cross dresser phone sex Archives - Page 2 of 3

Cross Dressing Fantasies with Courtney

October 15, 2023 by femdom

Rather ticked off was suppose to go pick up my boyfriend but with the weather being so up and down they opted to stay working till the rains came next week. So that means I am here enjoying some naughty phone sex calls with you guys. Any one up for some sissy or cross dressing fantasies?

Also spend the day sorting out my closet. I am clearing out most the stuff in there and taking some of it to the consignment store. Every so often think its great to just clear out your closet so I can make room for new stuff. I can be a bit of a clothing whore. Think all girls and well sissies too.

When I was scoping out this new consignment store I swear a sissy had dropped off a stash of his play things there. For there were some straight up whore stuff. Tons of dresses for going out to the club or well sucking dick in. Then boots like omg I had no idea they would take boots that look like a stripper wore them. Hmmm maybe this is where the strippers and hookers drop off their stuff? Perhaps sissies need to go there and get their pretties on!

Like I said it was a new store that I was just checking out and I am use to carting off bags of clothes to my old store near my parent place but this place was so much fun. I know that I do taboo fantasies and nothing really surprises me on the phone but WOW walking into a place like that and seeing dirty things like that in my face. Ya you would be going holy shit someone ACTUALLY wore this! Not just talked about it or looked at it on a website but actually bought it and worked it. Did get me wondering how many loads of cum some of those dresses saw.

Ok so that is a completely random thought but like you wouldnt wonder yourself.

So I am around for some sissy phone sex and cross dressing fantasies. Give me a call who knows maybe we can talk about some of the cock raising outfits I saw at that consignment store.

Just ask for Courtney

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Sissy Bimbo Phone Sex with Dru

June 15, 2023 by femdom

You’re already a sissy. You threw out all your male clothing long ago. You’ve accepted that your tiny little clit belongs in a chastity cage for now and forever. You’ve grown your hair out and now keep it styled in a feminine way. You have more makeup than most department store counters.

But that’s not enough for you, is it? You want to go further.

Well, that’s just fine because as much as I like sissy boys and sissy girls, I like sissy bimbos even better.

It’s time for you to weed through your closet again. But this time, you won’t be throwing out your long-forgotten male clothes. You’ll be tossing out everything you own that’s not sissy bimbo material. You must look like the slut you are at all times, so no pants, no skirts longer than just an inch or two below your ass, no shoes with heels lower than four inches, etc.

And, yes, I know you already know how to do your own hair and makeup, but you’re going to have to learn a different way. You’ll be going full platinum-blonde, and you’ll be growing it out even longer than it already is. You’ll also be learning to slut up your makeup even more so than you already do.

Oh, and get ready for pink. Lots and lots of pink.

If you’re ready to begin your sissy bimbo phone sex training, then call me. Just remember that bimbos only speak when spoken to, so don’t let the thought cross your pretty little head that you will be allowed to say whatever you want to me.

Just ask for Dru

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Sissy Salon Fantasy with Porscha

May 15, 2023 by femdom

I was going through my wedding album the other day. Looking at my gorgeous wedding dress and veil. I loved everything around that day the hours of getting ready. Sitting in the salon getting the up do and my make up. The list really goes on and on. Perhaps its holding on to that special moment which makes it so much fun when I have a sissy who wants to do a salon fantasy.

Mind you this time I would really like to so a sissy salon phone sex fantasy where that sissy is getting ready for a wedding. Sitting in that chair with the hairdressing cape over them. The long blond wig being twisted on to big hot rollers. Have to build up that volume. Know the butterflies are fluttering around in your stomach over what your end result will be.

How will your hair turned out? Will it be like you planned?

As the last roller is being placed that is when the make up artist comes in to work her magic over your face. Opening her box of delightful colors that has your eyes just dancing in delight.

To feel the coolness of the foundation being applied. The casual conversation about what your wedding dress is like and what is going on with the reception. Things your all to excited to answer.

Far too excited about your dress.

So what do you think ready for a sissy salon fantasy and let me be your hairdresser and perhaps more.

Porscha

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Lingerie Loving Phone Sex Sissy

April 25, 2023 by femdom

So I know I do phone sex probably way too much when I start getting ideas for sissy boy assignments in the most craziest of places. Well maybe not that crazy considering the assignment I thought of. I saw this guy wandering the mall while I was working, folding panties of all things. He completely made me think of this one phone sex sissy boy that loves lingerie which is probably why we ended up talking. But anyways. I was watching this guy walk around the mall and I swear he had a thong on under his clothes like he was dying to pick out the ass floss but at the same time enjoying it a bit too much.

So I was like wouldnt it be fun to give the lingerie guy an assignment where he had to wear lingerie to the mall. Like panties, bra, stockings, garter belt, sexy cami under his jacket. Ya I didnt let him wear a shirt but was allowed pants. Then sent him to the mall and made him walk by the lingerie shops and think of me.

I havent heard back from him yet. So not sure if he did it or not. Or maybe he is still wandering the mall?

Have you ever done any crazy sissy phone sex assignments that got you really excited? Or maybe you want to do that one and send me pictures of you dressed up.

Oh and lingerie loving phone sex sissy you so need to call.

Kelly

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Sissy Adult Baby Phone Sex

April 15, 2023 by femdom

I adore sissy babies. Love putting them in those frilly dresses with the pretty ribbons and tons of lace. Those tights with the frills on the bottoms and the socks with the lace around the edges. I can go on and on with the joy dressed a sissy adult baby brings me.

Probably the only thing that exceeds that joy is publicly humiliating a sissy baby. For you dont expect me to be content will just having you prance around the house in that pretty girlie outfit do you? No of course not. I want to show off my little bundle of pink goodness to others. Now I know they are not all going to be as accepting as I am and they will be giggling and laughing at you. That is what its all about making your cheeks redden with embarrassment.

For those that love to be embarrassed when they are all dressed up in those pink diapers. Nothing quite like a 2 girl phone sex call where I get to tell the other girl how you are all dressed up and listen to her laugh and laugh at you.

I did just that with one particular taboo phone sex babe on the site, Emma she has the cutest giggle and she loves humiliating sissy adult babies as much as I do.

I know Emma and I would love to team up and dress up another sissy adult baby role play again.

Give us a call for a 2 girl phone call just ask for Nancy and Emma.

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Sissy Boy, Strap ons and Ass Fucking Fantasies.

February 25, 2023 by femdom

How to get a phone sex sissy boy rather excited all one needs to do is mention how big their strapon cock is!

Always laugh at you pretty sissy boys for the moment I mention I have a thick strap on cock your instantly asking how big is it? When was the last time you used it? Then that gulp of are you in the mood to use it now?

Well it would be a shame not to fuck your pretty sissy ass now wouldn’t it?

I mean after you have gone to all this trouble of getting dressed up for your hot cougar. Hear what you put on for me did get me looking over at my bedside table and thinking “Hmmm wouldn’t it be nice to break out my cock and give it to you?”

Yes I should be fucking your sissy boy ass with my thick purple jelly dick. Oh I know your a touch disappointed its not one of those realistic looking cocks. So am I but just think of this as a magical unicorn dick that will be transporting you off into the land of cock hungry sissy whores. One fuck with my strap on cock and you will be begging to always have something shoved up your ass!

Rather admit I do enjoy using the jelly variety of strap on for I tend to be a touch more aggressive when ass fucking and well this style will protect your sissy bottom from getting too sore and tender. After all getting fucked by myself is sort of that middle ground between fantasy and well the real thing.

Not that I have anything against putting a bit of punishment on your pucker hole but I dont want to turn you off that full feeling.

Now that I have you rather intrigued about being my phone sex sissy boy you can reach me by calling the number below. Just ask for Jillian.

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Cross Dressing Phone Sex Confessions with Arianna

January 25, 2023 by femdom

This is a question to the cross dressers out there. What was the very first item of ladies clothing you bought?

Or maybe you didnt even buy it. Have heard during various cross dressing phone sex calls that most men grabbed some item of clothing from someone they knew. It was a moment of opportunity that lead to them dressing up. It wasnt even a full dress up just something simple that lead them into temptation.

Think for one guy it was panty hose.

It started when he was away at college living off campus and sharing an apartment with a few acquaintances. Gone into the bathroom and the laundry basket was over flowing with one of the female room mates items she had planned to hand wash. As he sat going to the washroom he was staring at her bras drip drying over the shower rod and the basket of panties and panty hose.

As he washed up. His eyes kept darting to the basket and a nude pair of nylons that draped over the white plastic basket.

They were taunting him.

Teasing him.

Before he knew it he was snatching them on his way out. Tucking them in his pajama bottoms and making the great escape to his room.

First he stared at them all embarrassed at what he did and was about to walk out to return them but his room mate was back in the bathroom doing her delicate wash. He was doomed no way he could just causally return them now. Oh sorry these leaped into my hands! Sure that was a valid excuse.

The more he handled the silky nylon the more he wanted to try them on.

To feel that silkiness against his legs. It was so wrong but suddenly it seemed so right.

I could really continue on and on with this cross dressers phone sex confession around his first time dressing up but I think thats enough for now. How about you call and share your first time dressing up in women’s clothing with me.

Just ask for Arianna.

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Cross Dressing Phone Sex with Raine

November 30, 2022 by femdom

Yesterday I was walking the down town area. Just window shopping and enjoying the sun before the anticipated storms the weatherman was calling for. As I was staring in the window of some kitchen shop the reflection of a passerby caught my eye.

This amazonian type woman with rather masculine features. Gotta say at first I thought it was the reflections distorting the image like a fun house mirror. Making things seem opposite to what they were. When I turned around I half expected some petite woman standing behind me.

Nope the reflection was rather correct for it was a very tall man dressed up in ladies clothes out doing their afternoon shopping. The cross dresser just gave me the once over and proceeded down the sidewalk letting her black 4 inch heels click confidently on the brick.

Now I have to say most my interactions with men dressed up in ladies clothing has been via cross dressing phone sex calls. Well thats being full blow from the make up to the shoes dressed up. I have engaged with men who wear some item of ladies clothing like a panty boy or something who enjoys stockings. Garments that they could hide away under their “traditional” clothes so no one would find out their secret.

Which is all well and good. Rather interesting really. Nothing like playing footsie with a guy and discovering his foot is encased with silky stockings. Not sure who had a more befuddled look on their face to be honest.

Anyways I am totally back tracking with that rather limited interaction it got me wondering if cross dressing phone sex was where men who enjoy ladies clothing get their start towards public interaction?

Sort of that test the waters out with how girls on the phone interact with them and then poof venture out into the real world. Love to hear what your opinion is on that. Inquiring minds need to know.

Maybe I am over thinking the process. Either way I think this weekend should be all about some cross dressing phone sex be it humiliation or just what you should wear for a holiday party.

Raine is the name and the number is down below 😉

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Crossdresser Phone Sex with Courtney

October 30, 2022 by femdom

Its the day before Halloween and wouldnt you know it last night I get some guy calling me up who is prancing around in his “Halloween costume”. Well actually that is what he is telling his friends but really he loves dressing up in womens clothing so when Halloween comes around its the one day he can actually dress up in some pretty womens costume and everyone will comment how pretty he looks rather than give him those weird looks cause he is a crossdresser phone sex freak.

He has a few costumes to choose from one was the school girl, which had me laughing at. There is a plaid skirt, white button up shirt, white knee high socks, mary jane shoes and if that wasnt enough he got a wig that he could put into some pig tails. I want him to wear that one. The other one was more a stripper attire, which ya that would turn some head too. Short black pleather skirt, fish net stockings, red skin tight tank top and fish net style arm gloves, knee high boots and he was going to wear his red fuck me wig.

Either way he was going to be heading down to the MAC store and having them do his make up for the Halloween party. I so want to see some pictures of how he turns out. Think either costume will look hot as hell and get people to turn their heads. He is 6’2 after all without any heels.

Have a great night Mr CrossDresser hope everyone loves your “costume”

Just ask for Courtney if you too have a crossdresser phone sex fantasy or wanna discuss your Halloween costumes past/present or future.

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Forced Feminization Hypnosis

August 25, 2022 by femdom

Had an interesting feminization phone sex call but it was intertwined with quite a few other fetishes. The guy was looking for some age regression hypnosis where he is taken down to an age where he is living at home and then his mom forces him into women’s clothing.

I was definitely game.

So after weaving my erotic hypnotic trance on him and regressing him to a point where he was living at home again. It was all about focusing the fantasy on him exploring that empty house and ending up in his moms closet and noticing a very pretty pink dress. He was oddly fascinated by it but couldnt quite figure out why. His fingers touching it and enjoying the satiny feel of the material and how soft it was against his fingers.

It was as he was lost in his senses that he never did notice his mom standing behind him at the door way to the walk in closet. The smile on her face as she saw her boy so engrossed in that pretty pink dress. How he nearly jumped 5ft when her fingers touched his shoulder and pulled him out of his trance.

Sure he tried to explain his way out of the closet but his mom would have none of it. She just looked at him and smiled as she directed him to the bed. Sit down sweetie. At first she was loving but the more he fought to be released the more forceful she became. Pushing him on to her king size bed. Telling him that he was to strip while she wandered into the closet to grab that pink satin dress.

Upon returning her boy is near naked only wearing his boxers and looking at her like he wont wear that dress. But really he has no choice. That dress will adorn his body.

The more he argues the more mom just smiles and laughs. For she welcomes having to force him into a dress. With that she is tossing the pink dress on over his head and starts getting him to twirl around and around while she laughs at him.

Mom did always want a girl and a sissy boy is just as good as any when you get down to it. His discomfort only makes the moment even more exciting. For really mom is just deciding what else she can force her sissy boy into.

Book an erotic hypnosis phone sex with Savannah.

Remember to book a minimum of 30 minutes for your hypno call.

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