Recruiting of a Sissy Maid Ch. 04

Chapter Four: Chantel, Fitting Into Her New Lifestyle.

Master Holt says, as the two of them walk out from the elevator on the 2nd floor, "This will be the floor that you will begin your life in servitude to us Chantel. Lets go find your head maid Penny and then get you to your room."

Chantel grows more and more resigned to this new life as she see's a very well oiled machine as she says, "Yes Master Holt, thank you Master Holt."

The two of them walk the hall of the 2nd floor and out from a room comes two sissy maids. They are sissy Nikki Kincaid (34y.o.) and sissy Trish Travers (41y.o.). Both of them in black maids dresses, black pantyhose and black spike heel pumps. They see Master Holt and greet him with a curtsey each. Master Holt introduces them to Chantel and all three smile and greet each other.

Master Holt asks, "Have either of you two seen Maid Penny?"

Both reply that she was prepping room number 205 for Chantel's arrival. So off Master Holt and Chantel goes to room 205. Once arriving they find Maid Penny and introduce her to Chantel. Maid Penny has the room all ready, clean sheets, a closet with Chantel's newly arrived clothes and high heels as well as a dresser filled with clothes too. A makeup mirror on a desk and chair.

Master Holt explains the new quarters, "Chantel this is your new quarters, it's modest at 8 feet x 14 feet, but it has all you need to live here. We even give you a modest hi-fi and an internet connection monitored by us of course. You will find that we do look out for you sissy girls in return for your devotion to servitude to us. Is that correct Maid Penny?"

Maid Penny replies, "Oh yes Master Holt, we are well looked after as sissy maids Chantel."

Master Holt goes on to have maid Penny get me set up, changed into one of my maids dresses and on my way to my new daily life here.

After Master Holt leaves, Maid Penny goes over the details of Chantel's room and then has her change to one of her black maids dresses. As Chantel gets out of her current dress Maid Penny gets her more info as to life here for her now.

Chantel then pulls on a pair of white sheer pantyhose as Maid Penny says all new girls wear white pantyhose their first day as a maid. Chantel puts on a white petticoat then her black satin maids dress with white lace trim and a white satin apron with white lace trim. She puts on a black satin and white lace maids cap and steps into a pair of white 5 inch spike heel pumps. She now looks the part of one of The Jade Maid Club, sissy maids.

Maid Penny was told that sissy Chantel will be taken to the basement commercial cleaning room where the contract of washing, drying and pressing/ironing clothes from area businesses is being completed by the maids. So on the way they both go. Walking to the elevator they pass by a few other sissy maids, sissy Karly (28y.o.), sissy Lynda (46y.o.) and sissies Candace and Megan Moffit (both age 29), the club's identical sissy twins. It was all very interesting and cool to begin meeting other sissy maids. It helps build normalcy for Chantel.

They get on the elevator and ride it down to the basement. Once there and getting off the elevator they walk the hall until they enter the commercial grade laundry facility. Maid Penny takes Chantel to one of the male minder staff who overlooks and controls the area, Master Wilson Smith (33 y.o.)

Maid Penny says as she curtsies, "Good afternoon Master Wilson, I'd like to introduce our new girl, sissy Chantel."

Master Wilson looks Chantel over and enjoys what he sees, "Well, this is our newest girl, welcome Chantel."

Chantel curtsies and says, "Thank you Master Wilson, it's an honour to meet and serve you Sir."

Master Wilson dismisses Maid Penny and then has Chantel follow him to the other girls, sissies, Marie Maples (33y.o.), Nikki Kincaid (45 y.o.) and Trish Travers (41 y.o.). He then has her start on sorting, inventorying and separating the laundry from the various area businesses that are contracted for commercial laundry of their laundry and once done then Chantel is to be given an opportunity to the other tasks, from putting laundry into the machines, removing laundry from the machines, putting laundry into the dryers and removing laundry from the dyers, to pressing and ironing and folding and repackaging cleaned laundry.

This will keep Chantel busy for the next remaining 3.5 hours before shift ends for the night. Chantel finds laundry keeps her busy and that shifts normally for girls scheduled to work for the club are typically 4 hours then 30 min. for lunch and then 4 more hours of work. The laundry is a bit monotonous, hot and tiring on high heeled feet but such is a sissy maids lament. Chantel enjoys chatting with the other girls as they all learn about her and she them. Master Wilson keeps them under control though. The power of one man as a Master over four sissy maids, is almost intoxicating to see from the point of view of a sissy.

By 5:00pm the shift ends, all girls are back at their quarters, sissy maids in the laundry, sissy maids who work in the warehouse that receives, inventories and ship out various sex toys, videos and magazines, the sissies who clean the building and offices of The Jade Maid Club, sissies who are out on day calls cleaning mostly businesses contracted The Jade Maid Club that enjoy having sissy maids clean for them and the luckiest girls are sent as sissy maids to clean houses of the well to do in the city who get off on sissy maids. They are all back by 5:00pm for their dinner time which is 30 minutes long.

All girls are now fed an appropriate diet of good but not too fancy foods, girls are all on a prescribed diet plan set up by the doctors who look after these girls and to help keep them in a proper but light as possible weight and fitness. The girls are able to socialize as they eat dinner. Chantel has yet to be assessed her diet, fitness and her hormone replacement levels as all sissy girls are being made into female hormone taking transsexuals. She will meet with the doctors tomorrow. She gets an average meal for tonight.

After the sissy girls have their dinner, they will be given their night time prostitution duties. Masters put up a duty roster as the girls each see the plan for them tonight. There are a numerous set of duties options, each break down as such.

1: The most desirable and often well known, experienced and ready to please girls will be called up as night time escorts. These are usually done to prominent business men, city leaders, bureaucrats and at times, out of town business men visitors. This is the holy grail for any of the sissy girls as these dates are usually many hours long and often have enjoyable, exciting rendezvous with these men, the girls used here are often the ones on longer hormone use and usually of some form of feminizing surgery and/or general long timers.

2: The most typical night time situation for the sissy girls is general street walking prostitution at numerous tranny strolls around the city.

3: Some girls are offered out as club sluts and party favours to things like male stags and other general male group events, which can be very interesting for lots of gang banging sex.

4: Occasionally some girls are pulled aside for various pornography video productions. Most girls do covet being used in pornography as its a sign of their visual desirability.

Tonight Chantel finds her first night as a Jade Maid Club sissy slut, and she see's it will be a night on one of the tranny strolls as a streetwalker. Maid Penny comes to her aid as Penny as Head Maid has a responsibility to get new girls prepped and ready.

Penny asks, "Hun, you see your duty for tonight?"

Chantel replies, "Yes Miss Penny, I'm on the stroll."

Penny takes hands and places them on Chantel's shoulders, says, "Ahh good, figured Masters would want to get you out on the stroll. OK, come with me."

All girls are to go to their rooms on either the 2nd floor new/sophomore girls floor or the 4th. floor, the floor for the more experienced girls, strip down to their panties and bras. Then all go to either floors communal bathroom, shower and enema stations. Once there Chantel witnesses a room full of sissy girls all bent over hooking up to enema bags having their backsides refreshed and cleaned and now including Chantel's. It's quite a site to see these girls quietly being cleaned out for night time anal sex.

Once fresh, cleaned and flushed out the girls, shower up all together in the communal shower, often washing each other in part for efficiency and yes even some fun and then head back to their rooms to redo makeup and put on slutty clothes for the night. Chantel picks her first nights outfit. It starts with a white satin blouse and a very short black leather mini-skit, both over a black, lace garter belt and black sheer stockings with lace tops. She puts on a black leather cropped jacket and a pair of black leather 5 inch spike heel pumps with ankle straps. She spritzes on some perfume and grabs her black leather over the shoulder purse, filled with I.d., $30 emergency cash, a tube of lube, some cosmetics and perfume. She steps out from her quarters by 7:00pm and she sees Penny waiting for her. Penny has her follow her to the first floor. Penny is in a black lycra dress under a black cotton jacket with black stockings on and spike heel black pumps too.

Chantel finds that she and Penny will be taken by an SUV driven by Master Marty with sissy Traci, who is in all white, white leather mini-dress, white stocking and white pumps as well as sissy Karly who is in a blue and black lycra mini-dress, under a black denim cropped jacket black stockings and 6.5inch blue suede platform pumps.

Marty has each of the girls get inside the SUV and begins to drive them out to a tranny stroll near the airport. Chantel is lost in thought, it's evening and near 7:30pm as she is about to work her first night as a tranny slut.

Penny pats her left thigh as she says, "Don't worry Chantel, it's ok, you will be fine. The airport stroll is a good one for us as it usually has more mature men on it. The tranny stroll near the bar scene is a bit more rougher as it has more younger and often drunker guys. That stroll can be good for a lot of pump and dumps. You get more guys quickly but often they try to cheat you out of money. The airport stroll usually has married, widowed, divorced dudes and often older men. It may some nights be harder to get a lot of men but they usually pay up no problem."

Chantel says, "Thanks for the info Penny, I'm sure I will be ok, it's just my first night.

Biff is the other SUV driver and he takes sissy Candice, sissy Meagan, sissy Traci and sissy Marie out to the bar scene stroll.

Getting to the stroll, Marty has the girls get out, he informs them the quota for them is a minimum of $500.00 each tonight, then drives off. It's cool and clear now, having an early evening rain shower. The girls are near the airport and can hear aircraft landing and taking off. The stroll is about two blocks long and tranny girls from others or those who work on their own also are out. Chantel sees at least eight other girls, that make twelve and a good choice for cruising men. Penny tells Chantel, most places to work here will be in the john's cars, also down the street where closed up commercial buildings are and in back stair cases, behind garbage bins or behind back walls, to get to the action. Chantel attentively takes Penny's info all in. The four Jade Maid Club girls stay in their one general working area, so they chat but keep eyes open for tricks.

Traci looks at Chantel and says, "Hun, pretty exciting first night huh?"

Chantel sheepishly smiles and replies, "You said it Traci, I'd be a liar if I said I was not nervous."

Karly interjects, "Ahh, Chantel, you'll be fine, your very cute and you are new, the men who cruise here are going to want to be with you."

Chantel says, "Yeah I guess so."

Penny says, "We all look out for each other here Chantel, since most of the action is near by it will be pretty safe, but again most men here are not looking for much of an issue with girls like us nor to have any run ins with the cops."

They all chat a bit and cars cruise by. Penny notices one car's driver looking at Chantel and she says to go check him out as he parked about 20 feet away.

Chantel says, "Well here goes."

She walks in her black heels, click, clock, click, clock to the passenger side of the blue Toyota Camry, she leans into the open window and sees a white man, maybe 40, average looks, black hair and beard as he look at her.

Chantel asks, "Hi, hun, nice night."

The driver says, "Yes it is...You look new here?"

Chantel replies, "Yes sir, Darlin, are you looking for some fun?"

The driver smiles and says, "Well yeah, you look great, you have nice legs. How much?"

Chantel smiles and says, "Why thank you for the compliment I love my legs too, I would love to offer you more than just a look at my legs, $40 does it."

The driver pauses and then says, "Ok, um, would you like to get in my car?"

Chantel agrees to getting inside the car and asks, "What are you into hun?"

The driver says, "Um how about a good blow job?"

Chantel, says, "OK, no problem, you wanna do it in your car?"

The driver says, "OK, we can park over there in the empty parking lot." as he hands Chantel $40, which she stuffs in her bra.

They drive to the parking lot and park, he says, "My name is Frank, yours is?"

Chantel replies, "It's Chantel, Darlin."

Frank proceeds to slide his seat back and then undoes his belt and pants pulling them down revealing his briefs. His cock is rock hard inside his briefs. He then pulls out his cock and balls showing to Chantel a good 6 inch cock that is quite thick and uncut. Chantel leans over and her left hand fondles Frank's balls, her bright red painted finger nails contrast with his ball sack. Frank enjoys the feeling of her fondling and squeezing his balls. She takes her right hand and grasps his nicely hard cock, tugging on it and seeing Frank ooze with lust. She now moves her head towards Frank's cock and her red lip coloured lips kiss it and then parts open her mouth as his cock slips over her wet tongue. Chantel wraps her tongue lustfully around his cock as Frank moans. Chantel begins to slurp and suck as she takes the cock in a bobbing motion. Chantel moans along with Frank as they both get into serious cock sucking session.

Chantel works over Frank's cock and senses he is nearing what he wants an orgasm into her mouth. He strokes Chantel's hair with his hands as she bobs and sucks on his stiff cock until he reaches his zenith of lust and his hot cum sprays into the back of Chantel's mouth as she lip locks on his shaft holding his hot cum in her wanting mouth.

Frank pushes out volley after volley of cum until he has no more to give. Chantel pulls off his cock, her red lipstick all over the now softening shaft. As Chantel sits back up, runs her right hand over her hair, Frank tucks his stuff back in his briefs and does his pants up.

Frank says, "That was great Chantel, just fucking great."

Chantel smiles and says, "Thanks Darlin, your cum was delicious too."

Frank drives Chantel back up to the street corner where Karly and Traci are standing as he says he hopes to see Chantel again as they say good night to each other.

Chantel walking back to the corner, Traci asks, "So how did it go?"

Chantel replies, "Great, a nice mature guy just looking for a good blow job.

Time ticks by, Traci and Karly both get dates and Chantel stands alone for a while as another car a Dodge Caravan drives by and stops. She walks up to the passenger side and asks if the driver wants a date? His reply was yes if the price is right. He is a regular Joe a tad overweight maybe 30 years old and brown haired, clean shaven. She sees two car seats in back and thinks he is probably married. She kind of does not want this date but knows he will just get it from another tranny if not her, so she goes on.

They agree at $40 for a fuck and Chantel gets inside the front seat of the van. He gives her his name and it's Tom, she gives him hers. He tells her he loves her name. They drive down a side street by a large commercial building and park near a back covered stair case.

Tom says, "You saw my car seats, yes I'm married and we have two kids, 3 and 5 years old, does it bother you?"

Chantel replies, "It's not my place to judge Tom."

He adds, "My wife is 7 months pregnant with our third and sex has dried up between us for now, I just need to get off and for some reason I feel hooking up with a hot tranny is easier to square in my mind."

Chantel says, "Understood Tom, it's your call, if it makes it better for you lets have some fun."

Tom gives her the $40 and they get out of his Caravan and walk down the flight of stairs under the cover of the building and she grabs some lube from her purse. She has Tom drop his pants and briefs, his nice 7 inch cut white cock is at attention for her as she run lube over his shaft, then she turns around, bends over, pulls up her black leather mini-skirt and then tugs down her panty showing her butt hole. Chantel quickly fingers her hole with some lube and then leans toward the staircase wall with her hands holding her in place, her hot little ass exposed for Tom to see and enjoy.

Tom begins to pull her butt cheeks apart and he then pushes his cock inside her, past her sphincter as he takes her ass for his pleasure. Chantel groans and sighs as she accepts his hard cock and listens to Tom moan and grunt.

His pumping of Chantel's back side grows harder and deeper as if his cock is on a mission to probe every inch of her butt hole. It's quite remarkable with how a hard cock can stuff a willing butt hole. They both begin to work well together. It's quite a feeling for both. Tom is quite horny and gets closer and closer to orgasm as Chantel the good slut that she now is accepts his invasion and soon to be reward of filling her with his hot semen. And then just like that Tom grunts and thrusts as he shoots out a thick, hot volley of his cum into her rectum. They both enjoy the feeling, Tom is totally orgasmic as he fills her as much as his cock will allow. Once spilled of his seed he pulls out, tucks his tool back into his briefs and does his pants up. Chantel quickly takes tissue and wipes her back side, fixes her panty and skirt and they both get back into Tom's Caravan as he drives her back to her street corner. The other girls are all back for now as she steps out and Tom says good night.

The night goes on as expected for all four girls, all busy and by the time Marty is back with the SUV to pick them up it's 12:00 midnight. As the four girls get back in the SUV, they hand Marty their money and he totals it then puts into an envelope. He writes each girls take for the night.

Penny, $580.00, Karly, $500.00, Traci, $540.00, Chantel, $540.00, The total take from the girls street walking work night is $2,160.00, their Masters will be pleased.

They are driven back to their quarters and like all the other sissy girls of The Jade Maid Club it's time to unwind, undress, wash makeup off and get to their rooms for standard night's bed time. Chantel's first day and night in her new life and occupation has just ended, many more years of likely servitude to follow.

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Chapter Five to follow soon.