Tag: sissy training

Grandma phone sex and her cucky son

 

“Shake them big titties. Let me fuck those stripper tits.” he moaned as he slid his cock back and forth between my watermelon breasts. I may be a grandma but I can still rock that cock!!! I love them young. My son still keeps Mama well fucked but I need more. I have a big cock fetish. Big, thick and juicy. I don’t discriminate on race or age. Bring me a small dick and I’ll put you in panties and cuckold that ass.

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I remember the first time I saw you and your jumbo cock. You were a bit shy and I could tell you weren’t experienced. I made the first move, placing my hand on your thigh. Once you warmed up, though, it was like holy fuck. I pulled that fuck-monster out of your pants and my furry cunt got all wet. I wrapped my lips around it and tasted your pre-cum. You were grabbing my hair, trying to push the entire thing down my throat. I slurped and gagged, trying to keep up with your thrusts.  “Show me your pussy, mama.” you whispered. I kicked off my leggings and you gasped when you saw my wooly bush. Most young girls wax that hair off so I knew that you’d never seen one like mine before. I stretched out on the couch and spread my fuzzy lips. You were on me in seconds, pushing that 10 incher into me while you sucked a big tit. I felt your girth stretch me open and I knew I was addicted. It was nothing like my son’s 7 inches. I’d never be satisfied with that again. You began to pound me hard, pushing it in to the hilt. My pussy squirted as I came hard. I felt you began to throb. That beast was gonna blow!!! You began to whimper, “Mommy. Mommy. I need to cum.”

Just then, the door opened and my son walked into the house. Seeing the size of your cock, he sat down into a chair and pulled his small one out. The fun was just getting started.

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

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.

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


2 girl phone sexMommy 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