Danielle's Difficulties Ch. 02

Chapter 02 - Heartfelt Confessions

I sat in my car, completely dumbfounded. She was a man? Danielle was a MAN? Strictly speaking, though, she was only BORN male--a technicality I was doing my best to cling to. It seemed completely ludicrous to even conceive of such a thing. I had spent the better part of an entire day with her--and not ONCE did I get even the slightest inkling of an impression that she was anything other than a woman. I had seen transgender women occasionally on various porn sites and, to my mind, very few could pass for real women. Men typically had heavier muscle tone and bone structures, thicker knees, and masculine jawlines--attributes that made it prohibitively problematic for them to pass as women--Danielle had NONE of those typical male attributes; even her voice was soft and feminine.

I sped away from the curb, my tires squealing as my mind reeled. I headed nowhere... just driving.

I drove in circles over a ten-block radius, passing her apartment building at least a dozen times while I tried desperately to come to terms with the reality of Danielle's sexuality. Eventually, I managed to find at least some measure of resolution in my mind and eventually pulled to a stop once again at the curb in front of her building.

I got out of the car and paced back and forth in front of her building for several minutes, looking up at the windows and wondering if one of them might be hers. Suddenly, I was struck with a revelation. My every reflection of Danielle was as HER and SHE. She may very well have been born male, but the incredible person I had just spent the entire afternoon and evening with was, without a doubt, a woman--in almost every way.

I sat on the step in front of her apartment building door and took out my cell phone. I found her number in my list of missed calls and pressed call. Her phone rang only once before she answered.

"Jon?" she said, her voice strained as if she had been crying.

"It's me, Danielle," I responded. "Don't hang up... please don't hang up."

"I won't Jon... I'm here," she said. "Are you all right?"

"Listen, Danielle, I get it. I understand now what you meant by your complications. And it absolutely breaks my heart to think you saw something in my eyes... that made you think less of me. Believe me when I tell you, Danielle, if I had any kind of look at all, it was honestly nothing more than a look of surprise and astonishment. I care about you very much, Danielle. Can we please discuss this whole issue sometime... I don't want to leave things the way they were when you got out of the car... Danielle?"

She was silent, and for a moment, I thought I might have lost her completely. The door behind me buzzed and opened, and thinking someone was about to exit, I quickly stood and stepped out of the way. When I turned, I gasped to see Danielle standing in the open doorway.

"Hang up the phone, Jon," she said, tears streaming down her face. "I care about you too. Please... come inside so we can talk more privately."

I stepped closer to her, and she held her arms out to me. We embraced warmly, our bodies pressed tightly together. I tentatively kissed her lips and she responded, parting her lips invitingly--a soft sound emanated from her throat as our mouths opened, and her tongue found mine.

I have no memory of how long our kiss lasted, only that I never wanted it to end. She wore a pink knee-length satin robe and, as my hands moved over her back, I was acutely aware of the fact she wore no bra beneath it--her soft, full bosom swelling against my chest.

She pulled away, looking into my eyes. "Maybe... we should go inside," she said, looking around self-consciously. "And you're right, we need to have a heart-to-heart discussion."

She took my hand and led me to the elevator. We stepped inside, and she pressed the button for the top floor. We rode in silence, her hand in mine, smiling somewhat shyly. She led me to her apartment--APARTMENT?--It was a freaking penthouse suite. I gazed in open-mouthed astonishment to see it was spacious and opulently appointed with designer furnishings. The broad living room window did, indeed, face the street in front of the building.

This had to be the largest and most expensive dwelling in the entire building, and it had my mind reeling all over again--who WAS this woman?"

She led me to her sofa, and we sat down together, our hands entwined. I kept my eyes on hers but was acutely aware of how her short robe bared a great deal of her gorgeous legs.

"First of all, Jon, I need to know that you are all right," she said, wiping her eyes.

I nodded, somewhat overwhelmed by the opulence of her suite, as well as my feelings for her.

"I sat right here," she continued with a wistful smile, pointing to her front window, "and watched as you drove around, again and again, in front of my building. I most certainly understood the conflicting thoughts that must have been going through your mind out there, and my heart went out to you. I cried each time you drove by and--each time you passed, I hoped you would drive by again... and eventually would decide to stop."

I nodded and felt my own eyes welling at the sorrowful sincerity in her voice. As I was about to speak, she raised her hand, showing me a glass that contained ice and an amber liquid. "Mine is scotch, but I have a full bar. Can I offer you something?"

I nodded, thinking a drink was exactly what I needed at that moment--to fortify my resolve and somehow find the words to express my feelings cogently. "Scotch sounds perfect," I responded.

I watched her as she rose and made her way to the bar, eyeing the back of her satin robe shamelessly as it formed so provocatively around her plushly rounded buttocks. Her body was absolute feminine perfection, and it still seemed inconceivable to imagine she had been born male.

Using silver tongs, she filled a glass with ice from a crystal ice container, and poured me a drink--my eyes widened in surprise to note she poured from a bottle of Johnnie Walker Blue Label. From her penthouse suite to her extremely expensive choice of Scotch, Danielle was, to my continuing astonishment, a more affluent woman than I had ever imagined.

She returned with my drink, a rather generous amount of scotch on ice. As she approached, her breasts swayed provocatively beneath her robe, and I could distinctly see her nipples peaking the satin material. We raised our glasses, clinking them together, and then sipped. The scotch was excellent, and so smooth it made me smile.

"So," said Danielle, smiling at me as she crossed her legs. "I'm sincerely hoping you haven't come by to cancel our dinner date tomorrow night."

"No," I responded with a laugh and a shake of my head. "On the contrary, while I was out driving around aimlessly, I phoned the Moulin Rouge and made a reservation for two for tomorrow at six-thirty. Is that still all right with you?"

Danielle's face beamed, and she smiled coquettishly. "Of course," she said as she sipped from her glass and eyed me demurely. "I'm very much looking forward to dinner with you, Jon. Should I take that to mean that you've made a personal decision regarding my physical complications?"

I nodded. "I guess I have, yes," I said, looking into her eyes. "When you told me you were born Daniel, it took me completely by surprise. And, if you thought the look you saw in my eyes was, in any way, more than just surprise, then I truly and humbly apologize."

"Oh, Jon... you have absolutely nothing to apologize for. Your reaction was completely understandable. I'm afraid my reaction was... somewhat less than stellar--a likely result of my entire life of personal insecurities--that led me to believe the look in your eyes might have been something other than surprise."

I nodded, thinking she hadn't really given me much of a chance to process her surprising information before making her decision to get out of the car.

"Listen, Danielle, I'll honestly admit that, after I drove off and had a few moments to think about it, I DID have some serious personal issues. I mean... I've never been a homophobic person, nor have I ever been sexually attracted to men. But even knowing the truth about your gender at birth, I couldn't deny the feelings I have for you--regardless of birth gender. I realized I just couldn't let that slip away. You're not like any other woman I've ever met, Danielle, transgender or otherwise. There isn't even the slightest hint of masculinity about you... Not one. I look at you now and all I see is the most beautiful woman I have ever seen in my entire life."

Her eyes welled and tears flowed down her cheeks. "Thank you," she said, her voice husky with emotion. "It means a lot to hear you say that. I have had the good fortune to have had an extremely rich grandfather who adored and spoiled me from the time I was a young girl. What you see when you look at me is the product of countless surgeries, the best that money can buy."

I nodded and sipped my drink. "When... when did you first realize... you know..."

"That I was a woman trapped inside a man's body?" she said, finishing my stammered question with a smile.

When I nodded, she continued. "There was no sudden lightning bolt out of the blue realization. In my heart, I think I always knew there was something wrong. Even as a child, I had little interest in the boy toys and Christmas gifts I was given--guns and trucks and such. When I tried to relate my feelings to my parents, their right-wing Christian fundamentalist beliefs wouldn't allow them to even begin to accept and understand. They thought of me as..." she paused as her eyes welled once more, "an abomination."

"Oh, my God," I gasped, reaching out to take her into an embrace.

Danielle cried on my shoulder for several minutes and then talked for almost an hour--refilling our drink glasses along the way--explaining the difficulties she had experienced in her formative years.

Her maternal grandfather had been horrified by the way her parents reacted to her revelation. Much to their relief--and hers--he had physically taken her away from them and raised her on his own from the time she was twelve.

They had long talks, and he understood her dilemma. He encouraged her feminine feelings, allowing her to express those feelings by growing her hair long and wearing dresses if she wished--and she took great pleasure in doing so. He hired professional tutors to educate her at home and leave behind all of the racist, homophobic peer pressure she was likely to experience by attending school as her chosen female gender.

Scholastically, she excelled, officially graduating from high school at the age of sixteen. Her grandfather then began to tutor her for a position in his company. She learned accounting and business communication, as well as the investment and real estate markets. She absorbed all things business like a sponge, progressing even beyond her grandfather's expectations.

More importantly, her grandfather took special care to provide for her medical care, enabling her to transition physically as well as emotionally. It began with a series of facial operations to remove any vestiges of being male--re-sculpting her cheekbones and chin for a more feminine look.

The bones and muscles of her arms and legs were painstakingly sculpted and reworked through several different operations to give her a more feminine appearance, as were the many breast enhancements.

In total, there were dozens of body sculpting operations, as well as a plethora of plastic surgeries to cover any scarring. Culminating in a series of collagen injections to give her plush feminine hips, buttocks, and thighs.

I could only shake my head in wonder at what must have been an extremely difficult and painstaking process.

"My God, Danielle, that can't have been easy for you," I said in awe.

She shook her head and smiled, "God, Jon, you have NO idea. There were times when I just wanted to scream. As soon as I recovered from one operation... it was time for the next. I quite literally had no childhood. To this day, I hope I never see the inside of another operating room."

"How many years?" I asked, squeezing her hand affectionately.

She raised her eyes to the ceiling thoughtfully, "Let's see... from the age of 14 til I was 25."

"Over a decade," I gasped in wonder. "If it's any consolation, the work you had done was astonishingly remarkable. You're a stunning woman, Danielle."

"Thank you," she smiled gratefully, "the best my grandfather's money could buy."

"Did you ever want to just give it up?" I asked.

"Only two or three times a day," she said with a hearty laugh. "My grandfather and I would have long serious talks on the subject. And... for as much as I disliked the difficult process... I SO wanted to look like the woman I always felt I was."

She paused as she refilled both of our glasses. "My grandfather said he had seen photographs of other transgender women and had been appalled. He vowed that I would never have to go through the ignominy of resembling a man trying to look like a woman, and he spared no expense on my behalf. In total, I believe he must have spent well over a million dollars on all my surgeries and body sculpting over the years."

"About all of those surgeries," I asked, "May I ask a very personal question?"

Danielle laughed softly and nodded, "If you're wondering about the extent of my surgeries, yes... I still have my penis."

We both laughed and she continued, "I could see the curiosity written all over your face," she said with a broad smile. "Although, my penis is really rather small." She held up her thumb and forefinger to indicate a length of about two inches and laughed softly.

"Can you... um..." I stammered.

"Get an erection?" she answered, once more correctly intuiting my question, "I can, yes. Again, it's also small... maybe all of four inches when I'm fully erect. I can even ejaculate when having an orgasm."

She paused, looking thoughtful for a moment. "Just so you know, I have no scrotum or testicles," she said, "at least not visibly. My grandfather thought it best to keep my testicles--having them surgically implanted into my body in case I ever wanted to father a child at some point in my life."

"Holy shit," I said breathlessly. "That must have been an endeavor and a half."

Danielle laughed aloud and shook her head, "Oh, my God, yes. That entire process took almost two years to complete... and it was extremely uncomfortable as well."

"But, all is well with you now?" I asked looking hopeful.

"Yes," she said, raising her glass in a toast, "Thanks to God... and my grandfather."

"Do you mind if I ask you about your love life?" I queried. "I mean... you must have had... well... significant others from time to time as you transitioned?"

Danielle laughed and sipped her drink.

"Yes, I've briefly had significant others in my life--although their significance is surely a matter for debate. My grandfather hired a sex education psychologist--a very nice woman named Lillian Osgood--who hoped to ascertain my emotional level of attraction to either sex. You know... if I was born male, was I still somehow psychologically attracted to women? Or, as a woman was I psychologically attracted to men?"

I nodded, it made perfect sense to me.

"In that regard, when I reached the age of consent, grandad hired two private escorts to... initiate me sexually--a woman and a man."

"Wow," I said, "How did that work out?"

Danielle held out her hand, palm down, and waved it back and forth to indicate so/so.

"The woman... whose name was Margaret, deflowered my male virginity, and it was a lovely experience--but it was just sex for the sake of having sex, there was never an emotional involvement for either of us--and also a little heartbreaking to know I could never be a woman like Margaret... because I had no vagina."

She shrugged and sipped her drink.

"The man... I think his name was Alex, played the dominant role to my femininity. He initiated me into anal sex--giving and receiving. Also very pleasurable most of the time--I discovered I like anal sex very much--but it was still just sex for the sake of having sex, with no emotional involvement."

"You never got to fall in love?" I asked, feeling sad for her.

Danielle laughed and tossed her hair, "Oh, hell YES I fell in love. Bobby Ramirez." She sighed wistfully, "He worked in the company's accounting department. He was gorgeous, like a male fashion model. Even though I was well beyond my teens, he was my first crush."

I sighed, great... how could I ever compete with that kind of male pulchritude?

"And he understood me," she continued, "he was the first male who ever learned about me being transgender without running away and vomiting. I was SO in love with him."

She finished the scotch in her glass and stood, taking up my glass to refill each one before returning to the sofa.

"When Bobby broke up with me, it devastated me, he SO broke my heart. He let me know, in no uncertain terms, that the only reason he was interested in me at all... was because he wanted to be able to brag about how he had fucked a TRANNY."

"What?" I gasped horrified, "If that son of a bitch was here right now, I'd kick his balls up into his throat."

Danielle laughed, "Thank you for putting that image in my head," she said. "I believe I wanted to do something very similar at the time. My grandfather, however, had an even better solution: he had Bobby transferred to the company's office in Fairbanks, Alaska."

I laughed aloud. "I'm sorry," I said, "But I think I like your grandfather even more for coming up with that solution."

Danielle raised her glass to me, "Thanks, Jon. It's water under the bridge now... but I do appreciate your sentiment."

I raised my glass with a smile.

"I haven't asked you about your feelings," she said, giving me a more serious look. "And I can't help but wonder what your feelings might be about me now... after everything I've just told you."

I nodded. She was right, she deserved to know what my feelings were--I just wasn't all that sure I would be able to articulate them adequately--especially after several glasses of scotch.

I looked up into her wide, appealing eyes and took a deep breath. "I'm not exactly sure how to even begin. Maybe I should just start by saying that I believe I have fallen in love with you, Danielle."

Her eyes widened perceptibly, and the corners of her mouth hinted at a smile.

"I know," I continued with a shake of my head, "I've only known you for less than a day... but, damn it, Danielle... I've NEVER felt so comfortable with a woman in my entire life. We share the same interests in books, movies, and music... and we even have the same quirky sense of humor. You are, without a doubt, the most wonderful woman I've ever met."

I paused to sip my drink. "And, when I say woman, Danielle, I mean woman. You may not have a vagina and ovaries, but to me, you are ALL woman."

"Thank you," she said, her eyes misting.

"I don't pretend to know how it would work," I continued, "or even if it COULD work out between us. But I would sure love to have the opportunity to explore the chance of a deeper relationship with you."

"Jon," she said softly as she wiped the moisture from her eyes. "I'm sure you must know by now that I have very strong feelings for you too. When it comes to having a chance for a deeper relationship with you... you had my heart the moment you stopped driving around in circles and parked in front of my building tonight."

She opened her arms to me, and we embraced warmly, her scent permeating my senses. We kissed briefly but very sensually before she pulled away.

"I think perhaps we should leave things where they are for tonight, Jon," she said. "As I said earlier, I have an early business appointment tomorrow morning and need my rest... especially after the wonderful day I've had with you."

I nodded. We had said all that needed to be said, tomorrow was another day. "So... we're still on for dinner tomorrow night?"

"Oh, Jon, I wouldn't miss it for the world," she said.

She walked me to her door, and we embraced and kissed once more. Her body molded into mine as we kissed. On the elevator ride to the first floor, I smiled broadly. As she and I had kissed, I was reasonably sure I briefly felt a light press of what might have been a small erection against my thigh.

(The story continues in Danielle's Difficulties - Chapter 03)

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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 2 of Danielle's story. Chapter 3 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