I’ve been humiliating a new caller during sissy loser phonesex ALL week. He’s obsessed with me, and begged me to write a blog about him. He has a tiny “penis,” can’t cum unless he’s rubbing it with TWO layers of nylon stockings or panties, and is a glutton for punishment. Do you relate to this client’s pathetic plight? Well, maybe it’s time for you to stop compulsively masturbating for TWO seconds to pick up the phone and call me. It’s not like you’re going to be able to cum on your own, is it?
As I constantly remind my new crossdressing client, I don’t really care if you cum. In fact, I don’t care at all! YOU are the only one who cares about that, not to mention the only one who cares about that nasty little thing between your legs. During sissy loser phonesex, we’re going to discuss the “implications” (ha ha) of this, and oh-so much more.
My new sissy loser has so many embarrassing “habits.” First of all, he prefers to be wearing nylon stockings at all times. Not just when he calls me. This sissy loser idiot (we’ll call him “K”) wears his silky, skintight little stockings under his ridiculous “Regular Guy” costume when he’s out in the world. Yes, he’s crossdressed UNDERNEATH as he goes about his daily boring business. Shocking, sad, but true!
As I remind K during verbal abuse phone sex, he WISHES he were a “real girl,” that he had transitioned, but he’s too much of a spineless, pathetic wimp to have ever done anything about it. So many wannabe, pussy envious perverts call me for sissy loser phonesex. Are you among these closeted, clamoring covetous freaks?? Good. Time to give me a call so that at least there’s ONE woman you can be honest with, even if it isn’t yourself.
It’s time to tell me your “worst” secrets, the ones that are already true and of course, all your deepest fears during sissy loser phonesex. All the better for me to exploit them and humiliate you, you effeminate moron. Sissy K told me a HILARIOUS true story from her sad, sordid life that was quite embarrassing. Apparently, decades ago, she was invited by her new manager (after a few drinks) to a bonafide gangbang. The woman was willing and eager. But, unfortunately, Sissy K’s little appendage down there was not. Nor would it ever be. Despite not being able to get hard, Sissy K “went through the motions” anyway. Ha ha. This is the kind of confession I love to hear during sissy loser phonesex.
Are you ashamed of your secret desire to enjoy my delicious, golden piss streaming into your mouth? I have plenty of golden showers for you, girly. What are you waiting for? I’m right here, ready to laugh at you.

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Megan is extremely open minded. Plays along with even the most taboo fantasies. Close your eyes and enjoy!
Jamie has gotten insanely popular, so she is often “busy” or “offline,” but a call with her is well worth the wait. Sweet, attentive, and often funny as well as dirty, she has raised my fantasy role-play into something hotter than I ever imagined it could be.
Paris is incredible! She has such a sexy voice and an open mind.
My first call with Dixie was so fantastic! Unbelievable voice! So soft, so sweet, so nurturing, so Southern! Dixie is everything I ever wanted in a Southern lady. Her voice will leave you shaking and breathless as she weaves her Southern charm and teasing into your mind. Dixie is the one I have waited for my whole life! Five big stars for this sweet, classy Southern lady who touched something very deep within me. I LOVE Miss Dixie! The Southern Belle of my dreams!
Brittany is the best! She remembers and always engages. Others sometimes guide the call through a generic script and don’t really listen. Brittany ALWAYS shows up and makes you feel like you’re special and important!
Brittany knows exactly how to get me as turned on as physically possible. She is amazing.
I have been calling PSK for well over 10 years. This was my first call with Skye and she was amazing. She is beautiful and her voice is so sexy. I laid some frame work for a nurse role play and Skye took it from there. I will be back every 2 weeks for my follow up appointments and physical therapy. Thank you, Skye.
I just finished my second call with Skye, and she is such a sweetheart. She’s easy to talk to and made me feel very comfortable. I’m very much looking forward to talking with her again.
Jesse is incredible, a true professional!! I love talking with her.
Yesterday I was honored again to be in Aileen’s presence. What an amazing call. We touched on the 10 tenants of Aileenism that I have written for Her. Call Her and perhaps She will share them with you. I love ❤️ and worship Aileen. As it says in Aileen’s Holy Scripture chapter 13 verse 15: Though She slay me yet will I trust in Her.
Roxy is awesome, especially if you like to roleplay. You will not be disappointed when you call her. Her oral skills are insane. She likes to blow more than your mind.
I can’t say enough good things about Raven. From her sexy voice to her storytelling skills, she’s outstanding. She definitely pays attention and follows along in roleplay. Definitely one of the best.