tagTranssexuals & CrossdressersResults and Consequences

Results and Consequences

byFred190666©

Notes from the author: Hi again everyone. First of all, I wish to thank those who encourage me to keep on writing. No matter how modest one claims to be, it is always gratifying to read such praise. Second, because I don't want to revisit a theme when I write, this is probably the last story where I will be able to draw upon personal experience or memories to ground the fantasy. This will be a sort of teacher's pet story... of course, since I am the author, you know it will be corny and with a happy ending, hi hi! After that one, who knows... do you have suggestions? Anyway, as always, I hope you have a pleasant and rewarding read.

P.S.: Contrary to my earlier "infatuation" storylines, in this story the relationship lingers somewhat. As a result, this is one of my longer stories. You have been warned! :)

1. The first date

"Am I really doing this? God, I feel pathetic..."

It was in this anxious and depressed mood that Gerald Anderson was thinking out loud in front of his hotel room's mirror, looking dejectedly at himself. The reflection was not the problem: as a private practice lawyer, he knew the value of a professional appearance and as a student who had earned a varsity letter in crew, he had the wisdom and discipline to keep fit. As he also believed in quality over quantity, he had decided tonight was worthy of wearing one of his Italian silk dinner jackets... no one had ever spent enough time with him to realize he owned only two of them.

So, the reflection was not the problem; in fact, Gerald was a striking 28 years-old young man endowed with a tall, strong, springy grace; his deep-set and expressive green eyes emphasized his natural empathy; no, tonight, the problem lay in the uncertainty and shame he felt for what was about to happen. The shame both for his appraisal of the morality of his future actions and also for denying to himself that he was excited about them all the same. When he couldn't bear watching himself anymore, he left his room and headed for the elevator.

Gerald walked about in the elegant lobby of the Hotel Lafayette and stopped dead in his tracks in front of the doorway of the Lafayette Brewing Co. restaurant. He immediately recognized his date for the evening, an exceptionally beautiful young woman, barely an adult, whose appearance for tonight traded erotic for elegance. In her short heels, she was just as tall as he - so around 5ft. 10in. - and she wore her jacket and skirt ensemble to perfection. Her shirt was opened enough to be enticing without being revealing, her makeup, glasses, hairstyle and jewelry were a symphony a good taste... in short, the two of them looked more like a legal team about to plead a case than a couple on a first date.

(Wow! There she is... no turning back now... let's go Gerry.)

Gerald was both terrified and completely hooked. He summoned his courage and walked up to her.

"Dana?"

She turned her lovely head and her hazel eyes sparkled upon recognizing him, like he was the most welcome sight in the universe. Gerald stopped breathing and he could swear he saw the swivel of her long golden-blonde hair in slow motion. He was mesmerized.

"Gerald! It is you! And, I must say... wow! Your picture does not do you justice: in fact, you don't look like a Gerald at all! Can I please call you Gerry?" He had offered a handshake, which she promptly set aside for two very decorous and expressive kisses on the cheeks.

"Ha! That makes you a woman after my dad's heart! Sure you can!" Dana was surprised by the booming, cheerful and hearty voice, which ill-fitted the sophisticated look of her date.

"Why do you say that, Gerry?"

"Because Dad was a HUMONGOUS fan of Supermarionation! In fact, when I was still a kid and he was 45 years old, we watched together ALL the original Thunderbirds episodes, and he was involved and full of researched lore! And I have an older sister so, of course, I'm Gerry and she's Sylvia Anderson. But I suggest we go inside, before I start my own geeky rant about the Thunderbird 2 take-off sequence and you run away!"

"Not a chance, Gerry... but I am hungry, so yes... let's please go in." She was perplexed and amused; she would look up the topic later.

They were both seated at their reserved table, far from the "bar-cade" as requested. That caught Dana's attention and, when she asked about it, got Gerald to laugh, and again its sound was hearty and warm. "Forgive me; I took for granted you would not be the type to play pinball or shuffleboard!"

Dana was a little unsettled, and her own smile dimmed somewhat. "Gerry... it's your date... we can do what you want... really."

Her awkwardness proved to be contagious. "Right... of course... I'm sorry, Dana, I've never done this before. Here... I believe this is what we agreed upon." He was blushing deep-red, his voice had a shameful tone and he handed her discreetly an envelope; it was thick and laden with a thousand dollars, which Dana counted and placed in her purse. She then, silently and efficiently, produced a receipt and handed it to him.

"Thank you Gerry. Is it your first time here too?" He nodded in agreement. "Same for me. And it looks like a great choice, so can we please return to enjoying ourselves?"

They were thankfully interrupted by the waiter, and Gerald would have kissed him for it. "Dana, do we indulge in wine or do we sample the local beer?"

"Beer is fine with me... I would like a Rough Rider Robust Porter please." Gerald raised an eyebrow but perused quickly over the menu and ordered a Roosevelt Red for himself.

"YOU, Dana, are a young woman of surprises and mysteries... and a very convincing liar... I will have to keep my eye on you!" Gerald said so in a mocking tone, but it was evidently heartfelt.

"And why would you say that, Gerry?"

"You obviously enjoy pinball and shuffleboard, you have enough beauty to induce a heart attack and enough class to belong in an executive boardroom if you wish, you have enough poise and presence to belie your age, you know your dark beer and have obviously been here before."

Dana felt both flattered and a little hurt. "Yes... you're right. I'm sorry. I play the innocent card sometimes, to reassure insecure dates. I will say though, in my defense, that you're not quite as I expected and I am struggling to get a handle on your expectations; I know it's not very professional on my part, but can we play our game with an open hand for just a minute, please?" That candor caught Gerald off guard.

"Very well... you start and I follow your lead."

"You hired me, Gerry. Dana Deep, transgender escort, fully functional and first-class all the way. It's obviously your first time at this. You clearly don't want your ego stroked and I don't see any peers to impress. Yet, we're not already naked in your room, so it's not all about my tits-and-dick either. Have I got something wrong so far?" Gerald was transfixed but, for some strange reason, also relieved.

"No Dana. You really are first-class. Yes, I hired you. For me and me alone. And - the fact that you dazzle me notwithstanding - I'm absolutely not proud of it."

After a short pause to collect his thoughts, he carried on. "You should know about me that, almost right after I started my practice, I had to become the live-in caretaker of my ailing dad, which pretty much stunted my social life for some years. During the lonely nights, I eventually streamed porn videos online; and the shemale - I know the term is improper but it is what it is - the shemale category became a recurrent source of arousal for me. And that planted something in me... I don't know what it is but it's powerful enough to impact my recent dating attempts after dad passed away. So I have to know: call it self-discovery, call it curiosity. But how do you approach an unknown woman when your prime interest is a research project in her anatomy? So I... huh... altered my searching strategy... and as soon as I saw your site, I knew it HAD to be you. You had me captivated on the spot. I want you, Dana; but I also need a date. I want to know you before I get to know you biblically. And I want both of us to enjoy this... this very short-term couple of ours."

He didn't see her heart flutter; she really was good at this.

"My condolences for your loss... and I suppose your mother is also gone?"

"Lung cancer... I was still young when that happened."

"You do understand this is not Pretty Woman, right? I am not to be saved and there is no ever after for us."

"The thought had never crossed my mind, Dana... the saving you part, at least. You are obviously focused and in control of your life. I have neither clue to your motives nor any right to judge them. If I had to venture a guess, I would say you're currently in college, getting ready, quite on your own, for something better."

"Touche, Gerry. Junior BFA communication design. And your moral stance does your ethics lecturer position proud."

"You know about..."

"Of course I do... I always screen my first-timers beforehand. I congratulate you for your online discretion, but your website could really use some vamping up. Anyway, since we're talking about ourselves, could you please tell me what a probate lawyer is?"

"Probate law is the practice surrounding the recognition of wills and the management of estates, Dana."

"Again, not what I expected... you should give Mickey Haller a run for his money instead... you could be a hunk seducing juries with these eyes of yours; but let ME guess now: your mom or dad had succession problems?"

"Indeed... I'll spare you the legalese so, in short, Mom went to Heaven and Dad went through Hell and back right afterwards. Granted, probate law and its jurisprudence are not very appealing at face value, but most cases are poignant, with clients at their most vulnerable - a little like me right now - and the dramas I live do not require a courtroom novel villain. That sits very well with me. On the other hand, you, young lady, have a truly bang-up website... do you want me to send a reference to your teacher for extra credit?"

(What the f... less than 30 minutes with me and he's trading quips!)

For once, Dana was the one blushing and destabilized. "No thank you, smartass... you DO realize it's not Dana Deep that studies at SUNY Buffalo State?"

"To the titanic regret of the fraternity houses I'm sure! Now, since you've already been here, do you think the two of us sharing a large BBQ chicken pizza is a good idea?" Gerald was noticing the waiter coming in with their beer.

"Yummy! Gerry, you read my mind!!!"

"For real? You're not just trying to please?"

"For real, Gerry... look, I got your point and for you, tonight, it's as you wish: a one-night couple with no bullshit, OK? What you see is what you get!"

"Super! And, in case I forget, thank you in advance for a lovely evening... because if I do get all that I'm seeing, I might not be coherent by the time the carriage reverts to a pumpkin."

(Cut it out, Gerry! This is not a fairy tale... please don't get hurt...)

"Enough flirting before the meal, sir... please order and propose a toast."

After the order, Gerald gave it a thought and raised his glass. "To us, for tonight!"

"Cheers!" After her sip, she added "...a very good and appropriate toast!"

From then on, it was all joy. They enjoyed their beer, they enjoyed their meal, they enjoyed getting to know one another - albeit superficially for the Dana persona, of course - they also enjoyed sharing a French onion soup after the pizza, feeding themselves spoonfuls and making a mess with the melted cheese.

"Gerry, thank you... the meal was absolutely great! Now, I'm very sorry, but addiction calls... do you want to stick with me while I smoke one outside or do you wait for me here?"

"I'm right behind you; right after I settle the check."

She was in the process of lighting up when he joined her. Gerald noticed her brand of Natural American Spirit cigarettes and chuckled. "You know, smoking organic tobacco does not make it safer."

She looked at him irked, but only saw a good-natured smiling face that just couldn't be any less judgmental or condescending. He was really something else. "I know, Gerry... it says so on the label." But she was still trying to decipher his look, as he just stood there and watched her quietly while she smoked outside of their venue; she was sure it was regret.

"Look, Gerry, thank you for your effort in not judging... I mean, I know, it's a disgusting habit and all, but... well... I don't want to stop. I figure if I don't die from smoking, I will have died of something else beforehand..." Dana delivered her well-rehearsed and often-used litany but suddenly felt like an ass doing it. "... but... huh... I don't suppose your mother's lung cancer came from asbestos?"

Gerald had a benevolent and forgiving smile. "No, you guessed right... mom was a heavy smoker right to her last breath; and she told me the only times she ever tried to quit - emphasis on tried - were during her pregnancies. But what also saddens me is that you have dismissed a very valid ethical conundrum about self-determination with a self-evident postulate." Again, a chuckle.

"But of course! What was I thinking? I apologize if my smoking gets in the way of properly resolving an ethical conundrum!" Now he laughed. And she felt good about it.

"You're not supposed to resolve it, Dana... that's why it's called a conundrum."

"God help me, I sense a lecture coming... what do you do if you don't resolve it?"

"The trailer version of the lecture only, promised. You do your best, basically: you figure your motivations, ponder the expected results with your moral standards, you make an imperfect choice and live with the consequences."

"Wow! Free ethical advice from a pro... thank you!" True, Dana had a knack for repartee that made her always seem in command of the situation, but this date was truly becoming out of the ordinary. She was involved in the banter, not regurgitating one or the other of her client conversation protocols. Standing there with him outside was effortless, even though the fall evening air was cold and she had already finished her cigarette. Even more gratifying, she was sure Gerry felt the very same way, completely oblivious to the passing time or the pecuniary nature of their encounter.

She started chewing a piece of gum and felt compelled to explain. "Bubble-gum flavor, Gerry... the best for masking odor, according to my dad who's in waste management."

"And she's also a pro at masking odors... there are truly no limits to your talents, young lady. Tell you what then: why don't I let you beat the crap out of me in the bar-cade?"

"Thanks Gerry! That would be great! Lead the way!" Despite the fact that limits in Dana's talents were embarrassingly revealed while playing shuffleboard and several pinball machines, that playful time was a delightful addition to their joy together.

After another humiliating defeat, Dana hugged Gerald closely for mock comfort... only to remain there long enough to feel sincerity and emotion in their closeness. "Gerryyy, why don't we go up to your room?" Her voice had morphed in such a sultry and alluring low tone that Gerald was startled. He silently agreed and they both walked out of the restaurant clinging to one another.

She could hear his heavy breathing while they were in the elevator. "Gerry, are you OK? You don't sound too good..."

Gerald smiled meekly. "I guess that, no matter how wonderful our date is so far, I still feel nervous about... you know..."

She gave him a quick kiss on the cheek. "Just relax, Gerry... look, do I excite you?"

"You know you do, Dana. For one thing, I chose you. Plus, you're even more a knockout than I expected. And to top it all off, you're super-fun to hang around with. So yes, Dana, you excite me... quite a bit."

She took his hand and placed it on the barely concealed bulge between her legs. "Now feel me, Gerry. You're a great guy, you're sexy as hell and you turn me on. I can't fake this. We are about to have a wonderful time together, all right?" The elevator doors opened, forcing the end of her hands-on pep talk.

They walked casually, hand in hand, toward his room. As she felt him balking at opening the door, she gave him a soft kiss on his lips to urge him inside. Once in the small atrium, he returned the kiss with an intensity that startled her. His lips were moist and extremely soft. And they were channeling heartfelt emotions.

(Dammit! Don't fall for me, Gerry!)

It was no use... Dana was won over by their kiss and got into it, probing his tongue with her own and signaling her own arousal. She ended the kiss before losing herself in it and asked, in a formal tone to regain control, if she should undress. She literally saw his heart bursting as he silently acquiesced.

It was not as lurid as a strip-tease... but it was more tantalizing than a wardrobe change. Dana slowly removed her jacket, her skirt, her shirt, her glasses and, after some hesitation, even her wig. The result was nothing short of a metamorphosis. Dana was now clad in black sheer lace lingerie and sported a short, wild, chestnut brown haircut. She did not revamp her makeup and looked up to Gerald, expectantly, before very slowly removing her panties and setting her penis free. It was already hard and ridged with gorged veins.

He took in the sight of her: the slender legs and neck, the shaved erection, the thin hourglass figure, the pert breasts, the self-assured poise. She was inviting and forbidden at the same time. But so amazingly beautiful. "Well, Gerry... just as promised, this is me without bullshit. I am 22 years old, I am healthy and I always perform safe sex. Do I still turn you on, lover?"

"Oh God yes! Dana, you're so hot it almost hurts just to look at you. May I caress you, please?"

"You're still quite overdressed to cross that line, Gerry." She said it tenderly, still intent on reassuring and calming her client. And she never let go of his gaze while he removed his jacket and the rest of his clothing, with clinical efficiency. She was pleasantly surprised by the bulge straining his briefs and lusted for the moment he would reveal his own family jewels. Not that she had to wait long for it. She gasped at the sight of his penis, a large, thick, hard, pale and uncircumcised rod. In fact, it was so hard by now that the prepuce was pulled back, exposing a pink bulbous gland that was already moist to a shine with precum.

More tantalizing to her was the fact that this hardness was matched by the one of his buttocks and groins, strong and lean. "Wow! Gerry, you are blessed and I am going to enjoy you!"

"I bet you say that to all the guys... and probably girls."

(Shit...)

"Well... as a matter of fact I do. But I intend to show quite clearly that I mean it, Gerry... now tell me: what do you want to experience with me? Are you a virgin?"

"With a woman like you, absolutely... and I wish to do it all, Dana: caress you, suck you, penetrate you. I also want you to penetrate me and I do hope I will be good enough for you to enjoy it."

"I am sure you will be. You can caress me now, Gerry..."

Gerald placed himself behind Dana, and gently let his hands discover her shoulders while kissing the back of her neck. She could also feel him deeply inhaling her aroma - a mixture of vanilla lavender perfume and bubble gum breath. He was worshiping her so much she almost felt the need to remind him she was a sure thing... but that would be denying that she did enjoy his pampering.

Gerald was focused both on listening to her relaxed breathing and on feeling the tingle in his fingertips from wandering all along the velvety smoothness of her arms and shoulders. He was now more relaxed and was tightly spooning her. She felt his chest on her back and the pressure of his erection on her tushy... and relished it.

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