Sissy Telephone Sex

Posts from — December 2017

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