Category: Sissy training

Here Cums Sissy Cottontail

kinky phone sex darlaLet me share Harley’s favorite bed time story with you.

Once upon a time there was a boy. He always knew he was different, not like the other boys. He would sneak into his mommy’s room and admire all her pretty things. He longed to wear the pretty jewelry and have beautiful dresses just like hers to wear. He would daydream about being able to dress up and go out into the world as a pretty girl. Time passed and he grew up, got married, had girls of his own and worked as big time lawyer. But he couldn’t deny the inner sissy fighting to get out. Yearning for a Mistress he started calling phone sex lines and soon found Princess Levi, the Mistress of his dreams. Finally he became the Sissy he had always dreamed of. Mistress Levi gave Sissy permission to dress in frilly dresses and to wear jingly jangly bracelets and pretty gold hoop earrings. She sent Sissy out once a month for a special day of prancing around in public. A day of humiliation and shame just as she deserved. Sissy grew to love her Mistress so much that she became a piggy pet and the Tinkerbell Transvestite mascot for all Mistress’s girlies at Fuckalicious, Finally Sissy had a home and lived happily ever after being outed as the Fairy Faggot she had always been.

Happy Easter Sissy Cottontail!sissy training sissy

Submissive phone sex with Sidney

Submissive phone sex

My brother likes this tiny little pussy and ass. He loves to lick me from my clitty all the way down to my cute little starfish hole. He loves tongue fucking both of my holes! He rubs my little clitty  with his fingers. I love how he works my clit and my pussy hole at the same time as he tongue fucks my asshole! Getting me ready for his cock. He loves it when I suck on his cock as he does this to me. I sucking his cock getting him shiny and wet with my spit. When he is ready to fuck my tight little asshole, he rubs the head of his cock all over that little starfish hole. It makes my pussy throb when he teases my asshole. I spread my ass cheeks open showing him my hole as he slides his cock inside of me. Stretching my tight asshole open inch by inch makes me moan. He slapped my ass as he slides his cock in deeper tonight tight asshole. I love getting butt fucked by brother. Then cleaning his cock off with my mouth after he fucked my dirty little hole.

Photo Finish

kinky phone sex darla1I love when he comes over and takes pictures of me. As an aspiring photographer he likes to play with light and angles and things and I love being his subject. There is something about it that makes my pussy wetter then hell Add to the mix the fact that he is very fem and I just can’t get enough. I can’t help that I love men that are feminine, shy, soft spoken. I fantasize about what my boy is going to be like when he gets older and my mind wonders in so many different directions. Standing here with cum soaking my third pair of panties so far and we haven’t even been shooting for an hour, I know this is going to be a long night for me followed by the usual get together between him and Harley that I get to shoot.

Happy St. Patrick’s Day!!!!

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Kiss me, I’m Irish. Aren’t you excited it’s nearly St Patrick’s Day? I love those parties and drinking green beer. Corned beef and cabbage and leprechauns. I’m gonna dress up in my favorite skirt, the one that shows off my big round ass. Going to go find me some cock and let him fuck my puckered hole. I have to laugh. Can you imagine ass fucking after a night of drinking beer and eating cabbage? Kinda gross but erotic at the same time. My older son really used to get off on fucking me in the ass and making me fart on him. He said it felt amazing…that warm blast of air and the way my asshole tightened up. An ass like mine is made to be used that way. It’s like a huge cushion,a real lucky charm, made to be grabbed, squeezed, slapped, and rode hard. Grab double handfulls of cheek as you slide your throbbing cock inside, pushing as I gasp. Don’t stop now. I want my ass fucked full of cum. Can you handle a dirty older woman like me? It’ll be your LUCKY day when this hot momma gets through with you.

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Humiliation Style Spring Cleaning

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Mommy woke me up Sunday with one goal in mind for the day and I was so not having it. Spring Cleaning? What the fuck is that? Why should I have to clean…?! I immediately thought of a solution…Why not make someone below Mommy and I to clean it? That’s right! Daddy! I laughed and told Mommy my idea, and she was pleased as we went to tell him. We wanted to dress Daddy up Good. We really wanted him to be all cute while doing the spring cleaning…meanwhile Mommy and I planned to sit out by the pool in our bikinis. Just waiting for our friends to come over. These are some of our favorite friends, they all have 12 + inch cocks and they’re so big and magnificent that no one could refuse them. Mommy and I know it’s hard for Daddy to keep cleaning when he can see his wife and daughter getting gangbanged by the thickest dicks you’ve ever seen. Daddy will just know that his is too small and worthless and all he can do is clean like a little pathetic tiny cocked loser. Meanwhile Mommy’s putting her time with some real men to good use and I am following suit, being whores together is our favorite pastime – that and tormenting and humiliating Daddy!

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Selling Panties

kinky phone sex darla1I decided to start saving my cum soaked panties in zip lock baggies. I like to smell them while I have a big hard vibrator shoved up my pussy and I am fucking it hard. It takes me right over the edge and makes me cum like crazy. Harley loves to lick them and smell them and it makes her little clitty hard as a rock. I have caught her licking them while one of my dildos are deep in her sweet little pussy. The sight sent a rush of hot cum flowing from my hot cunt, I had a sip lock handy for the fresh load.

Harley has started cumming in her panties too. I keep her panties in the little sandwich zip locks. Cut little pink panties, hello kitty panties, Dora The Explorer panties and lacy girlie panties, all soaked in her cum and sitting on the shelf.

Recently a friend of mine saw the panties and asked what they were. When I told him he said he wanted a pair and would be willing to buy them. The idea made me horny as hell. There was something erotic about knowing that someone was turned on and enjoying mine or Harley’s cum soaked panties.

I have been selling them on a regular basis now and have been able to supplement my income very nicely.mommy phone sex specials

Spring Is Sissy Time

kinky phone sex SissySpring is upon us and we need our Sissy Bunny to bring us brightly colored eggs and lots of Easter candy. It’s time for Sissy to put on her pretty, tight fitting, pink Easter Bunny custom with it’s pretty white and fluffy cotton tail and big pink bunny ears,

“Here comes Sissy Cotton Tail, Hoppin down the fairy trail, Hippity Hoppity Sissy’s on her way”

Oh how my heart skips a beat as I wait to see all the pictures of Sissy Bunny out and about for the holiday making it special for all that feast their eyes upon her. How awesome it is going to be for her to watch people point and laugh and take pictures of the Sissy Bunny!

Sissy Bunny is my favorite thing about Spring!mommy phone sex darla1

Jenny and Sissy’s Day Out

sissy trainingI’m Sissy. Today I met up with my new friend, Jenny, to see if she could teach me some sexy new moves. She is just a teen and I figured Goddess Levi wouldn’t mind if I got some lessons from her. Jenny giggled when she saw me. “OMG, Sissy, we’re gonna have soooo much fun today.” We’re gonna take some sexy new pics and then you’re going to cheerleading practice with me. The football players will love you. Then we’re going out in public and shake our shit.
Jenny was a ball of sexy teen energy. She did my make-up perfectly and we both got dressed up in lace. Of course, she made me her pay piggy and I bought her a hot new outfit. That’s what I do best, getting used. Miss Levi will be proud.
Jenny was not one bit shy. She paraded me like a flaming queen, introducing me as her Fairy Godmother. She made me spin, flirt, and show my panties. She even matched me by doing the same.

kinky phone sexThen we went to cheerleading practice where she had a surprise for me, my very own cheerleading uniform complete with lacy panties. It was hard work and a crowd gathered to watch me kick and do splits with the girls. The humiliation rained down on me, making me horny. It was so much fun being a teenage sissy.
We spent the day in public, making a great documentary about life as a sissy. I told her about how I craved the humiliation and the pain, the revulsion in people’s eyes, and my failure as a man.
Jenny was the best. She knows my secret now and she’ll probably use it to blackmail me later. They all do. Best of all, she has a date tonight and has invited me to come along to ASSist her. My little penis is so hard just thinking about it. I love being a helpful sissy and a closet faggot. Soon, everyone will know the truth about me!!!

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Sissy Training With Mommy


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Mommy and I have a ton of experience with loser wannabe men. I mean, my Daddy is a cucky loser with a tiny thing that he likes to call a cock! He is always begging to watch me and Mommy and to play too but we would never allow that…so I’d say we have a little bit of humiliation department. A bit of humiliation for this sissy faggot we all like to laugh about. Mommy and I do best as a team, laughing at her and making her jump through hoops for us. We enjoy doing sissy training every other day…Sissy never gets a break from us but we know she loves it. How could she resist us? We’re hot and sexy and we’re pushing her around making her into our little bitch – our personal entertainment, maid and money source all in one! It almost sounds like Daddy all over again because this shameful sissy has a tiny itty bitty cock too! I mean, I personally wouldn’t call it a cock it’s so small…but it’s definitely funny to laugh at! Mommy makes him dress up like a little bunny and serve us while we giggle and laugh and humiliate this sissy. She needs her sissy training and we are going to give it to her!  sissy phone sex

Sissylicious

kinky phone sex SissyHarley came to me this morning and asked me how his favorite Sissy can go from a rough and tumble, fight it out, high profiled lawyer by day to a sweet and loving sissy at night. I never really thought about that one so I didn’t have an answer for him. One thing is for sure it does show my sissy boy that he can be successful as a fake man while still holding on to his beautiful inner sissy.What a beautiful lesson for Sissy to teach my little one. In honor of our favorite Sissy Harley is being a fake boy all day and tonight he will transform into a sissy with jingly jangly bracelets and big gold hoop earnings. Tonight I make him walk around with a lump of shame just like our favorite poo poo pansy and I will make him rub his clitty with it. I haven’t decided if I will let him squirty squirt or not. But I do know he will get a good dose of humiliation and shame just like our Fairy Faggot Sissy. I love that Harley wants to be just like Sissy Michael, our very own Piggy Pet, Tinkerbell Transvestite. We love you Sissy and we know you love us too!mommy phone sex sissy