Category: Crossdressing Phone Sex

The Tables Are Turned

shemale phone sex zettaA night at the club when the Queens are putting on a show is never dull. The atmosphere is electric and my dick aches fighting the crack of my ass where it is tucked in deep getting hard while I watch the show. These gorgeous Queens, once little sissy boys, glamorous, confident, in control and giving us all a show that we will never forget. And then she graced the stage. The most beautiful woman I have ever seen, Jessica. Her long dark hair flowing down her back, her big green eyes mesmerizing. I couldn’t take my eyes off her and my dick was not wanting to stay tucked in place. My nipples were so hard that I thought they would bust right out of my tight top. When she finished and left the stage I made it a point to meet her and buy her a drink. She was as enchanting as she was beautiful and I wanted her very badly. Finally the club was closing and I invited her to my apartment for a drink. I was over the moon when she said yes!
My dick was aching to be free and to enjoy this rare treat. Things didn’t go exactly the way I thought they would.
As soon as we were comfortable Jessica confessed. She came home with me because she thought I was a woman in the conventional sense of the word and she needed, wanted, sissy strap-on phone sex humiliation. She wanted me to put on my strap-on and let her suck it while her dick got hard and then she wanted to go in the other room and call me from her cell while I humiliated her on the phone and made her cum. Then she wanted me to join her and fuck her ass raw with my strap-on.
My jaw hit the floor, she was in for a big surprise. Thinking she would be disappointed but knowing she had to know the truth. I took off my skirt and spread my legs, letting my hard cock spring up from where it was tucked in between my legs.
To my surprise, Jessica fell to her knees and eagerly began feasting on my cock, before going into the other room. I gave her everything she wanted and more.
It may not have gone as planned but it was glorious darling, just glorious!sissy strap on phone sex humiliation queen

Goddess Brooklyn Controls Little Sissy Pink DingleBalls

humiliation phone sex size queenHere at Fuckalicious Freaks, we have a house sissy we refer to as Sissy Fairy Fag. Looking at her pictures, I am sure you understand why she is called that. Technically, Mistress Levi owns her, but being the nice bitch in charge that she is, she will pimp her out from time to time. I was having a cocktail party for my fellow goddesses. This was an all female soiree; dominate females only, with the exception of Sissy Fairy Fag, who was my maid for the evening. I was VERY clear that she be in proper maid attire, so I was livid when she arrived looking like a baby.

If I wanted an adult baby serving my guests, I would have asked for one. One of my Femdom friends suggested, “If Sissy Fairy Fag wants to be a baby, well we can treat her like a big baby.” That particular Mistress, made Sissy Fairy Fag pull her diaper off for a spanking. We all took a few whacks at her bare bottom. Oh did she ever cry. Sissy is a wussy too.  What a crybaby. She whimpered like a wounded animal. To shut her up, I took her pacifier, rubbed it on her bottom, then put it in her mouth. She grimaced, but sucked it. At least sissy was being obedient.

sissy phone sex humiliationMy friends were enjoying shaming her. I mean, look at her. You know you are giggling your butt off looking at her in her pink bonnet and homemade matching jumper. I decided that since baby liked sucking on her pacifier, she should suck on some big dongs. My girlfriends and I put on our strap-ons and made sissy get on her fairy knees and suck us off. It was so fun taunting and teasing her about her teenie weenie. I mean our strap-ons were twice the man she could ever hope to be. Sissy Fairy Fag got orally gang banged by 12 bitches in charge. Watching her gag, and her eyes bug out, made us all wet. Shaming a sissy is a total turn on for me.

adult baby phone sex sissy humiliationI guess all that excitement made her poop her diaper. I sent her to the bathroom to clean up. I made her change into something more appropriate too. A fairy frilly pink dress! I hovered over her in the little girl’s room, and squeezed her little dingleballs while I kissed her forehead. “I own your little round pink balls tonight, so you need to march your pansy butt back to my party and start waiting on my guests,” I chirped at her. At this point she was still a blubbering mess, so I squeezed her dingleballs into submission. That made her sing a different tune.

She returned a new sissy;  she curtsied and started acting like a proper sissy maid. She served us drinks, rubbed our feet, fed us, even gave us pedicures. It was fun making her smell and lick our feet.  Much more fun to laugh and shame her however, for being a total pansy. Of course we all took pictures for my sissy hall of shame. I have had  many a sissy in my control before, but none quite as pathetic as Mistress Levi’s Sissy Fairy Fag. I encourage you real men out there, you know, the ones with adequate equipment to please me, to leave a comment on this blog post shaming and humiliating my borrowed sissy fag. A sissy this sad, deserves all the public humiliation possible.

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Sissy for Rent!

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I found a sissy for rent and I am so fucking excited. 

Yeah she is older, but I love her pink bunny outfit. I love watching her chubby body walk around in a bright pink outfit. Her profile picture made me giggle. Nose ring piggy! I am going to make her wear her pink bunny outfit like the whore that she is. But she will also be my big piggy. I want the nose ring in so I can put a leash on her. I plan on taking her to store for shopping, even to the grocery store.

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I want everyone to know to that she is my bitch. She will do whatever I say when I want her to. If I get tired while shopping and spending my sissy’s money I have a portable chair in her. My sissy will get on all fours and I’ll sit on her back till I’m rested. That is what a sissy is for. To be humiliated out in public. To be my personal bitch. To do everything I say. I am so excited to have my sissy for a day. After we go shopping and spend our day out we will get home and she will be my slave there.

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I am having a few of my girlfriends over for the night to mess with my little piggy slave. She will serve us drinks and our food. I think I’ll make her be our dinner table as well. I want her in heels and pantyhose the entire day and night. I am excited to have this piggy sissy all day. 

Put on Your Panties, Sissy School is in Session

sissy phone sex sissy trainerNot a day goes by that some loser with an inch worm doesn’t call me to fuck. Let me make myself perfectly clear. I don’t fuck short stacks. I am not submissive. I don’t give a fuck that you are paying $2 a minute to speak with me. We have bios for a reason. Not my problem you can’t fucking read. Never assume that because you are paying for a service that means I will do whatever YOU want.  If YOU are not a real man, packing real heat, YOU don’t matter. I will take your money and deny you the right to cum. Why? Because you don’t deserve to cum. Speaking with me is a privilege, not a right. You are not paying to get off, you are giving me a tribute for being subjected to your worthless ass. Men with dicks can call the shots. Girls with clits cannot.

In fact, if you are just a loser with a nub, then you need to visit my pink room. This is where I transform you from a delusional man who thinks he can please women with his tootsie roll reject to an obedient sissy girl who knows her place and can’t wait to serve a capricious Mistress and her army of studs. I will break you, train you, dress you, humiliate you, shame you, abuse you, then pimp you out as I see fit.

So now that we are clear about how this works, go put on your big girl panties and call me. You are just a phone call away from being the sissy slave you were always meant to be.  Sissy school is in session.

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Sissy phone sex cockwhore sissy likes kinky

Sissy phone sex cockwhore sissy slut likes it kinky. I will use some erotic hypnosis phone sex techniques in the realm of fantasy phone sex sessions to lead you into that forbidden zone. You’re always fixated on how it would be to dress as a sissy slut and suck cock. Let’s see how sissified you can get.

You are such a girly boy and these pretty panties are just perfect for that sweet clitty of yours to be tucked in. Get those balls pushed up and that clitty situated in these sweet things and then we will continue with some stockings, or maybe your a hose kinda girrrl? I bet you will look really sweet in a pink baby doll negligee, don’t you think so?

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We have you in some nice pretties now let me see what I have to accentuate those dick sucking lips of yours. These lips are so ready for cocksucking now, so juicy and pink!  What’s that? You want me to videotape your lips wrapped around a big juicy black dick? Well, you need not ask me twice! 

Well, your good and ready now so let’s go! Don’t be afraid of going out in public sissy! You’re going to be the party favor for a poker game at the state penitentiary. Yes, you heard me right, I have ten guards ready to get serviced by a good sissy, and if you’re really good…

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Well, well, you did a good job draining all those big black dicks with your slutty lips. Now, for the real fun! We have a special treat for you. Now be a good girl and follow us back into the cell block. Yeah, there are some mean mother fucks back here and they were promised a sweet thing in pink with a tight fuckhole to penetrate with their huge black gangster cocks. They were also promised some moist fat lips to fuck also, so let me inject those slut lips with some saline to make them good and fat. Great! Your going to be a real treat for these convicts!

 

Sissy Milking Phone Sex: Hot Ass Sex

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Sissy milking phone sex can be some kinky hot ass sex with your new kinky Mistress Phoenix. Your dirty desire for wearing panties and taking cock like a bitch is ready for fulfillment. My love for cock milking and teaching or forcing you to take that creamy load of thick cum excites me!

Your excited by how dirty you feel with your naughty thoughts of cock and cum, and I want to assist in any way I am able to. I am a very dirty girl that can bring those dreams to conception. You know I had a naughty man call me one time to assist in his forced bisexual needs. Well we explored this for many hours over a couple months, and he ultimately started meeting strangers at jack shacks to get filled with the oozing gooey loads of cum as he wore frilly panties and stockings. 

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I enjoy sharing how much I love taking cock and the smell of the dirty dick after it has slid in and out of my slut holes.I will bet your dick gets hard in those lacy girly  panties when I talk about big cock fucking me. When you hear how that rod stretches and fills me up. They way those balls tighten right before they release the spunk into that shaft and into my soppy wet and stretch hole.

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God I love how you bury your face between my ass cheeks as you suck out that cum. You filthy little cum eating slut you. Now get that tongue in deep, come on you saw how big that cock was that came in me. You know how fucking full my ass is of cum so suck every drop out. Now you best make a creamy mess in those panties for me.

I’ll be waiting to hear from you soon so we can get good and filthy.

Forced Feminization Phone Sex With Monika

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With this job I get to see a lot of cock. I know a good cock from a bad one. It makes me giggle when these big muscle guys come to me to get fucked and their cocks are so tiny. I love telling them how little their cocks are. I point and laugh.

I compare it to my little finger and if their cock is smaller than that I make them eat my pussy till I cum twice. I have one guy who I love making fun of his tiny cock! I make him wear my bra and panties it makes his little tiny cock drip pre cum. I love watching him struggle fitting his body in my tight panties and bra..

His cock is so small he might as well be a woman. I make him dance and sing songs while I put my big black cock on. He is more than willing to suck my big fake black cock. I grab handfuls of hair and make him choke on my dick. I tell him to make mommy’s cock nice and wet. I pull my cock out and hit him in the face with it. I tell him to bend over and be a good girl and take this big black cock.

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He takes every inch of my cock. He begs me to let him touch his tiny cock so he can cum but he knows that he is only aloud to cum while I’m fucking his ass. I fuck him till he shoots his cum all over the floor. But he isn’t done just yet. He has to lick and suck up all of his cum and swallow it. Then and only then am I satisfied with his tiny cock.

My Own Private Sissy

sissy phone sex analAs a grown ass woman, well special woman, I don’t ask much for Christmas. But this year, I wanted a sissy. My very own sissy I could dress, humiliate, shame and use.  Not sure why. I think because when I was young, being forced to live as a boy, I was not allowed to play with dolls, and sissies are sort of life size dolls, but better because they can do shit for you. My company here has a site sissy and the girls have so much fun taunting and laughing at her;  I decided I wanted one of my very own. The only thing I asked Santa for this year was a sissy. Sure enough, under my tree was a sissy just for me.

I dressed her as a pretty little sissy shemale helper. It was like she was my private Barbie doll. I dressed her from her pretty red undergarments, to her slutty little Santa dress. Even put a wig on her and did her make-up. She was to be my assistant of sorts. We began with her shaving my body. I like to remain hairless from my head to my toes and everywhere in between. She gladly shaved my legs and all my nooks and crannies.

sissy phone sex tranny dommeShe also cleaned my house, made me lunch, cleaned up the dog crap in the yard… I was in heaven.  Why did I not get a sissy sooner? I played with her on that first day to try her out. Tested her cocksucking skills, rim job ability, and of course had to see what kind of ass pounding she  could handle. She struggled with my cock, it is pretty big, but she understands she is here to do whatever I need. She understands my needs vary from being a sissy maid to a sissy sex slave.

Every day she services me in some capacity. From cooking me dinner, to wiping my ass and everything in between . Her ass still needs some working on. It’s so tight. But daily fucking  and dildo play will loosen that backdoor pussy right up. The best part was now I have a live in pretty toy to take care of my sexual needs. If I want my ass licked, or my balls drained, or I need a tight fuck hole, I have one at my immediate disposal.  My house stays clean, and my cock drained. And, I have the gift of laughter right in front of me too. A sissy is the best gift ever. 

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She Found Him In The Attic

 sissy phone sex melindaWe often get together and laugh at what a little dick her husband has. She always said she wouldn’t cheat so when she needs a good fuck we get together and I fuck her with a big fat 9 inch strap on. but when she found him there the attic, all alone, dressed in a pretty pink baby doll dress with plastic panties and a bonnet, rubbing his pitiful excuse for a cock, she couldn’t believe her eyes. Taking in the scene she saw that  he was surrounded by girls clothes, wigs, makeup and nail polish. He admitted that he loved cross dressing and that he often took her sex toys and shoved them up his ass, pretending it was a sweet pussy just like hers. She said he cried when she began to yell out him, furious that she had been faithful despite his little cock when all the time he was a sissy. I felt so bad listening to her and then something snapped and a look came over her face that sent a chill down my spine. She asked if I would help her. If I would be her accomplice and teach him a lesson. She wanted me to invite the biggest dick I knew over to my house, she would bring her husband and the fun would begin. She would make him dress in that pink dress with the plastic panties and bonnet and make him watch me get fucked while she stood next to him and humiliated him. She would show him what a real man, with a real dick does. And then he would put my strap on around my waist so that he could watch me fuck her like I have for months. She wanted him to know who had been keeping her pussy happy all this time. I have to admit I loved fucking her in front of him, stuffing her pussy full of my strap on and making her cum over and over again making her scream and claw my back. Something I knew he could never do for her. From here on out his name is no longer Bret, he will forever be known as Priscilla.

I will own your whole pathetic life!

blackmail phone sexI am not an easy woman to worship but I am well worth the effort. Believe me, you will treasure every moment spent with me, even the painful ones. I can’t wait to make you tell me everything about yourself, even those private thoughts you’ve been keeping secret for years. I will unearth every single skeleton in your closet and once I do pet, your life will be forever changed. I will own you completely then, you will have to do whatever I ask you to do. Unless of course, you want me to expose all of your dirty little secrets. You will be putty in my hands because you know you will lose it all if you are outed. Even though we both know that being outed is exactly what you want most! Are you ready to give up control and belong to a woman like me?