Category: Crossdressing Phone Sex

Sissy Boy Application

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I need a new sissy boy I realized today. I figured it out when I was editing my blog and the thought occurred to me that I could use a footrest at the very least. Someone new to wear my favorite hot pink latex gimp mask and who would love to clear in between my toes for me while I work. My new pet would need to be a great listener, be able to obey orders and multi-task many different duties at once. Anal training is to begin immediately following orientation- I have a large collection of butt plugs and other toys to spread your hairy man-ass for my delight. I also have oodles of gadgets for nipple play- even a little baby pink taser for keeping my pets that like a little shock now and then. If my platforms need cleaning, you will lick them until they are shined. If I need a place to ash my cigarettes, you will open your mouth. And if I need a place to sit, your face is my new throne. If you’d be interested in hearing more about the position call me. I’ll be conducting the interview process until the position is filled.

Paris Knows Best!

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My sugar-daddy sure did have a dumb look on his face watching me pick out lacy panties today. I guess he was a little confused as to why I kept choosing lingerie that was clearly too big for me but he knows the drill- Princess Paris knows best!

After putting together quite the collection, I start heading toward the dressing room and I got the wildest idea: Why save humiliating him for when we get back to my place?

The super-hot baby-bitch running the changing area motions for us to tell her how many items I need to try on and that’s when I drop the ball, knowing it’s going to freak her out and absolutely mortify my sugar-sissy. Without skipping a beat, “He has 15 items- and would you mind helping me decide which he should get?”
I get the feeling she’s into it even though her face is showing embarrassment, she snatches up our collection and we edge my darling slave into the changing room. “Come out and show us how they look, ok???” and I’m grinning ear-to-ear because I’m pretty sure I’ve never seen a man’s face this red in all my life, but again my financial-bitch knows the motto: Princess. Paris. Knows. Best.

He walks out wearing a G-string, that I selected on purpose, knowing his silly looking cock would be sticking out the sides and just look hilarious! I can’t hold back my laughter and I ask him, “You like it when girls laugh at you, right? Show us your asshole!” I see the unmistakable look of pleasure-pain come across him, he doesn’t really want us to see his hairy man ass but I need to size him up for dildo-pegging later. He nods and does as he’s told because “Paris knows best” is the law of the land.

Finally more of the girls who work there have shown up to the dressing room to watch my little freak show. I decide he has had enough for now and we make our way to the check out. He suggests for a moment that I must be done for the day, I cut him off and he doesn’t try to argue. My darling pet nods his head while handing me his American Express and recites the golden rule for me one last time: Princess Paris knows best.

I exert cock control at all times on my prison block

Cock control

There is a new guard in town and I have total cock control on my prison block. Any inmate I choose is going to have to prove his cock is worth my while. Whoever doesn’t prove it is going to have all the shitty job details around the prison, because I’m also the job assignment guard.
Just to prove my seriousness to all the inmates I found the roughest, blinged-out prisoner here. He had jewelry showing he has lots of hustles and takes in a lot of money. Well here is my chance to show everyone they are all my bitches in this prison, and I’m doing it by making the shot caller my pussy licking, fuck me til I cum prison bitch. I am going to fuck every single one of these inmates until they straighten up and do as their told. Some might need more discipline than others, CBT, forced bisexuality…so many ways to control all these male prisoners cocks.

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!

Big Black Cock Cuckold

Tranny phone sex MayAsian wives cuckold- I was over at a friends house for dinner and she is a cute little Asian. Her husband is never home and always working, well I guess she was horny because after dinner she started to kiss me, my cock got hard and she got on her knees and started sucking my dick. I guess your husband didn’t tell her he was coming home early but its ok, he is a little bitch pushover. I made him watch as she sucked me off til I came all over that pretty little face of hers. I let him know that he would b=never be able to fuck and fulfill her the way I was right at that moment. I even made that little sissy bitch bend over and I fucked him in his tight little ass hole while his wife sucked on my shaved balls and licked my ass hole. I blew a big fat load in his ass and then left. I told her to call me again if she wanted a real cock to suck on.

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!

Adult Baby Phone Sex – Shannon

Adult baby phone sexOk, so I’ve had some sissies hitting me recently, and I’ve been enjoying myself with them. Most of them love to be humiliated and forced to play around with the big, beautiful dicks that I plan to fuck. They also love when I finger or strap-on fuck their ass holes. Well, just the other day, I had a man come to me asking for some TLC. I didn’t think anything of it until he took his lovely dress off and handed it to me, displaying a very dainty-looking adult diaper cover. I hid my surprise, as this was my first time seeing such a thing, but surprised I was. When he crawled over to me and wailed a quiet “mommy” while holding his arms up to me, I figured it was time to sit down. I sat on the sofa and let him crawl up into my lap. He proceeded to cry, so I checked his diaper to find a very healthy dump. I groaned inwardly while outwardly telling him that mommy thought baby had boo boo-ed very nicely, and mommy would need to change baby. I asked if baby knew where the changing stuff was, and he gestured to the over-sized man-purse he’d brought in with him. I left him lying on the couch with a gentle warning about how he would hurt himself if he fell, and rummaged through his man-purse. I found a pack of wipes and a fresh diaper in the bag, which I brought over and used to change him. He seemed to really enjoy having his tush wiped, so I spent an extra minute or 2 doing that, making sure to clean his tee-tee and the creases and folds of it. He then spent a good deal of time suckling at my breast before he said he had somewhere to be and that he really wanted to do it again soon.Hot ass sex

Surprise

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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 Phone Sex Tricks and Treats

Mommy Phone SexHalloween is my favorite holiday.

It’s one of the few times I can dress up all my little ones to advertise them to their best advantage. It’s a great time to make new clients, get lots of free candy, and carve pumpkins.

Today, we are getting ready for Halloween and trying on costumes then we’re going to carve pumpkins. They came out one by one, showing off their little bodies and twirling to show off the costume.

Kayla went first.

I remember when I was pregnant, each of the 3 times I was a pumpkin. So of course, Kayla with her big round pregnant belly and growing tits had to be a pumpkin. She did a good job of being a sexy pumpkin. With lace thigh highs, an orange and green thong and the rest of her costume painted on. Pumpkin over her belly and tits with green leaves and vines twisting over her arms, legs, ass, and back.

Her little sister Lexi decided it’d be great to be a naughty little nun, so being my daughter, she added vampire fangs, red contacts, an inverted cross, and the outfit had to be skin tight and latex to show off her little waist, ass, and tits.

Then there was Charlotte who wanted to be a naughty nurse. So she also had a skin tight latex outfit, thigh highs, white heels, and a little head band and stethoscope. Her skirt just barely on the side of decency which means this mean girl has been teasing her brother and her Daddy like mad. “Dropping” everything just so she could bend over and show her Daddy and brother her itty bitty thong. The first time she tried on the costume I was glad it was made from latex and only needed a wipe down and the cum she ended up covered in didn’t stain.

Now, my baby, my sweet little sissy girl Charlie was wanted to be a secretary and she was such a pretty little secretary. Her hair up in a messy bun, a pair of faux cat eye glasses, a smart blazer and tight little a-line skirt that didn’t hide anything when she got her little hard on after watching her sisters. She even had on a blouse, garter and stockings, and high heels. It was adorable watching her shimmy up to Daddy and look at her clipboard. “Daddy, it’s time for your meeting.” she said in a clipped authoritative voice and as Daddy laugh, she got on her knees and ran her little hands over his soft cock in his pants. That got his interest and next thing I knew Daddy’s cock was out of his pants and down Charlies throat as Kayla giggled and had pushed up his skirt, was fingering his ass, while Lexi fingered herself and Charlotte had scooted underneath and was sucking her sissy brother’s cock.

Ah… I love my family and how close they are, I’m almost jealous they would sit and have their own little mini orgy as I carved pumpkins for the door step. I needed to focus on the pumpkins though as I noticed I was starting to draw a dick on my pumpkin… Man, maybe I should just go join them. After all my mommy pussy is getting wet and achy.

Fantasy 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.