The Sissy and the Delivery Boy – BDSM


I was absolutely famished. The whole day I made the slave scrub my floors. He was dressed in a black apron with a bit of lace around the edges. It was cute in a way, sort of reminded me of an old fashioned maid… except this maid had a little bottom sticking up in the air as he scrubbed on his hands and knees, not being allowed to walk.

With the sissies ass stuck up in the air, I enjoyed walking by, hearing my heels click on the newly polished floor and giving the slave a few hard smacks with my crop! I just love how the bitch jumps and squirms, but he knows the punishment will be more severe if he decides to act uppity. So as I sadistically give smacks on the slaves ass as he cleans, he knows better than to jump and cry too much.

But I was famished, so I took out my phone and ordered a pizza. The delivery would be at my house within the next 45 minutes. I smiled as I looked at my phone… my plan was in motion.

“Get up!” I shouted at the slave. Slowly, he stands and looks at the ground, knowing better than to give me any eye contact per my protocol.

“I ordered a pizza. I want you to go into the bathroom and go wash yourself up. You are absolutely filthy, but pigs do typically like slop,” I tell the sissy, giggling at my joke.

“Yes Mistress”, says the sissy. I watch as the slave quickly hussles into the bathroom. I hear the shower start and I smile, knowing I have something devious in mind. Quickly, I grab my phone off the coffee table and I start a group text with two of my girlfriends…. “Pizza in 30” I send to all who are privy to my evil plan.

The sissy enters the room and looks down, but I know my slave well enough to know he sees my smiling eyes… he knows I am up to no good. I can smell a bit of fear on him, along with traces of masculinity I’ve been wanting to pound out of that boy for a month now.

“Be a darling and grab me my cosmetic bag,” I tell the sissy slave. He knows better than to disobey my kind commands, as I believe in dominating through femininity. Because I am tough doesn’t mean I still cannot have manners and be polite.

And to my delight, the slave does as told, bringing me my cosmetic bag. Roughly, I grab the slave’s face and start artistically applying a touch of eyeliner and mascara around the eyes. I bring out the slave’s high cheekbones with a touch of blush. But to add an extra layer of humiliation, I decide to go with an incredibly bright red lip.

“Aren’t you a pretty bitch,” I tell the slave, “and your mouth is so red, I would think any man would confuse your mouth with a woman’s well used cunt,” I say with a laugh.

“Yes Mistress,” the sissy answers, looking down. I can tell he’s embarrassed, but also getting off on my little humiliation based on how the penis is slightly starting to swell. I keep trying to discourage the slave’s humiliation fetish, I enjoy truly degrading, but it is of no use.

So naturally, I grab the puffy penis and tug on it a bit. The slave’s penis begins to rise in my hands… only to be put back in its place as I give the little useless thing a SMACK!

“Oof”, is the only noise that comes from the slave. He’s trying to keep it in, otherwise he knows I will gag with the large two inch round ball gag.

“Oh, you just wait, my little pansy. I’m going to show you what you really should be humiliated about. You will learn submission, even if it means I have to take that little troublesome useless piss tube right off your body!” I shout, “Now, let’s get you in the middle of the room. I want you in spreader bars, the ones with cuffs, go grab them off the wall for me,” I tell the slave. I look down at my phone… I need to hurry.

He does as told and hands me the spreader bars and he kneels in the middle of the parlor. I stand up, holding the crop in my hand. Swiftly, I grab the back of the slave’s head, my hand full of his hair, and I push his head right into the ground. “Stay like that,” I shout as I spit onto the slave’s face, “oh no! My spit just ruined your makeup! How dare you ruin my art!” I shout at the slave. “You need punished.”

Walking behind the sissy slave, I grab his ankles and put his feet into the restraints. With his head on the floor, I grab his wrists and put them on the inner restraints, making my slave completely imobile.

The little slave boy’s ass up in the air looks kind of cute and inviting. I love how spreader bars just open everything up, making the sissy easily accessible, yet very vulnerable to my will. I simply could not help myself, I gave a few good hard smacks of my crop onto his ass, and a few light ones on the balls that hang down. “Those little orbs disgust me,” I inform the slave, “we will need to do something about those at some point, they are just too pesky.”

“Yes Mistress.” But right as those words come out of the slave’s mouth, I hear car doors. I rush to my front door to quickly usher in my girlfriends. We greet each other with a few kisses and hugs, but almost immediately their eyes are going directly to the slave bound and exposed on the floor. Pip began to giggle and Leslie commented on how I at all times discover the true freaks.

Exactly on cue, I hear another car door, but this one is coming from the road in front of the house, not the driveway. “Who’s hungry?” I ask the girls.

As they start to giggle, already aware of my plan, there is a knock on the door. I take a deep breath and answer it slowly, “is that our delivery? Extra sausage?” I ask the pizza delivery guy.

“Yes ma’am,” he says.

“I already paid online, and I see it’s 9 PM, so this is your last delivery… are you sure you won’t join us for a slice?” I ask the pizza delivery guy.

He looks inside and smiles at my friend Leslie. “Well, who can refuse a group of cute women, and I am off the clock,” he says as he enters the house.

“Do you see the table in the center of the room?” I asked the pizza delivery guy, “will you go put the pizza on the table?” As I say this, I strut over to the slave who is restrained in spreader bars. “This is Pansy bitch, and today he is our dining room table, but as you can see… we aren’t fine dining,” I say with a little laugh.

The pizza delivery guy looks a bit hesitant, but Leslie gives him an encouraging smile. I look at her, giving a very stern look as she knows what it means… if I’m fulfilling a roleplay, I want everyone in character. He takes a deep breath, and walks over to the restrained slave and lays the pizza on his back. We all come over to the impromptu table and grab a slice, including the pizza delivery guy.

“Isn’t it nice when we have exotic things?” I ask the group of girls and one man in the room. Everyone sort of giggles as I take charge of the situation. I can see how I’m the only one comfortable with the objectification of another human being, but I notice how everyone looks very excited by this notion. I eye the delivery guy even more, like a lioness going in for the kill. “Haven’t you ever wanted to try exotic things?” I asked the delivery guy directly.

“I mean…” he says with a pause, “I mean, yeah, who hasn’t wanted to do some crazy things. But you girls look plenty crazy enough,” he says nervously.

Leslie moves in a bit closer, I can see she has hungry eyes. Following her cue, I grab the pizza box and move it off the slave’s back. “Oh goodness me,” I exclaim, “I never actually tipped you. How silly of me!”

“It’s okay ma’am, I don’t need a tip, the slice of pizza and conversation was more than enough,” the pizza boy says politely.

“Hmm…” I purr, “I can think of another tip for you,” I say, winking at the delivery guy, “or at least a place where you can put your tip.” I say with a giggle, only to be mimicked by the other ladies in the room.

He looks nervous, “and where does the tip go, ma’am?”

I walk to where the slave’s head is still smashed on the floor. Slowly, I bend down and my breast spills over my top, giving the delivery boy quite the show. As I seductively expose my breasts over the slave’s back, like a snake, I slither my hands onto the slave’s striped ass.

Grabbing the slave’s ass cheeks, I spread the sissies ass even wider than it already is being restrained in the spreader bars. “Right here,” I say, “Put your tip right here!” I use my sexy but dominant voice, commanding the pizza delivery boy to obey my will. “We all want a show, and you had a very long and hard day at work… Come on, boy, use my sissy bitch” I pause, “When was the last time you had a hole just for your use?” I say, but I look up at Leslie as I say these words.

“Let me help you with that,” says Leslie. She reaches for the front of the delivery boy’s pants. I watch as she unbuckles his belt and begins slowly unzipping his pants. With her touch, I see the bulge that was already there to start with began to grow even more.

“Come on now, I even want a show!” chimes in my best friend Pip. The flush of her cheeks let’s me know just how excited she is, hoping this plan comes to fruition. Pip is quite the voyeur.

Looking over, I watch as again the pizza delivery boy takes a deep breath, eyeing us ladies in the room, but also looking down at the objectified slave boy’s ass spread in front of him.

I decide to push things along and I grab some lube from the cosmetic bag. I slowly start to pour the lube all over the slave’s ass, knowing it is cold on the slave’s skin. The sissy jumps a bit as I watch the goosebumps, showing how the sensation of the slipper lube begins to affect the slave.

“He’s all oiled up and ready to give you your tip for us, like a good slave does. He likes to be used by his betters” I say. I take a few steps back as I see the delivery boy’s cock is nice and hard, as Leslie has been slowly stroking his cock.

Unable to contain himself, the pizza delivery boy gets onto his knees and grabs onto the slave’s hips. I watch as the delivery boy begins to stick his hard cock into the slave’s tight ass. As the sissy cries out from being penetrated, we all start to cheer as we watch the masculine man take power over the restrained, helpless bitch.

He begins to pump harder and harder, slamming right into the slave. I hear the cries of my slave, but also the masculine moans from the man who is dominating via his cock. I watch this primal scene in delight, knowing just how much I am humbling the slave on the floor makes me wet and excited.

I look at my other two friends. Pip is visibly excited as I watch her bite her lip, her eyes locked into the dominant man pounding the vulnerable, helpless bitch boy on the floor. However Leslie seems the most excited. I see her watching intensely, unable to help her hand grabbing her left breasts as they heave with her heavy breath. Leslie has a smile of lust on her face, excitedly watching the large cock thrust and take what is his before him.

Faster and faster, I watch the man’s cock really ram my slave. I let out little humiliating remarks, reminding what a bitch he really is, reminding that he wanted real humiliation, so I made the decision of real degradation. Verbally I humiliate and degrade, reminding what a pathetic state he is in. How can one be masculine when a real man is taking your asshole like a cunt? How can you be masculine as your makeup runs from your eyes with your tears? And how dare you ever think you are a man again!

I watch as the real man’s heavy balls slap against the small and beaten balls of the bitch retrained on the floor. But alas, after quite the show, the delivery boy eventually cums, letting out a manly growl as he does, burying his cock deep inside the slave’s tight little ass. The girls cheer and laugh, but I reach for my phone to take a picture of the cum running out of my property’s asshole, seeing it gape in embarrassment and shame.

The party dissipates quickly after the show as I order Pip to go into my bedroom and I will meet her there in a few minutes. Leslie and the pizza boy both leave quickly. I watch from the window as Leslie and the delivery boy makeout passionately beside her car. It brings me a bit of joy that I was able to fulfill her ultimate fantasy of watching her husband take the manhood from another man. I feel happy that I was able to help put a spark into her marriage. But I am also proud of myself for breaking my submissive little sissy from ever thinking he is a man again! Every way you go, this was a wonderful evening.

After the fun is all done, I crop the slave’s ass a few more times before I let it up. “How does it feel to have a real man’s cum inside your ass for the past 10 minutes, as you just sit there and take it, objectified and truly humiliated by a room full of women?” I ask the slave.

“Yes Mistress,” is all the little bitch says.

“So pathetic,” I remind the pansy boy, as I decide to let him out of the spreader bars.

His muscles quiver as he manages to stand up. “You may be dismissed for the night. I want you to go home with an ass full of man milk, unlike your watery little sissy squirts,” I order the slave. “How does it feel to be fully emasculated? Did you get the true humiliation you were after?” I ask in a very mocking tone.

“Yes Mistress,” says the slave, looking genuinely embarrassed.

“That’s my good bitch. One more thing,” I say before I dismiss the sissy for the evening, “when you go home and you see your lipstick in the mirror… it looks every bit as messed up and blown out as your asshole is. I guess you can say, you are nothing more than just a sloppy used cunt.”

And with that, I watched as the slave exited the house, saying thank you Mistress before he closed the door. Quickly, I run into my bedroom ready to ravage Pip, my cunt throbbing still from the just witnessed show.

~MistressThrope

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