Danielle's Difficulties

Chapter 01 - The Perfect Woman?

I met Danielle a little over a year ago, and quite by chance. We both happened to be the sole occupants of an ophthalmologist's waiting room where, on that particular day, we had both been waiting for an unconscionable amount of time for our respective eye appointments. Apparently, the office's clerical personnel had completely over-booked the doctor's appointments for that morning.

I usually have a very low threshold of tolerance for that kind of incompetence and normally I would have just voted with my feet and walked out--rescheduling my appointment for another day. But, on that particular day, the other impatiently waiting person in the room with me happened to be a stunningly beautiful woman.

She sat directly across the room from me, thumbing through the plethora of outdated fashion magazine issues available for patients--all the while, glancing from her watch to the reception counter. She was dressed impeccably in a cream-colored silk blouse and a navy skirt with her legs crossed--the raised foot constantly moving impatiently.

From my vantage point, I was afforded a particularly revealing view of her legs. But they weren't just nice legs, they were the loveliest, shapeliest legs I had ever seen in my life. As a card-carrying member of the male persuasion, I took particular notice of her legs, watching as she sat, crossed them demurely, or stood to approach the counter to speak with the receptionist. As a result, I couldn't help but feel somewhat disinclined to walk out. Her rather sensual presence in the room at least made the interminable wait one hell of a lot more tolerable.

I had been sitting in the waiting room alone for about twenty minutes when she had first entered, and I was immediately captivated by her beauty. I estimated her to be in her mid-to-late 30s and of medium height, probably no more than five foot five or six, but appeared taller in what had to have been at least four-inch stiletto heels. I watched her surreptitiously as she made her way to the receptionist window, completely mesmerized by her astonishing full figure.

Her fitted skirt and business-like cream-colored blouse did very little to hide a figure that, quite literally, personified the word voluptuous. My eyes were drawn to her wonderfully broad hips as she passed in front of me, her skirt conforming to the delightful curve of her buttocks and plush thighs--and showing off her beautiful shapely legs from a hem that was modestly just above her knees.

I smiled knowingly as she received the same news I had been given about the rather long wait. "An hour?" she protested, her voice rising slightly in indignation. She spoke a little longer to the receptionist her voice lowered. I could only hear an occasional word whenever her voice rose, such as: incompetent, and ridiculous.

I barely kept my eyes on my magazine as she turned and made her way to the seating area, pausing at the table that carried a large selection of well-thumbed magazines and selecting one that--judging by her expression--only marginally interested her.

I watched as she moved through the room, her large breasts shifting beneath her blouse, announcing their presence silently with a profoundly sensual sway. She was remarkably full-figured--in a word, Rubenesque--with a delightfully full bosom and broad hips.

As I was, quite literally, the only other person in the room, there was a veritable plethora of chairs available for her to select. I bit my lip to keep from smiling as she took a seat facing me directly across the narrow room and sat down, crossing her gorgeous legs.

There IS a God, I thought, trying not to grin maniacally as I glanced up to see I was being treated to a rather astonishing view of her thighs beneath her skirt. That she wore no hosiery was wonderfully obvious as the creamy pale skin tone of her legs matched the tone of her arms and her face.

Once I finally managed to tear my eyes from her legs, I looked up to notice how truly beautiful this woman was. Her hair was a soft light blonde hue, falling in soft curls to her shoulders in a style I thought was somewhat reminiscent of Marilyn Monroe. Her skin tone was very pale, almost milky, with light blue/green eyes. Her makeup was done tastefully, with only a hint of eye shadow and mascara. Her lips were full, and she wore a shade of lipstick that, to me, appeared only slightly darker than her lips might normally be. She was either very good at her morning make-up or--I surmised--had been possibly professionally done.

She held her magazine in her left hand, and I couldn't help but notice that she wore no wedding ring. Interesting, I thought. A woman this beautiful without being some rich businessman's trophy wife?

I fantasized absently about possibly attempting to strike up some kind of conversation with her, but in life, I had learned some hard lessons when it came to overly beautiful women.

I had been shot down in flames too many times in my lifetime and knew it was far better to just admit defeat and admire them from afar. To my mind, there has always seemed to be something a little off about very beautiful women.

From the time they are very young girls, they have consistently been told how beautiful they are by family and friends--so many times--they come to believe it themselves. They grow into mature women who, knowing they are very often considered more beautiful than others, tend to wear their beauty like body armor--often with a haughty attitude toward us lesser mortals who might dare to enter their sphere of influence. Jaded and cynical, am I, you say? Sad to say, but true, and I freely admit it.

Over the next thirty minutes or so, she would occasionally stand to return whatever magazine she had been browsing to select another. I watched her surreptitiously as she moved about, and marveled at her voluptuous figure.

Moments later, she tossed her magazine onto the chair beside her with an exasperated sigh. She stood and made her way across the waiting room to the receptionist's counter.

"Is it going to be much longer?" she asked, keeping her voice hushed. "I've been waiting for well over half an hour, and I specifically made an appointment."

"It shouldn't be too much longer, Danielle," responded the receptionist with an air of annoyance on her face. "The doctor will get to you as soon as he can."

Danielle. Discovering her name made me smile. Somehow, that name just seemed to suit her perfectly. She returned to her seat and crossed her legs. I looked up, and we briefly made eye contact. I gave her a half-smile and shrugged my shoulders as if to say, 'Doctors... What can you do?'

"You were already here when I arrived," she said, startling me. "How long have YOU been waiting?"

I looked up and shrugged once more. "I was here about ten minutes before you arrived," I said, trying not to stammer self-consciously as she looked directly into my eyes.

She nodded thoughtfully and leaned forward toward me, "Personally," she began, keeping her voice low and giving the receptionist area a sidelong glance, "I find it completely reprehensible when a doctor's office overbooks and WE, the patients with appointments, are forced to pay the penalty for their incompetence."

"Oh, I couldn't agree more," I returned with a smile, quite literally thrilled with the prospect of striking up a conversation with her.

She looked up into my eyes and smiled. When she did so, her entire face seemed to light up and radiate a warmth that managed to enhance her beauty even more. God, she was beautiful.

Then, to my complete astonishment, she got up and moved to the chair beside mine. As she sat, I was immediately captivated by her lightly perfumed scent--more of a clean, fresh fragrance than many perfumes.

"It would probably serve them right if we just got up and walked out of here," she said, casting another sidelong glance at the receptionist.

"Hey, if you walk out, I'll go along with you," I said with a laugh and tossed my magazine onto the chair beside me.

She beamed another astonishing smile at me, "It certainly would make more of a statement if we both left at the same time, wouldn't it?"

"It would, indeed," I smiled, "And besides, there's a Starbucks down at the ground floor atrium that has been calling out to me from the moment I first saw it," I said, half hoping she might be inclined to have coffee with me.

Her face lit up and she raised her brows, "Oh, my God, I would absolutely KILL for a latte right about now."

"Tell you what," I said with a smile, "Why don't you just allow me to BUY you a latte? I've found that homicide detectives tend to spoil the ambiance in a Starbucks."

She laughed aloud at my little attempt at humor, and once again, her smile lit up her face and made my heart race.

"Let's do it then, let's go," she said as she stood and collected her purse. I could hardly believe my astounding luck. I was about to have the company of this stunning woman for coffee. I stood and held out my arm. She took my arm possessively and we calmly strolled to the office door.

The receptionist looked up with a hint of concern on her face. "I'm sure the doctor will be with you both very soon," she said.

"This gentleman and I are going out for a coffee," said Danielle with a gracious smile. "Hopefully, the doctor won't have to wait TOO long for us to return. If our tardiness becomes too much of an issue for him, perhaps you might then explain to him how your incompetence to book appointments has led to HIS long, inconvenient wait."

With that, we were out the door, giggling like a couple of school kids as the door closed behind us. "We are SO bad," she said with a broad smile. "You realize they'll probably charge us a fee for canceling without notice."

"At this point," I returned, "I couldn't care less. I'll trade having coffee with a beautiful woman over a doctor's appointment any day of the week."

She glanced up at me and smiled somewhat demurely, almost as if being called beautiful was not something she was used to hearing. "Thank you," she said, hugging my arm more firmly against her as we walked.

"I'm Jonathan, by the way," I said, loving how she held onto my arm so possessively. I could feel the swell of her breast pressing against my arm and felt a tingle of excitement as my penis stirred between my legs. "Jon," I added self-consciously, "My friends call me Jon... no 'h'... just J-O-N."

"Nice to meet you, Jon. I'm Danielle," she responded with yet another one of her stellar smiles. "And my friends call me Dani." Even in the elevator down to the ground floor, she kept my arm in her affectionate grasp. Almost astonishingly, we conversed like old friends instead of being relative strangers. It felt so wonderful to be with a woman like her and to feel so completely comfortable. It was unlike anything I had ever experienced before.

We found a reasonably secluded table inside Starbucks and continued our conversation over our lattes--and then second lattes. She was forever laughing and touching me, placing her hand on my hand or my arm while she was speaking, and not once did it feel like flirting. It was just two intimate friends enjoying one another's company.

We talked for hours without even one awkward pause, sharing intimate details about our lives, each of us seemingly completely comfortable doing so with the other. I learned, for instance, how after the death of her parents, when she was fourteen years old, she had been raised by her maternal grandfather, and she currently works for her grandfather's company in an executive capacity.

We laughed and joked and discussed our favorite books and movies. I discovered we had so much in common it astonished me, and she too seemed equally as mystified as we both seemed to have the same taste and interests. The time drifted by completely unnoticed until I happened to glance toward the window to see dusk rapidly approaching.

Seeing my surprised reaction, she suddenly became serious. "Wow... It's getting late, I suppose we should probably leave before the barista has to physically throw us out."

I smiled and leaned back in my chair, hating to think that this wonderful woman I had just met might now walk out of my life. "Here's a thought," I began, "Why don't you let me buy you dinner? I know a great little place just a block away. Do you like Italian food?"

She smiled, taking my hand in hers. "I absolutely adore Italian food," she said, looking into my eyes. "And to be perfectly honest, there's no one I would rather have dinner with tonight. But only on one condition--you have to allow me to buy YOU dinner. You bought coffee; dinner is my treat."

My heart soured. I tried to act casual, as if gorgeous women were always accepting my dinner invitations. But all I could think of was how much I wanted to continue this new and exciting relationship with her. I argued that dinner had been my idea, but she brooked no excuses--it was to be her treat or not at all. I smiled and nodded, thinking she must be a pretty shrewd business executive.

She casually took my arm again as we left Starbucks, strolling down the sidewalk slowly as we continued our conversation, smiling and laughing. I had never in my life felt so completely comfortable with a woman, it was almost as if we had known one another for a very long time.

Passing other people on the sidewalk, I couldn't help but notice how almost every man did an almost comical double-take when they passed Danielle. Often, they would even stop and turn around to watch her as she walked away. I could see quite a few of the passing men look from her to me as if to say, who the hell is THIS guy to be with such a lovely woman? What's HE got?

At the restaurant, we were seated in a very cozy little booth and, as Danielle sat down and scooted toward the middle, her skirt rode up rather high on her thighs, giving me a rather astonishing view of her legs as I scooted in beside her. We both ordered the pasta primavera, and she also ordered a bottle of cabernet--making no attempt to adjust her skirt to a more modest level.

We toasted one another and sipped our wine while waiting for our meals to arrive. "You'll have to excuse me," I said with a little smile. "I can't seem to keep from staring at you. I can honestly say that I have never in my life been out to dinner with such a beautiful woman."

Danielle blushed highly and averted her eyes, "That's... really very sweet of you to say. Thank you." As she spoke, she briefly laid her hand on my thigh. It was only the briefest of touches, but it made my heart race at the inherent intimacy. And, just as we had done in Starbucks, we continued our lively conversation like two old friends who had not seen each other in months, with nary an awkward silence or pregnant pause.

After dinner and settling the bill, we lingered over our wines for another hour, neither of us seemingly willing to end our evening together. "By the lack of a wedding ring on your left hand, I find it completely astonishing that such a beautiful woman is not married or, as you mentioned earlier, isn't even currently in a relationship."

She smiled and dropped her eyes, "Yes... well, being in any kind of physical relationship with someone, or marriage, is a rather complicated issue for me."

"Seriously?" I probed. "What kind of complications are you talking about?"

She reached over and took my hand in hers, smiling sadly. "If you don't mind, I'd rather not talk about that part of myself right now."

"Oh, of course," I smiled, squeezing her hand affectionately. But her reticence certainly gave me pause to wonder what on earth the complications she spoke of might be. Was she ill? Did she have AIDS or something? A variety of scenarios flashed through my mind, but I just smiled and nodded.

Finally, she sighed and, after a glance at her watch, said she should be getting home. "I have to be at the office early tomorrow morning," she explained. A glance at my watch revealed that it was, indeed, almost half past nine.

As we stepped from the restaurant, she reached into her purse and brought out her phone. "I need to call for an UBER," she said. "Will you be kind enough to wait with me until it arrives?"

"Of course," I returned. "Do you live far?"

She nodded, "On the north end of the city near the industrial airport."

My eyes widened as I lived not far from that very airport as well. "I live in the same part of town," I said, "Why don't you let me drive you home instead? My car is in the parkade beside the doctor's office."

She gave me a sidelong glance and a little smile. "I think I'd like that, Jon. As long as it's not too far out of your way." She put her phone away and slipped her arm around mine once more as we began to meander our way back toward the parkade near the doctor's office.

"Besides," I smiled, "It'll give me more time to work up the courage to ask you out again."

She laughed aloud, "You'd need courage to do that? I'd like to think you'd know me well enough by now to know that I would be very happy to go out with you again. I've really enjoyed spending all this time with you tonight."

My heart swelled with pride. Holy shit, I was tempted to pinch myself to make sure I wasn't just dreaming this. "Wow, okay," I said, returning her laugh. "In that case, will you have dinner with me tomorrow night?"

"I would love to," she said flashing me another one of her amazing smiles. "And, once you have dropped me off at my apartment building, you'll know where I live and where to pick me up."

"Perfect," I smiled. "What time shall I pick you up?"

"Well, I usually work 'til five and then it's a twenty-minute commute home. I could probably be ready by six if that works for you."

I nodded, thinking I could probably even leave work early to give myself time to prepare. "I think six is good," I said. "I work until five as well. Where would you like to go tomorrow night?"

"Oh, I'll leave that in your capable hands," she said, squeezing my arm affectionately once more. "I'll be happy to go absolutely anywhere you'd like to take me."

My mind raced. I wanted to take her somewhere special, not just a run-of-the-mill restaurant or dining room. "How about the Moulin Rouge? I've heard really great things about it."

"Oh, my... Are you sure? I hear it's rather fancy... and expensive," she said, turning her head to look into my eyes.

I smiled and nodded. It seemed just the right and perfect place to take such a beautiful woman. And damn the expense, another night with her on my arm would definitely be worth more than the price of dinner and drinks. "Yes," I responded with a smile. "It'll be our first date, so let's do it in style."

"Our first date," she repeated, looking suddenly pensive. "Is that how you want us to think of it?"

"Oh," I stammered, realizing my mistake. "I... didn't mean to presume that it would be anything more than... you know, a dinner date."

"So..." she said, drawing out the word with a hint of a smile at the corners of her mouth, "you're saying I probably shouldn't start mailing out wedding invitations and looking for a white gown?"

I laughed aloud in surprise at her wonderful sense of humor, having just sucked me in with my insecurities. She laughed in return and squeezed my arm affectionately. "Truthfully," she said with a twinkle in her eye, "first date or not, I'm very much looking forward to spending more time with you."

"I feel the same," I smiled, feeling as though I was walking on air. "I'm already looking forward to the Moulin Rouge."

Danielle laughed softly, "Well... in that case, I might need a little more time to dress after work... and beautify myself for such a posh dining room."

I laughed, "Beautify?" I said. "You could wear a frumpy pantsuit and be completely without makeup... and still be the most beautiful woman in the entire dining room."

She laughed aloud. "God, you are so sweet. Where the hell have you been all my life?"

At the parkade, we took the elevator to the third level where I had parked my car. Nothing fancy, a Jeep Cherokee, yet she beamed when she saw it.

"Oh, I love these," she said with a broad smile.

I opened the passenger door for her and shamelessly allowed my eyes to drop to her legs as she slid into the passenger seat. Her skirt rode up very high on her thighs and--Oh God, be still my heart--her legs were absolute feminine perfection.

Leaving the parkade, she reached over to place her hand on my arm. "Thank you for doing this," she said with a smile.

"It's my pleasure," I returned. "But then, how do you know I'm not some sort of serial killer?" I added facetiously with a raised eyebrow.

Danielle laughed aloud, "Now THAT would be impossible," she responded.

"And why is that?" I asked with a curious expression.

"Because..." she replied, turning to look at me directly with one brow raised, "the odds of two serial killers being in the same vehicle at the same time... would be astronomical."

We looked at one another and burst out laughing. God, I loved everything about her, especially her sense of humor.

We chatted comfortably as we drove and, once we entered the northern part of the city, she guided me to her apartment building which, I was pleased to note, was probably only a little over a mile from my own apartment dwelling. I parked in front of her building and turned to her.

"Thank you for tonight, Jon," she said with a sad smile. "I hope this wasn't too far out of your way."

"Not even a little bit," I responded with a broad smile. "My apartment building is only a little ways away on 49th Avenue."

Her eyebrows rose, "49th Avenue? It wouldn't happen to be in the Stratford apartment complex, would it?"

It was my turn to raise my eyebrows, "It is," I responded with surprise, "You know of it?"

"I do," she said with a pleased smile. "The complex is owned by Richardson Investments, my grandfather's company. The company owns this building I live in as well."

I nodded, suitably impressed. Everyone's heard of Richardson Investments, the company controls a great many exclusive business properties in the city.

"You mentioned earlier that you're employed by your grandfather's company--an executive position, I believe you said. What is it that you do there?"

Danielle laughed, "A little of everything, I guess. I was my grandfather's executive secretary until he passed."

She didn't elaborate further, and I didn't press. I could now better understand how she could afford to live in such an upscale apartment building.

"Come closer," I smiled, leaning across the console between us. She smiled and leaned toward me. We kissed just briefly and then kissed again. I loved the sensation of her full lips against mine. She reached up and slipped her hand behind my neck, and we kissed once more, slowly and deeply, lips parting and tongues caressing. She pulled away with a heavy sigh, a little smile on her lips.

"Wow," I said, my lips tingling. "All night, I've been wondering how it might feel to kiss you."

"I'm sorry you waited so long to find out," she returned with a soft laugh. "I wanted to kiss you in the restaurant but was a little afraid you'd think I would be a little too aggressive."

I laughed as well, "If you had... we'd probably still be there in that booth making out right now." We smiled at one another for a moment. "So? Tomorrow night? Six o'clock?"

She nodded, "I'll be ready and waiting." She reached into her purse and took out her phone. "Tell me your number," she said. I gave her my number and a moment later my phone buzzed in my jacket.

"There, now you have my number as well," she said with a smile. "Call me just before you leave your place, and I'll be right here to meet you at the front door."

I nodded and smiled, wishing this particular night didn't have to end so soon.

She gave me a pensive look. "I... would love to invite you inside for a drink... or a coffee, but I just can't... not tonight."

"I understand completely," I said with a smile. "It's a part of the complications you mentioned earlier, right?"

She looked at me thoughtfully. "It is, Jon. It truly is. You're a wonderful, wonderful man, and I already like you more than I probably should. And... the more I like you, the more fearful I am about... telling you more about my complicated life."

"Fearful?" I said, "What on earth is there to be afraid of, Danielle?"

She nodded, "I AM afraid, Jon. Afraid of seeing that look in your eyes."

"What look?" I asked with a confused shake of my head.

"The look that men get in their eyes when they discover the truth about me," she said, looking into my eyes imploringly. "It would absolutely crush me to see that look in your eyes, Jon."

I struggled to imagine what on earth could be so fucking terrible. "Danielle? What the hell is going on with you? I like you too, in fact, I like you very much. I seriously doubt there is ANYTHING you could ever tell me that will change how I feel about you."

To my surprise, her eyes welled, and a tear fell onto her cheek. Holy shit, this was getting weirder by the minute. I leaned over the console and took her in my arms, holding her while she cried. Moments later, she wiped her eyes with a tissue from her purse.

"I'm so sorry," she said, giving me a sad smile that almost broke my heart. "But you're right. It's probably time you know before... well, before you become more involved with me than you already are... without understanding the truth about me."

"Tell me, Danielle," I said, looking into her eyes. "I hope you can trust me enough."

She sighed and leaned back in the seat. "I suppose now is as good a time as any."

"I'm listening," I said.

She took a deep breath and leaned back against the door, facing me. "Thirty-three years ago, my mother gave birth to a son. My parents named him Daniel."

She paused, looking into my eyes. My first thought was that she had a brother named Daniel, and absently wondered if he was an older brother, or younger. My second thought was that her parents weren't all that great at naming conventions. "An older brother, or younger?" I asked.

She shook her head and her eyes welled once more. "Neither," she said softly with a little shake of her head. "Daniel was... their only child."

At first, it confused me--only child?--and then the implication hit me like a jolt of electricity--Daniel/Danielle--The gorgeous, stunningly beautiful woman beside me was male at birth. She was transgender. "Oh," I managed to stammer.

Her shoulders sagged and she nodded, biting her lip. "And there it is... the look I hoped I would never see in your eyes."

Before I could manage to stammer out another word, she turned and opened the door.

"Wait," I gasped, my mind in complete turmoil as she stepped out of the car and closed the door behind her.

She bent down and looked at me through the window as she closed the door, and I quickly lowered the window. "Danielle, wait."

"You have my number," she said as another tear tracked down her cheek. "If you want to cancel dinner tomorrow night, I will understand completely."

With that, she turned away and walked to the front door of her apartment complex.

(The story will continue in Danielle's Difficulties Ch. 02)

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Author's note

Thank you for taking the time to read my story, I can only hope you have enjoyed Chapter 1 of Danielle's story. Chapter 2 will be forthcoming soon. I value your comments, feedback, and suggestions tremendously, please feel free to add yours in the comments section, or via email. If you'd like to stay connected and follow along with my newest stories and updates, be sure to follow me here in Literotica. Thank you all for your kind words of encouragement.

Jaymie_dee