS

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Mom Catches You Staring – Sarah Rae

You’re relaxing in the living room with your Mom while she’s reading a book. You try to focus on other things but you just can’t help starring at her cleavage. This afternoon she’s had it and has decided to confront you about it. She wants an explanation. Why are you always starring at her breasts and trying to catch glimpses of her naked around the house? Its wrong to have this sort of attraction for your mother. What’s the matter? Don’t you like the girls at school that are your own age? You tell her that the girls at school just aren’t as busty as her. You lover her big tits and they are giving you huge, painful boners all the time. Your Mom feels bad. She doesn’t want her son to be sexually frustrated. She decides to help you out and let you stroke to her, but only if you promise not to tell anyone. This will be just be your little secret between you and her. You agree and your Mom shows you the huge tits that you’ve been dying to see for soooo long.

Category: TABOO
Related Categories: BIG TITS, ROLE PLAY, DIRTY TALK, ALL NATURAL, MASTURBATION ENCOURAGEMENT

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Taboo Mom Natasha – Stepmother Approval

Comes to your room to console you. Telling you she understands and thinks what you are doing it completely ok, she leaves you to do your business…but you ask her to stay. She is so caring and that is exactly what you need right now. She shyly accepts and encourages you to masterbate in front of her,, telling you how normal and ok it is… you pump furiously and watch her reactions. Turns out evil stepmothers are just a myth.

Category: MILF
Related Categories: MASTURBATION ENCOURAGEMENT

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MOMMY DOESN’T MIND HD (MOTHER AND SON POV TABOO ROLE PLAY) – Raven

YOU WOKE UP HORNY, AND DECIDED TO JERK IT OFF UNDER THE SHOWER.WHILE WALKING TO THE BATHROOM,YOU HEARD THE WATER RUNNING AND SOMEONE SINGING.IT WAS YOUR MOTHER TAKING A SHOWER.YOU COULDN’T RESIST,YOU SNEAKED IN AND HID SO SHE COULDN’T SEE YOU WATCHING HER.SHE LOOKED SO BEAUTIFUL.THE WATER CARESSING AND RUNNING DOWN HER NAKED BODY,OVER HER BIG BREASTS AND DOWN HER LONG LEGS.YOU COULDN’T TAKE YOUR EYES OFF OF HER.SHE TURNED THE WATER OFF,READY TO GET OUT OF THE SHOWER.YOU KNEW IT’S DANGEROUS BUT YOU DID IT ANYWAY.YOU RAN INTO HER BEDROOM AND HID IN HER CLOSET.SHE WALKED IN A MINUTE AFTER YOU.SHE PICKED AND OIL AND SAT ON THE BED,WITH THE TOWEL WRAPPED AROUND HER BODY.SHE STARTED RUBBING THE OIL ON HER ARMS LETTING THE TOWEL FALL ON THE BED.AS SHE WAS RUBBING THE OIL ALL OVER HER BODY,YOU PULLED YOUR SHORTS DOWN AND STARTED STROKING YOUR COCK. SHE WAS RUBBING THE OIL ON HER THIGHS,HER HANDS FOUND THE WAY TO HER PUSSY.FOR A SECOND, IT SEEMED AS SHE LOOKED AT YOU,BUT SHE DIDN’T REACT.DID SHE NOT SEE YOU?OR COULD IT BE THAT SHE DIDN’T MIND?SHE TURNED TOWARDS THE CLOSET DOORS AND SPREAD HER LEGS.HER PUSSY GLISTENED WITH OIL AND HER WETNESS.YOUR COCK WAS THROBBING.
SHE LOOKED STRAIGHT AT YOU, “COME OUT BABY, I KNOW YOU’RE IN THERE.DON’T BE SCARED, I’M NOT ANGRY,MOMMY DOESN’T MIND YOU WATCHING”.YOU SLOWLY WALKED OUT,COVERING YOUR COCK WITH YOUR HANDS,EMBARRASSED YOU GOT CAUGHT,AND CONFUSED BY THE FACT SHE WASN’T ANGRY. “IT’S ALRIGHT, YOU’RE NOT A LITTLE BOY ANYMORE,I KNOW YOU HAVE NEEDS,AND I HAVE THEM TOO.MOVE YOUR HANDS,I WANT TO WATCH YOU.I WANT TO SEE YOU STROKING YOUR BIG HARD COCK FOR ME.” YOU LOOKED STRAIGHT INTO HER EYES AND MOVED YOUR HANDS SO SHE CAN SEE HOW HARD YOU ARE. “IT’S PERFECT BABY.NOW TAKE IT IN YOUR HAND AND STROKE IT FOR MOMMY,LET MOMMY WATCH YOU,LET MOMMY WATCH YOU STROKING THAT BIG HARD COCK” YOU NEVER FELT THAT WAY BEFORE,YOUR WHOLE BODY WAS SHAKING,YOUR HORMONES WERE RAGING.SHE SPREAD HER LEGS WIDER AND STARTED RUBBING HER SWOLLEN PUSSY. “CAN YOU CUM WITH ME BABY,I WANT US TO CUM TOGETHER” .SHE LEANED BACK,RUBBING HER PUSSY FASTER,MOANING,TILTING HER HEAD BACK.HER WHOLE BODY STARTED TREMBLING. “I’M CUMMING BABY,CUM WITH ME,CUM FOR MOMMY”.YOU SHOT YOUR LOAD ALL OVER THE FLOOR.IT WAS THE MOST INTENSE ORGASM YOU EVER HAD.

Category: TABOO
Related Categories: MILF, MOMMAS BOY, MASTURBATION ENCOURAGEMENT, VOYEUR, ROLE PLAY

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