“So, here’s my son,” Mom introduced you to the blonde sitting beside her. “We’re interviewing her today, she might be your new sitter, honey.”
“He’s pretty calm during the day, if you can just stick on schedule,” Mom went on to explain. “The only thing I have is that he goes to sleep differently than most boys. If you don’t put him to sleep the right way, he has insomnia.”
“Do you rub his back or read him a book, give him warm milk?” the blonde asked. But you and Mommy had your very own special way of putting you to bed. First you’d take a shower to relax, then Mom would read you a bedtime story before you got your special massage.
“So, you have to comfortable with this…” Mom started to say, “and the reason why this pays really well is because some people would say no to it, but it’s the only way I can get him to calm down and go to sleep. We’ll start with a story, then I’ll rub his head, then eventually you have to be okay with jerking him off. Just gently rub on the top of his penis and then slowly jerk it off…”
“So here, we’ll show you,” Mom motioned for you to come over. “Go ahead and take off your pants. Good job. So, I just take my hand and jerk it off just like this. Doesn’t that feel good, honey?” Next, she’d have the blonde do the same thing and wrap her warm, soft hand around your pee-pee.
“Here, you wanna try? That way he gets used to you – that way we can see if he likes you or not,” Mom told her. “Twist it a little bit instead of just going up and down. He likes to be emptied out before he goes to bed. Do you like Sydney, honey? Do you like how pretty she is?”
Mom could tell how much you were starting to like the beautiful blonde, so she continued to show her more of the bedtime routine. “If he’s having a harder time going to bed, you can keep going more and more. What we’re trying to do is make him cum – if he doesn’t, he can’t go to sleep,” she explained.
So, Mom showed her how you liked having your pee-pee sucked, and then the babysitter did it next. And if you were still having trouble going to bed, there was another thing she could do to help you. “Are you okay with nudity? Because sometimes he’s more comfortable if he can suck on your tits and grab them,” she told the blonde.
Mom undressed, unfastened her bra, and let you suck on her perky tits. She’d then have the babysitter try it out. “And if he still hasn’t cum by now, we’ll have him fuck you,” Mom told her. “You’re on birth control, right? Okay, good.”
First you fucked Mom, then the blonde got fully undressed so you could put your pee-pee inside of her. The two encouraged you as you fucked the babysitter, and once you were ready, you exploded inside her tight, warm, wet pussy.
“Do we need to clean him up or anything?” the blonde asked, which impressed Mom. If the babysitter wanted to suck your cock clean, Mom promised a little extra pay. And just like that, you had a new babysitter. “I think she’s the one. Should we hire her?” Mom whispered with a smile on her face. “I’ll get the paperwork – she’ll be your new babysitter!”

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

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Your family loved traditions. Things like sitting by the fireplace right before opening Christmas presents, shopping for lights, drinking hot cocoa, and wearing matching pajamas. It was a special, fun way to bond, and you had grown used to those things growing up.
“Now we know you’re very young and it’s still a few years before you hit puberty…” Mom went on to explain, “but in our family, we like to start things a little early.” It was another family tradition, Auntie Carmen told you, and it would also serve as a learning experience.
“A coming of…maturity,” Mom told you. “See, our dad, he was a very traditional man…and although we weren’t always in agreement with it, Mom told us that one day he would come in and set forth the steps for us to become a woman.”
“He would show us what it would be like to be in bed with the opposite sex,” Auntie went on to say. “And what better way to learn than with someone you love dearly like your mom and auntie?”
Mom and Auntie explained that their father took their virginities, and continued to have sex with them from there on out. Sometimes it hurt and sometimes they didn’t want to do it, but they understood it was family tradition. “So, the good thing is that you don’t have to suffer through that hurting,” Mom comforted you, “unless you have a daughter…but that’s a different story, we would help you through that.”
“See, our dad was a little more forceful, he didn’t have patience…” Mom explained. “I don’t want that for you. I want you to see how enjoyable and awesome it is – it’s all through love.” You couldn’t say no to this tradition, it would upset Mom. It had been running in the family for years, and now it was her turn to pass it down to you. Auntie would assist her just in case you were a little shy or uncomfortable.
Mommy would start off by touching your pee-pee while Auntie undressed. “That way you don’t feel so embarrassed about this…” Auntie told you. “I’ll show you all of my stuff if you show me all of your stuff.”
Mommy and Auntie went back and forth taking care of you while you groped their beautiful, mature bodies. They then put your pee-pee inside their wet, warm mouths as they comforted you. Once they had you erect, Mommy put your pee-pee inside of her to get it wet, then let Aunt Carmen fuck you first.
It was very important in family tradition that you cum inside Mom, so she went next. “You did a good job, honey,” Auntie smiled at you. “And we can show you so many more techniques and ways so you’re prepared when you meet that right girl…”
“And if you don’t meet that right girl,” Mom said quickly, “Mommy and Auntie will always take care of you – we’ll make sure you’re never lonely…”

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

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Warning – this is an EXTREME taboo clip. One of my favorites!
“Oh, he’s so cute…I got him this set,” Mom smiled at your aunt. “We’re going to play a really fun game,” Auntie went on to tell you.
You had been wanting a doctor play set for so long, and now Mom finally gotten one for you! “I thought me and Aunt Carmen could have the same one…” Mom said cheerfully, “totally cool, huh?!” To start things off, Auntie wanted you take off your shirt so she could hear your heartbeat.
“Yes, just like at the doctor’s office!” Mom told you, then let out a little sneeze. “Oh no, you’re going to have to check me! I think Aunt Carmen should teach you how to use those tools.”
All of this seemed so exciting and fun to you, but what you didn’t know was that Mommy and Auntie had an ulterior motive. “You know, sometimes this is too tight,” Mom said taking off her bra. “You know at the doctor’s office how they make you wear that gown? That’s so you don’t have any stuff covering you up.”
“I think we can hear Mommy’s heartbeat much better without clothes on,” Auntie explained. Mom continued to take deep breaths as Auntie moved the stethoscope on different areas of Mommy’s chest, including her nipples, which you didn’t even you could do!
“Did you know, sweetie, that there’s a heartbeat all along the entire human body? Because the b1ood pulsates through arteries, which run all over our body!” Mom told you. “So, let’s see if we can hear my heartbeat from all the way down there…” Auntie pressed the instrument against Mommy’s panties and told her to breathe in.
Once you were finished with Mommy, it was Auntie’s turn. After you finished checking her, Mommy and Auntie wanted to check your whole body. They first listened to your heartbeat, then checked your little wee-wee. “See, the doctor has to check everything,” Mommy told you. “We have to make sure you’re healthy,” Auntie said.
Auntie then had to touch and pull on your pee-pee to make sure everything felt right. “It’s very firm,” she told you, “and it feels good, you’re very healthy.” And since Mommy was feeling a little warm, she needed you to check her temperature, but the thermometer needed to go in a very special spot.
“And since we can’t stick one of these in your special spot,” Mom went on to explain, “if we put your wee-wee in our mouths, that’s the best way a mommy and an aunt can tell if you have a fever.” If your pee-pee was warm in their mouths, they could tell whether or not you were sick.
So, Mommy checked first, putting your little pee-pee in her wet, warm mouth, then Auntie went next. After inspecting your private area, you needed to learn how to inspect theirs, so Auntie taught you how to use a doctor instrument to check Mommy. Of course, they also taught you to put a finger inside to feel for anything, too.
“Oh, that feels really good, sweetie,” Mommy said as she made funny sounds you had never heard before. Auntie said you were making Mommy feel a lot better. “You know how else you can check someone else’s temperature and see if they’re feeling good? Is if you stick your wee-wee inside of them…”
So, you put your wee-wee into Auntie’s special spot and Mommy listened to her heartbeat. Next, you put it inside of Mommy, and Auntie made sure that Mommy was okay, too. Something eventually spilled out of your pee-pee, but Mommy and Auntie said it was okay – it was a special medicine that they both needed to swallow.

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

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“Sweetie, you have to get your grades up,” Mom said to your sister. “If they don’t get any better, I can’t let you do any of the fun stuff.” As the two continued their important conversation, you barged into the bedroom with your new magic remote control.
“Honey, why don’t go into your room? We’re talking about something important right now,” Mom turned towards you in frustration. “I know…it’s the remote, go put it back near the TV.” Of course it was easy to mistake it as a remote to something else, but that’s what made it so appealing to you – they had no idea what it could do.
So, you showed them. With the push of a button, your mom and sister started saying naughty, sexual things. “I wanna fuck your cock so bad,” Mom said seductively, then gasped in horror. Anastasia gave you a sweet smile, then purred, “Yeah, bro. You wanna have some nasty, dirty sluts?” The two were shocked and confused at the words coming from their mouths.
“What just happened?” Mom asked you. But you ignored her question, pressing one button after another, and making them do whatever you wanted. The next command had them stripping uncontrollably in front of you. Their bodies were nude and exposed, and Mom desperately tried to cover up your sister’s body, but it was no use.
“Stop that!” Mom yelled at Anastasia as she stripped down. “Mom, I can’t!” Anastasia panicked. Their hands caressed their naked bodies, and Mom reminded you that you shouldn’t be looking at her and your sister that way. But things would only get worse for them.
Another button forced them to masturbate and moan in front of you. “No, no, no…” Mom screamed as her fingers circled her clit. “Get him out of here!” Anastasia begged your mom, but there was nothing she could do.
The next command pushed their bodies forward, and they were forced to wrap their hands around your throbbing, hard cock. “Don’t make me…I don’t want to touch your dick. Put that back in!” Mom told you. “Stop it, please…honey, please stop! You’re gonna be so grounded. Make us stop doing this!”
But no matter how much they begged, screamed, or threatened you, you knew you had total control of them. Another button, and Mom and Anastasia would be sucking your dick. “What’s wrong with you?!” your sister’s blue eyes widened. “You’re making Mom suck your dick?!” The two choked and gagged on your cock, and when they tried to pull their heads back, their mouths only magnetized back onto your cock.
Now it was going to get really fun. With another button, the two lied back onto the bed. They couldn’t move from the position they were in, so it made it ridiculously easy to penetrate their pretty, pink pussies. “Get out!” Anastasia yelled as she watched you fuck Mom. “You’re so gross!”
“Please stop!” Mom cried, but you didn’t. “Honey, why are you doing this!?” After you were satisfied, you moved over to your sister and began fucking her. She cried as you thrusted in and out of her, and your mom begged you to stop. And you did, eventually, when you were finished.
Your sister made such a disgusted face when she felt your cum inside of her. “Ew, get out of me!” she whined. Fortunately for you, the two were stuck in those positions until you were ready to let them go. You taunted them with the remote, then left them there hopeless and violated.

MAGIC CONTROL, FEMALE TRAINING, WOMAN FOLLOWING ORDERS, TABOO, EMBARRASSED NAKED FEMALE, VIRTUAL SEX

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A sweet taboo fantasy where mom and son become closer as they share their firsts for the New Year. A highly recommended clip.
“Honey, honey…it’s almost countdown time!” Mom said cheerfully. “I can’t wait to see the fireworks!” She counted down with the TV, then smiled at the huge display of fireworks on the screen. “You need to give Mommy a kiss! Kiss Mommy for New Year’s! You always have to kiss someone on New Year’s,” she exclaimed.
She leaned in to give you a peck on the lips, then pulled back with utter excitement. “Yay! I’m so glad I get to spend it with you! Look at all those fireworks – they’re gorgeous!” she smiled. “Oh honey, you know I love hanging out with you – give Mommy another kiss.” This time the peck was a little longer, but she still wanted more. “Let’s make this one longer,” she said leaning in then pulling back with rosy red cheeks. “You like kissing Mommy? I like kissing you!”
“Come on – one more, let’s make this one even longer,” Mom said and this time it seemed like she was almost making out with you. “I love those soft lips of yours!” She was thrilled to see that you had gotten excited from kissing her. “You’re so hard – did Mommy excite you?” she asked. She wanted to take care of your erection, so she motioned for you to come closer, and then wrapped her soft hand around your cock.
“I have a little question for you…” she began to say, “You know, Mommy just loves you so much, and I know you love Mommy so much, too, and I was wondering if you wanted to be Mommy’s first for the New Year, and Mommy will be your first…do you wanna fuck Mommy?” she asked sweetly. “You know I love you, honey, I wanna make you happy.”

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

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You never imagined something so embarrassing would ever happen to you. While everyone was out, you had pulled out a dirty, adult magazine and one of Mom’s lacy bras to jerk off to. However, in the middle of pleasuring yourself, Mom and Auntie barged into your bedroom.
“Hey honey, we just got a bunch of groceries and…” Mom started to say, but it was interrupted with Aunt Carmen’s horrified gasp. “Do you see what he’s doing right now?!” her eyes nervously shifted away from your hard cock. “I’m so sorry, honey,” Mom said sympathetically, and you rushed to throw her bra underneath the bed.
“Was that my bra?” Mom asked. “Honey, what were you looking at? It’s okay, it’s perfectly natural.” They picked up your magazine and began flipping through the pages to see what was so intriguing to you. “Oh, someone looks older women…” Aunt Carmen smiled. “Look at this!”
“Honey, why don’t you talk to me about these things?” Mom asked. “You know I’m the cool mom.” They tried to find the page you had been jacking off to, and once they did, they turned it towards you. “You like blondes like your mommy, don’t you?” Auntie teased.
Mom grabbed her bra from underneath your bed. “You know, I was looking for this today, I went out completely topless. Oh, you’ve seen them before – you quit your blushing!” Auntie teased that you had sucked them when you were younger, which only made your face hotter.
“I can’t have my sweet, young man with blue balls – they hurt so bad from what I hear,” Mom began to say. “Just let Mommy give it a little stroke… See, there’s nothing to be ashamed of, sweetheart.” Auntie soon joined in to help, and the two shared your throbbing cock.
They stripped down and let you lick and suck on their beautiful, perky tits, then wrapped their warm, wet mouths around your cock. While Auntie sucked you, Mommy pulled out your magazine and showed off all the pretty women that you liked to jerk off to.
Mom and Auntie then took your cock inside their tight, pretty pussies, letting you fuck them until you came. “Well, we’ll let you be…you can have your naughty, little magazine, but when you get horny again, you better knock on Mommy’s door,” Auntie told you. “You pinky swear, right?” Mommy held out her finger.
“Don’t tell anyone…” Auntie whispered.

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

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When you got home, Mom and Aunt Whitney were waiting for you in your room. “Hey honey,” Mom said cheerfully, “I’m so happy for you today – it’s your birthday!” Because you were getting older and becoming more interested in girls, Mom wanted to give you an extra special present this year.
“Look at his eyes already gawking at my tits,” Auntie smiled. “See, somebody is very interested in girls, isn’t he?” Your eyes scanned their gorgeous, mature bodies that peaked through the revealing lingerie they had on. Mom wanted to make sure to give you a memorable gift…a learning experience. “For your birthday present, you get to play with us,” she told you.
“You get to have your very first sexual experience as a threesome with the two most loving women in your life,” Auntie went on to say. You wouldn’t have to worry about anything; Mom and Auntie would guide you through the whole thing so you could enjoy yourself.
They kissed you, then slowly stripped down, letting you enjoy, grope, and suck on their perky, pretty tits. “How about a double handjob from Mommy and Aunt Whitney?” Auntie giggled. “Oh, he’s loving this right now…” Their soft hands stroked your cock, then they proceed to share it with their wet, warm mouths.
Once they felt you were throbbing hard, they laid back and let you fuck them. Mommy wanted you to start with Aunt Whitney first, that way you could finish inside of her. “Good job, honey…” Mommy moaned, “you filled me up. Now go get cleaned up and ready for your birthday party.”
“How does it feel to not be a virgin anymore?” Auntie smiled, her fingers circling her clit. It was the best birthday present ever…and Mommy and Auntie reminded you to keep it all a secret.

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

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Warning: this is an EXTREME taboo clip…one where you get to drunkenly take advantage of your poor mother…
It was late and her son still wasn’t home. “Hey honey…” she called him, “what time are you going to be home? Are you at a party? Can you please come home…you’re not supposed to be out that late. And please don’t drink, you know how you are when you start drinking…”
But Mom could already hear the slur in her son’s voice and that made her nervous. He hung up on her, and as anxious as she was, she tried to get some sleep. A few hours later, Mom woke up to her son slamming against the walls of her bedroom.
“Honey, go back to your room…you’re really wasted right now,” she said uncomfortably, her eyes wide and scared. “I don’t like it when you’re wasted – you know how you behave. No, don’t touch me…” She pushed him off of her several times, but he was relentless.
“Stop it, you’re not supposed to touch me!” her teeth clenched. “Don’t do it again!” She screamed and begged for him to go back to his room, but things only progressed. He pulled at her lacy lingerie, then groped at her beautiful, mature body.
“Honey, I don’t want you to do this…please…what do you want me to do so you don’t have to do this? You can hang out with your friends anytime you want, just please…” her voice was desperate and shaky. She knew what was about to happen…it had happened countless times before when he was intoxicated, and there was never anything she could do to make it stop.
“Don’t do this…” she cried. “You know this is wrong, you know you’re not supposed to be doing this. Go sober up, okay? You don’t want to do this.” But he fingered her and flicked his warm, wet, sloppy tongue against her clit as she sobbed.
“Get off of me…this is wrong,” Mom told him, but he continued to penetrate her tight pussy. He was far stronger than she was, so there was no use in fighting him like she had done in the past – she had to take it until he was done.
“Please go…please go…go away,” she begged, her pussy full of his cum. He got up, slamming against the walls, and headed back to his room.

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

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You didn’t know else what to do. You barged into your mom’s bedroom and her hazel eyes widened. “Honey, are you okay?” she asked. “Me and your auntie are talking about what we’re going to do today.”
Okay, this just got a million times worse – you had no idea your aunt was in the house. “Oh my god, I’m so sorry,” Mom’s face flushed red with embarrassment. “Oh no, it’s fine…it’s only natural,” your aunt smiled at her.
The problem? You had a huge erection that wouldn’t go down, and now the both of them saw it clear as day. You had a big date later that night, so you decided to pop a couple of Dad’s Viagra to make sure everything would work “down there.”
“I haven’t seen a cock that hard since I was a t3enager,” your aunt said. Mom gave her a little nudge and giggled, “Oh, stop it!” Although it was a terribly embarrassing situation for you, your mom and aunt were doing the best they could to lighten up the mood “Honey, Mommy and Auntie can help you with this problem before you go on your date. No need to worry,” Mom comforted you. “Next time let me know before you steal your dad’s Viagra – what’s wrong with you?!”
They explained that you were far too young for that sort of thing, and at your age, all you had to do was thing of something and you’d have a boner. “You were too nervous, weren’t you?” Mom asked. “That’s okay, I understand.” Auntie chimed in that she understood you just wanted to impress the girl, and that she loved seeing guys get rock hard for her when she was your age.
“Okay, so your date is in how long?” Mom asked. “An hour?! The only way we can help you is by having you cum. Don’t worry, we won’t tell anyone.” Your aunt smiled sweetly, “We’re all family.” Without hesitation, your mom and aunt pulled out their perky tits and encouraged you to play with them. You were allowed to grope, lick, suck – whatever you needed to do to cum.
“Don’t freak out, Mommy’s gonna take off her shorts,” Mom said, then began stripping down with your aunt. “Come over here and Mommy’s gonna suck you nice and good.” She wrapped her warm mouth around your hard cock and your aunt joined in. They shared your cock, then laid back on the bed for you to use their pussies. “You know what you’re gonna do with your girlfriend tonight? You’re gonna do that with Mommy…” Mom said, “and it’ll be good practice.”
“That’s right, just put your cock inside of Mommy,” Auntie said seductively. “I had no idea he had such a big cock,” Mom smiled. “Oh, it’s bigger than your dad’s.” You fucked your mom first, then moved over to your aunt’s sweet, pink pussy. They encouraged you to cum inside your aunt. “Fill me up,” she told you.
You finally shot a huge load of cum inside your aunt’s pussy. “You know Mommy and Auntie will always help you out. Look, your boner’s going down!” Mom said excitedly. “We told you we’d help you out. Now…go have fun on your date, honey!”

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

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A beautiful, passionate, intimate, secret relationship with your mom…your night time lover.
The two of you had fallen in love. Mom would sneak into your room while Dad was asleep, and you’d have another night filled with passionate, intimate, wild love making. “Oh, I just needed to sleep with you tonight,” Mom whispered sweetly, “you know how much I love you.”
Mom slid her beautiful, mature body besides yours on the bed, then looked at you adoringly. “Come over here,” she smiled putting a finger up to her lips, “but don’t talk loud…shhh.” She asked if you had missed her, then confessed that she had been thinking about you all day long. “I just wanted to kiss you and hug you,” she said. “Too bad we can’t tell anybody what we’re doing.”
That was the hard part. You wanted the world to know how much the both you were in love, but you knew they wouldn’t accept it. Dad could never know. “But every night, you can show me how much you love me,” Mom went on to say, “and I’ll show you how much I love you.” She asked if you missed kissing her, if you had thought about her while you were at school.
“I just wanna be with you all the time,” she said. “If it wasn’t for me being with your father, we could move somewhere far away and be together and no one would care. I love you so much, babe. Wanna come over and kiss Mommy?” She leaned in to give you sweet, passionate kisses, then pulled back to show off her red lingerie set that she wore just for you.
Mom loved the way you made her feel beautiful – the way your cock would throb for her body. She wanted you to touch her again, to make love to her. Her warm, wet mouth wrapped around your hard cock, and before you knew it, the two of you were sharing another incredible night together.
“You know Mommy knows how to make you happy,” she flirted. After the both of you had orgasmed, Mom laid beside you with an enormous smile. “I love you so much. Let’s cuddle, and then I gotta go back to Daddy’s room, okay? I’ll cuddle with you until you fall asleep.” She nuzzled her head into the pillow, her naked body against yours, and the both of you closed your eyes.

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

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