Sissy Telephone Sex

Posts from — October 2017

Sissy-Boy

Mistress Skye

A call came through for me the other day. I love it when I get a special request. This was a guy I had talked to previously, he was a sissy cross-dresser and often turned to me for discipline and jerk off instructions (JOI).

After exchanging a couple of pleasantries, we got right into the thick of things. “What are you wearing?” I demanded. “I’ll know if you’re lying so don’t lie. Are you wearing the sheer black panties with the lace around the openings, the one that Mistress likes so much?” He whimpered yes. “Rub your clitty through your undies, use your hand to rub it up and down firmly.” I could only assume he was doing as he was told. That’s one of the factors in phone sex play. You have to trust the person at the other end of the line.

I went into a scenario where I was behind him licking his ass hole. He was on all fours. I was behind him, rimming him so well. I told him to imagine I had one finger circling his anus, with the tip of my finger darting briefly in and out of him. I could hear him moaning on the other end of the phone.

“Okay,” I told him, “I want you lying on your back with your knees as far back as you can pull them. Are you in front of your mirror?” I asked. Good boy, he replied yes, he was. I told him to keep rubbing his clitty, hard, and play with his own ass for me. I could tell he was finger-fucking his ass by the changes in the sounds he was making. He was nearly growling, a noise that came from deep within him, as he neared his inevitable climax. This was phone sex at its best!

“Come on, baby, show me what you got,” I encouraged him. “I want you to put creamy hot load right there inside your panties.”

He did as he was told, and I could hear him, over the phone line, as he came and came. When he was through, I asked him if he had made a mess of his panties, and he replied yes. I told him he was a very good sissy and I was looking forward to speaking with him again.

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October 30, 2017   No Comments

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