Category: Sissy Training Phone Sex

Sissy phone sex with our site mascot is so fun!

sissy phone sexSissy phone sex with our site mascot is so funny! See, sissy is a fake man lawyer, a real big shot where she comes from and to me it is hysterical that she really thinks no one knows her secret there! I mean seriously, she walks around her town in her little sissy dresses and wears funny signs and takes pictures… she even poops her panties and walks around like that! Who wouldn’t notice that shit going on around them??? Come on, everyone sees her, everyone knows her and honestly, even if they had never seen her dressed like a sissy they would still know she was a total faggot!

small cock humiliation phone sexShe swishes when she walks, every mannerism is very feminine, she even gets her nails done and wears her little hoopy earrings! But we are supposed to believe that she is a man? Hahahaha she is no man, she is a tinkerbell transvestite, a poopy panty wearing wannabe princess, a fruity fag, all that but definitely NOT a man! That little teeny clitty she has between her legs is no cock either, its definitely just a clit, something to rub on not something for her to stroke.

humiliation phone sexNo our little site mascot is definitely not any kind of real man, she is just the little sissy fairy faggot that we love to tease and laugh at! In fact, she is even paying for this humiliation right here too! I bet half of her town sees these blogs about her and whispers behind her back about what a little sissy she is, there’s no fuckin way that they can’t see thru her act! Lets face it sissykins, all those judges you go before are laughing at you. They all know your secrets, they know you are nothing but a poopy panty wearing little sissy fairy faggot! Think about that next time you go to court…

Sissy in training

Sissy phone sex MayI have interviews all next week for a new assistant and I am not sure that any of the potential applicants are going to measure up to my old assistant. I am going to have to interview them one at a time. I need to make sure they are articulate and that they can sock a mean cock. I simply can not think some times and my assistant needs to know how to clear my mind and my pipes. I need a good pair of dick sucking lips to climb under the conference table, spread my legs apart and start sucking my juicy tip. I need to be able to release all of my pent up energy and frustration from work into the back of a willing throat that will swallow every last drop. I want a good little assistant that will follow my every direction without hesitation and do exactly what I say. It is going to be very hard to find a replacement for my last assistant indeed.

Deep Throat Princess’ Strap On

Sissy Training Phone Sex

As you know, a sissy’s training is never done. One of the first things a sissy needs to learn is how to deep throat my princess strap-on. A princess can never get enough of a sweet sissy mouth on her cock. I want you to strip completely naked. Don’t worry, I have seen plenty of tiny clitties before. Yours is no different. Get on those soft knees of yours and suck it down slowly. Gagging up a little spit is par for the course, just use it as lube honey! I know that makes your clittie throb and your sissy clitty pucker and ooze. Pretty soon you will be begging me to fill you up, but I won’t! You have to sit up and beg like a little poodle. Aww..come on, whimper for me!

Snuff Phone Sex with The Sitter!

Snuff Phone Sex

He wanted to play a game with me and I was tired of dealing with this little fucking brat. So I decided to take things into my own hands. I figured if this little shit wanted to play a game we were gonna have my kind of fun! I tied him down on the Kitchen island. He thought it was fun at first. He giggled as I took the very sharp kitchen scissors and started cutting his clothes off. He smiled as I started cutting his panties off. When I pulled them off I could not help but laugh at his tiny at his tiny cock. I went into the kitchen and turned the gas burner on. I placed each of their knives they had on the gas stove to let them get red hot. I went back to my patient who at this point was screaming to let him go. I grabbed his tiny hard cock and started rubbing it. His body started to relax and he tried to fight the pleasure that was being forced onto him. I made him cum and separated his balls with clamps as he seized in pleasure. I started to rub his cock again. Harder this time. Forcing him to get hard for me. He was begging me not to touch his cock. Begging and pleading. I smiled and put a clamp on the tip of his cock when he was rock solid. I went back to my knifes and started slicing through his tiny balls. He started to scream when he saw the smoke coming up from his legs. When he smelled his burning flesh, he started to feel it. The knife wasn’t as hot anymore and I was basically sawing through his ball sac. Every time he would pass out from the pain I would stop, put my knife back on the stove and begin to stroke his cock until he was rock hard. He was going to be awake during every last part of this. I didn’t want him to miss me playing with him.

What a little bitch

sissy phone sexOMG what a little bitch you are! Look at you pathetically sobbing because I won’t let you ruin my dress, you have your own slutty clothes go wear those! Since you want to act like a little bitch sissy, I think I will treat you like one today, go get dressed we’re going out. I’m going to take you over to my friend’s house where there are lots of horny men waiting to pay me to abuse you. I’m going to make sure that they all take a turn on you! Your little man pussy is going to be stretch wide open and dripping with cum… you will have a belly full of it too. They are all going to take a turn on you, they’re all going to make you the whore you’ve always been meant to be!

He wishes I’d give him this pussy

Sissy Phone SexOne of my pathetic sissy boys called tonight. He wanted to do an over the phone sex fantasy. I was totally down of course. I can get off to making fun of him on the phone just as well as in person. I lay down in my bed and get relaxed. I make sure and clarify that he is not fucking me on the phone either. He sighs but I know he loves everything I do to him. Otherwise, he wouldn’t keep coming back! He loves to be called a dirty little bitch. He is a nasty slut kitten who loves to take big cock in his mouth and ass. I give him a story. We are at his house. He wanted to have a house party. ( I know how cute and desperate) He leaves it up to me to put it all together. I invited over two of my girlfriends. I will call them slut and whore. Really the names fit them perfect! They are some sluts for sure. ==giggles== I command my phone bitch to strip down naked. He tries to ask where everyone is at but I cut him off. I tell him not to speak if he is going to argue or that will be two lashings added for the next time he is in my presence.  He obeys. It is silent on his end. He likes the whippings of course. He definitely doesn’t want to acquire more than his weekly total. I tell him we brought some toys. The slut pulls out a big black novelty dildo. The kind you are supposed to give as a gag gift. This dirty fucking skank loves those big cocks up his ass. the slut lubes the huge cock up nicely. we don’t want to hurt our little bitch boy toy too much. Just enough to make him cry and cum.  she slips it into his loose slut hole. He instantly begins to moan. Take that cock you little slut kitten. He moans louder. The whore then takes her pussy and spreads her legs right in front of his face. I command him to eat that pussy like it’s Chinese food. ( His favorite I might add.) He buries his face deep into her cunt. She squirts almost instantly. There you go, my little slave, eat that nasty cunt. She cums again and again. He makes her pussy get everything soaking wet. All the while he has that big elephant cock inside his ass. He asks me if he can cum. He is so eager to please. He listens to all my rules and follows them. I reward him with permission to cum. I hear him moan and sigh on the phone. I’m glad he called me. I needed someone to boss around. These pathetic cock suckers brighten my day.

Surprise

cocksucking phone sex

I surprised this business man in the men’s bathroom once while I was pleasuring myself and squirting my load into the urinal. He was wearing this really sexy suit and tie, carrying a briefcase that he dropped once he saw my sexy body. He made me giggle and push my mini skirt back down over my dick but then he surprised me by pushing the door shut behind him and locking it! He wanted to taste my dick and I wanted to make him beg for it! I made him kneel until he was eye level with my cum glistening mushroom tip. And he told me how badly he wanted to feel my cock shoving down his throat over and over again! That was enough for me to choke off his words with the brutal force of my cock shoving down his throat! He moaned and trembled when he tasted me on his tongue, and I continued to ravage his throat hole. This continued until he creamed all inside of his expensive pants as I filled his throat to the brim and made him dribble cum all down his chin.

Sissy Training Phone Sex – Luncheon

Sissy Training Phone SexOne of my favorite pansy boys contacted me today for a date. My lovely, evil mind concocted the perfect date, so I told him to put on his favorite intimates, a sexy red dress, and to make sure his bra was properly filled out, and his hair and makeup was done. He met me at the restaurant I requested, meeting each and every one of my requirements with style.

We walked in together, and heads turned immediately. It was a classy establishment, and our dresses were just this side of tasteful. We ate our meal, discussing what his goals were for the rest of the day. Little did he know what was coming.

After the waiter brought the check and he paid for it, I stood from my seat and waited for him to stand from his. Then, right there in the middle of the restaurant, I grabbed his arm and whipped him around to face me. I pushed him to his knees, being the tall fellow that he was, and I pressed his face into my breast. He quickly sprung it free and took it into his mouth like a good little bitch. I whispered for him to free his cock from under that lovely dress and start stroking it for everyone to see. He followed my orders very nicely. What he didn’t expect was for the waiter who had just served us to walk up behind him, get down on his knees, and ram his big dick into my bitch boy’s ass. He squealed into my tit before succumbing to the fucking. It was, indeed, a delicious luncheon date.

You’re in for it now sissy!

sissy phone sexOh boy, you really did it this time sissy! You’re in for a harsh fucking punishment now that’s for sure, there is just no way that I am going to allow you to get away with ruining not only my favorite nightgown but also my favorite fucking vibrator as well! You know very well that I will not use anything that you have used, especially when you cover my nightgown with cum and my vibrator has been in your ass! Fucking disgusting is what it is and now I need to teach you a harsh lesson. Now I am going to have to force you to do the one thing you always say you will never do… you are going to be sucking all kinds of dicks! Yeah, yeah, I know you think you aren’t gay but you are the biggest sissy bitch faggot I have ever met! Hope you’re ready because I see a whole lot of cocks in your future!

You will bow down for Mistress Adriana

sissy phone sexOh sissy, no matter what you think you’re going to do, you WILL bow down for me! Just look at you, you’re effeminate and wimpy and weak… you look like a little bitch and quite frankly sissy there is nothing even remotely manly about you at all! You know I’m right no matter how much it hurts you to hear it so quit all of your whining and get dressed. I need to get you looking perfect before my guests arrive, this is a big night for you and I worked very hard to set it up so you had better be grateful. I expect you to immediately get down on your knees for any man that asks you, I want to see you eagerly swallowing every inch of their cocks too! You are gonna swallow every load, no spitting any out either because good whores always swallow every drop. When I finally decide that you’ve had enough you are going to get down on your knees and humbly thank me for allowing you to be of service to me. You are going to learn your place sissy… whether you want to or not.