Category: Cross Dressing Phone Sex

Fetish Phone Sex

By , January 13, 2012

 

GG was a little CBT and pain fetish phone sex slut for me and it was so hot! He was dressed up in a wig, make up, pantyhose and I pulled out my riding crop and fly swatter for a little CBT punishment on my cross dressing perv. It was awesome, beating his cock and balls, and then calling my little niece in to join us for a little age play fantasy too. She fisted his naughty, pervy ass while I beat him in our awesome cross dressing and CBT play time. It was so fun!

I had an amazing cross dressing feminization fantasy with CH. He’s a girly-guy and likes the soft side of feminization and dressed up so pretty for me. He made our pantyhose fetish phone sex playtime really hot and sexy. We did each other’s hair and make up, mani-pedi too, and picked out a pretty lacy outfit for each other. We were ready for a night of cock sucking and we had a blast. I can’t wait for more!

We can do anything you want on our fetish phone sex playtime and be as sensual, kinky or naughty as you want. I have no limits at all with our age play fantasies too, so we can do it all together. Tell me your favorite fetishes I have many fetishes too so I’m sure we have lots in common, and cum with me. 

Buy my  nude pics here at our new store.
 
Jenni   1-877-340-7498

Crossdressing Phone Sex

By , January 6, 2012

Will you be my crossdressing phone sex slut and put on those panties of mine? I know you love to sniff and rub those silky panties all over your clitty cock and it makes you so horny to slide them on, especially when they are dirty panties from the hamper. Are you a slutty panty boy who needs to be feminized by a beautiful woman like me? You are going to look so sweet dressed like a bitch for me, bent over, your eyes wide at the sight of my big strapon. I’m going to fuck your crossdressing phone sex cunt hole so hard you are going to scream for me, beg me for more, harder, deeper.

Maybe for our crossdressing phone sex call you can really put on a pair of panties or heels for me before you call. Have fun with it and I’ll get you off hard!

Karyn
1-866-371-5413

Buy my naked photos

Sissy Phone Sex

By , November 23, 2011

What are your naughty fantasies that you think of when you are all alone? Do you have sissy phone sex curiosities that you would love to indulge in with a beautiful open-minded woman like me? You don’t have to be shy or hold back, when you call me you can tell me exactly what you want and need. Do you get hard from the idea of wearing panties or stockings? Do you need a Mommy to humiliate you for being a silky panty wearing cock sucking fag? Do you dream of being completely transformed into a crossdresser and taken out for a night on the town to see how many heads you can turn?

Whatever your needs a sissy phone sex session with me is sure to provide you with exactly what you want. Anything goes with me and I am hear to listen to every little detail without judgement and in fact, I will probably enjoy every single second of it! I love playing with sissy phone sex sluts and I look forward to playing with you too. Until then, kisses!

From Nov.23-Nov.25 at 11:59 pm, purchase a 15 minute call and ask for the stuffing special and I’ll give you 5 minutes extra FREE!

Karyn

1-866-371-5413

Crossdressing Phone Sex

By , November 15, 2011

You’ve always wanted a girlfriend to explore your crossdressing phone sex desires haven’t you? A woman like me who knows what it takes to look sexy and feel feminine. Wouldn’t it be so fun for you to come over for the night on our call and have a look through my closet and dresser drawers for the sexiest, sluttiest, prettiest things to wear? I will let you try on anything you like and then when you are feeling so hot we can be lesbian lovers together and touch each other all over. I’d love to give you breast forms to put in your bra and rub our clitty’s together as we giggle and kiss, sucking on each other’s tongues. Crossdressing phone sex with me doesn’t always have to be about cocks and men, sometimes girls just want to be naughty together!

I look forward to our crossdressing phone sex date together. I just know we are going to be the best of friends and have so much fun!

Karyn

1-866-371-5413

Cross Dressing Phone Sex

By , October 29, 2011

Do you like cross dressing phone sex with a hot and open horny girl? Then put on your best dress (or your wife’s best dress) can call me so we can explore together in a hot and kinky cross dressing phone sex session. We can explore and experiment in any way you want. Do you want me to be the curious girlfriend who sticks her hand up your skirt to slip a finger in your ass? Or maybe I make you wear my bra and panties, and then rape you with my strap on. Whatever your fantasy is, call me because I want to act it out with you. Call me for cross dressing phone sex !!

Karyn

1-866-371-5413

Cross Dressing Phone Sex

By , September 30, 2011

If you like cross dressing phone sex then you’ll feel right at home with me. I love a guy who can get in touch with his “other” side and isn’t afraid to dress in feminine clothes. I’d love it if you’d put on your best girlie clothes for me, and let me touch you and caress you, and fuck you when you’re dressed all pretty! So put your best girl clothes on, and call me so we can have a hot cross dressing phone sex session together. Call me for cross dressing phone sex now!

Karyn

1-866-371-5413

Cross Dressing Phone Sex

By , August 26, 2011

What is your cross dressing phone sex fantasy? Do you like the idea of dressing up in your girl’s panties and bra and dresses? Do you want to wear my girlie clothes and let me do your hair and makeup, right before I fuck your brains out? I love a man who isn’t afraid to explore his “other” sides… so if that’s you, and you like cross dressing phone sex, then call me and let’s explore all your hot cross dressing phone sex fantasies together, today!!!

Karyn

1-866-371-5413

Sissy Phone Sex

By , July 8, 2011

Are you setting there in your big girl panties looking my photo and ready for your sissy phone sex session?  Then quit stalling and pick up that phone so we can begin our sissy play.  I have on my make up, straightner, bra and panty sets and my fuck me shoes and all ready to dress you up.

 

Or maybe this side of you is new to you and just starting to surface.  That’s fine, you can still call me for sissy phone sex training.  I offer training in cross-dressing, feminization and strap-on play for those that are really adventurous and ready to explore.  I will even laugh at you and humiliate you if you have a small dick.  And please do NOT try and tell me 4 inches is average.  Whatever….as I laugh at your pathetic self.

 

So as you can see I offer you sissy phone sex training in small steps or leaps and bounds.  But in order for us to begin you need to pick up that phone and dial my number.  So quit stalling, you know this is what you want.

 

Dusty 1-866-524-3105

Cross Dressing Phone Sex

By , June 29, 2011

If you’re into cross dressing phone sex then call me and tell me all about your cross dressing fantasies. I can dress you up as a pretty girl and we can explore the boundaries (or lack thereof) of our sexuality together. Whatever your cross dressing phone sex fantasy may be, I would love to explore it with you if you will just call me. Call me for cross dressing phone sex now!

Karyn

1-866-371-5413

Cross Dressing Phone Sex

By , May 5, 2011

Cross dressing phone sex is one of my very favorite types of phone sex calls.  I love it when I get a phone sex sissy or panty boy on the phone and he wants to explore all of his feminization phone sex desires.  Sometimes it’s a caller who has always fantasized about being caught by his phone sex Mommy playing in her panties and the call takes a turn into forced feminization play as Mommy insists that he dress up completely and become Mommy’s little girl.

I had a call like that the other day.  My caller is a mature phone sex caller about my own age and he started playing in his Mommy’s panties when he was just a preteen boy, not even able to cum yet, but loving the feel and smell of Mommy’s used panties.  When I caught him, at first I was angry at the way he had invaded my privacy, but pretty soon I was turned on at the idea of making him my little girl.  By the time I had him dressed, you couldn’t tell that under that pretty little girl dress and make up, was a sissy phone sex boy!  Our call got kinky as Mommy donned my strap on, and soon my boyfriend showed up and wanted a piece of the action.  Just imagine my sissy phone sex slut now sucking cock and getting ready to be fucked in his male pussy for the first time!  It was steamy hot for sure.

Another of my favorite sissy phone sex playmates emailed me and told me just what was on his mind and when he called, I was ready for him.  I dressed him in two pair of his favorite specialty made nylon panties, a garter belt and stockings and a nylon slip.  I inserted a vibrating butt plug in his virgin hole and then began to whisper naughty things in my sissy’s ear as I encouraged him to suck on my strap on dildo.  He gets off on humiliation phone sex and I have to say, I love humiliating him as I remind him that he’s not a man, no real man would dress like he does and he’s not a woman either.  Just a pathetic dildo sucking sissy who was about to be penetrated and fucked like a girl! 

No matter what your cross dressing phone sex needs or fantasies may be, give me a call.  I’ve got lots and lots of experience with guys who love to dress, from panty boys to full on cross dressing phone sex playmates who love to go out in public dressed as a woman.  Find out how much difference experience makes when you talk to me, a woman who’s spent much time with guys like you in person and on the phone.

Sylvia @ 1-877-264-4931

www.PhoneSexTherapySessions.com

Sissy Phone Sex

By , March 8, 2011

How about some kinky sissy phone sex with a heavy dose of humiliation phone sex thrown in for good measure?  That’s what one of my favorite panty boy phone sex callers loves!  Yesterday he sent me some new pictures of himself all sissified in pretty pink panties with ruffles and lace, and a pretty bow in front.  One of them even showed him in a see through half slip and I just had to laugh at my cross dressing phone sex sissy slut!

He told me about how he has been keeping himself on the edge of orgasm for hours and how excited that makes him, and he was loving the feeling of being so aroused for long periods of time, denying himself that final release until he could no longer stand it.  He knows I love tease and denial phone sex, and humiliation phone sex is also a major turn on for me.  I have a nasty sense of humor and a wicked mean streak that makes his sissy clitty hard as a rock, and I love making fun of him in his panties, telling him how he’s not really a man, and not a woman either.  Just a panty wearing sissy who needs to learn to cum like a sissy.

We fantasized about adding an underage phone sex girl to the mix, her being my dominant apprentice in training and how she’d laugh and make fun of him.  Nothing gets him more excited than being exposed to my friends for the cross dressing sissy he is, and when you add a very young teen to the mix for some age play phone sex, he’s in panty boy heaven.  I told him I’d train her to use him like the sissy he is, and even provide her with a big pink strap on phone sex dildo … pink being for sissies …. and he moaned in pleasure.

I’ve got lots of experience with all kinds of feminization phone sex lovers, and whether you’re a panty boy phone sex lover looking for a mature and experienced dominant woman who gets off on humiliation phone sex, or a feminization phone sex lover looking for a woman who understands your deep need for transformation, you can count on me to provide you with exactly the kind of feminization phone sex call you desire.

All your sissy phone sex fantasies are just a simple phone call away, so why wait any longer?  Pick up the phone and give me a call today.

Sylvia @ 1-877-264-4931

www.PhoneSexTherapySessions.com

Cross Dressing Phone Sex

By , February 26, 2011

If you want cross dressing phone sex then call me and let’s play! I can make you wear my panties for a while if you’d like. We’ll dress you up in my bra and panties and a nice tight little skirt. I’ll probably have to ass rape you before the night is over, so come ready for some action! It turns me on so much to see a guy who is willing to explore those “other” sides of himself. If you’re into cross dressing phone sex then let me be your cross dressing phone sex friend… I will do whatever you want and go wherever your fantasy takes us. Call me. I’m horny, and waiting!

 

Karyn

1-866-371-5413

Cross Dressing Phone Sex

By , February 4, 2011

Put your best dress on baby because it’s time for cross dressing phone sex with Karyn. Tell me all about how you like to dress up, and especially about what panties you’re wearing! Why? Because I want to rip them off right before I put on my strap on and fuck your tight ass hard! If you want to just be yourself in some cross dressing phone sex then call me and tell em what you’re wearing! I’m open to your sexual fantasy would, I just need you to tell me about it and bring me along for the ride! Call me for cross dressing phone sex tonight!

Karyn

1-866-371-5413

Cross Dressing Phone Sex

By , January 11, 2011

Mommy’s going to put her skirt on you and have her boyfriend fuck your tight little ass in some hot cross dressing phone sex today. I can’t wait to hear you whimper like a little girl while his big hard cock slams deep into your ass.

Let me shove your face into my spread legs in hot incest phone sex as my boyfriend relentlessly pumps your ass. Harder and faster, until finally he unloads so much cum in you that it hurts. That’s right… it’s too much! But keep your face down there or mommy’s going to get angry and have to spank you! Whatever perverted phone sex wishes you have can be made reality when you enter mommy’s wonderful world of kinky phone sex!

Karyn

1-866-371-5413

Sissy Phone Sex

By , December 29, 2010

I’m your mature phone sex play partner, Sylvia and Sissy Phone Sex has to be one of my very favorite kinds of phone sex play.  Last week was filled with calls from some of my very favorite cross dressing phone sex callers, and I wish I had the time and space to tell you all about each and every one of them.  But, since I don’t, let me just tell you about just one of my hot feminization phone sex calls.

One was from my Sissy Slut Suzanne, and we did a kinky humiliation phone sex call where she played a dancer in a chorus line type music festival for the holidays.  She was all dressed in a very scanty body suit, dipped low showing her cleavage, fishnets stockings and cum fuck me heels, all topped off with a little Santa’s helper hat.  I was the director and it came to my attention that Suzanne wasn’t a real girl at all, but a tranny, and I was totally pissed off.  I called her into my office, confronting her with the fact that I knew she danced in a female impersonator club and that she had lied on her application to me, checking off her sex as female! 

I made her strip out of that body suit and show me her pathetic little dick, or clit as she called it, and I discovered that she had no balls whatsoever.  A castrated sissy!  Not a man, not a woman ….. a THING!  You can be assured I humiliated this castrated sissy in every way imaginable and was extremely cruel in my verbal abuse, and then I called in a couple of the guards, both extremely well built and well hung young black studs.  I told them I wanted this pathetic castrated sissy taught a lesson she wouldn’t soon forget, and they raped her sissy ass pussy and her mouth as well.  You’d have thought she’d be screaming stop, but instead the little slut loved every minute! 

And so did I!  I love playing with all you hot crossdressing phone sex sluts, and whether you like to keep things to erotic conversations, or sensual domination phone sex scenarios, or like my sissy Suzanne sometimes like to get really nasty in a humiliation phone sex call, I’m always ready for you. 

Sylvia @ 1-877-264-4931

www.phonesextherapysessions.com

Faggot Phone Sex

By , December 13, 2010

Well, my cock sucking, cock kisser Kenny has finally owned up to the truth, he is a faggot phone sex slut!  LOL  He cannot help himself, he’s always been a gay boy, and his phone sex Mommy has always known the truth about him.  For a long time now he’s been hiding behind his cross dressing phone sex fantasies, dressing like a sissy phone sex whore, when in truth, he was always just a faggot. 

Dressing like a woman made him feel like it was the clothes that gave him the desire to be a cock sucking phone sex slut, but lately he’s finding himself looking at pictures of hard young boy cock online, and he doesn’t need to be in his sissy phone sex clothes to be aroused.  It’s all he can do to keep from cumming all over himself at just  the thought of a hot stiff young rod in his mouth, and of course, being the gay boy he is, he wants it up his faggot pussy as well!  Try as he might he cannot resist his urges, and lately when he calls he’s completely naked and hard imagining those young cocks spurting cum in his mouth and ass. 

I love when he calls because I always know I’m gonna get a good laugh as we engage in some hot humiliation phone sex and I make him admit to me that he’d rather have cock than pussy.  Even though he has a beautiful wife, he’d rather have a cock in his mouth and ass than be fucking her pussy.  He gets off on the idea of his wife and her lovers, and the thought of being allowed to clean that hot creampie out of his wife’s well fucked pussy drives him insane.  He’s definitely Mommy faggot phone sex slut, and that’s exactly how I treat him.  Laughing as I fuck him in a strap on phone sex session and he imagines Mommy watching him getting his faggot ass fucked.  He’s such a hungry homo that he eats his load after he shoots, another sign he’s definitely a queer!

If you’re looking for a domination phone sex session with a mature phone sex cougar who understands your deep need for humiliation and degradation, then pick up the phone and give me a call.  I love all types of faggot phone sex play, from sissy phone sex to forced feminization phone sex, to cock sucking and cum eating phone sex, and even forced bi fantasies.  Nothing is ever off limits or too taboo for us to explore.

Sylvia @ 1-877-264-4931

www.PhoneSexTherapySessions.com

Forced Feminization

By , November 9, 2010

I adore taking forced feminization phone sex calls. I love when some pathetic guy tells me about his secret love and shame for wearing womens panties.

The other day I had a call from my usual sissy panty boy, “Jane” as I call him. I told him that we were going to have a little fun at his expense.

He was already moaning, ready for me to really humiliate him. He became swept up in our cross dressing phone sex where I made him put on the sluttiest little plaid skirt, red bra, and a white shirt. Oh it didn’t stop there! I wanted his whore lips covered in lipstick. I wanted him to look like the dirty little tramp I knew he was.

The call continued with me forcing him to suck the dick of his teacher. I wanted Jane to see what it was like to fuck and suck for a good grade on his exam. The pathetic shit ate it up! It had to be one of the best and twisted takes on schoolgirl phone sex.

Erica

1-877-851-0229

Feminization Phone Sex

By , October 2, 2010

My what a fun feminizaion phone sex call I had last night with JP. I love to dress up and go out and have fun. He wanted to be just like me. He wanted me to dress him up in something very sexy and very slutty and take him out on the town and find some hot men. Oh I explained just how slutty his outfit was I was making him wear, the make up, the fuck me pumps I made him put on. Then how he was looking just like a hot slut and the fellas in the club were groping his tight ass and tits as soon as we walked in. “Janelle” his new name became the hot slut with the hot pussy for the men.  I so glad he called and we had so much fun together.

 Does a feminization phone sex fantasy turn you on? Then give me a call.  You can become my sissy boy slut and we can have lots of fun together, getting ready to go out on the town and see what men we can find. Or perhaps you have a cross dressing phone sex fantasy, we can do that too. And yes there is a difference for some. For some fellas they just want to dress like a hot female but for others they want to go all the way. Dress up and go be a little hot slut bitch with all the men.

So whatever your phone sex fantasy is give me a call and we can have some fu.

Dusty 1-866-524-3105

Sissy Phone Sex

By , September 27, 2010

Lately I’ve been having a lot of hot fun with my new sissy phone sex slut, Jezebel.  You can tell from this cross dressing phone sex sissy’s name, she’s not one of those “pretty in pink” girls who like pink satin lace and ribbons, and being sweet and girlie.  No, from our first feminization phone sex conversation, I knew Jezebel was more of the whorish cock sucking, cum eating phone sex type. 

During our last hot sissy phone sex encounter, Jezebel was dressed in her favorite colors, black and red, even with red jewels …. I’m thinking those are truly her signature colors and with her cock sucking red lipstick, sexy thongs that tease her sissy pussy and joan jett wig, she is one hot sissy slut indeed. 

One of the things I know that Jezzy and I have in common, is a love of big black cock.  She loves slurping on her big black dildo, imagining I’m there as her phone sex Mistress directing her to suck that huge black dick and she does so with such vigor, you can tell how much she loves it.  But that’s just the beginning, my sissy whore loves taking that big black cock in her hot sissy cunt, and when it’s time, she obediently spreads her legs, or bends over and exposes that waiting fuck hole.  She wiggles and squirms and dances on that big dick, until he finally explodes deep inside her pussy making her clitty squirt too!

Playing with my newest submissive phone sex sissy is so much fun.  I love being her phone sex Mistress, and I have lots of ideas and plans for my cock sucking whore.  If you love sissy phone sex as much as Jezebel, and are looking for a woman who is mature, experienced and has first hand knowledge from years of real life association with crossdressing lovers, give me a call.  I’d love to get to know you particular crossdressing phone sex fantasies, from the pretty in pink satin sissies, to the pole dancing whores like my sissies Jezebel and Susanne …. I’m here for you.

Sylvia @ 1-877-264-4931

www.PhoneSexTherapySessions.com

 

Cross Dressing Phone Sex

By , September 23, 2010

I just love sissy boys! I want to help you, give me a call and we will experiment with your wardrobe with a bit of cross dressing phone sex. After we get you all dressed up, nice, soft panties stretched across your little cock, you can watch me as I suck on daddy’s cock, I want to watch the wet patch spread across the front of those panties. I will give you guided masturbation phone sex. Letting you stroke your cock through the soft material. You know panty boy phone sex always makes you jerk uncontrollably in an orgasm. What are you waiting for? I’ve got just the set of panties for you….

Karyn

1-866-371-5413