Sissy Telephone Sex

He Likes to Talk


Sissy Mistress Ivanna

Some of my callers love to listen. They listen to the fantasies I spin, and the stories I tell. Some callers love to talk, and some are very, very good at.

I had a caller last week who wanted to talk and have me listen. He came up with a wild tale that I would like to tell you all about:

He said, “First imagine that you’re wearing a huge hard dildo strapped solidly to your hips. I’m on my hands and knees, and naked in front of you. I’m waiting in anticipation for you to violate my ass with your hard on. Now take just the tip, and tease my anus. Only put it in a tiny bit, then take it out quickly. Repeat this over and over for little while…”

I imagined I was doing just that. My hips started to move back and forth uncontrollably in my chair. This was turning me on.

He continued, “Now squirt some lube on it, and push it in deeper. Not all the way, just a little deeper so I can feel it.” He paused for moment and took a breath. “Okay I am ready for a little more,” and I imagined I was pushing my strap on in him deeper than before. I could virtually see him on all fours in front of me.

“Now, just shove that thing all the way deep inside me!” And in my mind, I did. All the way in. I could hear his breath catching in his throat. I wondered if on the other end of the line he was doing to himself what he was imagining me doing. That turned me on too.

“Fuck me! Just frigging fuck me!” He yelled. So I did just that. Moments later I heard him cry out as he came. This had been fun for me. He thanked me and said goodbye, but now I was left with a throbbing, horny pussy!

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October 16, 2017   No Comments

The Caller Who Cried


Mistress Annalise

I was taking what I thought would be a simple sissy/cross-dressing call. How mistaken was I!

This caller was practically in tears when I answered the phone. “Oh mistress, I’ve done something terrible!” He said, humiliation emanating from his voice. Sternly I said, “What have you done, my puling little transvestite?” “I’ve gone and soiled my favorite dress. I had an accident.” So much shame in his voice.

“You’ve pissed yourself? You deplorable little shit. Well you better get yourself all changed up quickly. Mistress hates the smell of urine on her sissies.”

“Okay mistress,” he replied. I could hear him fumbling around on the other end of the phone. He continued, “I’m changing into my black supper dress, with white panties and white stockings.”

“I want you in your highest heels, or I will hang this phone up on you right this second! You know your mistress will be home in 10 minutes. You need to get yourself together.”

“But I have a hard on mistress. Can you help me get rid of it quickly?” I went into action.

“Who’s my favorite sissy? Who do I love to belittle, to degrade, unless you’re all dressed up?” I could hear him breathing hard on the other end of the line. “In the meantime, you better cum for mistress!” My voice was getting louder and I put more avarice in it. “Now, you fucking cross-dressing sissy! I want you to come now!” I heard him gasp, as he began to moan, “Oh mistress! Oh mistress!” He made some guttural noises, and I heard him cum, cum hard. Another satisfied customer!

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October 16, 2017   No Comments

Degrading a Cross Dressing Caller


Miss Divine

“Hello?” I answered the phone. “Hello.” A rather timid voice replied. “What are you up to, today?” I said. He answered, “I am staring at myself in the mirror. I really like what I see.”

I moan a little bit in anticipation of what he will say next.

He tells me he is wearing a black bra and black lacy panties, with black garters and black stockings and black shoes. He is playing with his “baby clitty”, and it feels so good. “Take it out of your panties,” I command. He does. I ask him what he sees in the mirror now. “I see a very big clit, which is attached to my ass-pussy.” He is sort of whining, and I don’t like that.

I tell him to straighten himself up and fast. I want him to speak to me in a submissive, but not whining, voice. I tell him I’m giving him a barehanded smack, several as a matter of fact, and I spank him until my hand is stinging. He promises to change his tone.

I tell him to take his panties off, sit on the floor in front of the mirror, and bring his knees up until he can see his ass-pussy. I instruct him to get a toy for his ass. Good boy he has one handy, and I allow him a few seconds to properly lube up the dildo. “Now fuck that ass-pussy,” I tell him with authority. I can hear the sloppy sound coming through the telephone, and I know he is obeying my orders. Ah, what a good sissy!

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October 16, 2017   No Comments

Cross Dressing Sissy – Transvestite Phone Sex

Mistress Skye

“I got this idea from a phone sex line that I like to call,” said Miss Polly. She stood before me, a demure little creature, dressed only in her panties.

“I want you to dress as follows: Your blonde wig, that tight pink sweater with the matching skirt, and those pink high heel boots,” I told her. She was a lovely transvestite, with a zest for anal sex and role-playing. She got dressed as I had instructed.

I turned her around so her backside was facing me. I held up her skirt, and could see she had cut a hole in the derrière of her pantyhose, making access to her asshole easily available. I reached behind me for my strap on. I put it on quickly, and was ready to fuck.

I pushed her to her hands and knees. I took the bottle of lube and covered my cyber-skin cock and her ass hole with it. Then I slipped my entire head and shaft up her back door.

She gasped and ground her ass up against my hard on. I started moving in and out of her, listening to the noises she was making. She was enjoying this for sure.

I took my fake cock from out of her, walked to the front of her, and forced her mouth open. I then stuck the ass juice-covered dick in her whorish mouth. She gave me enthusiastic head, sucking and licking my strap on until it was clean.

I love fucking this dirty cross dressing slut!

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October 11, 2017   No Comments

Want to be my little sissy in slut wear?

Mommy Clara

Hello my little sissy bitches. You ready to worship this wet cunt of mine? I can tell you like when I dress you in my dirty cum dried panties. I’ve caught you sniffing them. I know you’ve noticed the pubes in them, as I have a hairy pussy. I have to get my big fat dildos out when we sissy phone sex talk. I know that is the only way I am going get any satisfaction. Your little chap stick size dick won’t do shit for this luscious hairy pussy. If you’re a good little bitch, maybe I’ll let you taste my ass while you play with your man clitty. That’s only after I parade you around in sissy wear. You know, the cute little slut outfit I bought you since you’re such a great whore. OMG, you really are going to pull that pencil thin penis out, aren’t you? HAHA! It really is as small as you said it would be. Maybe you get to watch my other fuck toy pound my pussy with his 10 inch beautiful cock. See what a BBC can do to a woman.

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February 22, 2017   No Comments

WILD KINKY PHONE SEX

Mistress Samara

I took off work early one day and caught my boyfriend doing the same. His car was parked in front of our apartment so I thought, I’ll sneak in and surprise him. I was horny as hell and had planned to masturbate anyway.

Well, I slipped in unheard and I could clearly hear that he had the same plan. He was in the bathroom moaning. Water splashing. I slipped off my clothes and barefooted down the hall to the bathtub thinking we could do it in the bathroom.

He was in the tub wearing my pantyhose, and the water sloshing all over. He was fucking the hose by holding his hand down flat on his tummy. Surprised to see me the sloshed and even more water onto the floor, but in my mind…being open to a wild kinky fuck phone sex role play I got right on in the tub.

And I rubbed my cunt all over those wet hose, you know what? I enjoyed the living shit out of it. I think I came harder rubbing my clit on those hose with his hard dick slit fucking me from under them than I have ever cum with vanilla sex! I am an adventurous phone fuck so give me call, nothing is off limits with me.

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February 1, 2017   No Comments

YOU COCK WHORE

Sissy Mistress Ivanna

Today my darling, you are going to know what it truly feels like to be a woman. Let me introduce you to my good friend. I want you to drop down to your precious little knees and open wide, just like a baby bird waiting for it’s mom to feed them the worm.

Take him into your mouth, and suck. Get him nice and slippery, trust me. Focus on making that hard cock even harder. Relax your throat and let it slide way into the back. Move your head up and down and dont be lazy with your tongue, swirl it around. Mmmmm Good girl!!

Now stand up and pull those pretty panties of yours down. Turn around and bend over. Grab your ankles sweetheart. You’ll want to hang on to something for this. I know you know what is about to happen. Your hard little clitty says it all. You are anxious to feel that big dick slide right into your little boy pussy aren’t you? Yeah, you can’t deny it. I noticed the wet spot on your panties while you were sucking him off.

Take a deep breath and feel that fat helmet head pressing against the resistance of your tight sissy twat. Relax some, just let it happen. Feel him stretch you out with every inch he pushes inside you. Now start grinding and matching his rhythm. It’s OK, I know it feels amazing! Reach down and rub your clitty, and spray your sissy seed everywhere, but NOT before he fills you up like his own personal little cum dumpster!

I’m so proud of you! Your virgin ass cherry has been taken and you are now officially a faggot cock whore! Excellent job you little bitch! Well done! I love doing cum slut phone sex calls. All sissy queers are welcome. Call me so I can be proud of you too!

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February 1, 2017   No Comments

WHEN WAS THE LAST TIME YOU HAD FUN

Mistress Nelly

Welcome back my little sissy bitches. How have you been? Are you doing all of the naughty delicious sissy phone sex assignments I’ve given you? I hope so. I have received several photos of you dressed up in your very best. Looking all kinds of girlie feels so fantastic doesn’t it? You know you love the feel of that silk and lace against your clit and mangina almost as much as you love feeling a nice big thick hard fuck tool violate your throat. Don’t deny it, we both know just how right I am.

When was the last time you made me proud and dropped down to your dainty little delicate knees and opened wide? When was the last time you proved yourself as a delicious little cum dumpster? Most importantly, when was the last time you called your Phone Sex Mistress and showed her the adoration and respect she rightfully deserves? If it’s been more than 3 days, you should be ashamed of yourself! Looks like someone might deserve a spanking huh? Go ahead and put on your pretty things, and call me so I can find something else for your mouth to do! You know you need some Sissy Mistress Phone Sex.

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February 1, 2017   No Comments

WHO WANTS A MONKEY ROCKER

Mistress Pascal

One of my favorite girlie boys got himself a new toy. A fun toy. It’s called a Monkey Rocker. Do you know what that is? Let me explain further. A Monkey rocker is a special rocking chair with a big fat dildo attached to it so you can rock back and fourth and fuck yourself as fast or as slow as you’d like. This little sphincter fairy loves the feeling so much, he’s almost replaced his office chair with this new one!

The first time he used it, we were doing our kinky sissy phone sex call. He had mentioned ordering it a few weeks earlier but I had no idea it had arrived. He was so excited to share this with me. He had dressed himself in something very girlie, then pulled his pretty little panties to the side and slid down onto the seat, letting out the most adorable sissy squeal I’ve ever heard. His pussy was stuffed full and stretching him out! He changed his speed to experience this new feeling to the fullest and didn’t take him long at all to launch that sissy seed everywhere! He made his panties nice and wet like a good girl!! How many of you out there would like to have a chair like this one? I’m sure there are quite a few of you. Call me for some spectacular sissy phone sex and we can discuss the yummy details!

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Mistress Pascal

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February 1, 2017   No Comments

YOU WILL BE MY FUCK TOY

Miss Divine

I WILL make you My fucking fuck toy! You will bow at My knees and kiss the ground I walk on. I will put a collar on you with a fucking pink leash to lead you around to all of My friends. You will be naked that way all of your holes can be violated!

I will have a mixture of men and women, all of my filthy whores just waiting for My direction and all of your holes exposed for their use. You will take turns sucking on cock and licking my girlfriends stinky asses and eating there wet pussies! I will put a cock in your mouth and a strap on cock in your new little pussy and fuck the shit out of you! I will soon replace that Strap on cock with a real, really BIG cock to gape that little pussy of yours.

So if you need some Domination phone sex then just call your Mistress and you will definitely get what your fucking ass deserves. How about some Humiliation phone sex to put you in your place, then you know who to call.

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Miss Divine

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January 31, 2017   No Comments