Option 2

He put his hands behind his head, and the doors slid open, he saw Cara standing with me and his hands dropped to his crotch.

I see you found a third path. UP!!

He lifted his hands and there was a click as his bracelets magnetized to the back of his collar.

I pushed a pre-lubed plug up his ass and led him to a bondage horse, sat him astride it, and put him into a box tie.

So, bitch wants to orgasm?

Yes, please Mistress.

Okay bitch.

A wheel of fortune appeared on the wall, divided up evenly except two stripes that were twice the thickness.

You know how this works: if it lands on "no orgasm" we do a "how long" wheel if it lands on "orgasm" you get a "what you have to do" wheel, if it lands on "CBT" Me and Cara stamp on your balls until we are tired, then we do the "how long" wheel and lock you back up, if it lands on "****" you get locked into an orgasm machine until you beg for mercy.

Let's roll!

It clicked round and teetered on the edge of "CBT" before clicking onto "orgasm".

He sighed in relief, as the next wheel started up.

Let's see what you'll have to do for it bitch.

It stopped on "endurance game".

I faced him.

So you get an orgasm, for winning this game, but if you loose you'll be having an orgasm anyway, so there are two penalty wheels I can spin for the length of your next chastity sentence one is short and maxes out at 6 months, the other starts at 6 months, and can go as high as 3 years, if you want the short one, I'll have to spin the handicap wheel, and you'll play with the handicap, whatever it is, okay bitch?

Yes Mistress, I'd like the handicap wheel, please Mistress.

Good! so here's the game: Cara will kneel in front of you, with your cock resting on her breasts, she'll play with your balls while your butt plug tries to bring you to orgasm, I'm going to watch and you have to beg me for permission to cum, if you cum without permission you get punished, and your chastity sentence gets doubled! Clear?

Yes Mistress.

The clicking started.

So bitch, how long will you be locked up for?

Click . . . click . . . CLONK!

4 Months!

And your handicap:

CLONK.

Class 4 Gag.

Cara strode off to get the required item, as he looked uncertain, and about to protest.

You CAN decide not to have the handicap, but you WILL have to take the FULL penalty from the other wheel, and if you loose the game that STILL doubles, and you'll have to say goodbye to your orgasms for SIX YEARS, with the gag you may fail and have 8 months, but without it, you'll have 3 years for certain.

Cara returned and stood behind him with the gag.

So?

To Gag, or not to Gag, that is the question?

He, nodded and Cara flipped the gag she was holding over his face, and pulled the straps together, they clicked in and the gag adjusted itself to his head.

She stripped to her corset and shoes, then moved round and knelt in front of him, taking his cock and resting it between her breasts, she placed her fingertips on his balls and coaxed him into a full, throbbing erection.

Oh that gag should probably be fully activated before we start.

I snapped my fingers and the gag belts expanded and it became a full sensory deprivation hood.

Watch this, I said to Cara, DOES BITCH WANT TO CUM?

His head twisted slightly, as he tried to get some light or sound, but no response.

DOES BITCH WANT TO SCREW HIS MISTRESS?

...

Nothing

And now . . . BITCH? YOU HAVE PERMISSION TO CUM!!

Cara looked puzzled.

I'm cruel, not evil! But if I get ANY bitch behaviour from you, I WILL flog your ass, and chain you to a seat.

She nodded, wide-eyed, and her stroking resumed!

With a thought, I activated the plug, and it hummed to life.

A chain dropped from the ceiling, and I connected it to his restraints between his shoulder blades, then it lifted him slightly.

His muffled moans became muffled screams, and what could be **** pleas for permission to cum.

I smiled, He'll hold it as long as possible anyway, I'll be able to decide later on what I tell him, and how long he is locked up for.

Cara smiled, and continued to rub his balls.

His yells reached fever pitch and he gave up with a resigned cry as his cock jumped.

I slammed my hand down and pushed his cock down between her tits, and it recoiled like a cannon, and cum spouted out like a geyser, and up toward her throat.

The twitching continued.

I sent her instructions on what to do next, after he was done.

When he'd stopped twitching, we moved together, his gag retracted, she stood and pulled her corset off, he watched as I scooped a load of his cum out from between her tits with a gloved hand, she spun on her heel and bent forward, and I slapped it all between her ass cheeks, she stood, and then all his manacles de-magnetised.

He hesitated.

Go on, bitch!

He leapt off, dropped to his knees, and pushed his face into her ass.

She arched her back into it, spreading her cheeks for him.

When he was done, she gave him her tits to clean, and he pushed his face in eagerly and thoroughly licked her cleavage, breasts, and nipples.

I sat on a sofa, placed his chastity device on the coffee table in front of me, and a tea was served to me in a cup and saucer, by robot, and I sat and waited.

Eventually Cara led him to me on a leash.

Now about your future chastity sentence . . . .