crossdressing phone sex Archives - Phone Sex : Live Fetish Phone Sex

Crossdressing Phone Sex with Dottie

January 12, 2026 by kittenranch

Crossdressing phone sex is one of my favorite things to enjoy with you. Of course, it’s not for everyone, but if you like to get all dolled up and feminized, we should absolutely spend some time together. Admittedly, I’m an older gal, but that just means I have plenty of experience. That’s right; I’ve been taking you fellas into my closet for a makeover for many, many years. In fact, it’s been something I’ve enjoyed since long before it was as trendy and acceptable as it might be today. Yes, I know, it’s still a secret pleasure for many of you and that’s completely fine. We’ll have our special time and no one has to know about it. Well, unless we want someone to. Maybe a special friend might join us to see how pretty and sexy you look. You can try out all your girlish charms on him and see what happens. Oh, my, wouldn’t that be so much fun?!

More about my closet. It’s really pretty amazing for a crossdresser. If you enjoy crossdressing phone sex, you are going to be absolutely smitten with all the treasures awaiting you. Sexy lingerie, thigh highs, pantyhose, slips, skirts, dresses, heels, panties, thongs — really everything you dream about. We can pick out something together, or I can wait just outside while you put something together and give me a fashion show. I will tell you, I have several drawers full of panties, all cuts, colors and styles. In so many beautiful colors. Many have matching bras, and we can even work out some boobs for you. So yes, come on over and let’s spend some time getting you just right. After that, we can do whatever strikes your fancy. Invite a man or two to play, go to a club and show you off, or have some of my girlfriends come over. These are just some ideas, but we’ll come up with something perfect just for you!

Call 1-888-662-6482 Now! Be Sure To Ask For Hottie Dottie!

Crossdressing Phone Sex with Dottie

January 2, 2026 by kittenranch

Call 1-888-662-6482 Now! Be Sure To Ask For Hottie Dottie!

Cross Dressing Phone Sex with Gretchen

May 2, 2024 by kittenranch

I love turning a weak little man into a beautiful sissy. Cross dressing phone sex is something near and dear to my heart. I love the idea of taking advantage of a weak and pathetic man. Making him submit to me in ways he never thought possible. Making him whimper and beg on the phone to me like a needy little bitch. Just imagine if you were there trying to fuck me, and before you knew it… the tables were turned. I’d love to take some seemingly strong man and just shove the dildo to my fucking machine so far into him he’s begging me to stop. Turning him into a pathetic drooling mess of man meat, right before my eyes.

Just the thought of how good it would feel to fully cripple you mentally because your cock just exploded harder than it ever did before. You and I both know you need to give up some control.
Just imagine coming home from a hard day at your manly job and giving control over to me. You see, I’ve always had this massive fantasy of entering a sissy pageant, making you compete. Telling you to show me you deserve the role you want in my life. Making you the neediest little bitch you can be in the prettiest pink ruffly dress you’ve ever seen.

Do you have what it takes to be the best of the best? Let’s find out! call me now so we can roleplay our cross dressing phone sex fantasy and turn you into my little sissy whore. I can’t wait to cum together my little sissy faggot. Just get on the phone and give me a call for cross dressing phone sex at 1 888 662 6482 – ask for Gretchen.

Email me at Taboogretchen@gmail.com
Follow me on Twitter @taboogretchen
Follow me on Bluesky @taboogretchen.bsky.social

Slutty Phone Sex Sissy with Whisper

October 29, 2018 by Whisper

So who all dressed up as a sexy what ever this weekend? Let your inner sissy out to play? Course those of you who had to work and werent allowed to play dont worry for I am here to help you out with a little slutty phone sex sissy play.

Yes I did say slutty sissy play.

We both know that your inner phone sex sissy is nothing more than a cum craving whore that wishes to dress like a tramp and go out and suck as much cock as humanly possible. So let me help you out.

No. I am not gonna help you out in the sense of getting you dressed up. Well yes. I will ensure you look your slutty best but actually I am gonna make sure that while your in the process of dressing up all slutty your sucking back a few loads of cum from my shemale cock.

Now your get the idea!

See I want to make sure that before I unleash you into the streets that my slutty phone sex sissy is well prepared in actually being a cum whore. That your not gonna ruin your make up.

Actually scratch that its more that your not gonna gag on some scrumptious jizz filled cock. The ruined make up from being glazed all over does sound rather sexy if you ask me. Kind of adds to your slutty appearance so go on lets ruin your lipsticks and let the world know who exactly you are.

A cum craving slutty phone sex sissy bitch!

Now all you need to do to embrace your inner slut is call me ~ Whisper the hot tranny ready to give you a pearl necklace. 1-888-662-6482

Taboo Phone Sex Girl Courtney

February 20, 2018February 20, 2018 by Courtney

Have to say you guys are beyond kinky and keeping this taboo phone sex girl extremely busy. Which makes for one hell of an introduction into the world of kinky fetishes.

If we havent had the pleasure of talking yet my name is Courtney. Girl with really no limits and a love for all things kinky and perverted. Which makes for some very interesting times together.

Kind of sitting here wishing I could share some of the taboo phone sex role plays that have gotten my panties rather wet over the last month… But some people are just not as open minded as others so out of respect for them I shall just keep the naughty transactions between my lips and well not sure where else to be honest.

My boyfriend was home last week so I got my fill of fun with him and now he is gone again which means back to the kinky fun on the phone. From those looking for a sexy side kick to help out with a certain type of scene to well dressing you up and making your ass super pretty.

What do you say?

How about calling and sharing with me your taboo phone sex fantasies. Sure there is something extra naughty that gets your cock throbbing. Cream filled pussy perhaps or are you more the dive your tongue into a hot ass kind of guy?

My number is 1-888-662-6482 tell the dispatcher you wish to speak with Courtney and she will handle all the details.

So looking forward to talking. Have on my favorite pink panties today!

Cross Dressing Phone Sex with Gretchen

July 20, 2017 by kittenranch

I love talking to cross dressers! I love comparing notes on trendy makeup tips and where to find the best deals on clothes, and it’s amazing learning all the ways they make themselves look so feminine and pretty. When a guy calls for cross dressing phone sex, it’s like talking to one of your best girlfriends! I love hearing about their preferences for fabrics and colors – do they prefer silky panties or lacy ones? Red? Pink? And I always ask what color their toes are painted. A lot of times a cross dresser will keep his toes painted so he can always feel pretty, even at work, since his shoes cover up his dirty little secret. Yes, by the end of a cross dressing phone sex conversation, we’re like the best of friends, doing exactly what best girl friends do – sharing all our darkest secrets with each other!

Mmmm, those are definitely not all makeup tips being shared. Once those big boys turn into gorgeous gurls, they love to go out and get into trouble, and afterwards they dial the phone for some cross dressing phone sex with Gretchen, and they confess all the dirty deeds they did while wearing sexy lingerie. I love hearing about all the men they get to play with, all the blowjobs they gave and all the times they let a man fuck them because those men were so turned on by the idea of being with a beautiful woman who also has a cock! These gorgeous gurls get more dick than a lot of women, sometimes several dicks at one time! They know they’ve got just what a lot of men want, and they have learned exactly how to use it, and Miss Gretchen just loves hearing about every sordid detail. So cum on gurls, call Gretchen for some hot cross dressing phone sex and let’s share all of our naughtiest stories with each other!

Call 1 888 662 6482 and ask for Gretchen for cross dressing phone sex!

AIM: MILF_Gretchen
Twitter: @MILFGretchen
Tumblr: milfgretchen

Sissy Boy Phone Sex with Simone

June 19, 2017 by Simone

Put on your panties, pick up your phone, and call me for sissy boy phone sex. Don’t stop with just panties either. I have silky stockings for you with a sexy garter belt to frame your sissy ass so pretty. We aren’t going to stop there either. I think a sexy bra stuffed with titties or a soft camisole that will rub your sensitive nips all day will only add to the look and that sissy boy feeling. Add a pair of 5″ heeled cum fuck me pumps and bright red shiny lipstick to really make you feel like the sissy slut you are.

Now that you are all dressed up with no place to go, it’s time to talk about your life as a sissy boy. We both know that no real woman would ever want to be with a sissy like; at least not in the traditional sense. Your dick is too small to please me and you’re wearing panties! I’m even willing to bet that you already have a wet spot in your panties just thinking about all of this. Get on your knees and crawl right between my voluptuous thighs. I’m going to rub your sissy face all over my wet panty pussy. Not only will you look like a sissy boy, you are going to smell like a pussy boy too.

Happy you called for sissy boy phone sex today because I’m having some friends over and it’s going to be your coming out party. My girlfriends and their boyfriends will watch as you shake your little sissy ass for them. When I get out my strap-on and demonstrate your cock sucking ability for them, a couple of the guys decide you need to practice on the real thing. Yes, you read that right, as part of being my sissy boy, you’re going to learn how to be the best cocksucker there is. Might as well make the guys happy since you’re too sissy for the girls.

For sissy boy phone sex, call Simone, 1-888-662-6482

aim – sensualbbwsimone

Panty Boy Phone Sex Humiliation with Rachelle

January 23, 2017 by CoedRachelle

Are you wondering if your a panty boy or just a guy with a fetish for women’s panties? I know whats the difference right? Or better yet how can a hot coed phone sex girl like me help you out with your confusion around being a panty boy.

Dont let my age fool you. See I work at a lingerie store and see lots of guys come in to buy panties. Some times those guys end up chatting me up and spilling those kinky little secrets as to who those panties are for.

At first I was completely disgusted guys would tell me what they were gonna be doing with those panties. Then it became exciting to know that those panty boys could end up chatting to a coed phone sex girl like me by the end of the day.

See over time the panty boys and guys with a fetish for panties simply told me the difference now I use that little bit of knowledge to giggle at you guys when I am on the phone with you.

Ok fine thats probably wrong but not like you guys are complaining about the humiliation you get from me. Least I couldnt hear the complaints over the moaning during the last panty boy phone sex call I did.

I know I look super sweet but I do have a bit of a bite to me too. My giggle with have you begging for me to make fun of you in your panties or what ever it is your doing with those panties.

1-888-662-6482 ask for Rachelle the hot coed phone sex girl ready to humiliate you.

Taboo Cuckold Phone Sex with Simone

November 14, 2016 by Simone

Aren’t you the naughty boy who not only wants to be a cuckold, but engage in some very kinky taboo cuckold phone sex with me. I have seen you peeking in my bedroom late at night when you’re supposed to be in bed. You stand in the doorway peeking through the crack watching me on my hands and knees getting pounded by my BBC lover. I know you put your hands inside your pants to touch yourself while you watch my lover’s huge cock fucking my pretty taboo pussy.

I see how you look at me, adoringly at my big tits and my fat round ass. If you are like most boys you are thinking about what it would be like to fuck this hot MILF just like her lover does. There is only one problem here baby, my lover needs to have a huge cock to satisfy me and you are just a little dicked sissy.

That’s right, I said a sissy. Now that we both know the truth, some things are going to change around here. I am going to put you in pretty sissy panties from now on and I’m going to teach you what it means to be my cuckold boy. I might tie you to a chair with your hands pulled back – no touching that little dick without my permission – as I teach you to be my fluffer and make my big black lover’s cock all hard for me. You will learn to love my sweet cream pie and be my clean up boy. You will be my taboo phone sex cuckold and I will be your sexy MILF Cuckoldress.

Your lessons won’t even stop there. When you open your closet and see your boy clothes gone and replaced with sissy dresses and more, there’s no doubt what my intentions are. When I say taboo cuckold phone sex, I mean it. Call 1-888-662-6482 and ask for Simone. You know you want to hear more!

aim – SensualBBWSimone

cross dressing phone sex with arizona

March 11, 2016March 9, 2016 by pssblogs

Hey, boo! It’s your boss ass bitch, Arizona! I understand that some of you are into cross dressing phone sex! Some girls think that means you wanna get down on your knees and suck a dick, but I know that’s not the case. I mean, maybe sometimes it is, but cross dressing doesn’t necessarily mean that you totally want to be turned into a sissy slut. So when you call me, boo, we will just be focusing on getting you all dressed up. It’s so much fun and I can’t wait to get my hands on you.

Is cross dressing phone sex something you’ve been doing for a while, or have you just been thinking about it and have never pulled the trigger? Well, you’re going to have so much fun getting all dressed up with me! If you don’t already have a sexy outfit, we can just talk about it on our first call. But you have to promise me that you’re gonna go online or go down to the mall after we talk and pick out something sexy to wear for our next conversation, boo.

What do you think you’d look good in? Maybe you can tell me what you look like and I can tell you what colors you’d look best in. And if not, there’s always black. Maybe we can start with some sexy black lingerie – a bra, panties, stockings. Then when you’re comfortable with that and you like how you look, we can move on to shoes, beauty/hair and clothing. Oh, this is going to be so much fun!

I know you are ready to pick up your phone now and call me for some hot cross dressing phone sex. I can’t wait to talk to you. Dial 1 888 662 6482 and ask to talk to Arizona