Dream Girl

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A wealthy young man meets the girl of his dreams.
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komrad1156
komrad1156
3,758 Followers

"So what do you think, Dad?"

"It's nice, Tyler. And I'm proud of you." He looked over at his daughter and said without hesitation, "I'm proud of both of you." He looked back at his son and asked, "Is this your way of getting me to come visit more often?"

"Is it working?" Tyler asked in response.

"I wish. You know how busy I am, Tyler. You've got an amazing place here, but getting out to Seattle isn't easy."

Gerard Regan was indeed a very busy man. As a deputy secretary of defense, he put in a ton of hours, most of them at the Pentagon or traveling to one of the many bases around the globe. He loved his children, but breaking away for a visit really was tough. Most of the time, it was downright impossible. But when Tyler sent him some pics of his new place and the Olympic-sized swimming pool in a glass-enclosed area behind the house, he took four days off and flew out the Pacific Northwest where he'd grown up. As a career civil servant, he'd worked his way up to pay grade GS-15 and then moved into the SES ranks all in the Washington DC area and culminating in his current position as a political appointee.

Both of his children had been very easy to raise even having to do it on his own after the untimely death of his wife. Regan traveled a lot and had had to hire a nanny full-time to care for them. His mother visited as often as she good to help out with her grandchildren, but living in the Seattle area herself, it just wasn't practical.

As much as he wanted to be there for both of them, it just wasn't possible. And while he hated not being with his daughter as much as not being with his son, he was most concerned about his boy growing up without his mom. For Tyler, the biggest influences in his life had been his older sister, Cadence and the woman he'd hired to care for his them. He was grateful for one thing. The woman he'd hired had chosen to stick with him until Cadence was 16 and able to drive and care for her younger brother.

Regan worried about his kids growing up mostly alone like that, but he just couldn't marry another woman. He'd married once for life—until death do us part—and even though it only lasted for seven years, she'd been his one and only. She'd died when Tyler was only two and Cadence four. Regan had taken an entire month off to spend with his children while thoroughly vetting and interviewing prospective nannies. The first concerns about him not being around began when his nanny told him little Tyler had been asking to play with dolls. The greater concern arose when she told Gerard he was constantly asking to wear his sister's things and had even been wearing them around the house. The nanny knew not to draw undue attention to it so she never rebuked him. She just let his father know about so he could handle it as he saw fit.

Regan feared for his son's safety knowing how boys 'like him' got treated. Having no experience with such things, he took his son to therapy—or more accurately—sent him with his nanny—for many months. He also introduced him to every sport imaginable and did his best to make time to play sports of some kind with him every evening he was home as well on weekends. This dress-up thing seemed to die out and now as Regan looked at his 27-year old son, a strong, fit, muscular young man who'd been a state-champion swimmer in high school, he felt certain it had just been a childhood phase.

After high school Tyler had gone off to college and majored in computer engineering. By his senior year, he'd come up with a social networking program that became an instant success. What started out in a tiny apartment soon moved to small building and then into a huge complex in the city of Renton, just a few miles outside of Seattle. Social Chat was now valued at well over half a billion dollars and it all belonged to his son, Tyler Regan.

Tyler's sister had been his best friend his entire life and she was his first choice to serve as his chief of staff for their new business. She was not only whip smart and highly efficient, she was also beautiful and charming. And no one else but Cadence knew that Tyler had never really stopped wearing her clothes until he got so big he could no longer fit in them, and no one ever would. He'd looked ridiculous in them, but Cadence understood his needs so whenever it was possible, she made time for him to play dress up until he left for college. As far as she or anyone else knew, Tyler no longer indulged his former fetish and no one ever asked until one day when they were alone at work very late at night. Cadence told him she had a friend she thought he might like and asked if she could introduce them. Tyler hemmed and hawed and after some probing on Cadence's part, he finally volunteered exactly what kind of girl he was looking for. His confession not only didn't shock her, she wasn't really even surprised. He longer wore women's clothes himself, but was now focused on finding someone who did. But not just anyone. This person had to look a certain way and be interested in a guy like Tyler. Okay...in Tyler.

Cadence told him she understood completely and immediately hired a couple of very thorough, very efficient private investigators to look around the university campus for just what Tyler wanted. In spite of their best efforts, their long hours and hard work over the next several months had been fruitless.

"I can pay for the flights, Dad," he told him as they toweled off after their swim.

"It's not the money, Tyler. I have plenty of it. Not anything close to what you've got, but hell, I'll never spend what I have. It's just the time, you know."

"Yeah, I get it. Work has been everything for me the last five years. Late nights, weekends, holidays. But it was all worth it—I guess."

"You guess? Come on, Tyler! You're 27, fabulously wealthy, famous, and damn good looking. Speaking of which, when are you gonna finally settle down? I know 27 is considered young these days, but when I was your age your mom and I had been married for three years already."

"I don't know, Dad. I've just never had time."

"Tyler? We make time for what's most important to us. All of us always find the time to do what matters most. That's why your business has been such a huge success."

Tyler grinned and couldn't help saying, "The things that matter most. Like coming to visit your son?"

His dad laughed and said, "Planes fly to DC too, you know! That's not just a one-way street. Besides, you've got your own damn jet now anyway—smart ass." Both of them laughed as they headed inside to shower and have lunch with Cadence who had been spared yet another lecture herself on her 'need' to find a great guy, get married, and have grandchildren for her father.

As they ate, Gerard took a second bite at the apple. "So...is there anyone at all in your life, Ty? Do you even date?"

"Dad? Give it a rest, okay? I told you I'm busy."

"You're busy by choice now. Your company can practically run itself. It still needs your leadership, but it has your vision. You can afford to scale back. All you've gotta do is set aside the time for yourself and start looking. The right girl is out there, you know. Just like your mom."

Tyler didn't say anything so Gerard kept plowing. "You do like girls, right?" he said without judgment. He was simply asking. To make that point he said, "I honestly don't care as long as you're happy. But you need someone in your life. Something besides work."

Cadence played along as though that whether or not he liked girls was a totally ridiculous question by rolling her eyes and looking at her brother with that, "There goes Dad again," kind of look.

"Jesus, Dad. Gimme a break already. Of course I like girls." That was true but only partially so. Tyler had indeed mostly avoided dressing up like one ever since his father told him boys don't do that kind of thing, his rare moments alone with Cadence being the only exceptions. He'd channeled all of his desires into sports and later, work. But he never got passed his fascination for boys who did dress like girls. But not just any boy. His fascination was with those few who had the kind of features that allowed them to actually look like girls with the right hairstyle and makeup. And his greatest desire was to meet one or even help create one assuming there was a pretty young 'girl' out there who would be amenable to that kind of thing, even if she weren't yet aware that was who she really was.

In what little spare time he did have, he found himself invariably looking at the same kinds of websites on the internet. He watched 'transformation videos' for hours as cute boys turned into beautiful girls right before his eyes. It was mesmerizing and he'd often watch the same ones over and over again unable to believe he was looking at a boy rather than a pretty girl by the end of the video. More than anything else in life, that was what he wanted. A girlfriend just like one of those girls in the transformation videos he loved so much. He would do virtually anything to have a girl like that and should he ever find her, he would love and spoil her to the ends of the earth.

His interest in that kind of girl had begun in college and over time, his fascination continued to grow. Now he yearned for just that kind of girl, but he'd had no success finding her. It seemed highly inappropriate to pay a private investigator to find these beautiful boys-turned-girls, but he had no other idea how to meet one. Young, pretty crossdressers just didn't hang out in public places and of course, most of them were completely into real girls themselves making his quest seem like a modern-day 'mission impossible.'

He knew he would never, ever consider anyone who wasn't at least 18 and out of high school. Preferably, he/she would be living on their own although he knew that money was often an issue for anyone that age when it came to living arrangements. Most single 18 to 21-year olds would either be living at home, away at college, or in the military. Making matters even more complicated, once a suitable candidate had been found, that person would have his own life and family so what would be the interest in having a relationship with Tyler? Further, what were the odds one would ever want to be in a long-term relationship with him living mostly as a girl? Slim to none. Okay, because he was rich, that could seriously influence someone's decision, but he had no interest in buying love or even companionship. His deepest passion was to find someone who wanted to be exactly what he was looking for without being pressured into it.

He'd also repeatedly checked out dating sites for trans people, but even that was fraught with problems as he had no interest in transsexual women or in any of the male-looking crossdressers on those sites. Trying to find the kind of girl he wanted really did seem impossible. With his busy schedule, the whole idea was becoming an exercise in futility.

Lastly and as crazy as it sounded, he wanted a 'girl' with a penis, but he had no interest in touching it. He'd never found himself attracted to men, as men, and he was only occasionally attracted to certain genetic females. Tyler never knew whether or not any of that made him gay, and now he no longer cared. He knew what he liked and what he wanted, so labels held no interest to him. His dream girl had to be genetically male but want to be treated like a female, and someone who didn't need that part of her to be touched or even a part of their lovemaking. Crazy or not, that's what he wanted. He knew that with all these restrictions and must-haves, finding her might be a herculean task, one that had so far completely alluded him.

After listening to his dad, he had to admit he probably could back off at work. He didn't need to work 90 hours a week anymore. In fact, there was no longer any need to work at all. Then again, his motivation wasn't money. He was driven to make and grow and keep his company the best it could be. The question was this: was there any reason he couldn't do that by being there say...forty hours a week like a normal job and give himself more time to find this elusive creature?

"You may be right, Dad. Maybe it is time to pull back a little and try and find the right...girl."

"That's my boy! And then you two can give me a grandchild and I guarantee you I'll be flying out here all the time."

After his dad had flown home, Tyler let Cadence know he was going to start scaling back and take more of a personal interest in finding this elusive creature he so desperately wanted to find.

_________________________________

"Danny? You ready to go?"

"Be right there, Mom," he called down. He finished getting ready and headed downstairs. "Sorry, I know we can't be late."

"No, we can't! This is your first day. Do you know how lucky you are to get this job? I've only been there for two weeks but as soon as I heard Mr. Regan was looking for someone to clean his pool, I asked the manager at the service to consider you. He hired you because I vouched for you. And because I work so hard, that kind of recommendation matters. So please, be on time, do a good job, and make me proud."

Daniel Vance had just graduated from high school a month ago and would be the first person in his family to go to college this Fall. But his mother, Anna Vance, could never afford to pay for even half of what he'd need, so a job like this meant the difference in not being able to contribute anything and being able to cover at least some of those costs.

Elite Services provided just that—services for the elite. Chauffeurs, pilots, maids, butlers, chefs, personal assistants, cleaning crews, and pool maintenance were just a few of their specialties. And the pay was excellent, especially at the lower end for unskilled laborers. Danny's mom couldn't earn half of what ES paid her and when she got this job she was beside herself. When Danny also got hired on, she'd gone to morning mass for the first time years to give thanks.

Danny had been one of the smartest kids in his high school. He'd been the class valedictorian and gotten a partial scholarship to help with the cost of tuition. It was the room and board and everything else that kept his mother up at night. Danny was a shy, quiet boy who'd never played sports. He preferred music and dancing and academics. Ironically, he'd always been very popular with girls. He was, after all, a very cute boy. Not handsome but—cute. He had beautiful, high cheekbones, this amazing smile surrounded by soft, full lips, flawless skin, and those eyes...those eyes that were so...appealing to both boys and girls and Danny had been asked out more than once by guys who'd recently come out. He was just to shy to really date anyone, male or female. His long lashes were the envy of every girl in school and Danny had no shortage of girlfriends. Or rather, friends who were girls as he showed no real interest in dating any of them. He preferred hanging out with them and had even been invited to a handful of slumber parties, one of the few places where he felt perfectly at home.

In terms of style, he looked a bit like an EMO. He was rail thin, wore skinny jeans, and kept his hair longer which tended to fall down over one eye. Elite provided a uniform for its employees so that the elite could tell them from their family members, friends, and invited guests at a glance. It was a rather plain affair with a light blue shirt complete with an embroidered first name and a pair of dark blue pants. Shoes were soft-soled and black. In a word, the uniform was...boring. But as long as he got paid, Danny didn't much care.

Well, at least not when he was at work. What he wore was very important to him and it had been for as long as he could remember. Many of those early memories included him wearing his twin sister's things whenever their mother wasn't around. Katie Vance had loved to dress him up and make him pretty and to Danny, it seemed like the most normal thing in the world. As he grew older, he learned just how strongly society frowned on boys who dressed like girls and between that and his mother's occasional comments about her 'other daughter' Danny's embarrassment served to keep his secret hidden from everyone else. As his sister got older, even she grew tired of indulging his special fantasy. She spent less and less time dressing him up and by high school she even began resenting him wearing her things. So he essentially stopped doing it and found some relief in his EMO style of dress. But he never stopped longing to be that pretty girl again. He vowed that one day he would not only have a place of his own, but enough money to buy and wear whatever he wanted whenever he wanted. His dream could wait, but it couldn't wait forever. For today anyway, he was off to work where he would clean the swimming pool of one of the wealthiest men in America on his very first day on the job.

"It's an Olympic," Danny was told. He had a more experienced person with him on his first day to make sure he did everything right and in particular, used the right chemicals in exactly the right amounts. He'd never met this guy before, but the name on his shirt told Danny the man's name was Don.

"Okay, so first we look around for anything that needs to be picked up or cleaned up. And I mean everything. Then you look at the water to see if there's anything in it. And I mean anything. If so, you strain it using this." He handed Danny a long-handled net. "Once everything is spotless, and I mean spotless, then you take care of the chemicals."

Satisfied that the job was done, the trainer took him inside where his mom was busy cleaning and doing laundry. "If you absolutely can't wait, you can come inside and use the bathroom. But don't. Hold it and go somewhere else. I'm only showing you this because I'm required to. Got it?"

Danny nodded but wanted to say, "And you mean absolutely required to show me, right?" but he held his tongue.

Danny had never seen anything like this place. It looked more like a Catholic cathedral in terms of size but without all of the ostentatious ornamentation. Don seemed to have some kind of thing for his mom, who, at 42, was still a nice-looking woman, and he was soon busy trying to chat her up. Anna had stopped what she was doing as soon as she saw him and her son come inside. Danny said hello to his mom and introduced her to Don. Don was so into the conversation with Anna, he didn't notice Danny wandering through the kitchen and down one of the hallways and out of sight.

As he walked, he was amazed by the artwork and other kinds of things which decorated just this one hallway. He passed a room which seemed to be about half the size of his mother's house and noted it was likewise impeccably decorated. As he went passed the next room, he saw a closet that caught his attention.

It never even occurred to him not to go in there let alone that it could get him fired on his first day because he was so enthralled by what he saw. He walked by a massive king-sized bed and stood in front of the huge walk-in closet he'd seen from the hall. "Mr. Regan must have a girlfriend," he thought. The closet was filled with gorgeous clothes of every kind as well as shoes, bags, jewelry, and lingerie. Danny lifted a slinky little dress off the hangar rail and held it up to himself. He noticed it was a size 6 and could tell it would fit him perfectly. He hung it back up then did the same thing to a long, formal gown that was a silky black with a long slit up the side. "This is so pretty," he said as he again held against his body smoothing it out as he turned left then right.

"It's beautiful, isn't it?" he heard a voice behind him say.

Frozen with fear, Danny stood perfectly still.

"Do you like it?" the voice asked.

Danny spun around still holding the dress in front of him. "Oh my God. You're...Mr. Regan. Sir, I'm so sorry. I was just walking down the hall when...."

komrad1156
komrad1156
3,758 Followers