Cross Dressing Phone Sex Confessions with Arianna

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.

cross dressing phone sex

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

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.

crossdressing phone sex

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

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.

crossdresser phone sex

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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