Category: sissy

Julie 1844-332-2639 Ext 453

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” →

Mila 1-844-332-2639 Ext. 220 Kayla 1-844-332-2639 Ext. 357

Lady Kayla and I always have fun with our little Sissy Sammy! Last time we were in with the hottie, she was really showing us how hot and horned up she is for ladies like us. We obviously knew about her devious little whimpering begging before, but it’s so good to have it in the moment. Dressed up in her favourite sexy silky lingerie, making Kayla and I even more excited to unwrap our little sissy present. Of course, we aren’t going to make this go quickly. Us Candy Girls are ones to savor the moment, especially on occasions with Sammy.

Continue reading “Kayla And Mila On Sammy” →

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

Mama Felicity 1844-332-2693 Ext 270

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.

Continue reading “Girl Talk Confessions” →

Sherry-1844-332-2639 ext 399

I turned the shower on so it could heat up as I unloaded my suitcase. As I got in the shower, enjoyed the warmth and just soaked it all in. I stayed in longer than I should have. I had to rush to get ready for dinner.

We had dinner delivered to my room as we went over the agenda. My boss and I sat on the couch while the CEO sat at the desk. I could feel everything was coming together as I planned. Continue reading “Chronicles of Sherry- Delivering Punishment -Part III” →

Babysitting Mila 1-844-332-2639 Ext. 220

One thing about being a cute teen that everyone loves, is that you get a lot of babysitting jobs. Like, a lot. So many little ones to look after, especially since I have nursery experience! And I always make sure to take as many of these little jobs as possible, because I know those little ones are going to love me! They just can’t get enough of the special games Sitter Mila loves to play with them! Even if they pretend to complain, I always know they watch me leave with that dreamy haze in their little eyes, waiting for me to come right back!

Continue reading “Babysitting With Mila” →

Body Envy

Robotic Rita 1844-332-2639 Ext 413

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?

Continue reading “Body Envy” →

Mercedes 1844-33-CANDY Ext. 423

After a fun afternoon of hanging out with my girlfriends, I return home, finding the house still a fucking mess. I had given you the task to tidy up our apartment while I was gone for a few hours. I should have known that you weren’t capable of following orders too well.

You are sitting in our living room, eyes widened with anxiety, knowing you have failed your task of completely tidying or living space. At this point, you know what’s to come… After I complain about what you haven’t done, I send you to our bedroom to put on the lingerie I had you buy for when you disobey me. “Go to the room and get changed. Come back into the living room when you’re done, you useless scum.”

“Yes, Goddess.”

Continue reading “Punishing My Sissy Husband” →

Zesty Zoey 1-844-332-2639 Ext 403

I love shopping with my sissy.  It’s so fun to find outfits and accessories to turn you into the most perfect feminized sissy you can become.  We’ve spent hours together training you up.  You’ve learned how to be a good little cock sucker.  So, now you’ve earned a reward.  It really does pay off to suck cock like a champion.  You’ve worked really hard to emulate the behaviors of a proper sissy.  Now it’s time to make you look like one.  It’s sissy shopping spree time!  We’ll go to all the best stores and shop together for some sexy little outfits for you to complete your transformation.

Continue reading “Shopping with My Sissy Phone Sex” →

Sherry 1844-332-2639 ext 399

I could feel her calling me and aching for me. I came to her kissing her deeply placing her face in my hand. As I looked deeply into her eyes I knew she was mine. I will make her scream and moan my name. Everyone needs a little TLC.

Continue reading “Chronicles of Sherry – A Little TLC-Part II” →