Becoming Samantha Ch. 01

Guiding his penis to her, she gasped when the tip touched her hole. He tried to push hard, forcing himself inside her, but she held him firmly as she bent over the sink. She had no intention of letting him hurt her.

"Easy," she hissed. "Gently."

Jimmy complied, and her slick fingers gripped him as her sphincter slowly opened. Samantha emitted a low whine as he steadily slid into her, stretching her hole.

"Shiiiiit," she moaned.

He had two inches inside her before he stopped. Pulling back a fraction, he nudged himself forward again, sinking farther into her ass. It took two minutes to work his entire length into her. By that time, they were both breathing in great sobs; fighting for air.

"It's so tight, baby," Jimmy murmured.

"Do you like my ass?" Samantha asked.

"Absolutely," he replied, his voice quivering.

"Tell me," she insisted.

"It's fuckin' perfect," he stammered as he slapped her right butt cheek. "I want more."

Samantha couldn't help herself. She shimmied her hips, working her pants down enough to free her own cock. The fingers of her right hand traveled over the tip, collecting the pre-cum leaking out, and then wrapped around the hard shaft. She jerked herself urgently as Jimmy thrust himself into her, pinning her as he filled her rectum.

"That's it, Jimmy," she pleaded, "fuck me."

"Yesss," he growled, grabbing her hips, and shoving himself deeper.

He moved faster, sliding in and out. She fought to steady herself with one hand, while stroking her cock with the other. She was close. The perversity of what she was doing - who she was doing - and of what she'd done earlier, letting the other men watch her, was driving her crazy. The heat of him inside her; the suction created by his movements; the pleasurable pain; it all drew her inexorably toward the temporary oblivion of orgasm.

"Harder, Jimmy," she said, loudly.

"Shut up," he ordered.

"Do it," she demanded, pushing herself back toward him as he drove forward.

Only a minute later, she felt his shaft swell, further expanding her asshole.

"I'm gonna cum," he announced.

"Give it to me," Samantha urged. "Right in my ass."

Jimmy grunted as his body convulsed, and she felt his cum fill the condom. The sensation carried her past the point of no return. Even as he leaned over her back, bucking as he climaxed, Samantha struggled to straighten slightly before she exploded, spraying her cum onto the cabinet in front of her. Their sweaty bodies trembled together for several long moments.

"Jesus Christ," she panted.

Without warning, or attempt at delicacy, Jimmy let himself slip from her hole.

"Fuck!" she spat.

He stumbled backward to slouch against a counter.

"Sorry," he offered. "Are you OK?"

Her body shuddered, as aftershocks of her orgasm rolled through her.

"Did you cum?" he asked.

"Yes," she answered, rolling her eyes.

If you have to ask..., she mused.

Samantha used the sink to support herself, afraid her knees might buckle.

"That was fantastic," Jimmy said.

"Mmmm," Samantha responded. "I'm glad you liked it."

For another minute, they remained in the darkness, silent; their breathing and heart rates slowing.

"I have to freshen up," Samantha said, finally; discreetly pulling up her leggings to cover herself. "Why don't I meet you in your bedroom?"

Her legs weak, she made her way to the bathroom once more. She took a few deep breaths, then cleaned herself; wiping away the last of the semen dripping from her cock before sitting on the toilet to complete her cleansing. She glanced at the clock. It was nearly two in the morning.

"Damn it," she muttered.

Pulling out her phone, she went on-line and arranged a ride back to the bar. While waiting, she removed her make-up with Kleenex and water. Looking at herself in the mirror, she wondered if she was ready for this. She wasn't sure. Leaving the bathroom, she shuffled through the darkness to Jimmy's door.

A warning sign popped up in her brain: How did she know where his room is? She hadn't asked. Did it really matter at this point? her mind continued.

"Well, too late to worry about it now," she whispered as she quietly pushed the door open.

Her concern was unnecessary. Jimmy lay atop his bed, naked, and sound asleep. Samantha's plan to reveal herself seemed in jeopardy. But, as she lamented this, a new - safer - idea hit her. She tip-toed to the bed, and sat down on the edge.

"Jimmy, are you awake?" she asked, softly.

Receiving no reply, she reached out to the nightstand, and turned on a lamp. Her eyes traveled over his sticky penis, now wilted and resting between his thighs.

Perfect, she thought.

Again retrieving her phone, she activated the camera, held it at arms-length, and snapped a dozen pictures of herself with Jimmy. In some, his face and hers clearly visible. In others, her face - tongue sticking out - next to his cock. She removed her wig for several of the photographs.

He didn't wake, and she almost laughed as she walked out the door, pulling it closed behind her. She took the time to scrub her cum from the cabinet and floor in front of the sink - no sense leaving a mess for her mother to find - then exited the house, and paced along the sidewalk for several minutes before her ride arrived.

Late in the morning, Sam opened his eyes. Sunlight streamed into his room, and he squinted. After a few moments of adjustment, he rolled over. Reaching for his phone, he checked the time. He scrolled through the pictures he'd taken before leaving Jimmy.

"They'll do nicely," he said, out loud.

Hoping his step-brother would be awake, he texted.

"Have fun last night?"

It took two minutes to get a reply.

"Yes. You should have come."

"I did." Sam replied.

"What?" Jimmy questioned. "I didn't see you."

"Did you get lucky?" Sam asked, needlessly.

"Sure did," Jimmy bragged. "She was fucking hot."

"Nice," Sam allowed. "Going to see her again."

"Dunno," Jimmy said. "I hope so. Her ass was perfect."

Sam smiled, then sent the pictures.

"Where did you get those?" Jimmy asked.

"Look closely," Sam urged.

"What the fuck?"

He could almost hear Jimmy screaming the words.

"What's wrong?" Sam asked.

"WHAT THE FUCK DID YOU DO?"

"I didn't do it alone," Sam said.

"I didn't. I was drunk. It was a girl."

"It was me, and you fucked my tight little ass," Sam told him.

"I don't understand," Jimmy said.

"I'm transgender," Sam confessed.

"You can't be," Jimmy countered.

"Of course I can," Sam asserted. "And, I'm in the process of transitioning."

"Leave me alone," Jimmy shot back.

"You said my ass was perfect," Sam reminded him.

"No," Jimmy protested.

"Sure you did," Sam said. "Scroll up a few lines."

"That's not you," Jimmy claimed.

"It's pretty clearly you and I," Sam wrote. "And, if I ever again hear you use words like faggot, fairy, tranny, or queer; or hear you talk shit about LGBTQ people, I will send these pictures to your father, and your friends. You know, the ones who watched me blow you outside the strip club."

Jimmy didn't reply, and Sam wondered if he'd had a heart attack. After waiting another 10 minutes, he sent one more text.

"Thanks for the good time."