Blackmailed - Jenna's Holiday Pt. 01

This is the first of Jenna's adventures in the Blackmailed series. I hope you enjoy it.

Part 1 -- Jenna needs a vacation

Jenna Booth and her husband Sam had been working very hard. Jenna was exhausted running a charitable foundation started by her grandfather. Sam, a high school mathematics teacher, longed for a break from his recalcitrant students.

"We deserve a holiday," Jenna said as they sat down to their dinner. "How about we go on a last-minute cruise?'

"We can't afford it," Sam said.

"Sometimes you can get great deals on those sell-offs websites."

"It's too late," he said. "March break is next week. Nothing will be available."

After dinner they searched websites. Cruises were too expensive. Resorts weren't available on such short notice. Vacation homes required too much maintenance. After a frustrating hour of trying, they went to bed too tired and exasperated to have sex.

Sam tossed and turned. At three in the morning, he slid out of bed, careful not to wake Jenna. He didn't bother to get dressed and instead tiptoed naked into the living room, sat down at his desk, and booted his computer.

There had to be someplace sunny and warm with no squealing kids.

He typed in Caribbean adults 21+.

The list was pages long. He reviewed some websites. No availability. Too pricey. Not on the beach. Too crummy looking.

The computer's clock glowed 3:49 AM.

This was tired and sleepy. He wanted someplace relaxing.

He misspelt sedate. The computer said: Caribbean adults 21+ seductive.

Two sites appeared on his screen.

The first looked promising, but it was a bust. Availability in two weeks, but nothing for next week.

He clicked on the other website.

The first page of the resort looked great. Photos of well-appointed villas with an ocean views, king sized beds, luxurious bathrooms with Jacuzzis. Long private sandy beach. Chaise lounges. Palm trees. Main restaurant with dance floor. Luncheon restaurant by the beach. Two swimming pools. The women in the photos at the swim up bar didn't have any bra straps.

It's topless, he thought. Great.

His wife was a twenty-eight-year-old knockout. Shoulder length red hair, beautiful face, gorgeous athletic body, 38 D breasts, tight ass, narrow landing strip of short red pubic hair. It would be a pleasure to see her topless in a tiny bikini.

He typed in availability.

Success! Only one villa left for next week.

He went to the reservation page. The price was more than they had budgeted. But it was all-inclusive. Good, because they couldn't afford to pay for any extras at the resort. He typed in the relevant credit card information and hit entered.

Just as he was about to turn off the computer, he heard a ding. He opened his email. There was a confirmation, with a note. We look forward to your arrival at the Seduction Resort.

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They sat at the island in their kitchen having a late Saturday breakfast. Outside it was cold and drizzly.

"I couldn't sleep last night," Sam said, "so I got up and searched the web. I found a perfect resort, and I booked us in. I emailed you the link. It's a bit pricey, but we deserve it."

Jenna jumped up from her chair and gave him a big hug and a kiss.

"Just think," he said, "a week today, we'll being fly out of here at seven in the morning, and in the afternoon, we'll be drinking margaritas on the beach in Jamaica."

"I'm so exited," she said. "Maybe I should get a sexy new outfit for the resort. Thank you so much darling."

She gave him another kiss and rushed over to her computer to find the link to the resort's website.

"I've got to help my Dad repair the fence in his backyard," he said. "I won't be back until dinner time."

He left their apartment and Jenna clicked on the main page of the resort's website and then scrolled through the other pages that revealed the true nature of the Seduction Resort.

She logged off her computer and said to herself, "It's not a sundress I'll be needing."

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While working in the cold on his father's backyard fence, Sam imagined Jenna jogging on the beach at the resort, her large boobs bouncing in a red high-cut Baywatch one piece. Or topless in a sexy bikini showing off her large breasts with her oversized dark brown areolas, each about two-and-half inches in diameter.

At six, he entered the apartment and called out. "Hi Jenna. I'm home. Did you buy something sexy for the resort?"

She strolled naked into the living room wearing only a pair of sandals. Her pussy was totally clean shaven. From her eyebrows down, there wasn't a speck of hair on her body.

"This is all I'm wearing at Seduction during the daytime," she said.

"What?"

"Didn't you realize it was a nudist resort?"

"No," he said. "I thought the women in the photos were topless."

"And bottomless. Men too." She shot a look at his crotch. "You'll be a hit with the women when they get a look at your equipment."

"Nude all the time?"

"During the day, you're naked. Then you dress for the nightly themed dinner. PJ evening. Temptation Thursday. And I bought something special for Friday night. Stay right there."

He sat down on the sofa as she re-entered the bedroom.

Jenna had a body to die for. She'd be a hit walking around naked at the resort. But that didn't mean he was prepared to be nude. He wasn't ashamed of his body. He'd maintained his college football physique. But totally naked? All day? That would take some getting used to. And what if he got a hard on while seeing the other women walking around the resort in the buff?

Two minutes later Jenna re-emerged wearing black high heels and a sheer black mesh nightdress that fell to her ankles.

Around her neck was a red faux leather choker collar. It was same colour as her shoulder length hair. Attached to the front of the collar were three silver chains, designed to look like interlocking curved links. Each was about a quarter inch in diameter.

The middle chain was taut, stretching down her chest and flat stomach and ending with a shinny butterfly clamp on her clit. The other two chains were fourteen inches long. They hung loose, falling between and below her large round breasts. A butterfly clamp secured the end of each chain to a nipple. The three clamps connected to the most sensitive parts of her body.

"This is for the BDSM party," she said.

"You look so hot," he said standing up.

"That's not all," she said. "It's a resort for swingers."

He'd fantasized about having a foursome. But it was a passing daydream that he never mentioned to Jenna.

"I had no idea." He took a deep breath. "We don't have to go if you don't want to."

"Oh, we're going," she said. "We both need a holiday, and we can't get our money back if we cancel."

"Okay. But that doesn't mean we have to swing. We can have our own fun, just the two of us."

He put his hands on her shoulders and slowly slid the spaghetti straps off her shoulders. The sheer nightshirt fell to the floor. She was totally naked except for the body jewelry.

"What happens if I pull on the chains?"

"Then the clamps get tighter, and my tits and clit get even more stimulated."

With his right hand he gently pulled on the long chain that was connected from the collar to the clit clamp.

"Ooooh," she purred.

"If I let go of the chain will the clamp loosen."

"No."

He pulled again.

"Awwww," she exhaled.

"When did you get into BDSM?" he asked.

"You know me. Always willing to try something new."

He pulled a third time.

"Owwww," she cried. She was breathing loudly.

He kissed her open mouth and moved his right hand to caress her left breast. Her nipple was erect and poking through the clamp. His left index finger massaged the smooth clamp on her clit. Then he slid his index finger into her warm and wet pussy.

He broke off the kiss and said, "Let's go to the bedroom and fuck our brains out."

"Good idea," she purred.

She lay on her back, across their king-sized bed, with her neck at the edge of the mattress. She was looking at him upside-down while he stripped.

"If I tilt my head back," she said, "it tightens the clamp on my clit."

She did so and let out a soft murmur of delight.

He stood by the side of the bed. His penis was hard and standing at attention.

Her head was beneath his crotch, so she stuck out her tongue to lick his balls.

"I wonder if I can make them as hard as billiard balls," she said.

Without using her hands, she took his left ball into her mouth and sucked on it gently. Then she did the same to his right ball. They were becoming firm. He moaned with pleasure as she tea-bagged him.

His sack was too big to get both his balls in her mouth, so she alternated sucking one and then the other.

"Oh baby," he groaned.

He looked down at his gorgeous naked wife, lying on her back, arms at her sides, sucking on his balls.

Then she began to lick the underside of his dick. He loved that sensation. Pre-cum appeared at the tip of his cock.

She slowly moved her tongue along his shaft to its bulbous head. She licked up the pre-cum and then kissed the top of his throbbing penis.

She readjusted herself. Her head was entirely off the bed. Now she could deepthroat him in an upside-down position. The chain along her stomach was stretched rigid, the clamp pulling at her clit.

Her clitoris looked red and sore. He wanted to suck on it.

Maybe later. Right now, he knew what to do.

He eased his penis into her mouth. In two inches, then four, then six. Eventually, all eight inches of him was in Jenna's mouth. He could see the bulge of his cock in her throat. It almost reached the red chocker around her throat.

He reached down and ran his fingers along the pulsating bulge as though he was massaging himself. She'd never given him a blowjob in this position before. This was so hot. He could fell and see his cock throbbing in her throat.

He leaned forward, put a hand on each of the chains connected to her breasts, and pulled on them. The nipple clamps tightened.

She moaned. In pleasure or pain? He wasn't sure.

He pulled again.

She made a gurgling sound. She couldn't yell with his cock halfway down her throat.

He let go of the chains and slid his cock out of her mouth.

She took a deep gulp of air and then shouted, "Don't fuckin' stop now. I want more."

He straightened up so that he could pump her as hard as he could. He forced his dick into her, deeper than he'd ever been before, trying to get all the way down her throat and into her stomach.

He thrusted and thrusted, jerking his pelvis forward, watched the budge of his cock slid along her throat. The chain along her stomach stretched tauter and tauter with each of his thrusts. The butterfly clamp on her clit tightened and tightened. Tears formed in her eyes.

He thrust one last time and shot his load deep into her. He continued to thrust repeatedly, ejaculating again and again. He unloaded more jism into her than he ever had. It was though he had an inexhaustible supply of spunk.

When he was done, he pulled out.

Jenna immediately rolled onto her side and began to cough. Sperm fell from her mouth and dribbled onto the floor.

"Wow," she said. "I tried to swallow it all, but there was too much."

She was panting.

He climbed across the bed, forced her hips onto the bed, and positioned his head between her legs. She spread her legs wide to accommodate him as he undid the clamp on her clit that was red and throbbing. He began to lick and kiss it better.

"Ooooh," she moaned. She loved cunnilingus almost as much as she loved hard core fucking.

He kissed and licked. Then he separated her pussy lips so that he could explore her vagina with his tongue.

She moaned non-stop. He continued to suck with his lips and lick with his tongue.

Her moans became louder and louder. He kept licking and sucking. She bucked her hips. He teased her clit with his tongue.

Her voice deepened as she cried out, "OH MY GOD. I'M CUMMING. OH FUCK. OH YES."

Her face was flushed. She tossed her head back and forth. She was shaking violently.

Her orgasm lasted for over a minute and a half.

After she came down from her high, she repositioned herself with her head on the pillow. Sam inched up her body, putting his tongue into her navel, kissing her stomach, and ending at her nipples. They were hard and erected and sticking up through the butterfly clamps. They were a bright red, her large areolas a dark brown.

He nibbled the top her left nipple.

"AHHHHHH," she howled.

He licked the top of her right nipple. She screamed again.

"They're so sensitive," he said.

He undid the clamps. Her breathing slowed down as blood returned to her nipples.

He kissed, licked, and sucked on her right breast, and then on her left.

"Better?" he asked.

She undid the red chocker collar and tossed it and chains onto the bedroom floor. Then she raised her head off the pillow, and they kissed deeply. Their tongues danced with one another.

"Lie down beside me," she said, "and let me suck on your nipples."

He did so.

She rolled on top of him and kissed his right nipple while her right hand massaged his left nipple. Then she sucked his left nipple while massaging his right nipple.

They kissed and massaged and fondled one another for another ten minutes, rolling all over the bed. Sometimes with Sam on top. Sometimes with Jenna on top of him. Then she began to stroke his penis.

"Are you ready for round two?" she asked.

She pumped his cock with her right hand until it once again became firm.

Then she climbed on top of him, spread her pussy cheeks, and lowered herself onto him.

"Now let's fuck our brains out," she said.