Crossdressing Sissies

~~~Olivia ~~~ 844~332~2639~x~226~~~

Crossdressing sissies are so interesting to me.  I have a few who have been with me for a long time even after training is over.  Girls, you know how we shop for that special outfit. Every thread is to be inspected.  The color has to be a certain hue, and the shape has to be just so therefore has to have all accessories matching. The newest photo I received shows her walking her dog early morning in full dress.  Her navy blue leggings with a matching hoody pulled over her head. The face is in full makeup and the wig is brushed, the nail polish to match, Ugg’s shoes round out her outfit.  You would never believe it is the same sissy I started out with. For one thing, I couldn’t get her to go out even at the night.

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Tranny Tease Phonesex

Shemale alexus looks so pretty in a white blouse and grey jeans

Shemale Alexus 1844-332-2639 x 349

He said he was shopping for his girlfriend, but the sales clerk and I knew the truth. He was just another wanna-be tranny too scared to be herself! She looked him up and down and asked what size his girlfriend was. “Oh, um. I don’t know.” He blushed a deep red. “Kinda…my size. I guess.” The clerk looked at me, and we both nodded.

“I’m also shopping for my …girlfriend.” I teased and touched his elbow. “Why don’t I show you some things my girl likes, and maybe we can pick out some things that will be just right for you. I mean your girl.” He thanked me with a stutter and looked at me in awe.

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Be A Girl For Me Phonesex

Redheaded Kayla poses against the tile wall in pink lingerie

Kayla Cumsalot 1844-33-CANDY ext 357

Recently we moved in together. I used to think you were so masculine, but now that I live in your space, I see some huge signs that things aren’t as they seem. Your pillowcases have frilly trim, and you’re far more organized than I am. The bathroom counter has more facial moisturizers than the grocery store; I mean, come on.

When you get home from work, I’m sitting on the couch in some sexy lingerie and high heels. You give me a catcall when you walk through the door, and I smile. The way you look me up and down reminds me why I love you. “Damn, girl!” You coo when you scoop me into your arms against your chest.

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Dressed Like a Slut, Fucked Like a Slut Phonesex

Anita  1-844-332-2639  ext 288

I enjoy seeing the twinkle in your eyes when I let you into my closet and let you pick out any outfit you want, especially when I let you rummage through my lingerie.  When it comes to your hair, I enjoy putting on a beautiful wig on you, adjusting it to look perfect, then followed by doing your makeup just like any other girl would.

Taking pictures of you as you prance in your heels with your full body fully shaven.  Your feminine and painted nails compliment you your tight and scandalous lingerie.  This is when you will have to realize that when you dress like a slut you will get treated like a slut.  Perhaps I should rephrase myself.  If you dress like a slut..

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Secret Shopping Trip Phonesex

Madison (a.k.a. bratty Maddi)  1-844-332-2639  ext 359

Let’s go on a secret shopping trip.  Let’s get you some super duper sexy panties and a lil cock cage to lock up that clitty.  After all, we don’t want your boring wifey knowing that you’re a closet sissy and that you love playing dress up with me….giggle.  Since I’m the real girl here, I can help you pick out the right colors and the right sizes.

Then one we have the right panties picked out, let’s figure out the right cock cage for your itty bitty clitty.  We don’t want that gross man dick taking over…giggle.  Oh, and let’s not forget a cute and sparkly buttplug with some swarowski crystals.  If you’re going to be a really slutty sissy girlie, you definately need the right toys and bling. 

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I Wanted A Man Phonesex

Pretty redhead wanted a real man.

Kayla Cumsalot 1844-33-CANDY ext 357

 I wanted a man but you fooled me, good. I really believed what you presented. When we met, I thought you were a man. I guess you are used to fooling everyone with your fake life. It probably isn’t even a struggle for you to puff out your chest and beat on it like the Alpha man you wish you actually were. It’s a shame really because I thought we would be good together. Maybe even grow old together but now I know that will never happen because you are not really a man.

You are a sissy in disguise! How could I ever love a sissy who doesn’t own his truth?

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Sissy Fashion Advice from Collette Phonesex

XXX  Mistress Collette  XXX  1-844-332-2639 ext 383

When I see you at this one specific store, I know exactly what guys like you really want to be wearing.  You don’t want to be wearing to ugly boys clothes, instead you want to wear something more girlie.  Guess what?  I’m a sexpert in girlie clothing and fashion.  I can take you into the dressing room and give you the exact outfits which you should be trying on.

I will suggest for you exactly what you should try on.  As you’re asking yourself “If I want to be a sissy girl, what exactly do I need for my wardrobe?”  I will let you know exactly what you need. 

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Sissy Panty Lust Phonesex

Sissy Panty Lust Phonesex

844-332-2639 xxx 345

You sissies adore lingerie. I can not tell you how many times a sissy requests to change into something sexy before our sessions. Sissies naturally gravitate towards beautiful and delicate clothes. Every ounce of your being is drawn to being more feminine. You will not be able to control yourself when you hear about my lingerie collection. Sissy panty lust is a real thing you know.

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Stripping At My Sissy Sleepover Phone Sex!


Gianna 844-332-2639 ext 355

You’re still trapped at my place so it feels like we’ve had this extended sissy sleepover. It’s been so fun though! One night after having too much to drink, I dared you to strip in front of me. I’ve forced you to always wear sexy lingerie underneath your clothes so I’m excited to see what you have on today. You begin stripping your clothes off when I catch you not wearing anything at all! Wtf! I’ll have to punish you now!

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Willow’s Silky Stockings For The Holidays Phone Sex aka Santa Is A Sissy


WILLOW 1-844-332-2639, ext. 230

There is just nothing sexier than silky stockings pulled taut over even sexier, shapely legs. The texture and feel of the nylon hosiery just exudes sexiness. What if Santa was a lingerie perv? When he sneaks into houses late at night instead of going for the plate of cookies he heads straight for the lingerie drawer.

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