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Sissy phone sex with Ms. Audrey

By Sissyplaytime April 6, 2025 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

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

By Sissyplaytime March 23, 2025 Cross dressing phone sex, lingerie, sissy phone sex
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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

Ms. Vickie wore a school uniform

By Sissyplaytime June 17, 2024 Cross dressing phone sex, sissy

sissy phone sexWow, I had a lot of fun last night with Ms. Vickie.  She got dressed up in a school uniform. I took her to the lingerie store and we had her fitted for a new Bali flower underwire 32B bra, in sissy pink.  She had on white cotton panties, and then we got her a little very short plaid skirt, blouse, with a tie, stockings over the knee, mary janes, and some lip gloss.

I could not resist, I sat next to her, she looked so lovely and adorable, I kissed her on the lips, and Auntie is a naughty girl, as My pussy was so wet. I slid my hand under Vickie’s skirt and played with her big clitty.  Before you know it, I was sitting on and and riding her.  We had wonderful lesbian sex.

I am looking forward to dressing Vickie up for school.

xoxo’s Ms. Kate for sissy cross dressing phone sex 1-888-833-1586

Sissy panty boy phone sex

By Sissyplaytime June 13, 2024 Sissy panty boy phone sex

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jeffietheloser: Go get your panties loser it is time for some sissy panty phone domination. If you are not sure whether you are a sissy, a panty-boy, or just a phone sex jerk-off loser, it’s OK, just call me, I will figure out what to call you. Some sissies call me in their panties and some need to be forced a little bit. Some are ready to suck cock for me and some need to start out slow, like with my big black strap-on. And some of my callers are straight vanilla type guys who are only hot for mean women, but who need to be put in panties to be humiliated. I get all kinds of calls. You are not alone. Many guys wear panties and many more want to but are too scared. You are one of the lucky ones because you have found a hot dominant woman who is experienced at sissification, humiliation and good
jeffietheloser: old emasculation.
jeffietheloser: When you call me for sissy panty hone domination you don’t have to pretend to be a real man anymore. I will strip away every last trace of “real man” that you may be hiding behind.  You will get too excited and dribble pre-cum into your panties, and you will need my humiliating guidance and control. That is what I am here for sissy panty boy!
jeffietheloser: For the best sissy panty phone guidance and domination call me at 1-877*368-7505

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

By Sissyplaytime June 9, 2024 face sitting, Humiliation phone sex, orgasms, queening
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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!

Debbie loves sissy phone sex and loves to be feminine and wants breast enhancement

By Sissyplaytime May 28, 2024 Feminization phone sex, sissy phone sex
Panty boy phone sex 1-877-368-7505

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Debbie is exceptional, not only does she love to be feminine, she loves sissy phone sex, and all the things that might help her to become a girl.  We spoke at great length, and she is very much still interested in having a boob job.  Debbie broke up with her old bf because she did not want to live with him or get married, and now is dating a new guy.  She is very popular.  Her old bf fixed her up with the new guy.  She is adjusting to a different way of dating. I think her first bf was great because he liked to take her a lot of places, and they had a very active social as well as sex life.

Debbie is a beautiful blonde, and she loves to be feminine, she has more clothes then I do, and that is saying a lot.  We talked about different dating scenarios and she is very interested in knowing about what is going on out there.

I can’t wait to hear about her new guy, what he might do next. I suggested she take a zumba class or dance, or cooking, so she can be with other girls. She thinks like a girl, and wants to fully embrace it all!

xox’s Jennifer

1-8773687505

Cross dressing for sissy sluts wanting feminization phone sex

By Sissyplaytime May 4, 2024 Cross dressing phone sex, Feminization phone sex, Humiliation phone sex, sissy feminization, Sissy panty boy phone sex
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Princess Elizabeth

If you love my lingerie even more than you love the sight of my scantily-clad body, it is time for you to explore
feminization phone sex fantasy world with some cross dressing especially if you fashion yourself a sissy slut. These sexy, pretty, naughty pieces of ultra feminine lacy, silky unmentionables would look amazing draping over your own body. Imagine these panties hugging your little cock and balls nice and close, my bra around you, stuffed with nylons, keeping your big fake breasts held up and looking amazing. Once you are all dressed up for me like a true pretty sissy slut, you and I are going to go shopping. With your credit card in my hand, both of us can pick out outfits together. Both of us will be getting dressed to the nines tonight, let’s really go all out, because I have a hot date surprise waiting at home.

Your sissy phone sex transformation awaits you once our shopping spree is over and we are at home. At home, you will learn to shave and pamper yourself just like a woman. You will be experimenting with pretty scented lotions, bubbles, makeup, nail polish, perfumes, you name it, you will be experiencing it. We have to give you the full feminization transformation so when my big dick stud shows up, you can show off and model to him, show him what a beautiful sissy slut you can be. You will love strutting your stuff in the new silky pantyhose and tall high heels we have gotten you, you will be walking like a sexy vixen in no time. Wouldn’t you love to play dress up with me? Just give me a call.

For the ultimate sissy cross dressing feminization phone sex experience, call Elizabeth at 1-877-368-7505
Email to set up a sissy session at PrincessElizabeth@sissyplaytime.com

Sissy panty boys enjoy feminization phone sex while cross dressing

By Sissyplaytime May 3, 2024 Cross dressing phone sex, Feminization phone sex, panty boy phone sex, sissy feminization, Sissy panty boy phone sex
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Shannon

I am of course your sissy expert, because I enjoy feminizing  sissy panty faggot boys looking for cross dressing phone sex.  I like to play with my sissy sluts, and other callers looking to explore their feminine side.  I love talking with sissies, cross dressers, and guys who want to experience the ultimate in feminization role play phone sex.  Tell me about your sissy experiences, and then we can create a new sissy experience for you, together.  We can go shopping if you are a real true cross dresser.   Most likely some of you are looking to live as a woman, I would love to have some girl chat with you, we can gossip and discuss the latest fashion, how you will be transformed into the best girl that you can be.  Some sissy’s just like to wear panties and are panty boys, and like to masturbate with my panties wrapped around their sissy clitties.

Femdom, sissy role-play scenario’s are very sexy on the phone, they turn me on as well.   A good sissy panty boy knows how to dress up and please me, because you are so very special to me, I will take extra time teaching you to be a girl, W/we can shop online, and get your wardrobe together, lipstick, panties, corsets, stockings and more.   Get on your knees and lick my ass while you serve me.    You are going to be my good girl and you at least give it some sissy effort, just for me.   Get ready to be trained to be a sissy, feminized and ready to serve a beautiful mistress, I am sure you want to be just like me.

Ms. Shannon for your sissy phone sex fantasy?
Then call Shannon at 1-877-368-7505
www.sissysessions101.com
Tell your sissy fantasy to me and set up an appointment sissy gurl!

Sissy panty boy wearing purple panties for his phone Mistress

By Sissyplaytime May 1, 2024 pink panties, sissy feminization
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Panty boy phone sex

One of my favorite sissy panty boys had a very special gift from his Mistress yesterday when she called me for a sissy phone sex call.  If you enjoy being feminized I do love feminizing you.  You will be may perfect panty boy.    It started the moment my sissy slut  entered my playroom.  She could tell that  there were plans underway to her feminization and humiliation.   I had arranged and  assembled a rather large group of observers for this occassion because in this sissy’s case the more public humiliation I subjected her to the better.   I will never forget the very first time I put her on public display.  She was wearing  her new sparkly purple panties.  She still wears and cherishes them, I even get to watch her in them on webcam.   Our sessions was so intense that my sissy cried, because  she  had one of the most intense orgasms of her  life.

I am known for being very  intuitive  and a great femdom phone sex Mistress if you are looking for someone who takes instant control.  I am very good at determining just what it is that you need when I meet a new sissy panty boy over the phone. So give in to your secret panty desires and get those soft silky underthings for me.

Call Cassandra for a sissy panty boy phone sex  fantasy 1-877-368-7505

Sissy panty boy’s get ready for foot fetish phone sex

By Sissyplaytime November 7, 2023 panty boy phone sex, pink panties, sissy husband feminization
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Jessica

Oh, the fun we are going to have during our sissy panty boy phonesex together! I can’t wait to get started playing with you, my new sissy playmate! I love it when you sissies call me up and say you want to try some new kinky variety, you want to dress up and completely let me take over, taking you above and beyond just being a cross-dressing sissy slut, into a true submissive, you tell me you want to experience it all, you just really want to please me. You tell me above all, you truly crave humiliation, and oh, lucky day, I absolutely adore humiliating you! Well, my new sissy, we can start off with some foot fetish phone sex. That’s something new to you, isn’t it? You can pretend that my pretty little painted toes are little tiny cocks. Show me what a good sissy cocksucker you can be, lick my toes, that’s right, just like a good girl. Oh, look at how pretty your lacy lingerie is! My oh my, do I see you developing a little clitty hardon, just from sucking on my pretty little toes? How about you reach into your panties and stroke that clitty for me, that’s right, go ahead, reach in there, and I will lead you to orgasmic bliss. Dial Jessica for sissy panty boy phone sex at 1-877-368-7505