Option 1

His hands dropped and he started to masturbate wildly!

There was a hum and his manacles slammed outwards, spreading him out.

The doors slid open and my boot swung through and up into his crotch.

He made a very loud noise as his balls made him aware of his bad decision.

I cuffed his hands behind him, and dragged him to my punishment area.

I laid him out, locked his head and shoulders to a low bench, stretched his arms out both sides, chained his cock to his collar, put his balls in a humbler, then had his legs up and hanging from a chain.

Cara stood over him, as I started to crop his balls.

I started to wave the crop, and got it closer until it started to tap-tap-tap on his captive balls.

He whinged at the pain.

That was quite clearly a TEST, bitch.

You failed!

SNAP!

His scream became muffled as Cara dropped her weight down on his face.

AAAGRMMMMMMMMHH

MMMMMMHHH

Cara slid her hands down the top of her rubber bustier, lifted her astounding tits out, and started to finger her nipples.

I moved around behind her, and rubbed her breasts myself, she responded by lifting her tits for me.

Her moans grew and grew.

Her moans of pleasure grew.

I lifted her off of him and let her decide on a punishment for him.

She recovered, and came back to help me with him.

We walked slowly around him, two attractive, scantily clad women, in heels walking, and regarding him with distaste.

She dropped to her knees by his head.

SO!

Five of the best?

He Stared at the ceiling in horror.

I wound up, and swung, as I started my swing Cara bent forwards and smothered his face with a breast.

SNAP!

UUUUUUURRRRMMMMMHHHH!!!

One!

SNAP!

AARGHMMMMMMMMMMMMM!!!

Two!

SNAP!

NNNNHHGGGRMH MHHH MHHH MHHH

Three!

SNAP!

MMMMHHHHMMHHMMHHMMHH

Four!

SNAP!

She lifted her tit for the last one!

MMMMMMAAAAAGGGGRRRRRHHHH AARGHHH AAHH NAAH NAH NAH NAAAWWRRGH AH AHH

Five! . . . Good bitch!

We got him sat up, then I presented him with his options.

Cara here gave me a punishment option after you gave her an orgasm, so that's probably going to be better than the one I'm thinking up.

So to simplify your choice you'll have to choose between me and her, without knowing what the punishment actually IS.

So...

YOURS, Mistress.

Mine?

You don't even know what it is.

It could be full castration for all you know, are you sure?

Yes Mistress, I made a mistake, I shouldn't have tried that, I deserve your punishment Mistress, I am yours.

My punishment was give you one orgasm and lock your cock up PERMANENTLY! . . . But now I want to play with you more, so how about some pain, pleasure, and I'll decide on how long you get locked up for, later?

Yes Mistress, Thank you Mistress.

We got him loose and when he turned he saw a pair of chains hanging down in a perfect position for him to be spread out, have a view of the city, get flogged, and still have enough space for his balls to get beaten black and blue!

He was quickly spread out and locked, with his balls pressed to glass that was over 4000 feet above sea level.

I my dildo rack folded out of the wall, I made my selection as I spoke.

When you signed the submissive contract, you agreed to obey me, you messed up, but then you made it a bit better, so the size of your cage is dependent on what you do next.

I'm just selecting a good cock to use on you, since pain needs some humiliation to go with it, doesn't it?

Yes Mistress.

Good boy.

Cara moved in and slapped a shock ring around the base of his cock and balls.

I strode up to him, and he started to beg for my cock, in an effort to lessen the next punishments.

I took a full face gag and pinned it to the glass, and he grabbed the ball in his teeth, and I pulled the straps closed.

The gag doubled as a basic VR headset, that covered his eyes and showed him only what I wanted him to see. What he could now see was me walking up behind him, with an ENORMOUS studded cock.

He didn't move, just whimpered in place.

My cock was made for intimidation, and upright pegging.

When in this position pegging became difficult, because of the angles and heights but this had a servo assisted system that would plunge this massive cock into an ass, just enough to do its job, but not enough to cause damage, and would only need a small amount of movement from me.

I touched the tip to his hole, and a whine escaped from him as he shivered.

I switched the cock to pain mode, and started to slowly screw him, getting faster and faster.

The cock excreted a lube down its length that worked like hot sauce, turning his rectal passage into the gates of hell.

His muffled screams were arousing, the inner pad of my strap on started to vibrate, and just before I climaxed pulled out, giving him the gel that nullified the pain lube.

I'm guessing that hurt him. Lets play something else.

We got him on his back, legs in the air, and spread.

One acupressure cock ring later and he couldn't get stiff with a bus load of sexy women.

So, I can give you this cage and we're done, I said holding up a cage of a decent size, or you can beg me for this tiny one, and I'll give you an orgasm.

Sooo...