Becoming Samantha Ch. 02

Story Info
Revenge, Ruin, and Revelation.
3.6k words
4.56
20.2k
13

Part 2 of the 4 part series

Updated 06/08/2023
Created 08/19/2016
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Sam finished building the webpage with a day to spare. After triple checking for bugs, he uploaded it. Twisting and turning in his chair, he stretched, and then smiled as he thought about the payment he'd receive for his efforts.

Glancing at the calendar, he realized 10 days had passed since he'd heard from his homophobic step-brother. They didn't communicate regularly, but Sam figured Jimmy would say something about being tricked into receiving a blowjob from his transgender sibling while three of his friends watched and jerked off, then – later that same night – having anal sex in his parent's kitchen – even if it were just a threat to never tell anyone about it.

Sam had to admit – as dangerous as the situation was – it was also a turn on. Sucking off one man as others pleasured themselves had ignited a fire in him. At this point, he was fairly certain he couldn't have Jimmy again, but his friends were a different story. They, he was sure, would line up to have Samantha on her knees in front of them. He decided to extend his revenge – or, maybe just deepen his enjoyment of it.

He logged online – using his Samantha persona – and clicked on Jimmy's profile. Browsing through his friends list, it didn't take long to find Tony, Phil, and Rick; the exhibitionist/voyeurs from the previous week. A plan formed in his mind, and with time to kill before his next project was due, he decided to have some fun. Although Tony – according to FS – had a girlfriend, Sam sent him a message.

How does that arrogant prick have a girlfriend? he wondered.

While waiting for a response, Sam took a shower, taking the time to shave. Returning to the computer, he found – as expected – a reply. After trading a dozen IMs, Samantha asked Tony if he'd like to meet. He informed her he was stuck at work – a car dealership – until 10:00pm. Samantha offered to meet him there, and he quickly agreed.

Sam dressed – donning a loose, black Metallica t-shirt, tight blue jeans, and black combat boots – applied a little make-up, and put on a brunette, bob-cut wig – completing his transformation into Samantha. She examined herself using the full-length mirror in her bedroom. Happy with what she called her "tomboy" look, she picked up her keys, and then headed for the door.

Not wanting Tony to see her car, Samantha parked at Barnes & Noble, three stores away from the dealer. She wandered into the lot, and stopped to browse a few cars while meandering toward the back. Tony walked up as she pretended to inspect a Honda Odyssey.

"You don't strike me as a mini-van kind of girl," he quipped, his eyes lingering on her ass.

"Depends on the situation," she allowed.

"Wanna take a test drive?" he asked with a grin.

"How much room is there?" she asked.

"Let's find out," he said.

Tony grabbed the handle, activating the automatic side door, and waved a hand toward the interior.

"You first," she insisted.

He fumbled to adjust the middle seat, then scrambled in, moving to the rear bench. She followed, plopping down on the fabric cushion, leaving two feet between them.

"Plenty of space," Tony said, spreading his knees to illustrate his point.

"It seems pretty big," Samantha replied, staring at his crotch.

"Oh, it is," he bragged. "More than enough to get the job done."

"What is that?" she pressed.

"Making you cum," he said, grinning.

"I don't know," she clucked, dismissively.

"I'm very good with it," he assured her.

"If you do say so yourself," she returned.

"Never had any complaints," he said.

"I'll bet," Samantha mocked, rolling her eyes in the shadows.

Someone knocked on the window, and a face appeared in the doorway.

"Hey, Tony; it's closing time," the man reported.

"Alright, John," Tony said. "You guys can take off. I'll lock up when I'm done with this customer."

"Sounds good," his associate chirped, and disappeared.

"So...," Tony teased, leering at Samantha.

"Alone at last," she responded.

"I'm sorry, did you want someone to watch?" Tony teased. "Like with Jimmy?"

"Funny," she said, sarcastically.

Samantha slid closer and placed her hand on his right knee.

"Why don't you get it out?" she suggested.

Tony clawed at his belt, unfastened his pants, and then lifted his butt in order to push them to his knees. Samantha spun to straddle Tony and kissed him. He tasted like cigarettes, and immediately tried to shove his tongue in her mouth. She withdrew, pinning his shoulders to prevent him from following.

"You taste good," he growled.

"Thank you," she whispered, forcing a smile.

Tony reached out to touch her chest, but she avoided him, rolling off his lap as he groped her ass instead.

"Someone's waking up," she observed, gazing at his stiffening cock.

"He wants a kiss, too," Tony said.

"Maybe I should leave so he can go back to bed," Samantha said.

"No," he protested, lunging for her.

Again, she was able to fend off his assault.

"Put your hands behind your head," she ordered.

He hesitated for a moment, then complied.

"That's better," she said.

Cautiously, Samantha approached, leaning over as she did so. Tony parted his legs as far as his pants would allow, and the fingers of her right hand brushed his shaved balls. The musky scent of him filled her nostrils. Not an overwhelming or bad smell, but the aroma of a man.

Drifting closer, she licked the tip as her hand wrapped around the shaft. Tony exhaled deeply as she began stroking him while her lips closed around the head. Moving slowly at first, Samantha soon increased the speed and intensity of her efforts, working his eight-inch length into her mouth.

For several minutes, her head bobbed; rising and falling as she consumed him. She was deliberately sloppy, letting her saliva coat his cock, then roll down to his balls, and onto the seat. Tony moaned as she manipulated him, and Samantha realized this wouldn't take much longer. She cupped his scrotum, squeezing gently, but firmly.

"That's it," he croaked, as his right hand fell to her back, and drifted along her spine.

He tried to slide his fingers inside her jeans. Samantha shifted her body, allowing them to reach the top of her crack. She wanted more, but silently reminded herself to stick to the plan.

"Mmmm," she moaned, the vibrations rolling through him.

Tony let out a long sigh as the head of his cock slid into Samantha's throat. She held him there as he squirmed. His balls tightened, he muttered something unintelligible, but whose meaning was unmistakable, and clawed at her flesh.

"Oh, yesss," he hissed.

Samantha abandoned him, popping up to her knees.

"I have to go," she said, loudly.

"What?" Tony blurted, confused. "I'm cumming."

A grimace of pain twisted his face as he fought against nature. He tried to seize Samantha, intending to pull her back to him. She avoided his grasp as a jet of hot, white cum erupted from his cock.

"Shit," he grunted, covering the tip with his hands, trying to prevent a mess.

For a few moments, Samantha watched his body shudder as the sticky jizz coated his fingers and trickled down the shaft, then she scuttled toward the door.

"Where the fuck are you going?" he demanded, his voice strained.

"Home," she chirped, stepping to the blacktop.

"What the fuck?" he shouted. "You didn't finish me."

"Did you cum?" she retorted.

He held out his semen-coated hands, and surveyed his lap.

"Then what are you complaining about?" she argued, facetiously.

"You should've kept going," he protested.

She shook her head slowly.

"I wanted to nut in your mouth," he cried.

"Awww," Samantha teased. "What a gentleman you are."

"God damned bitch," he spat.

"Well, I'm sure your girlfriend could do a better job," she quipped. "Of course, if she finds out about this, she might not."

Samantha straightened her clothes as she sauntered away, listening to the string of curses emanating from the back seat. She laughed all the way to her car. It took several minutes for her pulse to slow. Initially afraid Tony might follow her, she realized he was probably still trying to clean and dry the seat of the van. She let out a long breath, checked her hair and lipstick, and then drove off, preparing herself for phase two of her plan.

Half an hour later, across town, Samantha entered a parking lot empty but for one other car...Phil's. Her boots clumped across the pavement as she approached the entrance. The glass doors were locked – as she had expected. She rang the bell for Security. As she waited, her eyes traced over the carved stone letters above the portal – Museum of Art.

"That idiot, in a place like this," she said, softly.

It took several minutes for Phil to appear. He shuffled around the corner of an exhibit, tucking his uniform shirt into his pants. Depressing the push bar on his side of the door, he opened it half-way.

"Can I help you?" he asked, obviously annoyed to have been interrupted during whatever intellectual pursuit he'd been engaged in.

Samantha looked at him for a moment.

"Do you remember me?" she asked, finally.

"Should I?" he returned.

"Outside Double Dee's, the other night..." she prompted.

His eyes narrowed as he considered her.

"Oh..." he said. "Sure...Sandy, right?"

"Samantha," she corrected.

"Yeah, that's it," he agreed.

"Uh, I know," she scoffed, barely audible.

"What are you doing here?" he asked.

"Well," she said, gazing up at him, "I was thinking about how thick your dick is. And, I was wondering if you might let me see it up close."

"Really?" he asked, his eyes glazing over.

"Of course, sweetie," she baited.

"I think I can do that," he allowed.

He began to step out the door.

"Where are you going?" she asked.

"My car," he answered. "There are too many cameras in here."

"Everywhere?" she countered.

"Almost," he told her.

"What about a breakroom?" she asked. "Or, a bathroom?"

"We have both," he admitted.

"Is anyone else here?" she asked.

"Nope; I'm it until midnight," he explained.

"Oh, we don't have much time then," Samantha noted.

Phil paused for a few seconds.

"So...," she coaxed.

He held the door open for her. She entered, and he led her through the lobby, made two turns, and approached a men's room. Samantha walked in and made her way to the handicapped stall. Turning, she positioned herself sideways on the toilet seat as Phil slid the lock into place.

"OK, big boy," she urged, "let's see it."

"Are you going to show me yours?" he challenged.

"Not right now," she replied.

Frowning, he moved closer, then slumped against the pale green tiles covering the wall.

"Come on," she prodded. "Time's a wastin'."

Phil grappled with his pants, finally getting them open. Lowering his once-white boxers, he exposed a limp blob of hairy flesh, the head shrunk back in the foreskin.

"I thought it was bigger," Samantha lamented.

"It is," Phil said, defensively. "I'm a grow-er, not a show-er!"

"Well, what does it take?" she challenged. "Don't you find me attractive?"

Samantha leapt to her feet as if she were going to leave.

"No," he wailed.

"What?" she snarled.

"Don't go," he said, on the edge of pleading.

She almost laughed.

"I thought you meant I'm not pretty," she said, coyly.

"You're really hot," he blubbered.

"Do you like my ass?" she asked, spinning around, and bending slightly to accentuate it.

"Fuck, yes!" he boomed. "Can I touch it?"

Samantha shimmied closer, allowing him to grope her. He squeezed hard, and she yelped, but remained in place. Wrapping his right hand around his cock, Phil began rubbing along the shaft. His eyes devoured her as he manipulated himself. Less than a minute later, he was completely hard.

"That's what I remember," Samantha cooed, as she admired his cock.

It stood out a little more than six inches, and had to be three inches across.

"Oh, my God," she exhaled.

He used long, deliberate strokes, letting his fingers slide from his scrotum to the head – then running them over the tip. Phil's mouth hung open, and his breath came in ragged gulps as he gradually increased his pace.

"Do you want to help?" he asked.

Without answering, Samantha reached out, and he moaned as she squeezed his penis.

"Jesus," she marveled. "It's so fucking thick."

"See if you can fit it in your mouth," he commanded.

She glanced up at him, momentarily unsure of what to do.

"I don't think it will," she said, truthfully.

"Try," he insisted. "Please."

Samantha squatted in front of him. Leaning forward, she stuck out her tongue. Phil whimpered when it touched him. She licked her way downward, then back up to take the swollen head between her lips.

"Shit," Phil wheezed. "That's it."

Without warning, he seized her head with both hands, and tried to thrust himself into her mouth. She clutched his wrists and hastily retreated, afraid he would tear off her wig.

"I know what I'm doing," she scolded.

Phil shrugged.

"Keep your paws to yourself, or I'll stop," she instructed.

"Sorry," he sniveled, lets his arms fall to his sides.

Samantha waited a few moments – making sure Phil wouldn't try again – then returned to her task. He squirmed as her warm, wet mouth enveloped the first two inches of his cock. Her lips stretched, gliding along the taut flesh. For a moment, she thought of how wonderful this monster would feel in her ass, but admitted to herself she had no chance of taking it all.

Maybe with someone I trusted, she mused, silently.

She continued working him; one hand cupping his scrotum, the other stroking, while flicking her tongue over the head. Phil's breathing quickened, and Samantha worried he might cum soon. She let his cock slip from her mouth.

"I want to fuck you," he announced, staring at her.

"There's no way you're sticking this thing in me," she retorted.

"Come on," he whined.

"You'd split me wide open," she explained.

"I won't hurt you, baby," he groused.

"Maybe next time," she said, trying to lighten the blow of denial by letting him think he'd ever have another chance with her.

Releasing him, Samantha returned to the toilet.

"I want to watch you jerk it," she purred.

"That's it?" he grumbled.

She nodded, gazing up into his eyes. He hesitated, weighing whether or not the delay might convince her to help him, then complied. Lubricated by her saliva, his right hand slid back and forth along slick shaft. He glared at her as he increased the pace of his movements.

"Come on, Phil," she insisted. "Do it."

"I'm close," he announced, aiming himself at her.

Samantha sprung to her feet, fearing he intended to cum on her. She slipped behind him and reached around to fondle him.

"Let's see it," she demanded in his ear. "Show me how far you can shoot."

Phil groaned loudly as his balls tightened. His body stiffened as she hugged him.

"I'm gonna cum," he jabbered.

"Yesss," she ordered. "Give it to me."

A gurgle escaped his throat, then his body convulsed, bucking wildly as a jet of cum shot across the stall, splattering on the far wall.

"Fuck, yes!" she roared.

Phil struggled for air as he fired again and again.

"More!" Samantha raged as his body bucked, slamming her against the tiles.

The blows stunned her, and she lost her grip on him. Phil shuddered, his knees weakened, and he fought to remain standing. Samantha recovered quickly, and guided him as he staggered backward, ensuring he wouldn't collapse. Inspecting his wilting cock, she noticed semen dribbling out of him.

"Holy shit," she cried. "You're still cumming?"

An idiotic grin split his face, forcing Samantha to suppress a laugh. Raising her eyes, she examined the mess he'd made. Cum oozed down the wall, then dripped to the floor, which revealed a trail of goo leading back to Phil's shrinking form.

"That was fantastic!" she exclaimed.

He mumbled something Samantha interpreted as agreement. She became aware of how hard she was – her own cock uncomfortably constrained by tight denim. Realizing her panties were wet with pre-cum, she rubbed herself.

"I can help you with that," Phil offered.

"What?" Samantha asked, snapping out of her momentary fog.

"You need to cum," he said, not telling her anything she wasn't already keenly aware of.

"I do," she affirmed. "But, not here."

Her hands covered her crotch.

"I have to go," she stammered, moving toward the door on trembling legs.

Phil, his pants bunched around his knees, tried to follow. She bolted out of the restroom. Managing to remember her way out, she fled into the parking lot. Looking back, she couldn't see Phil. Fortunately, he didn't pursue her, and Samantha let out a long burst of giggles as she approached her car.

Driving away from the museum, her free hand fell into her lap. She rubbed her throbbing cock, and she considered finding a dark spot where she could stop long enough to jerk off. Her mind buzzed. She wondered if she should take a chance and contact her step-brother. Maybe she could convince him to fuck her again. Or, perhaps call Rick – the third member of the trio who'd watched her blow Jimmy. She even pondered trying an occasional "friend with benefits," but, checking the clock, realized it was getting late.

"Fuck me sideways," she shouted.

The irony made her smile.

"Well, that would be the idea," she quipped.

Dejectedly, Samantha accepted that she'd have to wait until she got home, and then take matters into her own hands – so to speak. She drove as fast as she thought she could get away with. Bounding up the stairs, she rushed into her apartment, barely remembering to lock the door before heading for her bedroom.

She forced herself to slow down and relax. Carefully, she spread a towel on the edge of her bed. After removing her boots, she tugged at her clothes, blindly tossing them toward a chair in the corner.

Ignoring her dick for another moment, she retrieved her silver bullet and a bottle of lube from the nightstand. Squeezing the tube, she allowed a dozen drops of the viscous liquid to coat the vibrator. Turning, she positioned the toy and lowered herself, guiding it to her asshole. Despite her own desire, and the anticipation, she gasped when it penetrated her, steadily pushing past her sphincter.

"Fuuuck," she sobbed as it slid inside her.

When the cheeks of her ass reached the bed, she began stroking herself – hard and fast; needing to cum; not wanting to delay her own pleasure. The device pulsated inside her as she thought about the two cocks she'd seen spurt that night. And, though she knew she'd never fuck either of the men they were attached to, she enjoyed the memory; the power she'd had over them, the passion driving them.

Her cries echoed off the walls, and she came in less than two minutes; shooting cum up onto her stomach and chest. Gingerly lowering herself to the bed – the vibe still inside – she envisioned her next adventure, and caressed her sticky cock until it hardened again.

Samantha waited two days before calling Rick – though it required a great deal of patience to delay that long. She dialed carefully, and identified herself to the deep voice that answered.

"I've been expecting your call," Rick said.

"You have?" she asked, caught off-guard.

"Sure," he explained. "I hung out with the guys last night. Tony and Phil were busting your brother's balls about how you blew them both."

"My brother?" Samantha repeated, her voice betraying her surprise.

"Yes," he said. "I know who you are, Sam."

She remained mute; stunned by his revelation.

"Don't worry," he assured her. "I didn't say anything to the others."

"Wh...why? How did you know?" she asked, just above a whisper.

"It took a little while," he admitted. "The lights in the strip club didn't help. But, eventually, I recognized your eyes."

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