Tag: sissy training

A New Toy

kinky phone sex darlaWe have a new toy. It was Harley’s idea, she saw it at the sex toy store and begged me to buy it. She loves my strap on and how she feels when I fuck her tight little hole with it. She knows her little tiny clitty just doesn’t satisfy mommy like the big man dicks that she watches me fuck. To be honest when she picked it up and began telling me what she would do with it, I came right there in the store. After we made our purchase and had gotten in the car, I slipped off my panties and gave them to her to suck and smell on the way home. She loves mommy’s panties! As soon as we walked in the house she ripped open the package and grabbed my hand. Leading me to the bed she took off my dress and strapped the dildo onto her face. Laying on the bed she called me over and as I mounted her face and slid the silicone dildo into my wet pussy I herd her moan and watched her reach down and start rubbing her clit. Lowering myself I felt her little nose push into my ass and the sensation was beyond belief. I rode her little face as hard as I could and we both squirted together.

Two Whores And A Sissy

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He was the cutest little sissy and all he wanted was a mean big sister and a mommy that would encourage the humiliation and abuse. Our sissy came to the right place, Inez was eager to take her and dress her up in full sissy regalia while snapping pictures and posting them on face book. I watched while Inez told her what a pitiful little sissy she was and how much fun it was going to be when they were walking down the hall at school and everyone would be laughing and pointing at the sweet sissy. Sissy’s lip quivered just a bit but Inez didn’t let her cry, suck it up butter cup, this is just the beginning. Inez pulled down Sissy’s frilly panties and took out the razor so she could shave sissy clean, then she put sissy’s clit in a pretty pink bow and turned her around before shoving a rainbow colored my little pony but plug into her tight little sissy pussy. While sissy was on all fours she put a pony harness on her and took a picture before she mounted sissy and took her for a ride right out the front door to check the mail…..good thing Inez couldn’t see that quivering lip.

I Understand

kinky phone sex darlaNot many people understand the life of a Sissy.How hard it is for them every day to live in a world that they don’t feel comfortable in. Having to talk like a man, dress like a man, act like a man. When inside all they want to do is look and feel pretty. To be able to dress in beautiful clothes and speak in their sweet tender voices. To be able to wear pretty jewelry and put on makeup. To be able to wear heels and do their nails. To be able to prance and twirl and curtsy. To be just like the beautiful women that are all around them like the delicate flower longing to bloom and show their beauty on a bright spring day. Longing to emerge from their cocoons and spread their wings to fly like the brilliantly colored butterflies that they are. My heart aches for each and every one of them that has to pretend day in and day out and be careful who they show their true selves to. Cum to mommy where it is safe, my sweet, I understand.

Harley Loves Sissy

mommy phone sex sissyHarley has seen her favorite Sissy in all her glory on her shopping spree. Harley loves that blue dress and dreams of having sexy legs like her favorite Sissy. So mommy and Harley are spending the day looking through all the Sissy pictures we can find for inspiration for a shopping spree of our own, Harley is taking notes and making a shopping list.incest phone sex sissyWe are going to try to buy the exact same outfits that Sissy has for Harley and then next weekend we are going to start our Sissy day marathon and Harley and I are going to go out in public, just like Sissy every Saturday until Harley has had a chance to wear each and every out fit. Harley is so excited about being able to emulate Sissy that she is driving me crazy with all the chatter and nervous energy.kinky phone sex sissy

Sexy Mommy Rendezvous

sexy mommy darlaWhen we have our sexy mommy rendezvous we ravish each others bodies. We spend hours just touching and kissing building the flames of our desire until it is a raging inferno that can only be extinguished with unbridled passion and lust. Our time together is never short lived and it amazes me that Harley sits and watches quietly while rubbing her little clitty through her beautiful silk panties. She always dresses extra special for mommy and her friend like a good little sissy, a pair of mommy’s musky panties in one hand that she holds to her face, inhaling the scent as she watches the show. She makes mess after mess in her silk panties and never leaves her vantage point, watching wide eyed, We always let him play clean up when we are over and let him buckle the strap-ons of his choice on us so that we can fuck his tight little cunny and make him squirty squirt all over. For now he is mommy’s sweet little sissy but some day he is going to make someone a wonderful forever sissy.

Grammy’s Little Treat

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I caught my grandson rummaging in my panty drawer today. I asked him what the hell he was doing and he said ” Grammy, I wanna be a girl for Halloween and you are the sexiest girl I know.” What could I say to the little bastard? I decided to help him become a sissy boy. I had always suspected that he had feminine ways.
I picked out a frilly top and mini skirt and a pair of slutty heels. We had fun trying to stuff one of my bras for him to wear. Next, I did his make-up and hair. Damned if the little fucker didn’t make one sexy whore. My evil mind wanted to pimp him out. With his tight little body and virgin ass-pussy, he was worth a fortune to my P-friends. My imagination got carried away as I imagined introducing him to his first cock, showing him the proper way to eat man-meat. I’d get on my knees and lick that little asshole until it was good and sloppy before allowing some older man to pop his butt-cherry. My fingers slid into my pussy as I pictured him being penetrated. “Oh Gram, that feels so good.” he’d moan, as a fat penis rammed him hard. I’d place him on his back, push his legs back and allow you to slide into that boy-cunt. His penis would be standing straight up and I’d reach out to stroke it while your meatstick slid back into his slippery hole. Soon you’d both be moaning as you filled up his cum dumpster and he shot his cum unto his belly.
And like a good Grammy, I’d be there to clean up the mess, lovingly lapping the jizz from both of you.
Wow, what a Halloween dream!!! I can’t wait until he gets home from trick-or-treating tonight. We’ll explore this need to be a sissy and see where it goes. My pussy is twitching just thinking about it. Care to share in the treats?

family fun phone sex

Sister Fucking with My Sissy Brother

sister fuckingSister fucking isn’t what you would expect in my family. My incestuous ways goes back to being a little girl in Canada. Before I fucked my sons, I fucked my brother. When I say I fucked him, I mean I fucked him, usually with a strap-on. My brother was a sissy. Your typical momma’s boy. Raised by a single mother with 4 older sisters; easy to understand how he got that way. I took it upon myself to toughen him up a bit. All the nights I fucked his back door with my strap on, sat on his face smothering him with my pussy and fe.d him my feet made him soft not strong. Essentially, I created another sister.

kinky phone sexHe paid me a visit last weekend, and even my sons made fun of him. They called him Aunt Mark. I got to show my sons how we treat sissies and subbies in our family. As I was sitting on Aunt Mark’s face, making him clean up his nephews’ spunk in my pussy, the boys started circle jerking on him. It was such a site to see. Three boys more than half his age, with bigger dicks taunting and teasing him about his sissy click He was enjoying the humiliation. It made him lick my sloppy wet pussy faster. My son’s were going to cum on their Aunt, but my eldest boy thought it would be fun to drop their loads in my ass and make her scope it out with her tongue.

sissy phone sexMy sons got hard again watching Aunt Mark eat their cum out of her sister’s shitter. I pretty much farted that boy seed out all over his face, which made my boys hard again. I let them cum in their Aunt Mark’s mouth this time. My sons used her all weekend as a slave. They will use you too if you have a worthless pecker and are a momma’s boy!

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Adoption with Kathy

Mommy phone sex

I love taking in stray whores.

They come to me looking for work.

I clean them up and fuck them for free.

I get them working for me and pay them to fuck other men!

I love adopting my little whores so much I went and adopted myself a son.

I love my sweet son.

He is treated like a sweet little angle.

I put him in diapers, give him bottles and he even sucks his new mommies titties.

I love cleaning his ass after he uses his diaper.

Ageplay phone sex

After he gets all cleaned up this naughty mommy sucks his dick.

I love sucking his balls and his cock.

His dick is so big I even ride him.

He is such  a good son.

I love my sissy son.

He lets mommy dress him up like a little baby whore.

He loves it when mommy puts him in a diaper.

My big sissy son loves to be treated like an adult-baby!

 

He Is So Shy

kinky phone sex camillaHe wanted to be my little girl so badly. I could see the longing in his eyes when he watched me get dressed and put on my make up. Finally I took him in my lap and wrapped my arms around him. I let him place his head on my chest as he sat without saying a word. He just sat and listened to my heart beat. We sat like that for a long time before I took his hand and led him to my room. Sitting him on my vanity stool i stood behind him and began combing his hair while I told him that inside there was a beautiful princess longing to get out. I continued to quietly tell him that I wanted him to be my special girl and before long he began to come out of his shell and she was born. Her eyes lit up like a Christmas tree when I took out the make up and began to transform my sweet princess into what she longed to be. She began talking little by little as I led her to my drawers and told her she could not only pick out anything she wanted but she could keep it too. Soon she was babbling on and telling me all of her hearts desires I am working on making each and every one of them come true for my beautiful, blossoming sissy princess. 

Picture Day

mommy phone sex darlaHarley is so cute. He wanted to play photographer and take sexy pictures of his hot mommy. As soon as he told me what he wanted to do my pussy got so fucking wet. He was in charge of the entire session. He told me to undress so he could get some good pictures of me naked. He told me how he wanted me to touch myself all while he snapped pictures. He had a box sitting next to him. He reached in and pulled out a pair of my sexiest panties and made me put them on for him. He had me pull them up and into my pussy all the while my pussy is pumping juice while he snaps pictures. He has me take the panties off and makes me put on a pair of pantyhose. I love the way he tells me what to do while he takes more pictures. I can’t help but be turned on by his hard dick and I start to cum hard in my pantyhose. I am begging him for the shoot to be over so he can lick my pussy clean. I need to feel his lips on me and I need to put my mouth on him. I love my sweet little sissy boy.