Category: Sissy Training Phone Sex

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.

Do I look like a housewife to you??

humiliation phone sexYesterday was Housewife Day and I wanted to celebrate it but lets face it, I’m no housewife. I don’t cook or clean or cater to anyone, why should I? I am too beautiful to dirty my hands like that and besides that is what I have little sissy bitches for! I had an entire party set up filled with other beautiful women like me and they all had a wimpy little bitch boy with them. Those “men” thought they hit the jackpot! They were all convinced that we were attracted to them and just on a regular date but that couldn’t be further from the truth. Those little wimpy “men” all had a secret that they thought we didn’t know… they all liked to secretly cross dress. Women like us can sniff those little fairies out easily and when it came time to out them all none of them even attempted to deny it. We forced them all to strip out of their fake man clothes and put on their slutty little dresses for a very special photo shoot… I wonder if their families will like the pictures…

sissy phone sex

Sissy Phone Sex with Sexy GFE Shannon

Sissy phone sexLately, I’ve been getting more and more calls from these sissified men who just want to feel pretty and wanted. I will admit, it gives me a bit of a thrill. Most of the guys I’ve had up til recently had been macho men who just wanted arm candy to walk around and make them look good, someone who would look amazing on their cocks. These sissy men have been treating me like a goddess, and it has been amazing. They will come to me and submit gratefully to my ministrations. They let me bathe them from head to toe, dress them in beautiful intimates and stunning dresses. I get to do their makeup, style their hair, and help them on with their stockings and shoes. Then, I get the privilege of walking out with them, seeing mens’ reactions to the beauty we have created. I get the enjoyment of watching cocks get hard over an illusion that my darling lover had an urge to portray. My favorite part, though, has been getting to take my lovers back home with me, and having friends or even strangers come in and have their way with my lovers while I get to get myself off using whatever appendages and methods I want.

Sissy Training Phone Sex with Shannon

Sissy training phone sexMy sissy boy lover came back to call. My problem was that he came dressed down, looking a little frumpy for my tastes in some jeans and a t-shirt. So, I pulled him inside and put him on the floor. On his hands and knees, I undressed him before spanking his tight little ass for showing up so shoddily attired. When I finally had him down to his bare skin and had sufficiently punished him for his lack of good judgment, I pulled out an outfit I had made him leave here in the past. I handed him the box, and ordered him to get dressed right there in front of me.

He pulled the panties on first, tucking his cock gingerly into the thickest part before adjusting the g-string into his ass crack. Then, he put his bra on, filling it out with the little silicone pads I had found for him. At this point, I told him to stop and follow me. When we got to the bathroom, I pulled a razor and my shaving gel out of the cabinet. I forced him to shave, and watched as he did it. I popped his ass every time he missed a spot, and he missed a few.

Once he finished shaving, I brought him back into the living room, and held his dress up for him. He pulled the sexy, slinky little pale blue slip of a dress up his legs and over his hips. The dress hugged every curve of his sweet body, and his hard cock was a bulge pressed against it. When he had finally finished dressing, I brought out the wig I had bought just for him. It was close to his natural medium brown, but with some natural red shot through it. It was a sleek style that would complement his facial structure. I sat him at my vanity, and watched patiently as he put on makeup, receiving approval for each item before using it. He was such a sexy sissy. When he finished, I rewarded him with my pussy on his face.

Babysitting or Training session?

 

Sissy Training Phone Sex

I hate watching boys. Puberty has them going wild and honestly if it walks and talks I really don’t want anything to do with them. I like them so young they can’t say no! I was watching Chris. The annoying bitch boy who hated it and threw a fucking fit every time his mommy and daddy left. They knew he was a monster just like I did. This little shit was acting like a pussy ass bitch. Crying and screaming on the floor. I grabbed him by his ear and pulled him up off the ground, Almost ripping it off. Slapped his little bitch face which shut him up. I told him if he was going to act like a little crying bitch he was going to be treated like one. I had my costume wig with me for Halloween and I put it on him. We went into his precious mommies room and put her make up on him. He kept screaming and crying as I was trying to do his make up. Its ruined, tear running down his face. I slapped him again and dressed him in his mommies clothes. Made him duct tape his tiny cock back by his asshole. Put on a thong and a bra as well as a sexy see through nighty. Strapped some heels on him and shoved him outside. I made this crying bitch walk up to each one of his neighbors and tell them what he was. ” I am Christina, your new neighbor. I am a sissy faggot whore. Can I suck your cock?” He was a brand new sissy bitch and he was going to be trained so well!