David carefully applied superglue to the elastic net inside the wig, then slipped the hairpiece over the shiny smoothness of his bald head, taking pains to insure that he left no glue traces in visible spots on his cheeks or temples. He adjusted the wig carefully, checking its placement in the vanity mirror, and held down the net for a half minute or so to allow the adhesive to dry completely.
His cigarette was still smoldering in the ashtray on the vanity table and he took a puff from it as he studied the results of his makeover so far.
The face that stared back at him from the mirror was unquestionably that of his older sister, Jenny. It was Jenny without makeup or eyebrows, but Jenny all the same. The wig he had just glued securely in place was even a dead match for Jenny’s shoulder-length blond curls.
It was a good face. Jenny was 46 years old, 22 years older than David, but she prided herself on her appearance, used her expensive cosmetics carefully and to good effect, and always dressed in simple but flatteringly fashionable clothing. Unlike some businesswomen who dressed in dull suits in an attempt to blend into the background, Jenny sported a sexy style that belied the fact that she was only nine years away from early retirement.
David smiled at his reflection and his prosthetically enhanced lips gave him a remarkably good counterfeit of Jenny’s carefree grin. It felt strange as the latex and foam features aped his sister’s expression. Even small movements of the prosthetic lips and nostrils required conscious effort. He would have to exaggerate his facial gestures all night in order to insure that they exactly matched those of his sister through the heavy disguise.
His entire head, you see, had been turned into a lifelike rubber mask in order for him to achieve a believable impersonation. The top, sides and back of his head were covered with latex Woochie wig that neatly concealed his own hair under an artificial bald pate. The wig had been glued on with spirit gum, then varnished into place with multiple layers of liquid latex in a neutral Caucasian skin tone. The shape of his brow and forehead had been changed with a prosthetic foam appliance that was also sealed into place with numerous coatings of liquid latex, each carefully dried in place with a hand hair blower.
A false nose that was molded from a life cast of his sister’s face had been cemented into place over his own, as had a two piece latex mouth and chin. Foam and latex pads had been used to give him the high cheekbones and middle-aged jowls of his sister’s face. The entire visage had been carefully sealed under liquid latex painted on coat after coat with fine bristled brushes. The result was a smooth and seamless rubber skin that concealed his entire head from the neck up.
The disguise was extremely convincing, but that was not surprising. David, after all, was a theatrical makeup artist who had been working in the city’s largest theatrical company since his college days. He had been hired to do cosmetic special effects for several independent films and a horror movie that had been a box office smash.
He was a perfectionist, and even with his skills and experience, it had taken nearly three hours for him to replicate his sister’s features, piece by piece, layer by layer.
He stubbed out his cigarette, exhaling thin streams of smoke through the mask’s nostrils, then peeled two thin strips of latex with rooted hair from a small glass sheet and cemented them into place over his eyes, perfect replicas of Jenny’s eyebrows with their characteristic arch. With the brows securely fastened, he used a special latex grease paint and other cosmetics – eyeliner, shadow, mascara, false lashes, blush, lip liner and lipstick — to finish copying Jenny’s face. The finished face that ultimately looked out of his makeup mirror was an extraordinary match for that of his sister. Even their long-dead mother would have believed he was Jenny – at least until she had time to study his face carefully. It was hard to believe that underneath the attractive features of a mature woman actually was the face of a 24-year-old man. David was certain that anyone less intimately familiar with his sister would be completely fooled by the disguise – even her new boyfriend, Robert.
Particularly Robert; tonight, that would be imperative.
Jenny was David’s only living relative, as well as being his best friend. David’s father had died when his commercial air shuttle crashed during a business trip about four months before David was born. His birth was an extremely difficult one that required surgery, and his mother never fully recovered from it, dying shortly after he was a year old.
David’s father, a successful business executive, had a sizeable stock portfolio and considerable insurance coverage, and his mother’s will left the entire fortune to Jenny and David. Since she was an adult and had already launched a career in data processing, Jenny had herself named David’s guardian. She cared for him full time until he was six and started school, afterward using nannies and other child care givers to look after him while she was at work or out of town on business.
David, who was bookish and quiet, adored his sister and admired her inordinately. He emulated her in every way while growing up, and their sibling relationship was more like that between two sisters – one older and one younger – than like that of a brother and sister.
When David reached puberty, he developed a fascination with Jenny’s lingerie and clothing.
When she was away at work or on business trips, he would slip into her room to go through her dressers, stroking her soft panties against his face and groin, enjoying the traces of her perfume he could smell in her dainty underthings. He began trying on her clothing secretly when he was 12, and quickly became quite expert at disguising himself as a woman. He would put on her lingerie, hose, high-heeled shoes, dresses and makeup while she was gone, combing out his own long straight hair into a softly curled feminine fashion that vaguely resembled Jenny’s. Thus attired, he would sit around the apartment they shared, listening to Jenny’s jazz records and smoking her long filter-tipped cigarettes to make himself feel older and more sophisticated.
He continued his secret masquerade until he was 15 years old. Then one night Jenny returned home unexpectedly from what was supposed to be a three-day trip to the Coast. She opened the apartment door to find him sitting on the coach in full make up, brassiere, panties, nylons, heels, and her black satin sheath cocktail dress, his hair brushed sleekly back and clipped into a loose, feminine pony tail.
Jenny didn’t say a word – she later admitted to him she had been struck dumb at the sight – but David, hideously embarrassed, ran to his room and threw himself on his bed, crying in huge wracking sobs. Jenny slipped in silently a few seconds later and sat down gently beside him, petting his bare back and shoulders and murmuring that it was all right – that she didn’t care if he wanted to wear her clothes.
They talked all that night, and David sobbingly confessed that he had felt himself to be more female than male from the time he began puberty. He admitted his conviction that he had been born the wrong sex, and that he daydreamed about having sex with other boys and even derived sexual satisfaction from masturbating while dressed as a girl. He also told her his activities made him feel guilty and he knew that his feelings weren’t normal.
“Oh, Jenny,” he wailed, “What am I going to do?”
Jenny told him there was nothing wrong with him.
“Darling, not everyone grows up the same when it comes to sex,” she said with a gentle smile, stroking his long hair with her fingertips and kissing his forehead tenderly. “Some men were simply born to be women, and it may be that you are one of them. Lots of men cross-dress, but otherwise have normal sexual relations with women. Some men who enjoy dressing as women are gay. It isn’t something that is common but it happens.
“We don’t know which group you fall into, but it isn’t all that important, anyway. You are what you are, and you can’t help it. There’s nothing to be ashamed of.
“I love you, anyway, whether you are a boy or a girl,” she concluded, giving him another gentle kiss on his cheek.
That night, David fell asleep with his head in his sister’s lap, her fingers coiled in his long, straight hair.
Jenny took David’s sexual confusion very seriously, but saw no reason to panic. She had her brother evaluated by a female psychiatrist she knew from her college days. After a thorough physical, a battery of written attitudinal tests and hours of interviews, the shrink diagnosed David as a gender dysphoria sufferer. The doctor told Jenny that David should be allowed to adopt the gender identity he found most comfortable, adding that, should he choose to live as a female, there was always the option for surgical gender reassignment.
For her part, Jenny gave David the room and freedom to find his own path. Far from expressing concern or dismay about his female impersonations, she praised his appearance and helped him learn the finer points of feminine deportment and body mechanics. She tutored him on fashion and was always willing to offer constructive commentary about his appearance and demeanor.
As time went on, David became ever more like Jenny’s sister than her brother, and the two spent considerable time together as two women, shopping, going to shows and museums, and enjoying heart-to-heart talks during long walks in the city’s large central park. Jenny was loving and non-judgmental, and David’s admiration for her became even stronger as a result of her supportive attitude and actions.
As it turned out, gender surgery never became a serious consideration. In his late teens, David continued to dress as a girl part of the time, but after his first successful flirtations with boys in high school and college, he decided he was gay and not transgendered. His desire to become a woman gradually faded, and his cross-dressing activity was eventually subsumed into his growing interest in the dramatic arts. He won rave notices playing female parts in several high school Shakespearean presentations and channeled his skill with cosmetics and disguise into a more general interest in theatrical makeup and stagecraft.
It was his theatrical work that had first inspired him to impersonate his older sister. David had “played” Jenny on three different occasions, each time at her specific request. Twice he had accompanied her to costume parties as her “twin sister.” Once about a year ago he had attended an important cocktail reception at her computer company, acting as her proxy when a sudden bout of the flu made it impossible for Jenny to attend.
His sister had been particularly grateful for that escapade, since David – as Jenny – had been so charming and convincing to a major client that it had helped Jenny win a multi-million dollar system installation contract.
Jenny had persuaded her brother to engage in the high-stakes masquerade by assuring him that the soiree would be strictly social, with business discussions strictly forbidden.
Nevertheless, “Jenny” found himself next to the client, Dana Harwith, in the lady’s room while refreshing his lipstick, and Dana confided to “Jenny” that her presentation of the firm’s proposal at an earlier business conference had given her the inside track on the project.
“There aren’t too many of us older women in major decision making positions in this industry,” Dana had said with a smile while squeezing David’s arm softly in what seemed to be a lesbian pass. “We girls have to stick together, honey.”
After the party, David, still wearing his “Jenny” costume – a black sleeveless cocktail dress and four inch heels – sat on Jenny’s sickbed, recounting the evening as precisely as he could.
“Honestly, sis,” he said, still mimicking Jenny’s breathy contralto perfectly, “She was really coming on to me. I thought she was going to put her hand up my dress right there in the bathroom. Now that would have given her a surprise!”
Jenny gave her brother a broad smile. “Dana has issued a standing invitation for me to join her for drinks and dinner,” she told David with amusement. “She is always putting her hand on my thigh, bumping her hip against me or locking her arm in mine when we meet. She has made it extremely clear that she wants to get into my panties – and I don’t mean just to try them on, either. I may just take her up on her offer. After all, she is a very attractive woman – and she would probably be a lot of fun in bed.”
Jenny touched her brother’s prosthetically altered cheek gently. “Or maybe I should just send you in my place,” she added with a grin. “You could report back to me on how she was.”
David laughed at the thought. “She’s more your type than mine, sister dear,” he said. “She doesn’t have the kind of plumbing I like in a bed partner.”
Jenny patted David’s thigh, looking at him with wonder. “You do a very good impersonation of me, brother dear,” she said thoughtfully. “Sometimes it makes me a little nervous, how exactly you have me down.”
David smiled at the recollection and lit another cigarette, noting that he still had to finish getting ready. Fortunately, he had two hours to complete dressing, far more than enough time. As he smoked, he thought to himself, You are right to be nervous, dear sister. If you knew what I was up to tonight, you would be downright frightened.
David rose and moved to the bed. Copying Jenny’s face, voice and mannerisms was one thing. Replicating her body was quite another.
In the past, he had simply worn a waist cincher, a long-line bra with good quality breast forms and a padded girdle to simulate her womanly figure. Under a dress, pantyhose and a slip, the pads worked just fine. However, tonight he needed a physical makeover that would stand up to a much more intense scrutiny. He had put together some items that he hoped would do the trick without the possibility of detection.
The first was a latex long-legged panty girdle that he had molded himself from a plaster casting of his lower body while he was trussed up in a gaff and a waist-cinching corset. He had used the casting to make a plastic mannequin of his lower torso, then sculpted the model with fine quality clay to eliminate the lines and texture of the corset he had been wearing and increase the size of the hips and buttocks. Finally, he had sculpted in a variety of realistic details, including replicas of Jenny’s appendectomy scar, dimpled belly button and vagina.
The resulting positive body model had been cast in more plaster and David had used the negative casting to mold the rubber panty girdle. The outside “skin” of the garment was made of relatively lifelike latex, and the inside consisted of more durable and somewhat stiffer silicone rubber to help the girdle hold its shape when worn.
David spread a little talcum powder on his lower body and picked the garment up. He stepped into the legs and began slowing working the very snug rubber girdle up over his thighs and hips, taking care to make sure that its female features were positioned properly on his male torso. Because the corset he had worn when making his castings for the garment was very tight, he could only slide it into place with some difficulty, alternatively holding his breath and expelling as much air as possible from his lungs.
It took nearly ten minutes to get into the rubber girdle. When he was done, he studied the results in the full-length mirror on the wall. The torso had as dramatic an effect as the prosthetic mask had. Turning to the side, David admired the slight folds of “flesh” under the garment’s buttocks. The appendectomy scar looked exactly like Jenny’s and the only difference between the female sex between his legs and that of his sister was the torso completely lacked Jenny’s dark blond pubic hair.
David moistened a finger and slipped it between the torso’s rubber vulvae. The interior of the torso had a rather thick latex pocket that effectively concealed his male genitalia, but was roomy enough to allow him to insert a six-inch phallus into the girdle’s cavity. The artificial vagina was not precisely the same as that of a woman, but he hoped that it would be sufficiently realistic to make David’s masquerade successful. He enjoyed the pressure of his digit on his latex-covered member, and massaged himself for a few moments before using liquid latex and fine bristled paintbrushes to “erase” the girdle’s seams on his upper abdomen and thighs.
Breasts were a simple matter. David had molded a pair of realistic latex shells that contained high-quality silicone breast forms. He used surgical adhesive to fix the rubber bosoms over his own cleanly shaven chest, then “erased” the small seams with more liquid latex, curing the rubber coating with a hand-held hair dryer.
When he was finished, he posed in front of the mirror, enjoying the soft femininity of his new woman’s body – a body that was virtually indistinguishable from that of his older sister.
With his face and body done, David donned a black satin garter belt and soft bra, smoothed smoke-colored stockings up his smoothly shaven legs and clipped them to the garters. He pulled a sleeveless Spandex aubergine cocktail sheath over his head and smoothed it down over his shapely curves, then stepped into a pair of matching purple pumps with four-inch heels.
He had already trimmed and filed a set of press-on fingernails and painted them with four coats of deep eggplant purple polish to match his shoes and dress. It took him less than ten minutes to attach the plastic tips carefully to his fingertips with superglue, and he buffed the finished nails carefully with a soft cloth to bring up the sheen of the polish.
He had “borrowed” several items of personal jewelry from Jenny’s chest of drawers. He put them on now: a string of pearls that reached almost to the cleavage of his latex breasts, the oversize onyx and silver ring Robert had given Jenny on their second date, a small gold Seiko watch Jenny wore for evenings out and a pair of gold rings she wore on her right hand.
When he was finished, the illusion that looked back at him was a perfect counterfeit of his sister. He gave himself a little squirt of Caleche and rubbed a drop of the heavy perfume on the underside of his wrists. Lighting another cigarette, he picked up a small, sequined black purse, put his cigarettes and lighter into them, and moved into the living room area of the apartment he shared with Jenny to wait for Robert’s arrival.
Sitting on the sofa, legs crossed elegantly at the knee, he smoked silently, thinking back to the first time he had met Robert.
Jenny had come home from work in a rush, saying only that she had a remarkably attractive man at her office and was going to dinner with him that night. David, who was busy reviewing the script for an action film for which he was supposed to create special effects makeup, had murmured noncommittally without really looking up. About an hour later, when Jenny emerged from her bedroom wearing one of her sexiest outfits and a very formal makeup look, he had realized that her date was someone she considered very special.
“Wow!” he said, silently mimicking a wolf’s whistle with his lips. “This looks like it is going to be some dinner, sister dear.”
Jenny blushed slightly. “Well, we aren’t going down for Big Macs and fries, kid brother,” she said, checking the time. “I wasn’t sure I was going to have time to get ready for this. It was really a spur of the moment thing.”
David smiled as his sister’s apparent nervousness. “Who is this lucky fellow?” he asked.
Lighting a cigarette, Jenny blew a lungful of smoke at the ceiling. “He’s a new client from back east,” she said. “He is so gorgeous that he could be a male model. I feel like a cradle robber, though: he is just about half my age.”
“Well, he must be really something, considering the way you are dressed,” David grinned. “I haven’t ever seen you get dolled up for a date that fast. And I notice you are wearing the Caleche, tonight. That is your favorite perfume, but you only wear it for special occasions.”
The bell rang and Jenny nervously primped in the mirror over the fireplace. “Let him in while I check myself over, would you?” she said. “You can give me your assessment when I get back from dinner.”
David, still grinning, rose and padded to the door. When he opened it, he was momentarily struck speechless.
Robert was around David’s height and had a trim, well-proportioned body, although some critics might have said his bottom was a little big. His hair was medium in length and a darker shade of blond than Jenny’s, worn parted on the right hand side with bangs that swept just over his left eyebrow. The eyes under those slightly bushy brows were a startling ice blue. Roberts lashes were long and curly and he had a narrow nose with a slight upward tilt at the tip. He smiled at David, showing small and even white teeth. David’s heart melted in an instant.
“Hello,” he said. “I’m Robert Anders, here to pick up Jenny Childress for dinner. I hope I have the right apartment…”
David stammered. “C-come in,” he said, stepping back and holding the door wide. “I’m David, Jenny’s brother. She just finished getting ready.”
Jenny, smiling, crossed the room and gave Robert a little peck on the cheek. “I see you found my place without too much difficulty,” she said as he took her hands in his own. “I just finished getting myself together. Where are you taking me?”
Looking her up and down with obvious appreciation, Robert flashed a glimpse of those incredibly even teeth. “I asked the concierge at my hotel what the best restaurant in town was, and she said we should go to a place named ‘Blue Light’ down near the yacht basin. I took the liberty of booking a table for two at 7 p.m. Does that sound okay to you?”
“Well, I don’t know,” she said with a mischievous grin. “It is only supposed to be the best — and most expensive. I suppose it will have to do!”
Turning to leave, Robert extended his hand. His grip is warm and firm, and his skin is very soft, David noted to himself.
“Nice to meet you David,” Robert said as he and Jenny stepped through the door. “I am completely taken by your sister, so I’m hoping I will get to see you a lot more of you in the future.”
Me too, sugar, David thought as his sister and her date left the apartment. And I hope to see a LOT more of you!
Taking a deep puff off his cigarette, David – now Jenny – blew a lazy stream of smoke at the ceiling. He had seen more of Robert – but only when the blond man came to visit Jenny or pick her up for an evening on the town. He had never had the pleasure of more than a handshake from his sister’s new boyfriend, even though his sexual fantasies about Robert had run riot.
If everything goes right, tonight that may change, David thought to himself, smiling Jenny’s cat-like grin. Let’s hope everything goes right!
As David put out his cigarette, the doorbell rang. He glanced at his watch in surprise: Robert was more than a half-hour early! He stood up, smoothed his sleek purple dress and answered the buzzer.
Robert was waiting outside in a dark blue suit, a pinstriped shirt and perfectly knotted navy blue necktie. He smiled as “Jenny” opened the door and stepped into her apartment. Jenny stepped forward with an expectant smile and Robert put his arms gently around her and kissed on the lips.
“How’s my beautiful fiancée tonight?” he asked, kissing her forehead tenderly. “I’m sorry I am early, but I just couldn’t bear to kill another 30 minutes waiting to see you again. Have you been ready long?”
“Only all my life, darling,” Jenny said with a grin. “How was the trip out?”
His arm still around her waist, Robert led her in to the sofa and sat down, pulling her down beside him, “Tolerable,” he said, punctuating the statement with another kiss. “Coach class was terrible, but seeing you again makes it all right.”
Jenny sighed and touched his cheek in a soft caress. Under the latex girdle, David’s penis strained with desire inside against its tight rubber prison. So far, Robert seemed to be totally unaware of the masquerade. David’s worst fear was that his disguise would be immediately transparent, and the evening would be over before it began.
Robert bent for another, longer kiss, placing his hand in Jenny’s crotch and stroking it gently. Jenny moaned almost inaudibly with desire.
With a final kiss, Robert stood and pulled her to her feet. “Time enough to get cozy later,” he said with a grin. “Let’s go get some dinner. The food on the airline was so bad, I didn’t even bother with lunch. I am ravenous!”
Jenny smiled back. “Let me get my jacket and we will go.” As David slipped on his sister’s evening coat, he keyed the answering machine so that the message he had recorded – as Jenny – explaining that she had unexpectedly been called out of town on business would answer on the second ring and play silently for any callers that night.
The evening went exactly according to plan. Robert treated Jenny to a wonderful dinner of Petrale sole at an elegant seafood restaurant they had patronized before, and they made lovers’ small talk over the dinner and a bottle of good Chardonnay. Afterward, they enjoyed cocktails and dancing at a four-star hotel in midtown, moving together to the romantic sounds of the hotel’s house trio.
Robert used the slow numbers to nuzzle Jenny’s throat passionately and gently place his hands in just the right places on her hips and back. Jenny sighed with pleasure. How I wish I could be Jenny, instead of just being her double, David thought to himself as the night went on.
Finally, the couple finished their last drinks and went back to Jenny’s apartment for a nightcap.
Jenny poured out two snifters of cognac in the kitchen. She brought Robert his drink and sat beside him demurely on the sofa, taking a sip of her brandy and then leaning forward to brush her lips against those of her fiancée.
Robert returned her kiss with passion, slipping his hand behind her to unzip the back of her dress. Breathing hard, Jenny loosened and removed his tie and unbuttoned his shirt, placing her hands on his smooth, hairless chest. For a moment, both struggled with their clothing, stopping only to exchange kisses. When Robert dropped his pants, Jenny almost gasped at the sight of his fully erect penis. They clutched urgently and within moments, Robert was inside her artificial sex, pumping slowly and steadily. The pressure on David’s trapped penis was extraordinarily wonderful, and after only a few minutes, he came with a quiet moan inside his rubber girdle.
They lay together for what seemed like an eternity with Robert – still incredibly firm – tucked inside Jenny’s latex vagina. Finally, she sighed and smiled, excusing herself. “I think I need to fix my face,” she said in a husky whisper.
“Don’t mind me,” Robert said with a satisfied grin, sipping his brandy. “You might want to slip into something — ahem — more concealing, dear. Although I somehow don’t think that we will be going out again tonight.”
The artificial Jenny went into the real woman’s bedroom and found one of her nightgowns hanging from a hook in the closet. As she slipped into it and fastened the cloth belt loosely, she noticed that the message light on the answering machine was blinking.
Who could have called when I was out? She thought. I didn’t think Jenny was expecting to hear from anybody tonight. With a frown, the counterfeit Jenny played back the answering machine with the volume turned down low.
“Hello, dear brother,” came the real Jenny’s voice. “I hope your date went well tonight and you enjoyed yourself thoroughly. I assume that by the time you listen to this message, the masquerade will be over. Or should I say, the masquerades, plural.”
“I hope you will not mind this deception, honey,” the voice continued. “It took some time to set it up and get everything ready. I have to say, Dana didn’t take much coaxing to play along. She has wanted to spend some time with you ever since she all but groped you in the lady’s room at that cocktail reception last September, thinking that you were me. She said you were so convincing that she just had to spend an entire evening with you, just to see if a man dressed as a woman could be as sexy and alluring as the genuine article. I have told you, of course, that Dana is like me — quite bisexual. But despite your comments at the time, I really had a strong impression that she was more your type than mine.”
“Anyway, I hope the two of you had fun together. I know that Robert and I did – the real Robert, not the counterfeit you spent the evening with.”
“I’ll be home tomorrow evening, David. You can tell me all about it then.”
“Jenny” was totally stunned. What could his sister be talking about? He had spent the evening with the real Robert. What could she mean?
Still confused, “Jenny” walked back out to the living room area, where Robert, still naked, was reclining on the sofa.
Clearing his throat, “Robert” spoke first – in a voice that was unmistakably that of a woman!
“Judging from the look on your face, I assume that you got the message from Jenny – your sister,” Robert said in a breathy and deep but unquestionably feminine contralto. It was not the same voice he had used during the rest of the date.
Jenny sat on the sofa heavily, an expression of total perplexity on her face.
“What in hell is going on here,” David said in his own voice, so unhinged that he dropped his impersonation completely.
Robert leaned forward and placed his fingers under his chin, then pulled up and back, stripping off a remarkably life-like latex prosthetic face not unlike the disguise that David was wearing. As the woochie slipped off the crown of his head, a medium length brunette pageboy fell out from under it. Robert shook his hair free so it framed his face pertly. Only it wasn’t Robert under the mask; it was Dana Harwith.
“Damn,” Dana said with a rueful smile. “You weren’t supposed to get the message until I had left. Ah, well – best laid plans and all that.”
Jenny was totally dumbfounded. “Dana – but how…”
Dana fished a cigarette out of the little teak box on the coffee table and used the ornate silver lighter next to it to set it afire. She blew smoke out in a thin stream, combing her hair with the tips of her fingers, and looked at “Jenny” with a level gaze.
The sight was completely disconcerting. From the neck up, the person on the couch was Jenny’s female business associate. But from the neck down, it was a man – complete with a flat, finely chiseled masculine chest and a still erect looking penis.
“Jenny confessed about your impersonation of her at the cocktail soiree her company hosted last year – you no doubt remember the one I am talking about? The one where I gave you a big come on in the lady’s ‘Loo? Well, I had been flirting with Jenny for most of six months before that, always trying to lure her into my bed. And her response was always the same – a smile and a ‘No thank you, dear.’
“When I hit on you at the party, you seemed utterly surprised and baffled by my attention,” she continued, taking another puff from the cigarette. “I asked Jenny about it the next time I saw her and she told me all about your little masquerade.”
Shrugging, she smiled. “So Jenny and I set up this complicated scenario so I could get to see you in action for an entire evening – and I have to say, you are every bit as sexy as your sister!”
David felt crestfallen, but also strangely aroused to have spent the entire evening with a very sexy woman who had managed to convince him she was a man. “But how did you do it?” he asked in a stammer.
Dana, still bizarre with her male body, took another drag from her cigarette and smiled. “Honey, you aren’t only person who has studied drama and makeup. Before I decided that there was more money for me as a businesswoman than there ever would be in the theater, a took a dramatic arts bachelor’s degree at the state U. I did amateur theatrical work while I was in college and I still perform in an amateur musical comedy company in New York.
“As for the make-up and this male body suit, well, I don’t have your talent in that area, but you’d be surprised what you can afford to buy when you are filthy rich from a steamer trunk full of dot-com stock options,” she continued, stubbing out the cigarette. “I hired an expert with a special effects firm to do my costume. And the real Robert — the one you have been casting covetous glances at ever since Jenny’s first date? — was a good enough sport to coach me in how to walk, talk and behave like him. He ended up thinking I was pretty good at it. I take it you never caught on?”
David shook his – rather, Jenny’s – head in dumb amazement. He fished a cigarette of his own from the box and lit it, exhaling smoke in a ragged stream. “You were exceptionally good,” he said with astonishment. “I was completely taken in.”
With an impish grin Dana leaned forward and stroked David’s thigh suggestively. “Now despite what you told your sister about me not being your type, gay boy, you seemed to think I made a pretty good man, didn’t you. If you didn’t enjoy having sex with me, you are a much better actor than your sister thinks.”
David smiled. He had been had, but good. He had enjoyed sex with Dana, and he guessed that her penis not being real was no bigger a disappointment to him than his vagina being artificial was to her. In a way, they were even. They had enjoyed a wonderful night together, gender be damned.
“Actually, it was everything I had been dreaming of,” he said, drawing on his cigarette with a grin. “I guess dreams can be pretty superficial in a way, can’t they? I enjoyed your company all night long, and you are one of the best lovers I have ever had, Dana. I am a little miffed at everybody being in on this but me – but, believe me, it will pass.”
Dana giggled and stroked David’s thigh tenderly. “Good! No hard feelings then,” she said with a grin. Then, grasping the latex penis that still protruded from her crotch, she leered at him and added, “that is, except for this permanent one between my thighs. Shall we try it again and see if it still works, girlfriend?”
Stubbing out his cigarette and lapsing back into Jenny’s voice, David laughed and nodded.
“Definitely,” he said in his sister’s breathy contralto. “If you don’t have to take it back to some costume shop tomorrow, let’s see if we can wear it all the way out…”