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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Forced Feminization Hypnosis

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.

feminization hypnosis

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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Sissy Babies Love Phone Sex Granny Gail

Yes honey its hard to find that special one to understand what a sissy baby needs in the way of care. Well baby, my name is Gail and as a phone sex granny I know exactly the care phone sex sissy babies need.

taboo phone sex granny

See as an older more mature woman I have not only looked after my own kids but have looked after my grandkids and well babysat in general. So looking after a grown man who loves to dress up in pretty frilly baby clothes is easy for me.

I am sure your wondering just what sort of phone sex granny I will be towards you, shall I be strict or a nurturing. Well I can honestly say that I am a bit of both. With my ab/dl I enjoy having fun like most grandmas but if your naughty I will also enjoy punishing you. So the type of fun we have is really up to you. Are you gonna be a good sissy baby or a naughty adult baby?

Good sissy babies get lots of time sitting on granny’s knee snuggling and there is also dress up time cause you are my special baby dolly. Bad sissy babies are often spanked over their diaper covered bum and tied to their high chair while granny makes them eat stewed prunes from a jar.

I really hope your a good sissy baby for Granny Gail as I am looking forward to dressing you up in all sorts of pretty frilly girlie dresses. Lots of ribbons, bows and lace for my lil sissy adult baby.

Bye Bye Baby your phone sex Granny Gail will talk to you very soon. Till then a sweet little kiss on the forehead.

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Sissy Boy Phone Sex with Raine

I was at my girlfriend’s house on the weekend. Suppose to be picking out courses for the coming fall semester. Alright so it was mostly watching movies and chatting about who was dating who now. Never ending drama in the friends circle. We paused the movie we were only half watching so I could head off for a washroom break. The washroom was right next to my friend’s brothers bedroom and his door was partially open.

sissy boy phone sex

As I walked by I could hear Taylor Swift playing softly which I thought was super odd since he was a hard core metal fan. Never heard anything but that since I known him. So of course I had to look in thinking he might of snuck a girl in there. Yes even a kinky phone sex coed can be a bit of a pervert too. Not gonna lie was a touch horny and would of loved watching him get a blow job from some hottie.

I wasnt really ready for what I did see. It was my girlfriend’s brother dressed up in his mom’s lingerie.

Ya! It was a bit of a shocker to say the least.

He was dancing around in black panties and bra and some silk robe. I tried really hard not to giggle but really how can you not laugh at seeing a sissy boy dance around in what can only be his mother’s undergarments.

Sure I have seen pictures of sissy boys who call me for some kinky phone sex fun all dolled up in their favorite frilly outfits.  But to see it in person from someone you have known for a really long time. Gotta say I was a bit stunned.

Well not stunned for too long cause as soon as my brain comprehend what I was seeing I had to run off to the bathroom and laugh. Didnt wanna get caught peeking in on the sissy boy.

Bet your wondering if I told my girlfriend about what her brother was up too?

That little info you will just have to call me for.

Dial the number below and ask for Raine!

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