SISSY BOY CONFESSIONS: Making Him My Craigslist Whore, PT. 1

sissy boy confessions

I’m going to get those sissy boy confessions out of you, no matter what it takes.

I love sissy boy confessions. What secret fantasy could be more understandable than wanting to be a girl? I certainly can’t blame them! Much to my cruel Mistress delight, one of my favorite submissive sissy boys called me tonight. We’ll call him “D.”

“Are you at the office tonight, D?” He often called me when he was staying late and not strictly working from his office.

“No, Aileen. I’m not at the office because you and your friends tied me up, blindfolded and ball-gagged me and left me here while you went out. It’s been hours and I have no idea what’s going to happen next.”

On my end of the receiver, an evil grin instantly spread across my face. Perfect. Nothing gets me feeling “ready for showtime” quite like a heavily restrained, muzzled and overall beyond helpless man. I leaped up out of my office chair and began to pace down my hallway towards the front door, imagining myself coming back home to my helpless prey.

“How would you know how long it’s been, D? You can’t see anything. But you have been waiting there so long you’re drifting in an out of sleep. All of a sudden you hear a loud banging upstairs, I’m finally back with my girlfriends. We had a fun night out partying. And now we’re going to have some fun with you.”

Sometimes I think sissy boys let themselves get caught because they want to be punished.

“We’re going to dress you up like what you really want to be, D: a girl. You’ll never be a real girl, but I’m going to help you look like as cheap an imitation possible. But a two-dollar whore. Understand, bitch?”

D let out a garbled half-choke of feeble protest. For me, the best phone sex isn’t complete without at least a few pathetic sissy boy whimpers. “But Aileen, I was just sniffing your panties! That’s all! This is too much! It’s not fair. Please, no!”

“Forcing” sissy boy confessions out of panty sniffers like D is an art. I knew when I first met him he was much, much more than a casual lingerie thief. His longing to bury his face in my dirty silky panties sprung from his secret desires to be force-feminized and forced to suck cock.

“Bullshit. It’s time. Girls, put our confused little cocksucker into her outfit!” I laughed like a deranged, sadistic hyena as my pretty girlfriends pulled D into a red patent leather minidress. It was a slutty little number, with an open back, straps that tied like a bikini and openings along the side and underneath where tits were supposed to be. However, I preferred how ludicrous D looked without stuffed tits.

Sissy boy confessions need to be heard. Who would want to live as a man forever? What a sick life that would be. I love making D’s bitchy girlfriend fantasy cum true by controlling him and dressing him up. But best of all I love forcing him to suck and fuck cock.

After taking plenty of photos of D as my pretty sissy slut, I post them online. Otherwise, how will I find an appropriate male suitor?

I make D, now going by his feminine name “Deanna,” run to the door with a buttplug stuffed in her ass when our first visitor arrives.

“Tell the nice man you want his cock in your mouth, Deanna.”

“Please no, Mistress. Please!” During these futile shrieks D used her “girl voice,” which I chide her sounds like a muppet being strangled.

“Don’t you DARE argue with me, you disgusting whore. And your voice, Deanna! Pathetic. Pitiful. I know you can do a better girl voice than that, slut.” I leered down at her with something beneath contempt. “Let’s try again. And on your knees, this time.”

Deanna’s heavily make-upped eyes twinkle with fear and excitement. Recently, during our pillow talk, she told me she loves it when I make her “moan like a girl.” Seems like she always needs more practice, though!

Want to hear the rest of this story now? Guess it’s time for you to stop daydreaming about me catching you stealing my panties and give me a call, sissy boy!

sissy boy confessions

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