[Patreon Exclusive] SHAMELESS SHEMALE: Chapter 3 (Patreon)

“Hello there,” a female voice said behind him.

Jerry swung around to face a tall, beautiful woman. She wore long tight leather gloves and long tight leather boots. Her lipstick was dark red and she was wearing a tight, sexy piece of lingerie.

She took a few steps towards Jerry. Her face was mostly obscured in darkness. Jerry took a few steps back, startled.

“Who are you? How did you get into my room?” he asked.

“We need to have a… Talk,” the woman said as she continued to approach the topless Jerry.

“A talk? A talk about what? I don’t know who you are.”

The woman stepped right up in Jerry’s face and then smiled. She was quite beautiful. Her eyes were a dark brown and she had perfect cheekbones and beautifully soft features. She smelled sweet, like vanilla.

“You don’t need to know who I am,” the gorgeous woman said.

She pushed Jerry back onto his bed and then planted her knees down next to him. She looked down, past her stacked chest at Jerry. She smiled again, showing off her sexy dark red lipstick.

“I—I have a wife.”

“I know, Jerry.”

“How do you know my name?”

“That’s enough talking, okay?”

Jerry would have spoken, but he was speechless, in shock. He stared up at the beautiful woman without blinking.

The woman gently placed her hands around the straps of her outfit. She slowly pulled them over her shoulders, letting them fall to the side. Her large breasts continued to hold up the spicy number.

The woman leaned forward and placed her head next to the frightened Jerry’s ear.

“I’m going to do bad things to you, Jerry,” she said. “Really bad.”

Jerry gulped and then started to sit himself up.

“This is ridiculous,” he said.

The woman pushed him back down. She was much stronger than she appeared.

“You only move when I tell you to, do you understand?”

“You can’t do this,” Jerry said.

“Oh, yes I can. You said so yourself.”

“What are you talking about?”

She leaned back in to his ear again. Her steamy hot breath tickled the back of his neck.

“You signed the paper, Jerry boy.”

Her leather-covered hand slipped down onto Jerry’s crotch. His body tensed up as she began to rub his member.

“W—What paper?” he asked.

The woman smiled.

“No talking,” she said again, squeezing his cock hard in her hand.

Jerry gasped at the attack and then suddenly remembered the paper the receptionist had him sign.

“What kind of fucked up hotel is this?”

“Rather than complain, why not try to enjoy your special vacation?”

She continued to rub his cock hard with her hand. She leaned in and placed the tip of her tongue at the base of his neck. Slowly, she moved up towards his ear, feeling the hairs quickly standing up as she passed.

Blood started flowing to Jerry’s member. The woman could feel it begin to throb and grow in her hand.

“Atta boy, Jerry,” she said.

“L—Let me up.”

“No can do,” the woman said. “Not until I’m done here.”

She sat back up, took her leather-covered hands and began to undo Jerry’s belt. She unzipped his pants and began to slide them down his body.

“For someone so against this, you sure aren’t putting up much of a fight,” she said.

Jerry began to sit up, but she pushed him back down hard.

“No fighting,” she said firmly.

She finished yanking his pants down around his knees, revealing his hardening cock. The woman took her hand and felt Jerry’s hard abs before moving south onto his slick cock. She squeezed his long member in her hand.

“Let’s get started, shall we?” the woman asked.

Jerry stared at her in silence as she stood up, leaned over the bed and picked up a set of handcuffs. She walked around to the head of the bed.

“Give me your hand,” she said.

Jerry didn’t move, so the woman reached out and grabbed his arm and pulled it to the headboard.

“Ouch,” Jerry said.

“Quit crying,” the woman replied as she cuffed his hand to the bed.

She began to walk around, cuffing his other appendages to the bed.

“I’m going to go to the cops, you know.”

“Shut up already,” she said as she finished tying Jerry up.

She stepped up on the bed and planted her boots on either side of Jerry’s ripped body. She looked down. Jerry looked unimpressed.

The woman started to pull her outfit down her body. First, her big boobs sprung out. Her nipples were big and erect. She continued to pull down her outfit, down her fit body, across her shaved pubes and over her…

Massively long cock. The woman had a long thick member that dangled over Jerry’s body. Jerry began to squirm, but he was stuck in place thanks to the handcuffs.

“Let me go!” he said. “Get away from me!”

She simply smiled at him.

“Help!” he yelled, “Help!”

“There’s no one here, Jerry. You ordered the fantasy package. You get the whole place to yourself with the fantasy package.”

“Keep that thing away from me.”

The shemale slowly sunk down to her knees and leaned over Jerry. Her long cock fell upon his chest. It felt hot as she slid it down his body, moving her face towards his long cock.

Jerry tried to escape again, but resistance was futile.

“Don’t worry, Jerry. I’m not going to hurt you. I promise you’ll love every second of it.”

The transgendered woman took Jerry’s cock in her hand and guided it into her mouth. She began to suck, back and forth, sliding her tongue up and down. She could feel his thick member expanding and throbbing against the inside of her cheeks as she rubbed his cock around her mouth. She tickled the tip of his dick with the tip of her tongue, tasting the first bout of pre-cum as it trickled out of him.

Jerry’s body remained tense as his manhood rose up high. The shemale placed her leathered hand under Jerry’s balls and began to rub and fondle them as she felt his cock expand in her mouth.

Jerry looked around the room for some sort of escape.

“What are you looking for, baby?” the shemale asked.

“P—Please let me go,” Jerry stuttered.

She smiled and continued going at his cock. She wrapped her hand around his shaft and began to quickly rub him off while she sunk her head down even lower to his asshole. She gently licked and tickled the rim of his anus while she jerked him off.

“Is that feeling good?” she asked.

Jerry didn’t respond. His bum hole breathed and flexed over the tranny’s tongue. She pushed her tongue into him and pulled it out, lightly penetrating him. Jerry’s cock had grown rock solid in the tranny’s mighty grasp.

With her free hand, the shemale reached down between her legs and began to slowly stroke her own massive dick. She squeezed it hard as she moved up and down the length of her titanic shaft as she ate out Jerry’s asshole.

Then, she got the first response from Jerry as he let out a mild sigh of relief. She could feel his body relax as she circled his asshole gently with her tongue. Her own cock had grown long and hard.

She slid her body back up the tied down Jerry’s. She sat up slowly, her big boobs hanging out gracefully, and lined herself up with Jerry’s penis. Then, she began to lower herself down. Jerry’s hard dick pushed up hard against her asshole for a moment before it successfully penetrated. Once past the first barrier, the dripping wet cock slid right on it, deep in the tranny’s butthole.

The shemale let out a long deep sigh of relief as her balls landed firmly on Jerry’s pelvis. Jerry was looking up at the woman. His face was red and his eyes were wide. The woman moved up and down Jerry’s long shaft, gliding gracefully along his slick member. Jerry watched as her firm tits bounced up and down and her long cock stood solid and high, pressed up against her soft tummy.

Jerry could feel the woman’s asshole breathing on his dick. It contracted and relaxed along the deep circumference of his penis. Rushes of hot energy began to flow through his body. His muscles began to relax as a deep sensation of pleasure grew in his cock.

And then, as if no longer control of himself, Jerry opened his mouth—

“I want to suck your cock,” he said.

The tranny stopped and smiled. She pulled her ass up, letting Jerry’s long cock slip and fall out. She stepped forward and dropped back down to her knees, lining her monolithic member up with Jerry’s mouth. Placing her leathered hand on the back of Jerry’s head, she slid her warm dick forward into his mouth. He opened wide, letting the thick beast slide in smoothly. He closed his eyes, obsessed with the feeling of her solid womanhood throbbing against his soft wet tongue. He slithered the tip of his tongue along the titanic member. It tasted so good. He couldn’t have enough of it. He closed his lips around his girth and began to suck, trying desperately to taste a little more of her cock. The transgendered woman began to slowly thrust her cock in and out of his wet mouth.

He sucked harder, needing that cock. He ran his tongue along the thick pumping veins of her member as the shemale’s ball sack slapped against his chin.

Jerry began to moan in a state of absolute pleasure.

“More,” he tried to say. “Deeper.”

The tranny shimmied her body forward, stuffing his mouth more as requested. He could taste her gloriously sweet pre-cum trickle down his tongue as the thick bulging tip squished against the back of his throat.

Saliva began to dribble out the sides of his mouth. He was so crazy for the cock; he was salivating like a wild dog.

Then, the strange woman pulled her long shaft out of his mouth. It dripped as long strands of saliva pulled their way between Jerry’s mouth and it’s thick tip.

She stepped off of the bed and walked around. Jerry watched carefully, his heart beating out of his chest with excitement. Stepping between his legs, she lined her sloppy dick up with Jerry’s tight, ready asshole.

He licked his lips.

“Do it,” he said. “Fuck me.”

The tranny stepped forward, pressing the head of her penis against Jerry’s tight asshole. It pushed through the narrow passage and Jerry’s head flung backwards. He let out a long sigh of relief as the massive shaft slid inwards, its harsh ridges rubbing every inch of his anus. It felt phenomenal, unlike anything he’d ever experienced. His cock incredibly became longer and harder as it sat on his rugged abs.

Slap! Slap! Slap!

The shemale began to thrust her body into Jerry, her thighs and ball sack slapping his legs hard with every revolution. Jerry let out a loud, prolonged moan as the thick girth of her dick stretched him wide.

“Oh, God!” he cried out in pleasure. “Oh, God!”

She worked away at his butt hole. Jerry’s handcuffs rattled as the woman-man increased her speed and intensity.

Squish! Squish!

The woman’s long cock slopped around inside of Jerry’s asshole, still covered in his own saliva. The beautiful shemale reached down and grabbed onto Jerry’s impossibly hard cock and began to stroke it as she entered and exited his deep body. She moved her arm fast, jerking him off at a rapid pace. The two parties were close to cumming. Their dicks were beginning to swell with cum. They both held back as hard as they could, prolonging the excellent moment.

The tranny’s pace continued to increase. Her intensity was wild. She slammed her body hard into Jerry, leaving dark red marks on his hard butt. Her cock throbbed intensely, sending ripples of pleasure through Jerry’s body.

Then, she pulled her cock out as Jerry began to scream out loud. His cock exploded and massive amounts of cum blasted out, way up into the air and back down onto his chest. The shemale’s cock began to shoot cum all over Jerry’s cock and his hard abs.

Jerry’s body trembled as the final bouts of pleasure from his climax fluttered out of his body. As the final ounces of cum oozed out of his cock, his body fell into the bed, limp. His eyes stared up at the ceiling, without blinking. His asshole was raw as a stranger’s cum dribbled down past it.

The shemale leaned down and picked up her little red panties. She slid them up over her cum dripping penis and then walked around to one of Jerry’s cuffed arms.

“I hope you write a good article, Jerry,” she said as she began to unlock one of his hands.

She threw the key onto Jerry’s cum covered chest. Jerry looked over at her, speechless—Lingering in the final shroud of his deep pleasure.

“And stop being such an asshole,” she smiled.

The woman turned to leave, never to be seen again by the used and abused Jerry. Once she was gone, Jerry looked down at his cum soaked body. He reached his free arm forward onto his chest and picked up the key for the rest of his cuffs.

~

Bing! An email appeared on Jerry’s home computer. He opened it.

It was from Denise Richards.

“Jerry,

I wanted to thank you for your wonderfully insightful and respectful article. I would like to apologize for my reaction at the press conference in Vermont…”

Jerry continued to read the sincere letter, surprised at the mean politician’s especially polite email. He smiled.

“They must have held a gun to your head when you wrote that piece,” Kerri said, standing his Jerry’s office doorway.

Jerry laughed.

“Well, I guess I had a change of heart.”

“To put it mildly…”

Jerry laughed again.

“What happened on your trip?” Kerri asked.

Jerry looked back at his email from the transgendered woman.

“I guess I just had a great time,” he said.

Kerri walked over to her husband and kissed him gently on the lips.

“I’m glad,” she said sincerely.

THE END