Category: humiliation

Trans Alexus 1844-332-2639 Ext 349

A client called me today to cry about how his Dad walked in on him masturbating to shemales. Not just any Shemales but to me. I guess he was in his room, jerking away to the porn I fed him and rereading our chats. He had headphones on to listen to the sissy femboi taking a cock pounding from powerful women like me, and he didn’t hear his Dad call to him repeatedly.

Instead of knocking, his Dad just pushed open the door! The worst part is that my poor little fem-loving jerk slave didn’t even feel the presence. So, as his Dad was trying to get his attention, he was just fwapping away.

Continue reading “Caught Masturbating To Shemales” →

Kinky Krysta 1844-332-2639 Ext.410

Ronald wears a chastity cage for me all the time. He only gets unlocked when I have a purpose for his stupid penis. He’s a super dork but a very good boy. I told him I wanted to host an End of Summer pool party ball bash and that I would unlock him so all my hot girlfriends could kick in his balls.

Of course, he agreed because he had no other choice. On the day of the party, twenty girls showed up, all in skimpy bikinis and ready to have a good time. I waited until the girls were good and loose, all relaxed with a few drinks in, and I walked Ronald out on his leash. He wore a tank top with my face on it and regular swim trunks. He crawled on his knees behind me with a bone gag between his teeth.

Continue reading “End Of Summer Pool Party Ball Bash” →

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” →

Sherry 1844-332-2639 ext 399

It’s been a bad week all the way around and I need some fun. I am tired of all the games they play. I need to clear my head. As I walked around the park I decided it was time for me to teach them a lesson they will not forget.

I ran home and got all dressed up. I know where they hang out so I decided I would wear a sexy sheer mini dress. It was green with halter spaghetti straps and the sides put together with metal sterling silver circles and my spiked heel ankle boots. My hair was all curly and sexy and I decided I would wear my glasses. I ordered an Uber to come get me.

Continue reading “Chronicles of Sherry Teaching Lessons Part I” →

Sawyer 1-844-33-CANDY ext 455

My last boyfriend and I had a pact. We only fooled around with other people when we were together. We loved threesomes and couple swaps. We been together for about 3 years and had a very fun and active sex life. It was heartbreaking when i discovered he was meeting with a girl from one of the couples we get with on the side, without me! Revenge was a must. I made some calls to his Dad, his step brother, and the girls boyfriend at the time. When he asked me if we could talk about it I told him when to come over and we would chat. Continue reading “Revenge Times Three” →

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” →

Sherry 1844-332-2639 ext 399

His hands grasped the side of my head intertwining with my hair, holding me in place as he began to violate my mouth.  I could feel his massive hardness pulsating inside my mouth.  With each stroke, I could feel the head of his cock swell inside me.  I knew he was going to erupt in my mouth.

Continue reading “Chronicles Of Sherry-Primed for Sin- Part IV” →

Sherry 1844-332-2639 ext 399

He slid my bathing suit off of me and pushed me onto the bed.  He spread my legs apart as he began his descent to kiss me once again so deeply probing his tongue around mine.  His mouth began to trickle down to my breast.  The moment I have been waiting for.

Continue reading “Chronicles of Sherry-Primed for Sin – Part III” →

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” →

Sherry 1844-332-2639 ext 399

It was late at night when Daddy came into my room waking me up. He covered my mouth and told me not to make a sound. He kissed me and cupped my breast then whispered you will be daddy’s whore tonight. Your new nickname for Daddy is whore.

Continue reading “My New Nickname” →