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Daphne By Eugene Webber FARBER, UNDERWOOD, CARRUTHERS, KINSHAW, YOUNG, OSWALD, UPDIKE PLC MEMORANDUM From: Management Committee To: All Partners, Associates, and Staff SUBJECT: Second Annual New Year Eve's Party As this city's first transgendered firm, the Management Committee wants to congratulate the partners, associates, and staff of Farber, Underwood, Carruthers, Kinshaw, Young, Oswald, Updike on another successful year-successful financially and professionally. Last year's New Year Eve's Party was very successful, much more than we anticipated. This year we have booked THE ESTATE for the festivities. Transportation will be provided. *** Howard Melrose, vice-chair of the management committee, was very pleased with the memo. He did not want a repeat of the events of last year's party. *** "Daphne!" Gladys shouted above the din. Daphne, well attuned to the sound of her boss's voice, turned to see the trio sitting in a nook like Shakespeare's witches. Gladys waved the staffer towards them. "Can you drive?" her supervisor asked when Daphne reached them. Daphne nodded in the affirmative. Turning to her bosses, Gladys informed them, "We have a driver." George Carruthers, 56, founding and managing partner, of Farber, Underwood, Carruthers, Kinshaw, Young, Oswald, Updike, their city's first openly transgendered professional firm, John Woodworth, 39, an associate under Carruthers, and Mr. Carruthers' research staff manager, Howard Melrose, 48, were pie-eyed. George, whose en femme name is Gertrude, John, whose en femme name is Gwendolyn, and Howard, en femme Gladys, had attended New Year's Eve party wearing the same dress- unplanned. The dress was a simple black short-sleeve sheath, hitting each at the knees. Well, the dresses were not identical. Gert's had a square neckline, Gwen's a scoop neckline, and Gladys' a V-neckline. After all, when dressed as men, they would all wear the same pin-stripe suit and white shirts, only their ties showing any variety, and not much at that. As at most office parties, people from the same department tend to socialize with each other, often confounding one of the purposes of such parties-to have firm members mix outside their departments-and these three were no exceptions. By 11:30 pm., all three were in no shape to be operating a motor vehicle on the public roads and byways-or private ones either. Gladys spotted Zachary's Outopoulis-Zack the Greek-talking with a fellow researcher. Zack-Daphne when en femme-was not that hard to spot. At six one, she was taller than most of the firm's employees. In strappy sandals with four-inch spike heels she towered above everyone. Add to that she was wearing a red leather mini that barely covered her crotch, a matching bustier for a top, hooker make-up on an all too pretty face, several bracelets, gold necklace, and hoop earrings, plus her dirty blonde hair, normally worn in a ponytail, cascading to her shoulders. Since being hired eight months earlier as Zacharias, Daphne had made a cautious appearance, encouraged by her fellow employees, both female and trans, and the firm's out-of-the-closet ambiance and transgendered partners setting the example. More than one of her bosses and co-workers-women, men, trans and straights-had tried to get into her panties. She had turned all down, acquiring a reputation as a flirt and a tease, when in truth she was scared shitless. Just nineteen, she was new to the city and had not fully accepted her sexual orientation. The three stood and wobbled out of the offices to the elevator, followed by a confused and embarrassed Daphne. By the time they reached the parking garage, Gert was leaning heavily on Daphne. The other three managed to get her out of the elevator and sat her down on the bench by the attendant's station. Leaving Gwen with her, Gladys led Daphne to Gladys' car, a four-door Lexus bespeaking her wealth and position with the firm. Handing the keys to Daphne, she looked up at the towering figure. "I'm not really all that drunk, but better safe than dead." It took Daphne several minutes to adjust the seat to her tall frame. She didn't notice Gladys admiring her legs and clothing as she moved in the seat. When she pulled the car up to the elevator, it took all three of them to literally pour Gert into the back seat, with Gwen spilling in on top of them. Gladys rode shotgun, giving Daphne directions to Gert's home. Gladys was impressed with the ease with which Daphne handled the big car, while Daphne wondered if she would ever own a car that this. Halfway to Gert's, the silence of the drive was shattered by the stereo snoring of Gert and Gwen. At Gert's, it again took all three of them to get her to her door. Gladys had to fish the keys out of Gert's purse to open the door. They dragged her to the bedroom, where all four fell on the bed, Gert in a snoring sleep, the others in exhaustion. Gwen stood, fell against Daphne, giving her a sloppy kiss on the lips. Daphne immediately drew away from Gwen, and would have pushed her away further if the associate had not sprawled on the bed with her boss in deep slumber, their snoring resounding throughout the bedroom. "I think we should leave them here," Gladys smirked, looking at the sleeping beauties. To Daphne's quizzical look she added, "It would not be the first time they spent the night in the same bed." The duo left the couple, walking in silence to Gladys' car. The only words spoken in the drive to Gladys' condo were her directions. In the condo's parking garage, Gladys directed Daphne's to Gladys' parking space, then turned of the ignition and removed the keys. Turning to Daphne, Gladys studied the young transvestite's face and form. Daphne tried to stare out the windshield, but the concrete wall made it a mirror in which she watched Gladys watching her. "How do you plan on getting home?" The older trans asked. Daphne had not considered this. When ordered to drive, she drove. She had complete confidence in her boss. In fact, she was in awe of her. Gladys had not considered how Daphne would get home when she asked Daphne to drive, either. She had expected the teenager to drop Gert, then Gwen, than herself off, and have the use of the car for the night as a reward. But as she watched how Daphne handled the car, she realized that Daphne was Zack trying to be a girl, not Daphne coming out. She used the mirror effect to gauge her words on the youngster. "When Gwen kissed you, that's the first time you've been kissed by a man, wasn't it?" Daphne didn't answer, but her reflection revealed the consternation the question was causing her. Gladys would not relent. "Sweet nineteen and never been kissed! Ever been fucked?" Silence. "By a woman or a man?" More silence. "Sucked a cock?" Silence. "Had your cock sucked?" Silence. "Fucked an ass?" "Had your ass fucked?" "Jacked a man off?" "Had a man jack you off?" "A woman?" "Ohmigod! A virgin! How did you get to be nineteen and still be cherry?" Daphne remained silent, her hands at the ten/two positions on the wheel. Gladys leaned over and placed her hand on Daphne's thigh at the hem of the miniskirt. Short as the skirt was, this permitted Gladys' fingernails to touch Daphne's crotch, covered by her pantyhose and panties. "Daphne," Gladys was now using her supervisorial voice, "look at me..." The staffer forced herself to turn and look at her boss. "I asked you, how do you plan on getting home?" "I... I... don't know." Daphne stammered. Gladys' hand on her thigh, with her fingernails flicking his cock and balls through the thin nylon material did nothing to help her regain her composure. "Would you like me to call a cab?" Gladys asked, her hand now splayed across Daphne's panties. Daphne nodded her assent. "Then let's go to my condo," Gladys suggested. She didn't mention that she could call for a cab from the cell phone in her purse. Gladys got out of the car and headed for the elevator, followed by a confused and scared Daphne. The ride to Gladys' floor was made in silence, as was the walk from the elevator to her condo door. Daphne knew that Gladys was highly paid, but the condo was more than any home she had ever been in. The living room was larger than her entire studio apartment. Across the wide expanse of the room, with its thick carpeting, sofa, loveseat, several chairs, various types of tables was a dining area. In Daphne's parents' home, this would have been a separate room, but in the nearly wall-less condo, one room flowed into another. At one end of the living room was an area, which Gladys had converted into an at-home office. Desk, chairs, short file cabinet, yet fitting in with the living room decor. At the far end was a small kitchen area, little more than a breakfast bar. Evidently cooking was not one of Gladys' strong points. Gladys led Daphne to the breakfast bar, which had a wall phone. Only as they went through the dining area did Daphne see the entrance to the bedrooms. Gladys indicated that Daphne take a seat. Seated, she was face to face with a standing Gladys. "Gwen mussed your lipstick," Gladys said, taking a paper towel and gently wiping Daphne's face. The move brought her crotch against Daphne's knees. When Daphne tried to move, Gladys took the opportunity to step closer, parting Daphne's legs. Her miniskirt was now riding up, revealing her stuffed panties. Gladys moved closer, until her crotch was against Daphne's. This pinned Daphne between the bar and Gladys. Finished with her clean-up, Gladys continued, "I want you, Daphne." Not waiting for the clerk to respond, "I want to take your cherries. I want you to understand what it means to be a trannie. I want to make a woman out of you. I want to taste you and teach you how to taste cock. I wish your first kiss wasn't from a drunken CD, but what's done is done. Here's how it should have been." With that Gladys took Daphne's head in her hands and kissed her, taking the younger trannie's upper lip between hers, sucking gently. She released Daphne's lip and repeated the procedure with the lower lip. She then moved one hand to Daphne's jaw, gently pulling it down. As Daphne opened her mouth, Gladys plastered her lips to Daphne's and ran her tongue throughout her mouth. Daphne did not know what to do. She had anticipated one day being in this position with a man, but not with a trannie- especially her boss. Despite what Gladys had said, Daphne was afraid that she would not have a job Monday if she resisted. And while she wasn't attracted to Gladys, the woman did know how to kiss! She would have to lose her virginities some day to some one. Gladys was willing to teach her how to be a woman, and from the last six months, Daphne knew she had much to learn. In fact, she had to be told who at Farber, Underwood, Carruthers, were real women and who were trans, so successful were most of the transgendered. Daphne wanted to be that successful, not realizing that she already was. She felt a breeze on her face and realized that Gladys was no longer kissing her but breathing softly across her lips. She next realized that Gladys' hands were no longer on her face. One was firmly pressed against her waist, the other being inserted under her pantyhose and panties. Gladys pressed upward with the hand on Daphne's waist, causing her to rise from the seat. Deftly, Gladys pulled the young staffer's lingerie down to mid-thigh. She fondled her penis and testicles, disappointed that Daphne remained flaccid. Lack of interest? Lack of desire? Impotence? Whatever, Gladys had taken another of Daphne's cherries: she was the first man to handle the family jewels. Gladys dropped to her knees and pulled the pantyhose and panties down to Daphne's ankles. She looped her forefinger and thumb around the limp cock and swallowed it whole. Another cherry: the first male mouth on Daphne's dick. Gladys swirled her tongue around the penis, sucked on the head, jacked it and licked it. It remained a curled snail. Gladys was now getting pissed. While seduction was not her forte, she had developed a certain skill in sexual arousal and Daphne's lack of arousal had become an affront. Affronting her boss was the last thing Daphne wanted to do, even if she was aware she was doing it. And she was not. She was aware of what was happening to her, more as an out- of-body experience, not as a sexual experience. She had had her dick fondled only by women before-girls really-in high school. These had always resulted in quick ejaculations earning her a reputation for being quick on the trigger. This had given her a certain popularity since girls knew a quick hand job was as far as they had to go with him sexually. It had also led to his still being a virgin. Only Robbie-Roberta-the real girl who was his fellow researcher and mentor at Farber, Underwood, Carruthers-had handled his penis since then. She had also given him his first blowjob, with the same results Gladys was obtaining. It was Robbie who suggested that maybe women did not appeal to him, and that he should explore the transgendered world his employment at Farber, Underwood, Carruthers made possible. The transition had been fun, and Daphne had no problem getting hard and wanking off in private, often to images of Robbie, while wearing stockings, panties, corsets and bras. But with her, or in public, Daphne never had an erection, which was great considering her penchant for miniskirts and lacy panties. She knew she would never get hard, no matter what her boss did, and wondered how Gladys would take this. Gladys had adjusted her attitude. What she wanted most was to fuck this sweet young thing. She most certainly didn't want to rape Daphne, as she had been raped a quarter century earlier while en femme. She wanted Daphne to enjoy being fucked as a woman. But seduction is a dance; the seducer and the seduced must each co-operate with the other. While Daphne was not resisting, she was also not responding. Oh well, lying on your back and thinking of America is also being fucked like a woman. Standing abruptly, Gladys turned her back to Daphne. "Unzip me," she ordered. Daphne immediately complied. Gladys turned partly and looked at Daphne from head to toe. Only the smeared lipstick around her mouth detracted from her beauty. The miniskirt had dropped enough to cover her manhood. The bunched hosiery was the only discordant item. "Remove those and come with me." Gladys ordered. Without waiting for a reply, she headed for the bedroom. Daphne bent over and unfastened her sandals before removing the pantyhose and panties. By the time she straightened up, Gladys had disappeared. Daphne followed in her wake. When Daphne entered the bedroom, Gladys was hanging up her dress on the back of the closet door. She was wearing a long-line bra that met her pantyhose. She sat on the bed and removed her pantyhose, then patted the bed next to her. Daphne sat next to her and slipped off the miniskirt. "Leave that on," commanded her boss when she started to unfasten the bustier. Standing, Daphne saw that Gladys wore full-cut control panties with padded buttocks and hips. Daphne had wondered how her boss, or most of the other transgendered staff, achieved such womanly hips. She had always been self- conscious of her own boyish shape, although it seemed to turn on others. Gladys squirmed out of the panties to reveal a thong-like panty, which held her male parts between her legs. The look on Daphne's face amused Gladys. "It's called a gaff, honey.... You should wear one the way you dress. I guess Ms. Orlovnova doesn't know everything about dressing like a woman." Gladys smiled to herself at her last comment. Roberta Orlovnova may know how to dress as a woman, but she didn't know how to dress like a woman. Gladys liked Roberta Orlovnova, the staffer Daphne was talking with when Gladys summoned her. Roberta was a good researcher, thorough and efficient. A straight woman, she had come to Farber, Underwood, Carruthers fully aware of its transgendered status-the only transgendered professional firm in the city, indeed in the state-and never had a problem with its crossdressing partners, associates or other staff. When Zack arrived, Gladys thought she saw a budding romance between two straights in the office. So it was with surprise when Zack began transitioning into Daphne, obviously with the assistance of Roberta. It became obvious that Daphne was Robbie's new best friend, and Robbie protected her like a kid sister. Roberta's willingness to do battle even with partners to protect Daphne had led many to question the sexual orientation of both, as well as their relationship. For the first time, Gladys wondered what Robbie was thinking when she called Daphne over at the party, and the young researcher left with the three old broads. Gladys removed her gaff, revealing a decent seven-inch cock, which immediately sprang forward. "You still got time to call that cab, Daphne," Gladys said, reading the look of apprehension on Daphne's face. "The phone's on the night stand." Gladys then went into the bathroom, where Daphne could hear her relieving herself. Gladys had not planned on drinking so much or ending up the last one home. One of the downsides of being a CD is all the clothing one has to remove to take a simple piss. She removed her bra, grabbed two beach towels and headed for the bedroom, hoping Daphne would still be there, the phone unused. She was; it wasn't. Daphne still had that deer-in-the-headlights look. Gladys briefly thought about calling that cab herself. Very briefly. While fucking the staff was something she seldom did, and then usually when that staffer pursued her, she wanted Daphne. Bad. Very bad. "Stand up, honey," she said. Daphne stood. In her bare feet she was slightly taller than Gladys. Gladys pulled back the bedclothes, then covered the sheets with one of the beach towels. The other she folded in half, breadthwise, then in half again. This she placed across the first towel. Turning to Daphne, she indicated the researcher should get on the bed. Turning to her nightstand, she opened the top drawer and removed a packet of condoms and several tubes of lubricant. She placed one of the condoms on herself, lubed it and turned back to the bed. Daphne was on her hands and knees, facing the headboard. "No, honey," Gladys smiled. "On your back, with your ass on the top towel." Daphne laid down as instructed, her confusion registered on her face. Gladys climbed on the bed, positioning herself at Daphne's ass. She raised Daphne's legs, placing a calf on each shoulder. "I'm going to make a woman out of you," Gladys informed her, squeezing a tube of lube onto her fingers. "That means being fucked like a woman, on your back with your legs spread." Gladys inserted a finger, then two in Daphne's ass, spreading the lubricant into her anus. She then insert the nozzle of another tube into Daphne's ass and squeezed it all in, watching it bubble at the entrance. She then placed her cock at the entrance and spread the contents of another tube over the head and at the entrance. "This is going to be messy," she said, more to herself than to Daphne. Gladys lowered her legs, then pushed the knees toward her head, and outward. Looking at Daphne's apprehensive face, Gladys tried to soothe her. "I'll be as gentle as I can, honey. But it's gonna hurt a little. I can't help that, but I'll be as easy on you as I can." With that, Gladys pushed forward. Daphne's ass yielded until Gladys reached her sphincter. Gladys lay on top of Daphne, pulled back and rammed herself through. Daphne had been trying not to cry out, although it hurt like hell. When Gladys forced her sphincter, the pain was too much. She let out a loud shout, and grabbed Gladys' shoulders. Gladys began pumping furiously, knowing from her own experience that the pain could not be lessened, but could turn to pleasure. But not this time. Gladys' initial thrusts caused sharp pain, which turned into a dull ache by the time Gladys collapsed on top of Daphne, spent. Daphne never felt Gladys cumming, nor the twitching of her cock as she filled the rubber with several spurts. Daphne was barely aware of the weight of Gladys' body, or the shrinking of her dick. Only when Gladys pulled out and rolled over on her back did Daphne realize that the ordeal was over. As she regained her breath, Gladys noticed the smells of their lovemaking permeating the room. Looking down her body she saw the source of smell-her condom-clothed cock covered with lubricant and feces. She didn't have to look at Daphne to know that the same mess oozed from her ass onto the beach towels. From Daphne's whimpering, Gladys knew she had hurt the teenager, even though she had tried not to. Recovered, Gladys got up and went to the bathroom. She removed the rubber and flushed it. She started a bath running, adding bath oil in her favorite scent-lilac. As the tub began to fill, she took a washcloth and cleaned herself, becoming aroused again. Damn! There was no way Daphne would be able to satisfy her a second time tonight without being totally traumatized. Returning to the bedroom her eyes were drawn to Daphne's splayed legs. Slightly drawn up, the evidence of her defloration smeared her buttocks and the towels. She still lay on her back, the cups of the bustier pointing to the ceiling. If it wasn't for the shriveled dick where a pussy should be, Gladys would have thought she was a girl. Walking over to the bed, she took the researcher's arm and pulled her up. Daphne stood, wobbled, and had to lean on her boss for balance. Gladys unfastened the bustier, letting it drop to the floor. She then guided Daphne into the bathroom and helped her into the bath. Like the rest of the condo, the bathroom was huge. The bathtub itself was really a sunken spa, large enough to hold three or four people. Oval, there were showerheads at each end of the oval, with the faucet on one side. Steps led from the floor to the edge, which was about a foot above the floor and about eighteen inches wide, and more steps led down into the spa, which was a foot deep at the steps and three feet deep at the far end. The spa filled from the deep end. Even with the water turned on full, the bath was barely half full when Daphne entered. She settled down gingerly, the hot water turning the throbbing in her ass into a sharp pain before it became a dull throb again. Gladys turned the water off, noticing it was just deep enough for Daphne to have a good soak without danger of drowning. She left the young trannie to luxuriate. Returning to the bedroom, Gladys assessed the damage. The beach towels were soiled beyond description, as she had anticipated. She removed them and took them to the laundry room. My'esha would not be pleased when she picked up the laundry, but it would not be the first time she had to clean these towels. Besides, she charged enough. Back in the bedroom, Gladys was pleased that the sheets remained unsoiled. Normally, she wouldn't have worried, but this was the first virgin she had had, and she wasn't expecting as much of a discharge as Daphne made. She picked up the bustier, surprised that the cups still held their shape. On closer inspection she noticed the cups were filled. She fastened the bustier and stood it on its bottom. It stood up as if on a mannequin. She picked out a nightgown for herself, an ankle-length silk with kimono neck. She debated whether to lie out a similar gown for Daphne, or a baby doll outfit, or nothing. She settled on a plain silk slip, thinking one of her full silk slips would be a suitable nightgown. Satisfied, she went to join Daphne in the spa. Daphne had taken to the spa like the proverbial duck to water. After the initial sting of her asshole, she had sat down and noticed the silky smoothness of the water. Spying Gladys' assortment of bath salts and oils, she had experimented, relying first on the colors of the contents of the various jars. As the water cooled, she added more hot water, more bubbling salts, more oils. Gladys quickly assessed the situation when she re-entered, bemused. Daphne was not aware of Gladys until the manager stepped into the spa. Her added bulk caused the water to fill two-thirds of the spa. Daphne quickly sat up. Gladys said nothing, just sinking until the water was up to her neck. She turned on the hot water, and made an adjustment to the drains so that the water level remained the same. The two enjoyed the spa for more than a quarter of an hour in silence. "Feeling better?" Gladys asked, breaking the silence. Daphne merely nodded. "I'm sorry it hurt so much. I tried to be gentle." "I know, Mrs. Melrose," the staffer said. It was the first time she had addressed her boss. Gladys was somewhat amused at the formality of the address. Since she always went to work en femme, she was known as Mrs. Melrose. While Gladys was pondering this, Daphne continued. "I'd been told that it was going to hurt, but I didn't think it would be that bad. Will it always be like that?" "I can't say, Daphne," Gladys answered. "Who have you been discussing this with?" "Some of the other... uh... uh... women... at the firm," Daphne stammered. "Did you want this to happen?" "Well, Mrs. Melrose," Daphne replied hesitantly, "it had to happen sometime, didn't it?" "Not necessarily. Lots of crossdressers are straight, including quite a number of the ones at the firm. You can be a trannie without being gay." "Oh," was all Daphne said, looking at the water in front of her pensively. "Do you think you're gay, Daphne?" "Well... yeah..." "Why?" "Well... I could never... you know.... get... you know... with a girl." "You mean get an erection?" Daphne slowly nodded her head. "Well, you didn't get one with me, either." Daphne didn't say anything, but Gladys surmised what she was thinking. "You're thinking that's because I'm such an old bag, right?" Again Daphne stared at the water. "Have you ever had an erection?" "Uh... yeah." "Well?" Gladys wanted details, and details Daphne did not want to give. "Do you get an erection when you masturbate?" "Uh... yeah." "When you masturbate, do you fantasize?" "Yes." Progress! Gladys could not believe this was the same staffer who could give a ten-minute extemporaneous presentation. "Do you fantasize about men or women?" "Hm... women." "Do you cum when you fantasize about women?" "Sometimes." "Do you ever fantasize about Roberta?" "Roberta?" "Yes!" Gladys nearly shouted in exasperation. "You mean Robbie... at work?" "Yes, Daphne, I mean Roberta Orlovnova, senior research assistant, Faber, Underwood, Carruthers, Kinshaw, Young, Oswald, Updike. Robbie, if you prefer. Five five, dark brown hair, wears it in cute pixie cut, mid-twenties. Nice set of knockers, cute ass, nice legs. Imminently fuckable. Do you jack off fantasizing about her?" "Uh... yes, Mrs. Melrose." Daphne was extremely uncomfortable with this line of questioning, despite the fact that she was sitting naked in the spa with Gladys, that Gladys had just fucked her in the ass, had sucked her dick, had kissed her. It was bad enough to discuss her own sexual activities-or rather inactivity. But to talk about Robbie that way! Daphne didn't even think Gladys thought of Robbie that way. "And do you cum?" Gladys hoped she didn't have to explain further. "Yes, Mrs. Melrose." Daphne was more resolute now. She wasn't going to let Gladys bad-mouth Robbie, even if she was boss of both of them. "Daphne," Gladys intoned gently, "or maybe I should call you Zack. You're not gay." "What!" The pronouncement shocked her. "You are not gay." Gladys repeated herself. "Just because you can't get it up when you're on a date doesn't make you gay. If it did, 99% of all men would be wearing panties." Gladys chortled at her last remark. Daphne began studying the water again. She had to be gay! She had never had an erection with a woman. She had never had sex with a woman. She enjoyed dressing as a woman. At least when she did it with Robbie and they went out as girls. And she had let a man kiss her, and suck her prick, and fuck her ass, and now she was in a giant bathtub with that naked man, who, although she still had traces of make- up on her feminized face, and still had her hair in a French curl, was also sporting a decent erection which poked up through the water like a periscope. She just had to be gay! For the first time that evening Gladys was faced with a moral dilemma. Zack had become Daphne only because he thought he was gay. Daphne had let Gladys fuck her because she thought that is what gays do. Gladys had fucked Daphne because she thought Daphne was at least bisexual, if not gay, and wanted to be part of the transgendered life. She now realized that Daphne was not gay, just confused. Yet she still wanted her. She still wanted to suck her cock, to fuck her ass again, to teach her how to suck cock-her cock! Should she take advantage of Daphne's confusion and use Daphne's body for her own pleasure? Should she guide Daphne back to being Zack? Should she help Daphne/Zack explore the transgendered world of being both a man and a woman?