Chapter 2

Jennifer had lost track of time - lost in the darkness of her blindfold, and the silence imposed by her ear plugs, time slowed to a crawl. The van was nearing the conclusion of its 4 hour drive to the coastline, making a beeline to the port, where a government sanctioned prison ship would haul her away southward.

The gentle clanking of her breast weights swinging into to each other accompanied the conversation of her captors, sitting comfortably in their chairs drinking cold beers, trying to pass the time. They weren’t technically permitted to harass their prisoner in transit, but occasionally one would avail himself of her charms, groping her heart shaped ass and running their hands over her strap-split pussy lips.

The particularly sadistic guard who had clipped her nipples would periodically remove the painful clamps, pinching the blood back into the abused lust-nuggets to restore her sensation. It was a brief respite, if you could call it that, as the clamps would be promptly replaced to the accompanying groans from the wretched woman. All the while she slowly built up to another orgasm, the vibrator in her cunt occasionally wresting a cum from her poor, overstimulated pussy.

Finally, at about 9pm, the van quietly pulled into one of many large warehouses lining the seaport. The large, metal overhead door closed behind them, as the van shut off its headlights. “Captain” Anderson briskly walked towards the van accompanied by three other guards, expecting his new charge. He was a member of Vigilant Securities, a private security contractor unofficially employed by the government to operate St. Damian island’s prison compound. Strictly speaking, the facility didn’t exist, its inmates made up entirely of females guilty of treason, terrorism, and other high crimes.

Flinging the van doors open, one of the TSA guards accompanying Jennifer stepped forwards, handing the captain a stack of documents.

“Here she is sir, Jennifer Carter, apprehended just a few hours ago.”

Flipping through her paperwork, Captain Anderson stopped at a note from Doctor Peterson, his eyebrow raising.

“Hmm. Her medical file says she is lactating and must be milked before transport. Apparently, and I quote, it’s dangerous to go so long unexpressed. What an interesting requisite.” Jennifer shifted uncomfortably, unable to hear their conversation but aware of the stillness of the van. Crouching down, eyeing the straining globes, the captain lifted first one, then the other weighted cylinder, removing them from her breast cuffs.

Jennifer moaned into her gag, the relief washing over her. Her titties still ached horribly, but at least they weren’t being dragged down anymore. “Peters” snapped the captain “we will take care of this here. Go find a bucket and bring it here.”

The guard briskly set off to his task, and the captain continued prepping her. Pulling off the bulldog binder clips affixed to her swollen teats, droplets of milk immediately formed at their tips. He flicked these a few times, enamored with the hard points, and rolled them between his fingers. Restraining himself, he then removed her breast cuffs, letting her heavy boobs finally hang unencumbered for the first time in hours. Gently cupping them, he could feel a slight hardness to them, the bluish veins just visible beneath the skin made more prominent by the over-full milk ducts within.

Jennifer visibly recoiled at the intimate touch, squirming and trying to wiggle her dangling globes from his hands “Make a note in her file, one demerit for non-compliance” spoke the captain softly.

Moments later, with an old empty 5 gallon bucket placed under her dangling teats, her much needed milking began. Gripping her nipples roughly, he gave them a few warm up pinches before beginning to milk her like a cow, alternating pulling down on her nipples, left and then right. Immediately a fine spray of milk shot forth into the bucket. Jennifer immediately blushed all the way to her neck, humiliated that a stranger was treating her like a farm animal. Besides, this milk was for her baby, something precious between a mother and child. She was outraged something so beautiful could be used against her like this.

No matter how Jennifer personally felt about the matter, her milky mammaries did start to feel better, as the inexorable pressure in them lessened. Anderson smiled, enjoying the past time, comically wondering if he should go into ranching.

As her stream began to lessen somewhat, he released her nipples and gripped her heavy boobs in an ironlike grip. Gasping at the sudden pain, the young mommy found her boobs being yanked down and up roughly, the tendons in Anderson’s arms visible as he did his best to wring the last of her motherly bounty from her. Her perfectly shaped ass wiggled sexily as she tried to cope, giving everyone present a tantalizing show.

“I’ll hold her Captain” the guard named Peters volunteered helpfully. Pushing the tight strap running between her legs aside, he jammed his thick thumb up her ass while gripping one full cheek in his hand. Unsurprisingly, this did not actually help to stop her wiggling, and the vibrator, still buzzing in her fuckbox, started to push her closer to yet another orgasm.

Moaning into her gag, Jennifer wanted to die from humiliation as she started to clamp down on the vibrator, her brain confusingly mixing the signals of pain from her forced milking and the pleasure between her legs.

*Whistle “I think the bitch is cumming captain!”

Scowling, Anderson yanked down on both titties hard and held them there, twisting his hands and flexing his fingers to get the last of her milk. She sobbed as the tremors wracked her nubile body. “Add that to her demerits.”

The captain released her breasts and stood up, wiping the bit of milk he got on his hands in her hair. “That’s about all I can get by hand. Let’s get her processed and loaded. First though, the slut looks thirsty.” He reached down and unbuckled her gag, pulling out the rag in her mouth in the process.

“... -who do you think you are? I’m innocent, please I’m being framed!”

Suddenly finding her hands released from the wall of the van, she was pulled upright while her head was yanked backwards. One of the guards stepped forwards and pinched her nipples with jagged fingernails.

“ouch! Ow -!MMM!”

As soon as her mouth opened, a funnel was jammed between her pink lips, her soft mouth forming a near-perfect O on the shaft as she struggled against her captors.

Upturning her milk bucket over the funnel, she immediately started coughing and spluttering as she immediately deduced what was being poured into her mouth. Forced to swallow a large amount of her own milk so that she could breathe, the overflow in the funnel spilled over her face and ran down her chest and stomach to drip onto the floor messily.

gasp cough “stop ... how dare - mm!” Her chest rapidly rose and fell as she caught her breath, only to have her rag and ball gag shoved back in. Only her rag tasted different now, it being used to wipe up her milk off the dirty floor.

“Let’s get her aboard, boys. And note another demerit for disrespect.”

Designation: Prison Ship MV Deering Size: 250 feet Destination: Tropical Island Prison of St. Damian

The ironclad MS Deering crested another wave, flinging the foamy spray into the air as it chugged along southward. Property of Vigilant Securities, the transport was a repurposed merchant vessel, and was used to move prisoners and cargo to and from St. Damian Isle.

In the non-air conditioned cargo hold, the difference between prisoners and cargo was not so clear, Jennifer soon discovered. Not given the space to stand, she sat on her knees in the corner of her too small cage, one of fifty occupied by women in various stages of undress. All of them were deafened by ear plugs and blindfolded, Vigilant Securities seeing no benefit to giving them clues as to their destination. The entire operation, even the prison facility itself, were officially denied existence by the government, making it nearly impossible to locate someone once they disappeared here.

The trip was a five day journey, and the prisoners were currently being assigned their identification numbers. Jennifer could not see her surroundings, but was just glad her vibrator had been removed. Unfortunately the thin black strap splitting her protesting love lips apart remained, as did her black strap-on heels. That was the only ‘clothing’ she was afforded, her bare, sweaty torso glistening in the light of the overhead lamps.

With the gentle swaying of the ship and the smell of the sea back at port, she guessed she was on a ship. ‘Where are they taking me?’ she wondered. ‘Is it still in the country?’

Suddenly being pulled from her cage, she was held firmly in place by her elbow and wrist-cuffed arms.

Yanking her earplugs out, the guards addressed her.

“Jennifer Carter, arrested terrorist, apprehended yesterday. Your new identification is Prisoner 174. Nod if you understand.”

Hesitating, but deciding not to provoke them while so helpless, she nodded.

“Good. You are in transit to a more secure facility, and you will have a greater degree of mobility once we arrive. Until then, you will be kept partially restrained and are expected to behave.”

Glancing at a clipboard, he continued.

“Oh my. It seems you’ve already received three demerits from our officers.” He gently tapped the clipboard with his pen, a small smile forming in the corner of his mouth.

“mm! Ammm mmm emmgrr!” Jennifer tried to protest her innocence through her gag, failing utterly.

“Yes, I see your point” the man mocked. “A few of your fellow prisoners already have demerits as well, but no one else has three. You will serve bow-side duty nightly for the remainder of the trip.” He pushed her earplugs back in, finished speaking with her.

Still being held firmly in place, she didn’t even see the red hot brand coming. Pushing it into the side of her neck, her flesh sizzled as she screamed, fighting against the guards holding her with all her might. The burly guards were simply too strong, outmuscling her convulsions. A moment later, the brand was removed, revealing a bright red burn, emblazoning the number 174 on her body forever.

Crying and weeping into her gag, she was shoved back into her tiny cage. Jennifer pulled her knees up to her chest, the closest she could get to hugging her knees. This wasn’t a ship, this was a ferry to the gates of hell.

Moving along to the next cage, a pretty redhead was pulled out. Continuing their dreadful duties, she too ended up branded, crying, and re-caged. In all over 25 women were processed, all ready and waiting to join the population of St. Damian’s prison.

Evening fell and Jennifer really, really had to pee. She had discovered a waste bucket in her cell, but refused to use it. Besides, how was she supposed to pee with this damn strap running between her legs, rubbing her most intimate flesh raw.

Her neck still hurt from her branding, but it was slowly giving way to a painful tingling. As long as nothing touched it, she could bear it.

It was time to feed the prisoners for the night, so the guards visited their charges again, pulling the gags from their mouths through the cages. A cacophony of yelling and crying assaulted their ears as the prisoners found they could now voice their outrage, but it made little difference. They couldn’t hear each other through their earplugs anyway, so talking was pointless. Most eventually gave up their shouting.