Tag: sissy training

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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Happy Groundhog Day. Goodbye Winter Woolies.

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Today is that stupid Yankee rodent day. I hate fucking rat looking creatures but daddy says I must respect tradition. His groundhog day tradition is very much his own and it is so much more fun than watching for a shadow. Our family tradition is that on Feb 2nd Daddy will come around and check his girls pussies. If her pussy hair is thick and winter-nasty, she doesn’t get any Daddy cock. If it’s all smooth and waxed, her eager little beaver gets some winter wood. Of course, I’m joking.
Feb 2 does mean something though. It means it’s almost Springtime and time for those sweats to be packed up and all of that hair to be gone. Bikini season is right around the corner. That means you too, crossdressers and sissies. Time for the tanning bed and the wax. If you’re gonna compete for the finest cock out there, you’ve gotta get your game on.
Let me be your sissy trainer as we do our female hygiene. I can teach you step by step the best way to shave those balls, tweeze those anal hairs, get rid of that winter butt acne, and make you into an enticing and tasty little whore. Allow me to coach you. I can even pick out your lingerie and panties for you from my own wardrobe. I may be young but I know what big Daddy loves. Let me be your new best friend and teach you how to be a sexy girl.

New Lingerie for my Sissy

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I couldn’t resist. V-day is almost here and I just love new lingerie. I stopped by the new VS store just to see what they had on display. Whoa, my pussy got wet just looking at the stuff. It was hotter than a panty boys dream in there. Even the cashier was looking good enough to eat in a bustier. She looked my body up and down and said she had just the thing for me. “It’ll make your man stand at attention.” she smiled. She led me down rows of silky lacy things. Matching bras and gartered surprises. Silk stockings in an array of colors. A smorgasbord of delights for the senses. Sultry perfumes. Mmmmm, I was getting giddy with desire.
And then we were there. It was a secret world tucked in the back of my mind. I was surrounded by men admiring my lace clad body. They reached for me and I felt the heat fly from their fingertips. My body was caressed by unseen fingers that made my nipples hard and my pussy slick. One beckoned me, bringing my face to his cock. I opened for him and tasted the sweetness of his pre-cum. Another lifted me, pressing me against the wall. I felt the tip of his penis touch my slit and I moaned. A shudder ran through my body and I cried out for what I needed.
Suddenly, I was back on the lingerie aisle, alone, flushed, holding a silk camisole and matching panties in my hand. I knew I had to buy it. Somewhere in Victoria’s Secret I had discovered a whole new dimension into my sexuality. I would be a goddess for Valentine’s Day. Welcome, all you panty lovers and sissy boys. This year is gonna be different. Let me show you the selection of fine panties that I have for you for Valentine’s Day. It’s the biggest panty sale of the year. Don’t miss the fun.

Bubba is my new sissy.

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Just a small runner in my pantyhose and my day was ruined. Now I had to pull them off and put on another pair, trying not to tear the new ones with my freshly manicured nails. I tossed the torn offenders in the trash and headed out the door to class.
I got home a bit early and the house was quiet except for a strange little sound, like a youngster giggling. Walking past the kitchen, I noticed that my torn panty hose were no longer in the trash. This was too weird. I snuck upstairs, thinking that maybe someone had broke in. I moved cautiously down the hall, hearing the falsetto getting louder. Then it hit me!!! Bubba had taken my damaged pantyhose from the trash and was up to something. I peeked through the door and nearly fell over. That asshole had pulled my pantyhose on and was wearing a pair of my dirty panties on top. He has also managed to stuff his fat feet into my favorite heels and was strutting like a faggot in heat. I threw the door open and he nearly fell over. His cock hung limply through a tear in the panty hose, allowing him access to it. I could tell that he’d been jerking off all day.
“So, you wanna be a sexy bitch, Billy?” I tried to act tough. “How bout I tell Daddy what you did today?” He began to whimper. “Please, sissy, I just want to be a girl. I’m not like other boys. I’m a panty boy, a faggot bottom.” I turned white. How did I miss this? I went to him and hugged him. I had a sister and she needed cock. I ran to my room and returned with my vibrator. “Come here, babe. I wanna break you in.” The look on his face was priceless. His cock began to rise as I lubed up the thick dildo.
We spent the rest of the day in his room. I stretched his new boy-pussy and taught him to suck cock. Finally, I fucked him up the ass as he jerked off. It’s gonna be so much fun having a new playmate to dress up and fuck. I can barely wait until he gets his first piece of real man-meat served right up the ass. I’ll be right there to suck the cum from his newly violated pussy. It’s what a good sister does for her cock-loving Bubba.

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A fun night out with “Allison.”

kinky phone sexWatching him flounce across the floor made me giggle. He really needed a girl like me to help him. “Oh, Allison, you are doing it all wrong.” I said, tucking his cock back into his panties. “If you wanna learn to suck cock, you need some lessons.” Allison, of course, was all fucked up and called me a bitch. I leaned in closely and whispered in her ear. “Baby, you know you want this big dick, right? Let me show you how to get it.” I approached the big bull nigga and slid my hand into his baggy pants. He flashed a gold tooth and looked at us. “Mmmmm, fucking white meat. You gonna give Daddy some head?” I took at Allison and she flushed red, obviously high and horny. I nodded towards the back room and he followed us. “Ok, Allison, here’s your chance to get some BBC.”She whimpered a bit as I rubbed the blacksnake against her cheek. Allison opened wide and a sprinkled a little meth on the cock and shoved it in. I heard her gurgle as the big nigga began to violate her face. Fondling his nutsac, I urged him to feed my bitch. It was all Allison could do to keep up with the pistoning meatstick that pounded her face. I reached into her panties and stroked her cock as she got her fill of man meat. Our black joystick began to moan. “Eat my cum, you white ho. Swallow it.” Allison’s hot little mouth was filled with gobs of fuck sauce as she humped her own load into my hand. I licked it clean. Her jizz was delicious. Knowing that I had helped my friend get some cum really made my night. I was juiced and ready to find some of my own now. Allison and I were hot to trot tonight!!!

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I Am Honored

kinky phone sex darlaShe took her time finding just the right one and that one was me. She just wants to serve me in every way she can. I am so flattered that I will have her at my beck and call at all times. So far she has been such a good sissy that I went out and bought her three pretty new dresses with matching panties and accessories and three new nighties. Tonight she cooked me a wonderful meal, made sure I was comfortable after diner while she cleaned up and then took me to my candle lite room where she  laid me down and gave me the best massage and pussy licking ever.  it was the most relaxing and pampering evening! Now that my pussy has been licked clean and I am drifting off to sleep, I am thinking about what tomorrow will bring.