Category: Sissy training

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


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

Rape Phone Sex Fantasies

rape phone sex fantasies darlaIt was Harley’s turn to pick out the porn last weekend. He picked out a something that is different from anything he ever picked, a torture porn movie. When I asked him if he was sure that was what he wanted he assured me that is was. When I asked him why he told me that he had just liked it and he wanted to see more. We went home and watched the flick and he was hornier then I had ever seen him. Being a good mommy I had to satisfy his need. I called one of my friends and arranged for him to come over in the middle of the night, dressed all in black with a mask. I let him borrow the porn so he could re-enact as many of the scenes as possible. It was all set. I waited up and when I heard him come in I slipped out of bed with my recorder and stood in the shadows. Of course, Harley had no clue and was crying and yelling for me which made my pussy wetter than ever as I recorded it all for us to watch later. When it was all over I went to him and held his shaking body to me as I comforted him while he sobbed. Rubbing his clitty as he sucked my nipples and clung to me. The entire thing was the most erotic experience I have ever had.

A New Tradition

mommy phone sex darlaValentine’s Day is on a Sunday this year. I always buy Harley chocolates, some cute panties and take him to a movie on Valentine’s Day. but he is getting older and it is time we start a new tradition.

This year I am getting him some pretty panties and lingerie, but instead of chocolates and a movie, I am buying submissive bondage toys.  Valentine’s Day will be the start of a weekly tradition that I will call Submissive Sundays.

Of course our first Submissive Sunday/ Valentine’s Day is going to be just Harley and I and we will take turns being submissive and dominant. but the weeks to come are going to hold a wide variety of submission and bondage lessons as well as partners that will join us as we celebrate our Submissive Sundays.

Just thinking about all the possibilities as I shop for handcuffs and blind folds, whips and nipple clamps there are so many things to choose from and it all has me so horny! I never realized how many toys there are for bondage and submission. I found the cutest little cage for Harly’s little clitty dick. In fairness I just had to pick up a cage for mommy’s pussy. I even bought us matching leather outfits so that we look the part as well!

Starting a new tradition is always fun and the anticipation of all the things that can be incorporated into a new way of exploring our special mother/ son / sissy bond is just as much fun as bringing all my ideas to fruition. I can’t wait to get started and to progress from it being just us to inviting friends over to share Submissive Sunday with us! They say the more the merrier and we do love to be a merry mommy and her sweet sissy.

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Football Fuckfest Weekend!!

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I can barely wait for the Super Bowl Party. Denver Broncos all the way!!! I’ve invited a bunch of my guys over for some football fun. Nothing like a room of testosterone to make a pussy purr. Boy, do I have a half-time surprise for them. I’ve dressed up my little sissy faggot to entertain them. She and I are planning to do a little coming out party to announce how much she loves cock. I bet that will get their attention for sure. My sissy is such a flirt. She loves to dress up in lavender satin and high heels. Her cock is average size but I’m quite sure my boys will enjoy it. It makes me wet to think that I can bring some of these straight, married guys over to the wild side. Uncle Joe and Daddy will be there too, for some family fun time, along with the cousins.I know these horny old dogs so well.

I can picture it already. Sissy and I will do some dirty dancing and grinding to get the guys started. The beer is flowing. Cocks are gonna come out as I force Sissy to service my pussy right in front of them. One of them will try to move in on the action only to find his face stuffed full of sissy cock. My horny boys won’t be able to resist. Sissy and I will both be getting our pussies reamed as the 3rd quarter starts. It sounds like the perfect game begging for that touchdown, both hands on the floor, ass in the air. Tackle me, lovers, and pile on. Winner gets all the pussy he can handle. And the party really gets started when the game ends. It’s a Football Fuckfest Weekend and Mama can’t wait!!