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 22

2025

Feminization Phone Sex with LanaFeminization Phone Sex with Lana

“I’ve never even touched another cock” he said the first time we got together for feminization phone sex. I reminded Dave that this was his idea, for us to meet up and for me to push him past his comfort zone and make him my bitch. His curious dick was poking through the flap of his boxer briefs as he swallowed nervously and looked down at the shadows on the carpet. I’m an understanding and patient lady but this was getting ridiculous.

I stood up and walked over to my dresser and pulled out a pair of dark green lace panties. They looked like they would fit him so I tossed them to Dave and told him to change out of his boxer briefs and into the panties. He started to give me some lip about it. I cut him off telling him that maybe part of his hang up about going forward was the fact that I was treating him like a man. I let him know that from that moment forward that I would be treating him like another woman.

“Stop messing around and get those panties on, slut!” I ordered him and he got up and started yanking down his briefs and pulling up the dark green bikini cut lace panties. I pointed to the floor in front of me and let him know that was the spot that I wanted him kneeling at. I told him that he was just my sex toy for the evening, and I would use his holes to get my pleasure whether he came or not. He dropped to his knees and I told him what a pretty sissy he was, and what a good cock sucking girl he was going to be for me. Dave moaned at that and looked up at me and I told him to take my cock out and get it fully hard before sucking it.

Call me at 1 888 72 KINKY and ask to talk to Lana for feminization phone sex

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 29

2024

Sissification Phone Sex with CarmenSissification Phone Sex with Carmen

Do you want to be feminized but aren’t really sure where to start? When you call me for sissification phone sex, I will help you with every single thing along the way. If you want to look like the gorgeous woman you’ve always wanted to be, I am the one you need to call. I understand that it can be totally overwhelming and hard to even know where to start. There’s lingerie, makeup, hair, nails, heels and many other things that you’re going to have to become an expert in. The thing I always tell my callers to do is put on a pair of panties if they haven’t already. That will just automatically make you feel more feminine. Then you will be in the proper mindset to start talking about all of the ways I’m going to help you feminize yourself. Are you ready to take that journey with me?

You may or may not want to do more than look the part of a woman. Of course, I’m talking about being fucked or sucking cock. It’s total cool if you don’t want to talk about that on our sissification phone sex call. But if you do? Oh, I have so many sex toy recommendations for you. Of course, I can help you work toward sucking and playing with a real cock, but you need to get used to having your holes filled up before you get in the room with a real one. We can explore all of this and more. I’m ready to turn you into the sissy of your dreams. All you have to do to make it happen is get on the phone and call me. Dial 1 888 72 KINKY and ask to talk to Carmen right now to begin the transformation you need.

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.

Jul 10

2024

Bimbofication Phone Sex with CaitlinBimbofication Phone Sex with Caitlin

Of course, sissies are out there but I want to talk to you about something that goes further than that. I’m talking about bimbofication phone sex. I want to take you from a regular sissy and turn you into a dirty, ditzy blonde bimbo who more than loves to fuck. You will NEED to fuck by the time I am done with the bimbofication process. You will be so dumb by the end of me turning you into a bimbo. It won’t be that you don’t ever think about anything other than cock. But you won’t even be able to. It will never even occur to you to think about anything other than fucking. And you will never be the one with the ideas for sex. You’ll basically just be a living, breathing sex doll. You will be more than happy to know that that’s all you are good for.

We’ll have to make sure you look the part of a bimbofication phone sex slut before we do anything else. You’ll have big, teased, curly blonde hair with so much hair spray that you’ll probably be considered a fire hazard. You’ll be spray tanned and have so much makeup on that you will look like you rolled around in the beauty section of Walmart. And don’t even get me started on how you will be dressed. You’ll probably be wearing a selection of mixed animal prints that would make someone wish they were blind. But that’s just how bimbos dress, so you might as well get used to looking like that. Are you ready for our bimbofication phone sex call? I’m ready to turn you into a dirty bimbo, but the question is – are YOU ready? Get on the phone and call me. Dial 1 888 72 KINKY for Caitlin.

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!

May 05

2024

Feminization Phone Sex with MadelineFeminization Phone Sex with Madeline

There are so many of you out there who want to be sissified and that’s definitely doable, but you have to get on the phone and call me for feminization phone sex if you want to do it well. Sure, you could probably go online and find all the tips that you need, but there’s nothing like having a friend help you out. I can’t even tell you how many guys call me up and tell me that they’re so thankful that girls like me exist because they’re totally clueless. And when you’re talking to a younger girl like me, you can be sure that you’ll look fresh and updated with all the latest trends and all that stuff. I won’t let you leave the house looking like a drag queen from way back in the old days. You will look like you walked out of a fashion magazine, sissy!

You are probably going to have to do a little bit of shopping after our first feminization phone sex call. It depends on what you already have there with you when you call me. I hope that you’ll at least have some panties and a tube of bright red or pink lipstick to wear while you talk to me. But if not, don’t worry, we will take care of all of that – I’ll tell you what to buy and you’ll buy it. Are you ready to talk more about how the feminization process works? Don’t worry, your sissy transformation will be complete soon and then we can get started on the next phase. You’ll have to call me to find out what that is. Just dial 1 888 72 KINKY and make sure you ask to talk to Madeline for feminization phone sex. I’ll be waiting for you, cutie pie!