sissy training phone sex

Sissy Phone Sex with Nikki

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A few words to describe one of my favorite sissy phone sex sluts are, fag, whore, cum guzzler, bitch boy, and cock taking anal whore. There are no words to describe the kinds of cocks that he has taken in the past. But what I can say is when it comes to a submissive he holds the record for getting his boy pussy gaped open. He used to be in denial when it came to admitting that he was a total dick sucking ass spreading slut. He would often say, “Nikki, I’m a stud.” I would laugh and reply, “Studs don’t dress in pink skirts and tight-fitting tops. They don’t get big tit implants. They don’t go out in the public with dried up cum all over their faces. They also don’t get on their knees and take big fat dicks in their fucking male pussy. But MOST importanlty a stud does not have a small pathetic penis either.” Jenny once told me that he took a train of cocks in his hole. Sharing what kind would be too forbidden for me to mention. This slut has gotten on his knees under a table at a club to suck off horny older men in their 70’s. Everytime I sing “suck it like a fag suck it like a fag” He starts moaning getting super horny like he’s ready to cum.

Sissy Phone Sex

Jenny’s wife is the one who turned him into a sissy and complete anal whore. She arranges cock sucking get togethers where her husband gets on his knees dressed in a costume and gets ready to serve. Jenny also has a fuck machine in his bedroom that is much bigger than the twelve inch that’s gaped his slutty ass. Just the other day, he was recovering from a string of events with people that he went to school with. Jenny had a reputation as the stud on campus. Some girls even wanted to hook up with him. But years later, his “little” secret came out. They found out that he has a small penis and defines the true defination of sissy phone sex. Payback was a bitch. One of the most unforgettable secrets that was shared with me is that Jenny got on his knees and for the first time took something different than a cock, dildo, sports bottle, or fuck machine up his slutty male pussy. Can you begin to imagine what it was? This, I can confess, was the female’s foot that he went to school with. Can any panty boy, strap on slut, or anal whore begin to imagine what it would feel like to take a girls foot up your ass? Jenny can LOL! He also had to take frozen cum cubes up his hole. So much that when he was driving on his way back home it was still leaking from his male pussy. He didn’t take it personal even though it was humiliating in knowing that he just got called a queer, whore, slut, bitch, sissy, and fag by all those girls.

If I could have been with him when he was out with his wife’s best friend at Walmart, I would have loved to witness what happened after he drank down water. His slutty man pussy was supposed to be recovering from all the dicks that he had taken. His wife humiliated and called him a pussy when he had to recover. Yet when he was at the store it was exposed that he had a fucking anal plug lodged in his slutty hole. How could this secret come to light? When he started coughing the anal plug shot out of his slutty ass. So not even the tightest pair of panties could hold that toy up his hole. That must have been one of the most humiliating things that’s ever happened to him. Can you imagine standing at the checkout line dressed in a short skirt and tight fitting top exposing your sissy phone sex body and then all the sudden cough, or even sneeze and have a dildo shoot out of your kinky hole? Can you imagine all the customers in there pointing, laughing, taking pictures, and maybe even posting it on social media with hashtags for everyone to see? I bet Jenny can. Maybe one of the worst things that could have happened was the fallout when Jenny got home and had to take more heat from his wife when she found out from her best friend that Jenny who claimed to be in pain had a dildo shoved up his slutty ass.

If I was around Jenny I would show him how much of a sissy phone sex princess I am. I would wear my favorite short white skirt and pink top, and be a total flirty tease. If he thinks what his wife makes him do is embarrassing, I would bring a whole new level of humiliation to him.

I bet his clitty is dripping pre cum in his panties right now reading this. He’s shared so many other secrets with me that I can’t share here because it’s just too taboo. I bet he’s masturbating thinking about the next time he’ll have to get on his knees for a strap on, real cock, fuck machine, large sports bottle or a real cock and suck it like a fag suck it like a fag!

Ask for Nikki by dialing 1-888-662-6482
Email: NaughtySlutNikki@gmail.com
X (Formerly Twitter) @CockTeaseCutie

Sissy Phone Sex with Annaliese

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In my opinion when it comes to sissy phone sex, a submissive male should embrace his curiosity. I spoke with someone who questioned his identity. He was unsure if his desires made him feminine or not. He confessed that when he was in high school it was a derogatory thing if someone said “Oh look at that little sissy over there!” I told him “People can be so judgmental. They cast stones and are quick to put someone down. I don’t think it’s wrong to be a sissy at all. In fact I have a lot of friends who are like that.” He found comfort in my words and just being there to listen to him. So much that he started telling me things that he had done. I’ve never seen myself to be the type of mistress that assumes things. I would rather take the time to get to know how a person feels and be there when others won’t.

Sissy Phone Sex

He told me he grew up being a bit of a momma’s boy. I told him “There is nothing wrong with loving and being close to your mom. Sometimes that’s all a guy has is his mom who nurtures and cares for him when others are casting stones. But I could still tell that he desperatly wanted to know if I thought he was into being a female and sissy phone sex. He said “Sometimes I pass by department store windows and get drawn into what it would be like to wear sexy skirts and attractive tops. I’ve also wondered what it would be like to wear a pair of panties and lingerie.” I told him “It sounds like you’re ready to dip your toes into being feminized. Just think about how good it would feel to have satin material laying against your smooth skin. Talk about becoming hooked!” That really excited him. He went on to say “How do you feel about transsexuals?” I said “Oh my, are you kidding me? You can’t get any better than a tranny. Especially if you’re bisexual. You have the best of both worlds! What more could you ask for than having a sexy female with breasts and a hard cock to go with her!”

I could feel my satin panties start to moisten. My juices became more intense when I thought about us both sharing a tranny together. I’ve had the pleasure of getting on my knees to suck a hot transsexuals cock before and the experience is something I’ll never forget. I’ve also had the pleasure of feeling a trans femm worship and lick my bare pussy as well. He told me “Annaliese, if I tell you a secret, you won’t think badly of me, will you?” I said “I certainly will not! Please share your secret with me!” I was on the edge of my seat anticipating what was about to come out of his mouth next. With sissy phone sex it could be any exciting jaw dropping event that make you finding yourself wanting to know more!

He said “I went to an adult book store and went into one of those rooms where you put money in the slot and watch an explicit flick.” I had a feeling but didn’t want to burst the bubble that he was going to tell me that there was a glory hole with a hard cock that was ready to be sucked. I knew he didn’t want to suck a mans cock but he said “Annaliese I fantasized that on the other side was a hot shemale.” He sucked that cock until it was ready to explode. He finished by wrapping his hand around the shaft and jerked it until it came all over the fucking place. I smiled with excitement and said “Yes! You are defintlly a sissy!” Hearing those words made him cum so fucking hard. He said “Yes! I’m a sissy fag! Please tell me I’m a sissy fag Mistress Annaliese.” I repeated it over and over again.
There are so many other exciting secrets he shared. Can you even begin to imagine what they were? Ask for Annaliese by dialing 1-888-662-6482 I can’t wait to hear all about the sissy phone sex secrets you want to share with me.

Coerced Feminization Phone Sex with Quinn

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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

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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

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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

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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

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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

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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

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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

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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!!

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