Tag: sissy phone sex

Ageplay Phone Sex with Tori: I LOVE Teasing Daddy

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Don’t fool yourself Daddy, you know that cute little girls like me don’t think smalls toys are as much fun to play with. Ever since we were very, very tiny it’s been embedded into our minds. How would that be possible if it weren’t true? Obviously, you don’t fit in that catorgory at all Daddy. Not even close! At least you know you can fit in any hole, no matter how small it is. I guess that’s the only upside to having an itty bitty dickie like yours.
It must be upsetting a lot of the time though. Even the tighest cunny probably feels loose to you. Whenever you’re balls deep inside my juicy little pussy, I can hardly feel a thing. But you already knew that, didn’t you? Why else would ask you everytime if it was “in yet”? It’s not like I have to say that because you hear it all the time, not just with me either. I just love seeing your face turn red. I know you can’t help how big you’re teenie weenie is Daddy, but that doesn’t mean that you shouldn’t be ashamed of it.

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A Night With Daddy

milf phone sex darlaI love when Daddy comes to visit and so does my sweet son. Now that Daddy knows that Harley is a sissy we all have more fun then we ever have before. I have always been Daddy’s girl. As far back as I can remember Daddy has gently touched me in places that made me tingle, even before I knew what that meant. As far back as I can remember I have always loved kissing the head of Daddy’s worm and licking the sweet juice that dripped out for him. For me it was like candy. As far back I I can remember I loved it when Daddy licked and sucked my little nipples and my tender lips. The older I got the better it felt and the more I realized how much it meant to Daddy too. Now that Daddy is a Grandpa, I love sharing Harley with him too. Now he has two sweet girls to play with. Harley puts on his lacy panties when Daddy comes over and loves to lick and kiss Daddy’s dick just like I used to. And daddy loves to slide his dick inside Harley’s tight vagina just as much as Harley loves to have it done. I love the way Harley’s eyes glass over when daddy sucks her little tits and when Daddy lays her down and lifts her legs high in the air and licks that vagina before sliding his Daddy dick inside. We love our nights with Daddy.

Sissy phone sex with Tori: Forcing Daddy to Wear Panties!!!

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Daddy likes to play pretend a lot, but he’s not fooling any body. Why does he even bother? Once you’ve seen his dick you’ll never consider him a real man again anyway. He looks like a ken doll when he wears pants, it seriously looks like there’s nothing there. His teenie weenie gets rock hard in public all the time too and no one ever notices! No matter how close you look there isn’t the slightest bulge in his pants.sissy phone sex His tiny cock looks more like a swollen clitty and a girl can’t do much with that. Believe it or not he still tries, but I found a creative way to make it more difficult for him. I threw out all of Daddy’s briefs and now he’s only allowed to wear panties! Any girl crazy enough to want to sleep with Daddy will have to peel of his frilly pink panties first! It’s been working so far too. Daddy looks so sad, but I love it.

Last night a girl ran out of his room laughing before he even a chance to pull his witty needle prick out. He was so embarrassed that he tried to hide in his room so he didn’t have to face me. Poor Daddy must have been too upset to think clearly. How could he forget that I have a key to his room? I forget how silly he can be sometimes, he actually looked surprised when I walked right into his room. His eyes were all red and puffy from crying, but I still laughed right his face.

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We Love To Match

incest sex darlaWhen we found out he wanted to come over and play we were so exited. He specifically asked for Hailey to be nice and pretty for him. He wanted Hailey to be Daddy’s girl for the night. Harley was instantly transformed and wanted to go shopping so we could look extra pretty for the night ahead. Of course I love shopping with Hailey so off we went. We bought the prettiest light pink lingerie set that you have ever seen! When we looked at ourselves in the dressing room mirror we both knew this was the perfect thing for the night. We were dressed and ready when he got there. As soon as he saw Hailey his dick got rock hard and he led her to the bed room. I lay on the bed with my fingers deep in my pussy while he kissed Hailey tenderly, rubbing her little clitty through her silky panties, working his way slowly to her little vagina. He gently pulled her panties to the side and licked his finger before sliding it inside he. Watching Hailey arch her back, pushing into his hand, moaning and kissing him back made my pussy so wet. I knew I wasn’t going to get fucked tonight, just by the way he was enjoying his little girl. It’s OK I like these nights, it’s all part of Hailey’s sissy training.

Kinky Phone Sex with Tori: Daddy’s New Years Humiliation

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You embarrassed me yet again Daddy and on New Years Eve too! Wasn’t last night supposed to be all about fun? At least I got to use the new Hello Kitty bong you bought me for Christmas while I laughed at you. What exactly were you thinking? After like 3 drinks you decided it was a good idea to whip your teenie weenie out. Some people didn’t notice right away because it’s so itty bitty, but when they did everyone started laughing. Honestly, I think it’s shrinking Daddy. It looked like there was a little button between your legs instead of a cock!kinky phone sex Tori
The measuring contest must have been really humiliating because no one was even close to being as small you. The biggest cock at the party was 9 1/2 inches and soooooo thick. My kitty was dripping wet just from looking at that massive prick. Before I knew it his big fat cock was deep inside my tight cunny. As he fucked me hard and deep I could feel my little coochie stretching. No matter how hard you try, you’ll never be able to make me feel this way. Having you watch a real man give me what you can’t is the closest you’ll come to pleasing me physically.
I was nice enough to let you lick my cunny last night, but only after it was filled with cum from that enormous dick. That guy and I were taking bong hits while you cleaned my messy kitty your tongue. Maybe I just had a buzz, but it actually felt good for a change. Don’t you feel lucky to have a sweet Princess like me?

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Family Fucking Christmas Eve Tradition

family fucking mother sonMy son and I have a Christmas Eve holiday tradition. When he was younger, and I was still married to his Daddy, as a family we would open one gift a piece. Then we would sit down and have a nice family dinner with all the trimmings. It would be me, my daughter, my son and my husband.  One year when my son was just a horny teen, he decided we needed to be family fucking. Now, him and I had been fucking on the side. For the most part, he had replaced my husband as the head of the house. He was more of a man than his Daddy. Had a bigger cock, knew how to use it, and never had an issue getting hard.

Well one Christmas Eve, my daughter was with her grandma, and it was just me, my son and his Daddy. My son was pretty pissed off at the way his father treated me. He was really young still, but like I said, he was all man. He told his father there was a new tradition in the house. The man of the house got to fuck the woman of the house and the boy had to watch. He pushed his father down on the dining room table, pulled up my dress and started fucking me as his father watched. Told his Daddy to stroke his broke down dick and watch as the real man of the house took care of me.

His father was dumbfounded. Couldn’t believe his son was fucking me, let alone taunting him. But it turned him on too. His broke down dick was harder than it had been in years. He laid there on the table stroking his cock as our son fucked me doggy style. Turned out my husband liked being a cuckold to his son and my son loved humiliating his father. And I enjoyed being fucked by my son in front of my husband. So even though I divorced my limp dick cuckold of a husband, he still joins us every Christmas Eve for a family fucking cuckolding Christmas. He has to watch us fuck our brains out. And, to make it more humiliating, I make my ex lick his own son’s boy batter out of my cunt.

Tomorrow morning, my ex will be gone, and it will be just my son and my daughter fucking under the tree and opening presents. I am so lucky that I discovered who the real man of the house was many years ago.

Santa Baby!

Sissy phone sexSissy Santa come and be a Fairy Fag for me.

You’ve been a fairy good girl. Sissy Santa,

So grovel on your knees tonight.

.

Sissy Santa, Come and wear you crown

For me, Light pink. I’ll laugh at you my dear. Sissy Santa,

So grovel on your knees Tonight.

.

Sissy Santa, Come deliver presents to me.

A shopping spree, Sissy Santa

So grovel on your knees tonight.

.

Sissy Santa, One thing I really need..

To Plead; You really are Fairy Fag.

Sissy Santa, grovel on your knees tonight.

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Sissy Santa, Wear your white stockings too.

Don’t forget your slutty shoes.

Sissy Santa, Grovel on your knees tonight.

.

Sissy Santa, Your such a Fairy Faggot.

A queer. You wear your dresses just fine.

Sissy Santa, Grovel on your knees tonight.

.

Sissy Santa, You prance around like a slut.

You make me laugh to hard.

Sissy Santa, Grovel on your knees tonight.

.

Come on sissy, Time for you to dance and sing, for me. You’ve been a faggot all year.

Wear your whore clothes. And your Santa hat, for me. And get down on your knees.

Sissy Santa. Time for you wiggle and please. Shake that ass you pay piggy!

Sissy Santa. It’s all to entertain me! So hurry on your knees tonight!

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Everyone Knows She’s Wendy….

sissy training darlaShe hasn’t been to see Mommy Darla in a long time. So when I opened the door and saw her standing there in her pretty pink baby doll nighty with her thigh high stockings, her big D cup bra stuffed, and her make up done to perfection, my pussy got wet instantly. I know what my beautiful little girl, Wendy needs when she comes to see me. She needs Mommy to play with her little clitty while getting her tight mangina ready to be fucked. She loves to kiss Mommy and lick Mommy’s pussy before gently fastening the big black strap on around Mommy’s waist. But the one thing that my sweet little girl loves most is when Mommy calls her big black friend over and she becomes Mommy’s little sissy faggot. She loves when we call her names and Mommy lets him stick his huge black dick in her while making her the slutty little girl that she dreams of being. I charge my friends to use and humiliate her while fucking her sissy faggot mangina. I put half of the money in a jar and the other half is mine. When I have enough money I will surprise her with a set of real tits of her own!

What Kind of Mommy Do You Need?

mommy phone sex son cumDo you need some mommy phone sex tonight baby? I am the mommy of your wet dreams. Equal parts sensual  mommy equal parts dominate mommy. Guess you could say Mommy is a switch hitter. I have three boys, and I am a different kind of mommy to each of them. I mean no two sons are alike, and each boy needs and wants certain things. My youngest son, he is at that age where he  has a constant hard on.  I help him out by being his private cum dump mommy. It is not healthy for a boy to have a hard on 24/7. He is also socially awkward, has trouble making friends. So, I let him have sleepovers often so  his friends can play with a hot MILF.  All young boys love a MILF. Especially one who lets them cum all over them and fuck her ass.  At these sleepovers I let his friends gang bang me and give them booze and pot.  It makes him very popular at school. I love helping my boys.

My middle boy is a sissy. He steals mommy’s panties, cums in my expensive shoes, wears my clothes. He needs a sissy trainer. A mommy who can help feminize him, make him look pretty, while teaching him to suck cock. I have to be stern with him, sensually dominant so he can bloom as a sissy but understand who is in charge. We shop together, get our nails done together, play dress up together. He is really the daughter I always wanted.

My eldest  son is a delinquent. Gets into all sorts of trouble. Skips school, gambles, does drugs. I love his cock and I love fucking him, but sometimes I just have to put on my strap on and fuck his ass, or play tease and denial games with him. He needs to learn he just can’t do whatever he wants without consequences. And he certainly does not deserve to cum if being a bad boy. He brings out the bad mommy in me.

So you see, I have three very different boys, each with different needs. I am the type of mommy each of them needs. I can be whatever kind of mommy you need too.

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Sissy Phone Sex with MaryAnne: Mommy’s Sissy Boy

sissy phone sex mommy sonMy name is Nikki. I am a sissy boy. My mommy Mary Anne makes me wear pretty pink frilly dresses. She even puts me in diapers. She says because she is my Mommy I have to do whatever she says, whenever she says it. You see, I was born with a little clitty, not a dick. Mommy hoped it would grow but it never did. Then when she found me playing dress up in her clothes and prancing around in her heels, she said I was more like her daughter than her son. Ever since then I have been Nikki. We shop for clothes together, get our  hair and nails done together, even pick up boys together. I am my mother’s sissy.

Last night she gave me very special instructions. I had to first go to Macy’s and purchase a new dress for myself along with some sexy lingerie. I had to make sure the sales lady knew that the clothes were not a gift, but were for me.  I then had to go this local bar in our neighborhood. I was a bit scared. Wasn’t sure how a girl like me would be received. Some guys were mean. Called me a fag and a sissy. Mommy said I was to find one who would buy me drinks and let him  fuck me. She said I can’t be a true sissy unless I get my back door cherry popped.

Sure enough I found one. I got a Pixie Stix Martini, 5 actually. Made me feel even more girly. We left together. I thought he would be all romantic and sweet with me, but he pretty much took my back door pussy. It hurt. He laughed at me. Called me a fag. I went home to mommy with my bum full of cum. She laughed at me too.  Mommy said I was a silly sissy. She made me bend over her knees,  pulled my panties down and she spanked me. She enjoys laughing at me and paddling my bum, just because she can.

I love my mommy. I love being her special girl. She has other sissies too. I have to share her. I don’t like that. I am suppose to help her find more special girls. Mommy never has enough sissies. You see sissies provide my mommy with amusement.  Sometimes even tributes. She loves to dress us, humiliate us, pimp us out, make us do embarrassing tasks, even put us in diapers. So if you are a good sissy like me, call my mommy and we can be sissy sisters.

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