Whine With Dinner

by: Anonymous Writer
















Grant Wellsley and his wife Editha had been seated at their usual table

near the center of the elegant and expensive downtown New York

restaurant. They had ordered their drinks, selected their dinner and

were now relaxing. They had been out on the town and had been to the

early show of one of the top plays on Broadway. Now, it was dinner and

drinks to end the luxurious evening. The club owner entered the room to

talk to the maitre'd as a few other staff looked on. This establishment

had been Grant Wellsley's nearly nightly haunt for decades, usually for

drinks and sometimes for an elegant dinner and then conversation with

several other of the town's billionaire class and captains of industry.

But, Grant usually had a young lady on his arm while his wife Editha was

relegated to home, busy with her social calendar which consisted of

ladies clubs and get-togethers. Of course Grant would bring his wife to

the club but rarely. Tonight they came to dinner as a couple and were

now at their table enjoying the atmosphere. The only strange thing was

that Grant Wellsley hadn't been seen much lately. Matter of fact he

hadn't been in for dinner at "The Densmore Club" in over a year and a

half.



Of course stock markets ebb and flow, new opportunities come and go but Grant had been particularly hard hit on his latest business dealings. His once thirty billion dollar fortune had plummeted to less than two billion in only the past five years. He'd become more of a playboy than a businessman and once his actions threatened the family one-percent lifestyle his mother-in-law finally stepped in and made her decision. Not everyone knew that it was Editha and her mother who really controlled the Wellsley fortune, matter of fact, Grant's last name had been changed from Hawthorne to Wellsley when he and Editha were married thirty years earlier. This fact was kept quiet and life went on with all appearing normal. As Grant sipped his double scotch on the rocks Editha finished her Pink Lady and gestured the waiter. "I'd like another round of drinks and we'd like another table please. Something in a quiet booth, I'm feeling a draft young man," she said. Soon they were seated in a darker more secluded booth. Another round of drinks soon arrived at the table. The talk at the front of the establishment continued in earnest. The owner Sam Densmore chatted with his matre'd and his top waiter. "How long has it been Mr. Densmore? Mr. Wellsley hasn't been here in over a year and a half," the matre'd wondered aloud. "Did you notice the moustache and sideburns he's always had are gone. And what kind of glasses are those, women's glasses?" Sam returned. "His skin looks smoother. Has he had a face lift? And I can't believe he's started wearing earrings. And his hair. Once a grey salt and pepper he's now a blonde? His hair's the same length but now seems to have a bit of a wave to it. And, he must have lost a good thirty pounds," Sam finished as he wondered aloud. What nobody could realize was that female hormones could work wonders on the male figure and the male psyche. Grant's once masculine frame had vanished, his breasts had budded, his waist had slimmed and his hips had widened and rounded considerably. Editha was now the one in charge. Grant wasn't his powerful self as he had been. He was still a presence but now took his cue from his wife. "I guess his failings in business caused his wife to put her foot down. They're still billionaires though," Sam finished as the matre'd and head waiter looked on at the distant booth before getting back to serving the arriving diners. Everyone had seen Grant's standard evening tuxedo, the standard upscale attire he always wore on evenings out but they didn't look closely enough. For now, Grant was wearing a large size of woman's shoes! Low heeled black patent leather slip on pumps that had a little silver fob at the front. The shoes could pass for unisex but just barely. And nobody noticed Grants tuxedo slacks either. They looked the same as always but were more tailored now and if one was to look closer they would have noticed there was no longer a front zipper. The zipper was now situated on the side in a most feminine fashion but luckily was hidden by the black cummerbund and tailored tuxedo jacket he wore. Editha was dressed in elegant fashion as well, her makeup and hair set properly and elegantly done in a vintage style, expensive jewelry and a full length layered blue nylon chiffon evening gown and matching clutch purse, with a mink wrap that had been left at the coat check stand. All appeared normal but at the secluded booth a more private conversation was taking place. "I should have made you wear this evening gown tonight, isn't that right princess?" Editha said in a mocking authoritative tone as Grant clutched his linen dinner napkin to dab his upper lip nervously. "You have a bit of a shine dear, should I get out the powder for you? Maybe add some lovely mascara and eyeshadow? And oh, how about some of my lovely gloss red lipstick? Do you like the shade dear?" She chuckled as she lifted her clutch purse to the table, opened it and began rummaging in a threatening manner as she relished her new control, taken back under her mother's orders. She took out her lipstick, Grant squirmed as she rolled the tube up and began applying the gloss red lipstick to her lips in broad heavy strokes. "You, don't prefer makeup this evening princess? Well, for now I guess I can understand," She mocked as she finished with the lipstick then put the purse away again as Grant breathed a sigh of relief. There would be no more adulterous behavior no more business mistakes now, because Grant was under mother's and Editha's full and absolute control. He hadn't initiated this night out, he'd been forced out. And in this new arrangement he had soon learned that, to get along you go along. Grant knew he was too old and set in his ways to end up penniless and on the street. The humiliation of his situation was more than unpleasant to be sure, but, the thought of being on the street made his head spin. Half way through their second drinks Editha opened her clutch purse and took out a cigarette and holder and a gold lighter with a ruby in a little gold medallion affixed to the side. Grant became immediately nervous as she lit her cigarette. He watched as she held the lighter and then gasped and squirmed in his seat as Editha slid the ruby on the lighter up. The ruby was a switch she could turn on and off, it was a remote control to make absolutely sure that Grant would always know his place. "I...I'm doing as you asked, please, please turn that off," He gasped. Finally, Editha switched the ruby off, the little red ruby light now dark once again as she chuckled and put the lighter back into her purse then after clicking the clutch closed she put it beside her in the booth. Grant was now only slightly red faced, only slightly flustered as he wiped his brow and upper lip with the linen napkin once again before setting it aside. It was then that Sam arrived with an expensive bottle of wine. "So nice to see you again Mr. And Mrs. Wellsley!" he beamed. "I hear that you'll be relocating," he said sadly. "It will be a shame to lose such a longtime and generous customer." "Yes, we will be moving to San Francisco later next week," Grant returned. "Editha's mother lives there, it's where the company was founded." "Sounds like quite a change. What will you be doing there?" Sam added. "Well, it seems that I will be retiring. I'll be staying around the house mostly, helping out with things while Editha continues on with the business," Grant replied with as much dignity as he could muster. "You do look healthy though Mr. Wellsley. Must be the clean shaven look. Your skin looks smoother but those little diamond stud earrings?" Sam asked. "Ah, trying to appear a bit younger, more hip. But at least I'm past the face lift," Grant said trying to pass it off as he noticed Sam looking his hair over. "Ah, that's it, a face lift! I thought so," Sam returned seemingly satisfied. That would explain the smooth skin and no wrinkles for a man in his late fifties. It went with the loss of thirty pounds as well. Finally, Sam finished his farewell and wished the couple well telling them they were welcome back anytime. He smiled as he left. And that for now was it. Prying eyes looked no further as the diners continued their drinks and small talk. Editha and Grant were now able to continue their quiet evening. "There's still that last bit of masculinity we need to overcome darling but after your appointment for your castration in another two weeks once we're in San Francisco I am quite sure you'll continue coming along just fine," She said smiling, nearly beside herself with satisfaction now. Grant Wellsley had been a rich and powerful man, a ruthless businessman, at least he had been. Nobody talked back or talked down to him, no one dared because a meeting or a phone call would be all it took to ruin someone's business or career. That is why nobody mentioned the feminine style of Grant's shoes that evening. That is why they didn't mention his smooth skin and lack of moustache, or the diamond stud earrings in each earlobe. And they didn't mention his new eyeglasses that had gone from black horn rims to a beige frame with jewel encrusted edges. They were women's frames but although they didn't look overly feminine they certainly weren't glasses any man would ever wear. And just above the glasses, the once dark bushy eyebrows were now dyed the same blonde as his hair color and trimmed tight and although not plucked into a high and feminine arch, the brows were feminine indeed. And the now blond-ish wavy hair style was a bit different too. Secretly, it was a woman's dye and hair set trimmed short! And when he handed out tips the waiter staff failed to note Grant's now well manicured fingernails, all trimmed and filed into smooth ovals with unmistakable clear gloss on each nail with just a trace of pale pink. Finally, the heavy masculine cologne he always wore had been replaced by a sedate woman's perfume, the slight floral scent not as strong as some but it was definitely not a masculine scent. It appeared that Editha had either initiated or readily approved Grant's new "metro-sexual" look. But it went far, far beyond that. Editha smoothed her gown and crossed her nylon stockinged legs with a whispering zip. She touched her well lacquered hair set with her palm before reaching for another sip of her Pink Lady. She picked up the glass and gazed upon her efforts. "You look lovely this evening darling. Simply lovely. Do you feel feminine now, hummm?" She tittered in a feminine lilting tone. When Grant didn't answer quickly enough she reached back into her purse and produced her lighter once again and teased the ruby switch with her long, gloss red fingernail. Grant took immediate notice. "Yes. Yes, I feel...I feel f...feminine dear," he gasped nervously as Editha tittered toying with the ruby switch at the side of the lighter. "I imagine you do precious," she giggled. "Enjoy your last night out. Within a few more weeks after we move in with mother and after your full reassignment that will finally make you into a woman, you'll take over duties full time as mother's maid I can assure you all those nasty masculine thoughts will soon fade away," She said with certainty. "Then we'll be quietly divorced and you'll have your name changed from Grant Wellsley back to Hawthorne, of course you won't be Grant any longer. Mother has chosen Ms. Joyce for your new name. Such a more suitable name for a proper and feminine lady don't you agree princess?" She giggled still holding the lighter. She then switched the switch on causing the ruby to glow red, the remote control sending out the activation signal. "Yes, you're going to become a regular lady." Grant went rigid momentarily and gasped in wide eyed surprise at the effect of Editha's activating the switch. She smiled with satisfaction as he squirmed in his seat. He was soon dabbing the sweat from his upper lip with the linen napkin once again and wiping his brow then setting his hands back down he gripped the napkin tightly and sat as quietly as he could. No one seated in the restaurant or waiting the tables or bringing drinks could know the full effect of Editha's remote control device. She'd had seen to it that Grant had been cleaned inside and out, finishing with a floral scented bubble bath. Then, before dressing for the evening she'd made sure to insert the plug fully into Grant's bottom. She'd trained Grant for over the past year and now, he could with only a little effort be fitted for a life sized phallic shaped plug. The plug fit tight and secure, the deep end of the shaft pressing firmly against Grant's prostate. Once the plug was activated Grant's milking procedure would be by remote control and hands free which delighted Editha, especially now out in public where Grant would just have to sit and endure his latest milking to it's greatest effect. And there he sat, under Editha's total control. And under the expensive tuxedo, beyond the ladies black flat pumps, the ladies side zip tuxedo slacks and beyond all the other feminine touches were what Editha considered proper under things. Grant had of course been Naired and waxed smooth below his trimmed and plucked eyebrows, not a hair remained on his body with the exception of a little triangle shaped trim below, which was also dyed a blonde that matched his new hair style. He'd already had a pedicure, each toenail trimmed then buffed and polished in a high gloss red. She'd made sure he dressed properly for the evening. After the snug fitting remote control plug came white, lace trimmed ladies nylon briefs. A pad was inserted into the panties and Grant's now atrophied testes were pushed deeply inside him before his flaccid manhood was pulled back tight. After the panties were pulled and smoothed up high and tight on his waist she added nude support pantyhose. A sturdy six strap garter belt came next followed by opera length sheer vintage ladies hose. Once the stockings were gartered high and tight and wrinkle free a sturdy and tight high waist white panty girdle was fitted and pulled tight until Grant's crotch was smooth, the center seam of the girdle cinched tight giving him the appearance of woman's vaginal lips! A white nylon pants liner came next. It was a bit like pyjama bottoms but these were long and lace trimmed at the cuffs, designed to move easier and feel even silkier under any type of slacks. The sensation was unmistakably feminine. And then came the white, lace trimmed playtex cross-your-heart brassiere! By now Editha's addition of the pink female hormone pills that Grant now took with each breakfast with a vitamin had caused him to blossom. She nearly swooned with excitement as she fitted the 40 "B" cup brassiere on him, easing the budding breasts into the lace trimmed satin cups, hooking the back and then adjusting the straps gave her satisfaction to no end. When she finished with a lace trimmed white nylon camisole and fussed with the straps she knew that with the way Grant looked now, he wouldn't be running around with other women ever again! She was now satisfied he could finish dressing himself. The starched tuxedo shirt came next, then the side zipper slacks and slender belt and cumber bund. Then a five button vest and finally the tuxedo jacket, cut in a loose double breasted look to hide his now feminized chest.. Black dress socks went over the ladies hosiery. He finished by slipping into the ladies black, flat pumps. They'd then left by limo for the evenings activities. Editha then switched the ruby switch to the next setting. She put another cigarette into her filtered holder, lit it then as the smoke curled up from the cigarette she sat back to watch and enjoy her efforts. Grant grunted, his hips and bottom seemed to undulate back and forth now. His face reddened as he gasped through clenched teeth. "Feel how silky all your pretty, lacy nylon under things are as you wiggle in your seat princess? Hummm? Such a feminine sensation," She chuckled mockingly. "My little precious being stimulated. I imagine your little nipples are all nice and erect now under the camisole and in the cups of your lacy new bra. Mmmmm, it must just feel so delicious doesn't it darling?" She cooed as she looked on. Grant's eye's rolled, his eyelids fluttered, his face reddened as he gasped while wiping his lips and forehead once again, and all the while he continued to squirm in his seat, his wide hips wiggling, undulating involuntarily now from the plug's massaging action as it sent silent vibrating waves pulsing against his prostate, waves that encompassed and massaged working him higher and higher to a fever pitch. "Don't make a scene now darling," Editha cautioned with a lilting giggle. "I want to make sure you have as feminine an experience as possible. Isn't it delicious?" "Unnghhhh, plea, please Editha," Grant blubbered and grunted at his limit of composure as his wide hips continued to undulate slightly grinding into the seat. Then suddenly, The club's owner Sam Densmore returned to the table! Editha reached into her clutch purse and quickly switched the ruby switch off allowing Grant to sigh in relief. "Is something wrong Mr. Wellsley?" Sam asked after seeing Grant wiggle in his chair and wiping his brow with the linen napkin. "No, no," Grant replied as he composed himself, his masculine demeanor returning if for only a fleeting moment. "I just swallowed wrong, a bit of acid reflux I guess. But I feel better now," he replied as his calmness returned. Then Sam asked for his new address so they might keep in touch. Grant wrote out the address on the corner of a menu, Sam thanked him once again then left the table. "My little priss. Pretending to actually act like the man you used to be," Editha hissed as a thin vengeful smile crossed her lips and she reached back into her purse once again and clicked the ruby switch back on, but this time to it's highest setting! Grant grunted and swooned once again, helpless. "We can't have that now can we? One way or another you're going to learn to be feminine, submissive, ladylike, and demure. We're going to purge you of all those masculine thoughts and actions, aren't we sweetie?" she cooed in a feminine lilt. This time Grant gasped louder, his hips bucked forward and he was forced to hold the table with both hands. A few diners were now starting to glance trying not to stare but as Grant mustered his will to fight the sensations of his milking they began looking away, all to Editha's enjoyment. "Once we get moved, mother will get started on you. Your credit cards will be gone as will all your accounts and any access to money. Your male clothing wardrobe, gone, all of it. Your atrophied little testes will soon be clipped and that will allow us to have your papers changed to show you as a female. Then you'll start taking female hormones full strength and living full time as a woman, and to keep busy you'll become a proper house maid. And once the lovely Joyce Hawthorne heals up from her reassignment surgeries, Grant will simple cease to exist," She said with relish, spelling out Grants future. "But of course, I suppose you could fight us, but would you really want to start over at your age darling? Over the years you've managed to alienate and hurt most every business associate you ever had. I imagine you might have a lot of trouble even finding a job now. Fast food? Or maybe a hotel maid? That would be so tragic," She chuckled as Grant writhed. "After a few more years with mother's training, you'll be a proper and very ladylike woman's maid, all prim and proper. Yes princess, you're going to forget what it was ever like to have worn pants or even what it was like being a man." "So, come on sweetie, mmmmmm. Yes." She smiled with a knowing wink. "Just a little bit more precious. Mmmmm, feels so goooood doesn't it? Closer, closer darling. Yes," she chuckled. Grant couldn't escape, his hips wiggled and bucked in the dark booth until finally Editha got her wish. Grant's pad had been wired to sense moisture, the green light on the lighter began to blink, then finally stayed lit to indicate that Grant's prostate had now been fully milked. The weak and watery emission soaking the maxi-pad in the vintage ladies panties had signaled the little green light. Editha switched the switch off fully then put the lighter back into her clutch, snapped the clasp on the purse closed and then set her clutch purse back beside her in the booth. She touched the side of her hair set again and adjusted herself in her seat. And as she reached for the last sip of her Pink Lady the waiting staff arrived with their evening meal and set the shrimp cocktail and salad in front of Editha. They set a plate of prime rib, baby potatoes with sour cream and asparagus spears in front of Grant. As the waiter left the table Grant, although hungry, slid the plate away. His thoughts were now elsewhere.