Enslaved Sissy Maid an Erotica Story
Jeff didn’t want to do this, it was the last thing he wanted, but after he was evicted from his house he had little choice in the matter. He approached the near mansion of his ex, a slightly bitter and dominant woman named Madeline, of course she knew he had fallen on hard times, she always kept tabs on him and when he was in his hour of need she offered him a job as their home’s cleaner.
Of course Jeff denied the pity job, not even wanting to see Madeline anymore, let alone work for her, but he was officially homeless now and had nowhere else to go. He waited outside of the mansion for nearly three hours, but eventually he couldn’t wait anymore he approached the front door, slowly knocking three times in a row. He was completely unaware that this was the last time he’d ever see outside of the house again.
In less than a minute the nude Madeline swung open the door, standing in the door frame with a wide, nearly sadistic, grin. Jeff always hated that about her, she was a nudist and preferred to be completely naked, even around other guys. “Well well well, Mr. I don’t need charity finally came to his senses” she giggled, eyeing up his tattered and dirty clothing before motioning for him to come inside.
The inside was even more impressive than the outside, lush red carpets, sturdy oak furniture, plenty of bottles of champagne, and the biggest TV Jeff had ever seen. He knew that Madeline’s new husband was a rich stockbroker, so the pair nearly had enough money between them to buy a country. He felt the cool air against his sweaty body, finally getting out of the blazing sun after three days spent standing in it. “So Jeff, let me give you a quick tour” Madeline came from behind him, wearing a simple bathrobe now, clearly she just derobed to tease him.
She walked him over to his room, a small closet with nothing inside but a single sized bed and a small nightstand, located under the stairs as if he was Harry Potter. Jeff didn’t really expect much better than this though and shrugged it off for now. “Now, if you’ll follow me to the kitchen, we can go over your contract” she shut the door to his small room immediately, not letting him see the array of maid’s uniforms that were hung up above the bed.
He nodded again, still silent and followed her into the kitchen, where her husband Chuck was waiting. Jeff gulped nervously, knowing all too well that Chuck despised him “oh...hey uh...Chuck” Jeff awkwardly greeted him, speaking for the first time since he arrived.
The muscular man just grunted in response, Madeline motioned for Jeff to sit across from Chuck while she went and sat on Chuck’s lap, lightly stroking his hair. “Now then Jeff, if you are going to work for us there’s a few ground rules we have to set up” she immediately got to business, to which Jeff nodded “number one, you are NOT allowed to cum ANYWHERE in our mansion, we don’t want your stink to fill our home” she snapped immediately, catching him off guard.
Before he could fully wrap his head around that rule she dove right into the next “number two, you are to dress as WE see fit, in the uniform WE provide, even on your off day” the fact that she only said day and not days was already telling of how this would go “number three, in order to agree to this position, you must sign this contract” she motioned to the enormous stack of papers on the table.
Jeff eyed them, thinking they must be a couple hundred pages long, between the length of it, the fact that he didn’t have any other choice, and the fact that the couple stared at him intently meant he just immediately signed it without even giving it much of a read. Madeline immediately grinned from ear to ear, snapping her fingers as another man whacked Jeff over the head, knocking him out cold.
By the time Jeff came to, he was strapped to a table, the room was spinning around him wildly. Slowly he picked his head up which was the only part of himself that he could move and looked down at the horror in front of him. He got up just in time to watch Madeline lock the key to the contraption around his shaft. It looked almost like a cock ring, but had spiked edges on both sides.
“Ah, Justine! You’re awake” Madeline giggled, Jeff didn’t quite get what she meant, not that he knew how to respond anyway. “Welcome to your new life! This little toy here will make sure you follow rule number one, if your cock gets hard enough to the point where you might cum, it will hit the sharp edges, don’t worry though they aren’t sharp enough to draw blood or seriously hurt, just hurt enough to keep you distracted from your pleasure” she giggled, stating it all matter of factly.
It took a moment, but Jeff also noticed an IV in his arm, which Madeline motioned to next “I’m sure you might have noticed, but that IV there is slowly putting all sorts of chemicals inside of your body, don’t worry though, it’s just to alter your physique to make your body slim and feminine, but you will be keeping your cock” she grinned evily, flicking his member with her index finger.
Jeff was so confused, he didn’t even know where to begin, “You can’t do this to me!” was the only thing that came out, in a slightly higher pitch than normal. “Actually yes I can, you signed a legally binding contract agreeing to all one hundred and thirty five rules of our home...it’s not our fault that you didn’t actually read them” she giggled yet again, clearly enjoying this so much already that Jeff couldn’t tell if she was getting off on it.
“Since it’s your first day, we’ll make things easy for you” she said, undoing the straps that held Jeff to the table. She then bent down, pulling out a slutty maid’s uniform, a skirt so high that Jeff knew his cock would be visible, fishnet stockings, a black choker, two relatively small golden hoop earrings, a pair of cuff like the ones playboy bunnies wear, a top that went only barely over the nipples, and insanely high ballet heels. “Get dressed, and remember, always walk with a sexy little sway in your hips, bend over only at the waist to show us your cute little ass, and DON’T cum” Madeline rambled on a bit longer before getting up and walking out of the room.
Jeff eyed the clothing, unable to believe what in the world he had gotten himself into. But at the threat of that ring activating he slipped into the ill fitting clothing, which was far too tight in every single way. After getting dressed she walked out of the room, seeing Madeline and walking passed her, but before she even got three feet Madeline took his hand, pulling him over to a chair and slinging Jeff over her knee “I warned you, walk with a sway in your hips!” she yelled, slamming her hand down as hard as she could onto his ass, making him yelp in surprise as the sharp smack immediately turn the cheek bright red.
She followed that smack up with three more on each cheek before practically throwing him off of her knee, knocking Jeff onto the ground. “Now get up, walk to the kitchen, and fetch me my tea” she ordered in an aggressive tone. At fear of another spanking Jeff shot to his feet, bowed and walked towards the kitchen, making sure to over exaggerate the swaying of his hips, placing one foot directly in front of the other.
As soon as he got into the kitchen though he was met by Chuck, who had a strange looking thing in his hand with straps on it, wordlessly he shoved it into Jeff’s mouth, hooking it behind the back of his head. It was a strange tube of some kind, that blocked off his teeth and forced him to keep his mouth wide open. “Sit you damn slut” Chuck barked, pushing on Jeff’s shoulders hard, forcing him to the ground.
He was so confused, looking up at Chuck, trying to ask what was going on before he undid his belt, pulling out his cock. He grabbed the back of Jeff’s head, pushing the wide open mouth up to his cock, thrusting deep inside of Jeff’s throat. He immediately gagged, tasting the musk as it filled up his throat, pushing even deeper inside, down into the back of his mouth.
Chuck groaned happily, beginning to slowly buck his hips “yeah you dirty slut, take it all in” he mumbled, gripping Jeff’s hair harshly, pulling it to push Jeff’s nose into his pubes, forcing the whole shaft down his throat. He repeated this process for nearly five minutes, accommodating Jeff’s throat to his girth and length before quickly pulling out and cumming all over Jeff’s face, to which he was hardly able to close his eyes in time.
“Whew… you make a good fuck doll Justine” he laughed, unhooking the gag from his mouth and walking away. Jeff fell to all fours, coughing and wiping the hot sticky spunk from his face, it took him nearly ten minutes to wipe it all off and process what had just happened. He then went and grabbed the tea, bringing it back out to Madeline.
“Oh Justine… we really are going to have to work on your speed I asked for that tea nearly fifteen minutes ago” she looked pissed “But Maddy your damn psycho husband decided he need to fuck my face!” Jeff snapped back. Madeline instantly got up out of her seat, yanking Jeff over by his hair to the chair, giving him a good ten more spankings “You will refer to us as Mistress and Master! And you will thank your master for his wonderful seed! Seed that you so ungracefully wasted I might add! Rule number one hundred and one, if your Master cums in or around your mouth, you have to drink it ALL, NO exceptions!” she shouted, spanking him at least five more times before pulling out a needle and injecting it into his butt. “There we go, that will be your real punishment, that concoction should speed up the rate in which the chemicals make your ass plump up.
Madeline sighed and let Jeff fall to the ground, rubbing his rear which stung greatly. “Alright Justine, go and shower up, then come straight here understood?” she ordered, crossing her arms, leaving her legs a bit spread open, letting Jeff see her bare pussy. He simply nodded, walking over to the shower, still rubbing his ass.
Once Jeff stripped and got in the shower, he couldn’t help but feel a bit horny, after all of the chemicals, seeing Madeline again after this time being single, even getting an eye of her womanhood, he just couldn’t help himself. He lightly reached down to touch his cock, but the moment it grew in size the spines dug in, making him yelp out loud. Instantly he covered his mouth, knowing that Madeline heard him. In a panic he started cleaning himself off, hoping that she would just ignore it, but much to his dismay, she heard.
The bathroom door swung open, Madeline stood there in the nude “Justine! Were you touching yourself?!” she yelled firmly, to which Jeff simply ignored her. He couldn’t ignore her for long though as she flung the shower curtain open and stepped inside, pushing Jeff onto the tub floor, grabbing his hair and pulling his mouth and nose up to her crotch “Lick… now, and if you cum in my shower Chuck will feed your dick to the hounds!” she was fuming mad.
Jeff recognized the taste and smell of her lower regions, from back when they were dating, but this time he had no intent of licking her, it had only been a half hour and he had already been punished twice! He wasn’t going to just go along with it forever. At this disobedience though Madeline smirked “Oooohhh I’m going to have so much fun whipping that defiance out of your eyes my little slave~” she giggled, a hint of psychotic evil underneath her happy exterior.
She pushed Jeff to the ground “want to play it that way? Fine, you’ll lick my pussy when your done in the shower, or else you won’t get ANY food today OR tomorrow young lady!” she snapped, getting out of the shower and slamming the door behind her.
True to her word, after Justine got out of the shower and walked into the kitchen, only two plates were set out for Madeline and her husband. “Justine, you have one more chance, get under this damn table and eat me out, or else you don’t get any dinner” she threatened. The sight of the steak they were eating was undeniably making Jeff hungry, especially since he hadn’t eaten much the last couple of days.
He nodded slowly, awkwardly getting down onto all fours and crawling under the table, crawling right up to Madeline’s chair, whose legs were spread and waiting for him to start. He gingerly stuck out his tongue, forcing it into Madeline’s wet pussy, lightly tonguing at it over and over again. All the while Madeline went about a normal conversation at the dinner table. Talking about Jeff as if he wasn’t there, saying his ass was too small, he wasn’t good at eating her out, his dick was tiny, all sorts of things just to piss him off.
But Jeff was too hungry, he ignored her insults and kept licking away. It took nearly fifteen minutes of Jeff’s tongue going to work but eventually Madeline let out a small moan, pushing her thighs together and wrapping her legs around Jeff’s head, squirting all inside of his mouth and all over his face.
As soon as she was done she practically kicked him away, pushing him into Chuck’s chair. “She’s been a good girl now~ babe would you mind giving her some dinner?” Madeline giggled. Chuck nodded in response, dragging Jeff out from underneath the table and positioning him on the ground. Chuck pulled his rock hard dick out again, gripping Jeff’s hair and furiously pounding into his throat again.
After another intense forced blowjob Jeff was left on the dining room floor, covered in a mixture of his owner’s cum, laying back, panting heavily. Madeline approached her coughing, panting, maid grinning down at him “Alright Justine, for tonight, we’re going to have you sleep in our room, but don’t you dare get used to it” she smirked, grabbing Jeff’s arm harshly and yanking him over her shoulder.
As they entered the enormous lavishly decorated master bedroom, Chuck was already waiting inside, holding a few things that didn’t look very pleasing to Jeff. Madeline threw Jeff onto the ground with a bit of force, knocking the wind out of him and leaving him dazed for a moment. In that moment Chuck bent down, wrapping Jeff’s legs together with a thick brown rope.
By the time Jeff caught his breath back he was already flipped over again, Chuck firmly tying his wrists, elbows, and forearms together. All the while Madeline took another roll of rope, tying his knees and thighs together, slightly squishing against his trapped cock and balls.
The maid wiggled worthlessly on the ground, trying in vain to free his arms and legs from the ropes, but it was completely useless. His struggling stopped the moment his mistress stepped in front of him though, completely taken aback by what she had in hand.
She held up a massive dildo, with a couple of straps on the back end of it. It’s girth and length put both Chuck’s and Jeff’s dicks to shame, it had to be at least eleven inches long if not more and was so thick Jeff wasn’t sure if it would fit in any hole. On top of it all, it was covered in thick veins to simulate a real cock, even the tip seemed to be open, but for what purpose he didn’t know.
“Now then Justine, you can either open up nice and wide and accept your new toy into your throat, or your master can pry your cute little jaw open and I’ll force it down, so take your pick” Madeline grinned sadistically. Jeff could hear his ‘master’ cracking his knuckles from behind him.
In a moment of regrettable submission Jeff opened his mouth as far as it could open, but even then it wasn’t prepared for what was to come. Madeline rammed the enormous toy down Jeff’s throat in one hard thrust, immediately making him gag as it slid past his tongue, right down deep into his throat. His eyes watered instantly as he tried to accommodate himself to the enormous size.
By pure instinct he tried to spit the goliath out but his mistress was too fast and buckled it at the back of his head, leaving it trapped inside of his throat with no where else to go. He was then swiftly flipped back over to laying on his back, and pushed underneath the enormous King sized bed.
Without saying another word Chuck and Madeline got into the bed and no more than five minutes later Jeff could hear the bed creaking. Madeline’s sexual sultry voice moaned out as Chuck’s short satisfied grunts instantly let Jeff know what they were doing up there.
The moans and creaks filled Jeff’s ears, arousing him more than once, making his ring painfully jab into him time and time again. It took nearly thirty minutes before Madeline cried out once more, screaming in pure pleasure as she orgasmed with her husband.
The sensations were maddening, Jeff’s cock hardened time and time again, his body felt the need for release but the pain of the ring prevented him from being able to fully grow erect leaving him in a trapped state of constant sexual deprivation. Before long he even found himself bucking his hips, sucking the enormous cock in his throat for all that he was worth, desperate to get some kind of release after the day he had.
He was so caught up in trying to get off that he didn’t even hear his owners get out bed, making it even more of a surprise when he was yanked out from under the bed by his feet. “Well well well, looks like someone has been enjoying herself~” a sweaty Madeline giggled. Jeff could see she was holding up to her womanhood, it almost looked like a funnel.
At the same time Chuck had his cock lodged in a strange tube, lightly grunting as it seemed to milk his cock dry, dispensing it all into a large container. Madeline took a separate tube, connected to the same container, and attached it to the funnel, letting her own cum drain into it. “Don’t worry dear, we know that you’re probably really thirsty, after all, at dinner you had such a massive pound of meat but hardly had anything to drink~” she teased, motioning to the container again.
The two milked themselves dry, filling up the nearly quart container of cum. A hollow pit formed in Jeff’s stomach, the memory of the opening in the head of the dildo lodged down his throat coming to mind. “Oh-hohoho~ looks like you caught on~” Madeline couldn’t help but laugh like some kind of evil villain, staring at Jeff’s shocked expression.
Jeff tried in vain to crawl away, back under the bed, but was swiftly pulled out again. Madeline grabbed the tube at the end of the shaft in his mouth, attaching the container to it, locking it in place before shoving him back under the bed. “Nighty nighty Justine~” she waved goodbye, before getting back into bed with her husband, cuddling to sleep.
Jeff was kept awake nearly all night, having to focus on keeping down the nearly unending flow of cum that filled his throat and poured down into his stomach, filling him to the brim, as if he had eaten seven meals in one sitting. But eventually the well ran dry, allowing him to get about three hours of sleep before started over again.
The next three months continued mostly the same cycle, Jeff would wake up, get dressed, serve and service his master and mistress all day long, would get a small meal and whole massive cup of cum, before being bound and left in his room all night long with an IV in his arms, pumping him full of female hormones.
After those three months his hair had grown out considerably, growing down to his upper back. The hormones also did their magic, making his hips grow wide, his thighs thick, and his ass plumper than ever, which Chuck had constantly made all too apparent by groping and rubbing every chance he got.
Justine’s voice had even grown slightly higher as well, his adam’s apple having shrunk slightly. If it weren’t for the obvious cock that was almost always sticking out then he could easily be confused for a beautiful woman. Not that he was given many chances to speak, he almost always had an open gag in his mouth, just in case Chuck needed any relief at any one given moment.
Throughout this time his masters had been developing many more mischievous schemes, until one day their latest sexy invention was completed. “Oh Justine!~ come hereee!~” Madeline called out, and in record time Justine came strutting by, her hips having torn almost all of her skirts wide open.
Before Justine even fully turned the corner, Madeline was on top of him, a strange mask in hand, she stuck it to his face. The thing felt strange and cold, covering his entire visage, eyes included in a sticky black sheen. He couldn’t see a thing until Madeline fiddled around with some settings, causing the mask to change shape, gripping his face hard and seeming to rearrange it’s appearance.
He tried to pull at the thing, but it wouldn’t come off, he tried to yell and ask what was going on, but he still had a gag keeping his lips spread open. Madeline grinned happier than Justine had ever seen right as his vision came back, Madeline held a mirror up to his face so he could see why she was so ecstatic.
Looking back at him in the mirror wasn’t Jeff, nor was it even Justine’s altered face, it was the face of a literal super model. Not just an attractive face, no, he recognized this face “it’s perfect isn’t it Justine? Chuck and I both agreed that it was a lot harder to get going while you looked like yourself, so we invented this mask! Using it we can make you look like ANYONE else in the world!” she giggled and laughed over and over again, pulling out a thick black collar with a red leather leash, attaching it to Justine’s neck and dragging her out into the living room.
She messed with the mask’s features again, and before long Justine looked like her mistress! “Perfect!, see, I don’t do Oral but Chuck LOVES getting his dick sucked, so I’d imagine this anniversary present will make him quite happy~” she giggled, rustling Justine’s long hair.
She tied the leash to a large pole right beside him, walking around behind him and chaining his feet to the wall. Then she pulled out two more chains, hooking them into the ground just in front of him, wrapping his arms up as well, leaving him bent over on all fours.
Madeline then walked over to the chair right in front of Justine, looking her maid up and down. “How long has it been now? Since you’ve last came? Over three months right? I’d wager you’re about to explode~” she giggled, yanking off her robe, letting her nude form show to her trapped maid.
With a sadistic grin and light touch she let out a sultry moan, her fingers sliding inside of herself. Justine groaned, feeling the ring dig into him once more. His mistress was completely right, he was about ready to explode at a moment’s notice, he was so horny all the time. He couldn’t help but dream of Chuck fucking his virgin asshole, of Madeline thrusting a strap on down his throat, all he ever thought of now was getting off no matter what but the damned ring prevented him from coming much closer at all.
Madeline messed with the remote to Justine’s mask, forcing him to cock his head up and open his eyes, staring right at his mistress. “We can also use the mask to control where you look~” she grinned devilishly before returning her fingers back inside of herself. She slid in two at first, lightly stroking and fingering herself, grabbing at her bare chest with her free hand.
After a minute of that she slid another one in, letting out a lust-filled whimper of pleasure, enough to send a chill down Justine’s spine. At this point the ring was almost permanently digging into his cock.
It didn’t help when Chuck arrived home only moments later, coming in through the door and immediately catching onto what was happening. For just about the first time since Justine arrive he saw Chuck smile. “Happy anniversary babe~” Madeline moaned out, turning her head to look at him, while still fingering herself in front of Justine.
He didn’t say a word, just kept smiling, walking up to Justine, who still had Madeline’s face, dropping his pants and exposing his cock, longer and thicker than it had ever been before. Madeline pressed a button on the remote and Justine felt his neck extend forward, taking in a part of Chuck’s massive cock into his mouth.
Madeline got up out of the chair, moving to her husband’s side, messing with the remote some more, making their slutty maid’s head bob back and forth, making it feel more like a real blowjob instead of the usual sex doll approach they had been using.
Chuck cocked his head back, his cock growing even long in Justine’s mouth, making her gag as he head forcefully moved forward, taking in more of it’s enormous length. The remote made him pick up speed, his cock growing so hard that the ring pressed deeper into it than ever before, causing a feminine groan to escape his throat, only making Chuck start to thrust his hips as well due to the voice sounding like his own wife moaning.
Justine tried to close his eyes, but the mask kept them open, and forced him to stare up at Madeline, who currently was pushing her tongue into Chuck’s mouth. The desire was too much too bear, he moaned louder and louder onto the cock, his tongue going to work on it, fully giving Chuck the best blowjob he could ever imagine.
By now Chuck had pushed his cock so far down Justine’s throat that his nose was pressed right up against his pubes, before being pulled back three inches and them slammed all the way back in. After these months though, Justine’s gag reflex was completely gone, and he managed to lick and suck the cock as it was thrusting back and forth, along with his own head.
The thrusting and sucking only grew more and more intense, Justine’s eyes being drawn down to Madeline’s fingers returning inside of herself, her own juices getting all over Chuck’s toned leg due to how close they were. The moans of all three of them filled the room for nearly fifteen minutes before Chuck finally came, shooting his entire load into Justine’s throat, pouring in like a flood during a hurricane.
Justine hungrily slurped it all up, feeling his cock press harder and harder than ever before against the ring. He was completely surprised though, when Chuck kept on thrusting, grabbing Justine’s hair and forcing his cock to continue going as it rehardened again, ready to shoot another load down his throat.
Justine couldn’t help but let his mind wander at this point, thinking back to how he got here, trapped and bound, his body irreversibly changed, his throat being filled with a man’s cock, and himself being unable to cum despite constant sexual stimulation. He knew deep down that this was all payback from his ex, he should hate her, but in the moment all he could think about was how sexy she was, and how sexy her husband was.
He wanted nothing more than for either one of them to fill him to the brim, to unload all of their cum inside of him, he wanted nothing more than to become a woman in his lust, to get penetrated by Chuck, or to get eaten out by Madeline. It frustrated him to no end that he knew it would never happen, he was their slave, SHE was their slave. She only existed as their cum dumpster, to help their marriage, to serve them hand and foot, and scarily enough, she was starting to like it.
She wouldn’t even think about escaping anymore, her sole goal in life was to finally cum no matter what it costed her. If only she could get this damn ring off of her cock, then she could finally get the release she so desperately craved. But all thoughts of that were pushed out of her mind when her master unleashed another massive load of the cum she had come to love inside of her throat, which she happily drank up.