Sissy Sex Change Phone Sex

sissy sex change phone sex

I love feminizing naughty boys into girls, but sometimes you meet a rare gem and know they need an sissy sex change phone sex fantasy. I found a pretty sissy slut that wanted to take things further. No matter how much makeup and girly stuff I put on him, he wanted more. He didn’t want guys fucking him in his stinky man pussy. What he wanted was a real pussy to play with and nice big bouncy tits! He had an extreme transformation fantasy that involved me changing him from a pathetic hairy man into a divine female slut. I’m a woman that loves extreme makeovers so naturally I was ready to dial up some doctors for his gender affirmation surgery.

He didn’t want to keep his cock and balls, which I understood completely. He was so small why bother even having a dick. laughs He came to the right place, I love doing sissy sex change transformation phone sex fantasies with a good role-play story. I decided to be the sexy mad scientist that would change him from a dull boring guy into a glamorous sexy vixen. It all started with me strapping him to the table in my laboratory. After that, things got really weird.

I love doing sissy sex change transformation phone sex fantasies with a good role-play story.

I was dressed in a super sexy nurse outfit and he was naked. Naked and strapped to a cold hard table, waiting to trade in some sweaty wrinkled balls for a nice smooth pussy. And I was also ready to make his dreams come true and transform him into the sexiest trans woman alive. I gave him some special pills that would numb the pain but still let him feel things. Then I took out my tools and instruments. Various science fiction type stuff, really advanced technology. You have to pull out all the stops when you’re orchestrating a sissy sex change phone sex transformation.

I attached a giant suction cup over his cock and balls as well as cups on his chest, over his nipples. Next I turned on the cups attached to his chest and smiled as he felt the intense suction. I used a laser wand to rid his body of all the hair. It only took seconds and a quick pass with the wand and he was smooth and soft as any woman ever has been. I gave him a few shots on his face and soon it started to soften and change. His stubble was gone and he had a more delicate face and full pouty lips. His nipples were becoming nipples on a pair of nice big bouncy tits. With my mad scientist genius, he was able to skip the pain of top surgery during his sissy phone sex sex change. I turned off the tit machine once he was a nice D cup. Then I watched as the drugs I gave him started working, his waist was shrinking and his hips were getting wider.

He looked completely smooth between his legs, like a plastic doll.

I turned on the machine attached to his cock and balls and watched as they disappeared, almost like magic. He looked completely smooth between his legs, like a plastic doll. Finally I added a tiny device between his legs that would dive in and create his new vagina. A nice tight cunt that would have a plump juicy clit as well and so wet!

Now that he was a she from head to toe I took her off the table and dressed her up, added makeup and styled her long gorgeous hair. No one would ever think this hot slut was once a dud of a man. It was so exciting! Our first adventure was about to begin. He didn’t want to just be a girl, he wanted to be a really slutty girl who loved to suck and fuck lots of cock. I made him into a her, now it was time to make her into a super slut. His extreme sissy phone sex makeover fantasy was only beginning with a sex change. Now was the time for serious slut training. Call me if you’d like to be transformed into and woman. I’ll even do to you what I had done to her. And I know you’ll LOVE IT!

Extreme Domination Phone Sex Fantasy: Man In a Box

extreme domination phone sex torture mistress

One of my favorite callers has a rather unusual fetish. He likes to be submissive but not just any submissive. He likes to take things to the extreme. He wants to be totally helpless and unable to resist me and that’s why I give him extreme domination phone sex. He’s helpless and at my mercy completely. The more helpless he feels, the more he likes it. So when he asked me to cut off his arms and legs and put him in a box under my bed, well I had to.

How can a girl say no to an offer like that?! laughs It also helped that he was now an amputee so all he had to do was pull off his prosthetics and we were set. I really enjoy being this kind of creative and extreme domination phone sex mistress. I always like a challenge and something different, and this was it. So we started playing and haven’t stopped since. He gets very into it and I of course love every moment of being a domme. Going extreme makes it more intense, as you can imagine. smiles

The first time he submitted to me during our extreme domination phone sex session, I put him in the box and slid him under my bed so he could hear everything that went on that night. And let me tell you, my bed is always busy. After hours of hearing me playing with my men, sucking, fucking, dominating, punishing and teasing, it finally got to him.

The first time he submitted to me during our extreme domination phone sex session, I put him in the box and slid him under my bed so he could hear everything that went on that night

I could hear him moaning and wiggling around so I finally pulled him out so he could join the fun. I pulled him out of the box and set him on the bed and rubbed his body with oil and then humped his stumps. I rubbed his stump against my pussy and teased him with my body. He couldn’t touch me so it was torture. He couldn’t move himself to get closer or push his cock against me like so many men did. All he could do was lay there and watch while I used his body to make myself feel good. Any part of his body except his cock of course.

When one of my boyfriends came in unexpectedly I just tossed a throw over stumpy and let him lay there in bed next to me while I rode my boyfriend’s big cock. After that was done and my boyfriend had left, I pulled stumpy out again for more extreme phone sex domination. This time tugging him over to me by his cock. I teased him that I could just carry him around by his cock. I even tried to pick him up just holding on to his cock. He liked it at first but then his own weight pulled him down and he screamed with pain and begged me to stop. I did while I laughed. Then I sat on his face and made him clean my pussy before I went back to humping his stumps. I let him feel how wet and smooth and warm my pussy was. He wanted to feel his cock in it so bad.

I sat on his face and made him clean my pussy before I went back to humping his stumps.

He begged and pleaded and did anything I asked until I was finally ready. With no legs to get tangled up with I was able to put him between my legs and take him so deep. Balls deep actually. I rode him so hard and took him so deep I almost crushed his ball between us. After he came and I pulled his cock out of my pussy, we lay there and he rubbed his stumps against my throbbing swollen clit, making me cum over and over for the rest of the night. Then back in the box he went, sticky cum drying on his skin as he slept, waiting for me to pull him out and use him again.

If you have an extreme domination phone sex idea I’d love to hear all about it and conjure up a delicious fantasy that we can both enjoy. Call and ask for Naomi.

Sissy Slut Phone Sex Feminization

sissy slut phone sex forced feminization

Spring has sprung and I love watching everything change… the metamorphosis the seasons go through. Feminization is the same way you, know and that is exactly why I love sissy slut phone sex. You’re so pretty in your frilly dress. You look like you should be on top of a cupcake. But we both know it’s no cupcake you’ll be on top of tonight! Tonight you’re going to be my sissy slut phone sex whore. I want you dressed in your most girly dress. I love pink so if you have something in pink that would please me. And a slut should always please her Mistress. Spin around for me sissy and show me your goodies.

I want to see your panties pulled tight against your fat clitty. I like my sissies made up from head to toe in the very best during sissy slut phone sex. You should be picture perfect and dressed to impress. It’s so much fun to get you all sticky and dirty and messed up. laughs I won’t be happy until your pretty pink lipstick is smeared all around your mouth. You know how you’re going to mess up your lipstick sweetie? By sucking cock. You can suck my strap on cock, or you can suck a real cock. I’ve always got some submissive laying around waiting to do anything I ask. Just say the word the my sweet sissy phone sex slut, and I’ll order up the most delicious cock you’ve ever seen.

Just say the word the my sweet sissy phone sex slut, and I’ll order up the most delicious cock you’ve ever seen.

Why don’t you start on my strap on and we can move on to the real deal once you master the strap on. I know your clit and pussy are ready for my strap on. And some real cock I’m guessing. Oh yeah, you can’t wait to be a cum dumpster can you? I’ll take you out and show you off, sweet cheeks. You better strut your stuff and work it slut. I want you to get the whole room lined up and waiting to have a turn. A turn with you of course. As to what they will do on their turn, well, I’m pretty much going to say anything and everything.

Cock sucking and pussy pounding to be expected during sissy slut phone sex. You’re just dying to be a forced feminized whore for me, aren’t you? I know what a slut you are and how much you fantasize about wild fuck sessions. I think you’ll look best in a tight pink satin dress. You’ll be on your knees of course, sucking a line of cocks. Actually they will most likely be fucking your face. You don’t have to suck much, just open your mouth really. They’ll fuck it for sure. How many cocks can you stroke while you are getting fucked in the face during sissy slut phone sex? At least two, maybe three if you are crafty.

How many cocks can you stroke while you are getting fucked in the face during sissy slut phone sex?

When you are sticky and your hair is covered in cum I’ll have them strip you down and flip you over. That tight pussy needs to be tapped sweetie. Let’s go all the way during our sissy slut phone sex! You’ll give it all up and do whatever decadent depraved sexual perversions that I want. I’ll think up plenty to keep you busy. We’ll stay up all night as I let one guy after another fuck you. Fuck you and leave you sticky and used, just like the sissy slut you are. Call me sweetie. You know you need it.

Accomplice Phone Sex Abduction

Every now and then I wonder, if I knew then what I know now, would I still call Mistress Janelle? I didn’t know I would end up being pimped out for a sissy accomplice phone sex abduction. After all, all of this is thanks to her. She, more than anyone else, is responsible for what I’ve become. 
I’ve been here, wherever “here” is for several months now, I think. Some days, when the drugs are really strong, and she has me listening to multiple layered audio hypnosis files on headphones while strapped to one of the fuck benches, I forget that I was anything but a perfectly girly sissy slut, born to make cocks hard and then get them off. Born to be an obedient and enthusiastic fuck toy. I had only discovered sissy porn a few months prior to seeing the ad for the website. I had always been fascinated by pantyhose and stockings and sexy lingerie while growing up. When I got out on my own after high school and got myself my own place, I could finally play whenever I wanted without fear of being discovered.

accomplice phone sex abduction

Before Mistress Janelle took control of my life, I sometimes wore makeup, I had one pair of high heels to go along with a couple pairs of shiny tan pantyhose and a pair of classic black fishnet stockings. By the time he grabbed me, Mistress Janelle had transformed me into a nearly full time sissy slut. I wore make up every day. My hair had grown long. She had me get rid of most of my boy clothes. I barely wore them anymore anyway. Sometimes, I think about the last two sissy assignments she sent me on, both at the adult video store where I would meet and then be abducted by the Sissy Breaker during my accomplice phone sex abduction.

No panties, just my clear pink chastity device. I was the perfect accomplice phone sex abduction victim

The second to last time she let me wear sweats over my sissy outfit but, when I got to the booth I had to take them off and make a video of me riding a huge dildo, watching trans porn and sniffing poppers. I was in hot pink lock on four inch spike heels, sexy AF 24 inch waist pink corset, a tight, sheer, pale, purple belly shirt and super shiny Hooter’s girl pantyhose with the crotch cut out. No panties, just my clear pink chastity device. I was the perfect accomplice phone sex abduction victim.

In my lust and excitement to fulfill my task for Mistress Janelle, I must’ve forgotten to lock the door and I must’ve been making a bunch of noise, because after about ten minutes of me furiously riding my eight inch dildo that I had suction cupped to the floor, a big Hispanic man in a cowboy hat was pulling my face to his big, stiff dick and then I was sucking it and the next thing I knew he had, effortlessly, scooped me up and flipped me upside down and was now holding me by my ankles, so that my body was resting against the cushioned bench but my head was hanging over the edge. Then he started face fucking me as his accomplice phone sex captive.

He held me upside down and fucked my slutty throat for the next ten minutes, grunting and calling me “sissy faggot” and “cock slut” and “bitch boy”.

I had no idea at the time but, this was the Sissy Breaker and my phone sex mistress had set him up with a preview of his next victim, me. He held me upside down and fucked my slutty throat for the next ten minutes, grunting and calling me “sissy faggot” and “cock slut” and “bitch boy”. I loved it and my phone recorded it all. When he finally came, he pumped once down my throat, then pulled out and shot all over my face and hair, then he grabbed my sweats and left. At first, I just sat there, stunned, then I jumped back on that dildo and started sniffing those poppers and riding that plastic cock for all it and I was worth! I wanted to cum sooooo badly. So I rode it. 

I had no idea that the next time Mistress Janelle sent me out, I would never return home, instead becoming another one of the lucky sissies snatched and then trained by the Sissy Breaker. Another soon to be obedient pimped out sissy whore. If I knew then what I know now, would I still call Mistress Janelle? Fuck yeah I would. I love that I’m now a captive sissy phone sex whore and I love that mistress had me abducted.

Cuckold Confessions Phone Sex

There’s nothing that blends emotional and psychological pain together with eroticism as well as cuckolding. Real cuckold confessions phone sex is in my top five favorite kinds of kinky adult chat. Sure, sometimes people call with fantasies and role-plays and I am keen to explore a wide variety of fantasies if there is at least a splash of humiliation involved. But there is nothing quite as arousing as hearing a man call up and confess that he desires to see his wife with another man. What would it be like for you if your wife was fucking your best friend, a neighborhood boy, the whole basketball team, strangers from a bar, etc?

cuckold confessions phone sex



I am very encouraging when it comes to cuckold phone sex. If you are just mulling over an erotic idea of your wife fucking someone else while you masturbate, I am going to encourage you to talk to her. Talk to her about having a more open relationship. Or talk to her about visiting swingers clubs. Or just let me talk to her. Yep, I mean it too. If you both call me together, I will have you guys make love at my instruction and then bring up some other fantasies I find hot…. like consensual cheating. Group sex may be a little too much soon, but eventually I will get you both there. You only live once, you know. Might as well have fun while we are all here, right? Don’t stuff your desires for being cucked deep down inside. 

I can help you sort through all those complicated jealous feelings you’ll have at the same time you’re aroused by cuckold confessions phone sex.

I can help you sort through all those complicated jealous feelings you’ll have at the same time you’re aroused by cuckold confessions phone sex. If you want to let your wife fuck a man with a bigger dick than you – like say, your braggadocious friend from work and at the same time you hate the idea of him fucking your woman. You just need some reminders about who your wife is and who you are. You’re the cuck and that’s perfectly acceptable. You’re a different kid of man than your stud work pal. Your wife will always love you, she just might also love how your work buddy fucks her. 

I especially love more experienced cuckolds. I like it when you call me while your wife is out with her boyfriend. Fuck, it’s like the best reality porn show to speculate with you about what is happening to your wife or girlfriend while we are talking. If you can all from a land line in case she wants to call you while she is getting pounded, my pussy would very much appreciate it. I hope she can at least sext you a few photos of her with his superior cock. I just love how the thought of your sharing your wife both hurts your ego and stiffens your cock at the exact same time. Don’t worry, baby. I get it. You can call me and confess to me all your deepest darkest secrets. And if it involves your humiliation followed by acceptance of your place in this world, you can bet your wife’s pussy that I am going to be encouraging. 

Sissy Cosplay Phone Sex

sissy cosplay phone sex

I’m in the Wonder Woman outfit again for Mistress Angelique and ready for sissy cosplay phone sex. He fucks me so goddamn hard when I wear this costume. Last time he left me covered in his jizz and just *so* sore. Who am I kidding though? I love being his slutty captive wonder sissy. I fucking love it. I love the way the iconic high heeled boots made my shimmery smooth pantyhose legs look even sexier than usual, the way they make my ass look so juicy and extra fuckable. I love the custom corset/bustier top that cinches my slim sissy waist into sexy sissy girl curves. And I absolutely love the way he fucks me after he gets me all tied up and helpless. When he starts choking me with the “magic lasso” while his cock pummels my sissy pussy, that’s when I usually start squirting my sissy cream everywhere.

We met on Fetlife, through Mistress Angelique. She encouraged me with sissy cosplay phone sex training and I was pretty new to the kink scene, new to online dating at all really. I was an inexperienced but super eager sissy, desperate for the attention of a real life person that knew what a bitch like me needed. The fact that he loved sexy cosplay was a big turn on for me, typical comic book geek. I met him at a hotel room the first few times. I was so nervous but I could hear Mistress Angelique’s voice ringing in my head. “You want to be a good sissy cocksucking fuck bunny don’t you?” And he seemed sane, he was clean and he smelled nice. 

He made me feel so hot, so sexy. I felt like more than a sissy cosplay phone sex slut.


He really seemed to like how I looked in pantyhose, leotards and, boots. He made me feel so hot, so sexy. I felt like more than a sissy cosplay phone sex slut. I loved how turned on he was by my body and my costumes. I had no idea how much I was gonna love getting fucked. Well, okay, that’s a lie, I had *some* idea, having recently discovered ass play with ‘realistic’ toys. But oh wow, did it ever feel amazing to be his bound, helpless sissy bitch, and have my little virginal sissy booty pounded for hours at a time.

I think back to the last meeting and shiver. If tonight is…anything like last time, I am in for some serious fun. Last time he had me wear headphones at Mistress Angelique’s instruction, that played layered, looped sissy hypnosis audio files of her voice. Then he tied me, face up, to a weight bench, with my head hanging, unsupported, over the edge. My legs were then put into a most delectable, utterly helpless frog-tie. The ring gag made it pretty clear what kind of treatment I was in for. He then proceeded to throat fuck me, somehow both brutally and tenderly. I don’t know how to explain it. I guess you need to be a sissy to understand. See, I had been practicing on my own with what I thought was a pretty thick eight inch “realistic” dildo. I had made my own eyes water gagging on it while I learned to take it’s entire length but, that did not, at all, prepare me for the sheer savagery of his throat fucking.

“Yeah, take it all bitch, take it all wonder whore!”

Through all my sputtering, slobbering, coughing and choking he would hiss, “Yeah, take it all bitch, take it all wonder whore!” or “Good slut, surrender yourself to my cock wonder slut.” Every now and then he would reach over and rub my cock in through my pantyhose, sending even more electric sensations through my already overstimulated body and I’d forget to breath through my nose and start to choke again and then he’d slap my cock really hard. 

The ring gag, of course, protected him from any of my involuntary jaw clenching due to the slaps. I’m pretty sure that the thing that really broke me for good was when he finally started to come. He grabbed my cock and started to squeeze, super hard, and then also started roughly jacking me off in my hose, while he used the other hand to slap my balls, all the while grunting and pumping cum down my throat. Me just choking and writhing and crying and, finally, orgasming helplessly into his fucking vice grip of a fist. When he finally pulled his cock from my throat, he wiped it all over my face. I wanted more. Needed more. I need him to fuck my sissy pussy, to make me his cosplay fuck bunny cock slave.

Thank you Mistress Angelique. You knew just what I needed, I am so glad I called you.

Cuckold Phone Sex Humiliation

When someone calls with that certain quiver in his voice, I know exactly what he wants to talk about. It’s getting more and more common, so don’t worry that it’s just you. The inadequacy that leads to cuckold phone sex humiliation, isn’t your special secret unique burden to bear. The evidence is all around us, clearer than ever: Some men have what it takes to please women, and the rest don’t. And you’ve started to figure out which category you belong in. And you need to talk about it.

You can’t talk to your friends about cuckold phone sex. That’s just impossibly embarrassing.

And you can’t talk to your wife or girlfriend, because you already know one of two things is going to happen: Either she tells you not to be silly, not to worry, she loves making love with you … but you won’t really believe her … or she does tell you that actually, yes, you leave something to be desired. And you know what? That’s what you really want, you want her to tell you that she’s wanting, because then everything will be perfectly clear and understood. But it’s too frightening! It’s too real. I understand. You can talk to me about cuckold phone sex humiliation instead.

I’ll tell you the truth. I’ll tell you truths she’d never tell you. It’s easy for me to figure out exactly who you are, and let me tell you right now who you aren’t: a man. A real man. A man who can please a woman, who can keep a woman, who can make a woman want to please him in return. That’s not you. It never was, it never will be, and the sooner you accept that the happier everyone will be.

It’s really a public service I’m providing. You’ll be happier once you accept your limitations and stop letting unrealistic ideas pollute your relationships. And every woman you talk to will be happier once you stop thinking you can offer them something you absolutely cannot. Once you start talking to me everything will become clear. You’re meant for a life of cuckold phone sex stories and that’s it. I can tell you exactly what women need to please them, and I can tell you all about the qualities that real men have. And you’ll completely understand that I’m describing something you aren’t, never were, never could be. You’re something else. It’s not your fault. Just let me help you understand.

Locktober Male Chastity Phone Sex

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It’s still locktober and all my fellow keyholding mistresses know how much fun the month of October is when you have male chastity phone sex slaves! Does the thought of being in imprisoned in a keyholding situation simultaneously frighten and excite you? Good, I love giving men raging fear boners. A terrified man on his knees, submissive and easy to mold into the perfect play thing. That’s what makes keyholding cock control so very fun. You don’t need access to your cock, it just gets you into too much trouble anyhow. I’m going to take your masculinity straight out of your hands. That’s right, your penis belongs to me now and only I can tell you when, how, and where to touch it.

Locking up your penis with male chastity phone sex is essential for compliance.

A cock imprisoned is one of my greatest turn-ons. I can rest assured that you will remain obedient. It removes any lying straight from the situation. I don’t even have to ask if you masturbated because I know you haven’t when I’ve locked up the key in a safe. I would never lock your cock and throw away the key because that’s my carrot on a stick to dangle in front of you like cocks at the gloryholes. You’ll want to earn your freedom from male chastity phone sex, but if you do the crime you’ve got to do your time.

Why exactly would a wicked blonde woman want to strip the freedom of having a cock from you? Other than being a relentless top Femdom, to further feminize you of course! A chastity belt like the holytrainer or CB-6000 strips your masculinity and leaves your keyholding Goddess with all the control. Without a cock you are nothing more than a submissive, sissy doll for her to use, dress up, and parade about on display.

What are you willing to do to earn your freedom with male chastity phone sex keyholding? Imagine you are unable to stroke for three whole days. Would you become a little frustrated when I forced you to watch porn? Surely, after a week you would start to become very antsy. I think it’s time to expose you to your new duties as my personal sissy cum slut. After nine days you would you willing to do whatever it took to have access of your cock again? Or would you just accept that you are no longer a man and live as my submissive sissy princess forever?

#locktober

sissy in male chastity device
Mistress Janelle’s #1 Sissy in Chastity

Size Queen Phone Sex SPH Mistress

I’m a firm believer that bigger is nearly always better. A gorgeous woman like me, deserves a big fat monster cock. Is that something you possess? Check your pants right now, shrimp dick. How does it measure up to my dildo? That’s right. Look it up and down then look at that underwhelming thing in your boxers. The only thing you’ll be good for us size queen phone sex SPH.

size queen phone sex sph

By now you should know that SPH is small penis humiliation. Come on, you have a small cock so get with the picture, loser. You don’t have enough to please me and you are going to hear about your shortcomings while I please a man with a bigger cock or use one of my fantastically large dildos. Are you jealous or turned on? You know you’ll never be able to properly fill my cunt like I need. You know you’re less of a man and more of a girl. I mean, your penis even looks like a clit. So small cock humiliation and size queen phone sex is all I have in store for you.

Maybe I’ll even decide to cuckold you if you’re worth it. You should see how a real sexy stud pounds my sweet snatch. In so many ways, he’s stronger than you. A better man than you. He’s a real man with such a long, thick cock. You won’t be able to look away when he starts grabbing and groping me. I’m sorry you’re so useless, but not as sorry as you’re going to be when you see a real man take me in all the ways you only dream of being able to.

I’m a size queen phone sex Mistress who will show you your place in this world. Underneath me, licking the drippings from my hot freshly fucked pussy. Slurp all of that wetness up you little dicked loser.

Ass Fetish Phone Sex Redhead

Lucky for you, I’m a bratty domme with a stellar ass. I know you’re interested in having your face buried all up in between my big round bottom. I like that about you. You know your place. *giggles* So on your knees for some of the kinkiest and dirtiest ass fetish phone sex with a redhead vixen.
ass fetish phone sex redhead
The truth is, I’ve always been a bit of a brat. I’m hot, curvy and bossy. I know how to keep men wrapped around my finger. I giggle and playfully humiliate all of them. I adore facesitting and think it’s a great way to get an idea of your slave’s skills. More Mistresses should use their slaves like furniture. I mean what better tool is there to remind a man that his place is beneath a girl? I can’t tell you how many better grades I’ve gotten in college simply because I noticed my professor had a thing for hot young asses and then unleashed the power of ass fetish phone sex on him!
My sweet cunt and ass juices are going to look amazing all over your face. With your face drenched, you’ll beg me to stroke your cock and I’ll decide what you are going to do with that cock and when. I’m in charge here. You may call me Princess Cindy, your redheaded booty worship Princess. In fact, I love having my asshole rimmed so much, it’s added to my regular kink routine. Even if the guy I’m dating isn’t aware he’s being dominated and controlled yet, I still get what I want in the sweetest of ways. Some foolish men need more seducing before they truly believe they are ass fetish phone sex slaves. I mean if you just like big round asses in yoga pants, I’m confident I can turn you into a shit-hole licking and rimjob slut. My tight rosebud only becomes more delicious with ass fetish phone sex, so dial me up and press your face all up in my juicy booty!