Category: Babysitter phone sex

Neighbor Girl

I should have known that you were too eager to hire me to house sit while you were out of town. My folks told me that you were leaving town for three weeks and I could make a hundred bucks just by bringing in your mail and watering your plants once a day. I didn’t want to be rude and not accept the offer, so I said okay. I met you at your place to get the key and just the way you were looking at me gave me the creeps. You didn’t have any qualms about looking me up and down, and brushing my hand a little too long when handing me the key.

The next day, when you had supposedly left for your trip, I headed over to water the plants. I let myself in and locked the door behind me. I had the weirdest feeling and the hairs on the back of my neck was standing on end. I kept telling myself I was being silly, but I didn’t feel like I was alone. I went to the kitchen to fill up the pitcher, and i could have sworn I heard a noise in the living room. I stopped to listen, but heard nothing else. I made my way back into the living room to the plants and began to water them.

Just then, you came up behind me and put your hand over my mouth and wrestled me to the floor. You had never left – it was all a ruse to get me here alone. You overpowered me and there was nothing I could do. You kept saying things like this is what I get for walking around the neighborhood like a little tramp and that you were going to show me what happens to dirty cum whores like me. Before I knew it, you had me hog-tied and gagged on your couch and were jerking off above me.

The things you were saying told me that you had been watching me for a long time. You had finally decided to make a move and I knew instinctively that you were going to hurt me. What scared me even more was that you never once mentioned me not telling anyone. I began to wonder if you were going to snuff me out. You began running your hands all over my naked body, and I cringed at your perverse touch. Your skin felt so rough against mine and your cock was dripping with cum as if it were drooling.

You knew my parents wouldn;t be looking for me, and that you had all afternoon to ravage my body. You did just that. You put your hard cock in all of my holes and never stopped berating me with your words. After hours of being fucked brutally and told what a little teasing whore I was, I began to believe it and my pussy responded by cumming all over your hard cock. Who knew that you, the neighbor who always gave me the creeps, would be the best fuck I ever had?

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!

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.

Secret Santa

I had the WEIRDEST Dream last night. My best friend Amber was asking me how I got so many good presents from Santa. And I told her I would show her! It was Christmas eve and we got dressed up like dolls! I was dressed as Ragged Ann and she was Best Pals Janet. That is how Santa Likes it! And we waited for Santa to show up! When he arrived he was VERY happy to see us! He had me get on my knees and suck his cock calling it his candy cane! I sucked Santa until he was dripping wet and throbbing hard! Santa pulled Amber over to him and told her lick his balls… and she said NO! I was so shocked I had to stop sucking and whipped my head around to look at her. Amber was saying how she wouldn’t suck a old mans dick! I was SOOOOO embarrassed! And Santa was soooo Mad! Santa pushed me back and Grabbed Amber. Santa called Amber a selfish little Bitch! He was very mad Amber expected lots of presents and was to selfish to give Santa a present in return.

Then Santa sat down and pulled Amber over his lap and started spanking her ASS! Amber was begging me to help her… but I knew she was getting what she deserved! Then Santa pushed her on the floor and Said “ You better not pout, You better not cry.. You better not scream cause I’m going in Dry!” And he did!

Santa rammed his cock right inside of her. But Amber did scream. Amber begged for me to help her as Santa pounded her! Then Santa dropped his load right inside Amber’s tiny pussy! I was right there to clean Santa’s fat cock up! And Santa gave me so many good presents. Even some yummy cock shaped Santa chocolates. Amber got Coal and a sore ass! 

Black Beauty Brittney Style

Brittney is such a little sex slave. She is one hot little slut. I never know what I will find when I come home and she is babysitting and yesterday was no different.
I walked in the door and could hear Brittney and the girls in the bedroom. Creeping as quietly as I could, I eased the door open. There was Brittney on all fours. She had on black thongs, black thigh high boots, a black bra with silver spikes on it and a black collar with silver spikes. One of my girls had a black leash that was connected to the collar in her hand, she was yanking and pulling it almost to the point of choking Brittney. My other girl had a black riding crop in her hand. Brittney’s ass has red welts on it from where she had been whipped and when she turned towards me it was obvious that she was enjoying every minute of this by the wetness between her legs. I couldn’t stop watching as my girls made Britteny their sex slave. The littlest one climbed on Brittney’s back and started ridding her like a horse, kicking her in the sides and whipping her hard, yelling “Giddy up, giddy up, faster!” Soon they had tied the leash to the bed post and my oldest took the riding crop and began fucking Brittney with the handle of it. She was screaming “Cum bitch cum!” This couldn’t be the first time that Brittney let them make her a ex slave but it was the first time that I had witnessed it. I stayed there watching and fingering my pussy cumming with Brittney each time she exploded. She loves this type of sexual inter action. I am hopping she will be my sex slave soon, the girls are doing a great job, but I have a few things up my sleeve that I know Brittney will love!

Tiffany’s Teddy

I love hitting the bar on Sunday nights. The one thing I can count on is that it will have some very interesting patrons. Last night was exceptionally interesting.
I was already horny as hell when I got there and had decided I was going to get laid. Tiffany was at the house sitting with the girls so I knew I didn’t have to be home anytime soon.
Sitting at the end of the bar was a gruff looking man. He looked like he was drowning his sorrows in booze. I went over and sat next to him striking up a conversation.
He began to tell me how his girl had just dumped him claiming he was a dumb ass and that what he thought was a funny and loving gesture had backfired on him.
Probing further I asked what had happened that caused her to dump him in such a way.
He went on to tell me that she loved Teddy Bears. He had bought her every kind he could find in the year they were dating. So on a whim he decided to get her one that no one could ever have possibly gotten her before nor would ever again.
Thinking this was a sweet thing I asked where he found the Teddy and why she was so unhappy with it.
With sad eyes he undid his pants right there at the bar and showed me the tattooed Teddy around his cock.
I couldn’t help spitting my drink out as I burst into laughter. I know it was like rubbing salt into the wound but I couldn’t help it.
I felt so bad that I told him I had three girls at home that would love to join me and play with his Teddy, my two girls and the sitter.
I took him home and after the girls all got the same laugh I did, we eased his sorrows and played with Teddy all night long. Tiffany was especially fond of it so we named it Tiffany’s Teddy,

Accomplice Phone Sex with Samantha and Nyla

I am a mature woman with certain desires for young flesh. I know you understand. Young bodies are so tender, so innocent, so yummy. Now, I have a big brood of my own that I play with, but sometimes I need  young flesh that is not my own. Variety is the spice of life. That is where Nyla, this hot little coed on the block, comes into my taboo desires. Nyla, is my accomplice. She helps procure young ones for me. See, she often babysits neighborhood brats, and when she has one she thinks I will find quite delectable, she snaps a few pics, sends them to me, and we work out a plan for “Aunt” Samantha to stop by and play.

Nyla hit a goldmine of flesh the other day. Young twins. One boy, one girl. Double my fun. I showed up where she was babysitting with a big bag of candy and introduced myself to those sweet young beautiful things. Nyla did good this time. Actually, she always brings me the best fresh meat. Nyla loves being my accomplice. She gets off on watching. I brought the twins into their parents’ bedroom and dumped the candy all over the bed. I got naked as Nyla undressed them.  She sat back in a chair rubbing her sweet bald snatch smoking a cigarette as I had the twins eating candy out of my pussy and ass. Those sweet young tongues on my body were so hot. Two young mouths are always better than one. I even ate candy off their sweet little bodies. I love those little fleshy pussy mounds, hairless bodies and cute bubble buts. Do you?

Nyla knows just what I like too. She is the best accomplice. To reward her, I often let her come over to my place and watch me play with my grand angels. She is a p by proxy lol. Maybe you want to be my accomplice or I can help you? I am very skilled in the art of procuring young playthings!

Anal Phone Sex with Anastasia and Samantha

I don’t seem to have much luck with babysitters. Every little neighborhood teen I hire ends up fucking my sons or my grand angels.  I had no reason to believe Anastasia would be different. My brother was in town and we wanted to go see a musical but I was watching the grand angels that weekend. My son suggested this little blonde hottie from his school. He said she was a Daddy’s girl type, totally in to older dudes so she should work out just fine.

My brother and I went out had a lovely time. Anastasia checked in regularly with texts, even sent pics of her and the brats playing games. I honestly thought I had a keeper here. We get back to the house and the young ones are asleep, tucked safely in bed and the house is immaculate. Seriously, she was the best babysitter ever. I told her I would run her home after I changed clothes and excused myself to the bedroom.

When I returned, she was on her knees sucking my brother’s cock. Anastasia was polishing my brother’s knob better than me from the sounds he was making. My son was right, she did like older men.  My brother is nothing like me. He is pretty socially awkward. I am the only woman he has fucked that was not a one night stand. He has no game. As Anastasia was sucking him off, my son came home.  He was pretty turned on watching his Uncle get head from his friend.  Well, I wanted some cock in my mouth too, so I unzipped his pants and gave my son  a blowjob right next to Anastasia and my brother.

Anastasia begged my brother to fuck her ass. Turns out she is little anal Annie. My brother, although he fucks his sister, is fairly conservative in the bedroom. I couldn’t see him giving it to her up her pooper lol. But he did. He bent Anastasia right over without a pause and fucked her ass while she moaned like a virgin. I was not going to be the only girl not getting it in the ass, so I got on couch and begged my son to do me up the ass too.  The babysitter and I were getting fucked in the ass by the men in my house.  It was pretty hot to watch my brother give his first anal experience and to the babysitter no less while his nephew fucked my ass.

Anastasia and I were anal loving twins that day. We even swapped cock; I got my brother up my ass and she got my son.  We both had asses full of cum, only my ass had shared DNA up it. I liked her as a babysitter too. She left the young meat for me.  When a babysitter fucks one of my grand ones, I’m always forced to have the why is her pussy so much more tighter than yours conversation that I loathe. No tight cunt little coed is going my grandsons for me. I let my brother take Anastasia home because I knew she would blow  him again. When he came home, he kissed me and said I had a tighter ass. So maybe I have a not so tight pussy, but I have an ass tighter than a coed’s!