Chapter 3

Jennifer, aka Prisoner 174, squinted into the sunlight beating into her gagged face, as she made her way down the loading ramp of the prison ship MV Deering. She was trying to make out the features of the island through the glare, her blonde hair blowing into her face, when she was yanked forward another step by the woman she was chained to in front of her.

Unfairly framed for terrorism solely for her attractiveness and perfect, fuckable body, the dejected young mother had spent the last few days chained to the ship’s bow, her tits bound and skewered by thin needles, a tight crotch strap splitting her labia, as her suffering girlflesh led the way to St. Damian’s high security prison. It was a small tropical island managed by the Vigilant Securities company, a secret location where women accused of ‘high crimes’ were sent to disappear.

Above the noise of the birds and cicadas, Jennifer could barely make out the sound of hammering, and a woman crying out far away. Wonder and panic gripped her heart, but she didn’t have too much time to dwell on it; as the redheaded woman in front of her was unshackled and led away, Jennifer found herself face to face with a fat officer sitting at a desk set up at the end of the loading ramp, flanked by guards.

“Wait, there’s been a mistake! This can’t be happe-...” the redhead’s voice grew quieter and quieter as she was led into a cinderblock building behind the desk, being drug down the hall by her escort.

Drawing on a fat cigar, the man eyed Jennifer’s naked figure up and down, and peered at the small number 174 branded on her neck.

“174, let’s see here ... ah, so you were the charming woman I saw hanging on the ship when it came in. I can see why you were chosen, you certainly have ... abundant qualifications for such a position.” His eyes glinted as he stared at her abused breastflesh, still sore and reddened. Jennifer felt her anger rising.

“We are not a luxury hotel here. You lot are guilty of the worst crimes possible, and will work every day for your keep. Today you will be processed through our medical facility, and when given a clean bill of health will be escorted to your cell. Take her.”

Two guards stepped forward, and harshly pulled her gag from her mouth. Moving her aching jaw, she decided to remain silent for the moment, not relishing the idea of losing her ability to speak again. She was unchained from the woman behind her, and marched by the two guards into the large, imposing cinderblock building she saw earlier.

Hobbling down the dark hall in only a pair of heels, Jennifer was already sweating from the combination of humidity and fear. Lining the hall were heavy looking steel doors. She would later learn these dozens of rooms were where guards could bring ‘misbehaving’ inmates for corrective instruction. Voices could be heard as she passed a few of them.

“ ... No! No no please! I’ll work harder! I’ll work- CRACK Ahh!!!” CRACK Was that a whip? Jennifer’s face blanched.

More voices and gagging noises “That’s it bitch, suck harder!” Gasp “Please, let me rest! I’m so tired...”slap The door was left wide open, and Jennifer could see the backside of a filthy, bruised woman on her knees as a large, black guard pistoned in and out of her overworked throat, holding her hair tightly in his hand. There was a line of at least 10 men behind him.

Coming up to a set of double doors on her left, Jennifer and her escort finally arrived at medical. A doctor in a long white coat glanced up at her, and gestured towards the gynecological chair. Her two captors manhandled her into the stirrups, locking her down.

Not saying a word, Doctor Ray sat down on the stool between her legs with a clipboard.

“Um...” she began. “what are you going to do?”

Totally ignoring her, the doctor peered at her cunt, a few days of stubble visible since her shaving at the airport. Making a few notes, he set down his clipboard and picked up a stainless speculum.

Roughly pushing it into her pink hole, he cranked it open. Jennifer shut her eyes and breathed as she felt her dry walls opening up. It became uncomfortable, but not painful, as she was spread open for his view.

“ugh! God damn it ... why the fuck do you need to see there...” Jennifer muttered quietly, embarrassed. She was still afraid of being gagged again, so she kept her voice low as she complained to herself.

Shining a penlight up into her, the doctor peered up her tight little tube. Returning to his clipboard, he notated her healthy coloration and lack of any signs of abnormalities or diseases.

Taking a long swab, he collected a pap smear from her cervix, sealing it away in a small bag, before closing the speculum and withdrawing it from her. Standing up, he roughly pushes on her abdomen, feeling her stomach and uterus, then pushes his thumbs down over where her ovaries lay. Digging in deeper, Jennifer inhaled in pain, until he finally stopped and made more notes.

“Are you done now?” she asked him, getting fed up with all the abuse she had been made to suffer lately.

He looked her in the face, emotionless, then suddenly slapped her hard, her head snapping to the left. “AH! Fuck!” SLAP. He battered her face the other direction. Nodding at the guards, one of them stepped forward and slammed his nightstick into her sore, upthrust tits, Jennifer’s cry accompanying the sick thud as it sank into her bosom.

Message received, Jennifer shut her mouth and stopped talking, a trickle of blood leaking from the corner of her lips.

The doctor picked up a large, empty syringe, and inserted the sharp point into a vein in Jennifer’s arm as she watched him fearfully. He slowly filled the entire syringe with her crimson blood, then withdrew it. Labeling it with the date and “174,” he set it aside for screening later.

Hefting her punished mammaries in his cold, latex-clad hands, he looked closely at the small puncture wounds inflicted by the thin needles that skewered her each night from her time on the MV Deering. With a sanitation pad he wiped away the small amount of blood leaking anew from the tiny holes, coaxed out by her recent disciplinary action. Jennifer found it appalling and ridiculous that the man who just ordered her breasts battered with a nightstick would suddenly have concern for their health, but remained silent as she glared at him.

Noting on his clipboard that her wounds were minor and would heal with no markings, he next took a large pair of calipers and began measuring the size of her breasts. All angles were measured and noted, width, length, and height.

“They’re Ds, you could have just asked you know...” she mumbled, not looking the doctor in the eye. The doctor then grabbed her right nipple and pulled up hard, stretching her breast into a cone as far as it would go as Jennifer winced and arched her back. He quickly measured the length from chest wall to nipple tip, then repeated the process on her other breast, tugging roughly to make sure there wasn’t any slack. She exhaled when he finally released her, her hefty tits wobbling back into shape.

Satisfied, he walked to a nearby cabinet and rummaged around in it. When he returned, Jennifer’s eyes widened.

In his hands the doctor held a large, 2.5 inch diameter flexible dildo. Along its entire length on one side were graduations every sixteenth of an inch; a monster of a dildo meant to measure her depth!

Sitting between her shapely thighs once again, the cold, but at least lubricated, dildo began to be pushed into her narrow little box. The tapered end was manageably sized at an inch, but the head quickly flared wider and wider until it hit the full 2.5 inch width.

Jennifer grunted and ground her teeth, as she felt her entrance widening around the smooth monster. She could survive this, the big guard’s fist at the airport was bigger after all.

Such thoughts however did not do much to comfort her. As first one, then two inches sank into her, Jennifer moaned as her tight pussy stretched around the full girth, the diameter of the dildo the same as a coke can. She could feel the little bumps from the graduations marking the measurements, as the slippery artificial cock wormed its way even further into her, the doctor’s hand pushing with a constant, steady pressure.

Not giving her time to adjust, 3, then 4 inches were inside of her. “Ohhh ... too fast. NGH!” She jerked as the fifth inch was cruelly shoved up into her in reply, her muscles intimately and wetly wrapping around the cylinder in a squeezing embrace, a drop of lube running down her right labia.

The doctor withdrew the dildo 2 inches, then pushed forward again while twisting it. The fake cock pushed forward in a screw-like motion, while Jennifer’s thighs began to tremble. Stopping at 7 inches, the doctor knew she could take more. It’s amazing how much a woman’s pussy can stretch, especially when aroused (of which she was not). He just needed to work her up to it.

The doctor, however, had many inmates to evaluate today and couldn’t afford to wait for her biology to keep up. With the palm of his hand, he battered the base of the dildo hard, hammering it forward another half inch!

“Ah! UGH! Sto--” thud thud “NGH! Ohh...” Jennifer grit her teeth between her yelps, her tender quim straining to meet the demands placed upon it.

Now at a good nine and a half inches, the doctor twists the dildo again so he can see the measurements. Picking up a small rubber mallet, he starts tapping the dildo in with short, firm strokes.

Jennifer’s eyes squint as she bites her lower lip, trying to not cry out too loudly, fearful of the guards’ reprisal. She can feel her cervix pushing upwards, as the entrance to her womb deforms to make way for the coke can sized invader. Finally, the doctor is satisfied he can’t possibly get anymore into her without serious injury.

Jennifer, no, Prisoner 174, lay there feeling the throbbing between her thighs, legs futilely flexing against the stirrups. She felt so full, she would have done anything at that moment to have the aching dildo removed. The barest hint of a smile crossed the doctor’s face as he notated her final measurement: 10-5/8 inches. He had never seen someone get so close to 11 inches before.

“Thank you 174” the doctor began speaking, as he pulled his measuring apparatus from the gasping woman’s sore twat, twisting it to help work it free as her muscles clamped down on it. “We will have more data to record later this week, but that is all we need from you today.”

When her legs and arms are released, Jennifer tries to curl up in a ball for a moment but is instantly hauled to her feet by the two guards, gripping her arms tightly as they handcuff her wrists behind her back. On her way out the door, she is passed by the next inmate to receive her introductory medical evaluation; a very beautiful, very heavily pregnant black-haired woman, with a small number 180 branded on her neck. She must have angered her escort, as three bright red welts decorated her otherwise blemishless baby bump, tears leaking from the corners of her eyes as she sniffled. Other than her apparent heavy pregnancy, she appeared to be quite fit and trim, and Jennifer was sure she surely must have had an hourglass figure before.

The woman’s name was Mikaela, and as she hobbled along in her high heels trying to keep pace with the guards, she briefly caught Jennifer’s doleful gaze. Who knew what atrocities awaited her expectant body at the hands of the doctor?

Jennifer, having finished her medical evaluation, was hauled to another prison compound building. Housed in Block 4, her cell was one of many which shared a common area. When released from their cells in the morning, all the prisoners would be gathered there for their morning duties and receive their daily assignments.

Today was a special schedule as the ship had arrived today with new inmates; a meeting was being gathered right now in Block 4. Jennifer was the last to arrive, and as she was pushed through the circle of guards she was forced to her knees next to a wooden post anchored to the ground. Bolted to this post was a chain leading to a black leather collar, which was tightly buckled around Jennifer’s neck, making it difficult for her to swallow. Nine other posts were spaced in the center of the room, each with a pretty, and stark naked, girl chained to it.

All of them looked tired and utterly defeated.

“Sluts!” barked a stout, angry looking man. “We have 3 new additions to our Block today! As such, I will be going over our rules here at St. Damian’s facility! Consider this a friendly reminder for those of you who have been with us for some time!”

Jennifer did not like where this was going.

“I am Sergeant Callow! I AM Block 4. You worthless pieces of fuckmeat are here because you are the dregs of society! Each of you are guilty of unspeakable crimes. Do NOT bother protesting your innocence to us! I assure you, we have heard it all before. You will not be pardoned. You will not EVER be released.”

“What you will do is work, work and be punished! Society has demanded repercussions for stupid, fucked up bitches like you. The death penalty is too kind for you lot, and this facility isn’t a hotel.”

Jennifer really, really didn’t like where this was going. Her face started to turn white as she realized the hell she was in for.

“Every morning, your handlers will assemble you here, in the common area, for your morning strapping. This is a non-negotiable daily punishment, a way for you to attempt penance for your crimes! You will receive at LEAST 20 strokes to the breasts, and 10 to the cunt! The count, and instrument used, will vary depending on your behavior the day before! So don’t fuck up!”

Most of the women simply looked down, clearly used to such terms. The 3 newcomers, including Jennifer, sat with their mouths agape, disbelief etched on their faces.

“What kind of fucking prison is this? You can’t just - AGHGHH!” Prisoner 177 screamed as a guard tasered her right breast, sending her into convulsions for her outburst. A second man grabbed her cuffed wrists tightly and yanked the brunette’s hair back, as the first guard forcefully laid into her C-cup tits with an open palm, right onto her nipples.

*SLAP! “AHH STOP!”

SLAP! “Shut up, whore!” SLAP! “NGHH” SLAP! SLAP!

“Stop, I can’t ... I can’t!...! AH!” SLAP! Jennifer could almost feel the blows across the room, the woman’s breasts absorbing the impacts as they wobbled, being alternately slapped left, then right. “It will stop when you learn to be silent!” SLAP! SLAP! SLAP!

As 177 received the fruits of her backtalk, the Sergeant cleared his throat.

“As I was saying! Don’t fuck up!” SLAP! “nghh!” SLAP! “Following your morning punishments, your assignments for the day will be given.” *SLAP! “There is no shortage of work to be done here; hard labor will occupy most of your days! But there are other duties as well. You will perform whatever is required of you or face harsh punishment!”

“Everyday, after work, you will be given dinner and returned here for showers. Any additional duties will be carried out, and sometimes an additional punishment, depending on my mood and if I feel more chastisement would help you in your search for repentance. You will be retired to your cell, awaiting the new dawn and the pleasures it brings! So goodnight, my dear little fucksluts! I look forward to us starting off on the right foot tomorrow morning!”

Sergeant Callow finished his little impromptu speech, and Prisoner 177 was doing her utmost to not let out a squeak, and failing, as her swelling tits continued to receive their beating. The second guard was now standing behind her, holding her boobs up by her nipples as the first slammed his nightstick into the undersides, trying his best to crack a rib through her fat, bashed sacks.

Jennifer and the other girls were released from their collars, and led to their individual cells. She was thrown to the floor, her hands still cuffed behind her, and heels tightly strapped to her feet. She stood up warily and regarded her cell; it was bare and simple, with a concrete floor, bare metal bed with no cushions, blanket, or pillow, and no toilet or other amenities of any kind.

Her stomach growled and she sat on her metal bed, starting to cry and let out all the day’s pent-up sorrows. Her mind wandered to her husband and baby boy, and as she thought of them she listened to the jeering of the guards as Prisoner 177 begged.

“Please! Please leave my breasts alone! I can’t be quiet, not when you’re beating me so hard! Please!” she wheezed.

A loud, resounding whack echoed through Block 4 in response, followed by a sickening crack and a heartrending wail.

Still in the medical lab, Mikaela choked and swallowed as the long, thin cock spurted yet another load in her mouth. Her head was in Doctor Ray’s lap as he sat on a floor cushion, her long raven tresses hiding his crossed legs from view.

She had never been in so much torment in her life. Her upper torso was wrenched back painfully far, almost to the point of damaging her spine, as the doctor’s long cock fed her her dinner while her tits supported her weight on the floor. Two short, heavy duty elastic straps ran from around her shoulders and armpits to a belt around her waist, helping her maintain her severely arched position. Her heavy, pregnant belly was pressed up against the wall, and her ankles secured to mounted wall manacles, spreading her legs wide open 180 degrees to her body.

Doctor Ray had immediately postponed evaluating the new inmates until tomorrow after he saw her, a grin creeping onto his nearly always emotionless face. He had a thing for pregnant women, especially pretty ones, punishing them for their whorish past. Mikaela, or Prisoner 180, would not be getting much sleep tonight. Or in the foreseeable future for that matter.

Promising her he would induce a painful and bloody abortion of her baby before killing her if he so much as suspected she wanted to bite or disobey him, he set about mounting her upside down to his wall in her current predicament, and ordered her to suck his cock.

Aside from the tight straps arching her unnaturally backwards, he had various other tools and toys wreaking havoc on her nubile, fertile body. Her heavy knockers, sore by default from her pregnancy and currently supporting her body weight on the floor, had two wired, bare copper rings tightened around their bases. Two copper plates were mounted to the floor underneath her crushed nipples, and he had a constant, 120 volt low amperage current flowing from the rings to the plates, electrifying the whore’s mammaries just below the point of electrical burn.

He had just come into her mouth for the second time as she sucked him off, and she coughed and moaned in pain into his softening cock. He would simply keep it there in her mouth, until her pain and suckling got him hard again, and he could try to blow yet another load into her hot fuckmouth. In the meantime, he gazed upwards at the beautiful artwork he had achieved.

A simple, but effective 6 inch wide leather strap wrapped around the girls lower back, and anchored her to the wall. Reaching up, he tightened the strap further, and Mikaela groaned into his cock, weeping, as yet more pressure pushed her large, pregnant stomach into the stone wall even harder. The pressure in her womb grew, and through the shooting pains she felt her baby kick in annoyance.

Farther up the wall, a large, inflatable dildo was mounted on a piston, a piston which was currently pumping down into her splayed twat with forceful thrusts. A heavy springed, toothed clamp bit fiercely into each labia, with twine running from the clamps to tie around her spread thighs, pulling the gates of her pussy open, the labia blanched white from the strain. He took another little blue pill and, satisfied she was taking the 2.5 inch dildo rather well, he punched a button on his remote and heard the little air pump kick to life, expanding her artificial lover up to 2.75 inches.

A tear rolled down the expectant mother’s cheek as she felt the bulbous dildo grow even more, punching down into her cervix, as if knocking on the baby’s door. She couldn’t tell what hurt more, her wrenched back, the infernal strap crushing her abdomen to the wall, or the stretching, biting pain in her pussy.

She wasn’t even really sure how she got here. She was actually an important business woman for a wealthy company, used to a life of luxury, and about to start a family with her husband. All that changed though when she flat out refused the CEO’s advances, insulting the man right to his face and humiliating him. She was kidnapped in the middle of the night by paid thugs, who drugged her, and she woke up on the MV Deering prison ship, in-bound to St. Damian’s island, condemned on false charges.

She snapped out of her reverie, the dildo growing another quarter inch, her pussy squelching wetly as it took the massive 3 inch wide dildo. She squealed and cried into his hardening cock, and knew if he kept it up she would be torn.

The doctor knew that too. He was a doctor after all. He would keep the little bitch at 3 inches for a few hours, but wouldn’t stretch her anymore. She could probably go to nearly 3.75 inches if he was careful, but no need to ruin her cunt so early yet, he just got her. He smiled as he watched her tight, suffering pussy grasp at the invader, her lips pulled even wider than the rest of her slutty fucktube.

“I believe you’re supposed to be doing something with that mouth, you stupid slut. Or did you forget our arrangement?”

Steeling herself, she again started working her mouth, running her tongue along the bottom of his shaft, gagging as the cock grew and finally touched the back of her throat. God her breasts ached horribly ... she could barely think straight, the current relentlessly flowing through her titflesh. The tendons in her thighs screamed at her too, threatening to dislocate her hips if she continued to ignore them.

Finally, late in the night, the evil little man leant back and fell asleep on the floor, keeping his soft cock in her warm mouth. As she cried and breathed on his cock, still hung up in her painful bondage as she was relentlessly fucked, he dreamt of the things he would do to her tomorrow.

A loud, clarion call rang through Block 4. Before Jennifer could even rub her eyes, her cell door bust open, and her two handlers were standing over her. Each grabbing a breast in a strong grip, they hauled her to her feet and drug her to her post in the common area.

“Morning sluts” greeted Sergeant Callow, as all the women were promptly put into position, their chained collars clicking around their necks, tethering them to the posts. Their hands cuffed behind their backs thrust their breasts out nicely.

Even Prisoner 177, the woman beaten yesterday for backtalk, was present, Jennifer noticing with dismay her swollen, bruised purple tits. The guards had used a nightstick to tenderize her titties to the point of cracking one of her ribs - and not even she would be spared the morning strapping, the additional torment a further motivation to stay in line. She sobbed quietly, awaiting the coming pain.

The handlers lined up next to their charges, each holding a supple 1.5 inch wide thick leather strap. They dripped with oil and looked heavy in their hands. Then, a simple command.

“Begin.”

THWACK! THWACK! THWACK! THWACK! THWACK! THWACK! THWACK! THWACK! THWACK! THWACK!

Ten thunderous thwacks echoed throughout the room, as 10 bare-breasted women grunted and groaned. The thick straps struck heavily, leaving a deep red mark behind. Prisoner 177 actually screamed with each blow, unable to contain herself.

Jennifer gasped and twisted miserably in her bondage as blow after blow rained down on her boobs. Left boob, right boob, top, bottom, both nipples, the handlers showed no mercy to her tits. They were obligated to get 20 lashes from the strap each morning, and 20 lashes they would receive.

THWACK! “Ungh” THWACK! “ngh.” THWACK! “ ... fuck!” THWACK! “Ngh!”

As the steady beat of the breast drums continued, Jennifer’s sore titties danced and jiggled across her chest, absorbing countless pounds of kinetic energy. She couldn’t help but moan.

Finally all 20 blows had been given. A modest number of strokes. Less than 2 seconds after the final stinging blow to her funbags, Jennifer was spun around to face the post and Splat! the strap whipped up harshly between her slightly spread thighs, kissing her cunt with a fiery kiss that left her breathless! Splat! “!? gasp!” Splat! “Ungh!!!” Splat! “ohhh ohh...” Splat! Splat! Splat!

“You’d best keep ‘em spread ladies, or it will be hell to pay later!” declared the Sergeant, eyeing his charges carefully. Prisoner 177 actually looked relieved during her cunt whipping, pleased her tortured painsacks weren’t being subjected to further abuse.

Splat! “ugh!” Jennifer couldn’t believe the pain between her legs, it was all she could do to stay conscious. Just two more... Splat! “Nnnnnngh!!!” One more. One more. One m- *SPLAT! “NNGH God ow owww owwww” the guard had given her the final stroke with a flourish, sending a particularly strong armed swing straight up to envelop her cunt. Jennifer hopped around in place, her legs snapping together now that the strapping was over.

“Better than I expected, sluts! Maybe I need to tell my men to stop being so soft with you! Your handlers have your assignments, and you have 1 minute to use the bathroom, I suggest you all hurry.”

With that, Jennifer was abruptly unchained from her collar, and hauled off by her two handlers to Block 4’s community bathroom. Freeing their hands, the veteran women practically ran to the toilets, not having been able to relieve themselves since yesterday afternoon.

Jennifer sat on a toilet and did her business, while her two handlers stood in front of her, watching her every move. She blushed deeply as she dabbed her pussy with the toilet paper, not sure why she still got so embarrassed when these people had just violently strapped her pussy and breasts.

Standing at the sink to wash her hands, Jennifer suddenly felt her legs kicked apart as her torso was shoved down, a hand spreading her labia from behind. Suddenly she squealed, as one of her handlers had shoved a shiny urethral plug straight up her tiny, burning peehole, the little handle poking out.

“You will not be permitted to remove that plug until this evening. If you do, we will hurt you. A lot.” said the grinning guard.

“What? Why? No one else has one!” the blonde protested indignantly, as the second guard cuffed her hands again behind her.

“Because I say you have to, that’s why!” the guard was no longer grinning. Pinching her nipples in both his hands, he twisted them until Jennifer’s eyes started to well up, a little white droplet forming at the tips. He smirked. “We know you’re full of milk, it was in your file. Some of these girls start the day cooking in the kitchens, some clean the bathrooms or offices, and some go straight to hard labor outside.” As he talked, he kept tweaking her hard nubbins as she winced.

“Your first task each day, cow, will be to report to the kitchens for milking. Your milk will be used in the preparation of our meals. After your milking, we will take you outside. You are going to work the gravel carts until we tell you to stop.”

The heat in the kitchens was unbearable. Not only was the room not air conditioned, on a tropical island near the equator, but huge cooking hearths flared up and burned as naked prisoners rushed to and fro, working hard to meet their quotas and feed the island’s population.

Sweat dripped off of Jennifer’s teat tips, and her whole body glistened in the heat. She was secured on top of a wooden ‘horse’, a long, sharp edged pyramid-like mount that bit into her sex. She was one among another 30 women, all lined up in rows and unable to speak, their mouths stuffed with ball gags. Her legs were doubled up and shackled to the sides of the horse, forcing her to put all her weight on her sore cunt, and she did her best not to move too much. Her neck was also collared and shackled to the top of the horse with a short chain, forcing her to lean forwards deeply, each of her breasts hanging downwards heavily on each side of the device, the sharp edge passing between her cleavage. Her hands, cuffed behind her, were chained to the ceiling, pulling her face and torso even farther downward and helping to stabilize her, though her shoulders did not approve.

Her pussy felt raw and chafed, not even afforded the meager protection of panties. Having all her weight pushing down on a sharp edge running between her labia was not her idea of a good time.

Jennifer’s blonde hair clung wetly to her back and face, rivulets of sweat running down her body. Attendants were quickly making the rounds, connecting the milking apparatus to each of the ‘cows.’