Big Flipping Deal Ch. 01

[Author's note: This is the longest thing I've posted to Literotica yet, 60,000 words that I'll be dividing into 7 or 8 chapters. It's also got the lowest proportion of sex scenes in any of my serials. I very nearly put it in the "Romance" category, because it's as much or more a love story as a work of erotica. But I figured fewer of the readers in that category would be interested because of the transgender element. So if you're looking for something like "Contrast" or "Gloria's Daughter" where the majority of scenes are packed with fucking, this one may not be the story for you, or you may want to skip directly to the last chapter where there's a little more naughtiness as a payoff. As usual, I'd like to thank DonnaBeck for her advice and encouragement as my beta reader, and I'd like to thank everyone else for being readers in general. I hope you enjoy this one ... I'm pretty happy with it.]

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I certainly didn't go into the reading of Mrs. Pinobscott's will thinking I might score with a trouser-burstingly hot blonde in a microdress and black calf-length stiletto boots. I mean, maybe I had some fantasies about Mrs. P's lawyer being a vision in heels and a too-tight suit skirt. And maybe I daydreamed the old lady would leave me a mint so I could cash in on some gold-digger action and improve my sex life.

But realistically what I expected to get was her cat. So when I walked into the law offices of Donovan, Donovan and Furnier, the only pussy on my mind had claws and hairballs.

The receptionist who greeted me in the front office had a nice smile, too many freckles, and a wedding ring. Her outfit would best be called "frumpy." And when she led me down the hall, there were no sizzling young interns or professionally dressed paralegals with lipstick just a few shades too brightly red. It was a perfectly dull place full of perfectly dull people doing the kinds of things that would never appear in a prime-time legal drama, or even a law-firm sitcom.

We zig-zagged past some bland grey cubicles and filing cabinets, and then the receptionist opened a conference room door for me, and I walked in, and –

Clonk. Scrrraape.

That was the sound of my jaw hitting the floor and dragging along as my legs kept moving me forward into the room.

Two people sat at the conference table, which had room for maybe six. At the far end of the table, a balding middle-aged guy in a bowtie straightened and re-straightened a stack of papers in front of him, obviously the lawyer. But I barely saw him because in a seat much closer to me sat ...

Okay, so every guy has a dream-girl, right? Well, I hope it doesn't say too much about me that my dream-girl has always been kind of boringly stereotypical: blond-haired, blue-eyed, long-legged, scarlet-lipped, and blessed with copious breasts and dark, fluttery eyelashes.

This girl's looks picked that dream-girl up, slapped her a couple of times, and threw her out a window.

For starters, a dream-girl can't look right at you, shoot you through with a realization that you've just seen a shade of blue you didn't even realize existed, like a sky made of sapphire, but alive and focused and sweeping over you, measuring you up. And no matter how good a daydreamer you are, a dream-girl's smile is always going to be big and beaming, made of one part happiness and one part sexiness mixed together and leaving nothing to guess about. But the woman looking at me now had a lush-lipped, barely curved hint of a smile, faint and a bit wry, subtle, secretive, maybe not even a smile at all but just the way her head was tilted and the way the light hit those red, red, red lips. Glossy red. A red that begged for her tongue to peek out just enough to wet them, though it didn't.

"Mister Donovan," said the receptionist, "this is Nick Chalmers."

"Oh good!" said the bow-tied lawyer, looking up from his papers. Something relieved in the man's voice made me pretty sure he'd been awkwardly arranging and rearranging those documents for several minutes in a deliberate attempt to avoid staring across the table at ...

Now, dream-girl breasts can get pretty good. I've got a lot of practice at imagining them, and it's one of the areas I like to concentrate on when I'm thinking about a dream-girl. But I'd never gotten my brain to kick out an image like this. Inside her skin-tight white micro-dress – the kind with those little sleeves that barely peek out over the shoulders – she had two perfectly formed, swelling, curving, pert, perky, proud, please-let-me-put-my-hands-on-those breasts. They filled out the silky alabaster fabric of her dress just shy of bursting, and cozied together within its low, low neckline to all but suck the eyes from my head with a fertile valley of cleavage like I'd never seen before.

The lawyer was saying something, I couldn't really hear what, and then I realized I wasn't hearing him, and I blinked and tore my eyes from that incredible bosom to find her looking dryly at me with one fine blonde eyebrow very slightly raised.

"I'm sorry," I said, blinking some more and pretty sure my face had just turned as red as her lipstick. I looked over at the lawyer, desperate not to see what kind of scathing look she was about to give me for staring at her tits. Mister Donovan's lawyerly face held a surprisingly sympathetic expression. I repeated myself because nothing else came to my brain, "I'm sorry, what?"

Donovan's mouth opened, but the woman stood from her chair and offered me a graceful, long-fingered hand with perfectly trimmed nails the same color as her lips.

"Lindsey Moss," she said. The blue of her eyes held me until I realized her face had taken on an amused look, and I took a half-step forward and shook her hand. She had a firm, quick handshake – but then her fingers lingered as she released, drawing briefly along my palms and my own fingers before breaking contact.

I felt myself sweating.

"Nick Chalmers," I said, straightening the collar of my polo shirt with one hand.

Lindsey glanced toward the doorway, where the receptionist still stood. "Yes, that's what she said."

It took a profound act of will not to look at her breasts again while her gaze turned away. I managed it by swiveling to face the lawyer, then walking over to shake his hand.

"Yes, Martin Donovan," he said with a weak smile. "Now if we'll all sit down, I believe we can get through this relatively quickly and painlessly. That will be all for now, Mrs. Anders."

The receptionist nodded and left, closing the door behind her, and for the first time, Lindsey's incredible poise faltered, just for a moment, as she straightened in her chair and looked from the shut door to me to the balding Martin Donovan.

"This is it?" she asked. "What about the rest of the family? It's just me and this guy?"

Donovan cleared his throat as if to gain time, then uncomfortably nodded me toward a chair, since I still hadn't sat down. I took one closer to his end of the table than Lindsey's, not wanting to look like I was invading her space and also because I could then pay attention to Donovan without her in my field of view where I might embarrass myself staring again. It did surprise me that we were the only two heirs, since Mrs. Pinobscott had talked endlessly about her various family members whenever I went over to clean the catbox for her or run Mister Whiskerdoodle to the vet. And she hadn't ever mentioned a 'Lindsey.'

"Well," he said, "as it happens, my client specifically requested two separate readings, one for the majority of her family and friends, and the other for Mr. Chalmers and you, ah ... Miss Moss."

Lindsey snorted and rolled her eyes. "The black sheep reading, huh? You my aunt's sugar boy, Nick?"

"What? No!" It came out a bit of a squawk, but I couldn't help it. From the pictures around Mrs. P's house, she'd actually been pretty hot up into her sixties. But she was eighty-five when I met her and almost ninety when she died.

Lindsey laughed, making it clear she'd been joking. Because it was such a low, sexy laugh, sultry and golden like her hair, the sound made my throat dry in a way that kept me from feeling insulted.

"What's the story, then, Mr. Donovan?" she asked, looking back at the attorney.

Shuffling through his papers, he found two manila envelopes, checked their labels, and passed one to each of us. "By the terms of the will, I am instructed to give each of you these personal letters written by Mrs. Pinobscott. After you read them, I'm to reveal what disposition of property you're each to receive."

I noticed Lindsey seemed a little hesitant to take hers, and that she opened it more slowly than I did mine. But I was curious what Mrs. Pinobscott would want to say to me, so for a few moments, I quit paying attention to my fellow heir and focused on my own letter. It said:

Dear Nick, my favorite and sweetest neighbor. I hope you don't mind wrinkly old Mrs. Pinobscott putting her nose in your personal business, but you know I have always been so confused that a nice young man like yourself should stay single. And not even have a girlfriend since that Carmella left! So I have decided to play matchmaker for you.

What the fuck!

I'm pretty sure my eyes went as big as Lindsey's tits when I read that. They definitely shot up from the paper toHoly shit, Mrs. P couldn't possibly ...

No, the idea was ridiculous. Mrs. Pinobscott's vision was always bad, but not bad enough to think a merely kinda good-looking guy like me would have a chance with a raging-inferno-hot goddess like her niece.I mean, just look at her! And then look at me!Hair color: mud. Eye color: mud. Hair texture: unmanageable, nothing to do but keep it short. Okay shoulders, totally average height. Supposedly, I have a good smile. A little too much forehead – not enough to make me look like Edgar Allen Poe or Frankenstein's monster, but put it together with my no-recent-time-in-the-sun skin, and I came out pretty geeky. And in contrast, this woman came out –

That's when I realized Lindsey had the fingers of one hand up over her mouth and was staring at her letter with a swell of tears in her eyes. I quickly looked away and felt like crap. Mrs. P was dead. Yeah, I'd liked her and she could be funny and I was sad about it, but I'd been expecting her to kick off anytime for the last three out of the four years I'd known her. And Mister Whiskerdoodle was kind of a pain in the ass to help take care of – I hate catboxes. And the old lady almost always wanted to talk about twenty minutes longer than my capacity for neighborhood gossip.

So I wasn't really broken up about her being dead. Instead, here I was in the same room with a woman who'd lost somebody she obviously really loved, and instead of being respectful, my head had decided to run away into stupid daydreams of Mrs. P trying to set me up with a smoking blond sexpot ten thousand percent out of my league.

Just read your letter, dipshit.

But when I did, my eyes widened back up again ... because I was right.

I really can't tell you all that much about Lindsey, we haven't been close for many years. But of all my nephews and nieces, when they were children, Lindsey had the best heart. Headstrong, yes, and one of those people who march to their own drummer. In fact, after college – oh gosh, listen to me, I'm going to go on so long I'll die before I even finish this letter. Anyway. The family hasn't been as good to Lindsey as we should have been, me included. So I want to do something for her and I want to do something for you and maybe it will turn out just perfect the way none of my plans ever do!

You'll understand when Mr. Donovan reads the section of my will that's for you two. It's no guarantee, but I think it will give you a chance at showing her what a nice young man you are, and even though she certainly doesn't look it, I think you'll find that there's a very nice, shy person inside of her too. But for heaven's sake, don't let on to her that I've told you all this! If there's one thing Lindsey has always hated, it's people trying to make her be something according to their own ideas. Just act like as far as you know, the whole inheritance thing is a crazy old lady's demented whim!

Thank you, Nick, for spending so much time with me when you probably had all kinds of better things to do. I'm sure you thought you were just being charitable, and I know I talked your ear off way too often. But you really made a difference for me these last few years. You're a good person.

Now it was my turn to get teary-eyed and sniffly. I blinked a lot and focused on fitting my letter back into its oversized envelope. By the time I got that done and closed the brad on the envelope's flap, though, I'd glanced up at Lindsey a couple of times, and my amazement had crept back in.

Damn, Mrs. P, what in the world do you think you have up your sleeve?

Lindsey was doing that thing women do sometimes when they're about to cry and don't want to, where they look at the ceiling and open their mouths like they're yawning or something and blink really fast and rub at one cheek right by the eye with one thumb. She pulled it off pretty well. I didn't see any actual tears get all the way out onto her cheeks. Also, it was hot as fuck. When she finished, she glanced at me like she was annoyed I'd been looking, so I turned away in a hurry.

At the end of the table, Mr. Donovan appeared ready to do business, holding a couple of papers in front of him between both hands. Seeing us both looking his way, he adjusted his glasses and turned his eyes down to the legal documents.

"I hope the letters were satisfactory," he said, "because the pertinent section of the will is quite brief. It reads as follows. 'Pertaining to the cat, Mister Whiskerdoodle, possession and ownership shall fall to Nicholas Scott Chalmers.'"

Great. No surprise there. Is Lindsey for some reason desperately attached to Mister Whiskerdoodle and now she's supposed to ask me for visitation rights?

"'Pertaining to the property at 17299 Widdershins Court, the accumulated equity shall be divided equally between inheritors Nicholas Scott Chalmers and Lindsey Wyndham Moss. Should the inheritors so choose, Donovan, Donovan, and Furnier, P.L.L.C., shall upon notice immediately execute the sale and disposition of the property and remit to each inheritor one half of all proceeds, net any mortgage balance remaining unsatisfied. Alternatively, from the deceased's previously declared allocation of cash assets for charitable donation, a trust fund for remodeling expenses may be established in the amount of twenty thousand dollars, to be managed by Donovan, Donovan, and Furnier, P.L.L.C., at the equal direction of both inheritors, and full control of the property shall transfer equally to the inheritors upon exhaustion of the fund."

Oh. Sothat'sbetter.I just about halfway thought I understood what all the legalese meant, but I knew it sounded like an improvement over just walking out with an old, puke-prone cat. Luckily, my fellow "inheritor" jumped in right away to clear things up.

"So she's giving us her run-down pit of a house," Lindsey said, "and we can cut and run for whatever equity she's got in it, or we can fix the place up and she'll give us twenty grand to do it."

Donovan nodded, set those papers down, and shuffled in his stack for some others. "That's exactly right. Now, presuming you'll want to be informed in your opinion, here are the current statements of account on the mortgage lien against the home and the latest property valuation from the county tax assessor."

He slid a set of copies over in front of each of us. I tried to puzzle through mine to find the right numbers and figure out exactly what kind of money I was looking at, but once again, Lindsey was way quicker with the statements and the math than I was.

"Whee. If we can get what the county says it's worth, minus the amount she still owes, I make it out to be about ten grand each."

Damn, Lindsey's obviously doing pretty well for herself if ten grand is only worth a 'whee' from her.As I watched her, she leaned back in her chair, hands behind her head, looking up at the ceiling, her gorgeous face wavering between annoyance and distaste. The position showed off the smooth ivory hollows of her armpits fantastically, and lifted and accentuated her boobs even more than the dress already did.Fuck, dude, ofcourseshe's doing well for herself.Lookat her – the hairdo, the dress, those boots, the little designer handbag. And she's obviously smart as hell. Is there some reason you'd expect her to be just scraping by the way you are?

Her blue eyes came back down from the ceiling to land on me like a load of bricks intended for a mural of the entire ocean.

"Okay, sugar-boy Nick," she said, "you ever do any remodeling?"

"Uh ..." Did I want to tell her about replacing my own toilet when the bowl cracked and I couldn't afford a plumber? I decided to be vague. "A little, sure."

Her mouth twisted to one side, and I could almost see her make the decision to take me at my word instead of laying into me with a sarcastic question about what exactly "a little" meant. The mind behind those sharp blue eyes was moving fast now and apparently didn't want to get slowed down.

"Because if we have contractors do everything," she went on, "twenty grand won't get us shit. But I do interior design, and I know where to get the materials, and if you can put in your share of the labor, I think we can get twice as much out of the sale as throwing it straight on the market would do."

"You mean, twice the ten grand you said we'd split?"

Her eyes rolled. Gorgeously. "No. Twice what the county has it appraised at."

"Holy shit," I said. "That would be ..."

"Yeah, a lot. Don't get your hopes up too high, but we might be looking at forty or fifty each, net."

At the end of the table, Donovan tapped his stack of papers against the surface to square them.

"I take it you'll be wanting us to set the trust up, then?"

Lindsey gave me a look that said if I wanted to chicken out, I'd better do it right that very second.

Ten grand, guaranteed, and I look like a putz to the most beautiful woman I've ever had a conversation with, and totally bomb out on any chance with her. Or a couple months of hard work and getting to see her and talk with her about it all the time, and then I totally bomb out with her.

It wasn't a very hard choice. "Sure."

She nodded at me and looked Donovan's way as she folded up her letter and put it in her handbag.

"I think it's what my aunt would have wanted," she told the lawyer, although not with tremendous enthusiasm. "Let's do it."

* * *

Lindsey and I walked out of the office together into the hot Dallas sun of late summer. I didn't try to make it happen that way; it just did. The trip down in the elevator was silent and uncomfortable. Lindsey was tall, probably almost my height even bare-footed. The walk across the lobby filled my ears with the click of her boot-heels, taunting me with the desire to glance down at the sleek black leather of those boots and the soft smooth pale calf-to-thigh stretch of legs that ran from the boots to her skirt hem. But I managed to keep my eyes to myself, even when I stepped ahead and held the door for her. She went through to the parking lot unselfconsciously, fishing for her keys in the handbag as if daring me to look at her perfect ass. Just before I broke down, she found them and turned.

"You're her neighbor, right?" she asked, pulling out a pair of sunglasses too and slipping them on over those fantastic blue eyes. "I haven't seen the place in a couple years. How about I meet you there and we give it a walk-through."