Shemale Intern

"What the fuck?" Rob jump to his feet and rounded his desk before the other man could turn and open the door. He was a good deal taller than the other lawyer, and he loomed over him.

"Jesus, I was just teasing you! I know you're not gay or into freaks like her or anything! Fuck!" the dark man yelped. His eyes widened with fear.

"Don't call her that," Rob whispered. "She's a woman. And a person. A better person than some," Rob sneered at the little man, who cringed.

"Right, shit!"

"Get the fuck out of here," Rob growled. He watched his colleauge turn tail and stared into the office with his arms over his chest. Who was right? Was Maddy a freak or a woman who deserved respect? He knew the answer.

"Rob, you dumb son of a bitch!" he cursed himself as he ran out onto the main work floor. Lawyers and office folk alike called to him as he ran past, but he wasn't interested. He found her in the hall to the elevator, just in time.

"Maddy!" he called.

"Yes, Mister Crane?" she asked coolly. She paused on the threshold of the elevator. The day was warm and sunny, and she wore a cute little green and white dress. Her hair flowed over her shoulders in glossy brown waves. Her slender legs were perched atop strappy brown heels. Her eyes blazed as she faced him. She was furious.

"I'm sorry," he said as he stepped up to her. She waited, and the elevator door closed.

"For what, Mister Crane?"

"Maddy," he groaned. "I freaked, okay?"

"Whatever do you mean?" she crossed her arms over her chest. It pushed up her cleavage, the tan curves reminding him just how much a woman she truly was.

"I mean that I like you, Madison Forsythe. You're an amazing woman, but fool that I am, I got scared when we got too close," he admitted.

"Is that all?" she tapped her foot.

"No," he shook his head. "There's some bullshit homophobia too. I can't deny it."

"But you weren't like that before, what changed?" she wondered. Her eyes were starting to water, and her bottom lip trembled.

"Last week, at your apartment..." he blushed.

"What, we didn't do anything, did we?" her eyes widened.

"No, no. You fell asleep on the couch. You said my name, and well," he cough nervously. "Well, I guess certain parts of you, uh, came out to play?"

"Oh God!" she gasped and clapped her hand over her mouth. "I got a boner, didn't I?'

"Yeah, kinda," he chuckled. "I, well, it scared me a little. I'm not used to that kind of thing."

"Well, thank you for telling me, Rob," she said at last. "I know you're straight and its a lot for a guy like you to get used to. I understand." Her voice was soft, and terribly, terribly sad. "Maybe one day, I'll get tired of it and well, go all the way. But I'm not ready to go that far just yet. I get it if you're not ready for me before then."

"What are you talking about?" he took her arms in his hands and peered into her eyes. She looked so vulnerable. He'd hurt her feelings, and he could feel his heart breaking for her.

"You know, having the operation. So I would be all woman for you," she whispered.

"Is that what you want?" he asked softly.

"If it means I can be a real woman and have a guy like you..." she trailed off and looked away as a tear rolled down her cheek.

"You ARE a real woman, Madison," he said firmly.

"But you said-" she choked up, and he pulled her into a tight hug.

"I said I wasn't used to it. But that's my problem, not yours. Don't change yourself for my sake. Or anyone's sake but your own!" he said fiercely. It suddenly seemed so monstrous to him. That he might demand she lop off a part of her body before he accepted her for what she already knew herself to be.

"Do you really mean that?" she asked.

"Come with me," he took her hand. He didn't give her a chance to object as he pulled her back down the hall to main office. Heads turned as all eyes focused on them.

"Uh, what are we doing?" Madison whispered to him. She was blushing, and her graceful body trembled.

"Maddy?" he faced her, looking into her soft brown eyes. He didn't raise his voice much, but the office grew quiet. He could almost hear everyone straining to listen in.

"Yes, Rob?" she gulped.

"Now that you're no longer working here, what do you say you and I go on a proper date? We'll catch a movie, get a drink, who knows?" he grinned. Somewhere behind him, Antonio snorted in derision. Fuck him.

"Okay, that sounds nice," Madison bit her lip.

"You've got all your things?" he asked.

"Yes, I was about to leave, remember?" she brightened a little.

"Good. Are you free say, right now?" he smiled.

"You don't much waste time, do you Mister Crane?" she giggled.

"Not when I've made up my mind. Let's get out of here!" he took her arm. To Hell with the idiots at the office, especially Antonio. Madison was a beautiful young woman, and he was smitten. Sure, her erection had scared the piss out of him, but he'd learn to adapt. It was worth the effort.

***

The moment of truth had arrived. Rob had taken his time with Maddy. They'd dated, they'd hung out. They'd spent hours and hours just talking. They'd even had more than one steamy session making out on his couch after their dates. He'd been seeing her for three weeks, though, and the time had come.

"Maddy," he said softly as he pulled away from a particularly passionate kiss. She was a fantastic kisser, playfull, energetic, always surprising. They'd come back from a casual Saturday in Central Park and had gone straight to his couch.

"Yes, Rob?" she batted her long, dark eyelashes at him. Her hair was back in a girlish ponytail, and her lanky body sheathed in a bright floral print sundress. She was gorgeous. He could feel the bulge growing in his jeans. He glanced down, and sure enough, a little tent was starting to form in her skirts.

"Let's take this to the bedroom," he suggested.

"Are you sure you're ready for this?" she asked. She lay a hand on his and looked into his eyes. She wanted to make sure.

"I think so," he stood and pulled her up. Without a word they stepped into his bedroom. They faced each other.

"Maybe you should undress first?" she offered. He could tell she was a bit nervous. No doubt some guys reacted badly when she took off her clothes. The bastards.

"Would that make you more comfortable?" he pulled off his tee shirt. While he didn't have a whole lot of time for the gym, he was lean and fit, with just a touch of hair on his toned chest. She simply nodded and watched him. Her eyes seemed to be drinking in his body. Few women had ever looked at him with such longing.

His pants and shorts came next, and he blushed a little as he exposed his stiff, bobbing erection. As a youth he'd been obsessed with worry about the size of his manhood. He knew perfectly well that his six inches average, or perhaps a hair more than average. Women had never had cause to complain, and he'd lost his youthful self-consciousness about it. What if she was bigger?

"Very nice," was all she said, with a faint little smile on her lips. She reached out and wrapped her long, slender fingers around his cock. He'd never felt so hard in his life. His pulse pounded under the steely flesh.

"Your turn," he said. Maddy nodded again and stepped back. She kicked off her flat sandals and pulled her dress over her head. Her long brown hair fell in a tangle over her face as she stood looking down at her feet. As slender and boyish as she was, her breasts were high and incredibly firm. She had long pink-brown nipples that just begged to be sucked. Her belly was flat, smooth, and lightly tanned. Her white panties were shear satin. The fabric stretched tight around an enormous bulge protruding between her slim thighs.

"Wow," was all he could manage. His voice sounded hoarse to his own ears. They looked up at the same time. Her eyes darted back and forth wildly.

"You're not freaking out are you?" she asked.

"Oh Maddy," he brushed her hair from her face and cupped her cheeks in his hands. "Why would I freak out? You're very beautiful."

"A lot of guys do," she said softly, but seemed to relax.

"Maybe they're just intimidated?" he chuckled.

"Yeah," she forced a laugh. "I'm sorry about that. I can't help it."

"I can take it. Go ahead. Take your panties off," he urged.

"Okay, you asked for it," she said in a soft, gentle warning. Her thumbs hooked into the waistband and she pulled them down ever so slowly. The silky fabric stretched over that massive lump. He kept waiting to see a her pubic hair, but when the root of her veiny shaft appeared he realized she kept herself smoothly shaved. She gave a sharp little tug and her fat, semi-hard shaft sprang up from her panties. Her cock was pale and smooth, with a fat blue vein running down the top and a bright pink head just a hair wider than her heavy shaft. She kicked her legs and her panties dropped to the floor. Her cock wobbled as she stepped out of them, swinging before a huge, low-hanging set of hairless pink balls. He stared at her for a long moment as she shifted her feet nervously.

"You mean you actually thought about getting rid of that?" he wondered.

"What do you mean?" she gulped.

"If I had a set like that, I'd never get rid of it!" he laughed and shook his head. "You must be very proud!"

"I am, kinda," she gigged. "Sometimes it's more trouble than its worth. And I can't help but think I'd be more of a woman without it."

"No way, Madison Forsythe. You're very much a woman." He kissed her, good and hard. She moaned into his mouth as she pressed her lithe body into his. Her nipples teased his chest as her soft orbs flattened against him. His cock poked her belly, but he could feel her starting to rise.

"Even with this?" she asked shyly as she pulled away. Her cock had grown during their kiss. It thrust out from her body, pointing ever so slightly downward as it was pulled by its own weight. He wouldn't have been surprised to learn that she was twice his size, in length and girth.

"Especially. It makes the rest of you even more womanly," he said. The contrast was stunning. A supermodel with a porn star's dick. He'd never been attracted to men, or even thought about any penis beside his own. It was different with her. She was a woman, and her cock, despite it's more-than-manly size, was a woman's cock.

"Well," she grinned. "How about you show me how womanly you think I am?" she again took his cock in her hands.

"How would I do that?" he smiled.

"By fucking the hell out of me!"

"Oh I will. On the bed!" he said as he guided her back. He practically jumped on top of her, kissing her again while his hands roamed her body. Her breasts were super firm. Probably implants, though she hadn't gone overboard with the silicone, if so. They felt just like a pair of tight twenty-year-old tits in his hands. He kissed the hollow of her neck as he groped her breasts, but could only hold out so long before he sidled down the bed. He could feel her huge erection poking his abdomen as he sucked her long, pink nipples.

"Oh, that's so nice," she whimpered as he moved further down. Her belly fluttered as he kissed it and dug an eager tongue into her belly button. Her cock bumped his chin, and he moved to the side to kiss and caress his way down her legs. She was so tall, her legs were amazing. There didn't seem to be an end to the perfectly formed limbs. At last he lifted her foot and lovingly sucked each of her long, slender toes.

"Oh God, enough foreplay, you're driving me crazy!" she whined.

"That was the plan," he winked as he looked up at her. Her cock arched through the air, the tip resting against her body well above the belly button. Her big pink balls hung low between her widely spread legs.

"Fuck me, Rob!" she pleaded. He didn't have the first clue about anal sex. He'd never tried it. The young transsexual whined and reached for her purse. She tossed him a little bottle of water-based lube. "Use lots of this!"

"Right," Rob blushed as he squirted a huge glob of the clear goo onto himself. It was cold, but heated up quickly as he stroked his manhood. Maddy lay back, spreading her long legs wide and arching her back. She reached down and cupped her huge balls, exposing her tight pink hole. She teased herself with a fingertip.

With his target in sight, the young man scooted forward eagerly. They sighed together as her tight ass opened up for him and accepted his hard, wet cock inside. Rob smiled down at her. Never had he felt anything as hot and tight as Maddy's sweet little ass!

"Yes, more, give me more!" she moaned. She held his neck, watching his face as he pushed more of himself inside her. He sank to his balls in a smooth, even stroke. The tube of her rectum seemed to milk his cock, and he started to pound.

"You're so fucking hot, Maddy!" he grunted as he hunched into her like a mad man. Her big tits jiggled as he fucked her, and her grip grew tighter around his neck and shoulders with each powerful stroke. He'd lusted for her for so long, he couldn't hold back. He grit his teeth, panting as he tried to hang on for each passing minute.

"Cum in me, Rob! Make me your girl!" she pleaded. She looked so lost, so desperate for it, he couldn't hold back another instant!

"Fuck!" he barked as he crammed his cock into her as deep as he could. She smiled as he cock shot his thick, hot load into her guts one blast at a time. He smiled back at her as he rotated his hips against her. He'd only lasted a few minutes, but those minutes had felt so damn good.

"Thank you Rob," she said as she loosed her grip on him and stroked his face lovingly. "You made me feel very special."

"Made?" He cocked his head and pulled from her. Her tight ass clamped shut as he withdrew, squeezing the tip of his cock hard enough to make him shudder. Her own cock was still hard as steel, and leaking precum all over her big, round tits.

"Oh, are you up for another round already?" she asked gleefully.

"Not yet, but I think you could use some attention," he glanced down at her sex.

"I really could," she admitted. "But not every guy likes, to well, do things with me down there."

"That sounds selfish of them," he noted. He took her in his hands, surprised at how natural it felt. It didn't seem weird or gay at all. In fact, her huge girly cock felt pretty amazing in his hands. It was impossible not to compare how huge and hard she was to his own cock. She made him seem tiny. He should have been jealous, instead, it turned him on. He began to stroke her slowly up and down, holding her cock straight up.

"As long as they fuck me nice and hard," she shrugged, but there was a shy, hopeful look in her eyes.

"Have you ever fucked them back?" he wondered as he rubbed his thumbs against the underside of her cock. Her silky skin was slick with precum. She shook her head. "Do they suck you off?"

"Not often," she admitted.

"Do you like it?" he wondered. He was leaning forward.

"I won't lie. I do. But if a man doesn't want to do it, it kind of makes me feel like a real woman I mean... Oh God!" she squealed as he cut her off. He opened his mouth wide and engulfed her cockhead. He watched her pretty face as she twisted and groaned. Her cockhead filled his mouth completely, but he sucked gently at it. The flesh was so smooth and soft, but there was such hardness beneath. He could smell her musky scent, taste her salty precum. He sucked harder, and pushed himself down until the tip of her shaft pushed against the back of his throat.

"You don't have to do this," she whispered as she ran her fingertips through his short, thick hair.

"I always like to spoil my women. Treat them like princesses," he explained as he pulled her cock from his lips. He licked her shaft slowly, lazily.

"I want to be your princess," she said softly.

"Good," he said, and opened wide again. She seemed to be fighting herself as he sucked and licked at her huge cock. He'd never done it before, but he knew what he liked, and tried his best to give her just that. From her little jerks and whimpers of pleasure, he was doing something right. But her brow furrowed, as if in worry.

"You really like sucking cock," she observed.

"No," he said as he rubbed her big tool against his lips. "I like making you feel good, Maddy."

"Yeah?" she watched him carefully, a little smile starting to grow on your lips. "You seem to really love my cock, though," she giggled.

"I do! If you had a pussy, I'd love that too. But you're perfect just the way you are," he said.

"I believe you," she whispered. Her fingers ran through his hair again, and to his surprise, she guided his head right down over her massive prick. He nearly came when she pushed into his gurgling throat. He gagged around her, his throat constricting painfully, but he sucked as hard as he could, licking furiously. He pushed her hands away, and with tears streaking down his cheeks, impaled himself on her cock again and again.

"This feels so good!" she cooed. Rob was a patient man. He truly loved settling between a woman's legs and making her scream his name just from his hot little tongue. It was different with Maddy, of course. Her huge cock hurt going down, stretching his throat, but that only made it better. He closed his eyes as he bobbed, losing himself in the joy of pleasing his gorgeous girlfriend.

"Gonna cum!" she squealed after quite some time. Her slim hips jerked on the bed, making the mattress bounce. Rob sucked harder even as he pulled back. His tongue flicked at the very tip of her cock as she began to spew her load.

"Oh ROB!" she screamed. The first blast coated the inside of his mouth with her salty tang, and he swallowed it down, only to have his mouth fill again and again. He couldn't swallow fast enough, and it drizzled over his lips and ran down her shaft in a thick stream. When she finally stopped spurting he pulled back and lapped up the juices coating her heavy shaft.

"Did I make my little princess feel good?" he asked with a smirk. He knew the answer, but he liked hearing it all the same.

"That was amazing!" she nodded vigorously as she panted. Her cock throbbed in his hands, and he kept working his tongue, keeping her hard.

"I'm glad you liked it, I didn't really know what I was doing," he admitted with a shrug.

"You could have fooled me! God I need to get fucked again already!" the young transsexual laughed as she sat up on the bed.

"Sucking cock was a first for me," Rob said as he, too, sat up. His cock stuck up straight from his body, wet with sticky lube and his own cum. "Why don't we do something neither of us has ever done before?"

"What?" her eyes went wide and her cock jerked, snapping up against her flat belly.

"You said you'd never fucked before. I've never been fucked before," he blushed at the suggestion, but it just seemed such a shame that her magnificent cock had never truly been put to use. She was terrifyingly big, but with his heart thudding in his chest, he knew he wanted to give her everything.

"Don't tease me, Rob," she said. "It might not be a good idea."

"Why not?"

"First of all, I might be too big. I know it looks sexy, but my size might make it too painful," she explained.

"So we'll take it slow," he gulped.

"Second of all, well," she looked down at the rumbled bedspread between them. "Will you still think of me as a woman? Will I think of myself as a woman?"

"Hey, you are a woman. What's a dick got to do with it?"

"Oh," she looked at him shyly. "Thank you, Rob."

"Any time, Maddy," he pulled her into his lap, and she wrapped her legs around his back and ground her little ass against his throbbing hard on. Her own dick pressed against his tight abs, the whole length of her shaft flat against his body. He kissed her tenderly and brushed her long hair from her pretty face.