Tag: Crossdressing Phone Sex

Listen Up, Panty Boy:

crossdressing phone sexI keep catching you not wearing the correct uniform. You know we both agreed that you look so pretty in a bra and panties. I just love how funny your cock looks sticking out the side of that hot pink lace g-string. I’m not impressed by your decision to not hold up your end of the deal and so it’s time for a little spanking session. Let’s go ahead and put your pretties back on, sissy! Aw, now bend over my bed and let me see your ass! You’re such a good slave when I’m around to tell you what to do- why do you push your limits with the princess?

I reach under my bed to pull out two huge dildos. I make you stick one in your mouth first. Show me how you suck big black cock, sissy boy. Then I take my favorite whip out and begin lashing your ass over and over, counting out each of the strikes for you. After I think you’ve had enough of that, I hand cuff your wrists together, blind fold you and tell you not to dare spit that cock out. It’s time for some real fun now. I put on my baby pink leather strap on with a 12 inch balled cock attached. I spit on your hole and fuck you without warning. I keep pegging you and slapping those cheeks still you’re beet red down there. Are you going to be good for the princess from now on? You nod your head violently and I press myself into you one last time, allowing you to climax.

After your done washing my bed sheets, slave- we’ll start discussing your actual punishment. Call me once you’re ready.

Crossdressing phone sex with your sexy tranny.

crossdressing phone sexLet’s have a crossdressing phone sex fashion show. You confided in me a long time ago that you wanted to be a cum slurping faggot. So, it’s time for a lesson. First of all, you’ll want to bring your prettiest panties and a nice butt plug or starter vibrator. We need to loosen that tight pucker-pussy up a bit and get those juices flowing.

It’s not hard being a girl. Especially one who has an 8 inch cock. You won’t believe how many men out there are just dying for a taste of yours. Having a pussy and a cock is like being a super hero. Women are jealous and men are begging.

Ok, so do you have that lube in hand? You’re gonna need plenty of that. Let me help. Just take 2 fingers worth and rub it all over that pussy. Poke a finger inside. Feels good, doesn’t it? Oh yes, the best is yet to cum.

It’s time for sexy!!!  Let’s shave our legs and balls. Feel how silky smooth you are? You’re one step closer to being a tranny. Now it’s lingerie time. Matching panties and bras are a must. I bet you can’t wait to get some tits. I love mine so much and men love sliding those cocks between them. Let’s pick out our outfits. Short skirts, silky tops, and high heels are always classy and hot. Plus, such easy access to the goodies.

Damn, you are looking so hot that I may fuck you myself. Get on your knees and get ready to suck this tranny cock. I love a hot little faggot mouth on my meat. Get that dick good and wet because that anal cherry belongs to me. Did you really think I was teaching you so you could give that hot box to another man? I planned to keep you all for myself. Better keep your mouth shut about it. You wouldn’t want your friends and family to know your dirty little tranny secret, would you?

Stocking fetish phone sex with Nikita.

stocking fetish phone sex

Can you resist my long tranny legs in a pair of silk stockings? I cross and uncross them as I feel you watching me. I part my legs slightly to give you a quick peek of lace panties. I know what you are thinking. You are imagining my legs thrown over your shoulders, my high heels pointing at the ceiling.

You feel the satin rub against your thighs as you uncover my hard tranny cock. It’s all you can do not to push your own rigid fuckstick right through my pantyhose to find my pucker-pussy that you crave so much. You rub the head of your cock on the vee of my crotch. We are both oozing that pre-cum now.

“Fuck me.” I whisper as you lose control. You grab the crotch of my pantyhose violently ripping them open to find the prize inside. I squeal as you feverishly ram into my pussy. Your cock rubs against the torn pantyhose and you feel the friction against your balls. You grunt as your orgasm takes you over the edge, squirting helplessly all over my cock and my torn lingerie.

 

 

 

 

Adult Baby Phone Sex

Adult baby phone sexI fucking love it when you act like a big, pathetic adult baby! Fuck, that shit drives me wild! I’m your sexy ass, kinky Mommy and I love to take care of you my little pet! I have a closet full of baby clothes that I love to play dress-up with! It’s so cute and fun to see you fitting into all the different outfits! Lay back on the bed and let me put a diaper on you so that you can soil it and really feel what it’s like to have baby underpants on! I love when you giggle and smile at me while I change your diaper and play with your big baby cock! You have quite a large bulge in your diaper for being such a big baby! I can’t help myself, I want to taste it! Let me lick and suck all over it for you, Mommy likes tasting how delicious her baby’s big cock is after it’s been sitting in your soiled diaper! When you start crying, I have a pacifer to shove into your mouth so I can shut you up. Mommy likes when her baby is happy and sucking on a pacifer! Whatever Mommy says, you better listen, or else i’m going to give you a bare bottom spanking!

Deep Throat Princess’ Strap On

Sissy Training Phone Sex

As you know, a sissy’s training is never done. One of the first things a sissy needs to learn is how to deep throat my princess strap-on. A princess can never get enough of a sweet sissy mouth on her cock. I want you to strip completely naked. Don’t worry, I have seen plenty of tiny clitties before. Yours is no different. Get on those soft knees of yours and suck it down slowly. Gagging up a little spit is par for the course, just use it as lube honey! I know that makes your clittie throb and your sissy clitty pucker and ooze. Pretty soon you will be begging me to fill you up, but I won’t! You have to sit up and beg like a little poodle. Aww..come on, whimper for me!

Surprise

cocksucking phone sex

I surprised this business man in the men’s bathroom once while I was pleasuring myself and squirting my load into the urinal. He was wearing this really sexy suit and tie, carrying a briefcase that he dropped once he saw my sexy body. He made me giggle and push my mini skirt back down over my dick but then he surprised me by pushing the door shut behind him and locking it! He wanted to taste my dick and I wanted to make him beg for it! I made him kneel until he was eye level with my cum glistening mushroom tip. And he told me how badly he wanted to feel my cock shoving down his throat over and over again! That was enough for me to choke off his words with the brutal force of my cock shoving down his throat! He moaned and trembled when he tasted me on his tongue, and I continued to ravage his throat hole. This continued until he creamed all inside of his expensive pants as I filled his throat to the brim and made him dribble cum all down his chin.

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!

sissy phone sex

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!

sissy phone sex

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….