Sissy Phone Sex for panty boys – Page 4 – Feminization – training

Sissy cross dressing training phone sex | Debbie | Ms. Jennifer 1-877-368-7505

By Sissyplaytime January 7, 2024 Cross dressing phone sex, lingerie, sissy phone sex

Panty boy phone sex 1-877-368-7505

Whether it is sissy cross dressing phone sex training or feminization, I am the phone sex Mistress for you! I have been having a great time helping Debbie find the feminine side. She is fabulous, and I love the updates she sends me, she is also getting help learning about being a girl from her boyfriend’s, sister. She was hesitant at first at having his sister help him decide about clothing and makeup, so with my coaxing and her eventually going over to Debbie’s house, Debbie is now quite a creation. She has sent me photos, and WOW, she looks incredible.

She called me today and told me her vagina panties arrived and will be wearing them tonight. These panties have a vaginal in the crotch. Debbie said there is a hole in the vagina making her able to even sit and pee in her vagina panties. I guessed that they were flesh colored, and I had suggested breast forms, which she did purchase. So with her breast forms and pussy vagina panties she is now a real girl. She told me that it gives the illusion if you wear jeans to look like a pussy. Does this mean you have a camel toe? Debbie is going to wear her new panties tonight. She has a date with her boyfriend and he is going to bring over his van. She will wear a cocktail dress, Debbie said it is for easy access, meaning he can have access to her ass. We talked about when she gives him a blow job, if she wants to get her ass fucked, then she needs to be sure, he does not cum in her mouth. Then when he finishes, she told me he will suck her cock. She is so lucky to have a great boyfriend. She will try her vaginal pussy tonight for the first time.

We also had a pretty interesting discussion about lingerie and pantyhose. She told me she gets hot sleeping in her bra and stockings, I suggested a baby doll nightie. Also she gets a lot of runs in her pantyhose, and her bf’s sister told her to save the panty hose, cut off the side with run, and then wear two pairs. I never heard about this tip. It’s a good one!

I will keep you posted on Debbie’s date and her new vaginal pussy!
Ms. Jennifer for your sissy feminization phone sex training 1-877-368-7505

Sissy husband feminization phone sex for cross dressers

By Sissyplaytime January 7, 2024 sissy feminization, sissy husband feminization, Sissy panty boy phone sex

Sissy phone sex

Call me up when you are in the mood for sissy husband feminization phone sex. I would love to help you dress up in some scandalous, seductive, pretty, or slutty outfits. I certainly have enough clothes of my own to compare with you, I would love to hear about all of the naughty lingerie, and the pretty dresses you own yourself. Let me help you decide what to wear, dress up for me. Let’s shave your body all nice and smooth, so when you slide on those silky nylons and panties, they glide extremely easily over your skin. We can pamper your skin with lotions and treatments, and get you looking your best from head to toe.

I especially love sissy phone sex when I speak with sissies who love to dress up in slutty outfits. The more revealing the better is my motto. Let’s do your nails, your makeup, your hair, get you really decked out and looking like a completely transformed, feminized sissy. Hopefully we can get you to look passable. One way or another, we can. With the aid of some breast forms and wigs, we can have you strutting your stuff confidently. And of course, we can bring my strap on into the picture, or we can call up another phone sex Mistress as well, and the two of us can take turns using our strap ons on you, now that you look so damn hot, we won’t be able to resist!

For panty boy phone sex call Pattie at 1-877-368-7505

Princess Elizabeth owns Loser Jeffie! call Princess Elizabeth for loser phone sex!

By Sissyplaytime January 6, 2024 brainwash, humiliation, loser, phone sex, teasing and denial, wimp loser

Princess Elizabeth

Loser Jeffie is so funny, he thinks that he can please a girl now, when in fact he needs me… look at what he wrote.Loser you are nothing without me! Princess Elizabeth

“Your ownership of me, and your teasing and DENIAL of me,
and your using of me has been So DELICIOUS!!!
Staying horny and frustrated for you, and being HUMILIATED by you
has been such an exquisite and intense Thrill!
I love you, and I am very grateful for being owned and used by you!
I love the way you turn me on, and then deny me over and over and over!
I love the way you BRAINWASH me!
I love the way you take advantage of me,
your helpless and HORNY wimp loser!
The way you tell me “NO”
and giggle,
and the way I can only say “YES” to you has twisted me up inside
and made me weaker and weaker for you.
I still vote for you many times a day even though I have not been calling
I am still so EAGER to please you.”

Call this Princess to be humiliated – Call Toll Free 1-877-368-7505

$20.00 for a 10 minute minimum call

Brainwashing and humiliation Phone sex – loser jeffie – face sitting and ruination

By Sissyplaytime January 5, 2024 face sitting, Humiliation phone sex, orgasms, queening

Princess Elizabeth

I have been using Jeffie. He is a loser, he has a normal sized cock, he is such a loser that I have convinced him that his dick is small. I have also brainwashed him, I love doing that. It makes me happy, and makes my superior Princess Pussy wet! Loser Jeffie is a loser, and knows it. I even told him I would have sex and take his wallet from him, he could watch. While I was cumming I would take dollars out and put them between me and my lover, look at Jeffie and laugh as I rub all over the money. This goes on till the wallet is empty. Then I proceed to have his paycheck direct deposited into mine. Don’t worry, I will give him a dollar or so as spending money, the rest is for this greedy Princess. Also, you may notice that I use a capital J when writing here about MY loser. That is only for good form. He gets a small letter j, so all you loser’s out there, don’t think that I don’t know YOUR place, you fucking loser’s. I do!

Your place is on your knees licking my perfect Princess butt hole! Giving me your money, and ME using you. How is that for humiliation? Not enough for you? I love humiliation phone sex.

Also Jeffie is in my LOSER club… wanna see it? Click on the word loser!

Loser Jeffie also sent me in a fantasy, wanna see it? Of course you do? Why? Because I said so. Oh before I forget. I did get a LONGGGGGG call last night from a guy, wanting NOT to cum, and for me to use him, it was WAY fun! I used him good, and emptied out his wallet. Now back to jeffie, small j… is that better?

Here is the fantasy..An Idea for a fantasy.
Princess, I have to tell you about a fantasy I have. It is a fantasy about queening, or as they say, face-sitting. In my fantasy, you first lock me up in a little pink chastity belt. Then you sit me in a chair or on the floor near the bed and you make me watch you get fucked by your real man boyfriend. While you are getting fucked, you get off even more by humiliating me and saying mean devastating things to me!

Then after he has fucked you really good and you have had an intense orgasm, you make me lay on the bed, where you sit on my face and smother me. Of course you continue to humiliate and manipulate me while I service you (I know I am unworthy and that this would never happen [maybe you even keep your panties on, since I am such a loser] ) Perhaps the fantasy would be more complete for you if you also went through my wallet as I struggle for air and to please you while you smother me and use me.

Again all you loser’s out there, notice, he uses the same fantasy as this perfect Princess used recently, only I was being pleasured by my boyfriend. Ok, maybe I will smother him, as I take EVERYTHING he has!

Sissy phone sex with Ms. Audrey

By Sissyplaytime January 4, 2024 Feminization phone sex, pink panties, sissy husband feminization

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Sissy Trainer Audrey

John is my latest naughty sissy slut for sissy phone sex. He is an sissy panty boy addict of my huge strap on phone sex chat, he called me and continually begged me to let him get on his knees, dressed up for me all pretty, and suck my big rubber dick. He knew just how to please me, so that I would cave in to his strap on desires. Even this early into getting to know John, he is already becoming extremely obedient to his Mistress. He will be getting on webcam for our next sissy phone sex session, and he promised me that he would be dressing up in very sexy lingerie for me, while I send him pictures of my big strap on.

John loves femme domme phonesex with a strap on and sissy twist. He told me when he is with his wife, he loves to be on top, so he can try to get his little clitty inside of her as deep as possible, but of course, neither of them remain completely satisfied, he can’t feel the walls of her pussy, and she can’t really feel his little dick. But with me, he is my bottom, he knows that he is my submissive sissy slut. I commanded him to beg for my cock, to show me how much he wanted my big rubber dick with his mouth and his cocksucking skills, and since he was such a good sissy slut, he did end up getting my big rubber dick jammed right up his man pussy.

For sissy phone sex call Audrey at 1-877-368-7505

Cross dressing sissy slut phone sex

By Sissyplaytime January 3, 2024 Cross dressing phone sex, Feminization phone sex, Humiliation phone sex, small penis humiliation phone sex

Cross dressing phone sex

Listen up lovers of sissy panty boy phone sex, and cross-dressers in general. Sissy training is back in session for the semester, which means that Samantha has got a lot of sissy training to be doing soon. I have to make sure that all of the sissies are dressed up in the latest panty fashions, that the cock sucking sissies are on their knees practicing their cock sucking skills on my strap on, and the nasty cuckold sissies are getting whored out. I definitely have a lot of work ahead of me to do, but I am eagerly looking forward to every second of it.

It is not easy providing quality intelligent panties phone sex. Sure, any girl could claim that they love panties phone sex, and hell, maybe they do, but they just simply can not do it as well as I can. It is not easy being as great and experienced and intelligent as I am. I have make sure, using only my vocal cords and sheer will, that all of my sissy sluts are obedient and can keep up with my tasks for them. Right now, if you are a sissy slut, you are required to give me a call, let’s get your feminization training started. I need to make sure you are behaving yourself, and if you are not, I have lots of naughty punishments to put you through.

For small penis humiliation phone sex call Samantha at 1-877-368-7505

Blue balls for you!

By Sissyplaytime January 2, 2024 blue balls, humiliation, loser

Princess Elizabeth

Hey wimps and losers, and loser-wimps, ha ha ha! I have a great new idea for how You can amuse me!

And this one won’t even cost you any money!

Well that’s not exactly true.

It’s actually going to COST you Everything!

Here’s what I want you to do.

Get a blue marker.

Sharpie or permanent, I don’t care whatever.

though it would be funny and best if it was blue,

and then write on your balls

“Princess Elizabeth Owns my blue-balls”

Can you do that for me loser?

Then call me up and tell me.

No I don’t wanna see any pics of those ugly big blue balls.

It will be something for us to talk about when you are paying me to humiliate you.

It will clarify our relationship, and make you a person if interest in my world, so I can prey upon your weaknesses.

And take advantage of your submissive nature.

Do it Now! And then Call Me for humiliation phone sex at 1-877-368-7505

Sissy panty boy phone sex – let’s grind together and play

By Sissyplaytime January 1, 2024 sissy feminization, Sissy panty boy phone sex

Mia

Wanna play dress up with me and have some panty boy phone sex? I feel like dressing with you in pretty pink panties and garters with sexy white silky thigh highs. Let’s slide those sexy, soft, silky blush pink panties up over your balls and hard cock. I love the way the panties show off the out line of your beautiful cock. I can’t help but run my hand over the front of your panties.

Doesn’t it feel good to slowly slide the thigh high up your leg? You know it does. I love watching you dress up for me. You are such a good little panty boy and you really do deserve the best panty boy phone sex ever. Why don’t you lie back on the bed and let me climb on top of you. I love the way it feels when we grind together in our panties and thigh highs. Your hard cock in your panties rubbing against my wet little pussy in my panties. Our legs entwined in our thigh highs. It feels so good, faster and faster. Lets cum together in our pretty pink panties. I can’t wait anymore and I can feel your cum squirting through your panties as I cream through mine.

Lets have some fun intelligent panty boy phone sex! Call:Mia 1-877-368-7505

Sissy panty boy phone sex, let’s talk about my drawer full of panties

By Sissyplaytime December 19, 2023 Cross dressing phone sex, Feminization phone sex, panty boy phone sex

Adriana

I know what you’re thinking, “Adriana, you might turn me into a sissy panty boy” and you would be right, because I love panties. I am happy to have the chance to tell you that I wanted to talk about something that I really like. Do you want to know what else I like to do? I like to have you go and put on some sexy panties while we do a panty boy phone sex call. I love being able to wear panties, sexy and satiny are the best. Being a pantie tease is about the sexiest thing ever for me because I have about 50 pairs of sexy panties that I always have a problem choosing which pair to wear because they all make me feel so “tingly” inside. I love thong panties and little cheeky butt panties, they make me feel so feminine and a think that is something you might want to experience too.

So yea, I have a lot of fun when I wear my thong and it makes my butt look so frigging round and hot and I’m with a guy getting sexy and dirty while I pop it in his face, it drives them wild. I notice a lot of you like panty boy phone sex too, huh? Some of you guys might even be considered cross dressers, and like to wear them yourselves I hear? WOW, that is just too hot. But hey whatever blows your horn, pervies.

Come and try to get into Adriana’s panty boy phone sex sessions at 1-877-368-7505

Nasty mistress for wimpy sissy wanting humiliation

By Sissyplaytime December 17, 2023 Cross dressing phone sex, Feminization phone sex, Humiliation phone sex, sissy phone sex

Adriana

I don’t care who you are, all I want from you is feminization phone sex in a nasty, hard way. Do you want some of this nasty Mistress’ feminization training? Well, then you need to prove just how good of a sissy you can be for me. I am going to pull you by your long wig and wrap your wimpy hands firmly around my strap on. Do you feel how realistic my rubber cock is, how hard and firm and thick and long it is? I am going to make sure to teach you a lesson, a cock sucking lesson, as you have been a naughty cross dresser sissy lately. I don’t need you to speak a single word to me, all I want to hear is the slurping sounds of your hungry mouth as it is wrapped firmly around my strap on. That is right, tonight you are going to become my dirty cock sucking cunt.

I can give you sissy phone sex that will blow your mind, and believe me when I say you will definitely want to take anything I give you, I will have you craving my every command, you will simply seek to please me. However you want to be feminized is fine with me, my sissy sessions know no limits or restrictions. This realistic rubber strap on is all yours to use your cock sucking skills on. I promise that while you are sucking away on my rubber dick, your own cock will be growing hard inside of your sexy girly panties. I want to watch you stroke your own clitty for me as you suck on my cock for me, but keep your eyes wide open and look at me as you pleasure yourself for me. It will feel so intense when you shoot your load, like nothing you had ever experienced before.

For sissy phone sex call Adriana at 1-877-368-7505