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.
Category: Babysitter phone sex
Going Down The Rabbit Hole
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!
Sissy Phone Sex with Samantha and Jillian: My First Sissy Encounter
My oldest grandson has a crush on his occasional babysitter, my step niece Jillian. She is a cutie. I caught him one day smelling and jacking off with her dirty pantyhose. It was actually quite a turn on, but I worried he may be a sissy. I decided to talk with Jillian about it. She assured me it was quite normal for boys his age to like a girl’s panties or pantyhose. She said all the boys she babysits for steal her pretty soiled undergarments. They do it to smell her sweet teen pussy. She then invited me to go shopping with her and her special friend. She said she wanted me to meet her friend, so I could rest assured that my grandson was no sissy.
Jillian told me she met this rather special girl at the mall months ago. Apparently they were both shopping for frilly underwear and pantyhose and exchanged numbers. Jillian said she was a total sissy fairy fag and once I met her I would have no doubt that my grandson was just a normal hot blooded horny teen boy. I met them at the mall and Jillian introduced me to her Sissy Fairy Fag. I was stunned. I could not help but burst out laughing. She was in a precious baby doll dress, wearing jingly jangly jewelry, and pumps and makeup. She was even in a diaper with one of those plastic protectors on the outside. Now this was clearly a sissy. When she spoke she was quite poised and articulate, which surprised me.
Sissy Fairy Fag wanted to impress me with her babysitting skills in case I ever needed help with my grand angels. She informed me she has been taking care of her dollies for some time now and felt it was time to be in charge of live dollies. We were in a baby store shopping for some pacifiers and toys for her when she put her Hello Kitty doll on the changing table and demonstrated how to change a poopy diaper and feed a little one. I knew my grand girls would love her. She was a life size doll. A big old pathetic sweet sissy fairy fag. They could dress her up, put make up on her, do her nails, style her hair, sing songs together, play Candy Land, laugh at her… I felt good confident about Sissy Fairy Fag’s ability to take care of my angels. She was sort of a faggy Mary Poppins. LOL.
Thanks to Jillian, I know understood what a real fairy is all about. My grandson was far more of a man than Sissy Fairy Fag could ever hope to be, despite the age difference. My grandson likes to masturbate his cock with Jillian’s panties and pantyhose, not wear them and prance around the house playing with his little pee pee singling pansy ass tunes. In fact my grandson at his young age has a bigger pecker than Sissy Fairy Fag. She pulled her panties right down in the store to show us what a tiny little clitty she has too. I am still laughing. I’m in awe though of how someone so pathetic could be so comfortable in her skin. She had a great sissy trainer. Jillian told me, Mistress Levi made Sissy Fairy Fag who she is today. Well kudos to her. But I am keeping that hot bitch away from my sons and grandsons! I want real men in household.
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.