“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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“I love you so much,” Aunt Sydney whispered passionately, her lips pressing against her sister’s. The two siblings had been involved in a secret affair for a while now, and Mom was eager to spice things up.
“My son’s old enough now…maybe we should bring him in,” she told her blonde sister. “Maybe he’ll be okay with it, we’ll just have to make him feel comfortable.” It was best to keep their love a secret, and to keep things in the family.
Mom called out for you. When you entered the room, you were surprised to not only see your mom and aunt in lingerie, but to see them being intimate with one another. “I know this is a little bit of a shock to you,” she began to say, “but your aunt and I have been in a relationship for quite some time. We’re very much in love, but it’s still a secret, we’re not telling anyone – not your uncle, not your father…”
“We were thinking that, since you’re old enough now, maybe it’s time that you join us,” she said sweetly. “I know it sounds a little strange, but we just want to show you that it’s okay, that you can be comfortable and you can enjoy it.”
“And it would make for good practice,” Auntie turned towards her sister. “He could use some tutoring from some older, more experienced women who are very sensual and loving with each other.”
Although their love was forbidden, they wanted you to accept it and to give into it – they wanted to share it with you. They kissed one another in front of you for the first time, then Mom suggested you give Auntie a kiss. “It’s important for you to experience all this love,” Mom smiled, her arms wrapped around her sister’s naked body.
You shared their passion, intimacy, and love. You kissed Mom and Auntie, then touched their beautiful, mature, soft bodies. Their hands and mouths shared your throbbing, hard cock, and they moaned softly as your tongue flicked against their pink pussies.
Everything was so intense, emotional, genuine, and heartfelt. Their sweet smiles expressed how truly happy they were. You then made sweet love to the both of them as they held one another. “That is so hot…” Mom said looking down at her sister’s cum-filled pussy.
You had never felt such raw, pure love before. Forbidden family love was the best love of all…

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

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Mom was a fitness fanatic. She was always getting up early to run and to work out, so when you came into her room, you weren’t surprised to see her stretching out. “Oh hey, sweetie,” she looked up to see you standing in front of her. “I actually wanted to talk to you about something. Do you mind sitting down for a minute?”
Mom explained how important it was for her to stay healthy and in shape, and how she really needed to work out to do that. Things around the house, however, caused her to be a lot busier, so she wasn’t getting as much time as she wanted at the gym.
“So, here me out…this is going to sound a little weird,” she went on to say, “but sex burns a lot of calories, and it burns them really quickly. It’s basically like a high intensity work-out. Do you know what that is? It’s when you work out really, really hard for a short amount of time instead of moderately for a long amount of time.”
Because of that, Mom felt it’d be a super effective work-out, one that was great for her heart and for her body. “So, what would you think about helping me with that?” she asked. “No, not helping me find someone – I mean you helping me. Like you having sex with me for my work-outs so that I can have a little more time to do other things.”
You wanted to help Mom, but it was awkward. “Let me just get you a little warmed up to the idea,” she said sensing your hesitation. “See, Mommy’s got to stay in shape, and don’t you love looking at a body like that? A nice, fit body…”
“Oh, I can see you do,” she smiled. “Well, let me show you how we can incorporate this kind of work-out. See? I can pull these down, and instead of lifting barbells, I can just stroke your cock like that, and see how it’s working my arms and shoulders? I can already feel the burn. Thank you so much, honey, you’re such a great help.”
Mom continued to work out both of her arms by stroking your cock, then positioned herself to where she could suck your cock and get her exercise. Once she was satisfied with that, she stripped the rest of her clothing off, then laid back for you to penetrate her.
While you fucked her, she wanted you to lift up her body to work out her glutes. “See? It feels so good and I feel the exercise in my back,” she moaned. “This is taking hardly any time at all! Doesn’t that feel good, sweetie?” After that, she had you lie down so you could ride you.
“See, by just bouncing up and down on your cock, I’m getting my legs nice and strong,” she said as she fucked you. “And this is a class that never gets boring! And finally, we can work our cores…that’s right, just swivel, keep that core engaged.”
“Well done!” she fanned herself off. “That was quite the work-out. Thank you! I’m going to feel this in the morning…”

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

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“Honey, I am so proud of you for getting straight A’s this time,” Mom said cheerfully. “I knew you could do it! I know I’ve been giving you rewards every time you do good, and since you got straight A’s, I thought we just needed to go really big.”
“It’s me!” Auntie threw her arms into the air excitedly. “And me! The both of us!” Mom chimed in. It had been a while ago since Mom started the new “reward” system. As a motivation to do better in school, she had shown you her body, then let you touch it, lick it, and fuck it. Every time you improved your grades, she upped the prizes to something better, and this time she had given you the ultimate reward – her and your aunt.
“We are so proud of you,” Auntie said with a big, happy smile, “you’ve been doing so well.” And when Mom had told her about the reward system and how well it was working, your aunt jumped right in to help. “You’re going to be a doctor one day,” Auntie said confidently.
“I will do whatever works…” Mom told her sister, “whatever works.” To begin your reward, Auntie helped Mom undress, then Mom helped her. You had never seen your aunt’s body exposed before, but it was just as beautiful and perfect as you had envisioned it would be. “Do you like that, honey?” Mom asked after she shared a kiss with your aunt.
“Is he going to be able to concentrate in class, or is he going to be thinking about this?” Auntie joked as her fingers brushed against Mom’s soft body. “It’ll drive him to work harder…it’s been working so far,” Mom giggled. After undressing, Mom wanted to take things slow, so she started you off with a little show. Her and Auntie would masturbate and moan in front of you to excite you and get you throbbing hard.
“Isn’t her pussy so beautiful?” Auntie said seductively. “No wonder he’s doing so well in female anatomy…” After warming you up, Auntie pulled down your pants and started stroking your cock. “Auntie’s got a big, fat cock in her hand…” she purred as she jerked you off, now sharing your cock with Mom.
“He’s so excited…” Mom said sweetly as she watched pre-cum ooze from your cock. “Look at my tits, baby, while your mom sucks your cock,” Auntie told you. They shared your cock, flicking their tongues against your shaft, then wrapping their wet, warm mouths over the head of your cock. “So, which one of us should he take first?” Auntie asked your mom.
Auntie then proceeded to get on all fours so you could fuck her from behind first. After that, you moved over to Mom, and fucked her until you finished inside. “Oh my god, I can feel how big of a load it is…” Mom said in-between breaths. “It’s dripping out of you,” Auntie looked down at Mom’s cum-filled pussy. “Yeah, so just keep those grades up, nephew…”
“Next time we’ll have to think of something even better…” Mom went on to say. “I’m telling you…if he gets into a good college, we’ll have to bring our other sister over…” Auntie smiled. “We’re all proud of our boy.

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

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It wasn’t okay…it wasn’t right, but she needed someone to confide in. “I’ve been having these feelings and they’re so wrong, so immoral…and it’s been giving me so much anxiety,” Mom said nervously to her sister. Although she reluctant at first, she finally confessed that she felt like she was in love with her son. “I’ve been having these sexual thoughts and feelings…and so much love and attraction and it’s all I can think about,” Mom explained to her. “I can’t even be around him because I just want to touch him and kiss him and do all these things…and it’s so wrong and it’s so gross. I don’t know how to get over it, I don’t know what to do…”
Yes, of course, it’s wasn’t normal, but Sydney did the best she could to make her sister feel better. “What we should do is find a solution,” she told her. “Maybe you should just do it…just do it once and maybe all these feelings will stop. If it’s stressing you out this much, it’s bad for your health.”
Mom was nervous, but Sydney promised to stay and guide her through everything. “Hey nephew,” Auntie called out to you. You entered the bedroom to see them sitting closely to one another. “I’m gonna let her do the talking…” Mom said shyly, “I’m feeling a little embarrassed and awkward.”
Auntie was blunt about everything. She told that Mom was attracted to you and the man that you had become. “And who could blame her…” Auntie tried to make things sound reasonable, “you are the spitting image of your father when he was younger – you look just like him.” And in order to help ease the stress of this awkward situation, Auntie suggested that maybe the two of you should have some intimate time together and get past this.
And, of course, no one would talk about this outside the family. It was only to help Mom get better. So, under Auntie’s watch and instruction, you and your mother began to experiment. You started off slow. First you and Mom would kiss, then you’d try longer, more passionate kisses. “That did feel kind of nice,” Mom blushed.
“Maybe we should take it a step further,” Auntie told her. “Um…maybe show off a little? I mean, you have a beautiful body.” Mom pulled down her lingerie and invited you to touch her big, perky tits. After that, Auntie told Mom to touch something of yours. The two of you went back and forth touching one another – groping, stroking, fingering, licking, sucking – until it was time to have sex. Mom didn’t want to feel too awkward, so she faced the other way and let you fuck her from behind.
After everything was finished, Auntie made sure the both of you were okay. Mom was still embarrassed, but she shyly mumbled, “Maybe can try it again sometime…just whenever I’m feeling stressed out…”

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

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A full family experience with an amazing mom & aunt duo…a very highly recommended clip!
As a growing boy, you had expressed interest in girls. You had asked Mom a few questions already, including how to kiss a girl, and she thought it might make things easier to bring in your aunt. “I’ve been giving it a lot of thought on the best way to explain it you,” Mom went on to say, “and how to show you because I really don’t want you to have one of those awkward, weird first experiences.”
“We’re just going to give you some lessons and some pointers, and hopefully it answers all your questions. Does that sound okay?” Mom asked. She had just told you that her and your aunt used to practice kissing with one another while they were growing up, and that a demonstration might be the perfect way to teach you.
“Make sure you know the girl wants to kiss you. You’ll be able to tell with her body language. She’ll look at your lips, in your eyes…make sure she wants it,” Auntie told you. “That’s an important lesson.” Now, along with all the other pointers they had already given you, there were different ways of kissing.
Mom and Auntie demonstrated passionate, romantic, sweet kisses, then showed you what a french kiss was. You could caress the girl’s face, compliment her – always remember to show her respect. As you watched your mom and aunt kiss for the first time, you felt your cock stiffen. There was something incredibly taboo and sexy about watching their tongues flick against one another’s, and it wasn’t long before they discovered you had a hard-on.
They took the situation as a teaching and learning experience. They’d continue to teach you more about sex and all the different things a girl might do with you if she liked you – all the juicy stuff that happened after kissing. Mom and Auntie would give you your handjob and blowjob together, then you’d lose your virginity to the both of them.

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

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“Before you go out tonight, there’s something I need to talk you about,” Mom closed her book. “Do you a minute?” You knew exactly what this was about. You had been acting strange and nervous around her lately, and she was concerned that you were hiding something, or that you were in trouble.
“I’m your mother, I want to know if something is troubling you,” she said sympathetically.”Don’t look at the ground, look at me.” You hesitated to tell her what was going on – it wasn’t right, it was immoral. You weren’t supposed to have feelings like this, but you did. You had a crush on your own mother.
“What do you need? What can I help you with?” Mom asked. She told you that she was getting calls from school about your lack of engagement in class. “You’re also acting oddly around your father – I need to know what’s going on. I mean, you’re not even dating…you’re going out tonight alone.”
There was no point in dating. Your mom was far more beautiful than the girls at school, and you could never get her out of your head. “Me? Well honey, you’re always going to be Mommy’s special boy…I’m flattered that you admire me. Do you like my hair…my smile, personality?” she was surprised at what you had just told her.
“Oh…okay, um…well honey, as your mother, I want you to be well adjusted and happy in normal everyday activities…” she proceeded to say. “What can Mommy do for you? If you want to look at Mommy, that’s fine.” She stood up and let you look at her petite, flawless figure.
“I know Mommy’s quite a bit more grown up than the girls in your class,” she smiled, “but soon you’ll go to college and you’ll meet tons of girls that are mature.” She invited you to touch her body, letting you grope her beautiful, perky tits and juicy ass. “Do you feel better, sweetie?” she asked. “I want to do anything I can to help alleviate your anxiety.”
Mom continued to let you explore your fantasies with her…her hand and mouth wrapping around your throbbing cock, then allowing you to penetrate her pretty pink pussy. She didn’t want you to feel embarrassed or ashamed for admiring her, for having a crush on her…and she’d do anything to make you feel better. Anything for her sweet boy.

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

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“Honey, can I come in?” Mom’s voice was soft behind your bedroom door. “There’s something I need to talk to you about.” She told you that she had received numerous phone calls from school about you falling asleep in class. “Your father and I both noticed that you’ve been up all night watching TV, playing video games…you’re on the computer. I understand insomnia, I went through the same thing when I was your age.”
Falling asleep in class meant failing grades, and if that continued, you wouldn’t get into a good college. “We really need to do something about this, honey,” Mom’s eyes were stressed and concerned. “So, I was brainstorming of ways to get rid of some of that excess energy, so that you can get a better night’s sleep.”
Sure, there was melatonin, teas, medications…but Mom was certain she had a better idea. “Do you agree that this might be a little bit of a problem? Besides your studies and all that, you’re not going to get a date if you’re asleep at your desk at school,” she went on to say. “So, this may be a little bit unorthodox, but I think maybe we should…sexually train you at night, after your studies…would you like to give it a try?”
“Now Mommy’s definitely open if you are,” she smiled sweetly in an attempt to make you comfortable, “and I’ve been told I’m not too bad looking.” Every night, after she had checked that you finished your homework and studying, she would begin the new night-time ritual. “I would get you nice and hard…” she said rubbing your cock, “are you comfortable with Mommy doing that?”
“Mommy just wants what’s best for you…” she told you. “And as a bonus, this could help you with your dating life – I know prom is coming up soon. You’ll improve your studies, get that pretty girl I hear so much about to go to prom with you.”
So, Mom guided you through her new idea, and soon enough, you were worn out…just like she thought you would be. Tired and ready to go to sleep.

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

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As soon as he woke up, he could feel something was off. Platinum blonde hair ran through his fingers, and then pressed against big, plump, pink lips. His body was petite now, and when he looked down, his morning wood wasn’t there – nothing was. “Oh my god,” he said startled.
He went on to find out that he had a high pitched, feminine voice, perky tits, and a vagina in place of his manly traits. His blue eyes narrowed as they scanned the familiar room. “Wait…is this my Mom’s room?” he asked himself. He scrambled to pick up the cell phone lying on the floor, then looked at his reflection in the screen. “Oh my god, I’m my mother,” he said shocked.
He wasn’t sure what to do – he had so many questions. “Is she me?” he wondered. “Is this really what she wears to bed?” he looked down to see she had black, revealing lingerie on. “I wonder if she woke up with a penis today. Oh my gosh, okay…calm down.”
He sat down on the bed with a million thoughts running through his head. “You woke up in your mother’s body…” he thought about his situation, “well, my body now.” His curiosity grew, and soon, his soft hands were running against his mother’s flawless, mature body. “Anything I do would be…” he tried to justify what he was about to do.
He struggled to pull off the complicated one piece. “I guess she got tan lines from being at the pool so much,” he said noticing the sun on her fair-skinned body. He giggled as he jiggled, twerked, and smacked her ass. “It’s so weird from this angle,” he looked down at his shaven, bare pussy. “Easier to find the clitoris, that’s for sure…I’ll be sure to remember that.”
He began to explore himself down there. “No wonder women are so crazy about that,” his finger flicked against his clit. He moaned as he touched his pussy, masturbating until he brought himself to an orgasm. “Oh my god…” he panted. “What do I do now? God, what does Mom do all day? I hope it’s not this…well, maybe I do.”

GENDER TRANSFORMATION, TRANSFER FETISH, TRANSFORMATION FANTASIES, TRANSFORMATION FETISH, TABOO, MILF

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“Oh hey, sweetheart,” Mom said after taking a sip of her wine, “what do you need?” Exhausted from a long day at work, she had slipped into some lingerie, and was drinking for a relaxing buzz. “I’m just unwinding,” she slurred.
She asked you to sit beside her, quickly forgetting why you had come into her bedroom in the first place. “You’re such a handsome young man,” she said sweetly, “I made such a handsome boy.” She giggled as the wine started to intoxicate her more, and she bluntly asked, “Do you think Mommy’s pretty?”
“I know Mommy usually doesn’t act like this,” she said sprawling onto the bed, her fingers running through her beautiful, blonde, wavy hair. “One day when you’re older, you’ll understand – I just needed a stress relief.” Her drunken eyes shifted downward and she let out a smile, “What’s that? I’m your mommy, that’s naughty!”
The way Mom had been flirting with you and moving her flawless figure on the bed made your cock hard. “You mind if I touch it?” she asked. “That’s not inappropriate, is it? Does my sweet, little boy like that? I bet you’d like to see a bit more of Mommy, wouldn’t you?” Her hand brushed up against your erection, and she began to undress, exposing herself to you for the first time.
She invited you to touch her perky, perfect tits. “What do you think, son? Do you like Mommy’s tits? They’re so soft, aren’t they?” she smiled. You weren’t sure if Mom knew what she was doing, or if she was too inebriated to realize the immorality of it. Soon she was asking for a sweet kiss on the lips, then offering to wrap her warm mouth around your cock.
It was obvious that the wine had made her tipsy and horny, and she laid back to allow your tongue to circle her pink pussy. She was ready to have you inside of her, to be filled with your cum. “You wanna make Mommy cum, baby? Do it harder…just like that,” she moaned. “Cum with me.”

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

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