Title: Postcards from the Estate // Maids' Service / Deidre's First Day
Deidre's First Day
[This postcard is about Deidre, whose wife has signed him up for a weekend of training as a Restoration chambermaid.]
As he checked his e-mail, Colin was surprised to find a message for Deidre, his feminine alter-ego. The only other person who knew of her was his wife. At her insistence, Deidre was kept securely in the closet except for one or two weekends a month, and then they went several hundred miles away to towns in which they were not known for Deidre to strut her stuff. Colin opened the e-mail:
"Dear Deidre:
"I have tried throughout our marriage to indulge your need to be a woman. Since this need has grown stronger each time Deidre is set free, I am willing to continue to indulge you only if I can benefit as well. I have found a special club which offers guidance to men such as you. I have signed you up for a series of weekend sessions. You will find a brochure about this club, The Estate, next to the computer. You have a choice: when I get home, you must be dressed as Deidre and ready to spend this weekend, and every weekend, or more, of our lives as Deidre, or, you can send Deidre away, never to have her as part of our lives again.
"Love, Sandy."
Colin was stunned. He knew his crossdressing was not fully accepted by his wife, but he did not think it was a threat to their marriage. He clicked off the computer and picked up the brochure. His heart began racing. He had never thought such a place existed, or could exist. He and Sandy had played everything by ear, learning as they progressed. There had been several close calls and dicey situations. Here was a place where he not only could be Deidre freely, but they would help him be the woman he wanted to be. Choice she said. Live without Deidre? He now knew that he would be able to live without Cassandra a lot easier than he could live without Deidre. But why not live with both?
Cassandra was not sure who she would see when she entered her home. Never comfortable with her husband's needs to act like a woman, she had gone along as long as the cross-dressing episodes were limited to a couple of weekends a month, and then only in places far away from their home or workplaces. She had come across a wives-of-transvestites chat room on the internet, and met with Sheila, one of the wives who lived in their home town. Sheila had reassured her on many issues, and heightened her anxiety on others. But what most impressed Cassandra was how Sheila had turned her husband Douglas's fetish to her own benefit.
On Cassandra's first visit to Sheila's comfortable, but definitely middle-class, home, she was greeted by a uniformed maid. Throughout that initial talk, the maid was everpresent. Sheila never said anything to the maid, but it took only a look, a raised eyebrow, a flip of the hand or the flick of a finger and coffee was poured, sandwiches were served, dishes were removed. When Cassandra asked where Douglas was, Sheila laughingly pointed to the maid. So completely feminine-looking and natural in his movements was he, that Cassandra thought the maid was a woman.
In subsequent visits, Cassandra was introduced more fully to Douglas' alter ego, Gwendolyn, the Edwardian maid. At a special weekend stay, Sheila introduced Cassandra to two other wives of transvestites, and their husband-maids. The women shared their experiences as wives of cross-dressers with Cassandra, and informed her of the Maids' Service at The Estate as the means they had used to come to grips with their husbands' predilections. The Estate is a private club for persons whose sexual preferences are quite exotic. The Estate offers several services catering to its members' needs for dominance, submission, variety, multiple partners, whatever. Above all else, The Estate offers discretion.
Convinced that such a relationship was the solution to her situation with Colin, Cassandra had Sheila arrange a membership for her and Colin. At the membership interview, The Estate's representative, Madame Smith, was very straightforward. Since Cassandra's membership was sponsored by Mrs. Nungard (Sheila), and co-sponsored by two other members in very good standing, her acceptance to The Estate was a mere formality.
When Cassandra entered the living room, she found Deidre sitting on the loveseat, reading a magazine, the open brochure on the cocktail table in front of her. Deidre was wearing her dark brown wig, her favorite dark blue dress with small white polka dots. Well, not exactly her favorite, but one they had both decided would be best for traveling. Its full skirt was more comfortable on the long drives they took looking for suitable places for Deidre to be seen, and the color scheme did not draw undue attention to her. Underneath Deidre had on her padded bra, this time filled out to C-cups, a move they usually thought too brazen. He had first put on full-cut brief panties and pantyhose, but the anticipation of his new life had caused him to jack-off more than once as he dressed. Now he wore a garter belt and stockings with a thong two sizes too small over them. This should keep his cock under control. If it didn't, he could always pull it down and relieve himself without disturbing any more of his clothing. In fact, the need for such relief was quickly developing. Finishing his wardrobe was a standard pair of three-inch stiletto pumps in Navy blue. Only his make-up, a little on the heavy side, detracted from his appearance as the suburban lady of the house. On the floor next to the loveseat were Deidre's traveling suitcase and overnight case.
It was only on seeing Deidre and not Colin that Cassandra realized that she too wanted Deidre as a part of their lives. She walked over to Deidre and the two pressed cheeks, kissing the air besides each other's face. Sitting on the cocktail table, Cassandra picked up the brochure. "Did you read this? she asked, knowing that he had.
"Yes," Deidre beamed. "Where did you find this place?"
"That's a rather involved story," Cassandra replied. "I'll tell you on the way. But ... are you sure you want to do this?" Deidre could only shake her head enthusiastically. "Then grab your purse. We've got a long drive ahead."
On the way to The Estate Cassandra explained about Sheila and Douglas and The Estate itself. One of the services is a training program for submissives, who can be trained to perform a variety of traditionally female jobs: maid, secretary, receptionist, waitress. The Maids' Service trains submissives in the duties of English maids, French maids, American maids, plantation house servants, medieval wenches, colonial servants, whatever type of female domestic the member desires. The submissive can be either male or female, but all will be trained--and dressed--as maids. Since Colin was not aware of any of the arrangements being made for him, he must be given the opportunity at several points to decline: when first presented with the concept, just before entering The Estate, and immediately after the nature of his training is revealed to him. However, since discipline is part of a maid's training, any resistance or defiance once the training begins will be treated as role-playing on the part of the trainee. Cassandra was careful to let Deidre know that she could back out anytime before the training started, but after that Deidre was committed to the program, at least for that weekend. Deidre was silent after this for a long time. Living as Deidre the woman was one thing. Living as Deidre the maid was something else.
"If I don't like being a maid, can I still be Deidre?"
Cassandra had not thought about this. Since the only other transvestites she had met were the husbands of Sheila and her friends, she had not considered other options. "After this weekend, Deidre can be whatever you want her to be." At this, Deidre relaxed. "And remember," Cassandra continued, "you can say no anytime before we walk onto The Estate." Deidre just smiled. * * *
Just outside The Estate is Estateville. This had originally been the robber baron's company town, turned into a ghost town when the march of time and progress made his business obsolete. The Estate had acquired it, with the estate, and maintained it as a company town. All of the businesses served a dual function: outwardly, they seemed like the standard small town restaurants, motel, and shops of any rural part of any state. But they were staffed by The Estate's employees or trainees or guests. As part of the weekend training session, Cassandra and Deidre were automatically booked into the motel. As they entered their room, nothing indicated that it was any different than the dozens of other motel rooms they had used.
No sooner had Cassandra closed the door than Deidre hiked up her dress and pulled down her panties. Her cock had been straining for freedom for over an hour. With her panties at mid-thigh, she flopped on her back on the bed and begin stroking herself. Cassandra had been sexually aroused since she saw Deidre sitting in the living room. She wasn't going to let that hard cock go to waste. Mimicking her husband, she too hiked up her skirt and straddled him. She was not wearing hosiery, and had only to slip the crotch of her panties to the side as she guided the cock into herself. Grabbing Deidre's wrists, she pinned her to the bed while she rode her cock. Deidre's need was greater than Cassandra's, and she came in less than a minute. She quickly went soft, falling out of her wife's cunt.
Cassandra knew that Deidre would not rise again without extensive foreplay. And foreplay was something Cassandra neither needed to receive nor wanted to give. As she looked down at her husband, a certain anger born of sexual frustration, contempt, and confusion welled up in her. She would make Deidre pay for Colin's inability to satisfy her at this moment. Well, ... not satisfy her with cock. Deidre's tongue never deflated. With Deidre's cock now fully out of her, Cassandra knee-walked until she was straddling Deidre's head, leaving a trail of cum on Deidre's dress. Firmly planting her knees on the bed, Cassandra nearly smothered Deidre as she pressed her crotch into her husband's face, rocking from side to side and forward and back to make sure Deidre's face was covered with the combined discharges of their bodies.
Deidre did not see the anger her cumming had caused, or the hatred now twisting Cassandra's face as her wife wiped the transvestite's face with her pussy. They always included a lesbian sex scene when she was Deidre. In fact, most of their sex, whether he was Deidre or Colin, involved his head plastered to her cunt. To Deidre, this was just another incident of eating his wife to orgasm, or orgasms as the case might be. So as he licked her lips, and probed her slit, and flicked her clit, and nearly drowned in the flood of his semen and her juices, he did not know that the orgasms Cassandra was experiencing were bittersweet to her, for she not only wanted to cum, but to cum with a hard dick probing her pussy, and a hard body riding hers.
But as much as Cassandra wanted a hard cock, an experienced tongue was what she had. It was experienced not only in eating pussy, but in eating her pussy. Soon her rocking back and forth and side to side was not motivated by anger but by lust. While she may have wanted one mind-blowing orgasm, the series of smaller orgasms that racked her body each time Deidre's tongue circled her clit were just as good. She rested her head on the pillow now cradled in her arms, her hips raised, her ass moving in slow circles.
Deidre kept licking, establishing a rhythm between her wife's lips, vagina, and clit, one hand keeping the lips open, the other stroking her own cock. She could easily spend the rest of her life as Deidre if this is what that life would be. Relieved by her orgasms, Cassandra looked at the mirror over the dresser to see that a hard cock was now available. Abruptly standing, she ordered Deidre to undress, doing the same herself. Having less to remove, Cassandra finished first. She pulled back the covers and positioned herself in the center of the bed, legs spread.
"Fuck me," she commanded when Deidre was naked. "Fuck me hard, and fuck me long."
Deidre was now Colin again, only the smeared make-up a reminder of Deidre. He climbed on top of his wife and began performing his husbandly duties. His skin still tingled from the feel of the nylon and satin and lycra he had just removed. That, the anticipation of what the next two days held for him, and having already cum only a half-hour earlier let him meet Cassandra's command. Resting whenever he felt himself ready to cum, he was able to deliver a good twenty minutes of pumping Cassandra's pussy before he again erupted. Cassandra did not orgasm during this fucking, but the nearly constant pistoning in and out of her cunt satisfied most of her craving for cock. But not her need for a hard body. Colin was rather slim, but not muscular. And the smell of make-up, semen and her own juices on his face was a constant reminder of why they were there. But The Estate has many services. Maybe she should indulge herself while indulging her husband.
After they had showered, they ordered dinner sent to their room. Since Colin had brought only Deidre's suitcase, he reverted back to Diedre, choosing an ankle-length nightgown with leg slits. With her painted toes peeking through her high heel mules, and the traces of make-up still defining her face, she still looked more female than male even without the undergarments or the wig. Cassandra wore one of the complimentary spa robes provided by The Estate.
As they ate, Cassandra explained that the training program in which Deidre had been placed, the wife is always referred to as Mrs. X or Y. Cassandra had decided to keep her married name so Deidre would have to refer to her as Mrs. Nevins once the training starts.
"I have been assured that you will be as complete a woman as possible when this weekend is over." Cassandra warned. "If you have any doubts about this, you can still back out." Deidre could only shake her head, already planning her life beyond the weekend. The thought of days in nylon and satin and lace and lycra resulted in her tenting the front of her nightgown, being unrestrained by all that nylon and satin and lace and lycra she was thinking about.
Cassandra moved to the bed, sitting against the headboard, began reading other brochures about The Estate's services she had not shown to Deidre. "I also think you should call me Cassandra from now on," she added. As she spoke, she looked at Deidre, only to notice the way the nightgown was now poking out.
"Deidre, come here," she directed, patting the bed next to her. As Deidre climbed onto the bed, Cassandra untied her robe, letting it fall open. Deidre started to lay next to Cassandra, but was corrected.
"Don't lie down. Sit up against the headboard. Hike up that gown." Deidre complied, gathering the hem of the gown just above her pubic hairline. Her cock was now pointing toward the ceiling. Cassandra straddled her legs again, placed her hands on Deidre's shoulders, and slid down the pole. Leaning forward, she commanded "Suck my tits. Make them tingle 'til they hurt!" Deidre again complied, knowing the combination of soothing tonguework and sharp nips and bites she wanted.
Cassandra did not move, savoring the feel of Deidre's lips, tongue and teeth on her breasts as she squeezed her cunt around her husband's prick. As the sensations at both breast and pussy grew, she moved one hand to the back of Deidre's head and the other to the top of her pussy. Deidre, for her part, placed both of her hands at Cassandra's waist, pulling her wife slightly to her. Cassandra begin fingering her clit, the motion causing her hips to rise and fall reflexively. They stayed like this for several minutes until Cassandra had that mind-blowing orgasm that had eluded her earlier. Satisfied, she pulled herself off her husband's still hard cock.
Deidre thought it was now her turn for satisfaction. She was wrong. Cassandra went to her suitcase and pulled out a longline panty girdle. "Put these on," she said, tossing the girdle to Deidre. Deidre got up and put them on, thinking this was just part of a night of lovemaking for them. Instead, Cassandra removed her robe and climbed into her side of the bed, turning her back to Deidre.
"You better get some sleep," Cassandra said dryly. "We have to get started very early in the morning." With that she turned off the lights from her side of the room.
Cassandra arose at 5:30 a.m. She quickly woke up Deidre. "You must be in the conference room by 6," she informed her. Deidre quickly showered. When she came out, Cassandra had laid out a plain house dress. "Put this on. And make sure you have on your bra and panty girdle. And no lipstick!" When Deidre was suitably attired, Cassandra escorted her to the conference room, halting at the door. "If you really want to do this, you have to walk in there on your own." So saying, Cassandra turned and walked back to their room.
Deidre walked into the room. There was only one other person in the room. Deidre immediately saw it was a man in drag. She hoped she didn't look that obvious. By the clock on the wall, she was ten minutes early. During the next eight minutes three other women entered the room. Deidre immediately recognized one of them as a man in drag also. The other two were more passable as women. In fact, Deidre would have thought of them as a woman but for their circumstances. The one thing she found strange was that none of the other transvestites were wearing lipstick.
When the hands on the clock were perpendicular, a tall woman wearing a lilac long-sleeve blouse, a deep purple vest, matching ankle-length staight skirt, and three-inch black pumps strode into the room and headed for the podium. She surveyed the room with a self-satisfied expression.
"Good morning, ladies," she began. "I'm Mistress Gertrude. I will be in charge of your training for this weekend. You were to be informed of the function and rules of The Estate, and the nature of your training. To make certain we all have the same understanding, let be review the terms and conditions of your stay.
"You have been registered here by a guest of The Estate who we call your sponsor. If that sponsor is a female, you will refer to her as Mrs. whatever she wants to be called. You will address all female guests, or guests in a female role, as Mrs. or ma'am. You will address all male guests as Mr. or sir. You will address all Estate staff such as myself as Mistress, or staff in a male supervisory position as Master. You will not address anyone else, unless given permission. You will response promptly and directly to anything asked of you by guests or supervisors.
"You will spend the next two days being trained as maids, according to the desires of your sponsors. Part of that training may require discipline. Your sponsors are having coffee in the dining room. If you do not wish to participate in the training, you are free to leave. We will arrange transportation back to your home towns, in appropriate male attire."
At this point Mistress Gertrude produced a box which she placed on a table next to the podium, "I will leave the room for five minutes. If you wish to continue training, you will be wearing the lipstick which is inside this case when I return." Mistress Gertrude then strode out of the conference room as imperiously as she had strode in.
No sooner had she exited than the transvestite who was in the room first bolted for the box. Inside were five compacts and lipsticks. She grabbed one and began smearing her lips, not very well. The other four looked at her, then at each other. After the hands on the clock moved a tick or two, they too approached the box and removed a compact and lipstick. With varying degrees of skill and feminine demeanor they applied the lipstick. Deidre did not like the shade, a cherry red.
Exactly five minutes after she walked out, Mistress Gertrude walked back in, assuming her post at the podium. She smiled to herself as she surveyed the room. "Ladies, follow me." She led the quintet outside to one of The Estate's motor surreys. The trainees sat in silence during the brief drive to the Maids' Quarters.
It was only 6:20 a.m. when they arrived at the Maids' Quarters. This was a three-story stone building which had been the single mill girls' dormitory when the town's mill was in operation. The top floor was an open dorm which accommodated thirty maids. Each maid had a space wide enought for her single bed and a bedside armoire, not much larger than a military locker. At the foot of each bed was a hope chest. For every five spaces there was a vanity. At the entrance to the dorm were coatracks on either side of the door for overcoats, umbrellas, boots and other outerwear for inclement weather. Training occurred year-around. At the far side of the dorm was the showers and toilets. Each space had its own dorm window, with valanced curtains. All the beds had identical bedclothes, and were immaculate.
Mistress Gertrude ushered the trainees to the dorm, walking them up the three flights of stairs. All of the future maids were wearing standard 3-inch pumps. They were herded to a center set of beds along one side of the dorm. Mistress Gertrude assigned each one to a bed and instructed them to undress. They first undressed only to their lingerie, only the first maid undressing fully. All were wearing bras and a variety of panties, pantyhose, garter belts, and stockings.
"Undress means undress." Mistress Gertrude sternly admonished them. They then proceeded to undress completely. For three of them, the entire episode was sexually stimulating and their cocks were in various stages of arousal, one at full mast. They were also at various stages of hairyness.
Mistress Gertrude ordered them to open their hope chests. "In the top tray you will find your toiletries. Among these are depilatories. You will all now shower and remove any body hair other than a pubic patch no higher than one inch above your member, and the hair on your head. And for those of you with a clitoral problem, you will relieve that problem before returning. You will be back here in ten minutes. You may assist each other, and speak to each other while showering."
Deidre did not need to remove any body hair, but entered the shower anyway. Mistress Gertrude's tone indicated that everyone was to enter the shower, regardless of need. The person who was first to apply the lipstick also was the hairiest. She was also the most inept. After using all of her depilatory cream and removing only some of the hair, she looked at the others in panic. The most feminine looking trainee came to her rescue.
"Hi, I'm Tami. Let me help you." The depilatories also included safety razors. Tami quickly and expertly shaved most of the hair from his chest, his back and under his arms. His legs were relatively clean. When Tami came to his crotch, she was faced with the clitoral problem, since the first was also the most rampant. "What do they call you," she asked.
"Sherman ... uh, Sherrie," the first maid replied in a voice that an opera villain would envy.
"Sherrie, let's get rid of this 'clitoral problem,' Tami cooed, moving to Sherrie's back. Reaching around Sherrie, Tami grabbed his cock in one hand and his balls in the other. Pulling Sherrie into herself, she quickly fisted his cock, causing him to spurt against the walls of the shower. As Deidre looked between them, she saw drops of something thick and white drip from where Tami's crotch met Sherrie's ass. The other two maids with 'clitoral problems' were jacking themselves also. The shower spray washed their releases down the drain with their hair.
"Ladies!" Mistress Gertrude's shrill voice alerted them that time was of the essence. They quickly towelled off and came back inside the dorm. While Mistress Gertrude was not fully satisfied with the depilation, it would do for the first weekend's training.
She went to Sherrie's hope chest and removed a leather device. Holding it up for all to see, she informed them "Each of you have a cock harness. Take it and gather around me and ..." she looked askance at Sherrie.
"Her name is Sherrie," Tami piped.
Mistress Gertrude looked daggers at Tami. "I will demonstrate the proper application of the cock harness with Sherrie." Mistress Gertrude roughly grabbed Sherrie's cock and placed the leather harness over it. The other four put on their harnesses.
Satisfied, she continued her instruction. "You will remove the top tray and place it on the foot of your beds." After the trainees complied, she continued. "All maids wear the same standard undergarments. The next item you will put on is your girdles, which are on top at the right side of the hope chest."
The girdle was a special design, or rather one of several foundation garments designed for The Estate. This particular design was a high-waisted, long-leg pantigirdle with corset lacing down the front center from waistband to the middle of the crotch. The lacing was so designed that the cock harness was laced into the corseting and pulled snugly into the crotch. Once fastened, the girdle would contain the most rampant erection, presenting a ladylike appearance at all times. There were two garters attached to each leg.
The lacing begins at the waistband and proceeds to the crotch, requiring the novice to be assisted. Mistress Gertrude again chose Sherrie as her model to demonstrate how the lacing was done. This required Sherrie to end up on her back with her legs raised and spread as Mistress Gertrude tightened the lacing a little more snugly than was required. Her handling of Sherrie's cock cause another erection, despite the recent shower activity. This only demonstrated the effectiveness of the girdle, as Sherrie's profile was perfectly flat.
Mistress Gertrude then watched as the other maids helped each other. Deidre helped Carmen, who easily held her legs spread in the air whild Deidre worked at her crotch. Deidre had more difficulty with the position, but Carmen had her rest her legs on Carmen's shoulders until the lacing was finished. Mistress Gertrude took note of Carmen's familiarity with both the positions as top and as bottom. Frenchi also were quiet adept at the bottom positon. Tami seemed more interested in being a top. Afterward, Mistress Gertrude checked the lacing of each of maids, making sure they were snug.
"The next item is your Estate brassiere. You may need the assistance of one of your sisters." The Estate brassiere was a longline bra fitted with breast forms to give the wearer a c-cup. Again, Sherrie had difficulty with hers, to which Tami gladly assisted her.
"The next item are your stockings," Mistress Gerturde next instructed. "They are seamed, and you are expected to keep your seams straight at all times." Each maid was already skilled in putting on the stockings and fastening to the garters.
"You will now replace your tray in your hope chest but leave the chest open," Mistress Gertrude continued. "In the armoire at the head of your bed you will find the uniform you will be wearing this weekend. Put it on."
Sherrie was to be an Edwardian ladies' maid. Sherrie was relieved that she would not have to wear anything revealing. However, she was discomfitted by the fact that she, as well as all the other trainees, were required to wear three-inch pumps all day. Tami was to be a scullery maid. Tami was not pleased with this, since the uniform consited of a very plain ankle-length long-sleeve button-front dress with white collar, white cuffs and white apron. She would have preferred being a French maid. But her sponsor had other plans for her. The Carmen was wearing a ragged peasant skirt and scoop-neck cotton peasant blouse.
Deidre's Restoration chambermaid uniform was more involved. There was a multi-layer petticoat, a white cupless corset bordered in black, and a white short-sleeve shirtdress with full skirt ending at mid-calf. She started to put on the corset, but Mistress Gertrude corrected her.
"The corset is an outer garment." Mistress Gertrude informed her, helping the French maid into her dress, which barely covered the legs of the girdle.
When Deidre put on the petticoat and the dress, the petticoat caused the skirt to balloon and bounce when she moved. Mistress Gertrude came over and fitted the corset on her. The corset came just under her bra cups, pushing them up as much as the longline bra would move. The corset laced both front and back with black laces, finished in a bow at the bottom in back and at the top in front. While not restrictive, it was constrictive. With the other garments she was wearing, Deidre had something confining her from shoulders to sole. And to complete that confinement were the three-inch Estate pumps.
When she finished lacing Deidre into the corset, Mistress Gertrude was quite pleased with her charges. The only thing that remained were the wigs. The Edwardian maid had black straight wigs with bangs, the hair extending to mid-neck. She had a short cap, like a nurse. The French maid was a redhead with shoulder-length curls, topped by a lace cap that was more handkerchief than hat. The peasant maid had the same hairstyle, but in jet black and no cap. Tami's wig was straight mousy-brown hair, shoulder length. Deidre was the only blonde, with straight shoulder-length hair, and a white cap that fully covered the top of her hair. Like the corset, there was a black elastic band threaded through the hem of the cap.
Mistress Gertrude was quite pleased with her charges. Even without make-up, Tami, Deidre and Frenchie were quite passable as women. Make-up would turn the peasant into Carmen. Only Sherrie would be a drag. It was now 7:00 a.m.
"Ladies," Mistress Gertrude intoned, "close your closets. You have a make-up kit in the top tray. Remove it and close your hope chests." When all had complied, Mistress Gertrude headed for the door, instructing "Take your kits with you and follow me."
She led them downstairs to the dining area. Three maids, all of them French, were clearing the tables and cleaning the area. "This is Brigit, Bambi, and Kim," Mistress Gertrude informed her trainees. The three maids curtseyed as they were introduced, then resumed their duties. "Breakfast is from 6:00 a.m. to 6:30 a. m. Being novices, you will be permitted to eat from 7:00 to 7:30. You may talk during breakfast. If you do not finish eating by 7:30 today, or by 6:30 tomorrow, you will be disciplined. If you refuse to eat, you will be disciplined. A faint maid is not of good service. You will not be permitted back in the dorm until your daily duties are finished."
Mistress Gertrude then ushered the trainees into the kitchen, where they were served cafeteria style. Since Brigit, Bambi and Kate had cleaned the dining area, the trainees were limited to one of the tables. The tables each sat six, intended to be five trainees and a mistress. The meal was quite heavy: eggs, sausage, ham, bacon, hash browns, biscuits, toast, jelly, syrup, coffee, orange juice, grapefruit juice, pineapple juice. The Estate was well aware that for all the language, the attire and the training, it was dealing with men who may not have eaten in more than twelve hours. Again, given the constrictive clothing they were wearing, they would soon experience the folly of indulging their appetites.
The trainees were reticent about discussing what situations brought them there. Everyone knew Sherrie and Tami by name. The rest introduced themselves. In addition to Deidre, the French maid was Nora and the peasant wanted to be called Carmen. She was the only one who had chosen what type of servant she could be. Tami was the only one whose sponsor was male. At 7:30, Mistress Gertrude re-appeared.
"Your first chore will be to clean up after yourselves. Carmen and Sherrie will clear the tables, Tami will report to the cook ..." At this Tami let out a shriek, then quickly covered her mouth. Mistress Gertrude gave her a disapproving look. "Deidre and Nora will come with me. And don't forget your make-up kits."
Deidre and Nora followed Mistress Gertrude to the surrey. As they rode back to the motel, Mistress Gertrude explained, "As maids, you must always present the guests, staff and your sisters in service with the proper feminine experience. Therefore you will always be perfectly made up when you are working, and will have your make-up kits with you at all times. This does not mean that you can or will spend your day primping. The colors you wear will be The Estate's colors. That means your nails, including toes, and your lips will always be cherry read. You will always wear face powder. Other make-up will be required when we are certain you know how to apply and wear it. You will now powder your faces and re-apply your lipstick."
This the two maids did, presenting the proper appearance when they arrived at the motel. Mistress Gertrude noted that she would not have to train either Deidre or Nora in the application of make-up. They were taken to the floor which held their rooms and began cleaning, under Mistress Gertrude's supervision. They were thoroughly instructed in the making of beds, with proper corners, the emptying of ashtrays and trash cans, the cleaning of toilets and showers, the vacuuming of rugs were shown to them. With every movement Deidre could feel the embrace of the cock harness, the bra, the corset, the panty, the pantyhose.
By the time they reached the room she had shared with Mrs. Nevins the previous night, she saw the telltale signs of their lovemaking, and recognized those signs in the rooms she had cleaned. She blushed with embarrassment when Nora commented on all the cum stains on the sheets as Nora changed the bed linen. When they had finished their floor, they were returned to the Maids' Quarters. Tami, Sherrie and Carmen were on the second floor, which contains the maids' lounge area, as well as training rooms such as a bedroom, an office, a living room, and a family room.
Tami was in a foul mood since she had had to put her hands in dishwater for the first time in years. Sherrie kept fidgeting, not comfortable with her foundation garments. Only Carmen was happy, her lips flaming red, her mascara and eye shadow and false eyelashes completing her sultry Latina peasant look. She had evidently satisfied Mistress Gertrude that she both knew how to apply and how to wear make-up.
Shortly after they got back, Sherrie had a near crisis as she had to anwser nature's call and could not manage all the lacing. This gave Mistress Gertrude the opportunity to explain that we would have to piss sitting down. We could peel the panties down and up to take care of our other business, but it was impractical to undue the lacing, piss, and redo them. Deidre didn't know what Sherrie found more embarrassing: having to sit to piss, with her pantyhose down and her dress up, or having the other maids watch her do it. There were no stalls in the loo. Mistress Gertrude insisted that since the maids were all there, that all relieve ourselves, as this would eliminate the need to do so later.
The maids had lunch with the other maids, where they learned that there were twenty-two of them there for the weekend. The other seventeen were in various stages of training, from a week to a month. Five of them were biological women, and three were transexuals. Their Estate panties were different, but all of their other garments were the same, and they shared the dorm with the trannies. Most of the maids had similar names, ending in either i, ie, or y: Shari, Sherrie, Sherry. The largest number were dressed as French maids. Four of the maids were self-sponsored guests.
After lunch, the Deidre and Nora were paired with someone else, Deidre with Carmem. The afternoon was spent cleaning the rooms of the escorts. Unlike the maids, the escorts have their own rooms. Most of the escorts had pictures of themselves in Estate uniforms and civilian clothing all around their room. Despite the ban on talking, Tami kept up a running dialogue whenever Mistress Gertrude was away, commenting on the sexual equipment or looks of the various escorts. One exceptionally handsome escort was named William. He had a picture of himself nude and fully erect. When Carmen saw that, she commented that he would tax both ends of her body. Deidre tried to ignore her, but thought that a woman wouldn't be able to walk right for a month after a night with this man.
At the end of the afternoon Deidre and Carmen returned to the Maids' Quarters. Most of the other maids were in the downstairs living area, watching television. The only time they were allowed in this area is the hour between the ending of their work day and dinner, and the time from the ending of dinner to bedtime.
Dinner was served precisely at 6:00 p. m. Since all of the maids were eating at the same time, the dinner period was a full hour. As 7:00 p.m. approached, the maids begin drifting into the living area. The three maids who would have to clean the dining area knew who they were, and remained. The weekend trainees ate together, and watched the others, taking their cues from their actions. As everyone drifted toward the living room, they too rose to go there.
"Deidre," Mistress Getrude's voice was less sharp than normal. "You will remain." Surprise shown in Diedre's eyes. She knew that being ordered to remain behind was not good. As the other maids went to the living room or returned to the dormitory for the night, Deidre was escorted to the basement.
The basement was equipped with several rooms. The room Mistress Gertrude entered was barely furnished, with just a full-size bed, an armoire, a nightstand, a hope chest/bench at the foot of the bed, and several stuffed chairs. Mistress Gertrude pushed her into the room, closing the door behind them. To her great shock was that Mrs. Nevins was there, sitting in one of the chairs. Why was her sponsor still at The Estate?
As she got over her initial shock, Deidre noticed a man standing at the head of the bed, dressed in the uniform of an escort. She had not yet become aware of the various color schemes denoting the various functions or duties of the staff. If so, she would have noticed the black-and-lavender tie. Getrude guided Diedre to the escort, turning her to face Mrs. Nevins.
"Does madame have any special instructions?" Getrude asked Mrs. Nevins.
Mrs. Nevins looked at the trio, studying them for several minutes. Shifting her position slightly, she looked at Diedre. "Diedre." The maid looked at her mistress, the fear very evident on her face. "I have overseen every aspect of your transformation into womanhood. This gentleman," she nodded toward the escort, "will take you another step. I understand that Mistress Gertrude will provide you with the proper instruction. Be brave, all true women must experience this at some time." Mrs. Nevins then sat back, signalling with a nod that the event should continue. What Deidre did not know was that there was also a video taping system which would record everything that happened in the room.
Gertrude turned to the trainee and the staff member. "Deidre, this is William. William, this is Deidre. Remove your clothing." William immediately began unfastening his clothes, methodically placing them on one of the chairs. Deidre, in shock now that she realized she was about to be deflowered, froze. The picture of William and his immense instrument flashed into her mind.
"Deidre, did you not hear me?" Gertrude asked, harsly. Not waiting for an answer, she grabbed the maid, turned her toward William, and began unfastening her corset. Finished, she ordered, "Now take off the rest of your clothing." Deidre removed her dress and petticoat, took off her shoes and unsnapped her garters. She was standing directly across from Nrs. Nevins when she unfastened the girdle.
"Wait!" The voice was Mrs. Nevins'. She was not aware of the completeness of the maid's uniform when she signed Diedre into the maids' service. The girdle and cock harness arrangement intrigued her. This was a new vision to Mrs. Nevins, and she wanted a few moments to savor it. Mrs. Nevins marvelled at the contraption which so completely imprisoned Deidre's cock. She would have this item before they left The Estate. Satisfied, she signalled that the undressing should continue.
William had finished undressing, since he had only to drop his pants, and stood at the head of the bed, his cock rampant. It was a most magnificent cock. Escorts in the black-and-lavender class have one function at The Estate: fucking male transvestites. It does not matter whether the transvestite comes to The Estate as a guest or is sent or brought for training as Diedre was; if she is to be fucked as part of her stay, a black-and-lavender will do it.
And for this duty, there are two types: slightly large cocks and huge cocks. Since most trainees are also anal virgins, the slightly large cocks are recommended, giving the she-male the feeling of fullness a first fuck should convey, but not being so painful as to be traumatic. The large cocks are recommended for she-males accustomed to anal sex. But these are only recommendations. The sponsor decides. Sheila had recomended William, who had deflowered Gwendolyn. William was over 9 1/2 inches fully erect, and nearly two inches in width. Naked, he stood at attention, both body and cock, awaiting further instructions.
Looking at him, Mrs. Nevins had a fleeting-very fleeting-feeling that maybe she had been too ambitious in her request. This was a cock bigger than any she had ever had--and one she wouldn't mind having. Deidre's response was not that fleeting. Facing William as Gertrude undid the lacings of her corset, she had a full view of his instrument. Anticipating its invasion of her, she began whimpering, tears making the mascara streak her face. Surely Cassandra did not intend his being a woman to go this far. They didn't even engage in anal penetration in their private lives.
"Stop crying," Mistress Gertrude admonished her. "You're not a woman until you lose your virginity. Now remove the rest of your clothing." Deidre removed the rest of her clothing, folding them and placing them on one of the chairs. She looked at Mrs. Nevins as she did so, her eyes imploring her mistress to spare her. Mrs. Nevins did not.
Mistress Gertrude guided Deidre to the nightstand. Opening the drawer, she took out two condoms, and a large tube of lubricant. Handing the condom to Deidre, she stated "Place this on William." One of the rules of The Estate, for guests and staff alike, is no unprotected sex. Deidre's hands were shaking so badly she had difficulty getting the rubber on William's cock, practically jacking him off in the process. When she had completed her task, Mistress Gertrude handed her the lubricant. "I suggest you make sure he is good and slick," she sneered. Again, Deidre mearly jacked him off greasing him up.
When Mistress Gertrude had determined that William was ready, she ordered Deidre onto the bed on her hands and knees, positioned so that Mrs. Nevins would be able to witness the penetration. "Grease her up," Mistress Gertrude instructed William. He took the lubricant Deidre had used on him and squirted a copious amount on his fingers. Deidre had never stopped whimpering or crying, and the insertion of William's finger in her asshole changed the whimper into a moan. William kept working her asshole until he had three fingers inside her. After several minutes, he looked at Mistress Gertrude for the go-ahead. The moment of truth had arrived.
Mistress Gertrude looked at Mrs. Nevins, who nodded assent. Mistress Gertrude nodded to William. He placed the head of his cock at Deidre's asshole, grabbed her hips firmly, and with a steady push invaded her. The moan turned into a wail so plaintive that even Gertrude winced. Mrs. Nevins winced not. William did not end his push until his pubic hairs were firmly caressing Deidre's ass, his balls kissing hers. Pausing only long enough for Deidre's anal sphincter to make some adjustment to his size, William pulled back until just the head was inside the opening. Deidre's wail at the withdrawal can only be described as blood-chilling.
William pushed forward again until ass met hair, then withdrew. Gripping Deidre's hips as firmly as he could, he began sawing into the maid. Deidre's wails were now sirenlike and continuous, acccompanied by a steady stream of tears. Unmoved and transfixed, Mrs. Nevins watched William's cock disappear into and reappear from Deidre's ass. The only thing that surprised her was William's stamina. The fucking lasted a full half-hour with no break in William's stroking. After the first ten minutes, Deidre had collapsed on her arms, her face buried in the bedcovers. Only William's grip on her hips kept her on her knees. For the next fifteen minutes he sawed in and out of her in a steady rhythm. During the last five or so minutes William picked up speed enough to come, burying his cock in her and holding her ass to his groin.
It took several minutes for William to become soft enough to easily disengage from Deidre. She looked a sight: ass in the air, head and shoulders on the bed, face smeared with make-up and tears, whimpering. William stood at the bedside, his rubber-clothed cock hard but not fully erect. Opening the lower portion of the nightstand, Mistress Gertrude removed a filled wash basin and two wash cloths. She gently wiped Deidre's asshole. Deidre winced at the touch, her whimpering occasionally turning into moans. The trio gave her some time to recover. When it seemed that she would not, Mistress Gertrude took charge.
"Deidre!" Mistress Gertrude said sharply, "you are not through servicing William." The statement shocked Deidre. What other horror was she to endure? "Stop your whimpering and stand up!" Scared not to obey, the maid struggled to her feet, facing Mistress Gertrude. Mistress Gertrude looked at William's still cloaked member. "You produced that result, please clean it up."
Deidre looked at Willian's cock in confusion, not certain what she was expected to do. Mistress Gertrude grabbed her hand and placed it in the wash basin. Now apprised her her next duty, Deidre soaked the remaining wash cloth, then started to remove the condom.
"Ah, um," Mrs. Nevins interrupted. All three turned to her. "I think Deidre should have a momento of this occasion." Mrs. Nevins said, indicating the condom. "Its ... contents ... should be retained ..."
Mistress Gertrude and William immediately understood, although Deidre did not. Mistress Getrude quickly informed her, "You are to remove the condom so as to retain the fluid within it, Deidre."
This presented a problem, since William was far from flaccid, though not fully rampant. He further refused to co-operate by becoming more erect. Deidre had to work the condom off of him, which caused him to spurt a large load into the condom as she was trying to get the opening over the prodigious head. When she finally had it off, fully the bottom third was filled. Mistress Gertrude quickly took it from her and fastened the opening with a clip that was part of the paraphenalia in the nightstand.
Deidre then wiped William's cock clean. As she held his member in her hands, she marveled that all of that monstrous organ had been inside her, especially when she cleaned the head. But the pain in her ass and the awkwardness with which she now stood were ample evidence. There would be more when she walked up to her room.
When William was clean, Mistress Gertrude turned to Mrs. Nevins. "Would madam like the maid to orally service William?"
The blood drained from Deidre's face. Was there no end to her humiliation? Was she to take into her mouth the very organ that had just ravished her ass?
"No," Mrs. Nevins said, somewhat hesitantly. "I think she's been introduced to enough womanly duties for one night. But ... soon, maybe." With that, Mrs. Nevins stood, walked over to Deidre, and kissed her fully on the mouth. "I'll pick you up tommorrow," she said, breaking the kiss. "Now you are truly a woman." Looking at William's now fully rampant member, she said, half to herself, "Yes, more of a woman than I am." Turning to Gertrude "Please have the tape ready for us tomorrow. And ... Deidre's souvenir."
"Yes, Mrs. Nevins," Gertrude replied, and turning to William, "get dressed."
As Mistress Gertrude escorted Mrs. Nevins to the front entrance, Mrs. Nevins waited until they were beyond earshot of the downstairs room. "I understand you can have a dildo made of your escorts?" Gertrude nodded with a smile. "I would like to examine William more closely for that ... privately. Would that be possible?"
"You can examine him here," the look of disappointment in Mrs. Nevins face was unmistakable, "or at your motel room, if that is more convenient."
"Ah, yes ... my motel room. That would be most convenient. And ... uh, ... when will he be prepared to be examined?" The question was lost on Gertrude. "Well ... he has already performed so ... admirably. Will he be up for ... examination?"
"Let me assure you, Mrs. Nevins," Gertrude cackled, "William is always 'up' for examination."
"Even without a ... someone like Deidre?'
"William is unique among men, in many ways." Gertrude snickered. Mrs. Nevins could not help but notice how much mirth Gertrude derived from discussing William's abilities. "William's only sexual preference is that he prefers sex. anytime ... anywhere ... anyway ... anyone."
"Then I can expect him tonight?"
"Within the hour if that is madame's pleasure."
"Yes ... that is exactly madame's pleasure." So saying, Mrs. Nevins left the maids' quarters.
Mistress Gertrude waited until Mrs. Nevins had entered the surrey, and the surrey was on its way back to the hotel before returning to the basement. Deidre was laying on the bed on her side, her back to William when Mistress Gertrude walked in.. William had taken the seat Mrs. Nevins had, giving him a perfect view of his cockwork. Staring at him was a very much enlarged asshole, one of dozens he had deflowered. This sissy maid would never be the same, he thought, and he was the man who had made the maid a woman.
Turning to William, Gertrude informed him, "Your services are needed at the hotel. Within the hour." William did not have to be ordered twice. This was not the first time a sponsor wanted to savor what she had just witnessed. He quickly left.
Mistress Gertrude went over to Deidre and pushed her fully onto her back. Pushing the maid's knees toward her chest, Mistress Gertrude had full access to Deidre's crotch. She had been somewhat apprehensive at having William fuck Deidre. But now that the deed was done, she knew that Deidre needed a salve to both ease the pain and cause the asshole to close somewhat. Fortunately The Estate had its own medicinal cream for that. The nightstand drawer was stocked with such an item. Gertrude retrieved the jar of cream and crawled onto the bed.
Keeping the maid on her back, Gertrude dipped two fingers into the jar and spread the cream into and around the maid's anal opening. The cream had an immediately cooling and soothing effect, causing Deidre to sigh in relief. Getrude stood up and quickly removed her skirt. Quite experienced, she had her girdle unfastened and heer cock harness removed in less than a minute. Deidre was still laying on her back, her eyes closed as she enjoyed the relief the cream gave. Gertrude quickly jacked herself to an erection and placed a condom over her dick. She then lubricated herself with the cream. Climbing back onto the bed, she crawled on top of Deidre. Before the maid knew what was happening, Gertrude had entered her and was laying on top of her.
Startled, Deidre tried to sit up, but was pinned by Gertrude. As she realized what was happening, she was confused by the sensations of both pleasure and pain in her ass with the image of the woman on top of her. She had not considered that Mistress Gertrude was also a she-male. As Gertrude pumped into her, the cream had a soothing effect on the still raw tissues which Gertrude's dick was rubbing. After William, she barely felt Gertrude. But the salve was working, and her asshole closed enough for Gertrude to come.
After coming, Gertrude laid on top of Deidre and whispered, "It can be really good, if done right." She then kissed Deidre lightly on the lips, Deidre's first kiss from a man. Again, Deidre's mind and feelings were concentrated on her asshole and the kiss didn't register with her. Gertrude pulled out and retrieved a tampon from the nightstand. Liberally coating it with the salve, she stuck in deep into Deidre's ass.
"Get dressed." Mistress Gertrude ordered, doing the same herself. Deidre complied, or at least tried to. The Estate girdle now presented a problem as Deidre found it still painful to sit or to stand. Mistress Gertrude came to her assistance, lacing the front loosely, then returning to dressing herself. By the time Deidre was ready to put on the corset, Mistress Gertrude was dressed and ready to help her. Finished, Mistress Gertrude washed the tear-stained make-up from Deidre's face, the only real tenderness she had shown the deflowered maid. She guided Deidre to the doorway, and up the stairs to the dormitory, informing her, "You better get some sleep. Tomorrow is another day."
-000- Postcards from The Estate//Maids' Service/Deidre's First Day 1