The "Mrs. Hollingsworth Project" (Part 8) free porn video

"The Mrs. Hollingsworth Project" (Part 8) Three days later Tim checked out of his room at the clinic. He then returned to his room in Ms. Lawrence's apartment. Then another five weeks passed. Bright and early on a Monday morning Ms. Lawrence was in the kitchen having breakfast when Tim entered the kitchen. He was dressed in men's pyjamas, men's slippers had combed his hair back tightly and wasn't wearing any makeup or jewelry. The salon nails and any trace of the gloss red polish had been removed, the scent of Old Spice now floated around him as he shuffled into the kitchen his long men's bathrobe undone, the sash hanging loose as he smelled the coffee and moved to the counter to take a cup off the rack. Ms. Lawrence took notice of the look, she also noticed the obvious curves and the presence of his ample jiggling breasts which were now hard to hide. Even though the laser electrolysis treatments were nearly complete she noticed that Tim hadn't shaved for days, she saw the fine wispy whiskers on his cheeks and chin. She tried not to giggle as Tim made a pretense of lumbering into the kitchen in a manly way that was now almost comical. She watched as he poured his coffee then commented. "Another day off? I see you've been shopping too. The J.C. Penney men's collection?" she mused as Tim paid her little notice as he plunked down at the table to his coffee and unfolded the morning paper with a snap. "Looking for another job?" she asked. Tim replied, "Anything's possible." "Yes. Yes it is. Or maybe it's just a short vacation?" she added as she got up from the table and set her plate and cup in the sink. "I have a meeting to attend to. ... I'll leave you to your day off then." she said as she left the kitchen. Shortly Tim heard the heavy apartment front door close and he was once again alone. He put his paper down to gaze out the windows at the crisp clear day and at the city below, nothing much apparent on his mind. Meanwhile, Ms. Lawrence was just entering Richard's main office. The conversation started almost immediately as she approached Richard's large desk. "It's been weeks. No evening dinners, not even any progress reports. Is he even still here?" Richard asked after his staccato roster of questions. "He's still here. Barely," Grace said as she took her seat in front of the desk. "What does that mean?" he returned. "It means we're on hold. For the time being," Grace replied. "He certainly must know the situation by now," he continued. "I'm sure he does. But there have been a lot of changes," Grace went on. "This isn't just a girl going to my 'charm-school' you know. I've never done this before. But, rest assured, we've made great progress. These things take time." "How much time?" he asked. Grace tried to explain. She'd put him in that pink brassiere at the clinic over her ultimatum but the sight of his male clothes and the offer of one thousand dollars to walk away from the whole deal was still on Tim's mind. But the point was nearly moot now. Months of 'charm-school' lessons, months of hormones, laser electrolysis, facial feminization surgeries, breast augmentation and the growing curves could no longer be denied. He'd found his street clothes at the back of the closet, the blue jeans, the T-shirt, leather jacket, tennis shoes and the baseball cap. The shoes and cap fit, the jacket was workable but in the shirt he didn't look like a man anymore and his hips were too wide to fit his jeans, and the waist of the pants was far too large. This obvious revelation caused Tim to re-think his situation. Ms. Lawrence made it a point to mention that Tim was already past the point of no return, that he was far more feminine than masculine now. They knew he enjoyed dressing as a woman but Grace mentioned that the sensation of wearing those clothes constantly and in doing the hair and makeup and in living in such a rigid feminized lifestyle had become overwhelming. It was a type of overdose and the only way to keep mental balance was to allow Tim to step back from that edge, at least momentarily. "You've got him up to speed on his 'housewife' and hostess skills and have gotten him up to speed in living full time as a woman right?" he asked. "Yes. We need to wait until his mind catches up is all," Grace returned. "We need to get his mind off of his thoughts, to get him busy doing other things. How about his typing skills, and shorthand?" Richard added. "He could already type when he got here but he's learned shorthand now as well, he's quite good actually," Grace replied as Richard paced the office deep in thought. "Well, he's still my executive secretary. Maybe it's time to take his mind off his thoughts and give him something to do," he reasoned as Grace looked on. Eight am. Tuesday morning. Grace entered Tim's bedroom and opened the heavy drapes causing Tim to stir. Shielding his sleepy eyes from the light with his hand as he sat up. The room looked lived in now, unkempt. A pizza box sat atop the dresser, men's clothes strewn about and Tim as he arose with his unkempt mop of brown hair still had his visible shadow of wispy beard. A recent copy of Playboy magazine was on the floor by the bed. Grace noticed the girl on the cover not looking as feminine or as pretty as Tim did right now. "Time to get up," Grace said with authority. "We have a lot to do today. And while we're gone I'll have this room properly cleaned." Two hours later Tim laid on the massage table in the corner of the master bath being massaged, his face once again porcelain smooth after yet another laser electrolysis session and a close razor shave. He felt the soothing coolness of the cream as the attendant applied it to his face as he laid there, his hair already washed and set and back in tight curlers with cucumber slices over his eyes as the manicurist once again applied the long salon nails and painted them a bright gloss red. Tim laid there indifferent being massaged with warm perfumed oils, his smooth hairless skin gleaming in the light as Grace went over the itinerary. "There's a working lunch scheduled across town today and an evening cocktail get-together for late in the afternoon, bring a stenographer's pad with your briefcase and a current appointment book. Tomorrow you head for San Francisco and then you're off to China for two days of meetings, and then Los Angeles, Denver and back to Chicago, for now that is. Richard only brought me up to speed on this short list. He's very busy with business and needs his secretary," Grace said as a matter of fact. "Why do I have to do all that. I dress for Mr. Hawthorne like he likes isn't that enough?" Tim grumbled in as low a tone as his new feminized voice would allow. "Well, you still work for the company don't you? You hired on as Richard's executive secretary. It seems that he has need of your services now," Grace said, then added, "Your office skills and feminine deportment and grace are needed it seems. And after all it is something to do isn't it? Get out, get some sun, get some fresh air." The ladies turned Tim over as he clutched the pink bath towel, they then began massaging his back and legs. He once again realized he was living a pampered existence, his thoughts of living in a crummy apartment and working double shifts in an underpaid impossible job returned but were soon soothed away by the perfumed air, the soft music and attentive massage. Grace waited for an answer. "I notice you're not driving that old clunker anymore. I noticed the new Mercedes coupe in your parking place downstairs. The pastel color is a bit feminine but I'm sure that will be easy to get used to. The new lifestyle, the nice clothes, the elegant accommodations the travel, the world class dining. Having someone to bathe you, and massage you and do your hair and makeup and see to your every need. Is it really that bad? Living a pampered life?" She reasoned knowing full well she was bringing up the idea of the cheap apartments and crummy jobs and even the possibility of soup kitchens and the reality of the hard, gritty life on the streets. And in the way Tim looked now, certainly anything but masculine, he'd be out of place trying to be his former self. She didn't mention that this, this second to last stage was to get his mind right now. A little more work, a little more polish, a little more distance from his male self and Tim would become Tiffany. One more procedure would be needed after that but all in good time she thought as she continued spelling out Tim's upcoming itinerary. An hour and a half later Tim was properly dressed once again and starting a new work week. Tim took a deep breath as he exited the limo with Richard. He felt the feminine clothes against his skin once again and the familiar "shick- shick-shick" whispering zip of the sheer beige nylon stockings as he minced into the upscale restaurant close by Richard, his purse over his shoulder a briefcase in his right hand. The three men at the far table rose as the two approached. Smiles and handshake greetings began. "This is my executive secretary, Miss Tiffany Benson," Richard introduced. The men took notice, smiled and offered gentle handshakes that Tim accepted. They noticed the feminine deportment, could smell her perfume as they heard the swish of 'her' satin lined skirt of the ladies suit 'she' was wearing. They noticed the smooth shapely legs perched atop the high stiletto heels, the "Tiffany" necklace, the gloss red salon nails and the now feminine curves never realizing that Tiffany was actually, for the moment at least, a man named Tim. Richard seemed to enjoy the moment as they all took their seats. The talk turned to business over lunch with Tim taking notes and providing pamphlets and handouts to Richard's assembled guests. Another meeting took place after lunch across town and soon Tim was back in his apartment getting ready to accompany Richard to a late afternoon cocktail party. Grace put together Tim's outfit. That early evening Richard showed up at an elegant affair with Tim on his arm. The men immediately took notice of Tiffany. How she minced and wiggled into the room. They noticed the knee length layered nylon chiffon halter top mauve cocktail dress, the smooth, shiny sheer nude/grey nylon stockings on the long and feminine legs. They noticed the 5 inch heeled ankle strap sandals done up in a matching shiny mauve satin. They noticed the delicate silver ankle bracelet with the little silver bow, the perfume the elegant evening makeup, matching nail polish and the up-do hairstyle, the dangle earrings and the delicate pearl necklace and even how she held her mauve clutch purse. Richard noticed with muted excitement how this new "trophy-girl" was being noticed by the other men and even a few women. Because he knew that most women simply weren't this elegant or as ladylike in this day and age. The evening was a complete success. He made a mental note to give Ms. Lawrence a bonus for the month. Tim seemed to be enjoying the attention but his eyes seemed vacant at times. But still Richard kept him busy and on schedule and working every day as his executive administrative/secretarial assistant. The whirlwind trip to the Far East took place and more appointments and meetings continued until they touched down in Los Angeles. After a few more meetings and lunches and jet hops across the country Richard and Tiffany finally returned to Chicago. And as the days passed and then the weeks people began to notice that Richard and Tiffany seemed an inseparable item, more than employee and employer. And while Tim was kept busy Ms. Lawrence continued her work. She started by getting rid of Tim's robe, slippers and pyjamas from the J.C. Penney men's collection. It was now time to move Tim into his new digs in the master's penthouse, into Tiffany's own personal boudoir suite. Grace and Richard had already had the conversation. The conversation about Richard having a ladies "boudoir" suite constructed in the penthouse apartment. "It's a bit excessive, almost too feminine," Grace said. "About as girly-girl as one can get," she'd noted. This would indeed signal to Tim that things were indeed changing the moment he saw his new living quarters. But the process and the plan now, at this point was nearly complete. Tim was indeed leading an elegant pampered life now but as he mentioned long ago he now realized he was indeed "going through life on high heels," he was now fully used to the women's clothing, doing women's things and being seen as a woman. But when he was alone with his thoughts they were confused thoughts, he felt his manliness, his masculinity fading as never before now. Grace and Richard even began referring to Tim as Tiffany as with the way he looked now it was an absurdity to even consider him as a male any longer. The next day would be moving day, that would be the ultimate test. The next morning Tim's nylons zipped as he minced from the elevator on the top floor with Ms. Lawrence to the main door of Richard's penthouse apartment. Ms. Lawrence opened the door then handed Tim the key as she led him inside. He'd been there before but had never been shown the boudoir that had been put together for him. He was astonished when Grace led him down the long carpeted hallway to the large white double doors and swung them open. Tim was aghast at what he saw. Ladies were already coming and going bringing his things from the other apartment setting him up in his new quarters. He felt his nylons zip as he minced into the main suite, he smelled the floral perfume in the air. His head began to spin once again at the sight of the excessively feminine boudoir. It was done up like those luxury apartments in the old black and white movies, everything all satin and frills, ribbons and lace. A huge vanity, a large poster bed covered in a lace edged canopy, the furniture all white French provincial sat in the main bedroom. Before he could speak Ms. Lawrence showed him the dressers, the drawers brimming with expensive ladies lingerie. She swung open the double doors to the walk in closet to reveal row upon row of ladies dresses and gowns, skirts and blouses and elegant lounging gowns all done up in satin and nylon with frilly nylon chiffon robes. Tim realized that the walk in closet alone was nearly the size of his old apartment! Grace moved him on, down the hallway to the master bath. The pale pink carpeting covered the floors, while delicate wall paper and matching pink paint covered the walls, paintings were hung about the rooms as well. Feminine works showing floral arrangements or ballerinas. The boudoir was absolutely devoid of any trace of masculinity. Tim felt he was being pulled, pulled even further into feminization, further into Ms. Lawrence's and Richard's plan. It was still reversible he thought as he breathed open mouthed through his gloss red lips as he followed Ms. Lawrence down the hallway and into the large master bath all done up with pink towels, pink fixtures with delicate gold trim in the white tiled floored room. But he felt what was left of his manhood and his nearly atrophied testes now in the smooth hairless scrotum with everything tucked tightly into a long legged panty girdle, he imagined everything shrinking further still with this continued onslaught of excessive femininity. But still, it was reversible he thought. Back in the main bedroom of the boudoir Grace said to take a couple of days to get acclimated and that she would return in the morning. Tim would be allowed a break from his busy executive schedule for awhile. But before she left a delivery was made. It was from an exclusive ladies dress shop. Apparently yet another complete outfit was brought in. Grace hung the items in the closet then left Tim to himself in his new suite. As Grace left the phone on the night table rang a few moments later. The voice said: "I'll be done around six this evening," Tim noticed it was Richard's voice on the other end of the phone. "Did Ms. Lawrence get you settled? How do you like the new place?" he said excitedly in an almost unbroken sentence. "Yeah, yes Mr. Hawthorne. I'm here," Tim said as he looked around the room feeling very out of place. "Yeah ah, it it's nice alright," he gasped then felt his face redden slightly as he spotted his reflection in the triple floor length mirror along one wall. He became lost in the room and lost in the image he now saw, for there was a woman there now, Tim was gone! "Is the place alright?" Richard continued. "Yeah, yeah...it's.....ah really something!" Tim added trying to reply while trying to decide whether or not to continue this embarrassing conversation or jump out the window! "Well, take the afternoon off, relax. I thought maybe a nice dinner at home tonight, about eight? Nothing fancy. Get changed for dinner though, put on something nice. I'll show you around the place again, get you used to the layout while we sip some wine. Then dinner. I hope prime rib will be alright for tonight? See you at eight then," he said in a bit of a hurried business like tone as he finished the call leaving Tim still holding onto the pale pastel pink receiver as the call ended. Late that afternoon two lady attendants showed up at the penthouse to help get Tim ready for the evening. The bathing, the massaging and the hair and makeup primping began all over. He could of course do his hair and makeup but not in the elaborate styles Richard often called for. And he could by now pick out his own clothes and dress himself but with well paid attendants at hand that process was for much of the time also "taken care of." After a hot soothing perfumed bubble bath he was back in the corner of the large master bath that had been set up as a type of salon. As he laid on the massage table and the ladies went to work with another massage and began the primping and preening with his hair and makeup Tim's thoughts began to wander once again. He remembered sitting at the bar feeling the five o'clock shadow as he rubbed his chin then tipped his baseball cap back as the bartender brought a cocktail napkin and he ordered a cold beer. "What can I get for you buddy?" The bartender would say. And then his thoughts went to the recent meetings at the supper club where Richard's business associates shook his hand gently and looked him over with a muted, almost excited lust as if he was a woman. He remembered the last trip to that corner bar when the bartender approached. The "what can I get for you ma'am--oh, sorry mister, what do you need." statement still ringing in his ears. How he was now being seen as more of a woman than a man. But that was months ago, many months ago! And he remembered how ill fitting his old T-shirt and blue jeans were now and how even the pyjamas and robe he got from Pennies didn't seem to fit right and how Grace seemed to stifle a giggle when she saw him shuffle into the kitchen that morning for coffee. His thoughts were confused, his male thoughts, thoughts of his former life continually fading until the memories seemed like those from someone else's life! Something he'd read about maybe? The deep massage of his calves and lower back brought his thoughts back to the present as the ladies worked. The feminine situation, his new situation and arrangement came flooding back in thought. If he could maintain his employment duties and if he could look and act with proper deportment for the evenings dinner. But then again, Grace had already seen to that. Tim's mind became unfocused in a swirl of confusion. But the pampering continued, he wanted for nothing now. The thoughts of stocking shelves at the hardware store, riding buses when his car wouldn't start and living in a crummy apartment eating Spaghetti O's was a memory, an ordeal he wanted to forget. And the massage continued. He thought of these "salon" treatments, the massages and rubdowns. Being measured for custom made vintage clothes, going out for tailor made ladies suits and gowns and for contemporary clothes to be seen in at business meetings and gatherings. And the lessons, the constant lessons from Grace in all things feminine. A harmless fetish for women's clothes, a Halloween evening, a costume done a bit too well. And then to be spotted by someone, by Ricart Richard Hollingsworth who shared the same view as he did but from the "other side of the fence," A man with an idea and the money and connections and power to make almost anything that could be imagined come to pass. An offer made and then hesitantly accepted. Each step pulling him deeper and deeper into this all encompassing plan, a plan that was now nearly taken to the feminine limit. Tim looked like a June Cleaver, a Donna Reed now. The look was perfect, as were the mannerisms and deportment right down to the turn of the heel. And then the little procedures, the laser electrolysis, the facial feminization. And then the "vitamins" the vitamins that turned out to be female hormones, and then the doctor visits and the estrogen injections and the breast augmentation at the clinic where Grace ended up by fitting him into his first real brassiere. His life had become as easy and as frictionless as the lingerie he now wore. Powdered, plucked and perfumed, painted, primped and pampered and fussed with until not a hair or even thought was out of place. Tim had become a thoroughbred. He was still thinking that when the attendant zipped him into the layered, royal blue nylon chiffon cocktail dress for the evening. Richard was more than pleased when Tiffany minced into the living room of the main penthouse. After a quiet candle lit dinner and a few glasses of wine to finish the evening Richard noticed Tim sitting at the other end of the table still looking elegant and acting feminine but quiet, distant and in a pensive mood. "You look nice. How you getting along?" Richard spoke. "Alright I guess," Tim replied quietly almost with a defeatist attitude. "You're doing well with your job and I must admit that you've become quiet easy on the eyes," he said. "You're being well taken care of?" "Of course," Tim returned. Richard mentioned that Tim's duties as executive secretary weren't mandatory, that he would eventually be promoted. Promoted to "trophy wife" status. After all that was the plan all along. Even Tim realized that by now. Swirling around the penthouse apartment he would be a socialite, maybe even a hostess, but little more. Of course women of the 1950's lived the vintage life and actually did housework and such but at the level of vintage perfection Tim now found himself one couldn't do heavy housework in a full skirted rayon house dress, a petticoat, seamed stockings and 5 inch heels with the pearls and earrings and full makeup and not a hair out of place. He would now be "taken care of," There would be no dish-pan hands. Tim felt the slippery sensation and heard the familiar whispering zip of the sheer nylon stockings as he crossed his legs smoothed his cocktail dress and took another sip of his wine but Richard stayed silent as Tim sat deep in thought, his mind reeling once again. He thought of taking a break, going back to that bar for another beer hanging out with other guys. But those thoughts were fading as was the reality because now he would be as out of place as Marilyn Monroe trying to be a guy even in the blue jeans, T-shirt, jacket and tennis shoes. Imagine, getting lipstick on a thick Cuban cigar as he chewed it while sauntering up to the bar? No. No, that simply wouldn't work anymore. He became acutely aware of his feminine personae and the feel of the feminine clothes now, the feel of his tightly curled hairdo and the taste of lipstick on his lips and the smell of the perfume that floated around him. Richard noticed the uneasiness as Tim squirmed in his chair. "It is what you wanted isn't it?" Richard asked. "I don't know," Tim returned as his long eyelashes fluttered. It really had been the perfect arrangement. A one-in-a-million arrangement. Tim had his fetish for vintage women's clothing and Richard had a fetish for vintage women. The one problem in the way was a problem that was now nearly out of the way. They both sat at the table realizing the same thing at the same time but Tim was having his doubts. Was it worth it? Tim poured another glass of wine and got up from the table. He minced into the living room, past the fireplace then moved up the carpeted steps to once again look out the large row of windows to view the city below. Richard heard the swish of the dress, the zip of the nylon stockings and noticed the wide hips and the mincing high heeled steps now as Tim moved with practiced grace just like a model. He noticed the jiggling cleavage in the royal blue nylon chiffon halter top cocktail dress and how his facial features and his look and his movements in the candle light looked spot on flawless now. Richard thought back to the Halloween party at the bar downstairs and how the girls teased Tim pulling at the hem of his house dress and how they managed to swirl it up to reveal his stunning nylon stockinged legs and how Tim became flustered as he swished the dress back down and how he'd caught his eye even with the sloppy hairdo and the poor application of makeup. But now, that same effect had been greatly amplified, a one- thousand percent change. He then mused as he remembered seeing Tim for the first time on the yacht in the middle of the Atlantic ocean in his full "boudoir" regalia, the black lingerie. Even as good as he looked then, he was way beyond that now. "I've got a meeting in two weeks," Richard said. "A bit of a working vacation, at a mountain retreat. It's a small private affair with a few friends, a get-together, a club of sorts. I thought we could go and relax for a few days," he offered. "A few close friends, mostly a billionaire's club type of thing but I think you'll like it." Tim saw his reflection in the large window once again, his confusion was complete as he struggled to remember his past. He remembered the hormone injections and how his face would flush as those masculine thoughts of his were pushed farther and farther into the past and how they continued to fade as his new life and new experiences took over. And for some reason he began to think he wanted another estrogen injection with the hopes that those memories would fade even further. "A vacation? What kind of vacation," Tim asked as he turned from the window then minced back to the dinner table. "A private party, a few couples and an entourage or two," Richard went on. "I thought maybe you could go as my 'girlfriend," he said as he took out a little black velvet box and slid it across the table to Tim. Tim opened it to see the large diamond of the women's engagement ring! "Go ahead. Put it on," Richard coaxed. "It's yours." Tim looked at the ring as Richard went on. "There really isn't any pretense anymore is there? We're both adults. Being a kept-woman won't be so bad. You've already had plenty of practice. Everyone who sees us together sees us as a couple-even though you're still my executive secretary. The promotion is real. You'll want for nothing." Tim already knew that but this was indeed the next step up the ladder and there were only a few more, maybe only one or two until he'd reach the top step. His stomach tightened and his head spun once again. Richard paused then continued. "Go ahead," he said. "We'll go at your pace. The ring is yours either way. You can stay on here and we'll work things out getting you comfortable in your new lifestyle or you can leave at your convenience." Tim paused in thought. "You're not a prisoner here you know. If you want to go through the trouble of changing back that's up to you but it would sure be a waste of talent if you ask me," he reasoned. "Forget about the thousand dollars. You must have known where this was going when Ms. Lawrence put you into that brassiere didn't you?" The statement shocked him a bit. Richard knowing about that but then he realized that Ms. Lawrence was also Richard's employee and she was quiet adept at making reports. "I know I like the clothes and all but I'm not a TS, not transgendered. And I'm not gay!" Tim replied in confusion. "I'm not gay either," Richard chuckled. "If you want to you can leave. It's up to you. That ring is worth around four million, it's yours. You could move away become Tim again, you could take your pink luggage, hop into your new Mercedes and head out then buy a modest house and by putting the money from the sale of that ring in an annuity you could live comfortably off the interest for the rest of your life. Your life as Tim. At 6% interest that's around $20,000 dollars clear, per month give or take--forever. If that's what you want." Tim took the ring from the box to look it over. "But imagine staying on here. The elegant lifestyle, the jets, the yachts, the world class destinations, the world class possibilities for a trophy wife," Richard mused. "You're almost there, why look back now?" Tim felt as if he'd been hypnotized as he slid the ring on his finger. He could feel the weight of the diamond and the ring was a perfect fit. They toasted the partnership with a final drink before ending the evening. Richard stood by the fireplace watching as Tim gathered his royal blue clutch purse and minced back to his boudoir in the 5 inch blue satin heels looking like a statuesque high fashion model.