Category: Babysitter phone sex

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!

Dial Me Up for Babysitter Phone Sex

I had to babysit my little sister today, which usually isn’t that bad, but today was different. She had a little friend over and I had to babysit her too. Usually when it was just my little sister, we could play all the fun sex games that we wanted, but apparently this little one had no idea what it meant to really have fun. So I had to force the little brat to do what I said.

I told them both to get naked and that we were going to do kartwheels. The girl tried to refuse, but my little sis and I just pulled her clothes off and told her that we would tell her dad when he came to get her that was being bad if she didn’t. So, they were both naked, and doing kartwheels around the living room. I watched their tiny bodies flipping around, legs spread wide with each flip, little bakd pussies zipping by. My own pussy always gets so wet watching their little bald ones.

I sat on the couch, rubing one out while I watched them, and then the little girl stopped and came over, looking curiously at my pussy. She said that her mom’s pussy had hair all around it, and asked why mine didn’t have any? I told her thats because I am a pretty slutty little girl, just like her. She asked me what “slutty” meant. Geeze, didn’t her parents teach her anything? They always leave it up to the babysitter.

I told her to climb on the couch and spread her little legs. She did and I started fingering her pussy. She was squirming, and I asked her if she liked it and she said yes. I told her that makes her slutty, and that she should ask her daddy to do it for her later tonight when she gets home. I kept rubbing her little clit, and she was finally having fun. She told me I am the best babysitter in the whole wide world – and she’s right!

Babysitter Phone Sex with Samantha and Juliet: Tiny Teen Twat

I rarely use babysitters, but every now and then I am forced to. I was going to a rock festival with my son last weekend and we needed someone to watch the grand angels for a day and a half. My neighbor recommended her niece Juliet.  She was home from college that weekend and always needing some extra cash. My son and I met Juliet and she met the grand ones and it seemed like a good match. She was young and full of energy so she would be able to handle our brood. We left Juliet a couple hundred bucks for food and entertainment . Now, we told her our signal would be spotty so we would check in when we could.

The show got rained out for the second day so we headed home. We had no luck reaching Juliet on the phone. When we arrived Juliet was naked on top of one grandson and sucking the cock of the oldest one with the girls watching naked. Bad babysitter fucking her young charges. I was a bit miffed. Now, I have been fucking my oldest grandson for a few months, but the youngest one was still a virgin and I wanted to be the one who popped his cherry; not some skinny inexperienced teen twat. My son, however, was high fiving his sons. He approved of them getting some teenage pussy. Juliet was embarrassed at being caught. Pleaded for our forgiveness, asked what she could do to make things right.

My son told her to come over and suck a man’s cock for forgiveness. Obviously, he liked the idea of sloppy seconds with his sons. I watched Juliet suck my son’s big shaft and get him off quickly. Then my son fucked her tight twat while my oldest grandson put his cock back in her mouth.  My boys seemed to like her barely legal twat. I didn’t get it personally. Cute thing sure, but pretty scrawny and inexperienced. But then it dawned on me. Juliet had a jailbait body. Tiny teen twat. I’ve pushed out 6 brats out of my vagina, I got old lady loose twat. Well, as long as my boys were enjoying Juliet’s holes, I guess I was happy. Plus it was pretty hot knowing my youngest grandson is sexually ready to fuck his grandma. Perhaps I need to thank Juliet.

Babysitter Phone Sex with Samantha and Aiden: The One Who Got the Better of Me

I was asked by a friend of mine to babysit her niece Aiden once. Sweet young thing or so I thought. Now mind you I have 6 offspring, three of each. I thought a teen girl would be no problem to watch. But that little hottie Aiden was an unruly thing. From the moment her Aunt dropped her at my place to the moment she left, Aiden wrecked sexual havoc. She really got the better of me. I left her watching TV with my brats on the couch while I practiced being a domesticated goddess in the kitchen. Not twenty minutes later I hear a ruckus in the living room. I come out and find that Aiden has my daughter handcuffed to a leg of the coffee table and is fucking her pussy with the remote control while sucking my son’s cock. I am an open minded woman who plays with her own angels, but I was not going to allow some little twat to force my daughter to do anything.

I put Aiden in a time out in the guest bedroom. I locked the door and everything. Go back 30 minutes later to free her and discover that the crafty little cunt climbed through the window and snuck into the bedroom of my other son and was fucking him. This young thing had a libido that matched mine and I had some decades on her.  I pulled Aiden off my son and explained that the only ones that got to fuck his young flesh were his momma and his siblings. She got smart with me and said, “Why would he want your old snatch when he can have a nice tight fresh cunt?” I just about back handed the insolent little bitch.

My son intervened or I may have dang well smacked the little whore. I went to get her handcuffs thinking I was going to restrain Loilta to keep her off my brats. But before I could, she over powered me and handcuffed me to my son’s bed. My son was of no help. He liked fucking Aiden. In fact, he made me watch as she sucked his cock and told him how much better she was at dick sucking than his own momma. Before the night was over, she had all my little ones in that bedroom fucking them while I watched. She even had her own strap-on for the girls. But she didn’t use it just on them. Aiden was my sons’ first anal experience. I will always be upset about that. If anyone pops their boys’ anal cherry, it should be their mama, not some nymphomaniac school girl.

She finally released me from the handcuffs, but only after she fucked my 6 brats. I tried to threaten her with expose to her Aunt, but she was not at all scared. In fact Aiden dared me to tell her, taunting me with exposure of my incestuous lifestyle with my offspring. There was nothing I could do but admit defeat. An insatiable young twat got the better of me. Subsequently, I no longer babysit.