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.

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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.
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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 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

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

Sissy Phone Sex with Tranny Cheyenne

Sissy boys, it’s about time you got real. And it’s about time you got into the phone sex you really need the most,  sissy phone sex with me, a sexy Tranny. I already know the sissy secrets you hide from everyone else. Or you wouldn’t even be calling me. I know how much you fantasize about going all the way and transforming into a shemale. You can’t hide that you wish you could abandon your life as an inadequate man and give in to your dazzling dreams of becoming a real life TGirl. You have what it takes to start, sissies, but you need to begin phone sex transformation sessions where I will be your guide.

sissy phone sex with a shemale goddess

Look at my photos, you’re jealous, aren’t you? You want to be a sexy shemale and do nasty phone sex, seduce men, even become a tranny hooker. I’m familiar with the total trans lifestyle and can tell you the exact steps you need to take in order to leave behind your sissy self and become a tranny Goddess. You will need to walk and talk like a girl, look like a girl. Be a girl! By the time I’m done with you, no one will recognize you. You will be mine, a perfect shemale dolly.

I’m very supportive in my approach to transformation, but I expect results. The second you first slipped on a pair of panties has led you to this moment. It’s time to go even further than ever before. Sissy Phone Sex with a sexy shemale Goddess is the sexual destiny for you sissies. Don’t run away from it, my sissy boys! You know you want it and more importantly, need it.

For sissy phone sex call 1-888-837-3259 and ask for Shemale Goddess Cheyenne to start your training.

AIM – CheynnesDirtySecret

Sissy Phone Sex with Goddess Connie

Sissy Phone Sex with a dominant femdom who will make you into the sexy girl you always wanted to be, just what you’ve been looking for!
Sissy Phone Sex
I love giving all the naughty cross dressers sissy assignments phonesex, how about we go shopping for a cute little outfit, from head to toe, silky panties, push up bra, thigh high stockings, and of course, shoes to begin your sissy phone sex transformation, you know this is making you want to touch your sissy clitty!
I always have lots of creative sissy phone sex assignments, and I’ve been handing out sissy bitch assignments to all the good little sissy submissives, and I’ve been playing lately with bombshells in corsets and latex, doesn’t that sound like your sissy fetish?
If you’ve ever had freaky fetish phonesex with me, you know how much I love giving you the unique beautiful female perspective on how to make you more feminine, pantyboy sissied and pantied for life training, and of course, strapons!
Just imagine how amazing it is on a sissy phone sex call with me, my sexy voice seducing you in your pretty ear, making you blush and simper when I put you in something to make you so sexy and womanly, indulging your inner sex kitten to make your femdom mistress happy, cross dressing for your Goddess!
Your total feminization journey begins with a call to the best sissy phone sex Goddess ever!
And just like any girl ever, sissies are so individual in what they like, so make sure to tell me just what kind of sissy you are, what gets you all horny, is it cock, strap ons, being pimped out, or just being made into a real girl?
Call me now for everything sissy, I absolutely adore and love indulging in feminization assignments and transgender as well as sissification phonesex!
Connie
AIM:CuckoldPhoneSex
YIM:CuckoldStoriesPhonesex

Sissy Training Phone Sex with Trinity

I put men in their place on a daily basis, so when they approach me with sissy training phone sex, I jump at the opportunity to teach them a thing or two. Many men have always possessed the trait to be a sissy but never knew what to do with their urge to dress and act as a woman. Some of them are married and have lived very masculine lives for years but always felt as if something was missing. I like to guide them with my mind and cock to make them into the best sissys they can be.

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The first man who contacted me asking for sissy training phone sex was a guy named Tom. He was middle aged and expressed that he always has had the urge to be a sissy. When he was younger he would go into department stores and try on women’s panties. His urges just got worse as he got older and finally married and began wearing his wife’s panties and bra under his business suit during his work day. He told me he would go into the bathroom stall at work and rub his nipples through his intimate garments and imagine how it would feel to receive a facial.

He craved sissy phone sex training from a real tgirl so he came to the right place. My cock grew hard as I guided him to it and told him to open wide. I explained to him that every good sissy knows how to give an excellent blowjob on command. Once he got it nice and wet, I made him turn around so I could get a good look at his man pussy. It was gaping and ready for entry but I wasn’t going to give him my cock. Instead I got a ten inch dildo and shoved into him and watched him beg for mercy. Ready for you sissy training phone sex session with a dominant t-girl? Then call me Trinity at 1 888 8 FREAKY.

Slutty Sissy Phone Sex with Carla

It’s Friday and I have a special night out planned for on our slutty sissy phone sex call. First thing I’m going to do is dress you up like the perfect slut. Stockings and garters with your little panties pulled over the garters. We need to be able to take them off without taking off those stockings. I think a proper slutty sissy needs to have big tits, so let’s get you a bra and stuff it full. A super short mini skirt and a sheer white blouse tied up to show your belly button.

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Our first outing for the evening is to my favorite fetish shoe store. No sissy slut outfit would be complete without a pair of 5″ heeled cum fuck me pumps. After I pick out the perfect pair for you, it’s time to pay the man. Oh you forgot your wallet? I think there are other ways of paying up. He leads you to the back room, you get on your knees, and he pulls out his hard fat cock. With my hand on the back of your head, and my other hand on his cock, I tell you to open wide and start sucking like the slut you are. An experienced slut like you should have no problem taking his dick balls deep and sucking every drop of his precious cum. You better not miss any and ruin your outfit or his pants. Don’t make me spank you right here in front of everyone.

A quick stop at the salon for my girl to do your make up and hair. Shiny red cock sucking lipstick, extra long eyelashes, red rosy cheeks, and a long blonde wig complete your look. Perfect for our last stop at my favorite toy store. There is a special event tonight and you are the star. Not only are we going to try all the new dildos and strap-ons, all the guys are going to need someone to take care of their hard cocks. I tie you to a spanking bench, ass up in the air. I pull your head up by your collar so your mouth is available too. When you see them lining up for your sissy slutty boy pussy and your hungry mouth, you can’t wait for the real action to begin.

For slutty sissy phone sex, call Carla 1-888-837-3259

AIM – MILFCarla4u

Sissy Phone Sex with Julia

I get asked from time to time about what my favorite type of call to take is and honestly, I always find this to be so difficult to answer because each and every one of my callers is so very special in their own way! I will say this though; the most entertaining type of call I get are from my sissy sluts. Yep, that’s right, these guys want nothing more than to be turned into the perfect sissy bimbo and they know to call me because I’m the one that always gets the job done right! Let me guess, you’re one of the sissy boys, aren’t you?  Sissy phone sex with me is perfect for you then!

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How big of a sissy slut are you? I am looking for open minded sissy bimbos to have sissy phone sex with. Are you willing to push your boundaries and limits like never before? We can go as fast or slow as you’d like because when you want something done right you must be willing to explore it all. I’m talking about the whole package. I need my sissy to wear pretty lip gloss, nails painted, high heels and wigs…  I love putting her in pretty bras and matching panties and of course dresses too.

Are you longing to be a perfect sissy? Well, when you call me for sissy phone sex I will turn you into just that. I am the perfect girl and I want to get you as close to perfect as possible, too.  You do know, though, that it’s going to take a lot of work, don’t you? I mean, you’re not really a “mans” man, but you still have obstacles to overcome! Together, we’ll make you the sissy slut you’re supposed to be during our sissy phone sex session.

AIM: sweetjulia_4u
Yahoo: sweetjulia4u

Sissy Phone Sex with Lola

I’m ready today for some cock sucking sissy phone sex sluts. I know you’re out there. I talk to you all the time and I know what dirty whores you either are or want to be. And if you need to be turned into a whore, I’d be more than happy to give you a hand with that.

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First, I have to ask you something – have you ever sucked cock? Have you ever had a big fat toy or dick in your pussy? If not, that’s gonna take some getting used to, so you’d better make sure you’ve practiced enough before you get to work on those real cocks. I believe in doing things big or not at all, so for your first time getting all dressed up and playing with real men, I think it would be fun to rent a hotel room for the weekend for you. Then we could place an ad online or something to get a bunch of guys to the room for you to play with! How many do you think you could service in a weekend, sissy slut? I mean, you’re probably going to have at least 10 per day. There will surely be tons of guys lining up for a free blow job or the opportunity to fuck a sissy whore like you.

I wonder which one of your holes will be used up first? Will your jaw be too tired to keep sucking cock? Will your pussy be too stretched out to let men keep fucking it? It’ll be tons of fun to find out. I can’t wait for you to feel like a real whore. Are you ready to become the sissy phone sex slut you were always meant to be?

Call 1 888 8 FREAKY and ask to talk to Lola to be transformed into your true sissy self!

AIM: Lust4Lola