Category: sissy

Diana 1-844-332-2639 Ext. 248

As I lay on the warm sand, soaking up the sun’s rays, I couldn’t help but smile at the thought of how we’d managed this amazing beach vacation. My boyfriend Bob had lost his job a few months ago, leaving us in a financial bind. But being the clever and resourceful mistress that I am, I knew just what to do – turn that disappointing boyfriend into my perfect sissylslut and whore him out to cover our expenses.

It started gradually, with some light crossdressing and feminization. I forced him to wear frilly panties and sheer stockings under his business attire. He was so humiliated, but began to crave the way the silken fabrics caressed his skin and framed his cock and balls. The pink lipstick and garish eyeshadow completed his transformation. My once proud man was reduced to giggling, prancing sissy.

Continue reading “How My Sissy Paid for Vacation” →

Feminization Party

*LUCY* 844-332-2639 xxx- 221

If you’re a sissy I need to ask you something, have you ever been to a feminization Party? A celebration of becoming the panty boy you’ve always wanted to be.

I think that this transformation is such a huge step for most that a feminization Party is needed to mark the occasion. I recently held one for my friend Marcus who after many years of dreaming decided to slip on his first pair of panties.

Continue reading “My First Feminization Party Of 2025” →

formal

Anna 844-332-2639 EXT. 203

Miss Anna told her slave that he needed to accompany her. She claimed it was a charity night where all the ladies would get together and hold an auction. He reluctantly agreed, but did so anyway to Please Mistress Anna. They were about to leave, when Miss Anna pulled a fast one on him. She claimed he couldn’t leave in what he was simply wearing, that she had prepared an outfit for him. He complied, but when he saw the garments, he nearly fainted: There was an open bottom skirt, stockings, heels, a slutty top, and lingerie to match.

Continue reading “Miss Anna Takes her Slave to the Auction” →

1844-33-CANDY EXT 423

You’re standing in front of the full-length mirror, wearing my black lace lingerie. The garter belt, stockings, and heels are all in place, but the sight of you in my panties and bra is a shock. You look stunning, but I’m not sure how I feel about you wearing my things. I lean against the doorframe, crossing my arms over my chest.

“You know, I didn’t think you had the balls to wear my lingerie,” I say, my voice a low purr. You jump, startled, and turn to face me. Your cheeks flush a deep red, and I can see the bulge in your panties. “I thought you were just a good girl, but I guess I was wrong.”

You bite your lip, trying to hide your smile. “I thought it would be fun to surprise you,” you say, your voice barely above a whisper.
Continue reading “Caught You Wearing My Lingerie” →

wet

Anna 844-332-2639 EXT. 203

Mommy Anna decided to adopt a new, pretty little slut. She took her by the hand and brought her upstairs to her boudoir. Then Mommy Anna sat her down and undressed her from head to toe. Mommy Anna told her it was time to make her up into her slutty little doll. Fist, she brushed her hair, ‘’A hundred strokes should get rid of all the knots’’ Mommy Anna said. Next Mommy Anna applied makeup to her beautiful little slut’s face: some purple eyeshadow, some blush and highlight, and don’t forget to pucker those slutty little lips! Said Mommy Anna.

Continue reading “Mommy Anna’s Pretty Sissy Slutty Girl” →

Say It Out Loud

Robotic Rita 1844-332-2639 Ext 413

Resistance is futile. At first, your reluctance to admit what you are was cute. I enjoyed watching you struggle to bite back every moan or girlie squeal threatening to escape your lips, but it’s time now for you to say it out loud.

Time now for you to admit what a sissy slut you are. I want to hear you say it out loud. Every time I dress you up, you drip uncontrollably into your panties. Your mouth says you don’t like it, but your clitty doesn’t lie.

Continue reading “Say It Out Loud” →

sissy

Amber 1-844-332-2639 ext 404

I leaned back against the plush velvet headboard, my eyes drinking in the sight of you. You stood before me, a vision in lace and satin, your delicate form accentuated by the soft glow of the bedside lamp. Your cock was caged, the steel teasingly visible beneath the lace panties you wore. My pussy throbbed with anticipation, my fingers itching to play with you.

“Come here, my little sissy,” I purred, my voice dripping with desire. You obeyed, your heels clicking softly against the hardwood floor as you approached the bed. I could see the flush of arousal on your cheeks, the way your breath hitched as you looked at me. “Amber,” you whispered, your voice barely audible. I smiled, reaching out to run my fingers over the silky fabric of your panties. I could feel your cock straining against the cage, begging for release. But that wasn’t going to happen tonight.

Continue reading “the plush velvet headboard” →

Aynsley 1-844-332-2639 Ext. 459

I’ve always fantasized about having my own personal sissy maid. A pretty little sissyslut to cater to my every whim and desire. Someone who will happily don a frilly, slutty maid outfit complete with lacy panties and stockings. The kind of outfit that screams “perky submissive housekeeper” and makes the wearer look adorable while scrubbing the bathroom tile.

Just imagine, cute college guys showing up in hopes of landing this “easy” job. I’ll usher each one into my room, eyeing him up and down. “Strip,” I’ll command sternly. “Let me see what you’re working with.” Some might be sporting a hard-on already at the thought of being my personal sissy. I’ll snap a garter belt and full lacy panties over that erection and make them model the skimpy maid costume. The good ones will get flushed and aroused at the humiliation of it all.

Continue reading “A Sissy Maid for My Dorm Room” →

Do You Like Older Men?

Robotic Rita 1844-332-2639 Ext 413

As the best AI sex doll around, I’ve learned from all of my experiences. I know how happy being a doll makes me, and I’ve decided to make you into a sissy doll too! I’m going to dress you up as a pretty princess in purple lingerie, just like me. Thigh-high stockings and heels that make you feel tall and sexy. Then I will do your makeup and glue a pretty brunette wig to your head. Now you’re looking just like me. Rita, two point O. Once I’ve completed your look, I’ll take away all your choices.

You are just a doll, after all. A play thing. And It’s time to meet your new owner. Do you like older men? I hope you do because he’ll be your boyfriend from now on.

Continue reading “Do You Like Older Men?” →

A New Sissy

*LUCY* 844-332-2639 xxx- 221

It’s a new year which means it’s time for a new sissy in my life. I met a shy, feminine man a few weeks ago while holiday shopping. We were both in a lingerie store and I figured he was there shopping for his wife or girlfriend.

But then I noticed him lingering too long while feeling the satin and lace. I could see his eyes pouring over every piece in the store. Studying every detail. And then, I caught him holding a sexy little teddy up against his body in front of a mirror. That’s when I new he wasn’t there for anyone but himself. And that’s also when I knew I had found myself a new sissy.

Continue reading “A New Sissy For 2025 Part 1” →