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.
Tag: mean girl phone sex
Going Down The Rabbit Hole
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.
Alone Time
Its finally my turn for all your attention. I have been bringing you bimbo virgins all year long, and helping you torture them and take away everything that means anything to them during your ass rape porn. Now it is my turn to get some of that pain inflicted on me. I crave it every time I watch you tear one of them up. I watch as you split them in two, and I slap them around while you fuck their innocent little twats. Now its time for some real fun with your perfect little accomplice whore that knows how to handle the pain.
You have a surprise for me – some ropes to the ceiling beams to tie my arms up. I can fight as hard as I want, and you know I will try at first but then do anything and everything you say. I know my time alone with you is rare, and I won;t waste one second of the torture you will inflict on my tight little body. My arms are tied, legs spread, standing and waiting for your order. You tell me to bend over and begin to whip my ass so hard that fire shoots through me. You make me count out loud – WHIP -one, one thousand, WHIP – two, one thousand, WHIP – three, one thousand… and I count as I am beaten to 100.
I can feel the blood trickling down my legs and it feels so cold. My ass cheeks and back are stinging like a million bees stings and I know I will wear the scars forever. You’re breathing heavy and your cock it hard. But you have more rage before the fucking begins. The blood and pain are no where near enough for your pain whore. You beging whipping my breasts, and I count again. This time to 200. My legs are beginning to give out from the pain draining my adrenaline. You are wearing me down but feeding my addiction.
You finally go behind me, reach around and grab my breasts. Your grip burns my open wounds from your sweaty hands. I never scream. I am not one of those bimbos. I am your pain whore and I am thankful for every sensation you send coursing through my body. I feel you enter my ass with your cock, with nothing but my blood as lubricant. You fuck me without mercy until my ass is ripped like those virgin cunts you enjoyed all year. I hang limp from the ropes as you cum all over my body. You cum feels so warm, and my head is spinning from the pain. Thank you for spending time with just me. I promiseI will bring you a good girl tomorrow….
I’m the brattiest bitch!
“Hi, hello, this is your princess speaking!” That’s what you can expect when this bitch right here answers the phone. I am no cheap whore, and I do not take no for an answer so if you are looking for a submissive bitch then move right along. I am dominant and always get what I want. That’s why guys call me for things like blackmail or humiliation, and when they are looking for a bratty bitch to demand what she wants from them. I have no issue forcing you to give me what I want; I simply do not take no for an answer. The word no isn’t even in my fucking vocabulary. I’ve just been spoiled too fucking much to not get everything I want, and to not get pleased when I am damn good and ready to be pleased. That’s why I talk to so many men, they all want something different and so do I. This body doesn’t pay for itself – you want me to be that hot toned bitch then keep paying for my organic food and gym membership. I really love when you desperate losers call me and want me to humiliate you. Or the pathetic sissy boys – they are such a joke wearing my panties and shit! Ha! Whatever you’re into, I am too, because I love money and I’ve grown to have no taboos no matter how spoiled I am. It’s the price I have to pay to keep living my life the way a princess should, and to pay for all the things my current sugar daddies won’t. I don’t blame them; they can’t make it too obvious to their ugly ass wives. I’m already that bitch who always wants to be fucked all the time, 24/7. Ha, I’m the girl you love to hate. But you can’t stay away from me either…
Mean girl phone sex with a Princess
Just look at you. Sitting there just drooling at me. It is disgusting! I can smell the desperation all the way over here. You know, guys like you make me laugh. You honestly do. You have no chance in hell with me or any other girl like me, yet, you keep trying. You are awkward, and have a pretty meaningless job that you haul your pathetic butt to every day. What good will that do for me? Nothing!
You see a Princess such as myself is worth more than what you can afford with that dish washer salary. I bet you have to help your Mom buy cat food for all those kitties that live in your trailer with you two. Gross. Mean girl phone sex is my forte. I like treating you like the absolute looser you are. Because I know that someone like you loves it when us Perfect girls are mean as fuck to you. You go home and whack off on your unmade bed while your Mother calls for you over and over again to come and scoop out the cat shit from the littler boxes. Again, GROSS!
2 girl phone sex With Princess Melody and Princess Katelyn
Guess what? Princess Melody and I are teaming up to give some mean girl phone sex tag team action. We know you desire Us. We know you lay in your bed at night and think those “if only” thoughts. That is what they will always be, meager “if only” thoughts. Because just as I do not allow anyone to tread on any part of my perfect Princess self, neither does Princess Melody. We were created to be worshiped, adored and to make you feel absolutely humiliated! Just think of how happy you would make Us by clinging to our every word. Hand washing Our lingerie, getting to feel the still wet cotton that was snuggled up against Our wet heavenly pussy as We wore them earlier that day. Or perhaps you could even get a special treat and get to see what a real Man’s cum looks like as it clings to the inside of our panties after being freshly fucked.
We will laugh at you, demean you, degrade you and turn you into the cock sucking faggy you are. You know you would do anything for Us. Anything at all. All with the barely there promise that maybe, just maybe someday you will get to feel what it would be like to be with one of Us. Not that that promise will ever come to fruition, but there is always hope isn’t there? *laughs*