Sissy Phone Sex for panty boys

Femdom sissy phone fantasies – dress up for MacKenzie

By Sissyplaytime July 28, 2025 Feminization phone sex, Humiliation phone sex, Sissy panty boy phone sex, sissy phone sex
"sissy phone sex" "cross dresser"

MacKenzie

When  you are looking for an experienced phone girl who specializes in sissy fem dom phone sex sessions;  then you have happened onto the right place because, I happen to have a lot of sissy stories to share with a sissy wannabe  like you.   Feminization  phone sex just happens to be one of my specialties because I have had the fun opportunity to have many sissy panty boy sluts to play with on the phone.   I currently have several real sissy’s who serve me.  I like to make them buy panties, lipsticks, and even go out dressed like a sissy gurl.

Especially if in addition to loving to dress up for me, you also enjoymy  humiliation of you.   After all, phone humiliation is a key figure in transforming you into my panty boy.  I know you like to be teased by a beautiful girl.  I know you might only want to be transformed, so look no further.  You will serve ME.  You will lick my pussy, and ass, and I may call you names, or give you a name.  There is pure humiliation of wearing my panties, or going to the store and buying panties, or perhaps me applying makeup to you.  You might convince me to watch you on webcam.  Some sissy’s have little clits, others have big ones.

Mackenzie for cross dressing phone sex at: 1-877-368-7505

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

By Sissyplaytime July 27, 2025 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

 

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

By Sissyplaytime July 26, 2025 brainwash, humiliation, loser, phone sex, teasing and denial, wimp loser
"sissy" "humiliation" "phone sex"

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

Cum eating is fun for dress up sissy during a phone sex call

By Sissyplaytime July 22, 2025 Feminization phone sex, Humiliation phone sex, sissy phone sex
"sissy phone sex"

Vanessa

I have noticed several of my callers whom are cuckold  husbands are also into being  sissies. I think it’s the natural progression of little dick losers, to go from small penis humiliation, to cuckolding and then onto, to sissy phone sex. maybe even some cum eating phone sex or strap on phone sex, too! Dressing sissies up in cute outfits and calling them by their female name, letting them know that they are not a real man, is one of my favorite types of calls.

Some sissies are even enjoy cum eating. I like to be the first girl that guys talk to when they try a taste of their own jizz.  I even love to role play that a group of men with big dicks are surrounding a little dick loser, fucking his face, forcing him to deep throat and worship their large cocks.  And of course, I’ll be there to make sure you are dressed up all pretty, and sucking cock like a pro even if you are just a sissy looking for my attention.

Many sissy’s are into many forms of phone humiliation, I like to talk about all of them, do not be shy, let me know what fantasy you would like to indulge in.

Ms. Vanessa for your sissy fantasy phone sex at:  1-877-368-7505

Humiliation and some masturbation techniques during sissy phone sex

By Sissyplaytime July 22, 2025 Feminization phone sex, Humiliation phone sex, panty boy phone sex, sissy feminization, Sissy panty boy phone sex
"cross dressing" "panty" "sissy phone sex"

Panty boy phone sex

Would you enjoy having a sissy phone sex call with some cock control added in? Would you enjoy being humiliated, dressed up in women’s clothing, and instructed on how to masturbate by a sexy and seductive Mistress? I routinely speak with sissy sluts who enjoy masturbating for me, and since I love it when a sissy slut strokes for me, I love to give them masturbation commands, after I have told them what to wear during our session, of course. Would you like to explore your own submissive sissy slut panty wearing guided masturbation fantasy with Ms Jennifer?

Schedule a session for sissy fantasy phone sex, or call me out of the blue, I absolutely will be thrilled to speak with you regardless of the forewarning that I receive. Let us play together, while we are both dressed in pretty feminine outfits, and you can stroke your clitty for me while I tell you exactly how to stroke it, and while I verbally humiliate you, letting you know that your little clitty is perfect to be a sissy penis, it wouldn’t be good for much else. You may feel empty inside and strange when you cross-dress, even guilty, but I can promise you your face will light up when I tell you how much I approve of your cross-dressing ways.

For masturbation techniques phone sex call Jennifer at 1-877-368-7505

Panty boy phone sex for the kinky guy wanting to have some sexy fun

By Sissyplaytime July 21, 2025 panty boy phone sex, Sissy cuckold phone sex, sissy feminization
"sissy phone sex" "cross dressing" "femdom"

Carmen

Far too many people seem to have misconceptions and misunderstandings about sissy husband feminization phone sex. Some people just are not sure what panty boy phone sex is really like. Well, to put it simply and bluntly, panty boy phone sex entails men who enjoy wearing women’s underwear. It doesn’t get any simpler than that, now does it? It makes them feel kinky, naughty, and it increases their erotic pleasure. It does not necessarily mean that you enjoy sucking cock, or you are submissive. Perhaps you want to have a mutual masturbation call, you just enjoy wearing panties throughout the duration, which hey, that is perfectly fine (and hot!) to me.

So don’t get sissy phone sex confused, I won’t necessarily be having you completely feminized or demean you. It really depends on what your needs, fetishes, and fantasies are. My sole purpose is to leave you feeling pleasured and fulfilled. Some men do want to have a cuckold fantasy with their sissy phone sex call, some want it to involve strap on phone sex, and still others want it to be a complete domination phone sex call or total feminization transformation call, but no matter what, all that matters at the end of the call is that you have orgasmed and you feel like you had a bit of a kinky time with me.

For feminization phone sex call Carmen at 1-877-368-7505

Sissy feminization phone sex with Ms. Vickie

By Sissyplaytime July 20, 2025 Feminization phone sex, sissy feminization, Sissy panty boy phone sex
"sissy phone sex" "cross dressing phone sex" "sissy feminization"

Sissy training

Sissy feminization phone sex. My sissy vicki is spring mode, ready to be dressed up and party with Auntie Kate, and I always enjoy buying her a new Easter Outfit.. read on..

Vicki writes….”Dearest Auntie, I hope this finds you doing well. I have an idea for a two lady call and would like to get your thoughts. It is near Easter again. Mommy has a new Easter dress for me, yellow and white, lace and bows, with a crinoline slip that makes it a little poufy, with white stockings. She wants me to look good and go to church with the rest of her girls. I have matching yellow shoes with a 2 and 1/2 inch heel. I’m older now,  and I can wear a higher heel. Mommy also took me to get a new bra and silicone breast forms in a 32C. I feel even more womanly with my bigger boobies. I called you to tell you about the new outfit. You said you were seeing a friend soon, but would stop by later in the afternoon to take a look at me. Mommy and my sisters were out of the house and not expected back for a long time In anticipation of seeing you alone, I decide to make myself up like Taylor Swift, my ideal of a young woman, with red lipstick, light makeup and a long wig Mommy bought for me. I put on my bra, garter belt and stockings and then my padded pantygirdle, all in virginal white. Next goes on my crinoline slip and my pretty yellow and white dress. I feel so feminine while wearing this dress! I am getting more and more excited about you seeing me in my new dress! The scene opens when you come to my house. I am surprised and a little disappointed that you are not alone, but graciously welcome you both. You introduce me as your niece, Victoria. Your friend is complimentary about my appearance. You explain you have talked to your friend quite a bit about me and she asked to see me. You then ask your friend that if she saw me on the street, would she think I was a sissy? I am shocked and humiliated! I say “Auntie, please, no!” Mention all the things you have told about me, things we have done together. I am so humiliated!! You friend says what she would like to do. (have me do some activity) Mention how big Vicki’s cock gets when she is excited. Have me take off my dress, crinoline and girdle. How I come is up to your decision. Love, Vicki

Ms. Kate for sissy feminization phone sex    1-877-368-7505

Sissy panty boy, cuckold, sph training and more with sissy trainer Audrey

By Sissyplaytime July 19, 2025 Feminization phone sex, panty boy phone sex, Sissy cuckold phone sex, sissy training phone sex
"sissy" "sph" "cross dresser"

Phonesex slut Audrey

Sissies be ready for me, as I adore sissy phone sex – whether it be cuckold fantasy phone sex, small penis humiliation phone sex, domination phone sex, sissy boys phone sex, I truly love it all.   Dressing you up in pretty little panties because you have a small penis , humiliating you as I have you on your knees sucking on my strap on is great, (not that all sissies have to suck a strap on) and gives me power and control.   But what I REALLY love is big dick – I can’t get enough of big cock, and one of my callers knows that all too well, she just like me, because sissy missy LOVES big dick, even though  missy is totally straight,   and  she seems to have aa big dick of his own, too!

She likes to call  me up regularly for sissy training phone sex.  W/we watch pornos together on line, missy jacks off on webcam, and I stroke on my clitoris and finger my pussy.  We both have a fantasy that she and her friend   are in a room with me , all three of us are naked,  and I get down on my knees and take turns sucking on their big dicks.  Then, I go to get one of them  a glass of water, and I let them know to keep their cocks hard for me.   While I’m out of the room,  missy’s cock starts to get a little limp,   so the other sissy gets on her knees and sucks her off to keep her hard. When I come back into the room, I let missy  know how much of a faggot she looks like, how gay she looks, even though I know he’s straight – I make sure she finishes sucking that dick, and swallowing her load down his throat, while missy strokes on his own big dick and cums for me.

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

Cross dressing sissy slut phone sex with Ms. Ronnie

By Sissyplaytime July 18, 2025 Cross dressing phone sex, sissy feminization, sissy phone sex

"sissy play time" "femdom" "feminization" Look at how sad my little cuckold phone sex, sissy loser gets when he knows I’m going to get fucked by my  lovers. He always gets excited when he knows I’m ready to dress him. You know what would look hot on you? I have some skimpy lace panties with matching bra that would look just delicious on you.  We of course have to tuck your little man clit between your ass before we can put them on.  I’ll even let you pick out the color.  I’m sure I have a matching shade of lipstick to go with those panties. No wait, lip-gloss would be so much better it will make your lips pop. Plus men love red shiny, wet lips. Next we need some heels very high ones, to show off your sexy legs. I have just the perfect thigh high boots to make you look like a dirty darlene slut.

You’re going to be my slut from now on. Do you feel sexy in those silk panties? Do you feel girly? I’m going to shave those legs of yours. I like my sissy slut nice and smooth. Now come with me to the bathroom. We have to get you all dolled up. We have company coming over and I want you to look your best for my new lovers.

I have a couple of new friends coming over and they are very interested in meeting you, yes I told them all about you. So I need you to be a good little sissy and wear your for me.  Can you be a good girl and do that for me?  Wait why I am even asking you. It’s not like you have a choice. *Giggles* Oh I think that’s them knocking right now. I’ll go get the door. You stay here and put on that dress I laid out for you. Time to have some fun with my fantasy cross dressing sissy phone sex slut.

Ronnie    1-877-368-7505

 

Sissy trainer Shannon will turn you into a girl

By Sissyplaytime July 17, 2025 Cross dressing phone sex, Humiliation phone sex, Sissy panty boy phone sex
"sissy" "feminization" "phone sex junction" "Big Cock"

sissy phone sex

As I am writing this, I am on the phone with Sissy Francisco who is wearing panties for me, pink panties to be precise, he knows that those are my favorite. Not only are they pink, but they are extremely silky too, he told me that he can’t stop himself from reaching down and stroking his little clitty over those pink panties. He is begging me to suck my strap on.  He is really begging me tonight, he wants be feminine for his Mistress so badly, he knows that I have a giant pink strap on, and he would do absolutely anything I desire just to get a taste of it.

So, I thought I would tell the world about Sissy Francisco and our phone sex together. I told him to take pictures for me, of him sucking on his big pink dildo that he bought specifically with me in mind. He told me every time that he sucks on that big pink dildo he imagines it’s my big pink rubber cock. I humiliated Sissy Francisco, told him he is not a real man, a real man wouldn’t be caught dead begging to become a sissy cocksucker! Sissy Francisco is simply a feminized sissy slut, more woman than man. Sissy Francisco even loves to wear a long blonde wig when she is sucking on that big pink dildo, he loves to look like a pretty little slut for me.

Sissies, stop reading and start dialing! Call Shannon now at  1-877-368-7505