Category: Sissy training

Mommy sex for diaper boys

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My pussy tingles as your lips touch my breast. What a good boy you are today. I can feel you hungrily suck my milk from my udders. I rock my boy back and forth, planning out the  mommy sex activities for the day. Next is bath time and Mama can’t wait to wash those boy-parts. Soapy little balls and oh my, what a big cock. Let’s get you all rinsed off and dry you all over. Then it’s playtime with Mommy.

Oh, don’t you wish those days were still here. Playtime with Mommy was so much fun, but now you’re too old. Still, when you were a teen you lusted over Mom, hoping to catch a glimpse of bare flesh, a boob, or God forbid, a look at that hairy pussy. jacking your cock in the shower, you imagined her coming in to dry you off like when you were a boy. The feel of her soft hands on your flesh is enough to make you hard all over again. Watching Mom sleep, you imagined pining her down and forcing her to take your large teen cock, magnificent in its glory. She would never touch Daddy again if she ever got a taste of your young meat. Only you could satisfy her. You’d be moaning, “Mommy, oh Mommy, please.” as you poured load after load into her sweet slit.

Mommy bends over in front of you again and you almost blow your load. Does she have panties on? She smiles at you and you wonder if she can read your mind. Does she think of your cock in bed at night when you spasm and moan out loud in your sleep. In your mind, she comes to comfort you, holding your face to her breast again and finally, she gives you what you need. That hot milf pussy.

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Sissy Training my Son

sissy training

My son came to me last night with a strange request. He had been having some homosexual urges and he wanted me to help him explore them and give him some sissy training. We’ve always been very open minded and a sharing family, so I agreed to help. I sent to the store with a list. Panties, lube, and an enema. I bet the cashier was thinking wicked thoughts when she rang him up!!!

We started with the enema. No one wants to mine for poop so you gotta be clean. Once his colon and rectum were cleansed, I brought out my vibrator and the lube. Starting with a small one, I worked him up to an extra large black cock. Still, he wanted more. I began to think he was a greedy little faggot when I brought out my jumbo strap-on. I just rammed it in, making him squeal like a little bitch. Mama is a good sissy trainer but my boy was insatiable. He begged for more and bigger meat. His tight round ass up in the air really got me turned on. I knew exactly what he needed. A good old-fashioned fisting. I closed my fist, looking at it, wondering how much he could take. We were about to find out.

A squirt of lube and I was ready. My hand slid in to my wrist and he didn’t even wince. “More, Mom. More.” he moaned. I pushed farther and farther, halfway up my forearm and it still wasn’t enough. A milky juice began to flow from his asshole with each plunge of my hand. A little more and I was buried to the elbow. His ass was rocking now as he greedily took it all. I slipped my other hand in my panties to diddle my pussy. I was creaming now watching my greedy faggot son get what he needed. My arm was suddenly gripped by his sphincter muscles as his prostate began to twitch. I knew his cock was gonna blow and I had to get out of there. As I pulled my dripping arm from his ass, my horny boy blew a huge load all over himself.

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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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