Blackmailed: Jenna’s Funfair Pt. 05

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How many more men can she do while suspended in the air?
2.1k words
4.57
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Part 3 of the 7 part series

Updated 06/14/2023
Created 10/18/2021
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Part 5 -- Jenna takes on two more

Once again, she was hanging on her virtual St. Andrew's Cross lost in her thoughts. It's so easy to daydream and contemplate when blindfolded with no visual distractions.

She thought about the last guy. What a loser. The butt plug in her ass was giving her more stimulation than that guy. The dildo in her cunt, on the other hand, was having its effect. She could fell another orgasm growing inside her. But not enough to push her over the edge. She so wanted to cum again.

She couldn't remember how many orgasms she already had. Nor how long she been the funfair prize. How much more sex could she take? How much longer could she last?

She listened to the wheel spin and the sounds of the hopeful men all wanting to win her. To have her. To fuck her. To sodomize her. To deepthroat her. And she was willing to let them debauch her, in order to raise money for the Conrad Foundation and avoid going to jail.

Was that her only reason?

No, it wasn't. She was secretly shocked and horrified to realize that she was enjoying this so much. Nude, exposed and helpless, having sex in public with total strangers. What a mind-blowing tune-on. She was euphoric.

She didn't realize that she was now at a thirty-degree angle from the floor with her head at the height of a man's waist. It was as though she was the carved figurehead at the prow of an old wooden schooner. She was unaware of her new position because there was no pressure on her arms, legs, and body. Willard's bands made her feel as though she was floating on a cloud.

She no longer heard Martin and the audience. She focused on the dildos and what they were doing to her. The orgasm was beginning to well insider her. It would be a big one. Her breathing quickened. She saw stars as she climaxed. She opened her mouth to let out a scream and suddenly there was cock part way down her throat. Her nose was in his curly pubic hair.

She hadn't expecting that. She didn't know that the latest winner was standing in front of her. His erect member an inch from her mouth.

She controlled the automatic gag reflex with a few quick swallows. She marvelled at the feeling of his penis in her mouth and throat, combined with the bliss of her orgasm. It was rapture. Cascading curtains of coloured lights that collapsed and folded and then vanished before her eyes beneath a blindfold within a cowl.

The continuous vibrations of the two dildos and the cock in her mouth were too much for her. She climaxed again. It was heavenly joy. An orgasm she couldn't scream out loud because there was a cock deep in her mouth and throat.

The orgasm subsided. She forced herself to slow down her heart rate. She could only breathe through her nose that was pressed against his pelvis.

After two sensational orgasms, she was determined to give this guy the best blowjob ever. She'd do it without the use her hands. Only her lips, mouth, and tongue.

She tilted her head back. She wished that she could look into his eyes, to increase his pleasure.

He somehow got the message and pulled his penis out of her mouth.

She focused on the tip of his circumcised cock. She licked it using the least amount of pressure, like teasing it with a feather. As he moved forward, she slid the tip of her tongue down his shaft until she reached his balls.

His dick was much longer than her husband's. Maybe two inches longer. And a bit thicker. Other than the grandfather and the one limp guy who fucked her ass, did only well-hung studs show up at this fundraising event?

The dildos continued their never-ending pulsation within her. She re-focused her attention on his balls.

She began with soft, wet kisses. Then she massaged his sack with her tongue. His pubic hairs were thin and soft. His scrotum was firm.

She gently took one ball into her mouth and softly licked and sucked it. Then, she did the same to the other testicle. Finally, she took both of them in her mouth sucking them softly. He moaned with pleasure.

As he moved back, she returned to licking his shaft as though it was an ice-cream cone, slowing getting to the top. She pursed her lips together and gave the tip of his cock small kisses. She opened her mouth slightly. She licked the top of his penis, followed by rapid tongue movements around the bulbous head of his cock. She gently squeezed it with her lips. Then she began to lightly suck the top of cock.

He moaned louder.

The dildos vibrated within her. Was she going to cum too?

She opened her mouth wider and wrapped her lips around the shaft of his penis. It was a though they were in a Vulcan mind-meld, each knowing what the other wanted.

He moved forward. She took the first few inches of him into her mouth sucking gently. She took a few more inches into her mouth, letting his cock rub against the inside of her cheek. Then a few more inches, slowly.

She opened wider and the tip of his cock touched the back of her throat. She took in more. It touched her tonsils and she gaged slightly. He wasn't fully in, so she opened her throat wider, and he slid further into her.

Once he was all the way in, she began to bob her head up and down, taking his cock in and out of her mouth. She alternated the speed and the amount of pressure she applied to his dick with her lips. Sometimes she bobbed slowly. Then quickly. Sometimes, she let it slide easily in and out of her mouth. Other times she applied pressure with her lips all along its shaft. Variety was the essence to a good blowjob.

She felt his pre-cum and wondered how many loads she could suck out of him. His first load went straight down her throat. Quickly followed by his second load of sperm.

She stopped bobbing. Instead, she squeezed her lips on his shaft. Another load shot down her throat. He was panting. Was there more?

She squeezed harder. Nothing. If only she could use her hands.

She continued to squeeze with her lips.

A fourth, smaller rope of sperm fell onto her tongue. She savoured its salty taste before she swallowed it with satisfaction.

"You're fantastic," he said. "I've never had a blowjob like that before. Wow."

-----

Jenna heard him walk across the stage. Solid footsteps. Was he a large man?

Willard adjusted her so that she floated on her back parallel to the stage floor. A dreamlike position. It reminded her of the evening her husband tied her spread-eagled on their bed. Would this man ravage her the same way her husband had?

She could sense him standing between her outstretched legs.

Suddenly, there were cries of astonishment from the audience. What had happened?

Then she received the surprise of her life. A penis lay quivering on her stomach. Except that it stretched all the way to her navel. Flesh on flesh, it twitched like a python on her abdomen as though trying to bury itself into her very short red pubic hair.

"The first man that fucked you," he said "had a dick that was almost a foot long. The guy you screwed in the chair. His was almost two inches thick. Mine's longer and thicker than both those guys. I'm telling you this because I don't want to hurt you."

She knew he was telling the truth. She felt it throb as blood pulsated through his cock. Was it getting larger? Longer? Thicker? Could she possibly take something that huge in her cunt?

"No woman's ever been able to take all of me," he said.

Was this a dare? Jenna loved challenges. She hoped that the first two guys and the dildos had prepared her for this guy. Would she be able to handle all of him? Wouldn't it be nice if she was the first woman he properly fucked?

"So, I'm going do what I normally do," he said. "I'm going jam as much of my meat in you, as you can take. Then I'm going to pull it out and shoot my load all over your tits."

Maybe, she thought. Unless she was able to pull him all the way into her cunt and not let him exit until he unloaded everything he had into her. His dick was huge, he must have an enormous load of spunk.

"I'm here for you, Big Boy," she said. "Let's get started." She was curious to know how much of him she could handle.

Willard had anticipated her, so he released the tension on the waist band. She could now move her hips and pelvis.

The dildo was removed, and he began his lengthy journey into her pussy.

Within the blindfold, her eyes widened. Was this a dick or a bowling pin? He was massive. Gigantic.

He eased more of his shaft into her. It was smoother than she expected. Had he applied a silicon lubricant?

She tilted her pelvis up and he slid in another two inches. Her breathing increased. She was incredibly aroused.

She tilted up again and another few inches entered her. She saw fireworks.

More of him slowly penetrated her. She moved her hips to make it easier for both of them. She was being stirred in areas no penis had ever touched. She was seeing the colours of the rainbow.

More of him entered. She was on fire. Every nerve in her body was alive. He was much thicker and longer than any man she'd ever had. Much thicker and longer than anything she ever dreamed of.

Another few inches. She wished she could put her heels on his ass cheeks and pull him further into her.

Suddenly, he stopped.

"Don't stop. I want it all."

"I'm all the way in, lady." There was the sound of astonishment in his voice.

"Okay. Now fuck my brains out," Jenna ordered.

He began to pump. She felt a hot wave move through her body, from her vagina to her fingertips and her toes. His dick was so long, he had to take a small step back and then move forward so that he could shove his cock in and out of her. He started to take quicker steps. He was fucking as hard as he could.

She quickly climaxed and scream repeatedly as he pumped faster and faster. She was in paradise, moaning aloud at the joy of being magnificently fucked. It was as though light were pouring through her body.

He continued to screw her with the energy of a teenager who was losing his cherry for the first time. She was getting a light-headed rush. It was continuous pumping. Sheer joy.

"More," she yelled. She didn't want the euphoria to end.

With his fingers, her pulled apart her pussy lips and drove his throbbing cock all the way into her in one quick shove, his balls smacking her ass.

"AAAH."

She was spinning out of control, as though caught in an orgasmic whirlpool. Round and round she seemed to whirl.

"OH MY GOD."

He continued to pound away at her. Electricity surged through her body. He continued to fuck her with unabated energy ramming his meat in and out of her.

"HOLY FUCK."

The Northern Lights exploded before her eyes, concealed by a blindfold within a cowl. She thought she'd die from intense pleasure.

"DON'T EVER STOP."

How long had they been at it? It seemed like hours. She was fatigued, her body covered in perspiration. She'd lost count of how many orgasms she'd had with this man.

"I'm coming," he shouted.

For the next two minutes, she helped him experience what sex was supposed be like, shooting sperm into a woman who was delighted to accept it. She felt every gorgeous surge of his jism, and he gave her a vast load.

She revelled in the enjoyment of such a mammoth cock residing in her cunt. Filling her up.

Eventually, he pulled his tree-trunk sized dick out of her. He was panting almost as hard as she was.

If Willard turned off all the dials and she fell to the stage, she wasn't sure that she'd be able to stand up. She'd never been fucked that that before.

"Thanks so much. That's the first time I've had real sex."

"My pleasure," she said exhaustedly. She was dripping in sweat.

It certainly had been Jenna's pleasure.

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