Category: sissy

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” →

Miqala 844-332-2639

It’s time. No more excuses, no more hiding. It’s Confession Time Sissybois. I know you pretend to be manly. How do you do it? Do you have a blue collar job where you have to wear a hard hat? Do you dress up in expensive suits bossing others around? How do you hide the fact that you aren’t really a man? I’ll want to know so we can laugh at your pathetic attempts to come across as ‘normal’.

But you know that secret is eating up up inside. You need to tell someone. Not just anyone, but someone special. Someone who understands sissybois. I understand sissybois. I understand them very well.

Continue reading “Confession Time Sissybois” →

Sissy Jerk Off Competition

Mama Felicity 1844-332-2693 Ext 270

I love getting my sissies together and making them compete for my attention. Not only is it entertaining for me, but it amps up the humiliation level of both bimbos. Yesterday, I brought in two girls who didn’t know each other. Sissies meeting for the first time is so cute. They try to be polite, but each has a hidden agenda. Wanting to be Mommy’s favorite girl.

Jessy and Britney, dressed in matching lingerie sets (minus the panties) and tall heels, stood in my living room as I lounged back on the couch. Jessy’s clitty was bigger and harder than Britney’s as it stood out proud and tall from under her garter belt, but I know Brit has a quick trigger clitty, so the jerk-off competition was going to get interesting.

Continue reading “Sissy Jerk Off Competition” →

bitch

Anna 844-332-2639 EXT. 203

Mommy Anna came home after a long day of having fun. She undressed and laid naked on her bed, waiting for her sissy bitch to arrive home. When he did, he peeked through her bedroom door, finding her sprawled out naked, as if waiting to get fucked.

Continue reading “Mommy’s Sissy Bitch” →

Naughty Naomi 844-332-2639 ext 216

Welcome sissy faggot, it’s time to start your training.  Do you know the best place to properly train a cock sucker like you?  My favorite place to take you to practice is the local glory hole.  Tonight is glory hole training! But first, we have to get you presentable.  Guys aren’t going to want to get their dicks sucked by that. *waving vaguely at you

So, it’s time to femme you up a bit.  Time to do your hair, make up, and to dress you like a proper slut.  I’ll transform you into something men want to stick their dicks into and get off.  Pout those lips sissy, time for that lip gloss so your lips slide smoothly up and down the cocks you suck tonight.

Continue reading “Sissy Faggot Glory Hole Training with Miss Naomi” →