Postcards from the Estate The Womanizers: Guy and Ellen Part X
Ellen woke staring at the high back chair, with the sun streaming into the window. As she felt Guy's shriveled dick against the crack of her ass, she knew she would never use that chair. They had spent hours fucking missionary style with her never permitting him to leave her ass as long as she could get him hard by tightening her sphincter, moving her body, using her hands, and her kisses. It was only when an exhausted Guy suggested they go to sleep spoon fashion with his half hard dick in her ass did she relent. And even then he used his hands for the better part of an hour bringing her to the brink then retreating before he let her cum. This was how they fell asleep, his cock limply up her ass, his hand on her cock. And this was how they awoke.
Ellen was the first to get out of bed, turning to kiss Guy before repairing to the spa. As she settled into the water, she noticed that the edges of the breasts were coming loose. She quickly bathed herself, got out of the spa and into a terry-cloth robe. As she was exiting, Guy passed her going into the spa, answering an urgent nature call.
Back in the bedroom, Ellen opened the robe and looked at her breasts in the mirror. What had Elaine said, that they would sort of fall off on Monday. And this was Monday. She looked at her reflection. Nathaniel. No wig, no wig cap, no make-up. A man with a limp dick and false boobs about to fall off. She quickly closed the robe when she heard Guy coming.
The expression of horror and anxiety on her face Guy had seen often. He came up behind her, embracing her in a bear hug. "The party's over and Cinderella's pumpkins are going squash?" He joked. He reached inside her robe and fondled her dick. "You'll always be Ellen to me, no matter what you look like."
He released Ellen's dick, kissed the back of her neck, and removed her robe. He turned the now apprehensive Ellen around, backing her into the vanity. He looked down between them. He was flaccid, she was rampant. Smiling, he looked at her.
"What did Jennifer and Brenda tell you to do? Drain me so I couldn't fuck for a week? Congratulations."
Taking one of the fellatio condoms out, he placed it on her dick, then stepped into her, kissing her. "As you give, so shall you receive. Those who give pleasure shall receive pleasure. I can't fuck you anymore today, but I can make sure you're as drained as I am."
He trailed the kisses down her throat, chest, stomach, until he was on his knees before her. Spreading her legs, he licked the inside of her thighs, running his tongue over her balls and as far behind them as he could. He returned to the base of her shaft, kissing the skim between her balls and the base of the condom, working his way to her cockhead. This he took in his mouth and began sucking intensely, inserting his fingers in her ass as he did so. With his other hand he gripped her cock, rubbing the underside with his thumb.
Ellen looked down on him in both amazement and pleasure. Twice yesterday she was in this position before him, and twice she thought herself his sissy for being in that position. Yet here he was in the same position and she could not think of him that way. It was more than the fact that she was wearing panties and lingerie and makeup and a wig when she blew him. When he sucked her cock, he was a man giving pleasure to his woman. When she sucked him it was as a sissy cocksucker. This distinction existed in Ellen's mind, not in Guy's, but it existed.
She had to brace herself by grabbing the edge of the vanity as she began to cum. Between Guy's mouth and his fingers, she could not resist. As she filled the condom, Guy kept twisting his fingers in her ass, maintaining his suction on her cockhead. He removed his fingers from her ass, stood and kissed her, continuing to rub her cock with his thumb. Seeing that she remained hard, he broke the kiss.
"I'm going to have to get you to the ranch where I can properly satisfy you," he grinned.
He stepped back and removed the rubber. Ellen continued to ooze cum. Guy wiped her dick clean, placed a fucking condom on her, and proceeded to jack her off again, bringing her body to his at an angle so he could kiss her again as he jacked her. Ellen responded by placing her arm around his waist, maintaining full body contact as she continued to cum and cum. She was barely conscious of Guy removing the condom, wiping her clean, putting on another condom, and jacking her again, twice more. Only when he suggested they shower did she look down at her cock in his hand, surprised to see the multiple discarded rubbers and tissues on the floor. She was surprised she had cum so much, and even more surprised when Guy blew her again in the spa, and she came twice more.
Brenda knew she should stop Jennifer. Jennifer was sprawled across her bed, her torso between Brenda's legs as Jennifer sucked on Brenda's naked cockhead. Jennifer's right hand gripped the shaft of Brenda's cock, the tips gently rubbing the underside. Jennifer's left hand was buried in Brenda's ass to the wrist as Jennifer massaged the dark-hued trans' prostrate.
They had spent the night putting into practice what they had preached to Ellen, only with Jennifer using her pussy where Ellen was using her ass. All with the proper protection. They had fell asleep face-to-face with Brenda inside Jennifer, Jennifer's leg around Brenda in a repeat of their first fuck. Brenda had awaken to Jennifer's kisses: mouth, chin, throat, chest, navel, belly, pubic hair, balls, thighs, perineum, balls. When Jennifer removed the soiled condom, Brenda half-knew that Jennifer was going to suck her bare.
Jennifer teased her first, licking the shaft, fingering her asshole, kissing her balls. Brenda knew she should have stopped Jennifer when the transsexual began licking her congealed cum. But she didn't. Emboldened, Jennifer pushed first one finger, than two, three, her whole hand, in Brenda's ass while she became more aggressive orally. By then, Brenda could not have stopped her if Brenda had wanted to. And she didn't.
And so here they were, violating every rule of THE ESTATE about unprotected sex. Jennifer could have kept Brenda on the brink forever--or nearly so. But Brenda couldn't wait that long. The sunlight streaming through the window already informed her that she was late going to Ellen's. Very late.
"Jennifer, please," she begged. "I need to go to work."
Jennifer removed her mouth, while continuing to massage Brenda's prostrate. "You're really going to work?"
"Yes, Mrs. Thierry, I'm going to work," Brenda replied, runnig her hand through Jennifer's hair as she guided the new woman back to her cock. "That's what I do here. Today's very important--for Ellen or Nathaniel or whichever one is there. You should know that. Ellen will have to decide what to do about Nathaniel and Nathaniel what to do about Ellen. Maybe they've already decided. But I got to be there for him or her or them or whatever. Now finish what you've started."
Jennifer returned to the work at hand--and at mouth. Brenda had been right about one thing--Jennifer was a cocksucker. She kissed the cockhead, then licked it, then swirled her tongue around it. Pursing her lips, she kissed the tip again, only pushing her head down so that the cock parted her tight lips until they met just beneath the head. Brenda came at the same time, a dry cum with her cock twitching in Jennifer's mouth. Jennifer kept sucking until Brenda went soft, then removed her hand from Brenda's ass as she released Brenda's cock.
Brenda had to catch her breath before she swung her legs over the edge of the bed. Jennifer was standing, her left hand soiled, her make-up smeared. Most of her lipstick was on Brenda: mouth, face, throat, body, cock, balls, thighs. Especially Brenda's nipples. Both Jennifer and Brenda had tested Brenda's claim that nipples are a prime erogenous zone on both man and woman. As Brenda looked at Jennifer, she too saw that most of her lipstick was on the white woman. Lips, throat, breasts, stomach, thighs. Wordlessly they both entered the bathroom and stepped into the shower.
Brenda wanted to take a quick shower. Jennifer wanted to caress and be caressed under a stream of hot water. The shower took longer than Brenda wanted; Jennifer caressed and was caressed less than she cared for. Brenda had to take the towel from Jennifer when Jennifer's offer to dry Brenda resulted in more of Jennifer's lips and hands on Brenda than terrycloth.
Jennifer sat cross-legged tailor style as Brenda dressed. She marveled at THE ESTATE panty-girdle. She had tried that garment several times herself, only to be frustrated at its intricacies. Watching Adriane and Chantrelle assist each other into and out of it had proved to be interesting.
"Want me to lace you up?" she offered.
Brenda thought about it for a moment. She could easily close it herself, but having it laced was always an intimate exchange. She laid on her back with her legs splayed. Jennifer knelt between them, cinching and tightening first the region between Brenda's legs, than the side on the right. Jennifer now realized that the maids removed the entire front panel, requiring the entire codpiece to be fitted and laced. So this is how the mistresses get in and out of these things so easily. They close it like a fly.
Finished, she rolled Brenda's stockings on her, fastening them to the garters. Next came the padded long-line bra. As she hooked the front, Jennifer kissed Brenda's chest before each closure, then threw her arms around her and frenched her. Reluctantly, Brenda broke the kiss and pushed her lover to the bed. Jennifer lay back, her breast pointing to the ceiling, her cunt on open display, as Brenda donned her blouse, skirt, vest, and tie.
'Damn her,' Brenda thought. She wanted her cock back in that cunt, and more telling, back in her mouth. For the first time in years, she thought about being Bernard. But there were reasons for being Brenda. She enjoyed being a woman. She enjoyed the options of what to wear when away from duty. She enjoyed the way men--and women--looked at her as she strolled. She enjoyed not having to fulfill some macho role constantly, although fulfilling a feminine role constantly did not bother her. And she enjoyed being fucked as a woman by a sissy fucker who knew how to fuck a sissy. Like Guy. Or Cleveland. Or Adriane. Or Chantrelle. Especially if they were good cocksuckers. And now here was a cunt she could fuck too. She sat on the bed to put on her pumps.
"What time do you think you'll be finished?" Jennifer asked.
"The bus leaves at 3:00 p.m." Brenda replied.
"I'll have dinner ready when you return," Jennifer said.
Brenda looked at her. "You're taking a lot for granted, Mrs. Thierry."
"Yes, I am, Ms. Duncan. I need you, you need me. I want you, you want me. Come back to me tonight. Please. We need to talk."
God, Brenda thought. We need to talk? Real woman or transsexual, why do they use that same old cliché? She picked up her briefcase, THE ESTATE in its Roman letters, her name in the lower right corner of the top. Shoulder bag with purse inside. She looked into the mirror. She could put on make-up at the guest house. Even without make-up, she now looked more feminine than masculine: shoulder-length hair, arched eyebrows, lips discolored by traces of lipstick, the hint of eye shadow and foundation. She turned, kissed Jennifer lightly, and headed for the door.
"This evening, Brenda," Jennifer shouted as Brenda opened the door. "I think I'm pregnant," she shouted as the black woman closed the door behind her.
Adriane looked at the clock in the kitchen of Guest House II. 11:00 a. m. Brenda should have been there two hours ago. Adriane looked at Chantrelle, the same worried look on the second maid's face. This was most unlike their favorite mistress. Each debated within her own mind whether to call Jennifer's, Mistress Elaine, even Mrs. Bowen. No, never Mrs. Bowen! It was with both relief and concern to them that Brenda walked into the kitchen. She nodded at them then picked up the kitchen phone.
"Mr. Spotswood, this is Brenda. It is time I came up." She listened briefly. "No, Mr. Spotswood. Ellen has had her moment at THE ESTATE. Mr. Spotswood must return to his old life. Only then can he decide what to do about Ellen. Do you understand, Mr. Spotswood?" It was several minutes before Brenda spoke again. "Good morning, Mr. Hughes. ... It seems Ellen doesn't want to leave. ... Five minutes will be fine, Mr. Hughes."
She hung up the receiver and sat at the same table as the maids. Pouring herself a cup of coffee, she looked around the kitchen. Four cooks, assorted menial help, waiters. She looked at the two maids. "Okay, you two. What's up?"
The maids looked at each other in bemused bewilderment, eyebrows raised in mock innocence.
"Mrs. Thierry." Brenda said.
They smiled at each other. They alternated speaking. "She was lonely. You were lonely. We thought the two of you ..."
"What else?"
"What do you mean, Mistress Brenda?" Chantrelle asked in mock ignorance.
"There's something more than a lonely transsexual and a lonely sissy getting together going on here?
"Well, didn't she discuss her conversation with Mrs. Bowen with you?"
"Mrs. Bowen!" Brenda could barely control herself.
"Oh yes, Mistress Brenda. Mrs. Bowen had a conversation with Mrs. Thierry. With us too," Adriane indicated her and Chantrelle. "We suggested to Mrs. Thierry that she broach the subject to you. From the way you two have been behaving over the last couple of days, we thought she had, and you'd agreed."
Brenda looked at the clock. There was just enough time to reach the suite before five minutes had elapsed. She hated being late.
"We'll talk later," she said, standing. The two maids smiled smugly as they followed her out of the kitchen
Brenda looked with satisfaction on the clothing strewn from the door to the bedroom. Ellen and Guy were at the cafe table by the wall, the remains of a full breakfast on their plates. Guy was dressed; Ellen was in her robe. Or rather Nathaniel was. The maids began picking up the clothing. Brenda sat in an armchair, waiting. Guy, knowing the drill, coaxed Nathaniel onto the loveseat, while he remained standing. Brenda looked at Nathaniel, then Guy.
"Ellen wants to remain Ellen," he said.
"Congratulations, Mr. Hughes" Brenda said. He had made a woman out of Ellen--so much that she didn't want to be Nathaniel again. "Have you explained that he must go back as Nathaniel?"
"I've tried," Guy sighed. "I don't think I've gotten through."
"Are you ready to leave, Mr. Hughes?"
"Yes."
"Do you plan on contacting Ellen in the future?"
"Yes," he replied, looking at Nathaniel. "I do want to see Ellen again."
"Then I think it's best if you leave now, Mr. Hughes." Brenda said. She had done this drill before also.
"May I kiss Ellen goodbye, Brenda?" Guy asked. He was sincere in his desire and intention of contacting Ellen, but knew that Brenda would advise him later whether or not that was a good idea. This would be the first sign of which way things would go. If Brenda believed that no future contact was advisable, she would say no.
"That's up to Mr. Spotswood." She turned to him. "Mr. Spotswood, Ms. Sharpe may kiss Mr. Hughes goodbye, if she so chooses."
Nathaniel realized that Ellen and Guy were parting, maybe never to see each other again. He wondered if he should put on a wig, at least pretend he was still a woman. Neither Brenda nor Guy moved. With tears in his eyes, he stood and faced Guy.
"Ms. Sharpe would very much like to kiss you, Mr. Hughes." He couldn't say the word "goodbye."
Guy took him in his arms and kissed him the same as the first time in Mrs. Bowen's office. After a few minutes, Guy broke the kiss.
"Thank you for a wonderful weekend, Ellen Sharpe. I hope it's not the last we see of each other."
"Thank you for making me a woman, Guy Hughes," Ellen/Nathaniel replied, tears streaming down his face. Guy released her, turned and walked out the door without looking back. Nathaniel crumbled onto the floor.
Brenda let him cry. She'd been in that same position two years ago. She'd watched several others in that position over the last year and a half, including Jennifer only yesterday.
Chantrelle appeared at the bedroom door when Guy went out the front door. "Mr. Spotswood's clothes are laid out, Mistress Brenda."
"Run Mr. Spotswood a bath, Chantrelle," she ordered. She helped Nathaniel to his feet, moving them to the loveseat, placing her hand on his shoulder. This was the reason she was hired. Not every member or guest can transition from the roles they adopt at THE ESTATE and the lives they must lead normally. Each service has counselors to help assist in the return to normalcy. For Transformation Services, the counselors are also transgendered. Advice is both easier to give and more readily accepted when the member/guest knows that the person advising them has been through what the member/guest is going through.
"Cinderella, the ball's over," Brenda cooed. "Time to go back to the cottage and the mean stepsisters. I know it's unfair, but such is life. You've still got the glass slippers. Now, let's take a soothing soak and get Nathaniel ready to face tomorrow."
Nathaniel slowly sat up and looked at Brenda. "Why can't I remain as Ellen, like you remained as Brenda?"
"Well, Mr. Spotswood," Brenda began, pulling him to his feet. "I was Brenda long before I met Mr. Hughes." By now they were at the spa door. Brenda removed the robe as she propelled him toward Chantrelle and the water. Chantrelle eased him into the water. "Just sit on the edge while Chantrelle removes these," Brenda said, touching his breasts. Chantrelle applied a lotion underneath the fraying edges of the breasts, lifting and applying more lotion. It took about fifteen minutes for both breasts to be done.
"Now just soak and enjoy the water." Brenda advised.
As Nathaniel sank into the water, Chantrelle began washing him with one of the natural sponges that are always available. In addition to washing the lotion and the remnants of the adhesive from his chest, she also washed his face rather roughly, removing most of the make-up and returning his eyebrows to their natural shape. As Chantrelle worked, Brenda began bringing Nathaniel back to reality.
"Mr. Spotswood, you came here as Nathaniel Spotswood, you must leave here the same. Your return ticket is in that name, all you identification is in that name, and you would have a very difficult time at the airport with all the security you now undergo due to 9/11.
"The second reason THE ESTATE wants you to return as Mr. Spotswood is we want you to spend at least a week, hopefully two, as a man. Drink beer, go to baseball games, fuck girls. Try not to wear panties, or hosiery, or nightgowns. And please stay away from make-up! For this reason, all the clothing, and make-up, and other things in the bedroom will not be sent to you for two weeks. After that, they will be sent, even if you request that they be returned to Mr. Hughes. They are yours. Is that clear?"
Nathaniel nodded. It was like the first night in reverse. Chantrelle pulled him from the spa and began drying him. Brenda continued.
"Mr. Hughes will not contact you during this two week period. I advise against you contacting him. Mr. Hughes was very pleased with Ellen and wants to see her again. When he said that he was sincere. Ellen needs to give Nathaniel the opportunity to be Nathaniel again. Two weeks is not too long for Ellen to rest. She's had a very exhausting weekend!"
Brenda wasn't sure if Ellen would remain in the closet even until tomorrow morning. More than one sissy had left THE ESTATE macho only to arrive at their destination airport en femme. She hoped Nathaniel would follow her advice. She too liked Ellen, and wanted Ellen to enjoy a week at Hughes' ranch. Brenda looked at the washed and dried Nathaniel. Not a bad looking guy, she thought. But so were Bernard and Marcus. It takes a good looking guy to make a good looking gal.
"One more thing." Brenda pointed to the tampons. Chantrelle produced one, coated it with cream. Both looked at Nathaniel, who bent over to let the maid insert it. "You should use one daily, except when you're with a woman. Chantrelle and Adriane will help you get dressed."
The tall trans led him into the bedroom where Adriane had laid out his clothing: boxers, T-shirt, chinos, short-sleeve plaid shirt with two pockets, hiking boots, wide black leather belt with 2x4 inch buckle. As he put on the clothing, Nathaniel thought they were overdoing the macho image. Talk about camp! If he could read minds, he would have read the same thought in Brenda's head. Mistress Elaine's image of a he-man. A real woman's image of what makes a man being as erroneous as a man's image of what makes a woman.
Brenda escorted Nathaniel to the lobby where the two waited for the bus. It would be another two hours before the bus left. They could have waited in the suite, but Brenda thought it best that Ellen be left in those rooms and Nathaniel began preparing for tomorrow. But she knew that Nathaniel had to be aware of why he could not be Ellen forever immediately. She had spent Saturday turning Nathaniel into Ellen psychologically; now she must reverse the process.
"Mr. Spotswood, you asked why you couldn't remain Ellen. What I said upstairs is what I am required to tell you. And I meant it. You should give Nathaniel a chance to re-emerge. But you should also think about never letting Ellen live again."
Nathaniel looked at her in horror.
"As I said, I was Brenda before I met Mr. Hughes. Mrs. Thierry would have had her operation even if she had never been with Mr. Hughes. Ellen is a creation of Mr. Hughes. You probably never would have done anything more than wear women's clothing in the privacy of your apartment but for him. Now, you've had a weekend as a woman, including being fucked as one. Consider this a sexual experiment--one that went well."
Confusion clouded Nathaniel's face as tears flooded his eyes.
Brenda continued. "As I said Saturday, Mr. Hughes is a wonderful introduction to the sissy lifestyle. Now I must inform you that this is as good as it will ever be. You should realize that your initial disgust with your contacts on the web are justified. Most sissy fuckers are not Guy Hughes. Most deny they are gay, and will be violent to the sissies they fuck for exposing this side of their sexuality. Most do not think it's rape to force a man to suck them or to force themselves on a man anally. Most are as verbally abusive as they are physically abusive. And many gay cruisers are also gay bashers. Just because Ellen was not raped or brutalized or verbally abused at THE ESTATE doesn't mean she's safe elsewhere. Are you following me. Mr. Spotswood?"
Nathaniel nodded, in shock. Never be Ellen again! That meant never being with Guy again. "Couldn't I just be Ellen for Guy?"
Brenda sighed. Ellen would not be closeted. "That will be months from now, if ever." She looked intently at Nathaniel's face, reading the doubt and confusion. "What do you intend to do with Ellen until then?"
Nathaniel stared at her blankly. He now realized that his life was back to what it was a month ago, except now he knew how pleasant it was to be a woman--a young, attractive woman.
Brenda guessed his thoughts. ""Mr. Spostswood, I suggest that you don't go out as Ellen until you can be with Guy again. You must treat Ellen as your little sister--make sure she doesn't go where she is not safe, get into situations she cannot handle. Most men will see Ellen as what she appears to be: a pretty woman. There are the rapists and stalkers, who would prey on her and all women: the Sons of Sam, the Ted Bundys. So Ellen must protect herself as any woman would, especially one who is young and pretty.
"Then there are those who will hit on her thinking she is a woman, who will become violent when they find she isn't. So you see, Ellen must be careful as a woman and careful as a sissy. And then there is the use of condoms. AIDS is still very much out there, and very much among gays. Also syphilis, gonorrhea, hepatitis and other sexually transmitted diseases. Many infected men deliberately infect others. You--and only you--are responsible for your health. And safety."
"So if you want Ellen to be with Guy again, I suggest that Ellen save herself for Guy. No one else. Don't even go out as Ellen."
She saw a glimmer of hope in Nathaniel's eyes. He had not considered being with anyone else as Ellen, and the thought of saving Ellen for Guy appealed to him. But he wanted Ellen to strut her stuff until then. The dangers Brenda has listed had not occurred to him. Maybe two weeks is time enough to plan Ellen's coming out at home.
Brenda's voice startled him to reality. "I'll be calling you every day for the next two weeks, Mr. Spotswood," Brenda informed him. "Just to see how you're doing."
Nathaniel found this comforting. He was not sure whether he would be Ellen or Nathaniel when she called, but he knew he wanted to talk to her whichever one he was.
At about two p.m., Cleveland walked into the lobby and signaled the desk clerk that he was ready to be boarded. As he turned to leave he nearly bumped into Brenda and Nathaniel.
"Good afternoon, Mistress Brenda," he said politely. Damn she looks good. If I didn't know she had a dick ...
"Good afternoon, Cleveland," she replied just as politely. Too bad he's such a homophobe, she thought. He could give Guy some pointers on fucking sissies.
Cleveland looked at Nathaniel. Except for the extremely close shave he seemed to have, Cleveland could not see Ellen, although he looked hard for her. The bus driver wondered if there was a tampon sticking up his ass. Only the overnight case Nathaniel carried onto the bus indicated the nature of his visit.
Brenda hugged Nathaniel just before he boarded the bus. This is usually frowned upon, but Brenda had a certain leeway as a counselor. The hug she got from Sylvia was different, and unexpected. Sylvia always wanted to know what sex with a man was like and she also wanted to know if what they said about the size of Black men was true. What better way to satisfy both curiosities than with a Black she-male?
The other passengers were Mrs. Mettrinos, Senora Mendez, Ms. Bradley, two couples in their forties whose sexual preferences were masked under veneers of middle-class, middle-age respectability. No Harrises. No Ms. Trevor. Jeffrey was behind the bar, looking only slightly less worn than Ms. Bradley. Sylvia smiled at Mrs. Metrinos, who had been a very, very bad girl that weekend. Sylvia gave the sign to Cleveland, and he pulled the bus into the street.
-000-
Author's Note: This is the last part of "Guy and Ellen." What happens to Guy and Ellen in the future happens off premises, so would not be suitable for Postcards from THE ESTATE, which chronicles only what happens at THE ESTATE, and how the members, guests, and staff got there for any particular visit. As for Brenda, Jennifer, Chantrelle, Adriane, Elaine, Mrs. Bowen, the ladies of the tea room, Sylvia, Cleveland, Jeffrey, Ms. Trevor, Mrs. Metrinos, Ms Bradley, all the members, guests, and staff of THE ESTATE--who knows what postcards the postman will bring.
Postcards From THE ESTATE: Guy and Ellen, Part 10. 1