Postcards from THE ESTATE
Guy and Ellen
Part VII
Ellen woke feeling her arms and legs being moved. As she opened her eyes, she remembered that she had fallen asleep in Guy's arms, their legs intertwined. Suddenly she felt a dull throbbing in her ass, a reminder of her new status. Sissy. Guy's sissy. He'd fucked her twice last night, the second time with her wrapping her legs around him and throwing her hips up to meet his thrusts just like a woman, her heels digging into his ass, spurring him on.
Guy disentangled himself from Ellen, looking at her as he stood. She had been better than he thought she'd be. Good kisser. Great skin. Quickly learned to fuck like a woman. Initiated the second fuck. Fell as leep in his arms. As he looked down at her sprawled across the bed he regretted THE ESTATE's rule against unprotected sex. He would like to teach her to suck his cock, to feel her tongue laving his cockhead without the latex barrier. Yes, THE ESTATE had procured an especially sensitive condom especially for cocksucking, but there's nothing like the real thing. For that matter he would like to feel himself rubbing against her when he fucked her, to actually shoot inside her, not just inside a rubber inside her. But the rule was more than reasonable. After nearly a quarter-century of fucking sissies, he was HIV-negative, and had never had an STD. And the number of partners he'd had who had died of AIDS was greater than the number of sissies he'd womanized.
He looked down at himself, aware of the condom he was wearing. He peeled it off, then took a tissue and wiped himself. Leaning down he took Ellen's cock by the base and peeled her condom off. Gripping her cock firmly , he kissed her, running his tongue inside her mouth.
"Let's clean up," he said, breaking the kiss.
Ellen swung her legs to the edge of the bed, finding it awkward to stand with Guy continuing to hold her tightly. Partly pulling, partly leading, he led the way into the spa. As the water filled the spa, Ellen removed the wig for the first time. She was surprised that it had stayed on throughout their lovemaking. She removing the cap covering her own hair, running her fingers through it. She looked at herself in the mirror and was shocked at what she saw. Nathaniel, in worn make-up, false tits pointing at his reflection, a body shorn of hair, like a woman's. I am a sissy, she thought.
Guy came up behind her, wrapped his arms around her and pulled her to him, his cock fitting into the crack of her ass. He took her cock in his hands as he nuzzled her neck. Ellen just looked at their reflection in the mirror. There could be no doubt about them now. What sh e saw was her sissy self being made love to by the man who had just deflowered her. And she knew she would let him fuck her again and again and again.
Guy kissed her ears, looking at their reflection. He saw something different. He'd been here at least a dozen times, the moment when his lover realizes she will forever be a sissy. Last night was passion, the abandonment of social restrictions, the fulfillment of a role. Last night she was Ellen Sharpe, Guy's woman. This morning she is Nathaniel Spotswood, sissy. There was only one thing to do: fuck the sissy.
Guy released her, leading her to the spa. He helped her into the spa, then kissed her, their cocks pressing together. Nathaniel was Ellen again, throwing her arms around him as she returned the kiss. He turned off the water when it was about mid-thigh. Releasing her, he turned her around, guiding her to her knees.
"Rest on the cushions," he instructed.
She leaned on the leatherette cushion s on the edge of the spa, knowing what was coming. Guy took a condom from the boxes along the edge of the spa and put it on. Ellen felt his hands on her ass, then his fingers opening her, followed by his cock at her asshole, then sliding inside her. When his hairy balls met her smooth ones, she wondered why she had not felt them when he fucked her last night. She felt on hand move from the cheeks of her ass while the other reached around her and gripped her cock beneath the water. She lowered her head to her forearms and let him take her.
Guy moved between her legs, spreading them as he entered her. Once he had a firm grip at her waist and on her cock, he began pumping in and out, stroking her in rhythm to their fucking. When she rested her head on her forearms, he knew she had accepted her new status. He pressed deep inside her and stayed there, stroking her until she came. He bent and kissed the nape of her neck, trailing the kisses down her spine as she jerked in his hand. He began pumping into her again as she went soft, cumming several minutes after she had. He rested on her back, enjoying the smoothness of her body against his. He continued to kiss her neck, ears, shoulders as he slid his arms underneath her and alongside hers.
Ellen said nothing, letting him have his way. She was his, and her body belonged to him. Not that she would have had it any other way. She enjoyed the feel of his lips and tongue on her, his body against hers, his cock inside her, the way his balls kissed hers as he pumped her. She liked the way he jacked her off, holding her as she spurted into the water. She liked the feel of his shaft pistoning in her ass, and wondered how it would feel without the rubber. And as he became soft inside her, she was content knowing she had satisfied him.
Guy was very satisfied. He pulled out, pulling Ellen back with him to a sitting position, the water up to their waists. Ellen looked down at her false brea sts, wondering if they would come off in the water. Taking a chance, she lay down so that only her face was above the water. Well, her face and the tips of her breasts. She was tempted to play with herself, but refrained because of Guy. She just lay there, enjoying the scented water, remembering all that Brenda had said. Guy had been a wonderful introduction into womanhood. Being kissed and held like a woman. No being called bitch or slut or other degrading names. Even the word "sissy" was not pejorative when Guy said it. No pain at loosing her virginity, She had been made love to, not just fucked.
Guy removed the condom, tossing it towards the trash. It didn't quite reach it. He lay down next to Ellen, keeping only his head out of the water. He turned on the whirlpool and the two just lay there, letting the water swirl over them.
&nbs p; ***
"Have you ever thought about returning to Bernard?"
The question caught Brenda by surprise. She had just put on her ESTATE panty girdle and was fastening her stockings to the garters when Jennifer asked the question.
"Why?"
Jennifer sat up in the bed, pushing herself against the headboard. "You fuck real good. Pussy I mean. ... well, ass too. I mean ... well you've been Bernard longer than you've been Brenda. You must've gotten your share of pussy. Or at least some pussy. ... haven't you wanted to get some pussy again?"
"I thought I just did."
"Thanks," Jennifer smiled, scroutching down into the mattresses. "I mean real pussy."
"I thought you were real p ussy. You're turning into a real bitch." Brenda buttoned her shirt. She was glad she had brought an overnight bag with her uniform. It gave her about an hour to be with Jennifer, even if that hour was with Jennifer the bitch. Well, maybe just the last few minutes.
Jennifer smiled more broadly. "Thanks, again. To most people I'm a man who's had himself fixed. Big time. But to you, I'm a woman."
Brenda looked at her and wondered how anyone could see a man. Naked on the bed, her perky breasts pointing to the ceiling, her cunt pouting outward, the auburn hair neatly trimmed in a bikini cut, the smoothness of her skin, the shapeliness of her thighs and legs, to the red painted toes. Only her feet, man-sized 11s, belied her appearance. The feet and the hands. The surgeons should show her off daily, especially that cunt. It was better looking than most women Bernard had been with. And Jennifer was a better fuck.
Brenda stepped into her skirt, pulling it up a nd tucking the shirt into it. She didn't know whether she should be Brenda the counselor, Brenda the lover, or Brenda-I-gotta-job-to-go-to. She sat on the bed to put on her shoes. Three-inch pumps on the Fourth of July weekend. What a job.
Jennifer scooted forward, placed her arms around Brenda's shoulders, kissing her ear. "It's just that you fuck pussy so good, I wondered if you wondered about going back."
"Why would I want to do that, Jen? I can still fuck pussy, without changing back."
"Have you done that a lot?"
Brenda stood to put on her tie. As she tied a Windsor knot, but didn't pull it taut, Jennifer reclined on the bed again, legs spread, pointing her pussy at Brenda. A real cunt she is, thought Brenda. "You need to put a tampon in." Brenda advised.
Jennifer frowned. Brenda picked up her briefcase and shoulder bag, starting for the bedroom door.
"Brenda," Jennifer nearly shouted. Brenda stopped and turned to her. "You 'll be free after seeing them, won't you?"
Jennifer was referring to Brenda's current duty, to contact Guy and Ellen and make sure there were no problems from last night. If everything went well, then Brenda would not have to contact either of them until tomorrow morning. The rest of the day was hers. She did not immediately answer Jennifer.
Jennifer didn't wait for an answer. "Please come back afterwards, Bren. Please!"
Brenda looked at the tear-filled sorrowful face across the room, remembering the time she wanted someone about to walk out a door not to leave, or if they had to, to come back later. And she wanted to come back to Jennifer.
"We'll see, Jen," was all she said. Turning, she left.
Brenda picked up the phone reluctantly. This was the part of her job she always dreaded. Most times, the dread was unnecessary. Guy was a good lover. Brenda and Jennifer could both attest to that. But not all crossdressers moved easily into being sissies. Until that first penetration, neither THE ESTATE, Guy, Brenda, anyone knew how Ellen would react. When it goes good, it goes great. But when it went badly, it was a disaster. She dialed Ellen's room.
Guy had sat Ellen on the cushions on the edge of the spa, placed one of the cocksucking condoms on her and was expertly mouthing her cock when the phone rang. Who could be calling me at this moment, Ellen thought. Guy knew, so he stopped sucking and got out of the spa. Ellen wanted to shout 'Don't stop.' She was just getting into having her shaved skin tickled by the hairs on Guy. Sh e liked the way the hair felt on the back of her calves and thighs as she draped her legs over his shoulders. She appreciated the way Guy tongued her balls and thighs, and perineum. She wished her tits were real so he could nurse at them. And just as she was learning how to enjoy a blowjob, he quits!
"Hello, Brenda," he said into the phone.
"Good morning, Mr. Hughes," she replied. "Is everything satisfactory?"
"Very satisfactory, Brenda."
"I'm glad to hear that, Mr. Hughes," she continued, relieved. "If I remember correctly, a picnic is in order."
Guy smiled. For a really attractive sissy, one who looked good in dresses that revealed shoulders and backs and had good legs, Guy liked to take them picnicking on the Sunday following a defloration. Both Brenda and Jennifer had been treated to a picnic. There was a special spot, overlooking the lake, secluded yet open. It was at these picnics that Guy permitted--no, instructed--his new woman how to suck cock. Yes, Ellen would take a cock in her mouth for the first time this day--his cock.
"Yes, Brenda, a picnic is in order."
"I can order the picnic now, if you like?"
"Please do."
"Should my maids attend to Ms. Sharpe?"
"Yes, have them come up."
"Will five minutes be okay?"
"Five minutes will be fine."
As he put down the phone, Guy saw Ellen looking at him. She had gotten out of the spa and had a towel wrapped around herself. "That was Brenda," he said. She just looked at him with that I-heard-you-say-her-name-so-I-know-who-it-was look. "She's arranging a picnic. ... She'll be up in five minutes. ... With the maids."
All this Ellen had already figured out. What she didn't understand was why. She thought she and Guy would spend the rest of the day having sex. And her cock was still hard. In fact, it was tenting the towel, giving her a most unladylike profile. Guy was just about to mention it when the doorbell rang. Damn that Brenda! Why is she always so punctual?
Guy opened the door, standing aside as Brenda, Chantrelle and Adriane blew past him. Ellen was leaning against the doorframe of the spa, looking more than a little peeved. The three of them looked at her and saw Nathaniel, sissified, with a tent where Ellen's pussy should be. All three were very amused. Their smirks caused Ellen to look at herself, then blush.
"Did we interrupt something, Mr. Hughes?" Brenda asked, her amusement not the least bit masked. Guy looked toward Ellen, noticing the bulge. Now it was his turn to crimson. "Would you like Chantrelle to take care of that?" Chantrelle's smirk became smirkier, if possible.
"No, I'll handle it," Guy said, crossing over to Ellen.
"I'm quite sure you will, Mr. Hughes," Brenda said, causing the maids to titter. Guy guided Ellen into the bedroom.
Ellen was not sure what was going on. Guy practically pushed her into the bedroom, ripped the towel off her, pushed her onto the bed and practically attacked her cock, without a condom. This blowjob was industrial strength. Guy took the head in his mouth, applying very powerful suction. He jacked her with one hand, running his thumb along the underside of her penis. The tips of the fingers of his other hand he inserted just inside her asshole, twisting them just inside. In less than three minutes she came, flooding his mouth. She swooned, he swallowed.
He dressed as she recovered. "They should be finished in about an hour. I'll pick you up then."
Guy stopped at the suite door before exiting, taking one last look at Brenda. He'd not had an African-American sissy, or an African-Canadian one, since his last time with her. He'd invited her to his ranch, only to find out that his neighbors were racist as well as homophobic. She passed muster as a woman, only to have his neighbors and friends question why he wanted a Black woman aft er she left. He hadn't picked up on their attitude, but she had. She knew she could never be what would be acceptable to Albertan cattle society, so she said goodbye to Guy and entered the service of THE ESTATE like a spurned woman entering a convent. Guy never forgave himself, nor lost his lust for her.
Chantrelle and Adriane looked at each other knowingly as the door closed behind Guy. Chantrelle's first day as a maid had been spent preparing Brenda for her defloration by Guy. Adriane had helped Brenda relieve her sexual frustrations during her early days at THE ESTATE. As members, their relationship with Brenda was more like concerned aunts than subordinates.
Brenda stared at the closed door momentarily, thinking about what could have been, then turned and went into the bedroom. Seeing the towel on the floor, Ellen laying on the bed, her wilted dick with its telltale traces of saliva and cum, Brenda surmised what had happened. She hoped that Guy didn't do this often. Just because this was Ellen's first time with a man didn't mean she was HIV-negative or STD-free.
"Ready, Ms. Sharpe?" she asked, not aware of the edge in her voice.
Ellen was well aware of it. What had Guy said. He wasn't a one-woman man. But Brenda had said she and Guy were history. Was history repeating itself? Ellen pushed herself up, then stood, then strode across the room and out the door. She crossed the living room into the spa, waiting for the next step. The maids followed, subjecting her to a third depilation. Her nails were buffed, and a new coat of polish applied to both her fingers and her toes. After Chantrelle guided her back to the bedroom, both maids began cleaning the suite.
Brenda looked at Ellen as she entered. "Ms. Sharpe," she began. Ellen looked at her with defiance, believing she was about to be verbally abused. "I know sometimes the heat of passion makes us forget basics. But you must remember the times in which we live. We--you, me, the maids, Guy--are gay. While no disease is limited to gays, we are more susceptible to certain diseases than others. And for one of them we know there is no cure, and that it kills. What you and Guy did a little while ago probably is more dangerous for you than it is for him. Remember, you are not his first, though he was yours. We are very careful about disease at THE ESTATE, and so far Guy has passed all our tests. But tests are not perfect. So, please, for your own sake, take advantage of the precautions we make available."
Ellen felt foolish. She had mistaken Brenda's concern for jealousy. Nathaniel never thought about HIV or AIDS, why should Ellen? Because Ellen had entered a new world, where both HIV and AIDS were a reality, much more so than in the world Nathaniel knew. She nodded her thanks.
"I'll let you do your own make-up," Brenda said. "Remember, you're going on a picnic."
Ellen looked at Brenda, trying to read her fa ce. By now Ellen realized nothing at THE ESTATE is as simple as it first seems. What was special about this picnic? She tried for a fresh-faced country girl look, using only a light lipstick and face powder. Finished, she turned to see what Brenda had selected for her to wear.
Brenda had selected a pink-and-white floral print sundress empire-waisted with spaghetti straps. Another dress to show off the false boobs. And her legs. The dress ended at mid-thigh. Ellen looked around for the underwear. Brenda handed her a pair of panties.
"Can't wear a bra with this, and hosiery is impractical at a picnic." Brenda tried not to sound smug, flippant, or snide. Ellen felt the comment was smug, flippant, and snide. She stepped into the dress, letting Brenda zip up the back. "Get on the bed on all fours," Brenda ordered.
Ellen looked at Brenda, then did as ordered. She felt the dress being flipped up and her panties being pulled down. She then felt something cold and greasy being pushed into her. The panties were then pulled up and the dress down. A pat on the buttocks informed her that the procedure was finished. When she turned around, Brenda was holding a much larger tampon than had been used the previous day. "I see you haven't been replacing the tampon afterwards." Brenda chided her. Ellen was tempted to let her know she had not yet had an afterwards. "You're no longer a virgin, Ms. Sharpe," Brenda started. "You'll need to use a larger tampon from now on." She then picked up a jar of cream identical to what had been used the previous day. Or so Ellen thought.
"This is a different cream than we used yesterday. In fact, it's the exact opposite of what we used. That cream was meant to make it easy for Mr. Hughes to enter you with as little pain to you as possible. Now that you've been opened up, this cream is to close you as much as possible with safety. You will never be as small as you were before," Brenda paused, "a nd anyone who sees you naked from behind will know you've been fucked there." Brenda let this last sink in.
'I'm a sissy, and anyone who sees me naked will know it,' Ellen thought. No showers at a gym, or swimming or anything where he would have to be naked with other men. Hell, Nathaniel never did those things anyway. And since Ellen did not ever again intend to have body hair, explaining her enlarged asshole would not be a problem.
Brenda produced a fresh wig cap and a new wig, this one straw blonde reaching below Ellen's shoulders. When it was in place, Ellen looked at herself in the mirror and saw Nathaniel's favorite wet dream. Brenda produced a pair of wedge mules, a big straw hat and matching straw tote bag completed Ellen's outfit. Looking inside the tote bag, Ellen saw a box of the larger tampons, a jar of cream, and two packages of rubbers, one for anal intercourse and one for oral sex. The doorbell rang just as the two of them entered the living ro om. Brenda opened the door, letting Guy in. He took a good look at Ellen, then rushed to her, taking her in his arms as he kissed her again. Without a word he whisked her out the door. Brenda would not have been surprised had he taken her right then and there.