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

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

Fetish Phone Sex with Cassie

Are you kinky? Maybe a little twisted? Well, I am definitely a whole lot of both! I love to experiment with different fetishes and would love to do it with you in some hot fetish phone sex. Do you have a foot fetish and want a pair of sex hose covered feet with beautifully painted red toenails to lick and suck? Or maybe you want to tell me all about your favorite bras and panties and stockings and garters that you like to wear under your clothes to the office. Maybe you are an exhibitionist and love to have sex in public places in the hopes of being watched? Or is there a hot girl next door that makes you play the voyeur as you watch her underdress and rub her clit through her bedroom window. I also love men with an ass fetish that want sniff and lick my pink bung hole. Just the thought of you burying your face or your cock between my sweet ass cheeks sets my juices to flowing! Fetish phone sex gets me so hot!

fetish phone sex

Thinking about you living out your fetish fantasy with me on the phone gets me so excited and makes my pussy soaking wet. I would love to slip into my favorite black stockings with the lacy tops that are clipped to some ultra-sexy black and red garters. Then slid my sexy feet into some black patent leather stiletto heels and nudge to toe into our balls and play with your cock. Then I could take them off and you could try them on! No fetish is too wild for this girl! I love fetishes of all kinds and need you to call me so I can fantasize about them with you in some hot fetish phone sex.

For fetish phone sex call 1 888 8 FREAKY and ask for Cassie.

AIM: PiercedCassie

Small Penis Humiliation Phone Sex with Samantha

I seriously love it when a loser calls me for small penis humiliation phone sex. I usually never know what I am going to do with a guy until he calls, but right now, all I want is for a guy with a micro dick to call me so I can put him into a pair of panties and show him off to all of my sexy girlfriends. Doesn’t that sound good to you? I know you love showing off your tiny cock for some reason. I really don’t get it. It’s nothing at all to be proud of. But I guess maybe you’re fucked up enough to be turned on by being humiliated. So yeah. I can give you that. So can my pretty girlfriends.

small penis humiliation phone sex

You know, I think what would be tons of fun is to have a sex toy party and you can be the entertainment/waiter/server and bring us snacks and drinks while we look at the toys. And if I tell you to dance or wiggle or sing for us, you will do it. We all need a good laugh sometimes. And you can also the sex toy tester. I mean, we’re going to need to see how things work. You can use your pussy to show us how everything works. I think that sounds like a really fucking great idea, don’t you? And maybe if you’re a really good sissy slut, I will even let you cum in your panties right there in front of all of us girls while you fuck your pussy.

Aren’t you just super duper excited for your fun small penis humiliation phone sex call? Get your panties on and tuck your itty bitty dickie inside them and then give me a call. My number is 1 888 8 FREAKY and my name is Samantha.

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.

sissy training phone sex

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.

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!

sissy phone sex
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.

sissy phone sex

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

Fetish Phone Sex : Anything Goes Phone Sex