Sissy Training Phone Sex Archives

May 12

2025

Forced Feminization Phone Sex with SadieForced Feminization Phone Sex with Sadie

You probably didn’t know that you’d be getting forced feminization phone sex when you called me. You thought you were a sissy panty boy but you had your doubts. Some girls even let you fuck them while wearing lingerie. That’s before you encountered the freaky fetish girls though. I know you’re really not a man and I’ll do anything I need to do to make sure you realize that. I’m not stopping at just panties or even just lingerie. You don’t have a chance of seeing my pussy until you’re fully into forced feminization phone sex. Even then it will only be to worship it before I make you put my strap on on for me so I can fuck you like the sissy bitch you really are. Did you think you could fool me into thinking you were a man who just sort of occasionally wore panties and that was all?

Forced feminization phone sex freaky fetish style means that you will have feminine hair and you will remove body hair that prevents your sissy clothes from looking pleasing for me. You will work with me to talk more like a woman and you will fuck like a bitch in heat when I present my strap on to you. You will wear makeup that I pick out and you will work very hard at applying it well and making sure I’m proud when I see the progress you’re making. Forced feminization phone sex doesn’t end with the phone call. It stays with you long after you hang up. You’ll be wondering what you can do to make Miss Sadie happy with you and how far can you go to make sure that your sexy MILF Mistress proud of her forced feminized whore.

You will no longer have a choice in being a sissy or being a boy. It will all be decided by your new forced feminization Mistress. Call me at 1 888 72 KINKY and ask for Sadie.

Apr 13

2025

Sissy Phone Sex with AbbySissy Phone Sex with Abby

It’s the time of year that I do a lot of spring cleaning. It would be wonderful to have one of the many sissy phone sex callers I talk to come and help clean up. Good sissy boys get rewarded for making their lady happy and making her day easier. I was telling Sissy Noel about this and she said you usually just humiliate me Miss. This is true, I give that pink loving sissy boy lots of humiliating tasks to complete but Sissy Noel needs it. What she failed to mention was that usually when she finishes one of these many humiliating assignments she gets a reward. Maybe she doesn’t always see it as a reward. Is being allowed to cum a reward? Well it sure is. Is it still a reward if you have to do it on cam in a tight corset into an ice cream cone for your lady and then eat it up as she laughs? The way I see it is that she still gets to cum.

I get a lot of pleasure and enjoyment out of humiliating sissy boys and that’s why I get excited for sissy humiliation phone sex. People tend to think of sissy as being a weak word but when you think about the humiliating assignments completed by sissies they’re anything but weak. I don’t know about you but there aren’t many men I know who would humiliate themselves in the way the sissies I know do. You could argue that it is because real men wouldn’t even begin to do the things the sissies do in the assignments. If there were men and not sissies they would say no and never do it. Maybe that’s true but I think some of the blushing soft sissies are very strong individuals who happen to have fun with the assignments their Mistresses give them.

Call me for sissy phone sex at 1 888 72 KINKY and ask for Abby

Mar 22

2025

Feminization Phone Sex with NadiaFeminization Phone Sex with Nadia

Hi sissies. Do you spend an inordinate amount of time daydreaming of girl life? It’s alright if you do. Life as a lady is wonderful. What part of the female appearance do you crave the most? Are you addicted to panties? Do you go crazy over high heels? Have you been practicing your smokey eye look for years now? I want to hear all about your sissy side. I love having feminization phone sex. As a domme I love to feminize men too. If you need a push in the right direction and want a take charge woman to take control over you and make you her girly toy, call me up. We will get along just fine. I’ve been dressing boys up to look like girls for a very long time. Some of my best male friends are sissies. Do you have a real time domme that feminizes you?

If you are in need of female guidance and sissy training, I’m your woman. You can call me and get trained in all things feminine. Feminization phone sex makes for a great two girl call as well. Any of the women here would be a good fit for us to feminize you together. You can just tell us your feminization fantasies and we will do our best to make it happen for you. Does that excite you? Do you get warm and tingly thinking about being exposed and then feminized by two gorgeous women? It thrills me to think about playing with you and another domme. If that’s too much we can definitely keep it one on one though. I want to be your girlfriend, lover, domme or whatever role you need a female leading you from. We can roleplay with me as your teacher, boss, whatever you so desire.

1 888 72 KINKY and ask to talk to Nadia for feminization phone sex

Feb 02

2025

Sissy Training Phone Sex with LesleySissy Training Phone Sex with Lesley

If you’re looking for someone to guide you through becoming a sissy, you need to get on the phone with Lesley for sissy training phone sex. Who better to help you than someone who has started out just like you are. Maybe you’re not trans, but I can still help you with your journey because I’ve feminized myself from head to toe. I’ll want to know all kinds of information from you when you call me. I’ll want to know your body type, skin tone, height, etc. I’ll need to know those things so I can help you pick out what to wear. I can’t tell you what color you will look good in if I don’t know your skin tone now, can I? Once I have that info, we can talk about what kind of panties you like – color, cut, material. Everyone has their own preferences when it comes to those things.

And I’ll also need to know if you’re the kind of sissy who just wants to get dressed up or if you want to learn to be treated like a woman in every single way. I know that playing with a cock other than yours can be intimidating the first time you do it but trust me – you will be a pro in no time. I’ll be a little different since you’ll be taking on the role of the woman, but you’re going to do great. I think that you’ll really get a lot out of sissy training phone sex with me because not only do I know how to make you look the part – well, I’m also a dirty slut and I love cock. So I’ll be able to teach you everything you know. Get on the phone for some fun with me now! Dial 1 888 72 KINKY and ask to talk to Lesley!

Oct 17

2024

Sissy Phone Sex with SapphireSissy Phone Sex with Sapphire

When it comes to sissy phone sex, I feel like calling a shemale Goddess like me will give you exactly what you need. See, I know that in addition to getting all dressed up, many sissies really love cock. They want to play with it, suck it, get fucked by it. With me, you get the best of both worlds. I’m super feminine and can help you with your sissy transformation if that’s what you need. But what I can also do is push you down on your knees and push my hard cock down your throat. Do you want me to slap it on your face before I put it in your mouth? Maybe I’ll rub it on your lips so that my pre-cum makes it look like you are wearing the most expensive lip gloss. Do you think about sucking cock? You need to call and tell me about it.

But if you need to be fucked, well, I’m your girl for that, too. I would love nothing more than to bend you over after you’ve sucked my cock to get it hard again. And if you’re a virgin and have never been fucked? Well, that’s even better. I love being the first one to fuck a tight asshole. I love knowing that my cock is the first one someone has felt inside them. Even if they have played with toys before, it’s not the same as having a real, throbbing dick inside that tight ass. So, no matter what kind of sissy phone sex you want, whether it’s just dressing up or the total sissy whore treatment, I’m the one for you. Do you want to hear more? Get on the phone and give me a call right now at 1 888 72 KINKY. Ask for Sapphire.

Jun 28

2024

Sissy Training Phone Sex with GypsySissy Training Phone Sex with Gypsy

I have a question – is there anyone out there who is in absolute desperate need of sissy training phone sex? If you are brand new and you just aren’t really not sure exactly where you should start, then I am definitely the woman you need in your life. You could call a younger girl and I am sure she would do a great job. But I’m more mature and I definitely have had a lot more experience to draw from when it comes to guiding you on your feminization journey. I have done so many things and I have watched so many things happen that I know I’m the right one to help you out. If you are ready to get started on the sissy transformation journey that will take you to places you could never have even imagined, that means you need to get on the phone with me.

Sissy training phone sex is about a few different things – your mindset, your physical appearance, and your ability to take a cock in your slutty holes. Sure, they might not be slutty yet, but I promise you that by the time I am done with you, they will be. You will be a dirty whore that men are happy to see walk into the bar they are in. I bet cocks will even start to get hard when you walk in because they know they can take you in the bathroom and pound you in whatever hole they want. You can either hike you dress up over your hips and bend over or you can squat and open your mouth to get your face fucked. When you are ready to begin your sissy journey, get on the phone and dial 1 888 72 KINKY and ask to talk to Gypsy!

Apr 17

2023

Sissy Phone Sex with AbbySissy Phone Sex with Abby

Hello to all of you sissy phone sex faggots! It’s nice to freaking meet you…well, it will be once you call me. See, sissies are probably my very favorite kind of caller. It’s not that I don’t want to hear from anyone else. That’s not the case at all. I just happen to have quite an affinity for sissies since that was the first kind of phone sex call I ever took. I’ll never forget it, and in a lot of ways, it kind of shaped who I’ve become as a bratty dominatrix. I don’t think I’d ever be able to give up feminization calls. I love helping all of you sissies get dressed up and ready to go out on the town. We can talk about what kind of colors you’d look good in, what styles of lingerie might fit your body type, and any number of other things.

But what I really can’t wait to get to is teaching you to suck cock properly. If you’ve ever had a blow job, you have a pretty good idea of what to do, but there’s nothing like actually having the experience of sucking a cock yourself. Once you do it, you’re never going to want anything else, so I want you to really be aware of that, sissies. There’s no turning back once you fully give in to your sissy faggot side. Do you think that you are ready to be trained and feminized by one of the best sissy trainers around? I hope so, because I love molding sissies into the women they were always meant to be. Get on the phone right now for sissy phone sex and begin the transformation process today! Just dial 1 888 72 KINKY and make sure you ask to talk to Abby.