Becoming Samantha Ch. 01

Sam loved his mother, but his visits home were an exercise in patience. This one, in particular, was a case of bad timing. He'd intended to announce that he'd recently begun hormone replacement therapy; a huge step in transitioning to a woman. The evening news put an end to his plan.

"Fucking faggots," his stepfather, James, growled at the television, during a report about an LGBTQ pride parade.

"Goddamned fairies," his stepbrother, Jimmy, added.

"If you two can't be civil, we'll shut it off," Sam's mother scolded.

"Well, these people are ruining the whole country," his stepfather insisted, pronouncing the word people in a way that revealed he believed members of that community were anything but.

What his mother saw in this bigot Sam couldn't fathom.

"They're being who they are," he said, quietly.

"Bullshit," James objected.

"Bunch of queers," Jimmy chimed in.

"Demanding all kinds of special treatment," James continued.

"They're only asking to be treated equally," Sam pointed out. "Like any other American citizen."

"How can I respect a 'woman' with five o'clock shadow?" Jimmy sneered.

Not out - even to his mother, though she suspected - Sam sighed, and tried to ignore them both for the remainder of dinner. In-between mouthfuls of food, Jimmy made several more comments, as if his feelings on the subject weren't already clear, and Sam silently wondered what would happen if he invited his mother - only his mother - out to dinner next time, rather than come here again.

"Hey, dickhead," Jimmy said, as Sam helped clear the table, "some of the guys are heading over to Double Dee's for a while. Wanna come?"

Though pansexual, Sam had no interest in hanging out at the local strip club with Jimmy.

"No, thanks," he said. "I've got a webpage to get up by morning."

Actually, he had two days to finish that particular project, but didn't reveal this.

"What are you, gay?" Jimmy taunted, punching his shoulder.

The blow knocked loose an idea in Sam's head.

"I think I'll hang on to my singles tonight," he said. "Thanks anyway."

Leaving his mother's house, he drove home, thinking. He had to be very sure about what he was about to do. Was teaching a lesson worth the very real risk of getting his ass kicked? Jimmy wasn't unattractive; he was handsome even, Sam conceded. His 6'2" had a full five inches on Sam. He'd played football in high school, and had managed to maintain most of the athletic frame he'd sported. In contrast, Sam, a member of his university's performing arts department, had a slight build, and soft facial features. No doubt Jimmy was an idiot; but it wouldn't be the first time Sam had fucked someone with an IQ no larger than their shoe size.

Sam decided to take the chance. Arriving at his apartment, he gingerly shaved - everything - then showered. He dressed slowly, watching himself in the full-length mirror, before applying make-up and pulling on a brunette bob-cut wig, completing his transformation into Samantha. Though she didn't need them, Samantha picked up a pair of rectangular-framed glasses. They made her - she thought - look like a naughty librarian. She laughed, then slipped them on.

I'm ready.

She hesitated for a moment, examining her reflection. Twisting slightly to inspect her ass, she could see the faint outline of the thong she wore. Knowing anyone looking close enough would see it too, a smile creased her crimson lips. She blew herself a kiss, spun, and strutted toward the door.

Samantha sauntered into the club. She could almost feel the eyes of half the men there roaming over her body. The black, wet-look, pleather leggings she wore hugged her ass and legs, and reflected the multi-colored spinning lights. A tight, blood red top clung to her, showing the lines of the bra, and the curves of her small, fake breasts. Ankle boots with four-inch heels augmented her height, boosting her to more than six feet. She moved carefully in the dizzying combination of flashes and shadow.

Finding an empty seat, she dropped her clutch - barely large enough for her cell phone, and a few other important items - on the bar, and ordered a drink. Trying not to appear obvious, Samantha took a minute to admire the surgically-enhanced blonde spinning on the pole a dozen feet from her, then let her eyes drift across the faces surrounding her. She spotted Jimmy and his friends - Tony, Rick, and Phil. She knew all of them from the few times her alter ego had hung out with Jimmy, and she chuckled as she watched them toss dollar bills at the dancer swaying in front of them.

Jimmy sucked down his beer, and motioned to the bartender, who promptly delivered another. Samantha waited. She found herself unconsciously bouncing to the music while sipping her drink. As the song ended, she felt a tap on her shoulder. Turning, she found a man - probably early 40s, she estimated - standing beside her.

"Are you gonna get up there and dance?" he said, perusing her body.

"Well, aren't you sweet," Samantha said, doing little to hide the sarcasm.

"Can I buy you a drink?" the man asked.

"Thank you, but no," she answered. "I'm sort of waiting for someone."

Surprisingly, he took the hint.

"Have a good night, beautiful," he said, before walking away.

Samantha had to admit the compliment buoyed her confidence. The man didn't appear to be inebriated. His speech wasn't slurred. It was dark, but certainly not pitch black. Maybe she did look as good as she felt tonight. Smiling, she whirled to check on Jim.

Her step-brother was gone. So was the dancer he'd been watching. Concern bubbled to the surface of her consciousness, but she calmed herself. She'd begun to wonder if perhaps he'd taken the girl in back to get a lap dance when she saw him stumble out of the bathroom. Returning to his friends, he downed his beer; the second she'd seen him finish.

She knew she'd have to make her move now. If she waited too long, he'd be sloppy drunk, which would not only make him boisterous - and more of an asshole than usual - but might also render him unable to answer the bell, so to speak. Samantha stood up and walked around the bar.

Rick noticed her first. He was cute, and seemingly less brutish than the others. While certainly no Einstein, she'd actually heard him talk about reading a book. He must have said something to the others because a moment later, three more heads rotated to look at her. Their eyes traced up and down her body.

Samantha nearly balked. If any of the men recognized her she could be in real trouble. For a split second, panic raced through her. Stealing herself, even as her heart raced, she continued.

"Hi," she said, loudly, as she approached the stool next to her step-brother.

He didn't reply.

"Is this seat taken?" she asked.

"Uh, hi," Jimmy stammered. "No."

"Mind if I join you?" Samantha asked.

"Not at all," Tony answered, elbowing Jimmy.

Flashing a smile, she sat down.

"I'm Samantha," she said.

"Jimmy," he said.

"No, Samantha," she teased.

The look of confusion on his face almost made her laugh. Finally, it dawned on him.

"I mean, I'm Jimmy," he said.

A grin creased her lips. He named his friends, cocking a thumb over his shoulder, and she gave the trio a short wave.

"Do you come here often?" Jimmy asked.

Samantha almost choked trying to keep the word "seriously" from escaping her throat. While she hadn't come here expecting Algonquin Round Table-level discourse, the cliché still surprised her.

"Occasionally," Samantha managed to say.

"I've never seen you before," he confessed.

"Do you spend a lot of time here?" she asked, already knowing the answer.

"No," he lied. "Not really."

"Can we buy you a drink?" Tony asked.

Samantha held up her glass as she shook her head.

"Second round?" Tony said more than asked.

"No, thank you," she said. "I don't want to lose control and do something crazy."

"Like what?" Jimmy inquired.

"Get up there and dance?" Phil asked.

"Oh, no," Samantha said, nodding toward the stage. "I can't bend like that."

Three of the men followed her gaze. The girl in front of them had her cheek on the floor, and her ass high up in the air. Focusing on the small group, she rocked back and forth a few times. They cheered, and threw several dollar bills at her. She gyrated wildly, shaking her bottom, which brought applause and additional money.

From the corner of her eye, Samantha noticed Rick staring at her. He didn't say a word, but seemed to be concentrating, as if he'd seen her before and was trying to put a name with the face. Samantha worried he might - given enough time - recognize her. Even though the majority of her brain told her this was highly unlikely, she decided to move things along and avoid possible detection - at least for now. Her attention returned to Jimmy as the dancer continued feigning having sex doggy style.

"That's my favorite position," she said, above the music.

Jimmy's mouth dropped open.

Not exactly subtle, she thought.

"Mine, too," he croaked, before taking a pull from his latest bottle.

"What a surprise," Samantha almost whispered.

Jimmy didn't hear the comment, and leaned in close. He was about to ask her to repeat herself, when she took the straw in her mouth to sip her drink.

"You have beautiful lips," he said, leering at her.

Samantha decided it was now or never.

"Why don't we go out back, and I'll show you some of the things I can do with them?" she purred.

Jimmy looked as if she'd just smacked him in the face. It took him a moment to recover.

"What about my friends?" he asked.

Not understanding what he meant, her head tilted quizzically.

"I'm certainly not going to blow all of them," she said with an edge in her voice.

"No, I didn't mean that," he blurted. "I just...I didn't want to disappear on them."

"They look like big boys," Samantha observed. "I'm sure they can take care of themselves."

She slipped off her stool, and was about to turn, but another idea hit her, and she decided to see how far she could push this.

"I'll tell you what," she said, leaning close to Jimmy. "If you want, they can watch."

His eyes went wide, and she could almost see the questions clanging around in his head. He gaped at her. She winked, confirming she'd really said what he heard. Jimmy spun around and conferred with his friends. One by one, they examined her; heads nodded.

"OK, then, let's go," Samantha said, withdrawing from the bar.

The four men followed, nearly tripping over each other. Going out the rear door, Samantha examined the parking lot. There were several darks spots, and she led the group toward the one farthest from the exit. Grabbing Jimmy, she forced him to the wall. The others moved in close.

"You guys stand there," she ordered, pointing to a portion of wall about 10 feet away.

"That far?" Tony protested.

"Jimmy and I could go back to his place without you," she threatened.

The three men grumbled, but did as they were told.

"Good boys," Samantha scoffed.

Facing Jimmy, she mashed her mouth against his. He tasted like beer. For more than a minute, their tongues danced. Even half-drunk, she found him a good kisser. To the delight of his friends, Jimmy's hands squeezed her ass. Her right hand rubbed his cock through his jeans, and his fingers crept into her crack. As they migrated downward, she pulled away.

"OK," she said. "Let's see what you've got to work with."

Samantha waited impatiently as Jimmy fumbled with his pants. The other men hooted at his difficulties.

"So, are you tough guys gonna just stand there, or do I get to see what you're hiding in those pants?" Samantha teased.

"We'll show you ours, if you show us yours," Tony said.

"This isn't the fifth grade, honey," Samantha chirped.

"Well, I ain't shy," Tony retorted, grabbing his zipper.

The other two hesitated for a moment, then joined him. Not wanting to ruin the knees of her leggings, Samantha squatted in front of Jimmy and inspected his now exposed penis. He was already hard, and she guessed him to be about six inches long. She wrapped her right hand around the shaft, judging its girth. It was a good size, she judged. Not too big for the next step in her plan. But, that was later she reminded herself. First things first. Jimmy moaned as she stroked him gently.

"Easy," she whispered. "Just relax."

Samantha leaned in and took the head of his cock in her mouth.

"Oh, yes," Jimmy sighed, shifting forward a fraction.

Placing her hands on his hip bones, Samantha eased him back to the brick. She took him deeper, letting in half his length as her tongue swirled around it. Her lips slid over the taut skin, admitting a little more of him each time she rocked forward, until her nose touched his trimmed pubic hair. He groaned as she stopped, holding him there nearly half a minute; the tip of his cock in the back of her throat.

"You like that?" she asked, temporarily abandoning him.

"Yes," he said. "Keep going."

She swiveled to face the three men, all with their pants around their thighs. Even from this distance, she could see Tony had nothing to be timid about. His member had to be at least eight inches long. He stroked himself slowly, his right hand moving up and down deliberately. The other two were of average length, though Phil appeared to be very thick, and Samantha doubted she'd ever be able to fit him, either in her mouth or her ass. Jimmy placed his right hand on her head, trying to guide her back to his dick. She slapped it away.

"I don't need your help," she scolded. "I know what I'm doing."

"Sorry," he moped.

"If you don't like it, you can leave, and I'll blow one of them," she said, pointing toward his friends.

"No," Jimmy said. "Please. I'm close."

"Damn, she's feisty," Tony chimed in.

Despite her threat, Samantha returned her attention to little Jimmy, enveloping him once more; taking him deep; moving faster now, wanting to finish this. Her right hand drifted to his balls, and she massaged him gently. It didn't take long. She felt his scrotum tighten, and Jimmy mumbled something.

"Mmmm, hmmm," Samantha hummed.

Jimmy's cock swelled. She pulled back, sealing her lips around the head as she stroked him hard and fast. She closed off her throat just as he erupted, shooting multiple streams of hot, salty cum. His body convulsed violently, and she struggled to stay with him as he fired again. The load threatened to overflow her mouth, but she remained in place.

The others cheered and encouraged Jimmy as he came. Samantha heard one of them croak weakly that he was about to cum. She tried to angle herself enough to see this. Phil's first salvo launched into the air, and landed several feet away. Samantha was impressed by the distance it traveled. As Jimmy wilted, Rick exploded, his knees buckling slightly as he came. His jizz didn't travel very far, but there seemed to be an enormous amount, creating a small puddle at his feet.

"I win," Tony proclaimed in a booming voice. "Last man standing."

"Could you say it a bit louder?" Phil admonished. "I don't think the people inside heard you."

Samantha looked up at Jimmy. She let him slip from her mouth, careful not to spill his seed. Puckering her lips, she gave the tip a last kiss, then leaned to the side and spit out his cum, making sure to avoid her pants and shoes.

"Spitters are quitters," Tony said.

"Yeah, well, I don't know where he's been," Samantha said.

Tony scuttled over to stand next to her. When she straightened herself, she found his cock just inches from her mouth. She ducked away.

"What the fuck are you doing?" she raged, scrambling to her feet.

"It's my turn," he said.

"You'd better ask one of them to suck it," Samantha fumed, indicating Rick and Phil, "because I'm certainly not going to."

"Are you kidding me?" he said.

"Uh, no," she retorted. "I said you guys could watch. I didn't say I'd blow the whole bar."

"Man, you awoke the beast," Tony said, gesturing to his erection, "and now you're just gonna leave it high and dry?"

"Sorry I'm not sorry," she mocked.

"Motherfucker," he shouted.

Samantha tugged at Jimmy's arm as he closed his pants.

"Come on, let's go to your place," she suggested.

They walked past the other three, heading into the light.

"You're gonna leave us for her?" Tony howled.

"Damned right I am," Jimmy laughed.

"He's a dick," she said once they got farther away.

"When he's been drinking," Jimmy admitted.

Samantha almost made a mistake. She began walking toward her car, but quickly realized Jimmy might recognize it. For a moment, she worried he might not be able to drive. She faked a trip, pushing herself against him, trying to knock him off balance, but he steadied her without falling himself.

It'll have to do, she thought.

When they arrived at her mother's house, Jimmy told her she needed to be quiet lest she wake his parents. Samantha nearly made a comment about him still living at home, but held her tongue.

"Can I use your bathroom?" she asked in a hushed tone.

He led her to the hallway, then pointed her in the right direction.

"I'll be in the kitchen," he said as she walked off.

Samantha took several minutes to urinate, clean up, and then use some of the mouthwash she found on the counter. After looking into her eyes in the mirror, steeling her nerve, she flipped off the light, opened the door, and tip-toed to the kitchen. In the darkness, she could barely make out Jimmy standing by the sink, drinking a beer.

"Want one?" he asked.

She smiled as the plan in her brain modified slightly. Shaking her head, she walked over to him.

"Can you get that dick hard again?" she cooed.

"If you help," he said.

"Is that a challenge?" she asked, pressing herself to his chest.

He didn't answer. Taking another swig, his eyes followed her as she sank to her knees in front of him.

"Let's go to my room," he suggested, placing the bottle in the sink.

Samantha shook her head at him. Her right hand patted the front of his pants.

"Here," she insisted, trying to work his belt.

"We can't make any noise," he reminded her.

By the time Samantha got his jeans open, the crown of Jimmy's cock peeked out above the waistband of his underwear. She licked it roughly, and he groaned.

"Shhh," she teased.

Freeing him, she took the head between her lips. Without hesitation, she once more buried her nose in his pubic hair, and held herself there; feeling him harden in her mouth, until it again filled the back of her throat. She labored to adjust her own cock - stiff and desperate for attention - as it lay trapped uncomfortably in her skin-tight pants.

"Your mouth is so hot," Jimmy croaked.

Grabbing his shirt, Samantha steadied herself as she stood up.

"Wanna know what else is?" she asked, her voice raspy in his ear.

He nodded as his hands closed on the cheeks of her butt, squeezing hard. They began working their way around toward the front, and she turned quickly, wiggling until she felt his cock poking her ass through the pleather. Placing her hands atop his, holding them as she shifted her hips left and right several times; grinding into him.

"Oh, God," Jimmy exhaled.

"I want you to put that in my ass," Samantha told him.

In no position to protest, Jimmy remained silent as she spun them, leaving her against the sink, him behind her. She leaned over to retrieve her clutch. Opening it, she fished around for a moment, then pulled out a condom, and a small bottle of water-based KY.

"Put this on," she instructed, handing Jimmy the prophylactic.

Edging her pants down a few inches - careful, despite the darkness, to avoid exposing her secret - she poured some of the lube on her fingers, then shoved them between her cheeks. Dispensing more of the viscous goo, she caressed his cock, greasing him - at the same time checking to make sure he'd actually donned the rubber.