Recruiting of a Sissy Maid Ch. 02

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Chantel, begins her orientation and training.
5.8k words
4.58
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Part 2 of the 16 part series

Updated 06/08/2023
Created 09/18/2017
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Chapter Two: Onto Her Training and Breaking Down.

The feeling of fear and dread falls over Chantel as she sits on the flimsy bed in what is for now her prison cell. Totally alone and isolated except for the fact that Mitch and Nate Burrows will lord over her as they orientate, train and ultimately break Chantel from a fantasy sissy to what will be a living sissy life, ready to then be sold off into sissy slavery to a syndicate or business that has use for said sissies.

As she sits she scans this damp dreary room, she finds that time will be a lot of what she has. At first she is able to occupy her mind with an abundance of thoughts and memories. The constant fear of what Mitch and Nate will do to her in order to break her into this sissy lifestyle. She soon resigns herself to laying on the beaten up mattress and tries to get some sleep. Figuring that sleep will be an ally for her own mind and soul.

Sleep eventually comes...

Waking up hours later with some growing hunger pains, Chantel realizes her situation again. Having no clock or windows she has already lost track of time. The growing gnawing pain of her hunger is a tool to feel she has been here for some time though. She gets up standing in her heels as she must, the cameras constantly monitor her, as she walks to the water cooler and drinks a glass of water hoping it will satiate her hunger, it does not do much.

She walks around the room first looking at the filthy excuse of a shower and the enema station. She walks to the sink and to her makeup table. She looks at the various video cameras, a weird feeling of being observed at all times comes over her. She then walks up to this bondage bench set up, it looks like a big sawhorse and she fumbles around with the leather straps.

She says to herself, "This does not look like a fun device Chan... What have you done to put yourself in this situation?"

Resigned to her fate she walks back to her bed and sits, hunger continues to gnaw at her, she so wishes she will be soon fed. Sighing she lays back on her bed, bent at her knees her legs and heels sit on the floor and her back flat on the ratty mattress as she stares at dim, dark, filthy ceiling. She so wants to fall back to sleep as it only gives her comfort but her hunger and mind refuses to let her go back to sleep.

She hears noises from the cell door as she sits up in interest, part of her wants to see Mitch or Nate, but another does not out of fear of what they may do to her. The slide over the 8" x 8" window is uncovered.

Mitch stands, looks in and asks, "Hey Chantel, do you want to eat?"

She is sitting up and replies, "Excuse me Master?"

He repeats, "Do you want to eat, bitch? Get up now and over here if you want to eat."

She gets up and scampers in her heels and click clock with abandon to stand before Mitch, she curtsies and says, "Yes, please Master, I want to eat please?"

Mitch pulls open the larger slot and slides a tray inside, on it is a bowl of what appears to be clumpy, cold, rubbery gruel and a mug of black coffee. He says, "Take the tray if you want food."

She smirks a cold smirk as she see's the food, well what appears too be food, but she is so hungry she takes the tray in hand, stands back and curtsies saying, "Thank you Master Mitch."

Mitch replies, "You have 5 minutes to eat, so don't waste time."

She curtsies and says, "Thank you Master." and scampers to her bed to begin to eat this bland meal and drink what is cold mug of old black coffee. Mitch closes the window and she is alone. As disgusting as this meal is, Chantel is too hungry to complain and she quickly stuffs her mouth with the gruel and washes it down with the cold black coffee. Her hunger pains subside as she burps and finishes just in time as Mitch comes back and demands the tray with mug and bowl. Chantel quickly gives it back him, curtsies and thanks him again. Mitch closes the window up and she is alone again.

Chantel feels better for the gnawing edge of hunger is gone but for some reason she is very tired and soon as she gets back on her bed she passes out. It seems that Mitch and Nate have spiked her food and she will be out for many hours.

They both come back with a lady friend and check to see if Chantel is out. They open the door and the three of them come in and the lady friend has a professional grade laser removing system for hair. They will have this lady give Chantel a full body laser hair removal treatment. Chantel being passed out should make it more easier. Mitch and Nate remove Chantel's bra and the pull off her shoes, pantyhose and panty. They watch Linda begin the treatment, it takes about an hour or so to give Chantel her first treatment.

Linda tells them that Chantel will probably need 2 more over 3 or 4 weeks. They wrap things up and all walk out as they thank Linda for her service. Chantel remains passed out, left naked on her bed.

[many hours pass by].

Chantel groans and moans as she begins to come around, wondering what the Hell happened. She next see's she is naked and as such confused. She begins to look at herself and feels weird, but she picks up her bra and puts it back on then her panty. She then grabs her black sheer pantyhose and slips on each leg carefully. She looks at a camera and then puts on her black high heel pumps and sits on the edge of the bed, head in hands, and still confused.

She gets up and feels the urge to use the toilet, she walks to it, pulls her pantyhose and panty down and sits to do her business, it's so weird as cameras watch this and it's embarrassing to do what most people do in private, but bodily functions force her to this this. Once done and cleaned up she pulls her panty and pantyhose back up and walks back to her bed as she sits.

Her mind is foggy as she sits, time ticks away. She wishes she could talk to people, even Mitch and Nate would be good right now.

She looks at one video camera, knowing the room is mic'd she asks, "Would somebody please talk with me? It's so lonely in here... Master Mitch, Master Nate, please will either or both of you talk with me?"

There is only silence.

Chantel realizes that neither are available or will talk with her at the moment, so she lays on her bed and cries as she takes her fingers and scratches the wall of the root cellar, drawing imaginary pictures. Life becoming a broken sissy maid and slut will be harder than she thought and currently thinks, not like her fantasy mind played as she would jerk off too her then fantasies. So as such she does begin to play with herself and it gives her a distraction and her mind plays and fantasizes as she pulls on her sissy dick. For the next number of minutes she is in a pleasurable state and then she ejaculates, staining her panty. Her joy of climax though quickly subsides as she comes back down. She gets up and with her hands washes the cum from her panty and then sits back on her bed.

She lays back down and is soon able to finaly fall back asleep.

Time ticks away...

Again Chantel wakes up and still sees her situation. Her distress grows, she wanted to be broken and groomed for soon to be sissy enslavement, but now experiencing such incredibly hard effects of this programming she is weary. She no longer has any idea of how long she has been locked in this dreary room. Hunger again begins its reminder to her stomach.

She hears noise from the door, nervousness and excitement rises in Chantel as she sits back up on the edge of her bed to wait to see what will next happen. The door opens and she sees Mitch and Nate enter the room, ironically she smiles but remains quiet like a mouse.

Mitch says, "Stand up Chantel."

Of course she does as she is told, curtsies and asks, "What does Masters Mitch and Nate request of or plan for me."

Mitch says, "Go to the bondage bench and pull it out from the corner."

Chantel nervously does as she is told and struggles to pull it out with her in her 5 inch spike heels.

Nate says, "Go to it and strap your ankles in girl, NOW!"

Chantel resigned to knowing something is up and likely not to be pleasant. As she straddles the bench, and wraps the leather cuff around her ankles.

Nate says, "Bend over the padding and place your hands in the wrist cuffs."

She does as she is told, Nate cinches the cuffs top tightly, Chantel is in unescapable bondage and is helpless to what will soon be done to her. Her nerves rise as this is not the most comfortable position for her to be in.

Nate says, "It's time for some serious grooming of this faggot sissy girl."

Mitch says, "Yep, it's time."

Chantel hears all but knows nothing of what the plan is. However she now feels Mitch's hands on her bottom, feeling her backside as he pulls down her black pantyhose and then her black satin panty. Her bottom now fully exposed and defenceless.

Mitch leans to Chantel and says, "It's time to fuck your ass."

She waits as he takes a tube of lube and dollops an amount on his fingers and begins to lube up Chantel's butt hole, which feels quite good to her and she revels such by gracefully moaning. Nate laughs as he says she enjoys the finger job.

Mitch once done is undoing his pants and then dropping them along with his briefs revealing his nice 8 inch cut white cock. He gets behind Chantel and with Nate capturing video he begins to insert his cock inside Chantel's virginal ass as she groans in wincing pain to his forceful invasion. He does not waste much time with some hard thrusting and Chantel cries in pain as Mitch forces his tool deeper and harder up her ass.

Mitch says, "It feels good, nice and tight, she's a good fuck." as he keeps banging her backside, the men revel in Chantel's virginal cries. They have so little regard for her cries as the goal is to completely break her will so that she will be a docile, dutiful sissy and slut to her soon to be new owners. Mitch keeps pumping his cock until he grunts out aloud and shoots his thick streams of hot cum up her sissy butt hole. Then he pulls out and stands back as he does his briefs and pants back up.

Mitch says, "Good girl... It's your turn Nate, have at the sissy's ass."

They swap positions as Mitch now records Nate getting at Chantel's little ass.

Nate pulls his pants down and his briefs as his hard 8 inch cut white cock is ready and hunting for Chantel's butt hole.

He says, "This is gonna be fun girl. I love breaking in sissy ass."

Nate the more aggressive brother pushes his meat hard up Chantel's ass as she cries in pain tears begin to fall from her eyes. He pushes harder and harder as he gets a strong pumping rhythm going, each thrust causes her to wince in pain but she takes it as she must. The pain and the feeling of cock on her prostate causes her to get hard too and Nate knows how to make her get going, his cock rubs her prostate. Soon they both groan and moan as Nate reaches his orgasm virtually in time with Chantel's and he fills her back side with his hot cum as she sprays out her sissy cum onto the floor. He pulls out and fixes his clothes.

He bends to her face and says, "You liked that did ya honey."

She with tears says, "Yes, Master, thank you both."

She stays tied up and next, comes something other than a good butt fucking, something she will dread.

Nate says, "Lets get at what she needs next Mitch."

Mitch says, "Go at it brother, do what you do best."

Chantel in bondage hears all but has no idea of what will happen. Nate walks out of the room for a moment, then back in, in his hand is a long thin cane. He whirls it in the air as Chantel's eyes go wide with dread. She knows she is about too be caned.

She interjects, "Please no...please no...Masters..I'll be good, please no, please do not cane me."

LAUGHTER! by both Mitch and Nate as they comment to each other of how their sissy girl is begging to not be caned, but they say to each other that will not stop it."

Mitch says, "You see Chantel, your obstinance, your desire to control a situation that you have no business in controlling, your defiance. That is why you will be caned."

She cries and begs more and more, only making Mitch and Nate want to cane her ass more and more. She stops crying for the moment, tears have made her mascara run as she waits for this event to begin.

Mitch records this on video as he says, "Chantel, you will count after each strike Master Nate gives you, you will thank him and ask for another, do you understand?"

She replies, "Yes Master."

Nate behind her backside is excited as he whirls the cane around the sound scares the Hell out of Chantel. He takes the cane and lays it on her ass, slides it up and down as she perks her bottom up.

Nate says, "OK girl you ready because here we go."

The whirl and crack of the cane on Chantel's ass strikes her as she winces in pain and cries out, "One...ohhh...oohhh...ahhh, thank you Master...ahhh may I please have another?"

Nate delivers a firm second strike and Chantel twitches her ass in her bondage as she cries, "Ahh two...huh...ahhhh..oooh..thank you Master...oooh may I please have another?"

Mitch laughs Nate delivers a strong crack of the cane on her sissy ass, she cries, "Oohh...Ooohhh...ahhhh...three...oooh..oohhh, thank you Master...ooohh, oooh may I please have another?"

Nate delivers crack after crack of the cane, driving Chantel into excruciating pain and she begs to stop but that only makes Nate more angry, so she keeps counting and asking for more. By the tenth crack her ass is red and welts are clearly visible. She fights her restraints as she cries.

Mitch says, "We will stop at ten, this time girl. Next time will be more."

Chantel looks at Mitch, mascara runs as she says, "Thank you Masters."

They undo her restraints and she gets up her ass is burning in pain as she stumbles to her bed and falls on it on her stomach as her bare ass does not want to touch anything except air. Mitch and Nate laugh at their pathetic sissy slave girl. Mitch tells Chantel, it's all a part of breaking her and she will be broken of will when they are done. All she can do is muffle out in her pillow a, "Thank you Masters."

They leave and lock the door as she lays in bed and suffers in silence. She is in no way wanting to move, only to lay in pain, her mind wanders as she desires only to sleep. Which does come slowly.


Untold number of hours pass by, Chantel awakes mostly out of growing hunger pains. She is still on her stomach as she carefully runs her hands over her still sore buttocks. The pain is still there but has subsided a bit. She rolls out of bed carefully not to sit on her bottom. She carefully pulls her panty back up and then her pantyhose. She gingerly walks around rubbing her bottom with her hands. She so wants to know how long has she been kept here, her gnawing hunger gives her some idea that it must be a few days. She feels the urge to use the toilet and carefully seats herself onto the toilet, it's not comfortable she does her business.

She keeps walking around this room in her heels, drinks a few glasses of water from her cooler but her hunger grows. She kneels on her bed not wanting to sit on her bottom. She thinks, God please somebody talk to me. God please somebody feed me.

The door then has it's window open as Master Nate stands outside and says, "Food for you sissy. Do you want some?"

She gets up and scampers in her heels, she expects more gruel and old cold coffee, but she does not care, "Yes please." she says.

Nate slides the tray through the slot and Chantel sees its not gruel but a number of slices of plain drying out bread and a mug of coffee. She grabs the tray, curtsies and thanks Master Nate.

"You have 10 minutes to eat, don't say we do not care for you." he says.

Chantel says, "Thank you Master." as she places the tray on her makeup table and begins to eat standing up.

Nate laughs and asks, "What is the matter sissy? your bottom still sore?"

She replies, "Yes Master, but it's a good type of sore Master." trying to appease Nate's dominance over her.

Chantel chokes down the drying out bread, gulping the cold black coffee to make it easier. The bread only does slightly ease her hunger pains but she does not complain. Once finished she returns the tray to Nate and he tells here, "Undress and get ready for an enema then a shower."

She curtsies and says, "Yes Master."

Chantel strips nude and moves to the enema station and gives herself an enema. She is told to hold the water for 10 minutes. It's hard for her to do this. Once Nate tells her she can evacuate the water she thrusts over the toilet and flushes herself out. She is then told to stand under the shower head and wait for the water to come on. She scrambles and jumps as it's cold water and she can barely handle it, but she must wash herself and endure the cold water. Once done she towels off and is to put her panty, bra and pantyhose back on. She is to redo her makeup and then wait for further instructions.

Time then ticks by as she lays on her bed and tries to sleep but can't for now. She gets back up and in her heels she walks around crying out it's so boring, I'm lost in here can anyone please talk to me?

NOTHING!

She cries in her bed as she lays and does eventually drift in and out of sleep.

[Many more hours pass by.]

The cell door opens up and she springs up out of bed. Masters Mitch and Nate enter. Mitch instructs her to strap herself back to the bondage bench. Chantel falls to her knees before him and begs him not to. Mitch slaps her face and tells her to follow commands. She resigns herself to her fate and soon is strapped back to the bench. Nate puts a hood over her blinding her and then puts on noise canceling headphones. Chantel is in total sensor depravation and is very scared by this. What is to happen next is what she thinks. Another caning? She hopes not...

Mitch and Nate bring in a group of men who will each have their way sexually with Chantel, her only sensations will be stiff cock in her mouth and up her backside. The first two men come at her the first guy works up her ass and she is perked up by the weird feeling of such as he gets his cock inside her. Then the second guy stuffs his cock in her mouth. Chantel is lost into sensory depravation, but knows she's being face fucked and butt fucked. It's so weird a she can't see, nor hear anything but feels the invasion by these men! These men pound her mouth and back side until each ejaculates and she gets it without knowing or hearing such.

This group fuck goes on 4 more times, 5 butt fucks and 5 face fucks all in total sensory depravation. Cum has run down her legs and a bit spilled from her mouth. It then stops and she is left alone for now in depravation. She has no clue what may happen next and her emotions are high with fear.

Thankfully for Chantel, the headphones are removed and the hood his too, the joy to hear and see again is refreshing and she thanks her Masters. She thanks the men for the sex too. But now she see's what is next, Nate and his cane. She trembles and tears flow, she knows to beg will not stop this so she waits in silence.

Mitch tells her to again count each strike and thank her Master while asking for more Mitch tells her she will get 15 strikes.

Nate begins as he strikes her ass hard with his cane, she cries, "Ooohh...one...ahhhh...thank you Master...oooh may I please have another?" as she squirms her bottom.

The second strike, she cries, "Ooooh...ahhh...two...ooooh..thank you Master...may I please have another?"

Nate gives her a strong third strike, she yelps and squirms, "Ahh..hahhh..oooh..three..ahhh..ooh thank you Master..may I..oh please have another?"

Nate goes on each strike sends Chantel closer to mental breakdown, she squirms in her restraints but counts off and asks for more. But by the 11th. strike she all but gives up.

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