Category: Sissy Phone Sex

Naughty sissy is getting outed!

sissy phone sex“Hi Everyone, my name is Sissy. And I am a total loser! Want to know why I am such a pathetic sissy?” Well, you see… I must have been a very bad sissy. Sissy is in trouble with Mistress Levi. That must be why she is forced to pay the consequences. Literally. Mistress Levi wants our site sissy’s name in the blog, and I couldn’t be happier to out her. She is the one that is always saying “Please tease me! Giggle at me! Laugh at me! Out me, humiliate me & punish me as I deserve!” Yes Sissy, just as you deserve. You know you want it, you crave the attention of being outed, oh yes you do. We ALL know it. We all fucking love it. Talking about a loser sissy like you and all the silly things you do for a reaction from us beautiful, worship-worthy women. Sissy, don’t you know I have no problem telling the world about you? I don’t need an excuse to tell everyone that Michael is a transvestite mincing and prancing in public for total humiliation and sissy shame!!! Oh, that she is… just a pathetic fake man who loves this shit, eats this shit up because all Sissy wants is someone to talk about her. Someone to out her and tell the world that Michael  is a pathetic pansy crossdresser who is punished with public humiliation for all to see!!! There! There it is sissy, everyone knows what a loser you are…and next time they’ll know about your love for panty pudding too.

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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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Nikita takes an ass pounding.

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I was feeling really horny when I went out this weekend. I wasn’t looking for a date, just someone to eat my cum and relieve the pressure of my full balls. I usually use the ladies room when I go out but the line was so long and I had to piss out a few beers. I decided to hit the men’s room. I was standing at the urinal with my skirt pulled up when this buff dude walked in. He looked a bit confused at first but then his eyes lit up. I smiled and pointed at my cock and he shook his head yes.
He followed me outside to the back of the bar. I could see the huge bulge in his pants and I knew he wanted some cock so bad. I decided to be a lazy slut and just let him fuck me. Use me. Fill me up with cum. He dropped to his knees and gave me the best blow-job ever. He sucked my balls and licked my asshole. My cock was drooling all over my panties and I wanted him bad.
We went out back. He picked me up against the security fence and with no words spoken, he rammed his thick cock right up my boi-pussy. I couldn’t be quiet. I begged for that dick and he was giving it to me hard. Just before he blew that load, I dropped to my knees and he doused me in a gallon of fuck sauce.
He never said a word. I wasn’t satisfied yet though. I went back into the bar, smelling like a well-fucked whore, and looked for my next victim. This time I was doing the fucking!!! Are you ready for my tranny cock?

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Homemade Mud Video for my Slave

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This week has been horrible weather wise. We have had pouring rain almost every day this week. But I knew a way to put this weather to use and to have some real fun. Rain makes mud and I have a slave who hates to get messy. I figured since he’s been bad he’s going to make me an at home video. I’m going to make him crawl through the mud in a bright pink neon bikini. Kind of like a little sexy kitten since everyone knows he’s not a real man. Then once he’s all nice and dirty, I’m going to make him look straight up at the camera and tell everyone what he really is. How much of a little bitch boy he is. How he loves licking my asshole up and down. He’s going to tell the camera how much of faggot he is when I bring guys home with big cocks. He’s very quick to get to get on his knees. When the video is finished, I’m going to send it straight to his wife.

Silly sissy you’re no man!

sissy phone sex redSilly Sissy you are no man, you are just a fake little loser that has come to me for your comforting and humiliation. I deal with ‘men’ like you all the time. Even in my daily life, with your fancy cars or big trucks, always trying to take away on what a pathetic piece of shit you are. But you know you can be your loser self with me, you know I’ll treat you just like you wanted. I even picked out an outfit for you already – collar included. So everyone can know you’re my bitch! Clip that collar on and I’ll attach the leash, walking around main street like you’re my special pup. Everyone is laughing your whole pathetic ass being exposed with a big huge sign screaming fuck me I’m a sissy fag! And who could pass that up? Looks like these big cocks are about to dominate you, my pet. I’ll sit back and watch you taking cock in your ass and smile, knowing you’re loving every second of it.

You will do exactly as I say!

sissy training phone sexHahahahaha, you of all people want to be a sissy? A sissy bitch? You think you’re pretty enough, you think that you’re gay enough for for the job? I am so not sorry to tell you that you are not the sissy for the job. You see if you want to be a sissy you have to be a very pretty girl I’m talking a full on make over and if you won’t allow me to do that than you’re just not worth my time. Well technically you’re not worth my time anyway but I do enjoy spending my time humiliating a pathetic sissy loser … And a loser like you is going to need a lot of work a lot of waxing new girlfriend and of course we’re going to have to get your ass ready. Do you know how we’re going to do that? Lots and lots of ass fucking not only from me and my massive strap ons but my fucking huge big black cock friends. Every sissy whore loves big black cock and it’s no different for you, loser. Don’t try and tell me differently. You’re taking cock up your ass like it or not, bitch.

Stranger Helper for the House Party

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I love having big house parties with fellow Doms who bring their slaves. It’s always a blast for us. The slaves love to be put on display and have fun trying to impress us. Some of the Dom’s enlist their slaves to help me. They send them to help me set up a few hours early. They all are strangers for the most part. One of the slaves was dusting my entertainment center when I needed help. I had to change the light bulbs in my play room but couldn’t reach without getting on a chair. I didn’t want to risk getting hurt so I made him be the one to get on the chair. While he was on the chair, I noticed his tight ass. I knew I just wanted to punish him. I would get the perfect chance tonight. He was going to be the slave that all the doms focused on tonight. I’m going to have the doms make him beg to take my strap on right up his ass. This night will be a night he’ll never forget.

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!!

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I’m currently hurting for money since I spend it all on drugs. I can’t help but want to get high all the time but it’s really hard especially when your broke and even more so if my friends are broke to. So i went to my dealers house and asked him if we can trade my services for his amazing drug. He agrees so we snort a couple of lines and that’s when the high kicks in. I feel invincible so I got  on my knees and literally swallowed my dealers cock. Stroking and swallowing I had my dealer on a whole new level of ectsy! I continue raming his cock into my the back of my throat until the dealer starts fucking my mouth with his hips. Until finally his he explodes his load in my mouth. My dealer then snorts down another line and asked if I would trade another line for anal. Of course is what I said I mean who can say no it’s free drugs! Plus I love having my holes filled!

All of us humiliate our site mascot!

sissy phone sexI’ve been training Anastasia to be the perfect Mistress, just like me. She is learning well with lots of practice humiliating our loser sissy! Some of my favorite things to make this loser sissy do is sing to me, over and over again. She just fucking adores to be forced into humiliation. I should say that the site sissy loser doesn’t have to be forced to do anything at all because she wants to do, begs to do it just begs for the humiliation that we give her. That’s not all the dirty little secrets I have about sissy! I have some VERY dirty (literally) secrets and I know that as soon as sissy lays her eyes on this blog she’ll be making that poopy panty pudding all over again. Oops! I let the secret out…as if everyone didn’t already know that our site sissy loser liked to poop in her panties. That’s even more embarrassing than the size of your itty bitty winky. What else can I do but laugh at a pathetic failure like yourself. A failure at being a man but definitely are winning at being a stupid pathetic sissy. The kind of sissy that has no control, that begs for this over and over and doesn’t care if she gets caught or exposed because what you really want is to entertain and be the silly fairy faggot you are and as I help teach Anastasia how to be a superior mistress like myself we will continue to use you for practice in our humiliation towards you, got that you poopsie panty pudding sissy? That might as well be your new name – I might even write a song and make you sing it. Who knows – I can make you do anything! We all know that…don’t we? Go ahead and go clean up sissy, we all know you have plenty of panty pudding to take care of.

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