“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