At first I wasn’t thrilled about babysitting over the weekend, but it turned out to be a lot more fun than I expected. The extra money was great, it just wasn’t my favorite part. For entire weekend I was alone with these two adorable little rugrats until their Daddy came home around 8. By that time they were usually in bed, so that meant that Daddy and I had some time to ourselves before Mommy came home at 11. We’d slip up to their bedroom or sometimes just play in the kitchen. Then, he’d pay me and send me home usually with a cum filled cunny. Sometimes we would even play with his Little Ones! They are so cute, I honestly have no idea how he can resist the urge to play with them all day long.
One day he saw me braiding their long pretty hair and seeing that in addition to the cute little dresses they were wearing drove him over the edge.That night ended up being the first time their Daddy had played with them that way. I loved teaching them how to please him and he really appreciated it, even offered to pay more just to teach them how I do it. Seeing their itty bitty hands wrapped around his giant throbbing cock made me so horny too, I wasn’t expecting that. So I hopped on their Daddy’s massive prick and taught them how he liked it. Those naughty little brats loved watching me bounce up and down on their Daddy’s fuck stick, they were practically drooling. Once their Daddy shot his cum deep inside me he had to recharge before they could take it for a ride, but eventually they got their turn. Apparently I’m good a teacher!
Tag: babysitter phone sex
Submissive Phone Sex with Summer: The Dangers of Babysitting
When I was younger, I had a slew of jobs. Normally, I quit my jobs and moved on to something bigger and better. But, I had this one babysitting job where I got fired. Still pisses me off too. Not only did I give their brat the best care ever, I had to put up with the twisted older siblings. Twin brats. A boy and a girl, who were not trusted with the little one, for a good reason. They were sick fucks. Only teens themselves, but on their way to become future serial killers. Not a gig went by that they did not torture me. One time the brother bound and gagged me while his sick sister spread my pussy open with clothes pins. My pussy was gaping open, and the equally twisted brother pissed right in my pussy. They took pictures of me to blackmail me with. I had to be their bitch after that if I didn’t want those pictures of me all over school. I was head cheerleader, most popular girl in school, had a reputation as an in charge bitch. If it got around, guys would think I was a submissive whore and feel they could do anything they wanted to me. No way was I letting that happen.
I let them call the shots for months. I had a reputation to uphold, plus their parents paid me very well. In hindsight, I think it is because they knew their older offspring were really Satan’s spawn. The day I got fired, I remember clearly. The twisted sister had my hands tied behind my back and was wearing a strap-on. She was skull fucking me, while her brother was fucking me in the ass. The little brat was tied in a chair being forced to watch. Their parents walked in on the show. They were quite livid. But with me. I was the one tied up being assaulted by their devil brats, but I was the one that got in trouble. The mother slapped my face, called me every name in the book and fired me. Didn’t even pay me. They still contended I was the bad influence even after the little brat said it was all his siblings fault.
Those evil twins eventually killed a schoolmate, so I guess it was a good thing I got fired. I got out with my life and unscathed, just humiliated. Their parents are still in denial over just how sick their offspring were. Not sure what ever happened to the brat. But I do know this, I started studying my ass off so I could get into college and never have to babysit again in my life.
Going Down The Rabbit Hole
Some times Delilah brings home her little wards. She knows that here she can torment them as she pleases and no one says anything to her.
And then there are times when things take a turn that not even I could have predicted.
This week end was one such time.
Delilah came in the door with her ward in tow. A girl that was a little older then her normal charges, limping with a brace on her leg and dressed like Alice in Wonderland.
It was an interesting sight indeed.
One of our Sugar Daddies happened to be visiting and I couldn’t believe the look he gave this pretty young thing. I looked down and his dick was hard as a rock. I knew he wanted her and so did Delila.
Ever the hustler Delilah took our Sugar Daddy a side and worked out a deal.
She gave her ward a cup of tea, that I am sure was laced with some thing, and told her that our Sugar Daddy was the Mad Hatter and was about to take a trip down her rabbit hole. When I saw her grab her strap-on I knew he wouldn’t be the only one taking a trip down that rabbit hole.
The rest was history.
I don’t know what Delilah got out of the deal but I know our Sugar Daddy was pleased with what he got.
Babysitter Phone Sex with Juliet and Samantha
When it comes to hiring babysitters, I don’t have much luck. Every little neighborhood teen whore I hire ends up fucking my grand angels. I was pretty sure Juliet would be different. My youngest son knew her, said she had daddy issues. She was into older men. In fact he said she was banging two of her professors. I figured she would not be interested in my grand boys.
I went out on a hot special date with my eldest son who is visiting with his wee ones for the holidays. We went a movie, even gave him a blowjob in the back of the theater. Juliet checked in regularly. She sent texts and even pics of her and the brats playing games. I thought to myself, “Finally, I hit the babysitter jackpot. ” When we returned home, my little ones were tucked snuggly in bed. The house was cleaner than when we left. Seriously, she was the best babysitter ever. I excused myself to slip into something more comfortable. I told her I would take her home. I wanted to take her home so my son and I could fuck our brains out like we did when he was younger.
When I returned, Juliet was on her knees giving my son a deepthroat blowjob. Now my son was older than she was, but not as old as her usual type. I was not happy. My son gave me this look like he couldn’t stop her. I told him, “Let me guess, she tripped and her mouth just fell on your cock?” I wanted to pull the little teen whore off his dick, but sadly he looked like he was loving it. Not going to lie, I was jealous. He saw the look on my face and tried to push Juliet off his shaft, but the little slut would not let go! She was sucking his cock like her life depended on it.
Juliet then begged my son to fuck her ass. Hell no. My ass was the only one his dick was going to fuck. I looked that little twat in the eyes and said, “watch how a real woman gets fucked in the ass.” I bent over the couch so my son could shove his big hard cock up his mama’s ass right in front of her. I was a little perturbed that it was hard because of her mouth, but once he was fucking my ass, I forgot any feelings of anger or jealously I had. He knows how to please his mommy. He shot a big load up my ass too. I pushed that little bitch to the ground and sat on her face. I told her, “Since you are so desperate for my son’s cum, drink it out of my ass.”
Juliet turned into a cum guzzling whore. She got her tongue up my ass so deep and scooped out all that cum. My son got so turned on watching this, he was hard again. This time, he begged me to let him fuck Juliet’s tight little ass. How could I deny him? Juliet and I let my son tag team our asses that day. My son fucked all the dominant bitch out of her. We turned that babysitter into a submissive little cum dump anal loving whore. Oh she may never babysit for us again, but she certainly will play with us again. Next time I’m breaking out my strap-on on that tight coed ass!
Babysitter Phone Sex Fantasy With A Submissive Daddy
He was late coming home from his date. He has been single for a long time and he needed to get out and away from his sons and daughter. After a long night of not giving a fuck of what they were into or up to they went to bed. I kept looking at the clock and it just kept getting later and later. I had had enough of doing this, I wanted to go out with my friends. I was stuck in this house with a parental control on the cable so I couldn’t even watch anything other than cartoons. My brain was going to bleed if he didn’t hurry the hell up.
He came in and didn’t even say he was sorry. He handed me a whole fifteen dollars and told me to have a good night. Are you kidding me? Fifteen dollars for six hellacious hours of babysitting? No, no, NO! I just looked at him and told him that I wanted more than this. He told me that he didn’t have anymore money, I told him then he better get back out there and tap an ATM or something because I was not satisfied with my pay.
He told me that he wasn’t going back out in a very stern voice. What? Nobody talks to me that way, EVER! I put my stuff down and poked him in the chest and told him, “Listen, YOU are going to get the fuck back out there, and YOU are going to get me more money…NOW!” He actually shrunk back. He mumbled, “Yes Ma’am.” I started to smile and let the anger fade from my face. I said, “Did you just say yes Ma’am?” He nodded his head and looked down at the floor. I said, “Well, well, seems Dear Old Daddy is a submissive pussy.”
He looked like he wanted to cry, but I didn’t care. I figured if I could not have cold hard cash, then he would have to work it off. He owed me a lot more than what he tried to give me. By the time I left he was dressed in some of his wife’s clothing that she left behind begging me to make him my very own Sissy Bitch. He also had his first taste of man cunt insertion. He wanted to cum so badly but he isn’t allowed to until he can get me the money he owes me. I fucking HATE babysitting, but I love Babysitter phone sex, especially when it involves a fantasy like this.