Sissy Training Phone Sex with Ruth

Welcome, ladies, to Ruth’s sissy training phone sex school, the premier place to make your dream transformation come true! When you applied to join this elite class of caterpillars yearning to be beautiful butterflies, you agreed to leave behind your whole life before. You will eat, sleep, and breathe your sissy training under my master tutelage, and you will thank me for it every time with a polite little, “Thank you, Mistress.” Just the way a good sissy does.

sissy training phone sex

Your first sissy training lessons will be about your outward appearance. No more pants and suit jackets for you, no sirree, sweetheart! From now on you will dress like the sissy girl you are. Your shoes will always have a heel of 2 inches or more, and you will always wear stockings of some sort. Believe me, sweetie, you will grow to love the silky feeling on your legs and the way the heels make your ass wiggle when you walk! All of your skirts must be shorter than where your fingertips rest on your thigh, and you must show plenty of your cleavage at all times. After all, what good is a sissy whore trained up all proper if you can’t grab the right kind of attention? In addition to your clothes you will of course learn how to properly apply makeup and style your hair and nails so you look like the most glamorous lady all dolled up for your days in the office and your nights out on the town.

But that’s just the packaging. Once you go through Ruth’s sissy training phone sex school you will be the ultimate sissy inside and out. You will be taught exactly how to suck cock of all sizes, because while you may find you love big thick dick, a good sissy will take any stiffy that comes their way! And Mistress Ruth has all sorts of strap-ons to teach your sissy ass how to get fucked like the champion slut you always wished you could be!

Call and apply for Mistress Ruth’s sissy training phone sex school right now, sweetheart!

Skype: Red Hot Ruth
Twitter: @RedHotRuth

Small Penis Humiliation Phone Sex with Samantha

OMG I totally love it when guys call for small penis humiliation phone sex. I don’t know what girl wouldn’t love it. It cracks me up that you would willingly take your clothes off in front of a girl like me and expect that it would turn me on. There’s no way in the world that I would ever let you near me with that ridiculously small “dick”. It makes me laugh so hard when you tell me that it’s not the size that matters, it’s how you use it. Honestly, I don’t know how you could even think it would go inside me. It’s bad when your dick isn’t even big enough to go inside a girl. You know that right? Just thinking about watching you try to fuck someone makes me laugh out loud. But no, I don’t want to let you try to fuck me. It’s not THAT funny. That’s so gross.
small penis humiliation phone sex
 
You know what I think? You probably should be wearing panties instead of men’s underwear. I want to take you to Victoria’s Secret and make you go in and tell the sales girl that you need to buy some panties. She’s going to ask who the lucky girl is that you’re shopping for and I don’t care how humiliated you feel, you’re going to tell her that they are for you. You should also tell her that your dick is so small that your Goddess said you aren’t allowed to wear men’s underwear anymore. Then you’re going to ask her for the sexiest pair they have in the store. I’m just going to stand back and watch and take some pictures. You’re totally going to want to remember the experience.
 
Are you ready for some small penis humiliation phone sex with Samantha? All you have to do is call me at 1 888 8 FREAKY!

Sissy Phone Sex with Amber

You sissy phone sex boy, enjoying your pretty pink panties. They make your little cock all hard, don’t they? Look at your little cock just hanging there and that little set of balls, no bigger than two grapes. I think you need to put on your pink panties with the leopard skin waist band in order to hide that poor excuse for a cock. How cute!

sissy phone sex

You’ve been in the bathroom way too long. I stand at the door and listen to see if I can hear what you’re doing. Moans and groans, just like a girl is what I hear. I can’t help but open the door. And there you sit on the toilet with your panties down around your ankles and playing with your little cock. I can’t help but stand there and laugh at you. You need to have sissy phone sex.

Standing up from the toilet and bending over while you take a big dildo out of the vanity draw, ant to you beg me to fuck you. I tell you that I want to see you suck on the dildo before I fuck you. So I walk around you and hold the dildo against me, just like I have a cock. And I tell you to suck on it just like a good little cock sucker. I laugh my most devious laugh I can muster.

Watching you suck that dildo was starting to get me excited. I find myself wanting to fuck you, pulling the dildo out of your mouth and telling you to turn around so I can fuck you like a little Bitch…your ass is gaping wide open. So I stick the dildo in your ass and start fucking you…this is very fun and exciting me to the point of my pussy starting to get wet. I look down and notice your pink panties still around your ankles.

Call me at 1 888 8 FREAKY and let’s have sissy phone sex together!

Cross Dressing Phone Sex with Jocelyn

I have the cutest slut calling to talk all about cross dressing phone sex! *giggles* And let me tell you, this kinky cute girl next door has heard a lot, but some of the things this horny bitch gets up to can make even me blush!

cross dressing phone sex

I love this bitch’s double life. Conservative suit dressing business man by day, this bitch gets all sexy and slutty to go partying just about every night! My cross dressing friend likes to hit up the bars with their hot cross dressing best friend and find hot and horny guys to party with. I love when my little slut tells me all about choking on a new thick cock back in the bathroom. This whore’s face is so hot when its running with mascara and she’s begging to take a load all over her tear-stained cheeks. The two little bitches usually do even better though and bring home a few guys to fuck their eager asses while they drink and have fun doing party favors that make them so horny *giggles* It makes me all hot and tingly wet to hear how much this slutty cross dressing caller loves to bend over the couch and take a big black cock hard and deep. I can’t help but reach down to part my slick pink lips and play with that sweet love button that makes me purr!

Something about a gorgeous cross dressing whore begging for a big daddy to plow their slutty mancunt just gets me all sorts of turned on! And when they want it rough, begging for daddy to hold them down and make it hurt, all their whimpering only makes my fingers fuck my tight sweet hole even faster!

Do you have what it takes to be my cross dressing phone sex slut? Call 1 888 8 FREAKY and ask for Jocelyn to find out!

Skype: Jezebel Jocelyn
Twitter: @JezebelJocelyn

Sissy Training Phone Sex with Riley

Damn, that boy can’t handle the simple things in life, like getting himself dressed properly. He would lose his head if it weren’t attached to his body! I have to tell him how to dress, and it isn’t just because of a lack of style, but it’s also because he’s simply useless without the guidance of a woman like me, who knows how to make heads turn. He would make such a pretty gurl too, so I think I’m going to start giving him the sissy training phone sex he’s so ready to receive. First we have to attack that face with a pair of tweezers! I’m going to show him how to pluck those caterpillars over his eyes and turn them into graceful, feminine brows. Shave that pretty face and body next – get it all nice and smooth! After that, his sissy training will involve a tutorial on how to apply makeup, both on his face, and on his chest to create the look of some hot cleavage. Atta girl – there you go – lots of red lipstick on those pretty lips!

sissy training phone sex

The next step in sissy training is exactly what this boy needs the most – he needs a woman to teach him how to get dressed like the hot sissy whore he has hidden away. I’ll lay out all the clothes for him, step by step, so he sees what a complicated process it is to dress like a woman. He can’t handle dressing like a man, and maybe it’s because he secretly doesn’t like wearing men’s clothing. His eyes are lighting up at the sight of those lacy panties and bra, the silk stockings and sexy garter belt, the tiny mini skirt that will show off his girly legs, low cut blouse, and the long, beautiful wig laying next to all the clothing. After I teach him how to put all of that on properly, his sissy training will be finished off with a sexy pair of high heels, of course with some instruction and practice on how to walk in them. A cute purse, a falsetto voice, a name like Tiffany, and we’re ready for a girls’ night out, picking up all the hot guys we can fuck!

Call 1 888 8 FREAKY and ask for Riley for sissy training phone sex!

Twitter: @ReadyRiley

Panty Boy Phone Sex with Phoenix

There’s nothing that gets me wetter than talking to a panty boy. Pantyhose, garters or just white cotton undies – no matter what a panty boy wears it turns me on. Panty boy phone sex is the absolute best! Never has the phrase “What are you wearing?” been so appropriate. I want details darling. Where you got them. When you wear them. How they feel. Why you wear them.

panty boy phone sex

I love it when you call me when you first put on the panties. I love it when you tell me all about the style and fabric of your panties. I love it when you tell me how hard you’re getting against the fabric.

Panty boy phone sex is often so hot and I feel like such a slut, I often start roleplaying and pretend they are my panties. I’m your girlfriend and I’ve walked in on you wearing my favorite pair of panties. Instead of getting mad and yelling at you, I get a wicked smile on my face and walk over to you – touching the edge of your growing bulge with my fingertips. My hands feel so good on the fabric, you rise to attention and we take everything from there.

Or maybe you’re a sissy slut? Maybe wearing the panties make you think about what a good cock whore you’d make. You look so good in those panties you’d pull them down for my big strap on. You’d slide those panties down your firm ass cheeks and I’d take you from behind.

Panty boy phone sex can go so many different ways. I love exploring the limits with you and your favorite pair of silky panties. I’m ready for mind blowing panty boy phone sex – are you?

Call me 1 888 8 FREAKY ask for Phoenix

Twitter: @PlayWithPhoenix
Skype: playwith_phoenix
Yahoo: playwith_phoenix

Cross Dressing Phone Sex with April

Have you been into cross dressing for a while now, but you’ve only ever been brave enough to do it at home? I know that it can be hard to be confident enough to go out into the world and let people see you dressed as a woman for the first time, but I promise you that it won’t be nearly as scary as it seems. And if you still feel like you aren’t brave enough, call me for cross dressing phone sex and I will be more than happy to talk you into it. Trust me – you’re going to be so excited and feel such freedom once you step out all dressed up.

cross dressing phone sex

I want you to go into your closet and pick our your sexiest panties and bra. You have to start with a good foundation. If you feel sexy, you’re going to BE sexy. Then I want you to put on a garter and stockings. Slide the perfect little black dress over that and look in the mirror. You look AMAZING. Oh, one last detail. Put those stilettos on and stand tall. Don’t you feel SO sexy? See, I knew you would. You just have to have a little confidence.

I can’t wait to see how many men will hit on you once you make it to the bar. Do you think you’re gonna be confident enough to flirt back with them? You look incredibly hot, so you should be! I bet you’re even going to end up on your knees with a fat cock in your mouth. I mean, you haven’t told me that’s what you want yet, but I just have a feeling you do!

Ready for some kinky cross dressing phone sex? Call me at 1 888 8 FREAKY and ask to talk to April.

Feminization Phone Sex with Vienna

Maybe it’s the pressure you’re under, working 40, 50, 60 hours a week breaking your back while your asshole boss busts your balls, all so you can hold shit together for the wife and the kids. Whatever the reason, you just ache for a few moments where you don’t have to be the strong one. If that sounds like you, then maybe an hour or so of feminization phone sex is what you’re needing. That’s what did it for me. I had what I thought was the dream – wife, kids, house in the ‘burbs, steady job. I mean, what more could I want, right? Well, the wife was a fucking nag, demanding I do all the heavy work so she could “relax”, making me take charge in the bedroom; the kids were always breaking something or screaming and fighting; the house took every extra minute I had to keep things looking good; and my boss got off on making me look like an asshole in front of the guys. It was more than I could take!

feminization phone sex

Then one night, I couldn’t get it up for the wife and she kicked me out of the bedroom, so I ended up calling one of those feminization phone sex lines. My life was changed forever!! The mistress on the other end of the line was caring and patient, and, more importantly, she wanted to take charge! I didn’t have to be “that guy” to her. I could cry if I felt like it, and I learned to be the soft sissy I always dreamed of being! You can have that, too!! Take a break, Honey, and let Miss Vienna take charge. You’ve always known that the best part of being a woman had to be not having to think, right? No decisions, no pressure, just following orders. Well, you can have that, too, you little slut – just call for some much-needed feminization phone sex and let me take full control!

AIM: vixen_vienna4u

Fetish Phone Sex with Jocelyn

What flavor of fetish phone sex do you crave today, you kinky pervert? As long as it isn’t plain old vanilla, I’ve got every possible erotic taste you could imagine, and in the best sensually swirling combinations, too!

fetish phone sex

When you call me you know my fetish desires crave every kinky taboo thing you can dream up. Maybe you have a fetish for fuck me heels. Your cock twitches with every single click of my pretty feet in 6 inch stilettos. The sight of my ass wobbling above those spikes makes your mouth water. You want to beg to curl your unworthy tongue around my toes.and worship my perfection before I dig my heel into your ass cheek.

Maybe your fetish runs even more taboo. You’re the kind of twisted fuck who wants to get off eating another man’s cum out of my creamy center. You even sat and watched while he pounded my pussy right in front of you. Creampie fetish phone sex is the best when I sit on your face and grind my cummy cunt all over you.

Maybe you think your fetish phone sex request is going to be too far or too weird for me. I am telling you right now: it is not. possible. I am a fuckaholic freak and I haven’t found a single fetish that turns me off yet! The mild ones are fun times for everyone: tickling, spanking, stockings and heels.

The ones where it gets midsized freaky can scare some of you off. But I know lots of you pervs out there are drooling with anticipation to call for fetishes like big black cocks, feminization, and panty play. Aren’t you lucky I get off with all of it, too? I even get wet when you get adventurous and start asking for socks, or blasphemy.

Do you think you have what it takes to try me out for even your darkest fetish phone sex fantasies? My dirty mind and your kinky desires will lead us into deep dark holes to explore! Call me at 1 888 8 FREAKY and ask for Jocelyn!

Twitter: @JezebelJocelyn
AIM: PlayWithJocelyn
Yahoo: CumPlayWithJocelyn

Sissy Training Phone Sex with Beth

You can’t deny what’s inside of you – you’re a sissy gurl and you need to acknowledge that now, only you don’t know where to go from here. You want to know what it’s like to have your outside match your inside, but you’re lost in the woods and you need help. You need some serious sissy training phone sex, so you need to call Beth. We can take that gurl you have inside and transform you, and once we have you looking the part, you will learn how to act like the little sissy bitch you are. I’m sure you’ve already dreamed of the things you could do once you stop denying your sissy tendencies, and now it’s time to make it all come true.

sissy training phone sex

Sissy training with me will include lessons on shopping for girly clothing, everything to suit your sissy gurl needs from lingerie to dresses, and from wigs down to your shoes. I will teach you makeup techniques, like how to get the perfect eyebrow shape, and how to make your lipstick stay on all night – even when you are going to be a naughty sissy slut and give a cute guy a blowjob, which of course I will make sure you know how to do like a champ. I’ll show you how to tape up your chest and use body contouring makeup to create the perfect cleavage. We’ll get waxed together, work on making your voice sound feminine, and I’ll teach you how to walk in the sluttiest of high heels. Sissy training phone sex covers all of these topics, plus I get to train your little sissy boy cunt to take all the cock that’s going to be lined up for you when you’re ready for your pretty little sissy face to be seen by the big, bad world. My strap on is ready to make you my bitch and take your pretty little cherry! Cum on gurl….you know you want it, so call!!

Call 1 888 8 FREAKY and ask for Beth for sissy training phone sex!

AIM: Beth_cumsxxx
Tumblr: bethcumsxxx4u