sissy training phone sex

Coerced Feminization Phone Sex with Quinn

by

Now that I am in my forties, I’ve learned exactly what I like and am not shy about it. And I love coerced feminization phone sex. There’s something so fucking hot about slipping a supposed alpha male into something soft and feminine, watching the way his body reacts to the feel of silk against his skin. There’s power in dressing a man in delicate lingerie, especially when it’s my choice. I’ll start slow, teasing him with a playful smile as I show him the pieces I’ve picked out—a lacy bra, satin panties, maybe even stockings if I’m feeling especially daring. I can see the mix of curiosity and hesitation in his eyes, but that just makes it all the more thrilling.

Coerced Feminization Phone Sex

I’ll trace my fingers along his chest as I guide the silky fabric over his body, loving how vulnerable it makes him feel. There’s something so sensual in reversing the roles, seeing a man submit to something he never expected to enjoy. And as the silk hugs him in all the right places, I see him soften, surrendering to the moment, letting me take control. I love how the smooth fabric clings to his skin, making him feel sexy in a way he never has before. It’s not just about the lingerie—it’s the trust, the intimacy, the way I can blur the lines of what’s traditionally masculine and feminine. And the best part? Watching him slowly realize how much he enjoys it. The way he blushes, the way his body responds to my touch. It’s a power trip for me, but also a way to explore something intensely erotic together. The look on his face when he sees himself in the mirror, feeling both exposed and desired—it’s absolutely delicious. And at that moment, he’s entirely mine, wrapped in silk, fully under my coerced feminization phone sex spell.

1 888 662 6482 and ask for Quinn

Sissy Training Phone Sex with Quinn

by

Sissy training phone sex is one of my favorite things to do. There’s something so satisfying about transforming someone from their everyday alpha male self into the obedient, delicate sissy they were meant to be. I take pleasure in every step of the process, guiding them with a firm hand and a teasing smile. It’s not all fun and games, though—there are rules, and I’m very particular about how they are followed. From the moment they offer themselves to me, I’m in control. I know exactly how to bring out the soft, submissive side they’ve been hiding. I start slow, of course, making sure they understand what to expect –that while I can be sweet, I don’t tolerate disobedience. When I tell them to slip into something pretty and feminine, I expect nothing less than perfection. The tiniest bit of hesitation, and they’ll feel my stern side and my whip. But when they do things right? Oh, I’m not above praising, rewarding them with a gentle touch or a whisper in their ear.

Sissy Training Phone Sex

What’s especially delightful is watching the change happen over time. That initial nervousness fades, replaced by a deep desire to please. My sissy knows their place, following every command with anticipation. They learn to embrace their new role, loving how it feels to be under my guidance, to be molded into something soft and submissive. And as much as I enjoy being strict, I’m never without a bit of playfulness. I tease, test, and push boundaries to see how far they’ll go to earn my approval. Then it is time to take the next step, being the sissy girlie cock slut that they always suspected they might be.  By the end of our sissy training phone sex sessions, they aren’t just transformed on the outside—they’ve fully surrendered. And that’s precisely how I like it. Stern, but with just enough charm to keep them wanting more.

1 888 662 6482 and ask for Quinn

Cross Dressing Phone Sex with Gretchen

by

I love turning a weak little man into a beautiful sissy. Cross dressing phone sex is something near and dear to my heart. I love the idea of taking advantage of a weak and pathetic man. Making him submit to me in ways he never thought possible. Making him whimper and beg on the phone to me like a needy little bitch. Just imagine if you were there trying to fuck me, and before you knew it… the tables were turned. I’d love to take some seemingly strong man and just shove the dildo to my fucking machine so far into him he’s begging me to stop. Turning him into a pathetic drooling mess of man meat, right before my eyes.

Cross Dressing Phone Sex

Just the thought of how good it would feel to fully cripple you mentally because your cock just exploded harder than it ever did before. You and I both know you need to give up some control.
Just imagine coming home from a hard day at your manly job and giving control over to me. You see, I’ve always had this massive fantasy of entering a sissy pageant, making you compete. Telling you to show me you deserve the role you want in my life. Making you the neediest little bitch you can be in the prettiest pink ruffly dress you’ve ever seen.

Do you have what it takes to be the best of the best? Let’s find out! call me now so we can roleplay our cross dressing phone sex fantasy and turn you into my little sissy whore. I can’t wait to cum together my little sissy faggot. Just get on the phone and give me a call for cross dressing phone sex at 1 888 662 6482 – ask for Gretchen.

Email me at Taboogretchen@gmail.com
Follow me on Twitter @taboogretchen
Follow me on Bluesky @taboogretchen.bsky.social

Domination Phone Sex with Gretchen

by

I love domination phone sex. I love using my sissies and showing them their real place. Only real men get to fuck my tight bald pussy. I fuck my sissies, but only with a 12″ strap on. My latest sissy had never had a cock in his ass before, which I found hard to believe because everyone knows sissies are secretly little fags at heart. So I introduced him to my silicone sissy trainer. He tried to resist and was met with a sharp slap to his ass, I told him if he didn’t obey, I would bring in one of my BBC lovers to fuck his ass and make him regret ever crossing me.

Phone Sex

I bent him over and lubed up my strap-on and pulled his tight red panties to the side and started working my way into his boy pussy. Like the little fag he is, his asshole easily took my huge strap-on. I plunged it in and out of him and made him beg for me to plow his ass and make him my bitch. In no time his pathetic little cock was filling his panties with a big load of cum. He was moaning and groaning, saying how much he loved that big cock in his tight little pussy. He was crying saying he wanted fucked EVERYDAY from now on. I called my BBC friend and told him to set up a BBC gangbang with my newest sissy for this weekend! I can not wait to see my little sissy whore get used like the slut she is.

Call me now at 1 888 662 6482 so we can roleplay this domination phone sex together. Ask for Gretchen.

Email me: Taboogretchen@gmail.com
Follow me on Twitter: @taboogretchen
Follow me on Bluesky: @taboogretchen.bsky.social

Sissy Phone Sex with Gretchen

by

I love sissy phone sex. I can see by looking at your panties that you love it too. Look at the sissy panties you got on, they are so messy already thanks to me!  I can see you already getting wet and excited, just at the thought of being under my control. Oh, and let me tell you, this is just the beginning. Once I get my hands on you, you will be begging for more. Begging me to use and abuse you, to make you my dirty sissy slave. Once you’re under my control, you will just do what I tell you to do and when I tell you to do it. That’s what a good sissy sub would do for her Mistress. And you don’t want to be known as a bad sissy, do you? I didn’t think so. Are you ready to submit to me yet?

Sissy Phone Sex

First things first, I see you’re wearing those pretty little sissy panties. But oh, they are not so pretty anymore, are they? I made sure to have you mess them up real good, just for my pleasure. I love seeing you all humiliated, degraded, and turned into my obedient little slut. And don’t even think about trying to resist me. I know all your deepest desires and fantasies and trust me, I will make them all come true. I will make you my little cock-sucking sissy, choking on every hard and throbbing cock I throw your way. You will learn to love it, to crave it – worshiping every inch of it with your slutty mouth. I’ll be waiting to turn you into the sissy slut that pleases anyone and everyone she encounters. There will be SO much cock.

1 888 662 6482 and ask for Gretchen and ask for sissy phone sex right now, slut!

Feminization Phone Sex with Irelynn

by

Have you always lived your life as a little dick boy? I mean seriously, I bet it is no bigger than my clit! I have to say, you must feel as if you have been out of place for the majority of your life. If ever you have felt the need to feminize yourself, well, then you have come to the right place! I can definitely spruce up your girlish lifestyle. We can talk about lots of taboo things like surgical needs, fashion, and basic mannerisms. We can even discuss making this your permanent lifestyle when you talk to me. I will tell you what to do and what I want. I will command you in my domineering nature so that you know who is boss and that I mean business! This quality feminization phone sex with me is the best that you can ever hope for!

Feminization Phone Sex

We can go shopping and I’ll have you try on skirts and dresses in the ladies’ room in public. How humiliated you will be! I think that is one of the best parts though, humiliating you to the point that you pee your panties. Why would I ever let you upgrade to the level of a man? You just simply don’t deserve it. Your place is beneath me and your will never shatter my glass ceiling, you little worm. I could never condone or promote you to the rank of manhood. You are just my little slave girl.

If feminization phone sex is what you truly seek, then pick up your phone and dial 1-888-MOAN-4U2 and request to speak with Lady Irelynn because you must address me with respect and I will accept nothing less from you. If you are a scared, pathetic, girl, tell me what you want in an email to Brattyirelynn@aol.com. Here, you may send me pictures of your bitch ass and I can see how pretty you look. I can’t wait to hear from you! *wink*

Cheerleader Phone Sex with Delilah

by

I’m nobody’s cheerleader, so don’t even think it. When I talk about cheerleader phone sex, it’s not me that’s wearing the bouncy skirt and ponytail. It’s you. Yeah, you read that right. I want your sissy ass to be so deeply humiliated that I’m going to make you wear a cheerleader outfit and then go out in public where everyone can see you! What do you think about that?

Cheerleader Phone Sex

GIVE ME A “B’
GIVE ME AN “E”
GIVE ME A “T”
GIVE ME AN “A”
GIVE ME A “B.I.T.C.H”

WHAT’S THAT SPELL? You. That’s right. The beta bitch that you are.

I want you to gather your little clitty up into a sweet pair of panties, pull on a short and bouncy skirt, grab your pom-poms, and get ready to call out in your best little sissy voice exactly what a prissy bitch you really are. Then I want you to call for cheerleader phone sex and tell me how much you want to stand on the sidelines and cheer for the big, strong athletic men you really want to service with your sissy-sucking lips.

I bet you’ve fantasized about wearing a cheerleader’s uniform. I bet when you hang out with your manly buddies and watch sports, you secretly wish you were the sweet young thing going back into the locker room with the whole team, taking them all on at once. You wish you were the sexiest, sluttiest cheerleader on the team, so it’s time to put that cute little outfit on – knee socks and all – and call me for cheerleader phone sex.

So, what’s it going to be? Practice your splits, baby, and dial 1 888 662 6482. Dirty Delilah is here to be your cheerleading coach, so get ready to do your best bimbo bouncing for me if you want to make the hot sissy bod squad, slut!!!

Sissy Training Phone Sex with Queen Naomi

by

That’s right – you’ve got the Queen here now, and we both know that being a Queen is exactly what you’ve been wanting for so long. You sneak it when you can, trying on your wife’s panties and pantyhose when she’s not home. You play with her makeup too, don’t you, sunshine? Cum clean, fairy boy, and just admit out loud that you’re here because sissy training phone sex isn’t just what you want, but it’s what you need.

sissy training phone sex

You can’t trust anyone in your life with this big secret, especially the woman on the pillow next to yours who thinks you’re some macho man. Puh-leeeze with that shit! The reality is that deep down inside you’re a fluffy faggot, and it’s grown so big inside of you that your inner diva is practically oozing out of every pore. If you don’t call for sissy training phone sex soon, you’re going to explode girliness all over the place, and who wants to clean up that mess? Definitely not your wife.

Baby, that’s what Queen Naomi is here for, among other things. I’m happy to emasculate you the way you deserve to be emasculated. Let’s mold the best little sissy faggot out of the closeted lump of gay clay that is you. Queen Naomi can help you find your way into the finest of lingerie, the reddest face-fucking lips, and the most used sissy pussy in town. Sissy training phone sex can be a process, so you’d better be committed to making the change for real, because this is the last thing you should pussy out on, even if that is your usual thing to do. It’s time to take advantage of the pussy boi in you and finally give in for some sissy training phone sex with one of the best.

1 888 662 6382 is the number that will get you to Queen Naomi. You just have to grab those panties and call today!!

Sissy Phone Sex with Andrea

by

Hey there, kitten. You’re a little different, aren’t you? I can see it like it’s written all over you. I bet you’re wearing panties underneath those trousers. You are perfect for a sissy phone sex training session. I bet you weren’t at all like the other boys in your grade growing up. You wanted to spend time with the girls or your mother’s sexy friends. You could stare at their long legs, high heels, and pantyhose forever. You probably longed for them to take you under their wings and transform you into the pretty girl of your dreams. But back then you didn’t know what it was exactly that made you different. You couldn’t yet put it into words but you can now. I can help you become the sissy phone sex fuck doll of your dreams.

Sissy Phone Sex

You’ve come a long way since the days you used to rifle through hampers and play dress up in pantyhose, kitten. It’s time to take the plunge! With the right sissy phone sex guidance you could become one of the sexiest cross dressing sluts in the tri-state area. Sure, beauty is pain and suffering – but at least you’ll be gorgeous and all the men will want to fuck you. I’ll make sure you are ready for the job as my pimped out sissy bimbo. You’ll be silky smooth with a fresh wax, long gossamer false eyelashes and we’ll even recontour your face so it looks as feminine as possible. I love to see your fluttering eyelashes as you drop to your knees ready to service men with big cocks.

After a month of sissy phone sex homework and training, you’ll forget you ever tried to live life as a man. It will all feel so comfortable for you. You don’t have to do a thing except look pretty and think about sucking cock. I’ll take care of everything else. Doesn’t that sound nice? Not a worry in the whole world except what lipstick shade best matches your bimbo outfit. I’ll teach you to walk, talk, act and think like a girl. It’ll be easy considering you are already about half way there. So what do you say, princess — are you ready to take the plunge? Come, let Andrea turn you into her adult sized Barbie doll.

Forget all about boxers and beer cans. Say hello to lipstick and lattes.
I’ll be ready when you are.

Sissy Training Phone Sex with Andrea

by

You look at me and you think I’m really pretty. Most guys look at me and want to fuck me but not you, kitten. You look at me and want to trade places with me, don’t you? You want to be a hot blonde babe that all the guys ogle. I understand completely. You are in need of some sissy training phone sex so we can get a real grasp on your feminization fantasies. You’re in a safe space and you can tell me anything. I’m the non-judgmental bossy girlfriend type. You know, a little cruel but a lot nurturing. And giving sissy makeovers is one of my most favorite things!

Sissy Training Phone Sex

What girl wouldn’t want to have their very own life-sized doll to transform into a beautiful submissive sissy cocksucker? I cannot wait to give you a thorough feminine makeover. It’s so much fun for me to orchestrate your transformation into becoming a beautiful butterfly. If you’re willing to work hard enough, I can take you from a boring man and transform you into a gorgeous cross-dressing fuck doll. Oh, is being a part-time sissy slut not enough for you? I can transform you into a passable trans woman too. The truth is, ridding yourself of any shred of masculinity forever is quite a turn on. I know it can seem like a tall order when you’re just starting out trying on different panties. Don’t get discouraged! There’s a pretty fuckable slut deep down inside of you and I will help you bring that fuckdoll to the surface! Every masculine flaw you see can be fixed with the right sissy training phone sex.

So kitten, how committed are you to learning more about your feminine side? Are you willing to shave off all your body hair, learn to do your make up and walk in high heels? Just think about all the hot bimbo outfits you could wear for me! I could get you all done up and parade you in front of every construction site I can find. Imagine all those eyes on you and the catcalling! If you’re too shy for some public exposure, you can get all dressed up just for me. I’ll help you relax and ease into it. Just think of it as a sissy spa day with your girlfriend Andrea.

Phone Sex : Live Fetish Phone Sex