Diary of a Penis Penitentiary Inmate

I don’t give my inmates er…victims, many freedoms. But, writing in a diary is one of them. Reading their thoughts and fears and about their time here sends exciting shivers up my spine and moistens my panties. Makes me want to take them and turn the tens unit up a bit higher to see a new reaction

—

I sit in my cell here in the penis penitentiary with no view to the outside, the cell is clean and utilitarian. My cock and ass hurt severly after today’s session with Ms Ivy. The day started in a pretty normal fashion. I havn’t cum in over a month now and each day, often multiple times a  day I have sessions with her…usually some light cbt or other forms of mild torture, but today my Mistress was in a particularly viscious mood….

I had never seen this room, the walls black, the lighting dim and tinged red. I was led by her minions, beautiful in their own right, but never the unimaginable beauty of Mistress Ivy, the warden, the gatekeeper of this hellish domain. Dressed in black leather bra’s and panties and long black leather boots with spiked heels they led me to the rack. For the most part it looked like a piece of gym equipment, chrome and black vinyl. They put me in the seat, like a partial stool, centered in it and chained my arms and legs to the chassis. Before me, a table of tools, devices and paraphenalia.

Mistress Ivy enters the room, dressed in a red leather corset and panties, black stockings, and thigh high red leather boots with 6 inch heels. Her long black hair falls over her shoulders widening her features. She has a demonic look as she says “Cindy, you have been a bad little stroker boy…we caught you on camera last night….stroking your cock without permission!”. She asks me to explain, but I just stutter, there is no excuse, I will be given no quarter and I deserve no such mercy.

She looks at me as her minions come up beside me. They begin to hold me and caress my cock and it hardens immediately. I know it’s wrong, but I can’t help it and the smile on Mistress Ivy’s face says something other than “enjoy it”. They begin stroking me, getting me rock hard. Then one of her minions take me in her mouth. The pleasure is amazing and I close my eyes only to be awakened by a sharp pain in my testicles. Mistress Ivy has just clipped a large metal clip to both testicles and each has a wire dangling from it with a hook. Her minion strokes and sucks me as Mistress Ivy starts applying weights to the hooks. The clips tug at my testicles and my cock leaks and I moan, but I don’t know if it’s pleasure or pain.

I continue to recieve the most amazing fellatio as Mistress Ivy brings a nylon rope over. It’s red and about 4 ft long and she begins tying it around the base of my cock and balls. She then puts a collar on me and clips the end of the rope to it. Her hand, her mouth, it feels so good and I lean back only to realize the trap. If my head leans back it tightens the knot around my cock, squeezing the balls up. I desperatly want to lean back and moan with pleasure, but know that I can’t.

Then I feel the wetness behind. Some type of lubrication, jell, or oil on my ass. I try to turn and see, but the rope tightens. Then I feel a cold metal object, rouded at the top begin to move around my asshole. It works it’s way in as I realize it is the other minion beginning to ass fuck me with a huge metal strap on. The other continuing to pleasure my cock as my ass rips apart receiving this massive pole. My mind wanders as I try to deal with all the sensation When a violent shock wave hits. The cock is electrified and it jolts me hard sending waves of pain through my ass. Mistress Ivy laughs loudly and I see she has the control for that. She adds more weight to the hooks dragging my testicles down.

I am torn with different emotions, massive pleasure, massive pain as I continue having my ass pounded from behind. But I feel myself coming to a climax and the minion sucks harder and harder and as I am about to explode my head jerks back reflexively, quickly tightening the rope and strangling my cock…The minion moves aside and Mistress Ivy steps forward clamping a gloved hand around my cock. She simultaneously presses the button and shock waves of pain shoot through my ass. The glove is freezing cold and has small but sharp spikes all over the palm and they prickle my cock. My head explodes with the multiple sources of pain and I know longer want to cum, I am demoralized, humiliated.

Mistress Ivy unbindes the chains and frees me from my torturous bonds. She looks at me as I slump to the floor, naked.. Well, you won’t be touching that little clitty of yours for a while will you Cindy…I hear her laughing as the minions drag me away, back to my cell. What does the future hold here in the Penis Penitentiary?