Category: Crossdressing Phone Sex

Sissy schools phone sex: Class in Session

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We are going to hold a special session today during sissy schools phone sex. That’s right you are going back to school. I’m going to be the head master and I have taken a special interest in you lately. Everybody has to dress up like a girl everyday but I have assigned you a special outfit. It is a whore red push up bra which I require you to stuff and a matching red mesh see through G-strong with your little clitty tucked for me. You always report to my office before school at seven A.M sharp so I can teach you how to do your makeup. Blue eyeshadow and bright red lipstick with heavy eyeliner makes you look like the good whore you are. Then I lead you into a bright classroom with cameras on the wall. I record everything you do to record it as black mail. For the first lesson of the day, you sit in an uneven chair and write “I am a sissy whore bitch” over and over again. I only let you give it to me and stop writing when you have written 500 sentences. It takes you about two hours. Your hands are cramping and are in pain by the time you are done. You see me smile. You know that you being in pain brings me pleasure. For the second lesson, you get on your knees and go suck the dildo on the wall. Its 10 inches and we are working on having you deep throat it all. So far you can only take 8 inches without gagging and almost throwing up but we are getting there. Soon you will be an expert cocksucker. For the last lesson of the day, I sit on your face until you are begging me to let you breathe again. Once I soak you in my pussy juices, I let you go home. I’ll see you tomorrow for a new lesson.

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Late Night Walmart Surprise

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I was late night shopping at a popular store. I had just stopped by on my way from the club. Dressed in a sexy short denim skirt and a western blouse that showed off my tits, I strutted through the store. I needed mixers for a few more drinks so off to the soda pop aisle I went. When I got there, I was dismayed to find that the kind I needed was almost gone. Only a few bottles remained on the back of the top rack. Of course, there were no employees anywhere to assist me. Then I spotted him. A big old American dream boy at least 6’6″. I smiled and waited for him to approach. “Excuse me sir, can you help a girl out and get me a bottle of ginger ale? He looked me up and down and smiled. “Certainly, ma’am. Be glad to.”
Well, I expected him to reach up and grab one, but instead he picks me up, hands around my small waist so I can reach one. I felt his hands slide along my entire body as he put me down. “What’s up tonight?” he asked. “Just going home for a few drinks.” I told him. “Care to join me?”
I won’t share all of the juicy details but he liked what he found under that denim skirt. He slurped my big cock like a pro. And then he picked me up again, just like at the grocery store. But this time, I was naked, and he slid me down his body, impaling my boy-pussy with his large thick cock. I think I’ll ask strangers for help more often!!

I’ve Got Something Special…

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Daddy’s little boy I used to  be till I  became Daddy’s little girl…and all of a sudden I was both. I was that special something everyone wants but doesn’t have…my Daddy was a very lucky Daddy. His ass was sore as mine was, and my tits were the perfect thing to fuck too. I knew Daddy would never want anything else after having this kind of special treatment. Ever since my tits sprouted Daddy’s been hooked. Everything he ever wanted and more in one special sex package. I am the one that fucks his ass till it pools up with cum…and he fucks my mouth and tits till I am begging for more. I am a horny little boygirl that needs to show you a special hard surprise of mine. Try and taste mine and see how it is throbbing in your mouth. Exactly how you imagined it would be…Just ask Daddy he’s been playing with my cock since before it was big and hard and fuckable. He just found it touchable and suckable, his special lil boy. And then my tits came and so did he (on them) and I was his sweet sexy girl. I wouldn’t have it any other way…you see – you really can have it all.

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Training Her Slave

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Sometimes I try to challenge myself to do good things and since Random Acts of Kindness Day is tomorrow, I’ve decided to help a good friend of mine. She’s more of a hobby mistress but lately she has been having trouble breaking in this new slave. She told me everything about him. He loves dressing like a faggot and dreams about big black cock. She asked me to help breaking him in since I love and have trained quite a few sissies. He doesn’t even know what’s going. I prepared my house for when he comes tomorrow. I blocked out an area in my house with gates so he feels trapped. I want to fully break him in. He is going to have to ask my permission for anything even to piss or shit. We’ll see if I let him. Maybe if he doesn’t go to the bathroom in his crate, he can earn a reward to wear a really cute sissy outfit.

Aggressively Prowling For Dick

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After a long, and most times, FRUSTRATING day at the office helping other people work through their issues, sometimes I need to go out and hunt for my meals, so to speak.

I am a Class A Man-Eater, and I will devour your entire being and spit you out when I’m done. I am looking to my pleasure alone, if you perform well then I can promise you the ride of your life!

I’ll have so much fun dressing you in my lacy panties and negligees, making you prance around in my 6in stiletto heels all made up like a pretty lil’ whore. You’d enjoy being my little sissy boy and pleasing your mistress at any cost, even your very soul.

I’ll ride your rod to oblivion, crushing your balls in an exquisite vice of pleasure while my dripping wet cunt milks your orgasm out of your sated body. I’m not done with you yet, while I continue to ride your unwilling prick I’m smothering you with my tits, getting myself off with my sensitive nipples covering your screams.

Dinner is served!

Boys will be girls.

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Spending the day with Sissy Michael was just marvelous. Just us two girls going out to tea in our frilliest of outfits. We flirted and flounced. We shook those tail feathers, girl, cause if you got it, flaunt it. Just because we have cocks under those panties don’t make us any less of hot girls. Michael does need to get her some fine boobs like mine though so she can show that cleavage.
I guess I’m blessed with self confidence more than poor Sissy. She said that her New Year’s resolution was to be a permanent punishment pansy. I said, “Whatever makes your panties wet, girl. You get off on having people laugh, go ahead.” A good tranny never judges anothers needs even when they are all fucked up. ‘Ol sissy would make a hot older woman, if she would quit the humiliation gig. But, then again, that’s her charm.
I wish I could change her mind though. She actually told me that she begged and pleaded for humiliation and has to even PAY for it. I said, “Fuck that. Someone would be paying me for that right. Big bucks.”

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Anyway, we spent the afternoon trying on each others hot tranny clothes. Mine are more racy while hers lean more towards fluff, cotton candy, and piggy pink. It was strange how I changed when I wore her clothes. I felt “different” and more demure. I’m not saying that she deserves public ridicule and perpetual teasing & sissy shame, but that wardrobe sure invites it. I did give her a lipstick in pussy pink and some sexy perfume.
Anyway, I love our girls day out, Michael, and hope we can meet up soon. I’m doing a tranny fashion show and I know a crowd who would love to humiliate you and make you into the pay piggy that I know you really are. Of course, I’ll never tell. Hope you love the butt plug I slipped in your purse!!!

 

New Year’s Punnishment

sissy phone sexMistress Levi has informed us that our Piggy Pet is in need of attention. I love when Levi sends requests for Sissy’s public humiliation. This time Sissy has earned the title of our New Years Permanent Punishment Pansy. We all know that she begged and pleaded for humiliation and even has to pay for it. We also all know that once she receives what she asked for she will beg and plead for mercy. Silly Sissy will never learn that you get what you ask for from a group of superior females that learned from the best, Mistress Levi. Our Tinkerbell Transvestite deserves public ridicule, perpetual teasing and sissy shame. Come to think of it I think 2016 should be The Year Of Sissy Michael here at WBMT.  The Year of intense humiliation and shame. The Year of  The Piggy Pet and paying for the deserved teasing and taunting by the wonderful women of  WBMT. The Year of the Final Outing, the one that will put an end to the fake man life of our Pansy Princess. We all know that is really what she wants any way Who better to give her the dream she has always dreamed of then us? We can be like her Blue Fairy from Pinocchio and instead of making our Silly Sissy a real boy, we will help her out of the closet so she can be a real girl forever and ever! Your welcome Sissy.adult phone chat melinda1

Movie Time

adult phone chat zettaWe decided to go see the new Star Wars movie that has been all the rage. When we got home I was so horny. I dressed up in my black boots with some electrical tape over my nipples and played an evil vileness from a far away star. I took him captive in his pretty little dress and made her my sissy slave. Cracking my whip I shoved her to her knees and made her service me. She loved sucking my alien dick and begged me to give her all my alien cum. But I wasn’t ready to give my captive anything just yet. I told her I planned on breeding her and we would have a half sissy half alien offspring. Just the words made my little sissy cum all in her pretty panties. Of course she had to be punished.

Teacher’s Pet

adult phone chat zettaMost of us have dreamed of being the teacher’s pet. The favorite in the class. The one that gets away with most anything. I too always wanted to be the teacher’s pet. Only I wanted to REALLY be his pet. I wanted him to put a collar and leash on me and walk me around the room. I wanted to get on all fours for him and have him spank me with a whip before mounting me and shoving his cock in me. I would dream of it at night. I guess that is where the fetish began for me. I would love to hear about some of your kinkier fetishes. The ones you never share with any one because they just would never understand. I will understand trust me, i have a few of them myself!

Shopping for a sissy bitch

adult phone chat parisGet in! We’re going shopping. I know you’ve been stealing things from my closet so it’s time to dress you up. We’re going to find the cutest clothes for my pet sissy. The mall is wonderful places to take you that way you get wear the clothes around. I want to stop at the fetish store to get a cute little collar for you. It’s going to have shiny gems and adore the name “BITCH” in the middle. Everyone is going to know you belong to me and you love dressing up for me! You love knowing what a little faggot you are, don’t you?
I can’t wait to pick out some pink little miniskirts for you. Oh! Victoria Secret has the best bras. You’re going to love it. We are going to need to get you fitted by a sales lady. Aw, babe. Don’t be embarrassed. You need to be proud that you’re my little sissy bitch. It’s not your fault you have a small clit and love to dress up. Do not worry, by the time we are done, everyone in town will know exactly what you are. My pathetic little clitty pet!