Jenna – Does the Gang of Four

This is the fifth of the Jenna Booth adventures. The first three are in the Blackmailed: Jenna's series. The other two are in the Jenna -- series. This one can be read independently of the other four.

I hope you enjoy it.

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Part 1: The Libido Cup

Jenna Booth sat in Monique Laroche's office on the sixth floor of the National Securities Services. The view out the window was of the copper roof of the Supreme Court.

"Your next assignment," Monique said, "is to gather enough evidence to put Edwin Thompson and his Gang of Four out of business. They've been involved in numerous securities frauds, but we can't prove any of it in court."

Since joining the Service eight months ago, Jenna had successful uncovered several financial frauds that led to the recovery of millions of dollars, the collection of substantial fines for the government, and the prosecution of eight people.

She handed Jenna a file folder.

"This is everything we have.

Jenna read the file

"They're a suspicious lot," Monique said. "A direct approach may not work."

"Any suggestions?"

"Strike up a friendship with Jason Kim. Go through him to get to Thompson."

"How about a honeytrap?"

"Be careful," Monique said. "Thompson and his gang are vicious, mean, and cruel, especially to women."

A week later, Jenna walked onto the squash court at the Cambridge Club.

"Hi," she said to a handsome man in his mid-thirties. "My name's Anna Swan." Her new alias.

"I'm Jason Kim." They shook hands. "You're new here."

"Joined last week. The pro said we're at the same level." She lied.

They warmed up and then began the game. Jenna was much better than Jason, so she intentionally lost each game by just a point of two.

"As the loser," she said, "let me buy you a drink."

In the lounge she explained that she was the manager of a large investment fund.

Over dinner she said that she was seeking new investment opportunities.

In his condo she let it slip that you need to break the rules to make money.

After missionary sex she admitted that not all her investment funds were legally acquired.

A vigorous doggy-style pounding followed by a short breather led to highly aggressive cowgirl sex.

Exhausted, he pleaded for more rest and then snored the night away.

In the morning, they fucked standing in the shower.

During breakfast, he explained that he participated in the Libido Cup challenge.

"I needed a partner with your energy and stamina," he said. "Interested?"

"What's involved?"

"Fun games. Nothing dangerous. No whips or anything like that."

On Saturday they drove in his Jag to a gated estate in Kleinburg. Dozens of luxury cars lined the circular driveway. They strolled around the mansion to the manicured back lawn.

Thirty or more people holding flutes of champagne and munching hors d'oeuvres milled around the white tableclothed bistro tables. It was a warm cloudless June afternoon.

Jason introduced her to the participants and many of the spectators.

The men were uniformly in their thirties and forties. Like Jenna, the other female competitors were twentyish, pretty, and full breasted.

"This is Edwin Thompson," Jason said. "He's won this competition for the last two years."

He was tall, square jaw, fortyish. Just like his file photo.

He eyed Jenna lustfully. Later, she thought.

"This is Cyndi Ly," Edwin said.

Another beautiful woman. Dark brown hair, light coloured skin, a petite body, and a sexy fold in her eyelid.

A man with a whistle hanging on a lanyard around his neck clinked his champagne glass with a spoon.

"Welcome to the fourth annual Libido Cup Challenge," he said. "I'm pleased that we have a nice crowd to cheer on our competitors. This year we have six teams. Ladies, will you please step forward."

There was a round of applause.

Each woman introduced herself.

"Now strip."

Jason had briefed Jenna on what to expect, that was why she wore only flats and a sundress and left her purse in the Jag.

"Choose your bouncy ball."

To their right were pink, purple, blue, green, gold, and yellow exercise balls with handles and two phallus-shaped attachments. The balls were 58 centimeters in diameter, the dildo 15 centimetres, and the butt plug 7 centimetres. The phallic attachments had been lubed.

Each woman chose a ball and then settled onto it.

Jenna let out a pleasurable "Aaah."

"Ladies," the announcer said. "The race is around the elm tree at the far end of the lawn and then back here. Ready, set."

He blew the whistle. The crowd cheered and the women were off.

Jenna began slowly until she found the perfect pace and the most comfortable position for moving forward while masturbating on the ball.

With each bounce the dildo and butt plug penetrated deeper into her. It was just like a real cock but much more comfortable because of the bouncing effect of the ball underneath her.

Partway down the lawn, Ming lost her balance and toppled onto the grass. Then Nadia had an orgasm so powerful she simply bounced up and down unable to move forward.

As they rounded the tree, Cyndi was in first place with Jenna close behind.

Her 38D boobs flopping up and down, penetration in her pussy and ass, perspiration on her brow Jenna was heading for the finish line as well as an orgasm.

The crowd cheered.

Her eyes widened as she climaxed and yelled "Aaah."

Pushing with her feet she vaulted higher and faster as she nosed ahead of Cyndi to win the race by a breast length.

There were daggers in Cyndi's eyes as both women dismounted their sex toys.

Edwin did not look happy.

There was no time for a rest.

"Our next event is the wheelbarrow race," the announcer said. "Please take your positions."

Jason stood beside Jenna. Edwin beside Cyndi. And a man beside each of the other four contestants.

Jenna was truly into the spirt of the games since she didn't think it odd that the women were naked while the men wore sports shirts and slacks.

Each woman got onto all fours and the men picked up their ankles.

"The race is around the elm tree and back. Ready. Set."

The whistle blew, the crowded cheered, and the teams set off.

Jenna was strong, but masturbation and an orgasm on the bouncy ball had sapped some of her strength.

Halfway down the lawn they were in third place, a body length behind Leanne and Ming.

Jason was pushing her too hard. Her arm buckled and she fell to the ground. She righted herself.

They were in fourth place rounding the tree. Hailey and her partner narrowly ahead of them.

The man holding Leanne's sweaty ankles lost his grip. She landed on the grass knocking Ming who also toppled over.

The crowd shouted and laughed and applauded.

Jenna and Jason crossed the finish line in second place behind Hailey and her man. Cyndi and Edwin were third.

The six women lay panting on the grass.

"We'll take a short break," the announcer said.

The men leisurely joked about the women's lack of arm and shoulder strength as they strolled to the refreshment tables.

Jenna wended her way over to the awning to get out of the sun. Jason handed her a flute of champagne.

"What's next?" she asked.

"Don't know. We were told it'll be something new."

Three minutes later the announcer said, "Ladies, line up here for the chain and apple race."

He handed each woman an aluminum 28-centimeter double-strand nipple chain.

Jenna clipped it on. Each pinch set an erotic shock wave through her. Her nipples were her most sensitive erogenous zone.

"This is a variation of the egg race."

The announcer handed each woman a large Golden Delicious apple.

"With your hand behind your back and only using the nipple chain you have to deposit your apple into the bin by the elm tree. Ready. Set."

He blew his whistle. The audience cheered.

Each woman unsuccessfully tried to position her apple between the stands of her chains. The apples kept falling to the ground.

There was laughter from the crowd.

"It's impossible," Hailey said.

Jenna unclipped the chain from her left nipple, coiled it into a single thick chain and then re-attached it. Another deep intake of breath as the clamp bit into her aroused teat.

She arched her back and placed the apple between her chest and the chain. She put her hands behind her back and took a step forward. The apple fell to the ground.

More laughter.

Jenna picked up the apple and bit into it. Her teeth left a two-centimeter grove.

Once again, she arched her back, placed the apple against her chest, and gently fed the chain through the grove. She advanced. The apple remained in place.

With her hand behind her back she proceeded gradually across the lawn.

Several women cried foul. Jenna ignored them.

The weight of the apple -- at least 220 grams -- was stretching her super sensitive nipples. The pain was excruciating. Tears formed in her eyes.

She was panting and only halfway to the tree when she stopped. The pulling sensation was sending phenomenal waves of pleasure throughout her body. She was on the verge of a nipple orgasm.

Out of the corner of her eye she saw Cyndi and Ming approach. They'd followed Jenna's example of how to carry an apple with a nipple chain.

Jenna quickened her pace. The sudden movement dislodged the apple. It fell to the ground.

"Damn."

She picked it up, repositioned it, and continued down the lawn, dropping her apple in the bin after Cyndi and Ming.

Totally aroused, she unclipped the clamps. Blood rushed into her nipples making them more erect and stimulated. She lightly caressed them and had an orgasm while leaning against the elm tree.