Shemale Intern

byLara_Longstaff©

The first time Rob Crane saw her, she took his breath away, literally. Madison Forsythe was her name, a bright bubbly intern at his law office. She was tall, eye to eye with Rob himself when she wore heels. She had long brown hair she kept loose about her shoulders and a face like a kitten. Her willowy body would have been the envy even of runway models. Naturally all the men at the firm adored her as much as the women despised her.

The senior partners of the firm of Johnson, Schwanz, and Steele took turns hosting parties whenever they won big cases. It was Allison Steele's turn, and the cold, imperious woman invited all the lawyers, paralegals, secretaries, and interns onto her one hundred twenty foot yacht to celebrate. It was there that Rob, back in town from litigating a case on the East Coast, ran into the new intern for the first time. Or rather, she ran into him.

"Oh so sorry!" the intern said as she spun. Her elbow caught Rob right in the pit of his stomach, making him gasp. He wheezed for breath and leaned back against the ship's rail. Luckily, the huge boat was safely moored on the pier, or else Rob feared he'd have lost his lunch right there all over the deck.

"No worries," he managed to whisper. She'd jabbed him right in the diaphragm, and his chest ached as the muscle spasmed. He was a tall, lean fellow, just thirty, with unruly, sandy hair, and a perpetual look of a troublemaker on his face. He kept fit, of course, and recovered his breath quickly enough. He shook his head and his vision focused on a pair of long, slender bare feet on the yacht's deck.

"Pink toenails," he said softly, making his accidental attacker giggle.

"I'm so clumsy sometimes!" the girl rested a hand on his shoulder. He lifted his eyes, slowly of course. He'd never seen a pair of legs so long, and her tiny blue shorts left a lot of limb exposed. The rest of her was just as nice too. Slim hips, tiny waist, a full bosom filling out her blouse. Her face was pinched and her soft brown eyes narrowed in concern.

"I'm all right," Rob forced his stubborn lungs to pull in several long deep breaths. The girl looked about twenty. One of the senior partner's little girlfriends, he thought.

"Well, let me get you a drink, at least!" she grinned. "I spilled mine when I bumped you!" Her voice was fairly deep for a woman, but smooth and velvety. She winked before bouncing off into the yacht's cabin without giving him a chance to respond. Rob's eyes followed those perfect legs and her little tight ass as she swished into the ship's interior.

"She got you good there, my friend," Antonio laughed as he sat beside him. The short, swarthy man was another junior litigator. Like Rob he wore a casual suit, but no tie. It seemed a natural look for the handsome Italian.

"Yeah, no kidding," Rob chuckled. "Who is she anyway? Another one of old man Johnson's little playthings?"

"Nope, she's a new intern. I use that word loosely, by the way," Antonio slapped him on the back hard enough to make Rob wince.

"Hired for her looks then?" Rob rolled his eyes. Wouldn't be the first time.

"No, she's a good intern. Twenty-three, law student. Smart as hell. The word I was using loosely was she," Antonio leaned in to whisper the last.

"She? What do you mean?"

"That rumor is, she's not really a woman. Madison used to be a dude," Antonio made a disgusted sound in the back of his throat and shook his head.

"Oh come on, she's gorgeous!" Rob didn't believe a word of it. Antonio was probably trying to throw him off his game. Both men were single, and when a pretty single woman came into their lives, things could get competitive. Rob supposed it was natural. Good lawyers liked to win. At everything.

"What you don't think trannies can be convincing?" Antonio laughed. "Hey, if that's your thing, don't let me stop you!"

"Oh get out of here!" Rob laughed as he pushed his colleauge aside. The girl, Madison he'd called her, was coming back. She had a tall flute of champagne in each hand and a twinkle in her eyes.

"I'll leave you to it, buddy," Antonio laughed and rejoined the laughing group clustered at the bow of the big ship. The party was just getting started, but with the booze flowing freely, people were already starting to get pretty lively.

"Oh, you're looking better! For a second there you looked like one of the lobsters from the buffet table," she handed him a glass, and her long fingers brushed over his for an instant.

"What do you mean? Crabby?" he took a sip. Bollinger. Always the best at one of Steele's parties. He wished he could bring himself to like it. He preferred a good cold Budweiser. Not that he'd tell any of his colleagues that.

"Kinda," she smile up at him. "But mainly just red."

"You got me right in the sweet spot," he acknowledged.

"I've always been good at finding that," she said before sipping her own drink and looking out across the harbor.

"Have you now?" he chuckled. "I'm Robert Crane. I'd have met you already, but I'm just back in town from LA," he explained.

"Welcome back, Rob. I can call you Rob, right?" she asked, though from the tone of her sultry voice, she already knew the answer.

"Ohfcourse, everybody does."

"That's what I thought," she nodded up at him.

"How's that?"

"All the other women at the firm told me that Rob was the best looking guy at the office. Rob is the nice one, they said. And a lot less greasy than Antonio." She looked at him sideways, a little mysterious smile on her wide pink lips.

"I'm only a little bit greasy," he admitted. "Truth is, I'm a terrible lawyer and I work as a fry cook on the evenings to help pay the bills. Some of the grease sinks in, you know?"

"Do you get to wear one of those cute little white aprons?" she wondered.

"It's black actually. Matches the hairnet."

"You must look very handsome in all that," she giggled.

"You think? Is that why all the ladies chase me when I'm leaving for work?"

"I believe they do chase you," she said thoughtfully. "I'm Madison, by the way. My friends call me Maddy. Maybe one day I'll let you call me Maddy too. But you'll have to improve your lawyer skills and quit that night job. I don't want friends who smell like fry grease."

"You've just given me new incentive to succeed, Madison," he laughed.

"I'm glad to inspire you," she finished her champagne and set the empty glass on the rail with a frown.

"Don't like the bubbly?" he asked.

"I'm more of a tequilla gal. Shots. Margaritas. Sunrises," she shrugged.

"I wouldn't mind sharing a sunrise with you," he said. He wasn't normally so bold, especially with women who worked at his company. In fact, as much as he flirted with them, he'd never dated anyone from work. A good way to get yourself or someone else fired. Not only was she pretty, and fun to talk to, the way she turned her nose up at the expensive champagne endeared her to him. She was a regular girl. Or was she? Surely Antonio was full of shit about his assertion.

"Why Mister Crane!" she laughed and leaned into him. "I do believe you're flirting with me! What would Miss Steele say?"

"That I have good taste in women?"

"Oh no. She'd probably fire us both. I think she's got her eyes set on you herself. She just can't wait to get those wicked claws of hers into you!" Madison teased.

"Eww!" Rob laughed. Allison Steele was old enough to be his mother, and already as dried up as an old raisin.

"But seriously, I saw you talking to Antonio. He didn't try to warn you about me?" she asked, seemingly casually. Her shoulders tensed up though, and she braced herself against the ship's rail. She looked ready to run at a moment's notice.

"He may have," Rob shrugged.

"Best to get it all up front," she said, suddenly business-like.

"You told him that to keep him off you, didn't you?" he chuckled.

"No," she shook her head. "Well, okay, partly. I've only been at your firm a week and he's already asked me out ten times. When I told him I was transgendered, it shut him up. But, well, it's also the truth."

"You're not joking are you?" Rob took a step back and squared his shoulders toward her. He looked her over carefully once more. She was tall, sure, close to six feet. Her hands and feet were long, but graceful and delicate, despite their size. She did have a rather deep voice for a woman, as well. And slim, almost boyish hips. Still, even those clues weren't enough. She was just too feminine, yet the serious look in her eye told him otherwise.

"No, Rob. I've been living as a woman for five years, since the day I moved out of my parents' house," she told him. She seemed to relax a bit as they faced each other. A small smile was creeping back onto her face.

"That's really brave of you," he said at last. "I don't think I'd have the guts."

"It's not about guts. It's about not being ashamed," she corrected him. "I like who I am. I'm proud of who I am."

"I can see that," he chuckled. "But sue me, I still think you're brave."

"Give me a couple years. I'll be a lawyer then too," she warned him. "I'll sue the pants right off you!"

"Is that what you'd want? My pants?" he flushed as the words past his lips. She'd told him right out that she was a transsexual and he'd gone on flirting with her.

"Oh I'd sue for the whole package. But your pants are definintely part of the deal. I'll get every last inch of you," she licked her lips.

"And I thought I was a tough lawyer!" he laughed. "You'll do well, I bet. A good lawyer's got to be hard enough to go for the kill without feeling guilty."

"Did you just make a joke about how hard I am?" she frowned and put her hands on her hips, staring him down with those big brown eyes.

"Uh, sorry, totally unintentional," he blushed. Talk about a verbal faux pas. "I didn't mean to, uh, comment on your, uh..."

"Oh, I'm just teasing!" she laughed and leaned in. She rested a hand on his shirt, and his nipple hardened instantly against her palm. It wasn't the only thing growing stiff.

"Thank God," he sighed.

"It takes more than that to get me mad," she chewed her bottom lip and looked down for a moment. She looked back up through her long, black lashes. "Or to get me hard, for that matter."

"Oh," he gulped.

"You should see the look on your face right now!" she cackled gleefully. She pulled away. "I'm not trying to get into your pants, Mister Crane."

"Okay," he sighed in relief. Or was it disappointment?

"You seem like a nice guy. A lot less stuffy or creepy than most people here. Come on," she grabbed his wrist and pulled him along. "Let's see if they have anything to drink back there besides champagne!"

***

The next few weeks were hell on Rob, professionally and emotionally. Cases were piling up, and there didn't seem to be enough hours in the day to take care of them all. He came in at seven every morning and was lucky to get home by ten at night. Just enough time to scarf a sandwich, wash it down with a beer and try to get some sleep before doing it all again the next day.

The workload was so high, the firm assigned him an intern to work with him side by side. He almost objected. He was young and hungry, eager to prove he could do it all on his own. But then the partners had given him Madison, and he found himself agreeing without protest. The day they'd met they'd spent the whole office party drinking and laughing together, hardly paying any attention to the other guests. She had been even more intoxicating than the beer they'd found chilling in the back of the yacht's galley. The feeling only grew more strong as they worked side by side. She was funny, clever, and never missed a chance to tease him.

Everyone at the firm noticed, of course. The women gave him prim little looks. They disapproved. The men were either smug, or outright disgusted. Antonio had even asked him if Rob had gone queer for the pretty intern. He wouldn't turn her away though. She was smarter than any of the paralegals or other interns. Hell, she was smarter than most of the lawyers.

"The Radford file's done," Madison sighed as she plopped the heavy folder on his desk. She collapsed onto the chair across from his cluttered desk, looking miserable. Some interns worked their forty hours a week and left. Not Madison. She'd stayed at his side every minute. With a work ethic like that she'd make one hell of a lawyer when she finished school.

"Thank God," Rob muttered. He rubbed his eyes and leaned back in his chair. His tie felt like a noose, and he pulled it off from his neck. The Radford file was the last of their projects.

"Just in time too," she added. She kicked off her heels and turned to plop her feet onto the chair next to her. She flexed her toes. They weren't pink anymore. She'd repainted them red. Where did she find the time?

"Yeah," Rob picked up the phone. "Hey Marcus, we've got the Radford file ready. Do you mind posting it now? I'd like to get it out before five!" Rob barely waited for the office manager to agree before hanging the phone back up.

"This was the hardest three weeks of my life," Madison said heavily. She turned to face the handsome man. "But I wouldn't change a thing," she grinned.

"Yeah?" he chuckled. She was right, of course. While she was only paid a pittance as an intern, the experience would be invaluable to her.

"Yeah, but I've only got another week before I go back to school full time," she said sadly. "I'm going to miss this place," she said.

"Really?" he chuckled. "You're going to miss eighty hour work weeks?"

"Maybe not that, so much," she admitted.

"Well, I'm not shy about it. I'm going to miss you when you go back to school. You're one in a million, Madison."

"Aww, you're just saying that," she blushed.

"I bet you hear guys tell you that a lot. But you're not just a pretty face. You're going to be one hell of a lawyer," he declared.

"That means a lot coming from you. They said you were their number one hot shot around here, and I can see why," she sat up straight and brushed her hair away from her face.

"Well, it's Friday, and for once, we don't have to come in tomorrow," he said.

"What are you thinking, Rob?" she said as she slipped her slender feet back into her sensible black pumps. She wore a knee-length brown skirt and matching jacket, quite conservative and professional really. Even so, she was sexy as hell. He'd been thinking about her more and more, when he was given a spare moment to do so, anyway. If he were honest, he'd tell her he was thinking about how sexy she was.

"I'm thinking I need some beers and you need some tequila," he said instead. As well as they got on, she was seven years younger, and an intern. And a transsexual. He didn't know much more than that. Had she had reassignment surgery? Was she all woman now? Could he handle it if she hadn't? Could he handle it even if she'd had surgery to become all woman? Just knowing what she once was?

"As long as you're buying!" she laughed.

"That's only fair. Let's get out of here!" he left his tie and suit coat at his desk. His work was done, for now. He needed to relax, and he couldn't think of a more fun person to unwind with right then.

***

"No, really!" Madison slurred as she leaned against Rob's arm. As slender as she was, with her height she was no lightweight, and the tall man struggled to keep the drunk young intern upright. "You're the BEST Rob! I mean it!"

"You've said that like twenty times now," Rob chuckled as he staggered up the stairs to Madison's apartment.

"You don't undrestand!" she said emphatically. "You are the best! Like, gosh, it's unreal. You're so cool and nice to me."

"So you've been saying," he laughed as they reached the landing. "This your apartment?" he nodded at the door.

"Yup," she nodded, her head bobbing. She slouched against the wall and pulled her keys from her little clutch. He dropped them as he tried to snatch them up. He tried five different keys before he finally got the right one. They staggered into her tiny living room before plopping onto her couch.

"Wow, I drank too much," Rob muttered. His head was starting to pound. It felt like tiny grenades were popping off inside his skull every few seconds. He was going to have to sleep all weekend just to feel right again on Monday.

"Yeah, me too," Madison giggled. She sat up straight. Or tried to, she was swaying a little. She finally got her jacket off and she flung it across the room like garbage. Her heels came next and she sprawled with her feet on the coffee table and her long legs spread slightly. She heaved a great sigh and closed her eyes.

"So, you're really going back to school in a week, Madison?" he asked after a moment.

"Maddy," she corrected him absently.

"Oh, I thought that was for your close friends," he smiled and put an arm around her slender shoulders. She cuddled up against him, resting her cheek on his chest.

"You're my friend, Rob. You're the best," she repeated again.

"Not true," he brushed her hair away from her forehead. Her eyelashes fluttered and she wiggled against him, trying to get more comfortable.

"Don't contradict me," she mumbled.

"You're the best, Maddy," he said. His head was spinning, and not just from too many beers. She was so warm against him, so comfortable. He'd had a dozen girlfriends over the years, but never once had felt as close to one as he did to the young transsexual quickly falling asleep in his arms.

"No," she croaked and wrapped an arm around his middle. "You are," she whispered. A moment later, a soft snore escaped her nose.

He was tempted to wake her up and continue their ridiculous argument. He loved talking to her, even when they were both drunk. He sighed and pulled himself out from under her. As gently as he could he tucked a pillow under her head and pulled her feet onto the couch. She needed to sleep it off, and so did he.

"I guess I'll call a cab," he muttered as he pulled his cell phone from his pocket. He stared at her as he made the call. She was so damn beautiful. With the cab on its way, he put his phone away and watched a little longer. If they hadn't both been so drunk. Or if she weren't a...

"Rob," she moaned softly.

"Yes?" he whispered. He eased himself down onto his knees on the carpet. Her pretty face was scrunched and her eyes shut tight. She'd said his name in her sleep. He watched her closely, wondering if she'd say anything else. She stirred, and his dark eyes opened wide. A tent was growing in her skirt, lifting the fabric from her slender body.

"Uh, see you Monday," he gulped, and ran out to the street so fast he nearly tumbled down the stairs.

***

"Aren't you going to go out and wish your little tranny girlfriend goodbye?" Antonio teased as he shut the door behind him. Used car salesmen didn't have smirks as oily.

"What the fuck are talking about?" Rob growled. He tried to focus back on his computer screen. To say things had been awkward around the office had been an understatement. They'd reassigned Madison to the office workers, and she'd spent her nine to five's filing and copying and collating. They'd passed each other in the office several times, and they'd always greeted each other cheerfully, but Rob couldn't bring himself to do more than that. If he stayed too long around the alluring young woman, he didn't know what he'd do. She wasn't a woman, not really. She still had her manly parts, he'd seen evidence of that himself. He was so confused, all he could think to do was to shut himself in his office and try to concentrate on work.

"Madison is leaving in about five minutes," Antonio frowned. "I thought you two were friends. You worked well together."

"Yeah, I work well with a lot of people. Even assholes like you," Rob grunted.

"No need to be an jerk about it," Antonio chuckled. "I mean, you're into trannies. What's the big deal? I just never figured you for a guy, who you know..."

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byLara_Longstaff© 29 comments/ 93386 views/ 240 favorites

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