Tag: Crossdressing Phone Sex

Mommy’s Sissy Phone Sex

Sissy Phone SexCharlie’s such a good Sissy Phone Sex slut and doing training with mommy is paying off so much.

Daddy and I decided that maybe it was time to let Charlie have her first client since that… more than a little painful experience the last time she was on stage.

She was a little afraid, not having a real cock in her ass since that night but Daddy and I assured her that she’d be fine.

That this person would be gentle and love her tight little ass and cock.

So, I dressed up my little Charlie. Using a pretty satin pink dress with a sparkly hair bow. I put on a pair of white cotton panties with a matching pink bow on the front and a pair of shiny black mary janes. Before doing a simple and very natural makeup on her. She didn’t need much, she looked so much like her twin sister. Full pink lips, smooth cream colored skin, big blue eyes with long eyelashes, and naturally curly blonde hair.

She was such a sexy little Sissy Phone Sex whore and I could tell she was excited and nervous as her “Date” knocked on the door. I opened it to find our friend, he was a tall man and built like a tower. All muscle, beard, and intimidation.

I had a moment of uncertainty but he was paying us a lot to play with our Charlie so I invited him in. He smiled warmly at our nervous sissy and Carlie said hello with a cute blush and shuffle of her feet.

The man squatted in front of Charlie. “What’s wrong little one? You look scared.”

Charlie blushed brighter and smiled weakly at the man. “It’s… You’re big and…” she looked down shyly at floor, refusing to meet the man’s eyes.

“Well… Why don’t I give you a preview of our night tonight and we’ll see if you’re still scared of going with me?”

Charlie looked at the man surprised. “We can do that?” she looked at me after. “Would it be okay?”

I laughed, “Of course!” I agreed, liking the idea of seeing this man with my little girl.

So the man took Charlie’s hand. Her hand looked so tiny in his and led Charlie to the couch having her kneel on the cushions as he knelt in front of charlie. He lifted her skirt and rubbed his huge hands from Charlie’s little cock to the back. Cupping his ass, finger pressing up and against Charlie’s little asshole.

“Oh…” Charlie breathed, squirming against the man’s hand as he leaned forward. Licking a wet spot along the hardening little cock underneath. His hands moving to pull the panties down to his thighs. Sucking on his middle finger for a moment before returning it to massage against the little asshole. Pushing a finger in as the man takes the entirety of Charlie’s cock and little balls in his mouth. Sucking and licking and making Charlie moan and hump against the man’s face.

It only took a moment for him to cum, but he more than happy to go with the man after that. I can only imagine the amount of fucking that happened that night with my perfect little Sissy Phone Sex slut.

Let me tell you about my new sissy phone sex caller

sissy phone sexLet me tell you all about my newest sissy phone sex caller, she calls herself Candi Slut and she is the most ridiculous sissy I have ever seen! See, here’s the thing about sissy phone sex, it doesn’t always go the way you want it to and trust me, this sissy learned that the hard way! She said that she hadn’t been feminized in quite a while, poor little sissy had moved away from her previous Mistress and thought that she could just go back to being her “alpha male” self. Hahaha oh man, did I ever laugh at that shit! This little bitch has a tiny penis and a feminine attitude, there is NOTHING alpha male about her at all! She didn’t like that I laughed at her pathetic little penis, she tried to say it was big but I made her admit the truth… and the truth is that it is the smallest dick I have ever seen! I forced that sissy to fuck herself with a nice big rubber cock as punishment and even though she tried to say that it was way too big and that it was hurting her, she kept on with it and soon was leaking her precum everywhere! You see sissy? Mistress really does know best! And that is something you would do well to remember during our next sissy phone sex call!

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Have you tried crossdressing phone sex yet?

crossdressing phone sexLook at you, you’re just a wimpy, little dick sissy boy that is a perfect candidate for crossdressing phone sex! With that tiny little penis, you definitely are no kind of man so you may as well just give in and become the sissy you were always meant to be! Oh what’s that? You are a real man? You don’t want to be a sissy??? Hahahaha I don’t give a fuck what you want bitch! You have a tiny little dick, it’s more of a clit really so you will never ever be a real man! No woman, especially a woman like me, will ever fuck you or even allow you to touch her with that nasty little baby dickie. Women like me like a big fat cock… as a matter of fact… let me bring in a REAL man with a big fat cock. He can show you the differences between you and even help me dress you up in something frilly and feminine. I will give you a complete makeover and you will see how good it feels to give in and be the sissy you were always meant to be. By the end of this, you will be sucking dick and begging to get your little man pussy’s cherry popped!

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If The Skirt Fits, Wear It

adult phone chat zettaI put in applications at every store in the mall. I needed a job and I needed one soon.
I was secretly hopeing to land the opening at Victoria Secrets so that I could get a discount on some awesome new lingerie. Instead I got a call from one of the clothing boutiques.
It was a nice little store that sold both male and female attire and had a variety of styles, from semi conservative to borderline risque.
The first couple of days were uneventful and then he came in.
G.Q. handsome, with a mysterious look about him.
As protocol required, I approached him and asked if he needed any assistance.
He politely turned me down for the moment.
Staying close enough to admire him while attempting to look busy and not at all obvious, I saw him pick up a few women’s items and stash them in between the men’s clothes he was gathering.
I saw him head for the dressing room and I made my way around the store grabbing the female items that he had in his stack.
I walked over to his cubical and slid the items under the door.
“What is this?” I heard him say.
“I am sorry for intruding.” I said “But I noticed you choose these items and I believe you have picked out two sizes to large for you. These should fit perfectly.”
“Hold on a minute.” he said through the door.
I saw him pick up the pile and a minute later he had the door opened and was standing in front of me wearing nothing but the shortest black skirt. it fit like a glove and he looked magnificent!
“How does this look?” he asked.
“Perfect. How did I do?”
Pulling me into the dressing room with him he said. “I don’t know lets find out!”
I love my job….

How Bad Do You Want It?

adult phone chat dixieReally? You’re back again? Begging for a chance to be with me. Smiling I am waiting for you to say the words that will get you what you want, if you have big enough balls to back it up.

“Please Dixie. I fucking adore you, let me show you. Let me worship you. I will do anything”

Ahh those were the words that I have been waiting to hear…..

“Anything????”

Exasperation, desperation, evident in his voice he says ‘Yes Dixie, yes, ANYTHING”

Now my pussy is wet and I am about to see just how much he means it.

I take his hand and lead him to my room. I take out my pretty pink dog collar and matching leash and fasten them around his neck. He is grinning like a Cheshire cat and the bulge in his pants is growing.

He has no idea.

Smiling I walk to my closet. I haven’t said a word since taking his hand and leading him to my room. I emerge with a pretty pink dress with lots of lace and frills and a pair of pink heels. Then I walk over to my dresser and pull out a pair of t back pink panties and matching bra. When I turn around his dick is in his hand, the head covered in pre-cum.

I feel a twitch in my cunt, his dick is very impressive. I certainly hope he meant what he said and I get to find out if he knows how to use that thing in his hand.

Laughing I walk over to him and slap the shit out of his dick and lick the pre-cum off my hand as he winces.

“Are you ready?”I ask.

“YES YES YES I AM’ he can barely speak he is breathing so hard.

I take off his shirt, then his jeans, and his boxers.He grabs me and I pull away and the puzzled look on his face is priceless. I grab the pink panties off the bed and bend over telling him to step into them.

“You want me to wear your panties?”he asks in disbelief.

“Not only are you going to wear the panties, your going to wear the entire out fit and I am taking my cross dressing pet out for the day. If your good, when we get back here, you will have earned your time with me. You said you would do ANYTHING. Remember?”

The look on his face while I dressed him before putting on his make up had me laughing so hard that my stomach hurt.

 

Trannies Rule. Sissies drool. Get some tranny phone sex.

 

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Dating a tranny will always be a surprise, like opening a present. Such is tranny phone sex. Cause even if you know I’m a tranny, you have no idea that I have these great tits and 8 inches of meat underneath this skirt. You’re a dirty little faggot who wants to suck this hard tranny phone sex cock and feel me as I introduce you to some hardcore ass fucking. Call it your pussy though. That’s just so much sexier. I like that boy pussy. And I like it all tight and virgin. The way you cry out the first time I push through that sphincter really whets my desire. I am always the top and you are my submissive little cum hole. There are things I do expect though when we meet for tranny phone sex. Shaved balls are a must. And bring a toy for our call. Hearing you impale yourself on a dildo makes me jerk so freaking hard. Don’t be afraid though. I am gentle with cowards and first time callers. For your pleasure we can even do cyber chat through Yahoo. It’ll make that boring meeting at work so much more fun and you can hide that erection under the table. I promise that I’ll have you running to the restroom to jerk off before we are done though!! Take a chance and try a tranny!!

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Cumming in the Rain….

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I could feel the heat the moment I walked into the room. He was hot for sex with a tranny and he had made it clear that I would be getting his massive cock all night long. I was trembling with excitement when I saw that it was all true. I could tell from the bulge in his khakis that he wasn’t lying. It had been pouring rain all night but that didn’t dampen the tension between us. Several drinks later and we were all over each other. His hands slid under my skirt, groping my shaft and fondling my fine tits. The other bar patrons watched us with amusement and jealousy. I bet more than a few were stroking under the bar. Finally, we could take no more and we ran, giggling, out into the downpour.

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The summer rain soaked us to the skin, not cooling our ardor one bit.  I made it to the car first and climbed on the hood, spreading my legs, beckoning him. He didn’t waste a minute, pushing me back, lifting my legs and pushing that thick fuck stick into my boy-pussy. We had that old car bouncing as he howled in glee up into the rain, his jet stream of cum filling me inside. Afterward, we stood in the rain as the water washed the leftover cum down my thighs and onto the pavement. Summer storms make me so hard!!!

Hardcore ass fucking tranny

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I saw your ad in the paper yesterday. I may just be the one you are looking for. I’m a 19 year old tranny with beautiful tits and a large cock, and a hardcore ass fucking sex drive, just as you requested. I am very feminine and can be either a top or bottom. I’m clean and drug-free. I’d love to meet an older man like you who knows exactly what he’s looking for. I’d love to get me some of that virgin ass and make a believer out of you. Once you try sex with a tranny, you’ll never want a regular girl again. You see, tranny girls know exactly what you need, how it feels to have a cock and how to touch and please you. We know the dark recesses and sweet spots on a man’s body and we’ll never have to ask if you like what we are doing. We know how you love it. As my cock swells, so will yours as you touch my surprise package under my skirt. Are you ready for some shaved cock and balls? I want to be your first taste and the one you jerk off to at night. I want to be the whore that you sneak out of the house to see and the reason why you never fuck your wife anymore. I want you to crave my taste and the feel of my big dick. When I push it inside of you, you’ll be shocked. I am so tight, like a virgin but I can take any size or race. I’ll stroke you hard until you beg for mercy. You cock will explode on your belly as I spew my sperm deep in your boy-pussy. How can you deny that your dick is hardening in your pants as you read this? It’s time to admit that I’m right.

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Surprise!

sissy phone sexSurprise! It’s my sissy’s birthday and she is going to be so excited because I got the best surprise! When she walked into this mess all she saw was black…lots and lots of black cock that is! It was going to be the best party, I knew it as soon as Sissy opened her mouth wide for the first big black dick she could get her lips around! She was shocked and totally unprepared for it but like the little whore she is went straight to sucking. She is a total big black cock lover and can’t ever help from being a greedy cum guzzling slut! I made sure she had PLENTY of big fat BLACK cocks to suck on! There was plenty of dick to go around, and double the amount of cum! These guys balls were full and loaded and beyond ready to be drained. And me? I couldn’t stop laughing and laughing! My humiliation surprise party was big hit…and I knew my Sissy loved it too!

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Sissy schools phone sex: Class in Session

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We are going to hold a special session today during sissy schools phone sex. That’s right you are going back to school. I’m going to be the head master and I have taken a special interest in you lately. Everybody has to dress up like a girl everyday but I have assigned you a special outfit. It is a whore red push up bra which I require you to stuff and a matching red mesh see through G-strong with your little clitty tucked for me. You always report to my office before school at seven A.M sharp so I can teach you how to do your makeup. Blue eyeshadow and bright red lipstick with heavy eyeliner makes you look like the good whore you are. Then I lead you into a bright classroom with cameras on the wall. I record everything you do to record it as black mail. For the first lesson of the day, you sit in an uneven chair and write “I am a sissy whore bitch” over and over again. I only let you give it to me and stop writing when you have written 500 sentences. It takes you about two hours. Your hands are cramping and are in pain by the time you are done. You see me smile. You know that you being in pain brings me pleasure. For the second lesson, you get on your knees and go suck the dildo on the wall. Its 10 inches and we are working on having you deep throat it all. So far you can only take 8 inches without gagging and almost throwing up but we are getting there. Soon you will be an expert cocksucker. For the last lesson of the day, I sit on your face until you are begging me to let you breathe again. Once I soak you in my pussy juices, I let you go home. I’ll see you tomorrow for a new lesson.

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