The Terrible Life Of Thomas
  • Author - TPECurious
  • Rating -   
  • Site Rank - 2656 of 2955
  • Story Codes - F-m, non-consensual, cbt, chastity, cross-dressing, drugs, extreme, humiliation, mind-control, slavery, torture
  • Post Date - 10/18/2020

Author's Note: First time submitting a story, constructive criticism welcome. I tried to keep the paragraphs short for ease of reading as this is a bit long. There are ideas for torturing Thomas more, if people enjoy this story I will get to putting part 2 down ASAP. Also this is a work of fiction, please don't bring the real world into with comments on the legality of what's happening.

Chapter 1

Christy awoke early in the morning and looked over and the other girl in bed, Tara. Though similar in height and eye colour, they were opposites in almost every other way. Christy was blonde with blue eyes, pouty lips and soft features.She was a bit chubby with a bubble butt and soft thighs, and an EE-cup. Tara was raven haired with blue eyes, slim and muscular with sharp features, her butt cheeks and thighs were firm, and she could make her B-cup tits bounce by flexing muscles. She had a huge smile that could light up a room, and with her healthy lifestyle her teeth still shone fairly white.

Christy slowly pulled the covers back to reveal her and Tara's naked bodies, the differences and similarities on show. Christy had large areaola and nipples that were quite soft an unpronounced but would darken and harden when she was cold or aroused, with little bumps forming on her aereola. Tara's small, dark nipples stood out like bullets regardless of weather or arousal. They both allowed no hair on their bodies from the nose down and would often spend their leisure time together slowly caressing each other on the arm, back, leg.

Feeling a familiar tingle of excitement Christy started to gently trace her finger across Tara's collar-bone then down her outer torso, her perpetually hard nipples may have made it difficult initially for Christy to tell when Tara was getting aroused, but their intimacy over the last few years had given her other clues. She noticed Tara very slightly bite her lip as she traced lazy circles around her flat stomach, a slight clenching of Tara's thighs as she moved her finger down over her hips.

With gentle movements Christy gripped Tara's nipples between her thumbs and forefingers and lightly pulled and rolled them, feeling her own excitement grow as she watched Tara bite her lips more noticeably this time. Tara mumbled something and shifted position, giving Christy easier access with her hands but Christy continued the light tease. Fondling Tara's tits and rolling her nipples, Christy then lent in and kissed Tara's neck. Tara gasped at the contact then moaned quietly, her own hands starting to roam Christy's body she pulled and rolled her nipples in return and smiled as she felt them harden. It was a sensation she never got tired of.

The lovers continued their teasing embrace for about 15 minutes, each teasing and egging the other on. A nipple was lightly pulled, the other would pull harder. A neck was kissed, a neck was sucked in return. Both ladies moving their fingers within millimetres of the others slit, teasing and toying with each others lips until Christy dropped a bomb. She slid her finger up Tara's slit, making sure to avoid her clit as she collected as much of her juice as she could then rubbed it over Tara's nostrils. Tara moaned loudly at this and her whole body tensed in anticipation, then she groaned as she realised Christy had won their competition of who could arouse who the most without actually going for the easy win.

Both ladies moved back in to a warm embrace, breasts pressed against each other and legs intertwined as the cuddled. They whispered and giggled a little bit before looking up at the camera above them smiling coldly. "I wonder if she enjoyed the show?" Tara asked loudly for effect. "Ohh I'm sure she did" Christy responded. She sat up a little and cradled her large breasts, tweaking her own nipples she continued to smile at the camera "You know that sissy pervert can't help herself!". The girls laughed loudly at this, both knowing Christy's former boyfriend was watching. The both got up from the bed and sat down together at a large makeup table, a pen and paper already set up with another camera there to catch their actions.

Christy held up the pen and pad to the camera, the paper was pale pink with a few different motifs repeated: Barbie, Tinkerbell, My Little Pony, love hearts, and flowers, and the pen was a hot pink coloured gel pen. "Time to learn what your sissy maid duties are today bitch" Christy said almost in a sing-song "and Mistress Tara gets to decide for you!" Tara smiled coldly at the camera and picked up from Christy "You were a very naughty girl yesterday Tiffany" Tara scolded. "Running away like that, like you have a snowballs chance in hell of escaping!" Her laughter became a sigh and she continued to tease "One day you'll learn that the only thing you need to concern your sissy little head with is obedience".

The previous day Tiffany, formerly Thomas, had tried to escape the clutches of the two women holding him captive. He had seen an open door and made a run for it, though "run" is a generous description. He had managed to slide off one of the 6" heels he was forced to wear daily but couldn't quite get the other.

The new height difference between his ankles meant the 10cm chain that hobbled him via his ankle cuffs was stretched pretty much taught before he even took a step. Still he made a go of it, getting out the back door and about 35 meters away, dreaming of being fee, before Tara caught up to him. She grabbed him by his balls and squeezing hard she dragged him back into the house, he flailed his arms as much as he could, which wasn't much as his wrists were cuffed and held together by a 10cm chain than ran through the D-ring of his posture collar keeping them pretty much level with his collarbone, while his cries and begging were muffled and garbled by the gag locked in his mouth.

"Attach new run prevention device" Tara spoke as she wrote, then she looked directly at the camera and as if she was teasing a child she chirped "so the sissy maid can't EVER escape!" She looked over at Christy and licked her lips "I think Tiffany needs to be reminded of just how lucky she is to serve us" Tara began to write again "lick shine Mistress Tara and Mistress Christy. Run the shower for Mistress Tara and Mistress Tiffany. Moisturise Mistress Tara and Mistress Tiffany" Christy was moaning softly now listening to Tara, placing one hand on her breasts and the other between her legs she started to tease and play with herself.

"And sissy needs to earn her keep" Another moan from Christy. "Clean the tiles in the bathroom with a toothbrush" Christy tipped over the edge at this with her face still facing the camera she closed her eyes with her face twisting in pleasure she almost screamed through her orgasm, the tiles of the bathroom extended halfway up the walls as well as covering the floor and interior of the shower. It would take him hours!

The girls got up and got dressed in their normal attire for teasing Tiffany: tiny flesh colour g-strings, and flesh coloured nipple tassels. While they were happy flashing everything to him on camera they had denied him seeing a woman physically naked for years. They did this for no other reason than to be cruel, and sometimes during sex they would gush breathlessly to each other about how desperate he must be to see them completely naked in the flesh.

Tiffany's door was pink and in large, bold lettering was written "Sissy Maid Tiffany's Cell". Cell was appropriate as the door handle was only on the outside, along with an upper and lower deadbolt, the mortice lock in the middle allowed access. The hinges were also on the outside of the door, and while Tiffany was chained up securely and then locked in a cage, they didn't want to give him even a glimmer of hope of escaping, the open door the day before not-withstanding.

The ladies entered one at a time with the first one in, Tara in this case, responsible for restraining Tiffany to the large St. Andrews Cross in there. She unlocked a mesh cage door that held some of the instruments they used to torture Tiffany and selected a cattle prod. Holding it up to her eyes she clicked the button a few times and watched the electricity arc between the two prongs. Licking her lips she said "I hope you try and escape again bitch, I'd love to use this for a reason other than boredom". She looked down at the cage and laughed as she watched Tiffany struggle, chains and padlocks making loud clicking noises.

He was nude and his skin reflected the harsh white light from above. After she had unlocked his cage and dragged him out, she encouraged him to stand up against the cross with a swift knee to the balls and the cattle prod arcing in front of his eyes. Too scared and in too much pain to fight back he felt Mistress Tara go through the usual motions of restraining him.

First she would clip his collar to the cross, then strap his midsection tight. Afterwards she would clip 1 shackle to a ring set into the floor and uncuff his other ankle, quickly moving it into position and locking it to the cross she would then unclip his other ankle and repeat the process. His arms were always too sore for him to put up a fight, cuffed as they were for hours on end through the D-ring of his collar by a 10cm chain. She would press the cattle prod against his balls and with her free hand she would uncuff him and recuff him to the cross so he was spreadeagled.

Tiffany took this time to look around the room as he had done every day for 3 years, and the years he'd lost count of. He hated the room. They never turned the light off so he could see his cell at all times and be reminded of his place. Besides the St. Andrews Cross the room was dominated by a huge TV and 7.1 surround sound that broadcast to him the shows the women put on for him and endless videos of blowjobs the rest of the time, zoomed in so the only thing visible in the videos was the mouth going to work on the cock.

He would try unsuccessfully to ignore the videos and his feelings of extreme frustration watching these lucky men getting their cocks licked and sucked until they orgasmed. Tiffany couldn't remember the last orgasm he had or how it felt. He was also extremely jealous of Tara when he watched her exploring and enjoying Chrity's body, a cruel reminder of the time years earlier when it was his hands sliding all over her body, his mouth between her legs, and his cock buried deep inside her. His cock would swell against its small metal cage and he would become painfully aware of how full his balls were as precum leaked from his throbbing cock.

Also around the pink painted room was a pink wardrobe with his outfits, a pink set of drawers with his lingerie, a pink shoe-rack with his high heels, and the wire-mesh cage with the torture devices. He glared with pure hatred at the pink dyed hessian lining of his cage, it itched him and annoyed him through the nights and drove him almost as mad as his cage which was too small to lie down in, and too small to sit up in. Long ago the ladies had told him pink was now his favourite colour and were going to do everything the could to make that colour dominant in his life. They had phrased it and spoken it as it as if they were doing him a favour, and his negative reaction had earned him an extra 15 minute cycle of on top of his "earned" "behavioural correction".

Behavioural correction was a nightly occurrence that would see him strapped spread-eagled to the St Andrews Cross, they would remove the specially designed parachute from his balls as well as its battery pack and bring out the power drill with the modified bit. It had a solid piece of wood sticking out with 2 straps of leather attached, and pressing the trigger of the drill would cause the straps to spin like an auto-spanker.

They would then read out each of his infractions for the day as well as the time sentence for it. For example: not making an effort to curtsy was a 30 second sentence of ball spanking per infraction, whereas not enthusiastically responding with "Yes Mistress" after an order was a 1 minute sentence. Christy would always begin the sentence by snuggling up nice and close to him, pressing her large tits against his torso, tracing her fingers up and down him she would whisper seductively in his ear "don't pout sissy, we aren't punishing you, we're just correcting our maids bad behaviours".

Once Tiffany was secured and helpless against the cross Tara went back to the door and knocked rhythmically, the rhythm being decided upon earlier. Christy entered the room with her usual flourish, making sure to make her large tits sway and smiling to herself as she saw Tiffany's eyes glued to her chest, the door key on a chain between them, and his cock straining hard against its tiny metal prison. "Does sissy want to see my boobies?" She sneered condescendingly. Swallowing his pride and hoping today would be the day, Tiffany nodded emphatically and tried to beg with his eyes and through his gag. "Well too bad!" She laughed, then laughed louder as she heard Tiffany groan with frustration and the metallic noises of him trying to fight against his cuffs.

"Mistress Tara told me what a bad girl you were yesterday Tiffany, and how little gratitude you have shown for all the nice things we've done to you, and for you" Tiffany grimaced at this which Christy noticed. She balled up her hand into a fist and with it still hanging by her side she drew her arm back. Tiffany noticed and tried to shake his head 'no' but the the posture collar prevented it, the gag muffling his begging she swung her arm forward in a lazy arc and smacked him square in the balls. He yelped loudly and whole body tensed in pain and he strained against his bonds trying to double over as Christy drew her hand back again. "I guess we'll just have to work EXTRA hard now to break you bitch!" She laughed and smacked him hard in the balls again and a 3rd time.

He was panting as he struggled, practically crying as Tara came over to him holding a length of chain, a few padlocks, and a 6kg kettle bell. She caught Tiffany's eye and smiled as she spoke "What this? This is your run prevention device sissy, it should be familiar". He did recognise it and was almost overcome with panic. He hated the kettle bell and how the ladies used it in his monthly "escape room" sessions where he was forced to participate in heavily stacked challenges to earn his freedom. When he invariably lost the ladies would mock him for his apparent desire to continue to serve as their slave. He would scream and curse and beg for freedom, and the ladies would laugh and add time to his behavioural correction session.

Kneeling down Tara continued to mock him as she padlocked the 2 chains to his parachute "Oh yes, no more running for sissy" she fed the chains down either side of the handle of the kettle bell and lined up another padlock "This should make your life even more fun sissy" Tara ignored him as he begged through his gag and tried to escape his punishment, she simply clicked the padlock shut and stood next to Christy to admire her handiwork. "I bet it makes it hurt even more when you're summoned bitch, you'd better not drop anything or there'll be hell to pay!" The kettle bell was chained so it just touched the floor. When he walked it would pull down on both sides of the parachute squashing his balls together as he was forced to drag the 6kg weight around.

"Safe and secure" Christy smirked and she took a good look at the man who'd once been her boyfriend. His hair was kept in a buzz-cut as it made it easier to fix one of the many wigs they'd gotten for him, and his eyebrows were plucked thin and styled with feminine arches, otherwise his body was kept hair free. His nails were all kept at a certain length and painted with a pink glossy polish, the ladies would measure his nails every day to ensure he was keeping them 2cm long, short enough to be practical and long enough to be feminine.

She smiled as she looked at his face, his pierced ears with the large hoops and the red lipstick that was tattooed onto his collagen injected lips, they had decided on red so he would still have to apply lipstick daily but even without lipstick he would sport plump, feminine lips. Her eyes wandered down to his nipples, they were pierced with a fairly thick gauge ring in each, perfect for hanging weights off. He had a few more tattoos, one across the small of his back that read "Sissy Maid" with a traditionally dressed French maid dusting the lettering, and one above his cock that read "Locked Clitty" the o in the female symbol shape, and the i in the shape of a cock.

His chastity cage was tiny and took a bit of effort from the girls to put on. They would coat a bag in numbing cream, fill it with ice and slide it up and down his cock, icing and numbing it until it had almost shrivelled away before carefully fitting the hinged ring behind his balls, sliding in the spiked anti-pullout bar, and finally trapping his cock in a single piece of stainless steel that was barely 3 cm long and 2cm wide.

Once the cream had worn off and his cock had warmed up, he would fill the cage to the point of being uncomfortable. Any sort of arousal and his cock would swell painfully without being allowed to grow. To compliment the anti-pullout bar it had a built in high security lock and when the plate was put on over the keyhole it was inaccessible and invisible. Tiffany hadn't found a way to get free of it despite trying for years.

"Now that's on" Tara snapped "You may now ask for permission to put on your makeup and maids uniform and serve us sissy". Thomas had fought hard against this, begging to be allowed to put makeup on and dress like a girl? Like hell!! So they tortured him each time until he begged. Slapping his balls rhythmically, twisting his nipples, zapping him with the cattle prod, they also added permanent punishments such as the collagen, then the tattoos on his lips and body, he finally broke when they threatened to tattoo a cock on his cheek pointing at his mouth. Now he was too scared to do anything but beg through the gag. He pleaded to be allowed to put makeup on, and begged for his lingerie and maids outfit, gushing about how much he wanted to serve them.

Tara couldn't help herself as she watched him beg, sliding her hand between her legs she rubbed herself over her panties not surprised by how moist she was already. She reached her other hand out and groped Christy's tits, fondling and squeezing as she rubbed herself to the sweet sounds of Tiffany begging. In no time at all she rubbed herself to a screaming orgasm, Christy helping her stay on her feet. They then embraced and kissed passionately while Tiffany looked on jealously.

They eventually broke off the kiss with a sigh Christy said "she really seems to want to serve us, let's find her some clothes". Presently Tiffany was dressed and had fixed her makeup, the years of bondage had left him physically weaker now than the girls but they still liked to encourage him with cattle prods. His wig today was blonde pigtails kept secured with bright pink scrunchies, similarly coloured lipstick, black eyeliner and sparkly pink eye shadow. He knew he must look like an over the top drag queen, and his shame caused his cheeks to burn red. Never missing a chance to tease him Tara had commented that he loved playing dress up so much he had provided his own blush.

Today though things were a bit different as the ladies hadn't finished punishing him for his escape attempt yesterday, they were determined to break him. Tiffany knew what was waiting for him if he broke, and it was a fate worse than he was already living so he was determined not to break. Today they had applied a contact glue to his chest and affixed huge fake tits, GG-cups they told him. They also secured 6cm long acrylic nails to him and made him paint them the same sparkly pink as his eyeliner.

He wore a matching set hot pink bra, g-string and garter belt with black stockings covered in pink love hearts. His maids uniform was tight fitting leather that locked on with a padlock, though instead of black and white it was hot pink with black highlights, and 6" heels that were now padlocked onto his ankles. The skirt was extremely short ending right around where the parachute would hang, but the ladies made him tuck his cage as far back as possible with orders to keep it there.

Walking was a challenge and Tiffany found he would have to mince with his thighs pressed tightly together, his hips swaying dramatically as he adopted an overly feminine walk to keep himself tucked away. Each infraction where one of the ladies would have to help him re-tuck was worth 5 minutes of behavioural correction, and despite hundreds of hours of punishments encouraging him to comply, he would still become untucked a few times a day. He almost groaned out loud as he considered how the kettle bell was going to affect him now.

His ankles were hobbled again by the 10cm chain, and his wrists were cuffed together on the 10cm chain thread through the D-ring of his posture collar. He was then leashed and the ladies started slowly walking towards the cell door, gently tugging on the leash as they watched Tiffany struggle. He minced as normal once trying to balance to weight of the huge tits on his chest, then felt resistance against his balls, taking a breath he then went to take another step forward and felt his balls being slowly crushed, it hurt but he managed to make the kettle bell slide.

Taking another breath he felt the tug on his leash and looked up at the ladies who were smiling cruelly at him. With a soft groan he took another mincing step forward, then a louder groan as his balls were squashed again by the next step. He felt like crying, he couldn't possibly go the whole day like this, but deep down he knew that not only would they make him endure it, they would laugh and get off on it. He slowly made his way to the ladies, 8 steps and he was panting, his balls now aching from the effort. "Hurry up sissy, it's time to start your chores!"

Tiffany groaned in pain with each step but they eventually got him to the bathroom to start his first chore. They removed the gag from him and the took turns giving him cups of water from the toilet. When he couldn't drink any more they forced him him to gargle mouthwash, then dragged him down to his knees and Christy took position in front of him. "Lick shine me sissy" She snapped and he started licking the top of her foot. He licked and licked, savouring the smell and feel of her skin as he moved his way from her feet up her shins and calfs, her thighs, being so close to her pussy all he could smell was her and his cock throbbed painfully hard in its cage.

He licked her ass cheeks and precum started to ooze out and pool on the floor of the bathroom. He wasn't allowed to lick anywhere that was covered, so while he could breath in the smell of the ladies he wasn't allowed to look at or taste them. He struggled up to his knees and licked Christy's hips and waist, desperately wishing she would uncuff him so he could fuck her again. He had made the mistake of nuzzling her and begging for sex many times, until they had introduced the behavioural correction, now he just submissively licked.

At her tummy he looked up and his entire field of view was Christy's large tits. Licking them was always the hardest part for him, there was plenty of soft skin for his tongue to explore and he could see the tassels rise as her nipples hardened, he would also have to lift each one to lick underneath them and more often than not he would earn additional sentences for touching them in an "overly sexual" manner. He didn't know exactly what that meant but he suspected it was just an excuse to torture him more.

He was a wreck by the time he finished licking her tits, grinding his hips against the air he untucked himself, precum still oozing out onto the floor. Licking her back, armpits, arms and neck passed by in a haze and Christy was panting by the time he finished. Tara retucked him with a few choice remarks, then he started to lick her from foot to neck, managing to untuck himself again in the process.

With encouragement in the form of twisting nipples and hard flicks to his balls Tiffany licked up the precum he had leaked out onto the floor. He was then regagged and, as the ladies put it, he was allowed to run their shower. He was then led into the adjoining room that contained moisturisers and other skincare products as well as another T.V His leash was secured to the leg of the cabinet in there and the T.V was turned on.

Locking the door behind them the ladies stripped off their flimsy g-strings and tassels and hopped in the shower together. They smiled up at the camera and put on another show for Tiffany, slowly soaping each other up, massaging each others breasts and ass cheeks. While exploring each others mouths with their tongues they gently rubbed each others clits, working each other up into a passionate frenzy that ended with almost simultaneous screaming orgasms. They finished their shower and turned the water off, the faint moans of Tiffany's frustrations coming through from the other room causing them to smile as they put on a fresh g-string and tassels.

They unlocked the door and entered the room and saw Tiffany so overcome with need he was trying to rub his caged cock against the side of the cabinet, precum oozing out again. Tara sneered at him "stupid sissy, do you even remember what it feels like to cum?" Christy chimed in as she retucked Tiffany "You're here to serve us Tiffany, that means no cumming for you so stop trying to rub your clit". Tiffany sobbed a few times as he gathered himself, he would be forced to clean up the precum here, and knew he would be punished both for untucking and trying to orgasm later.

Tara clicked her fingers then pointed at the moisturiser on the cabinet "hurry up maid". Tiffany groaned and painfully minced over to the moisturiser and dropped to his knees. It took him a long time but he managed to moisturise Christy and Tara from foot to face, groaning louder than ever in frustration as his hands worked the ladies inner thighs, smelling how aroused they were both getting again, then their ass cheeks. As he was rubbing moisturiser into Christy's tits he was again reminded of their life together before Tara, he groped, grabbed, kissed, and fucked to his hearts content. Now he wasn't even allowed to see her naked in the flesh, let alone touch her intimates.

While moisturising Tara's ass she bent over at the waist, teasing with what he would see if she didn't have the g-string on, and she slid a finger between her legs. With his nose centimetres from her ass she rubbed herself a loud orgasm as he rubbed her ass cheeks, a faint wet spot appearing on her panties. Christy smiled at the show and remarked at how lucky Tiffany was to have 2 such beautiful and thoughtful owners.

A short time later Tiffany was on his knees in the kitchen panting, his balls aching hard from the mincing walk from the bathroom to the kitchen. He was fed from a bowl on the floor and the ladies would cook him up a bland, tasteless gruel that was loaded with vitamins, minerals, and supplements to keep him healthy. Not allowed to use cutlery he would have to eat like a dog and lick the bowl clean before he was allowed to stop. He had resisted at first and refused to eat, the ladies had left the bowl of gruel there. The next day he was too hungry to care and buried his face in the day old gruel, and although he had forgotten how terrible it tasted he knew that fresh gruel was preferable.

After breakfast he was ordered to do their washing up. The ladies had eaten well, bacon and eggs with orange juice. It never got any easier as he couldn't adjust to his cuffed hands, but eventually the washing up was done. He was then ordered to vacuum the house, the kettle bell causing him no end of pain and the large fake tits obscuring his view even more than the posture collar normally did made the chore even harder than it normally was.

Eventually he was led painfully back to the bathroom and given a cup, a toothbrush, and cleaning vinegar. Gesturing to the bathroom he was given a short, sharp order "clean, maid". He minced to the sink and ran the water until it was hot, putting a little cleaning vinegar and hot water in the cup, he moved to the shower and began to scrub the tiles with the toothbrush. While he was cleaning the ladies lounged on the patio and tallied up his infractions so far.

Talking back and forth they listed out: 4 untucks, 2 precums, attempted orgasm, no curtsy x 3, sexual touching of both ladies x 4, not thanking Tara for putting on the anti-run device, not thanking them for breakfast. Giggling as it was barely 11am he had already racked up over 2 hours of behavioural adjustment. They joked with each other how after all these years he still fought against them.

Hours later Tiffany was back on the St Andrews Cross naked, the fake tits still glued to his chest. Cleaning the bathroom tiles had taken him the better part of 7 hours as the toothbrush was a rubbish cleaning utensil and he had to constantly change the water in his cup. He was also frequently summoned by the ladies for menial tasks. He would be scrubbing the grout, or a tile and the device in his parachute would go off. It would shock his balls with a quick zap similar to the static build up from running your feet over carpet or sliding down a plastic slide. It was a sudden shock and it hurt him, his whole body would jump when it activated and he painfully minced off to find the ladies.

Taking careful steps with his high heels as he dragged the weight with his balls and balanced the weight on his chest he found them here and there around the house, always in a state of relaxing. It drove him mad that he was forced to not only serve these evil women, but they would give him useless tools like a toothbrush for cleaning. Then to add insult to injury they would shock his balls to summon him to where they were lying on a couch, or sunning themselves in the backyard to be told "fetch me a drink maid" or "pass me the remote control maid" and "put sunscreen on me maid". He was even told to stand and watch as the ladies kissed and teased each other to another orgasm each.

Eventually he had the tiles cleaned though, the shower presenting him the most trouble as he had to stretch on tip-toes for his cuffed hands to be able to reach the top line of tiles, the action forcing him to lift the 6kg kettle bell off the floor by his balls. The ladies had inspected his work and more often than not they would find imaginary spots he missed, today his worked passed their inspection.

Tara was removing the parachute as Christy organised the drill. The parachute was a bulky piece of equipment and every time it was removed and replaced Tiffany couldn't help but remember the hours and hours he had spent tied to the cross with heavy weights on his balls, stretching them in a cycle of 10 minutes then a 5 minute breather, until they had stretch a few more centimetres to accommodate the parachute.

The ladies didn't tell him what it did in advance, preferring to have him find out the hard way. Beyond the zap they used to summon him it also had an inbuilt GPS that was linked to the proximity system which would shock him if he got further than 50 meters from the house. His desperation to be free had won over his fear of the shocks the day before. It was also linked to his posture collar which had a setting similar to a dogs bark collar, with the flick of a switch the collar would spring to life and shock him in tandem with the parachute if he tried to speak or make noise.

They had and still did tease him mercilessly with this, activating it and telling him if he clearly stated his intentions they would be granted. If he wanted to fuck them, to be free, "just tell us sissy" they'd tease "anything you want, we'll even serve you as your slaves!". The teasing would get to him and each time he thought this was the time he could endure the pain and be free, of course every attempt to speak was met with painful shocks, and he would yelp in pain which would lead to more shocks. Once in that trap it took every ounce of self control for Tiffany to endure a shock without whimpering so it would end, and the ladies would tease him about his desire to continue as their slave.

"Two and a half hours sissy!" Tara enunciated each word, drawing them out as Tiffany started to tremble in fear. Christy rubbed herself up against him and whispered her usual "we're not punishing you sissy, we're correcting our maids bad behaviour". Tara continued "and what a naughty girl you've been!" She pressed the trigger on the drill a few times and the leather straps swished through the air. "Failing to curtsy, failing to say yes mistress, untucking yourself..." Tara continued to read out his infractions as Christy teased him with her soft body.

Then Tara moved in close and Christy stepped aside so she could begin. With the drill in place Christy started the clock which ticked each second so loudly and slowly it made time seem to almost stand still. Tiffany tensed in fear of what was about to happen as Tara activated the drill, the leather straps moved slowly at first warming his balls up for about 10 minutes. He was moaning and groaning softly until they sped the drill up faster and faster. The straps were placed so that once the drill was at speed the time it took for the first strap to completely leave his balls was the time it took for the second strap to slap into them, not giving Tiffany a chance to recover as each painful hit made his balls dance.

His screams of pain were muffled by his gag, and the bondage prevented him from escaping the cruel straps, he had no choice but to stand there helplessly and take each slap to his balls. They cycled with 10 minutes of slapping and 5 minutes of rest, taking turns with the drill and kissing and caressing each other during his 5 minute breathers. They also spoke to each other about him as they tortured him.

"I like the tits, maybe they should stay" Laughter as Tiffany screamed. "He can't even reach them, imagine having a toy that close! They feel so good to, worth the money". More laughter over the screams of pain from Tiffany. "Maybe we should make it permanent, get her implants to match her lips" Tiffany was resting now, each panted breath from behind the gag was accompanied by a low moan of pain and a stream of drool as his balls throbbed. "Might be worth looking into. Do you want a nice pair of tits of your own sissy?" Thomas groaned louder in the negative, hating what they'd already done to him.

It felt like a million years to Tiffany as the clock and the pain from the torture warped his sense of time, but eventually they finished his behavioural correction. He was crying well before the end of it, the pain in his balls had spread to his stomach and had left them too tender to touch. The ladies laughed as he screamed again while they reattached the parachute to his tender balls along with the anti-run device, he doubted he could make it move in his current state. They then chained him back up and locked him in his cage for the night.

Tiffany struggled in his small cage, his balls still throbbing in pain as he tried to escape. It was the same desperate attempt, and the same failure he had experienced every night since Tara had weened him off the drugs she'd used to enslave him and reprogram Christy. He thought back to their first meeting, she had seemed so normal that nobody could have guessed the evil that lived in her!

Tiffany struggled to remember, he was determined to escape and tell his story but he needed to remember. He had a job once, computers? Engineering? He had designed something, or written something. It gave him money each month, a lot of money each month. Well it used to give him money, he shuddered as he remember being tortured into signing over the...Tiffany scrunched up his eyes and thought hard, patent! He had owned several dozen patents and was making a killing from them.

He remembered feeling like he was coming out of a dream to find himself chained up in a nightmare. He had been sick for weeks until his body had flushed everything when Tara hit him with the bomb and explained how she had drugged him and Christy, and was continuing to program Christy with sexual rewards for cruel deeds. The drugs helped and Christy couldn't help it now, she got amazing levels of sexual satisfaction from torturing him.

Tara had told him he was now completely drug free so he could better experience the misery they were going to inflict upon him. He tried to fight against his chains and yelled, demanding to know why. Tara had laughed and her answer infuriated him "Because you want it". He had opened his mouth to spit out an insult and call her a liar when Tara had slid a gag in. It was the last time Tara spoke to him evenly, from then on she was either teasing, scolding, patronising, or snapping.

He remembered how a few weeks after that Tara and Christy had hung weights from his nipples and balls, then they took turns in spanking him with a wide leather strap for minutes at a time, then they would stop and while his ass was burning in pain they took turns lifting the weights on his nipples and balls then dropping them. He had cried as he saw a depth of cruelty in Christy he didn't think was possible as her and Tara teased him throughout.

Rolling in his cage their voices haunted him "Just sign bitch" "We will torture you forever if you make us" "It hurts for you but it's fun for us, I hope you never sign" Their voices had blurred together as he lost focus on everything but the pain from his ass cheeks, nipples, and balls. Eventually he had relented, with one holding his balls tightly he had signed over the patents to the evil women to the chorus of their laughter. His bank account soon followed along with his savings, e-mail accounts, passwords, they had tortured out of him complete control of his life.

Tiffany rolled again in his cage, the clock still ticking loudly. Normally they turned it off but tonight they'd left it on, each second felt like a year as the hessian and small sized cage continued his torture. He eventually fell into fitful bouts of sleep. The T.V woke him up bright and early as the sound from the porn suddenly un-muted and he could hear a very sloppy blowjob happening. He lay there watching jealously as he waited for his Mistresses to come and un-cage him and start his brand new day of hell.

Eventually the door opened and he groaned in lust as Christy bounced in, his eyes glued to her large swaying tits, trying desperately to make out her nipples under the tassels. She stopped in front of the cage and looked down, smiling at him and held up an odd looking 6" dildo then placed it on top of his cage.

"Once you're safe and secure Mistress Tara and I will show you your new feeder Sissy, we may even have to change your name to cock-slut, because that's what you're going to become!" Tiffany closed his eyes, wishing himself away from this place as he heard the cage door open. 'How much more could these 2 psychos possibly do' he screamed in his mind, knowing that the 2 women would take great delight in showing him exactly how much more miserable they were going to make his life.

Chapter 2 (added: 2021/01/25)

The next 2 weeks after Tiffany's failed escape attempt seemed to pass ever slower for him. He wasn't 100% sure why, but he figured that the hope of freedom he momentarily felt was still clashing with the reality of his slavery. Also contributing to the frustratingly slow days was that the fake tits and long acrylic nails had become permanent fixtures. The tits were removed every night to clean his skin, and the nails were reattached every few days as the glue would break while he served. Combined with the posture collar they eliminated most of his downward vision, as well as made every chore even more difficult than they already were.

To his increasing dismay the women also left his anti-run device on. It turned every step into a painful battle as his balls were crushed while he pulled the 6kg kettle bell. He experimented with different steps and styles of walking as best he could, but after untucking himself a half a dozen times with no change to the pain each step brought him, he gave up. Stairs were the worst as he was given a tough choice between lifting the weight a bit early for the first step and doing an awkward waddle then step, or he could take extra steps to bring the weight as close to the first step as possible before lifting. Both options were agony for his already tender balls and he earned a lot of behavioural correction by begging for it to be removed.

The ladies also increased Tiffany's level of denial and he soon realized it was possible for his sexual frustration and desperation to be worse than it already was. He had been in his current tiny chastity cage for about 3 years and hadn't seen a naked lady in the flesh for longer. To further deny him they added spaghetti strap tank tops and small gym shorts over their tassels and G-strings, and the result was almost instantaneous. Tiffany's eyes would dance about as he struggled to catch even the smallest glimpse of hidden skin as they turned, knelt, and bent over. To drive the point home they also stopped their nude shows on camera for him, and while they still revelled in pleasuring each other in front of him it was now all done over their new attire.

Tiffany lost track of time again in these 2 weeks as the days melted back into the usual pattern of slavery, humiliation, and torture. He tried to obey and behave, terrified of the women making his life even more miserable and difficult than it already was, but he was still earning about 40 - 60 minutes per night in behavioural correction. This was mostly thanks to rules such as 'no untucking' that were impossible not to break, and accusations of leering whenever he glanced at the women in their new clothes, and every evening as he was strapped to the St. Andrews Cross he would beg through his gag not to be tortured.

The women would pause and listen for a minute or two, just long enough for Tiffany to get the faintest hope that tonight was the night they would spare him, before Christy would tell him they weren't punishing him, they were correcting his bad behaviour. Tara started promising him that if he could go a whole day without earning behavioural modification time then he would be allowed an orgasm. She played it up and no matter how hard Tiffany fought it, he couldn't help but imagine how amazing it would be to cum again after all these years and resolved to try harder. Tara would laugh and take extra pleasure in pointing out that today was not that day, he had instead earned behavioural modification.

The new outfits slightly changed some of his duties and now he was 'given permission', as the ladies always phrased it, to only worship Christy's feet before thanking her for allowing him to serve as her sissy maid. Tara on the other hand took to blindfolding Tiffany before making him worship her ass cheeks and thank her for allowing him to serve. Tara knew Tiffany hated her and she took perverse pleasure when she imagined how humiliating it must be for Tiffany to blindly worship her ass cheeks, then politely say "Thank you Mistress Tara for allowing me to serve as your sissy maid". As much as Tiffany hated Tara, the feel of her ass underneath his tongue and her faint aroma would leave his cock throbbing painfully in its cage, every morning and every night.

When he was ordered to lick or moisturize their bodies, it was now around the confines of the new outfits. He would try and resist but as he held their legs and licked further and further up their thighs, he would see how horny they were getting and he would silently beg that today he would be allowed to see and taste their pussies. As he licked he would get caught up in his fantasy and in his mind he licked them both to such amazing orgasms that they unlocked his cage and allowed him to fuck them both. His cock would press hard against its cage and precum would ooze into his G-string, he would be just about panting when the women would snap their fingers and order him to move up to their midriff. It took all his willpower, but he would sadly obey as his fantasy faded away.

For 2 long weeks Tiffany suffered like this until one morning when he was awoken in his cage by the usual porn. It was a typical video designed to keep him sexually frustrated, jealous, and desperate. A plump, feminine set of lips lovingly worshiped a huge cock, drool and precum running down her chin as she performed a loud blowjob. Tiffany's cock throbbed painfully in its tiny metal prison as he watched her swallow the huge cock, gag, and pull it out with more drool and pre-cum cascading down her chin. He heard the grunts from the man as he approached his orgasm, watched as the guy pulled his cock out and aimed it at the girls face. He was beyond jealous as he watched the lucky guy shoot his load all over the girls face, desperately wishing he could do the same, before another cock took its place and the woman started sucking again.

He heard his room door being unlocked and he glanced at it, dreading yet another day in this nightmare his life had become. Christy almost bounced through the door in excitement, and Tiffany groaned loudly in lust as he saw her. She wasn't wearing the tank top today, only the tassels! His eyes were glued to her large tits as they swayed and his cock throbbed harder in its cage, releasing a tiny bit of precum. He was so focused on her tits that at first he didn't even notice the dildo in her hand, and it wasn't until she placed it on top of his sleeping cage that he saw it and began to worry. "Once you're safe and secure Mistress Tara and I will show you your new feeder Sissy, we may even have to change your name to cock-slut, because that's what you're going to become!" Christy announced happily, ignoring the groans and garbled attempts of "No" coming from Tiffany.

Anything was better than whatever depravity they'd dreamed up for him now and he begged in his mind and garbled through the gag 'please, no more!'. It didn't make a difference as Christy almost dragged him out of his sleeping cage and tied him to the St. Andrews cross. Presently Tara joined Christy and they stared at him with evil smiles on their faces. Tiffany scrunched his eyes closed tight in a pointless attempt to hide from the next round of torture. "Open your eyes sissy, or you'll miss learning how to use the wonderful thing we brought you!" Christy spoke patronizingly, like he was a child about to miss out on some great reward. Christy lightly gripped his balls which, in their previous life together, he would have found enjoyable. Bound helplessly to the St. Andrews Cross, and knowing how much the women enjoyed torturing his balls caused his eyes to snap open instantly.

Tara snorted with laughed as she choked out "You have him in the palm of your hand my love". Christy smiled at Tiffany and squeezed gently saying "I sure do babe". The pet names they had for each other got to Tiffany the most. Every day for over 3 years he had been forced to confront the fact that his girlfriend had cuckolded him with another woman, and together they'd locked him in chastity, enslaved him, and continually tortured him. 'But that was a physical thing' he'd tell himself. The pet names meant there was an emotional connection between them too, and made him doubt ever being free of his slavery.

The women had picked up on that and used its power over him sparingly, usually using it when they had dreamed up some terrible torture or another and were telling Tiffany about it. Today was no different as Christy held up the odd looking dildo. "How about you describe it to Tiffany, and I'll do the demonstration baby" Christy cooed to Tara who licked her lips playfully and overly seductively, complete with a fake groan of pleasure cooed back "Only if you make it a good show my love".

Christy held the 6" dildo up to Tiffany and let him get a good look at it as Tara spoke. It was designed like a strap-on so there was a base behind the cock and balls, however there was a button on the base directly above the cock. There was a tube extending out the back of it connected to a clear box, and there were also clamp bits around the base that could be detached so it could be used as a strap-on, or attached to its accompanying 30cm tall stand.

Christy drew Tiffany's eyes to the head of the cock which sported a large urethra, "For the tube" Tara's voice interjected. The shaft of the cock seemed to have a moving part about 1/3rd of the way up that could slide backwards and forwards, which Christy demonstrated with her hand. He noticed that the more she pumped, the larger the balls seemed to get. Thomas was getting more and more worried and he didn't want to know what Christy had meant when she called it his feeder, but the demonstration continued regardless.

Christy then rubbed the dildo up and down between her tits with an odd smile, bringing her other arm across her ribs she cupped her tits as best she could in the crooks of her elbows and proceeded to fuck her tits for a long few minutes. Tiffany was panting lustfully as he watched the dildo disappear between her large tits, and while he tried to rationalise that being jealous of a sex toy was dumb, he couldn't help it. He struggled lightly as his cock swelled against the cage and precum oozed out, he heard Christy ask lustfully "Remember that mold we took of your clit Tiffany, back when it was a cock, before we locked you up? Where do you think it is right now"

Realization struck and Tiffany screamed and complained into the gag, tugging at his bonds in frustration. It wasn't fair! He was being forced to watch his fake cock disappear between his girlfriends tits like he used to do with his actual cock, while his actual cock throbbed uselessly and painfully in a tiny metal prison, oozing precum. While he watched the show and desperately wished himself to trade places with the dido, his panting turned into half-sobs of frustration as his bonds held tight, and he and the dildo didn't swap places.

Tara had laughed at the revelation and continued to smile as she watched him squirm, struggle, and beg. Now she was annoyed that he seemed to be giving up so she flicked him hard in the balls, her fingernail making an odd noise as it connected with him. Tiffany's whole body shook as he tried to jump bringing more laughter from both women. "Let me show you how it works properly Tiffany" Christy purred and turned side on. Tara started to narrate the events, certain that Tiffany was paying attention.

"It's pressure activated" Christy licked the tip gently, then sloppily ran her tongue around the whole head of the dildo. Moans from Tiffany.

"We've decided to allow you to only use your mouth to build that pressure" Christy slowly slid the head of the dildo in and out her mouth. Louder moans from Tiffany

"You need to keep a good vacuum or you'll lose pressure" Christy sucked hard on the head. Tiffany was starting to groan now, his cock continuing to throb painfully against its prison.

"To build pressure you must pump the slide in the middle" Christy swallowed 1/3rd of the dildo and Tiffany saw that her lips were on the slide. She swallowed a bit more, then a bit more and Tiffany saw the slide moving with her mouth. Christy was breathing loudly through her nose now and clenching her thighs together as she swallowed more and more of the dildo until her nose was almost touching the button. Then in one smooth movement she brought it all the way out.

"Just once isn't enough" Christy proceeded to give the dildo an enthusiastic blowjob, pumping the slide in the middle with her mouth, but being careful to avoid hitting the button with her nose. She looked out of the corner of her eyes at Tiffany and saw his eyes flashing with jealousy and arousal as he watched. Some drool escaped from behind his gag, running down his chin to join his precum on the floor. Christy continued the blowjob as Tiffany grinded his hips in his bondage, trying desperately to get off, until a very faint buzz came from the dildo.

"Once enough pressure has been built, you press your nose against the button and it will dispense whatever is in the box." Christy slid the dildo all the way in until the balls were resting against her chin, and her nose was pressing the button. Tiffany noted with dismay that the dildo seemed to jerk a few times then stop.

"This one is for your gruel Tiffany" Tara snapped as Christy extracted the dildo from her mouth, wiping the drool from if over Tiffany's fake tits. Tara then took on a patronizing tone as she continued "There is a smaller one for your water. Don't worry your sissy head, we haven't forgotten how much you love drinking from the toilet, so we promise to only ever use toilet water, even when we're watering down your gruel".

Tiffany fought hard against his bondage at this, trying to shake his head in the posture collar and trying to thrash his limbs. He was heterosexual through and through, and he mentally resolved then and there that he would rather starve than suck on dildos for any reason. Smiling at each other the ladies spoke over him "I don't think she wants to baby" "Of course she does, she's just shy, you saw her clit leaking" "I suppose you're right, we could always...well it's the end of the month and we could add it in?" The conversation seemed natural, but Tiffany suspected it was rehearsed. The women were too methodical with him for random chance.

Christy laughed and smacked the dildo against the palm of her hand as if clapping. "Yes!" She squealed "We'll add it to the conditions of this months escape challenge!" Tiffany groaned loudly and sadly at this, having never even come close to winning the escape challenges in the 3 years he could remember. Tara picked up and with mock seriousness she spoke down to Tiffany and said "This will put a lot on the line this month, so we'll need to raise the challenge to meet the stakes" eliciting another sad groan and garbled begging from Tiffany.

"Oh stop pouting sissy!" Christy snapped. "Honestly we give you every opportunity to control your fate, and you whinge and bitch when you make the wrong choice". Tiffany yelled into his gag at this, pointlessly trying to get Christy to understand that he wasn't choosing, he was losing rigged games. The more Tiffany complained and begged, the more Christy loved it, and the more Christy wanted to torture him. She balled up her fist and punched him solidly in his balls, loving the power it gave her over him. Tiffany's reaction almost made her cum as his whole body tensed and he let out huge sobs of pain from behind his gag.

Tara smiled as she watched and felt her own passions building, Christy's cruelty had continue to grow with Tara's encouragement and Tara was happy with her progress. "Ok my love, plenty of time for that later. We need to let the maid do her work, our house won't clean itself" Through the pain Tiffany grimaced twice as hard at this, the memory of buying this place with Christy. Being tortured into signing it over completely to them, and ending up trapped in this living hell. He lost himself in the painful memories for a moment, wondering where, how, and why he'd ended up like he had. A soft cough brought him back to reality and he looked up at the women.

Christy looked at Tiffany expectantly, and Tara tapped her foot gently. Swallowing his pride and fearful of more torture Tiffany began to beg from behind his gag. Garbled pleas for his lingerie, his love of the colour pink, begging for his maids uniform and to serve them as their maid. When they finally relented he garbled a "Thank you Mistress" to each of them from behind his gag. He worshiped Christy's feet and Tara's ass cheeks and thanked them again for allowing him to serve.

As always the day passed slowly for Tiffany. He cleaned up the ladies plates, pots and pans from their dinner the night before and breakfast that morning with a toothbrush. Then he swept the house, taking almost 30 laborious trips to the bin outside as the dustpan filled up, the 5 steps out the back door bringing him just about to tears each time. Washing then hanging their towels was next, and in the time it took for the washing machine to finish he served as the ladies footstool. Finally he had to wash and hang all of his lingerie, the women used the cattle prod to motivate him to lick the large patches of his precum in each of his panties before hand washing them. He was still constantly summoned by the ladies for menial tasks and handing the remote to Tara at one stage he was reminded of his earlier days when he wasn't gagged to the extent he was now. He had snapped fairly intelligibly "it's fucking right there!" pointing to the remote not 30cm from her hand. That was when they'd introduced the "behavioural correction program" as they called it, and he'd cried himself to sleep in pain that night.

In bed that night, after locking Tiffany in his sleeping cage and locking his cell firmly shut, the women spoke about Tiffany's challenge the next day. They slowly stripped each other as they spoke, getting increasingly excited and aroused. When they were planning this game for Tiffany they got into their usual game of who could 'out cruel' the other, and as the competition wore on the idea for Tiffany's feeder was born as well as a huge difficulty curve for the upcoming rice game. The ladies were now naked and laying next to each other wondering aloud how Tiffany was going to react the following day. Christy slid down the bed and put her head between Tara's legs and alternated between teasing her clit, and long licks to taste her lover.

Tara was moaning loudly in pleasure as she felt Christy's tongue work her, and her mind continued to race as she thought about how Tiffany was going to react tomorrow when he saw all the extra's they thrown in. After no more than a couple of minutes Tara yelled loudly in pleasure, her whole body shook slightly as she tensed and relaxed over and over as she came. Sliding back up the bed Christy and Tara kissed passionately around their panting before Tara started to slide down the bed to return the favour. Christy stopped her a moment and reached across to her bedside table and withdrew something from her drawer. Tara looked quizzically at it then smiled evilly, it was a baby monitor. Tiffany was now going to hear ever bit of Christy's orgasm.

The next day they led Tiffany toward the barn and the cool air of the morning chilled him as he struggled to keep up in the 6" heels, hobble chain, tight pencil skirt, and weight on his balls. They didn't dress him as a maid for his escape challenges and besides his usual bondage, lingerie, and heels he wore a long, tight, pink pencil skirt that made it very difficult to kneel down and stand up, as well as a tight, pink silk blouse and todays wig was blonde pig-tails with pink ribbons. The leash they used whenever they led him around outside was a solid bar with a handle on one end, and a D-ring on the other. They would padlock the D-ring to the back of his posture collar and use it to keep him in front of them and guide him, while making sure he kept his distance. Given his bondage it wasn't necessary, but it reinforced his helplessness.

After what should have been a short walk they entered the barn, and with a loud bang the barn door closed behind them. Tiffany was pretty sure it was done for effect, as well as the delay between the door closing and the lights coming on, but they still worked to scare him and keep him off balance. The lights clicked on with an electric buzz and Tiffany groaned loudly, never quite acclimating to the site. The barn had long ago been modified into a maze, with twisting corridors, dead ends, and countless turns created by crates and shelves. At the start of the maze was a large area about 10 meters by 10 meters they called the "rice ring" that was reserved for the "rice game" as the ladies called it. Tiffany groaned again as he saw what must have been about 30kg of dyed rice piled up, with 6 different colours mixed in. He also saw 6 different sacks and 12 ropes handing from the rafters.

Tara's voice turned his attention away from the rice, she took a lot of pleasure in laying out the rules for his impossible challenges and Christy was only too happy to watch. "Now Tiffany, let me explain the rules of this game as they're a little different" He knew this challenge all too well as he had spent countless hours, many times before, trying to sort the rice into individual colour piles by hand. It was during these escape challenges he would normally be locked into the anti-run device, and crawling around with it squashing his balls would coat the rice in his precum, and along with the drool from his gag it made the rice stick together and to his legs causing him to really struggle to gather and separate the rice. Usually it was 3 colours with 2 hours to sort them, and he would always fail dismally.

Tara continued speaking and Tiffany's eyes widened as he realized how much harder it would be this time. 6 colours of rice would need to be organized into their piles by colour. Then he would have to fill a sack, tie it to a rope and pull it to the rafter. Sewn into the neck of each of the sacks was a small electronic swipe that in proximity to the correct lock on the rafter would cause a key to fall to the ground. There were 6 different locks for 6 different swipes, and only the paired one would work.

She further explained that a failed pairing would result in her emptying the sack onto the ground. He could either scoop it back up, or try another sack. A 2nd failed pairing would result in that sack being emptied over the 1st, and so on. She also threw a huge curveball and told him that although there were 6 sacks, there were only 5 keys so a failed pairing could mean the wrong swipe, or no key. Tiffany was distraught by this as he couldn't imagine any way he could ever possibly win, Tara noticed the slight slump and smiled as she continued talking. He would have 8 hours and could break at any time for food or a bathroom break. Food was a 30 min deduction and the toilet was a 10 min deduction, regardless of the time taken. She also gave her usual warning that any misbehaving on his part would be met with swift punishment.

"Now if you choose not to win sissy, we will allow you to continue to serve us for another month" He hated the way she phrased it "We'll also allow you to use your new feeder from now on" He softly grunted in anger which Tara noticed "and we'll even allow you to beg to suck your own cock before you eat and drink sissy!" She finished patronizingly. Blushing with shame and grumbling angrily into his gag Tiffany didn't see Tara move in close, but he felt her punch him in the balls and yelped into the gag in pain, a trail of drool running down his chin.

"If you don't want to hear your reward should you choose to win, then maybe your reward for winning the escape challenge should be the same as losing" Tiffany begged as he heard this, swaying his torso to try and shake his head 'no' got a huge laugh from Tara. "Well, ok sissy. Only because you look so pathetic" His cheeks burned red again with shame as she manipulated his reactions.

"If you win..." She left the sentence hanging heavy in the air until Tiffany was practically whimpering in anticipation "I'll give you this key" His cell key. "and this one" His cage key. Too many times these had been promised for Tiffany to get excited, he knew it was theatre. "Also these" The keyring holding the keys to his collar, cuffs and gag. "This one too" Tara accentuated the 'too' as she held up the key to his chastity. Despite knowing better Tiffany wanted that key more than anything, to be allowed to have an erection, to be allowed to orgasm! It was too much for him and he quivered.

"That's 4 rewards for 5 keys" Tara screwed up her face in mock thought, pressing a finger to her lips. Suddenly she flashed her huge smile and said brightly "I know! These ones too!" Holding up a set of unfamiliar keys Tiffany stared at them. They weren't the keys to the house, nor did they look like car keys. He was puzzling over them as Christy held up a a few sets of cuffs and shackles. Tiffany garbled into his gag not understanding and was silenced as Tara jingled the keys. "These are the keys to those cuffs, if you win then you can put them on us!" They had teased him countless times with this and similar taunts in the past when using the shock collar, but never had it been so real. Revenge on Tara for everything she had done! Drugging and manipulating Christy, trapping him in this nightmare. It could all end!

Tara watched his expression with interest, he was clearly desperate for his freedom but perhaps more desperate for revenge against her. She knew Tiffany hated her and she enjoyed how strong that aura of hate was. To be so helplessly enslaved by the person you hate more than anything or anyone else, forced to lick her ass cheeks, kiss her feet, lick her shoes clean. Tara felt herself starting to get very warm and wet from her train of thought and made an effort to remain in the moment.

"Ready to choose your fate sissy?" Tara snapped. Tiffany garbled an affirmative and Tara pressed a button on a clock that was similarly as loud, and slow as the one in his cell. "GO!" She yelled. As he slowly minced toward the rice ring Tara smirked at the bulge at the back of Tiffany's skirt. She absently reached down and rubbed her pussy as she watched the short, pained steps Tiffany took, knowing that under the skirt Tiffany's balls were being crushed by the parachute.

Tiffany minced into the ring and got as close as he could to the huge pile of rice, then dropped awkwardly to his knees. He then leaned forward until he toppled onto his hands and knees. Given how close to his collar his hands were kept it meant he was in a position as if waiting to be fucked doggy style. Christy whooped and cheered at this, her voice echoing "Yeah look at you slut! Ready to get fucked like a whore!" She yelled. "Doggy style for the little cock slut!"

Through his shame Tiffany vowed that once he was free the first thing he was going to do was fuck Christy in the ass, then make Tara lick his cock clean, and the more they yelled insults the more elaborate his dreams of revenge became. He plunged his hands wrist deep into the rice pile and tried his best to keep the drool out as he grabbed 2 handfuls. The long acrylic nails made it hard to clench his fists but after a short struggle he had some rice in his hands. He shuffled backwards and turned slightly, placing the pile on the ground and gently went through it finding the colours. Pink, purple, sky blue, black, white, and red.

"That's 1 hour already sissy!" Tara yelled. Tiffany sat bolt upright, his high heels pressing hard into his ass cheeks and stared in shock at Tara. It couldn't possibly be an hour already! The mean laughter from the ladies answered his concern, she was lying. Grumbling to himself he was going to make her play the rice game, with rice he'd soaked in his piss! He crawled slowly and painfully with a handful of rice and left tiny little piles. It meant move movement for him, and he silently apologised to his balls, but widely separated piles would help in the long run.

As Tiffany worked Christy and Tara swapped looks of increasing lust as the watched. His face screwing up in pain as he slowly crawled, the grunts of pain and noises of the kettle-bell against the floor making them go weak at the knees. They watched as he would pause and glare at his hands, frustrated by the acrylic nails. He would constantly lose all his momentum to clear them of rice, and this was made doubly difficult when he started coating piles of rice in his drool and precum. At one point he stopped completely and the ladies could see his shoulders moving as he sobbed. Christy moaned as she watched Tiffany torture himself in a game he couldn't possibly win, and Tara was again discreetly rubbing herself.

Over the next 2 hours Tiffany worked slowly but diligently. He tried to stay focused as he worked but eventually he begged for a bathroom break. Christy put his collar on him and led him out of the barn to his bathroom, which was an outhouse left over from the properties past. The inside had been painted pink with a Barbie motif, and they made sure to keep the coarsest toilet paper they could in there. After cleaning him up Christy led him back to the barn and when they entered Thomas saw he had only taken 3 minutes. He screamed in his mind that it wasn't fair he was being penalized the extra 7 minutes, but he knew the women wouldn't care.

He grunted and groaned as he struggled and after another hour of crawling back and forth he finally finished separating the rice. It was just in time as his poor balls couldn't take any more, he had to rest. The loud, slow tick from the clock fraying his nerves as he was reminded how much time he was wasting, and a few times he went to move only to stop short because of the pain. While he rested he checked himself as best he could for stray bits of rice, as previous experience taught him the women would destroy his piles if they found rice on him. After 15 minutes he was satisfied he was rice free and decided to ask the ladies to inspect the piles.

He grunted into his gag as he struggled to his feet, his arms flailing uselessly in their cuffs. The hobble chain and pencil skirt combined with his cuffed hands made it nearly impossible but eventually he was upright. Tiffany then garbled loudly into his gag and did his best to curtsy, signalling to the women he was ready for his rice to be checked and the ladies wandered over to inspect his work. Tiffany tried not to stare as both women were panting slightly, a bit flushed, and their hair was messy. He tried not to think about them kissing and groping each other as he suffered, but he couldn't help it.

For 30 long minutes the women inspected the rice looking for errors but to their genuine surprise they didn't find any. Tiffany would normally make at least 1 mistake in the rice game and they loved the look of sadness and defeated as they pointed out his mistake before undoing his hard work and mixing 2 or even 3 piles of rice back together. While the ladies sifted through the rice Tiffany began to daydream about escape and revenge again. He stared off into space and imagined all the things he was going to do to Tara, and how much he was going to enjoy Christy's body again.

The ladies finished inspecting the rice and noticed Tiffany staring off into space, so they quietly walked away and left him to his daydream. After another 10 minutes Tiffany realized he was alone in the rice ring and cursed himself for allowing his mind to wander, he wanted revenge but he'd need to win the rice game to get it!

Over the next hour Tiffany carried the empty sacks over and slowly filled them with rice. While he was normally fairly quick at this the acrylic nails now slowed down his every action, and he had to constantly clear his nails of drool and precum coated rice. He was panting and lathered in sweat by the time he had finished when his stomach growled loudly reminding him how hungry he was. He again struggled to his feet, did his best curtsy and garbled into his gag. Tara walked over and Tiffany garbled into his gag again and tried to gesture with his hands.

She watched him for a minute before she mockingly asked "does the little sissy want some yummy gruel?" Tiffany sighed and garbled a "yes Mistress, thank you Mistress" in return. Tara stalked off towards the house and when she returned she was almost chatty as she took off her shoes. "You know sissy, you don't know how lucky you are. Most other owners would have made their property fetch their own food. Yet here I am, at your beck and call and serving you lunch" She huffed in mock outrage and it was all Tiffany could do to not rolls his eyes. It did take him a long few seconds to thank her again, which she picked up on.

Dropping the gruel on the floor instead of a bowl got a groan from Tiffany and a moan from Christy. Looking at her lover with evil in her eyes Tara lifted her foot and dropped it with great drama into the gruel. Really squishing it into the ground and mushing it up between her toes, rubbing her foot so it coated the sole. Christy moaned loudly enough to echo slightly through the barn, and she rubbed her thighs against each other as she watched Tara humiliate Tiffany. Tara clicked her fingers and pointed at the ground and Tiffany, fearful of his meal being made worse that it already was, immediately dropped to his knees.

Steadying herself with a hand on a box Tara lifted her leg until her foot was face height to Tiffany she gave him a good look. Tiffany eyed her dirty foot and the gruel that now coated it, having picked up more dirt from the barn floor. He could see old bits of straw, dust, dirt, and God knows what else. He garbled into his gag and Tara laughed, but her eyes were cold. "You may beg me now Sissy" and beg he did. Muffled by the gag he begged to be allowed to lick his food from her dirty foot, and how much he'd enjoy it.

Minutes passed as he continued to beg, Tara was only half listening as she was watching Christy play with herself as she watched the display. One hand cupping her tits and squeezing her nipples, the other between her legs stroking her pussy over her shorts. Smiling Tara bent down and attached a small wingnut to the nut on the screw that protruded from the front of Tiffany's gag. She twisted it over and over and heard increasingly grateful noises from Tiffany. She eventually unlocked the multiple locks on the gag with gag key from the reward pile.

She moved it around in his mouth gathering up drool while watching Christy, then with her foot directly below his mouth she slid it out causing drool to cascade all over the top of her foot. She then lifted her foot and shook more drool from the gag onto her sole. Christy was moaning loudly now as she watched, her hands had slid underneath her clothing as she played with herself. She was careful not to expose herself to Tiffany, and knowing she was keeping him denied added to her arousal.

Christy pinched her nipples one after the other and ran her finger gently over her pussy, gathering juices before she lightly toyed with her clit. Still watching Christy heard Tara snap "Lick", click her fingers and point at her foot. Tiffany, not seeing any other options to eat, started licking her foot for all he was worth. Long slurps up her soles, along her arches. Working his tongue in between each toe and sucking on each as he worked hard to get as much food as he could. Twice more she stomped on the gruel and had him repeat the process until she gave him permission to lick up the scraps from the floor. "Don't forget your disgusting drool on top of my foot sissy" Tara snapped.

His mouth already felt foul from the barn floor and dirt on Tara's foot, but he was too scared not to obey and as he licked he thought about the gag they made him wear. He was usually ungagged 3 times per day for his gruel and toilet water, otherwise he could spend up to 23 hours a day gagged. His jaw and tongue didn't hurt anymore when he was gagged, but when it was removed they would ache terribly as movement brought feeling back. The gag itself was a hot pink, custom made ball-gag, the top 2/3rd's of it was a firm compound that would still flex slightly under his teeth. He suspected it was some kind of silicone or rubber, or combination of the two and it could be enlarged.

The bottom 1/3rd was stainless steel with an extendable flange for immobilizing and crushing the tongue. The flange and inflation were controlled by a nut and screw in the front that Tiffany couldn't quite see, but many times he had run his fingers over and around it trying and failing to deflate the cruel device. Tara and Christy had taken great pleasure in showing him a close up picture of the nut and its virtually smooth surface, punctuated by a couple of discreet notches, and explaining it was compatible with just 1 wingnut that they owned.

Once Tara's foot was free of drool she lifted her other foot, black with dirt. She snapped her finger again "Lick, sissy maid". Tiffany looked at the rice then at her foot, too scared to risk asking a question with his voice he looked hesitant. Tara held up the remote to his parachute and clicked it a few times causing him to yelp in pain as she zapped his already aching balls, and Tara was amazed at how much more satisfying she found his screams without the gag.

"Lick, bitch" She snapped, and he did. Conscious of the time he was wasting he did his best to keep saliva in his mouth and he licked and sucked until her foot was clean. Tara held up the gag "Open up bitch". Tiffany shook his head slightly, and planning to beg for it to stay out he opened his mouth. With a laugh Christy pushed the button on her remote 3 times in a row, the sudden zaps of pain to Tiffany's balls made him open his mouth and yelp loudly in pain. Tara pounced and shoved the ball roughly into his mouth then shifted her grip to the straps. She took 2 quick steps so she was behind him and placed her knee in his back.

Regardless of whether he was compliant or resistant to the gag, he was gagged like this every time since he had made the mistake of trying to keep the gag out of his mouth. The women had responded by changing the way they gagged him to this rougher, more painful method. They loved introducing punishments to him for bad behaviour, then keeping the punishments permanent even when his behaviour improved. "It's a reminder for our sissy maid to be more obedient" they'd told him, phrasing it as though he was in on it and the maid was someone else. It infuriated him.

Digging her knee in sharply Tara pulled hard on the straps, buckling the strap below his ears then the one above them. Reaching around she grabbed the inverted Y shaped strap that ran up either side of his nose, then joined and ran up between his eyes and over the wig on his head to join the other straps at the back. Once they were all buckled tightly she then pulled each one an extra centimetre and thread a padlock through the hole. With a series of clicks that echoed heavily in Tiffany's ears Tara produced the wingnut and smiled cruelly.

She held up her remote to his parachute in one hand and raised an eyebrow slightly at him. "Go ahead and fight" She dared him as she placed the wingnut on the screw and begun to twist. Tiffany's begging was quickly garbled as he felt his jaw stretching to accommodate the ever increasing ball, and his tongue being compressed so far down and back he thought it would block his windpipe. Moaning sadly as he watched Tara remove the wingnut and drop it down the front of her shorts, she suddenly smiled and wiped up a big glob of her juices then wiped it across Tiffany's nose. "Back to your game, bitch" She laughed.

His cock throbbed hard in its cage as Tara's scent filled his nose. Although he hated her, he loved the way she smelled. His high heels echoed around the barn as he minced back to his piles of rice, the noise drowning out the slide of the kettle bell and his own groans of lust and pain. The smell of Tara was making his cock ooze precum into his G-string and made it difficult for him to concentrate as he spent a minute trying to figure out the best way to approach the next part of the challenge. Eventually he decided to just go for pot luck. He reasoned that he still had plenty of time up his sleeve if he made a wrong choice, so he could recover.

Picking a sack at random he minced over and fought against his shackles as he tried to reach down to grab it, but after a few attempts he realized he would have to kneel to grab it. He groaned softly in frustration as his knees were already aching, and kneeling and standing were both extremely difficult in his attire and bondage. He grunted in pain and frustration as he dropped awkwardly down and grabbed one of the sacks, and he then realized that with the weight of the sack, and with his diminished strength he would have to drag the sack along the floor. He was dismayed at just how difficult the ladies had made the challenge for him and he almost burst into tears as he dragged the sack.

It took a lot of effort but eventually Tiffany had the sack underneath the ropes. He was sweating and panting heavily through his nose, and Tara's sweet smell drove him mad. He was beyond desperate to win, he needed those keys! He needed to be free! He stared into the rafters and examined the sack trying to get some kind of hint as to which rope he should tie it to, but the sack looked just like a sack and the rafters were dark. Tiffany's skin suddenly went cold as he wondered if Tara had lied about the keys.

He wouldn't put it past her, she was beyond cruel. Tiffany started to work himself into a panic as he imagined Tara laughing at him and telling him there were no keys to begin with. He was on the verge of tears again when he managed to regain his composure and rationalized that nothing was lost by trying, when he ran into another problem. In his past life with Christy any light BDSM they did ended with ropes being cut, Tiffany didn't know how to tie a knot that could be untied.

He screamed in frustration into his gag, the noise was garbled and muffled but the women heard it. Christy and Tara stopped kissing and fondling and looked over at him curiously. Christy whispered to Tara who giggled in return and they watched with interest as Tiffany fumbled with the rope for about 5 minutes. He twisted and pulled and tried his best to recreate a truckers knot, and many other half forgotten knots from movies. He eventually remembered a lasso and managed to tie it and get it looped and cinched around the next of the sack.

Tiffany panted as he struggled into position in front of a dangling rope, took a few deep breaths then awkwardly began to pull the rope. They were tiny movements as his 10cm wrist chain interfered with his movements, but the rope was moving surprisingly easily. Too easily. Tiffany groaned again in frustration as he let go of the rope and saw a different, empty rope slither back toward the floor. It took a few minutes of shuffling and testing but eventually he found the right rope and began to pull in earnest.

For the 3 years Tiffany had been off the drugs Tara had used to enslave him, he wasn't exercised properly. His diet kept him healthy, but there was nothing in it to promote or maintain muscle mass. He knew it was done deliberately and had no doubt that by now the women were likely stronger than he was, but he wasn't prepared for how much of a struggle it was to lift a 5kg sack the 7 metres or so to the rafters. He grunted and strained as he pulled, sliding the sack up a handful of centimetres at a time before his chain would pull taught and he would have to awkwardly move his hands to keep pulling. It felt like a hundred years to Tiffany before the sack hit the pulley and swung from the rafters.

Tara had pulled out her phone as Tiffany started lifting and now that the sack was in the rafters, she pressed a few buttons on the app she was running followed by the unmistakable sound of a key hitting the cement floor. During the competition to out cruel each other Christy had come up with the idea of the keys and Tara had refined it. There were swipes in the sacks but they would only let the app know which mechanism it was close to, and the mechanisms in the rafters holding the keys were unlocked remotely via blue-tooth. Tara had pinned Christy's arms down as she explained her plan to have Tiffany get the first key, fail, then be rewarded with another key, over and over until his time ran out. As Tara spoke Christy moaned and squirmed in pleasure until she orgasmed just from the thought of torturing Tiffany.

The sound of the key hitting the cement floor was better than Christmas morning to Tiffany. There really were keys! He could possibly win this time! His cheeks burned red with shame and anger as he thought of the feeder they wanted him to use and he doubled his efforts. He still didn't know which sack was for which rope and decided to pair a sack with a rope he felt 'lucky' about. It caused his knees and balls considerable pain over the next 30 minutes and he soaked his G-string in precum, like is was being squeezed out of him but eventually he had the remaining 5 sacks tied off.

He had good momentum now as his excitement grew. Every movement was bringing him closer to winning his freedom! He grabbed a rope and as he struggled to lift the sack, he imagined his life after winning. Inch by inch the sack rose. He was going to tie Tara's head to his cock for at least an hour, until his balls were completely empty. Higher and higher the sack went. Then he was going to lock her in his sleeping cage and cuff Christy to the bed. The sack was almost at the rafters now. He was going to spend hours with his hands and tongue getting reacquainted with Christy's body, her big tits that always felt so good in his hands, her nipples that would harden up in his mouth, and how soft and warm her tits felt around his cock.

Tiffany had lost himself in his fantasy and barely noticed when he couldn't tug on the rope any more. His fantasy came crashing down when he heard a cough behind him and he realized he couldn't tug anymore. He desperately scanned the ground but didn't see a key, and he didn't remember hearing a key fall. Tara smirked as she saw realization hit him and she pointed up at the sack then down at the ground. Tiffany garbled sadly into his gag as he lowered the sack, begging her not to empty it, begging her for mercy. As with everything they inflicted on him, Tara ignored his pleas. Once the sack was on the floor she uncinched the lasso then gave him an odd smile.

Tiffany had a moment of hope when he saw the smile, maybe she was going to take pity on him after all. That hope was smashed as Tara picked up the sack and spun a few pirouettes, emptying the sack in a few large circles. Tiffany moaned sadly in defeat into his gag, his eyes reflecting how sad and hopeless he felt as he watched all his hard work upended on the floor. Christy was sitting in her chair holding the arm rests tightly and as she watched she was rubbing her thighs together and moaning quietly. Tara looked up at her and gave her a wink and a wicked smile before approaching Tiffany.

Tiffany was almost crying again as he stared at the rice on the floor, torn between wanting to clean it up now or try his luck again and he didn't notice Tara come up behind him. She knelt down and grabbed the D-ring on the back of his collar tightly, then tugged it a few times to get Tiffany's attention. He garbled in panic into his gag and he heard Tara snap "What do you say sissy?" Tiffany was confused by the question and garbled a questioning noise. Tara drew back her free hand and punched him solidly in the balls. Tiffany screamed in agony into his gag, countered by a loud moan of pleasure from Christy as she approached another hands-free orgasm from his torture.

"You say, sissy, 'Thank you Mistress Tara for helping me correct my mistake'" Thomas was in absolute agony from the first punch and wasn't listening. His balls were already throbbing in pain from his hours playing the rice game, and were extremely tender to the touch. The solid punch Tara had given them was by no means a particularly hard punch, but it was well placed to get both of his testicles at once and given they were already so tender it hurt 10 times worse. After a moment of listening to him garble incoherently Tara drew her arm back and gave his balls another solid punch, softer this time but enough to make Tiffany scream in agony again. Christy was panting and squirming in her chair as she watched.

"Thank You Mistress Tara!" She almost shouted at him, and he garbled the sentence back to her. She slapped his balls causing another scream of pain "For helping me correct my mistake!" Through his groans of pain Thomas repeated the line in his gagged garble. She grabbed his balls and started to squeeze, the cloth of his skirt pulled tightly over them. Harder and harder she squeezed causing a near constant stream of pained begging noises from Tiffany, he struggled and tried to escape the torture but Tara held tight to the back of his collar. Christy was gripping the chair so tightly her knuckles had turned white, and she was moaning with every breath and grinding her hips in the chair now.

"Are you a sissy little bitch?" She snapped. Tiffany garbled affirmative noises and in response Tara relaxed her grip on his balls for a second, before she tightened her grip even harder than it had been. She almost burst out laughing as the noise of relief from Tiffany caught in his throat and became a loud groan of pain. The women had learned long ago that no matter how hard they squeezed, eventually the pain would dull down. Squeezing hard, relaxing the grip, then squeezing again kept the pain fresh and current, and so Tara started rhythmically squeezing hard, then relaxing her grip.

Tiffany's hands flailed uselessly in their cuffs and although he tugged against the D-ring the chain was fed through, it held fast. His breathing was ragged and he groaned in pain and begged for mercy with each breath. Tara forcefully turned him until he could see Christy squirming on her chair and fighting her desire to rub her clit. Christy stared at Tiffany and watched as his face screwed up in pain, she heard him groan and beg and struggle before being given a moments respite, only for the pain to come back.

She moaned loudly in pleasure, on the absolute edge of an orgasm and missed what Tara said to Tiffany. After watching Tara give his balls another squeeze though she heard Tiffany garble something. "Clearer!" She heard Tara snap at him. Tiffany garbled again a bit more clearly, and the pain in his voice was a lot sharper. "Again!" Tara yelled at him. Then Christy heard him well enough to understand him, Tara was making him say "I'm your sissy little bitch" over and over as she tortured his balls. It was too much for Christy and she felt herself tip over the edge. She let out a long scream as her whole body tensed and quivered while wave after wave of pleasure washed over her as she orgasmed.

Tiffany watched Christy orgasm, hands free, to the site of him being tortured and humiliated and a few tears escaped his eyes. He didn't know what had happened to bring Christy to this point, but before he could consider it he felt Tara squeeze his balls one more time before she let them go and she almost ran over to Christy. Tiffany doubled over as he knelt there, tugging on his wrist chain trying to cup and protect his balls even though he knew he had no choice but to kneel there as he recovered. He heard faint noises and looked up to see the women kissing and groping each other excitedly. Still moaning from the pain he watched as the women got more urgent with their kissing and groping, he saw their tank tops begin to slide up, and saw Tara put her hand down the front of Christy's shorts.

He tried to control his breathing and his noises, but the pain he felt made that impossible. He didn't want to alert the women to his watching, he was hoping desperately to catch a glimpse of some hidden skin. After 5 minutes his balls had settled down to a painful ache, and after 10 minutes he finally noticed that the women kept glancing slyly at him as they kept themselves covered. They had set him up with a distraction and he had fallen for it. Cursing to himself he turned away and started to gather the rice. He used his hands like a bulldozer as he crawled and in about 10 minutes he had the rice contained in a small area.

He decided to put it back in the sack now as he not willing to risk another colour of rice being mixed in, and after another 10 minutes he had the rice in the sack and was eyeing the remaining ropes. He picked one at random and, as he was exhausted now, he struggled harder than ever to raise it. While stealing glances Christy noticed how defeated Tiffany looked, she suggested to Tara that he be given another key and Tara happily agreed. When the sack finally reached the rafters Tiffany was rewarded by the sound of another key hitting the ground, and the women had to stifle their giggles when they heard the happy noises he made.

His throat was dry from panting and his skin was lathered in sweat, he was dying for a drink but didn't want to take the time. Then he heard the key drop. '2 keys!' Tiffany yelled in his mind. He was getting very excited now and he glanced quickly at the clock and saw he still had 45 minutes to get the 3 remaining keys. He couldn't help but feel a surge of hope and excitement while he crawled to the next rope. As he tiredly tugged on the rope, raising the sack centimetre by excruciating centimetre he couldn't help but feel hopeful about winning. 'Only 3 keys and the better part of an hour, come on!' He encouraged himself, willing his tired muscles to work harder until he felt the sudden resistance of the sack hitting the pulleys at the rafter.

The low creak of the pulley taunted him as no key fell, and he felt his hope slipping away when Tara approached. She removed the lasso and picked up the sack. Tiffany felt a sob catch in his throat as he begged her not to, but as always his begging was ignored. Tara held eye contact with him and scattered a random pattern on the floor with the rice, making sure to spread it out as far as she could. Tiffany screamed and railed in his mind against her cruelty. 'Why couldn't she empty the bag in a pile? Why did she have to empty it at all?!' He yelled in his mind. He heard faint moans of pleasure from Christy again and groaned sadly.

Tiffany was in a panic as he worked to gather the rice back up, the loud clock constantly driving home that his challenge time ebbing away. He moved as fast as he could but his knees and his balls couldn't take it anymore, he had to stop and try to recover. He looked at the clock and saw that Tara had taken about 2 minutes to empty the sack, this late every second would count for him. '43 minutes' He thought to himself. He decided to rest for 5 minutes and try again.

After 5 long minutes he tried to move but his knees and balls were still too sore, so he continued to wait. The clock seemed to tick louder now and to Tiffany's panicked mind it sounded like it was taunting him as he spent time doing nothing. After another agonizingly slow 5 minutes Tiffany tried to move again. His whole body was complaining now as his arms were exhausted, his legs and especially his knees were sore, and his balls were still throbbing in pain, but he was able to inch himself to the next sack. It seemed to take a lifetime but finally he was at the rope and starting to pull.

Tiffany panted hard and his arms shook and buckled as he struggled heavily with the sack. He dropped it twice and grunted as he started again. It took all his strength to lift the sack up to his chest height and his arms wobbled even more as he tried to hold his grip while repositioning his hands to keep pulling. Out of the blue Tiffany felt his parachute zap him painfully in the balls 5 times in a row signalling the end of his time. The zaps caused him to drop the sack and collapse heavily onto his side and with each zap Tiffany's whole body shook and he yelled in pain. His arms flailed and tugged uselessly at his cuffs and his legs curled up under his ass cheeks as he desperately sought some reprieve from the pain.

He was crying by the time the Christy and Tara got to him and it took them a minute to get his attention. "Time's up sissy, you've made your choice!" Christy announced happily, almost clapping in excitement. "I'm so happy you decided to continue to serve us!" Tiffany garbled into his gag making confused and negative noises. He tried to shake his head but the posture collar still held firm. "You look confused sissy" Tara taunted. "Do you think you still have time on the clock?" Tiffany garbled loudly in the affirmative and Tara rolled her eyes. Exasperated she huffed "Ok, let's run through the numbers".

Tara ran through almost all of his actions and the time they all took, making sure to taunt him about his daydreaming at the start and getting distracted by their show near the finish. Eventually she had gotten to 7 hours, with 1 hour remaining. Tiffany was certain now that they'd made a mistake and he'd be allowed back in to try and finish. "Lunch is usually a 30 minute deduction" Tara announced, catching Tiffany off guard. 'Usually?' He began to worry. "But since you're such a useless sissy bitch, you took 32 minutes taking you to an hour for lunch".

'An hour!?' Tiffany garbled argumentatively into his gag. 'That's not fucking fair!' He tried to scream. He continued to make argumentative noises from behind his gag while the ladies exchanged glances until finally Tara grabbed Tiffany's collar with both hands and Christy punched him in the balls. They laughed to each other as Tiffany's angry garbles instantly changed to a high pitched howl of pain followed by him begging fairly clearly "no no no". The feeling Christy got from being in complete control of Tiffany, torturing, and humiliating him was like a force of nature, she couldn't help herself and punched him in the balls again and moaned as she heard him scream harder.

"Repeat after me sissy" Christy snapped and pressed a finger into his balls threateningly. Thomas groaned in pain with each breath and squirmed as he felt a finger press against his balls, but he heard Christy say "Thank you Mistress Christy, and thank You Mistress Tara". He repeated the line through his gag and Christy slapped him in the balls making him scream again. She didn't know herself how it happened, but making Tiffany scream as she tortured his balls made her so wet and horny she could barely stand it. With her voice thick with arousal she continued "For allowing me to choose my fate". Tiffany was sobbing in pain, tears running down his face but he did his best to repeat the line.
Christy then started to squeeze Tiffany's balls the same way Tara had earlier, a long hard squeeze followed by a brief moment of no pressure. Tiffany wailed into his gag and tried to thrash around, but Tara held his collar firmly. Christy rolled him from his side to his stomach and sat on his thighs then continued her squeeze torture. She knew from research and experience that she had to be careful as too hard a squeeze for too long could rupture her favourite thing to torture. Alternatively if she didn't squeeze hard enough to keep the pain high then Tiffany could orgasm from the torture, which was unthinkable.

Christy grinded her hips as though she was fucking Tiffany's thighs, her moans of pleasure got louder and closer as her orgasm built up quickly. After causing 30 seconds of unbearable pain to Tiffany, Christy had another hands free orgasm. She gripped his balls hard and while he wailed in pain she screamed and moaned in pleasure over and over until she finally collapsed on his back sweating and panting. She put her head next to his and in between pants she croaked out "Let's get you back inside Tiffany"

The ladies gave him 10 minutes to recover from Christy's torture before they attached his collar and guided him out of the barn. Tiffany winced and grunted in pain with each step, but his eyes never stopped darting around. He heard the women talking to each other about him and listened with half an ear, but in his mind as he looked around he imagined running over the hill to freedom, or hiding in the clump of trees until he could make his escape. Every direction promised freedom, but the collar, bondage, and especially the kettle bell kept him a prisoner.

He started to resist as they approached the house, both because of the 5 steps leading into the house and also because he did not want another month of this hell. The women spoke louder and to him now, catching his attention. "We gave you a choice sissy and you chose" "Don't complain because you're having buyers remorse" "You know you'll love it, that's why you chose it". He garbled into his gag and flailed his arms, trying to fight against going back into the house until he felt a finger press against his balls. He yelped and jumped and heard Tara snap "Up those stairs sissy, move it!"

Thomas rolled and twisted in his hateful sleeping cage, trying desperately to find a comfortable position against the bars and the hessian when a noise made him jump. They had turned on the baby monitor and he could hear them kissing and talking. He was too tired to completely pick who was speaking, but the words made him dread tomorrow. "I can't wait to see her big, fat lips working on her feeder!" "I can't wait until she see's the surprise in the bottom!" "We are going to have so much fun tomorrow!" There was no more talking after that and instead Thomas had to suffer through 30 minutes of listening to the women orgasm over and over, his own cock throbbed painfully hard against his chastity and oozed out precum onto the hessian. He eventually fell into a fitful sleep full of nightmares about what the following day would bring.

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