Category: Sissy phone sex

I Miss Sissy

sissy fairy fag6It has been such a long long time since I have written about Sissy. And even longer since I have heard her sweet sissy voice. I know that Princess Levi has been keeping Sissy busy and has been dishing out humiliation and shame just like Sissy deserves. I saw this t-shirt and thought of how pretty Sissy would look in a tight fitting t-shirt like this with a cute little mini skirt, a pair of heels and big hoop earnings. It  made me think that Sissy should get some glitter and the next time Princess gives her a Sissy day she should have to wear the outfit I described. When Sissy gets home, if she is a real good girl maybe Princess will let sissy be a PooPoo Pansy and play with her little tiny clitty covered in poo. But Sissy would have to buy some glitter and cover her clitty in glitter so that it mixes with her poo and she can say that her new shirt is accurate. That our Fairy Faggot does actual poop glitter. Princess might even be nice enough to let Sissy squirty squirt . Just thinking about it makes me giggle. What a sight that would be! incest phone sex darla

Sissy Training with Princess Tori

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Daddy looks so cute walking around the house in my panties. He looks so good doing it that now I make him wear them all the time. Of course Daddy isn’t very happy about it, but when has that ever mattered to me? I even made him go out and buy me new panties so he could have all my old ones. It probably isn’t hard to believe that they all fit Daddy perfectly. With an itty bitty dickie like his he actually looks like a girl if you don’t look at the rest of him!
Sometimes just to add to poor little Daddy’s humiliation I make him wear a training bra with my panties. It’s even better when they match! If I’m feeling especially cruel I’ll make him wear them both under his clothes all day, even when he goes to work. No matter what Daddy has to wear my panties under his clothes. He knows the rules, but sometimes “chooses” to forget them. I don’t buy his petty excuses and that’s why now he’s wearing my old training bras more often.
If Daddy argues too much or refuses to buy me something that I want I punish him even worse. I make him wear a matching bra and panties, then get on cam. I love playing with Daddy when I know hundreds of people are watching me degrade him. Sometimes I even put on my nice, 10 inch strap on and stretch out Daddy’s poor little asshole. Don’t feel bad for the bratty little faggot, he knows he was asking for it. Daddy probably only acts like that because he secretly wants it but he’s too much of a bitch to admit it.

sissy training

Family Fucking with Madison and Morgan

family fucking mother daughter sexMy baby girl Morgan and I have long celebrated family fucking. And we are not stingy with our love; we play with other family members too. A few weeks ago, my nephew visited. He was only suppose to be here for a weekend, but a blizzard trapped him with us for over a week. I had hoped him and Morgan would have some fun together. He is cute with a nice cock. I fucked my cousins when I was their age. Honestly, I think all cousins fool around at some point together. Morgan was excited to get her greedy little mouth on his thick cock. That was until she came out of the shower to find her cousin trying on her panties and this frilly pink dress she sometimes wears for daddy. Crap. My nephew was a sissy. Perfectly good waste of a nice cock I thought. Morgan informed me, we could still make him part of our family fun time. My baby girl is so smart.

I have trained my share of sissies in my life, but most don’t have such nice dicks, so it made me a bit sad. One day when he was here, Morgan and I brought home a playmate. A well hung older man, very alpha. I told him about my sissy nephew; he didn’t seem to care that he would be around. I guess I was silly to think it would mind. He was going to fuck the world’s hottest mother daughter duo, so any guy would put up with a sissy! He wanted to fuck me first. As I was on all fours getting his hard thick shaft forced up my ass, Morgan got all dominant with her cousin. Ordered him between my legs. She called him all sorts of humiliating names.  Turned him on too, because his sissy stick grew pretty big. When our fuck toy shot his load up my ass, I pissed it out into my nephew’s mouth.  “Who’s the sissy fairy cum guzzling clean up bitch of this family,” I cooed?

sissy phone sex mother daughterMorgan laughed her ass off, but my nephew ate it up, literally! I loved pushing that cum into his ass. Watching Morgan and I humiliate him, made our plaything hard again. Of course this time he fucked my baby girl’s ass. Once Morgan’s tight asshole was filled with spunk, she sat on her cousin’s face and force fed him his treat. Sadly the snow melted and he went back home, but my baby girl and I sure had fun feeding him cum once we realized his true nature. Next visit, we are going to dress him up and use him as fluffer bait! Having a sissy fag in the family just makes family fucking more kinky!

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.

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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.

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Sissy Santa, Come deliver presents to me.

A shopping spree, Sissy Santa

So grovel on your knees tonight.

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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.

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Sissy Santa, Your such a Fairy Faggot.

A queer. You wear your dresses just fine.

Sissy Santa, Grovel on your knees tonight.

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Sissy Santa, You prance around like a slut.

You make me laugh to hard.

Sissy Santa, Grovel on your knees tonight.

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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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