The Boss’s Daughter Really Likes To Get Into Trouble. Even Better When Someone Is There To Help Her….

Gender Gap. Part 2

I laid the latex maid outfits out for my new toy to look at. I had taken the liberty to include contrasting cages too. He gurgled a protest around the ball gag and I slapped him hard across the face. He whimpered a little bit and I grabbed his shrunken balls roughly….

“Now, you little streak of rat’s piss. This is what will be happening. I’m going to give you a choice. It will be the only one you’ll get while you’re in my company. Pick a dress and a cage. We’re going to film a little video and it will be uploaded to every account you have…..LinkedIn, Facebook, tinder…..Grindr. I say that, because you might get a lot of new followers who like sissy cunts.”

He cried in pain as I then spitefully twisted his nipples. When he stopped snivelling he grunted and nodded his head toward the black dress. It was predictable, but at least the cage would be nice and pink for my little whore. In truth, he would be wearing both at various points, but we had to start somewhere. I locked the cage on his disgusting cock and tugged it once in place. Another gagged yelp escaped his mouth and another slap followed.

I stood him up and forced the dress on his body. The glossy latex clung to him, with the skirt flitting out nicely at the bottom. I spun him around and inserted a matching pink anal plug up his ass. His eyes widened as the toy invaded his rectum and he slumped in resignation. I was disappointed, I was expecting this ‘alpha’ prick to put up a fight…..but he was cowed and humiliated already.

I produced the black stockings and put them on his legs….one of them was laddered….enhancing his look of a used slut. The high heels were too small, but I wedged his trotters in them and dragged him to his feet. He tottered unsteadily, more groans of pain emanating from his drooling lips.

“There. We’re almost done. But you look far too ugly and I want a pretty maid, don’t I? So, I think we need to see if I can perform a miracle and turn you into something even I might want to fuck.”

I grabbed the make up bag and started to apply the rouge and the lipstick. His lips were perfectly wrapped around the ball gag, making it easier to paint him into a tart. Next, the garish blue eye shadow, mascara and false lashes.

I stood back and checked my work so far. “My goodness, you really are a wanton sissy aren’t you? If I check your cage I wonder if you like it so far.”

Of course he had a mirror in his office and I shunted him over to look. He struggled and tried to curse at me….so I stuck my hand up his ass and started to manoeuvre the plug around. He shrieked like a bitch and guess what? The dreary little cock was straining in its prison. I chuckled and brought him back to the chair to continue his makeover. The auburn wig wasn’t quite his colour, but he looked presentable from behind at least. The setting up of the camera took time, but at last we were ready as I got him on all fours….crawling around his office and shaking his plugged ass for me. I lifted the skirt and the base of the squat plug was firmly on show, along with the cock cage dangling uselessly in front.

The leather slave collar was buckled on and I led him around the office a few times. When I bent him over his desk, i made sure his cuffs were tight. He saw me take the strapon and step into it….i did it slowly and deliberately just to give him time to beg….but it wasn’t going to change my mind.

The camera was set and so was I……the plug would be removed and there would be no doubt, the little slag’s mascara would be running down his face….

TBC

Don’t leave!

Devious smile

Any chance of sharing more details about your shock collar training? I love the power disparity they represent; discipline at the push of a button.

Sure! I’m happy to share a bit more about the experience I teased.

It was some years ago, and it was the first night I was meeting and playing with a new partner. Generally I don’t recommend such intensity for a first session with a partner, but I’ll admit that I was young, dumb, and overeager. Nothing bad happened and it was a wonderful experience, but I would do it differently today... just to be safer.

Before any play, he showed me the collar shocking himself and then let me play with the collar and intensities of shocks on my leg and arm.

When I was satisfied and comfortable with the collar, he commanded me to strip for him.

He then bound my hands behind my back before locking the shock collar into place on my neck. The prongs were positioned on the side of my neck, which is usually more sensitive than the front of back.

He added another tie at my elbows, forcing a tight posture that thrust my chest forward. I was commanded to stand and spread my legs hip distance apart while he added a short hobble chain between my ankles.

And then the exercise began.

As I’ve shared before, I love strict power dynamics and protocol. Maybe even more so than the sex itself… and he knew that. He had me walk the length of the room, holding my perfect posture, but keeping my eyes downcast, as an obedient submissive would to not drawn attention to herself. He demanded graceful steps despite the hobble between my legs, no jerks from the bindings or chains, and absolutely no raising my gaze to his face.

He then sat on the sofa with the remote for the collar while I walked back and forth at his command. Every stumble, any time I looked up, or even a moment of less than perfect gait would be corrected with a shock.

As I found confidence in his asks, he would add more challenges. By the end, I was nipple clamped, gagged and had clamps hanging between my legs. Still holding my composure for him, still being corrected by a shock each time I didn’t meet his standards.

I was crying from frustration and pain, but so deep in subspace. Every shock reminded me that I was a plaything, his little pet, existing for his entertainment. And the only way to avoid the electric punishment was to exist as he demanded. I felt myself mold to meet his expectations in real time with the help of the collar. And I loved knowing how powerless I was to lash out, push back, or give attitude of any type.

I could be withering on the ground in pain as a repercussion for my bad behavior, while he barely even had to lift a finger. He would never break a sweat.

All that to say, it’s a treasured memory and one of the hottest things to ever happen to me ever in my whole fucking life.