Postcards from THE ESTATE Guy and Ellen
Part V
Getting ready for the evening was a truncated version of getting ready that morning. Almost. First came an enema, administered by Adriane and Chantrelle. Nathaniel had never had an enema, even though he had heard of them. Like he'd heard of periods, though he never had one of those either.
"You're going to be fucked, Ms. Sharpe," Brenda reminded her. "Do you want to reconsider?"
The nozzle in her ass, the rush of water into her bowels, the feeling of pressure, all were not unpleasant. "No."
A second bath, a second depilation, mainly her face, neck, arms, legs and pubic area. With the prosthetic breasts there were no need to do her chest or abdomen. She was surprised that they stayed on during the bath.
"The adhesive is particularly strong," Elaine explained. "It will wear off very suddenly on Monday, and the breasts will nearly fall off. Sort of like Cinderella at midnight."
Elaine, Brenda, Adriane and Chantrelle all tittered at this. Next came the tampon. Ellen felt self-conscious as the four of them watched as she coated it with cream and then placed it in her ass, then wiped the excess cream away. A second pair of special panties--she was to learn later they were called gaffs--was handed to her. This time she placed herself in the pouch and adjusted the panty to give her that feminine look. Waist cincher garter belt, stockings. Then the dress.
Elaine had selected what every woman wears on that first special date: a little black dress. This one was a halter-style with a low back, coming only to her waist, and a plunging V neckline. No wearing a bra with this thing. Ellen now realized that the breasts were so that she could wear this dress. This time Brenda did her make-up, really just a touch-up of what was done earlier. Black ankle-strap sandals with 3-1/2" heels, a double-strand black pearl necklace with matching earrings and a wide black pearl bracelet completed the look. Almost. Elaine produced a new wig the same color Ellen had been wearing all day, but longer. She styled it with a French roll and bangs.
Brenda handed her a black clutch purse. "Open it." Ellen did. Inside was a compact, lipstick, ... and a package of condoms. Ellen looked at Brenda in shock.
"Another rule. No unprotected sex. Mr. Hughes knows the rules, so he should be prepared. Just in case." Brenda stared at Ellen. "Are you sure you want to go through with this?"
Ellen nodded. Brenda then took both Ellen's hands in hers.
"You will end the evening at your suite. If you are to go through with this, you'll have to invite him in. He cannot enter except by your express invitation. Let Mr. Hughes take the lead. This isn't about male ego. He knows what he's doing, and he's good at it. Remember, as a woman you are a virgin. There are things you need to know and do when making love as a woman, but I cannot explain them to you now. Only after you have become a woman will what I have to tell you make any sense. All I can say is that being made love to as a woman is different than anything you imagined. When we meet afterwards, I will explain these things to you. Are you certain you want to do this?"
A thousand reasons not to do this occurred to Ellen. "Yes."
"Then let's go meet Mr. Hughes."
Elaine led the way, followed by Ellen, Brenda bringing up the rear. Adriane and Chantrelle watched, the scene reminding both of them of someone being delivered to the guillotine. When they entered the elevator, Ellen was surprised when Elaine pressed 4. She didn't know where she was to meet Guy, but not in Mrs. Bowen's office. Although it was nearly six, the same receptionist was still on duty. With the same expression and same direction: "Mrs. Bowen is expecting you. Go right in."
The trio entered a darkened office, facing the tall back of Mrs. Bowen's chair. The late summer sun was setting, firing the sky with brilliant reds, and Mrs. Bowen was enjoying the celestial light show. As the sun sank lower and the sky darkened, she turned in her chair to face them. Slowly the room filled with light. She studied Ellen for a long time, taking in her face, dress, stance. "Turn around, my dear," she finally said.
Ellen turned a little too quickly, causing the skirt of her dress to flare. Mrs. Bowen looked to the far wall of her office where there was a sofa, loveseat, two wing chairs, a low coffee table, two end tables, and lamps lighting the area. Ellen had not even looked at that part of the office earlier. A tea set on a tray rested on the coffee table.
"Bring the tea set to me, please, Ms. Sharpe."
Ellen walked to the table, knelt in a near curtsy, picked up the tray and carried it to Mrs. Bowen, coming to Mrs. Bowen's side of the table and placing it gently on the table. She started to return to Brenda and Elaine.
"Stay, my dear," Mrs. Bowen said. Ellen stopped and turned to face her. Mrs. Bowen stood. Ellen was surprised to find that she was no taller than the back of her chair. Mrs. Bowen looked at her, then walked around her, then back again and resumed her seat. She turned to Elaine and Brenda. "You've done very well. Both of you. I really must commend you on the improvement over what I saw this morning. And on her deportment."
The fetching of the tray was a test, Ellen now realized. The expression on the faces of the two staffers was of relief, not joy at being complimented by their boss.
"We cannot take credit for Ms. Sharpe's deportment, Mrs. Bowen," Elaine confessed. "That she brought with her. We only let her enhance it."
Mrs. Bowen raised an eyebrow. Her left one. Right eyebrow: surprise. Left eyebrow: skepticism, even incredulity. "Ms. Sharpe was in here this morning, Ms. Neville. And not this Ms. Sharpe. If my compliments are wasted on you, Ms. Neville, I will refrain from giving them in the future."
"They are not wasted, Mrs. Bowen," Brenda said unctiously. "We just didn't want to claim all the credit when Ms. Sharpe has been such a wonderful and cooperative guest."
Mrs. Bowen looked at Brenda. Ass kissing faggot. Makes a better looking woman than any of my daughters, granddaughters or great-granddaughters. I'd really like to fire her, she thought. Too damn bad she is the best counselor and administrator in Transformation Service. If he was a real woman he'd have Elaine's job.
"Credit where credit is due, Ms. Duncan. All three of you have done very well." Mrs. Bowen turned to Ellen. "And are you willing to be Mr. Hughes dinner companion tonight, Ms. Sharpe?"
Ellen hoped this would be the last time she would be asked this question.
"Yes, Mrs. Bowen."
Mrs. Bowen turned her chair to the wall opposite the one with the furnishings. In a corner was a chair identical to Mrs. Bowen's, facing the windows. Slowly it turned to reveal a full bearded man in a dark, well-tailored business suit. Guy Hughes in the flesh!
Guy strode purposefully to Ellen, who steadied herself by gripping the back of Mrs. Bowen's chair. With each step Guy took in Ellen and assessed what he was seeing. When he reached her he took her in his arms and kissed her deeply. Ellen now knew what Brenda meant. How do you respond to being kissed by a man until you've been kissed by a man? Ellen responded by putting her arms around Guy's neck and letting her tongue play with his. Let him take the lead, Brenda said. So Ellen remembered every girl Nathaniel had ever kissed, and tried to imitate everything that was pleasant in their kisses.
Elaine and Brenda were so intent on watching Guy and Ellen they did not notice the revulsion that quickly washed over Mrs. Bowen's face. Every time she witnessed Guy taking a sissy in his arms she thought of the times her granddaughter was in his arms, her lips kissing Guy's. Mrs. Bowen wondered on these occasions what Margaret Hughes Sheffield had done to turn her nephew gay. Her granddaughter, Shirley, had informed her that Guy was quite the stud in bed. Shirley was not averse to taking it up the ass, and quite the fellacitrice herself. But Guy enjoyed his sissies, and refused to give them up. Shirley refused to share a man with a man, although she was not averse to sharing him with another woman. So Guy and Shirley were no more than Guy and Brenda or Guy and Jennifer or Guy and so many others, man and woman.
Mrs. Bowen deeply resented this, but could not blame Guy. As the twig is bent, so grows the tree. After all, her granddaughters never reached sixteen as virgins, and everyone of them knew the taste of cunt as well as cock. Guy would have been a good catch, and a fitting heir to her part of THE ESTATE. But THE ESTATE was there to indulge its members, not judge them.
Guy was a few inches taller than Nathaniel, which made Ellen the same height in heels. As the kiss continued, Ellen could feel Guy's manhood rising. Knowing she was the cause of this caused her own manhood to grow. Ohmigod! she thought. How will he make me a woman with my cock sticking in the air?
Guy broke the kiss, a smile separating his mustache from his beard. Elaine and Brenda were smiling also. A happy Guy Hughes meant a pleased Mrs. Bowen; a pleased Mrs. Bowen meant a not unpleasant tomorrow or next week. "Are you ready?" Guy asked.
Everyone thought he was talking about dinner. "Yes!" Ellen said.
Guy guided her around the table and toward the doors. As they passed Elaine and Brenda, Brenda indicated that Ellen needed to fix her make-up. While they waited for the elevator, Ellen fixed her make-up while Brenda and Elaine watched from the doorway. For the first time that evening, Guy turned and acknowledged Brenda's presence, giving her a furtive wave just as the elevator arrived.
As the two got on the elevator, Elaine wondered why Mr. Hughes loved sissies. While not Elaine's type, he wasn't unattractive, was well off, personable, intelligent, well-traveled. Why fuck a man who looks like a woman when he could get the real thing? And did! She didn't ask herself how this was any different than a person who knows her clientele but does not understand them?
Brenda knew she would be speaking with Ellen before Ellen left. That morning, she wasn't sure at all. Mrs. Bowen was right; the Ms. Sharpe she'd brought to the office that morning was not the Ellen Sharpe who just got on that elevator.
"Ladies, don't you have homes to go to?" Mrs. Bowen asked, turning down the lights. She longed for the old days when THE ESTATE was founded, when all its members were either masters or slaves, and the only men who became women were slaves being put through their paces. How she had enjoyed laying the strap to their asses! But times change, and so do tastes. And finances. THE ESTATE's membership grew in size and diversity. Different needs required larger facilities; larger facilities required more money; more money required more--and wealthier--members; more and wealthier members meant greater size and diversity; greater size and diversity meant different needs. Still, Mrs. Bowen would've liked to lay the strap to both Brenda and Ellen, and all the ladies in the tea room!
There are several dining facilities at THE ESTATE and in the county. The town with the regional airport was once a company town, and THE ESTATE still holds title to most of the commercial real estate. All of its restaurants, from the local McDonald and Burger King franchises to the coffee and donut shops to the French, Italian, Japanese, Mandarin, Indian and American restaurants were on ESTATE property. It is amazing that state planners did not question why so many different restaurants, of three star quality, existed in such a small town in a rural part of the state. Maybe the fact that each department head is given a complimentary weekend each year alleviates such questions.
But the town's restaurants do not compare with the dining facilities of THE ESTATE's Manor House. This was the robber baron's residence, now converted into the main administrative building. There are four dining facilities: the banquet room, the dining room, the breakfast room, and the servants' facilities. The banquet room was used for formal entertaining. Now it is the main restaurant. The dining room was originally for the baron's family meals when there were no guests. Similarly for the breakfast room, the only difference being their locations. The breakfast room faced east, the dining room west. The servants' facilities are self-explanatory. It is now the cafeteria for Manor House staff, from custodian to Lord of the Manor, the official title of the chief executive officer for THE ESTATE. All are served from the same kitchen, although the prices for the same dishes vary with the restaurant.
Guy had not decided which restaurant he would take Ellen to until he saw her. He chose the banquet room, mainly because the Manor House is in walking distance of Guest House II. As they entered the surrey, he was tempted to tell the driver to take them directly to Guest House II, but refrained. Making Ellen a woman included treating her as one. That included dinner and entertainment before he fucked her. Besides, she needed to know that she passed as a woman to others. And he wanted to show her off.
"Welcome back, Mr. Hughes," the maitre d' said when they entered, giving Ellen the once over. Knowing Hughes' sexual preferences, the maitre d' wondered what the woman on his arm looked like before the Transformation Services worked their magic.
"Thank you, Serge," Hughes replied. "The terrace, please."
"Of course, Mr. Hughes."
The maitre d' led the way through the banquet room to the doors that were part of the windows that formed the wall facing the lake. There were a dozen tables, all for two people, along the balustrade, with another dozen for larger groups. Hughes preferred the table at one of the corners, giving him and Ellen a view of the lake through the trees as the sun finally went down. The breeze from the lake also dispelled the summer heat.
Guy smiled as Ellen smoothed her dress as she sat down, Serge holding her chair. He never ceased to wonder at how quickly his dates adopted feminine mannerisms. He looked at Serge. "What do you recommend, Serge?"
"Chef is in a good mood today," Serge sniffed. "I don't believe any one should miss the opportunity to taste the lamb when he is in a good mood."
Guy looked at Serge in amusement. They were about the same age, had both been born in Toronto. Only then he was George. The family used the last name of Siffret, the closest English approximation of their Inuit name. He looked at Ellen. "Would you mind if we left the dinner to Serge's tastes?"
Ellen shook her head. Even Nathaniel wouldn't know what to do in this situation. Guy looked at Serge. "We place ourselves in your hands, Serge." The maitre d' bowed slightly and left.
The two of them sat there and looked at each other. The silence was awkward, but Ellen didn't know what to say. She kept remembering Brenda's advice to let Guy take the lead. Was that everything, or just when they went to her suite. She decided it was everything. This was his stomping grounds. She didn't know where she was, not just where THE ESTATE was, but where she was on THE ESTATE. She didn't know all the rules, or anything else. As she saw the waiters serving the other patrons, she saw the differences in shirts, vests, ties that denoted different ranks and status. She wanted to know more about THE ESTATE, and how Guy became involved.
"So, what do you think?" Guy asked.
"I don't know what to think, Guy," Ellen replied. "This place ... me ... you. Two years ago, I would've said no way. Two weeks ago I was thinking no way. But ... I'm here, aren't I?"
"Yes, Ellen, you're here." Guy answered. "And I'm very glad you are. You are very beautiful, and any man would be very glad to be with you."
Ellen didn't know how to respond. She felt flattered and reassured, but also slightly suspicious that she was being given a line. Nathaniel had said similar things with the same sincerity when he didn't mean a word of it. But Guy was with her in public. He had spent an inordinate sum of money for the pleasure of Ellen's company this weekend. And he was very pleased with her.
"How did you find this place?" she asked.
Guy relaxed at this. "I was wondering when you would ask about this place. The staff has probably been very non-informative when you asked them." Ellen nodded vigorously. "I inherited a membership." Ellen's quizzical expression informed Guy that further explanation was necessary.
"My parents died when I was twelve. Car accident. My closest relative was my father's only sister, who lived on a ranch in Alberta. So I left Toronto, where I had lived all my life, to raise cattle and wheat on the plains. My aunt had a sexual appetite you can't satisfy in rural Canada--or most other communities in North America. She was into female domination and multiple partners, a few other things in bondage and discipline. Her husband was the submissive type, but couldn't find dominatrices in Calgary or Edmonton or Butte or Helena on you side of the border. He'd come to Toronto about once every two months or so. One trip he met my aunt, next thing the family knows she's married to a well-to-do cattle rancher.
"That was before I was born. Turns out that after a while--a short while--the two of them needed more than each other. But the marriage was working in other ways. The neighbors stopped wondering when Uncle Jake was getting married, my aunt turned into a real good farm wife--good with the animals, helping out on even the rough jobs, a decent cook, satisfactory homemaker, not bad looking, friendly with the others in the county. Not wanting to run into family unexpectedly, they began making trips to Seattle, Chicago, Detroit, even New York City and Los Angeles. Lots of sex clubs catering to B & D. Word of this place kept popping up. Eventually, one of their contacts sponsored them and they became regular devotees. They died about twelve years ago, plane crash while returning from here. Being their sole surviving relative, I got the membership with the ranch."
As Guy spoke, Ellen just listen. Their dinners arrived, the lamb, salads, rice, wine. Ellen realized that Nathaniel could never afford a meal this good. Still she had questions.
"Did you know what you had inherited?"
"Yeah. You should know that it was fifteen years after I moved in with them before the plane crash. Aunt Peggy and Uncle Jake gave me the type of sex education you don't get in school. While a ranch is large, a ranch house isn't. I wasn't at the ranch long before I realized that my aunt and uncle did things in their bedroom ... and the tool shed ... and the barns ... that were not what my parents had done. Sometimes Uncle Jake looked more tired in the morning than he had the night before. When I was fourteen he caught me jacking off. He didn't say anything, but that night Aunt Peggy came to my room. She explained that Uncle Jake had seen me and that I shouldn't be ashamed of what I was doing. She reached under the covers and between handling me. Well, you were once a fourteen-year old boy. Some woman starts handling your dick and in no time you're shooting in her hand.
"Aunt Peggy said that that was okay, that's what she wanted to happen. For the next week or so she jacked me off every night. Then one night she came in and told me that there was a better way to shoot off than with a hand, either hers or mine. She then took her robe off and climbed into bed with me. She told me to climb on top of her. I shot all over her before I got one leg up. She said that was okay too. Then she had me lay back and called Uncle Jake. I thought he was gonna kill me. Instead, she threw the covers off of us and told him to clean her up! Without a word he came over and licked all my cum off of her. She then made him stand by the bed while she had me climb on her again. It was the third time before I was able to get inside her before I came, and then barely. Each time she made Uncle Jake clean her up. That became a routine for the next several months.
"She was the first to blow me, first cunt I ever ate. When they joined THE ESTATE, they would occasionally bring some of the members back to the ranch. While B&D was their thing, and THE ESTATE's purpose at that time, they'd bring back a couple with a submissive male and his dominatrix wife every now and then as guests. And she-male dominatrix as well. Only they weren't called she-males then. One time they brought back both a she-male dominatrix and her sissy boyfriend.
"I'd been fucking Uncle Jake doggy style for years by then. Aunt Peggy loved to see him bent over with a man's dick up his ass. The she-male wanted me to fuck the sissy while she did Uncle Jake. Missionary-style. It was as good as fucking a woman. She'd shaved all her body hair, and her skin felt soft and smooth. And she knew how to fuck! And kiss. I was hooked. A good looking sissy, who is passable as a woman in manners as well as looks, I'll go for her every time."
While Ellen was fascinated with Guy's story, she was also disturbed by Guy's use of the word "sissy." Guy saw the look on her face.
"Look, Ellen, a guy who goes around dressed as a woman is a sissy. You can call yourselves she-males, transgendered, transsexuals, whatever. To most people, I'm a sissy because I fuck men, although I'm always the top. Uncle Jake was always the bottom, but he was six three, hairy as a bear, and never wore anything feminine unless Aunt Peggy ordered him to. Which was every day." At this Guy chuckled to himself. "If any of our neighbors had found out about him, they would have called him a sissy too, although he probably could have kicked the ass of any man in the county.
"I use the word 'sissy' because its simple and obvious. No psycho terms. I usually stay away from 'top' and 'bottom.' I'm a sissy fucker, you're a sissy. That's why we're here."
Ellen couldn't deny Guy's logic. At least he wasn't calling her "bitch" and "slut." And he'd never hidden the fact that he considered men who fuck men as gay. Or that he wanted to fuck her. She put her silverware on her plate, wiped her mouth, placing the napkin on the table. Leaning back in the chair, she looked at Guy.
"Since that's why we're here, shouldn't we be doing it?"
Guy signaled Serge to bring the check