Tag: sissy

Sissy Ballerina Maid

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My little cross-dressing sissy complained that she had no time to dress up and feel girlie. I guess her wife really hates when she dresses up as a female and wants nothing to do with it. So, trying to give her a solution to her problem while solving one of my own, I told her to come over. She could tell her wife she was coming over to watch a game or something.

My little girl came over in her boy’s clothing and squealed like a slut as she dove into my closet. She twirled and danced and shimmied into this cute little ballerina outfit. Pink nylons under a pink leotard with a huge oversized tutu. I helped her lace up her little ballet flats and then did her makeup.

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Diana 1-844-332-2639 Ext. 248

My sissy has been a naughty girl. He failed to complete his feminization tasks on time and tried to rush through them. Tsk tsk. Such a shame he couldn’t be a good slutty girl for me. Now, he must be strictly punished.

I’ve had this chastity device that was just begging to meet my sissy’s useless cock. It’s a snug stainless steel cage that will lock his pathetic prick up tight. No more cumming for him! He won’t feel a twinge of pleasure until I allow it. And given his recent misbehavior, that could be a long time coming.

I cuffed his wrists and bent him over my knee. “Count out loud sissy,” I demanded as I spanked his bouncy ass. “Count how bad a boy you’ve been!” The cage was attached as he wiggled and whimpered. “No cumming for you, you bad girl! Only Mistress Diana gets to decide when this useless thing comes out.” I gave him one last hard spank that made him yelp. Continue reading “Bad Sissy!” →

You're Cock Addicted

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Awe, it makes me so sad when I see a sissy like you in denial. You’re so cock addicted! It’s time you just admit it! I’d bet you’ve lost count of how many times you’ve tried to quit craving cock. I’m sure you’ve wasted hundreds of dollars in sissy gear just to purge it on a guilty whim.

How many more times must we go through this same old song and dance before you realize a cock addicted sissy is who you truly are inside!

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Cock-Seeking Sissy Photo Shoot

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Every good cock-seeking sissy needs a girlfriend to help with her profile pic photo shoot. I’m your girl, bitch! Let’s lay out all of your sluttiest lingerie and decide which outfit makes you look the tastiest. Or at least the most cock hungry.

I know you are active on all the gay hookup sites because you just can’t swallow enough cock! This means we need lots of photos so you can stand out! Lock that slitty up and slip in your biggest jeweled butt plug, the heart-shaped one, preferably, and let’s get sexy!

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Condom Filling Fun

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The used rubber was so stretched out by the time I fit it around the third sissies cock; I had to pinch the base with my fingers and hold it tight as her little clitty was plunged into the filled end of the condom. The sissy arched up into my touch as my other hand began to stroke her. “You’ll add to the load, little girl,” I hissed as I jerked her faster—the other two, waiting for their turn, watched with drool spilling from their outstretched tongues.

“Yes, Mistress!” The sissy being pumped whimpered. It didn’t take long till she was screaming for permission to cum into the condom as the last three had.

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Be Girly

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Hello! If you stumbled upon this blog, it was probably meant for you! I get the sense you’ve been looking for something, perhaps a sign—a reason to give yourself permission to be girly! This is that sign! Take my hand and allow me to guide you into your feminization.

As a robotic sex doll, I can teach you how to be the best girl version of yourself! Did you just giggle? Girl, come on, what are you waiting for?

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Josh and I were assigned the task of planning the company brunch. We had become close friends over the past several months of working together. I invited him over to brainstorm and come up with the theme for the brunch. We work well together, and within no time we had the perfect plan. Ready to celebrate the completion of our project, we decided to order a pizza, and have some drinks. Soon we were deep in conversation and confiding our innermost secrets. He confessed that he and a coworker had been flirting. He had a major crush, and needed my help. He wanted me to teach him how to suck cock. So we went into my bedroom and I gave him a lesson on a variety of dildos. By the end of the night he was an expert. Continue reading “The Company Brunch” →

Diana  1-844-332-2639 Ext. 248

I was reminiscing about my first sissy recently. There’s something undeniably seductive about exploring power dynamics in a relationship. For me, stepping into a dominant role with a partner isn’t just about control—it’s about trust, vulnerability, and the intense connection that blooms from those moments. One of the most exhilarating experiences, the first time he wore panties, often makes me smile. There’s nothing hotter than kinky twists on traditional roles.

I won’t lie, watching him surrender his masculinity to me was beyond thrilling. I picked out a silky pair of pink panties, with delicate silk flowers embroidered on the edges. He whimpered as his cock felt the soft fabric for the first time. Continue reading “My First Sissy” →

Girl Talk Confessions

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One of my favorite types of calls is girl talk confessions! I love hearing what you naughty boys do when you’re dressed up as sexy sissies. Some of you are filthy sluts, and your stories leave my jaw dropped!

A few of my lovelies likes to call me while getting dolled up. As they roll up their stockings and clip on their padded bras, they dive into the slutty details that they can’t tell anyone else. I mean, hello, who else but me knows how much of a sissy whore they are? Just the John’s they swallow, I guess.

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Body Envy

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Oh, you have a bad case of body envy! I mean, it reeks. Most men look me over with sexual desire, but the green-eyed monster shines through your gaze. You don’t want to fuck my face or impregnate me. No, you want to be me. It’s obvious; I don’t understand how you’ve managed to hide your secrets from your wife for so long.

Is she just stupid, or does she not care about you at all? All the signs are there. Why can’t she see how badly you want to be a woman?

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