Sissy Telephone Sex

Want to be My Perfect Sissy Slut?

Mistress Samara

So, you want to be my perfect, sissy, slut whore?  Good. You’ll need to follow my precise sissy in training instructions to the letter, if this is really what you want to be.  Say it out loud and repeat after me, “I want to be your perfect sissy slut whore.” I didn’t hear you, say it again, but this time, louder.  That was better. Now follow me to my closet, I picked out some things for you when I was at the mall. Look at this super, short, jean skirt I knew it’d go perfect with this little belly shirt that’ll barely cover your perky tits.  And I got this sexty mint, green bralette and panty set, the color will look amazing with your skin.

Come here, I’ll help dress you. Step into these panties, oh my gosh, look how they hold your cock and balls against your body.  Here, let me slide the skirt up your long legs, think how every time you lean over, all the men will see your panties and they’re all going to want to fuck your tight, pretty ass. I can’t wait to watch you suck and fuck all of the cocks you meet tonight and by the time we come home, you’re going to be the most perfect sissy slut whore.

Call me so I can tell you how I’ll do your sissy slut hair, your lip gloss and how you’ll sissy slut suck a cock and balls.

Call

Mistress Samara

For Some Sissy Telephone Sex

1-800-485-9561

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June 12, 2018   No Comments

The sissy that you were born to be

Mistress London

Admit it; your dark deep desire is to be turned into a sissy.

 

My top specialty is sissy phone sex. I have turned many big strong men into wimpy sissies.

Truth be told, I love turning the big strong “alpha” men into sissies. The challenge of transforming them by guiding/pushing them to set aside their fake macho facades is amazing.

 

Your secret is safe with me so there is no use in denying it. At the end of your transformation, you will love every second you get to be a sissy. The first task will be you buying yourself bras and panties to wear under your clothes. Next will come thigh high stocking and after that will come pumps, make-up, blouses, skirts, dresses, etc…

 

During the time that you learning to dress and look like a sissy, anal training will start. You will buy butt plugs that you will wear for longer periods every day. You will also be wearing one when you jack off your dicklet. You may as well enjoy busting nuts as much as you can now. In time I will own your orgasms.

 

At the end of my training you, you will wonder why it took you so long to admit that you were born to be a sissy. Are you ready to be what you were meant to be?

 

My other specialties include domination phone sex, body worship phone sex, strap-on phone sex, anal training phone sex, taboo phone sex, golden showers phone sex and many more.

Call

Mistress London

For Some Sissy Telephone Sex

1-800-485-9561

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May 3, 2018   No Comments

Tasks for you sissy.

Mistress Skye

Before calling me, you will have these tasks completed. You will also understand and agree to my rules.

1) You will be wearing sissy panties. The colour of them is not important as long as they are sissy panties– the kind of panties you would be humiliated to be seen in by the guys at work. Your humiliation is hilarious to me. 

2) Your puny little pecker and balls will be shaved to the best of your ability. Sissies are not real men so your widdle manhood will not look like real men cocks and balls. You are not allowed to touch your dicklet either until or if I give you permission to do so.

3) You are prepared to call me Mistress and you will do everything in your power to please me. You will not top me from the bottom and you will know your place.

4) You have the understanding that you will not cum until or if I say you can. I want to hear how much your dicklet aches and I want to hear you beg for release.

5) You have the understanding that disobeying me will result in you being punished. The punishment could be orgasm denial phone sex, ruined orgasm phone sex or cbt phone sex.

6) You have the understanding that you will experience sissy phone sex domination phone sex and humiliation phone sex. My other specialties are cuckold phone sex

Once these are finished and understood, you may call me sissy.

Call

Mistress Skye

For Some Sissy Telephone Sex

1-800-485-9561

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March 21, 2018   No Comments

A pegging is what you need

Goddess Erica

o, you need to be fucked hard in the ass? You crave hot sissy phone sex and femdom phone sex don’t you. Come here, drop your pants and spread your ass wide slave. Oh no, it is not time to be fucked just yet. We need to clean you first. I am going to insert the tip of this enema inside your ass. You will not make a mess of my 9-inch strap-on. You will hold the water in for at least 40 seconds and then you will go expel the water out of your ass into my guest bathroom. You did not think you were allowed to use my toilet, did you? There is much training to be done with you.

Now that your ass is clean, get your clothes off and bend down over my dresser. Now spread your ass wide again. I am going to lube up your worthless ass and I want to hear you beg for me to fuck you. I am sliding it in now so do not tense up. Keep your ass spread slave. You like that don’t you. You like being fucked in your manpussy? I want to hear you moan loud that you love it when I fuck you in your manpussy. Yell louder slave. Now lie down on my bed and get your ankles up. Take it like the wimp you are slave. Now stroke your pinky dicklet. Do you like this slave? I can’t hear you. Yell louder.

Oh, there is a lot of training that needs to be done with you.

Call

Goddess Erica

For Some pegging Telephone Sex

1-800-485-9561

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March 1, 2018   No Comments

Cross-dressing Daisy Chain

Miss Divine

A client called our phone sex line not long ago, requesting that he be allowed to tell me his fantasy. Of course, I encouraged him, this was just fine!

He began by telling me that he was a sissy cross-dresser who loved cock. “I’ve always fantasized about being part of a daisy chain with at least 3 other cock sucking, cross-dressing sissies,” he told me.

Mmmm… Tell me more,” I replied.

He continued. “In my fantasy, 3 to 4 other sissy girls and I are all dressed in our best bras and panties. We all have our makeup and hair done, and everyone’s excited to be there.

Since I am the hostess, I start by laying down on my back on the soft carpet in my living room. Then the next pretty sissy girl lays down with her cock area near my face. The next girl, and the next girl, each one positioning herself so that everyone’s cock is near somebody’s face. We all slide our panties down under our balls, and each sissy girl starts sucking the cock nearest to her face. We are essentially forming a circle, each one of us with a cock in our mouth.

After a little while, we all switch partners, and continue on this way. Everybody has a turn at everybody else’s rod. Everyone is fingering the ass hole that belongs to the cock they are sucking. Our goal was to climax together, all 4 of us, so everybody kept everybody else apprised of where they were in regards to cumming.” This juicy phone sex call continued.

I am the first person to claim that blowing my load was only moments away. Another sissy girl says she is right behind me, and only seconds later the 2 remaining sissy girls chime in with their own admissions of cumming momentarily. Then all of a sudden *BAM*, we all climax together into one another’s mouths. And so,” he concluded, “that is my cross-dressing sissy daisy chain fantasy”.

I was impressed!

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December 4, 2017   No Comments

A Dirty Cross-Dresser

Mistress Skye

We PhoneMates receive many calls from sissy cross-dressers. It is one of the most popular fetishes on our website, as well as in the phone sex calls we get.

Dirty sissy “Sally” phoned in last week. Sally is a dirty bitch, a filthy cross-dresser who always has some sick game to play. I loved her!

I asked Sally how she was doing. She answered, “I’m just fine. I’m lying on my bed in a sexy pair of blue sheer panties with little bows around the top. And you know what? I’ve come 3 times in this pair of panties and they are stuck to me like glue.”

You fucking hot slut,” I replied. “So why are you calling me?” I teased.

Because I want you to talk me through my fourth and final cum of the day. That will do it, these panties can’t hold any more of my sticky loads. I want you to humiliate me and shame me into cumming.”

No problem there. “You shameful, disgusting sissy. You’ve gone and soiled your beautiful panties, you fucking pig. It’s all I can do to even talk to you, you make me so sick, so full of vile hatred for you.”

Oh yes, Mistress, tell me what a sorry slut I am.”

You know what a sorry slut you are. You’re telling me that you are just lounging about in semen filled panties, wanting to pump another load of jizz in them? You are a sorry cum dump, you whorish piggy.” I could actually hear the sound of him beating off, hard, through the phone line. Listening to his vocal noises, I could tell he was getting close to that forth load.

Stroke it, sissy!” I demanded. This phone sex call was awfully fun. “Beat that meat as hard as you can, you worthless piece of shit, you cum gargling, bukkake eating fuck hole! I imagine you are a total sissy cream pie Queen! Guys blow their big, hot loads up your ass-pussy and then you push those white, frothy loads out! Don’t you, you big sissy!”

That was all it took. I could hear him blowing his load like it was the first one of the day, growling loudly and panting hard as he filled his underwear up with that last load.

Oh Mistress, thank you-“ he began, but I cut him off.

Fuck you, you nasty sissy!” and I hung up my phone.

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December 4, 2017   No Comments

Pantyhose Tales


Mistress Samara

He started his call off with simply “I am wearing pantyhose. They are suntan. And maybe just a size too small. They crush my penis into my lower belly in a really tight way.”

Never surprised by what I hear during a phone sex call, I replied, “Do you like them that way? Does that feel good?”

Oh my God, yes. They make my package feel so warm, so nestled, so tight up against me.”

I continued on by asking him “What would you like me to do?” To which he replied, “Do you have a pair of pantyhose you could put on?”

I had another customer who liked pantyhose play, so it just so happened that I did. I explained to him I needed to put the phone down for just a moment so I could squeeze into mine. He gladly accepted the silence as I did what he asked.

I quickly opened my lingerie drawer and removed a pair of black pantyhose. I slid them on and was back on the phone in under a 30 seconds. “I’m back and I’m wearing a pair of pantyhose, just as you asked.”

Pretend you are with me, and lying on top of me,” he said. I put my mental mind to where he was. He continued, “Now rub up and down on me, your pussy through the pantyhose rubbing on my cock.” I moaned, letting him know I was with him in spirit. “It feels so good,” I whispered over the phone. “So fucking good.”

We continued our fantasy of me rubbing hard against him with my open legs, my wet pussy encased in tight pantyhose. I imagined I could feel his hard cock pushing against the mesh fabric, and rubbing up and down on my clit. He continued to whisper about how good it felt, and told me of the changes in size and hardness his cock was going through.

When he was finally completely erect, I turned up the heat. “Come on, you hose freak. Show me how hot it is when you come in your hose. I want to feel that white, hot mess seeping through your pantyhose and soaking into the crotch of mine.”

A few moments later, he came, and very, very hard. I gasped and moaned with him while he came. I told him I could feel his huge load congealing around my pussy lips.

This was a very satisfying phone sex call!

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December 4, 2017   No Comments

I Love a Good Sissy!

Mistress Annalise

I love my job as a PhoneMate. I love taking all of your phone sex calls, no matter what the fetish. Today I had a wonderful call from a sissy cross-dresser. She spent almost 10 minutes just describing herself, what she was wearing, how she had grown her hair, and how much she loved being a girl. But it was my job to turn her on and get her off so I wove the following story…

Imagine you’re lying face down on your bed in your prettiest panties. A man is in the room with you, he is terribly good-looking, handsome face, solid head of hair, strong arms and strong hands, piercing eyes, a muscular ass, and a really nice package. He comes up behind you and places himself on top of you, but not touching you. He starts by kissing your neck, and tracing the line with his tongue down your spine to the top of your panties. He takes one finger and lightly runs it underneath the waistband of your panties. He edges them down a little bit, including the front, until your own handsome “clitty” and “ass pussy” are fully exposed. This phone sex call was getting pretty hot.

He starts by rubbing your ass with his strong hand, and every time his fingers graze the crack of your “pussy”, he applies some pressure with a couple of his fingers. He takes his other hand and gently holds your ass cheeks open, revealing your secret special part. He takes some lube from the bedside table, lubes up your pussy, and a couple of his fingers. He continues to rub your ass but now when his fingers graze your pussy a couple of fingers violate the rim. You love this. You beg for more… More fingers.

You are now naked and laying in such a way that his hard cock is pressed against your thigh. He squirts a little more lube on your pussy, and firmly pushes 3 fingers inside of you. He begins moving them in and out in a rhythmic fucking motion, you can feel your pussy wrapped tightly around his fingers, yielding slowly…

Our phone sex call continued…

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November 21, 2017   No Comments

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!

If you are interested in strap on phone sex, domination phone sex, submissive phone sex, transgender phone sex, anything goes phone sex, or whatever fetish you can think of phone sex, just call 1-800-485-9561.

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October 16, 2017   No Comments