Risking Judy Ch. 03

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Judy submits to the boss.
4.4k words
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Part 3 of the 5 part series

Updated 11/01/2022
Created 06/30/2007
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I woke the next morning to the sensation of someone stroking my already hard cock. I was on my side and Judy was spooning behind me. Her right arm rested on my hip as her right hand slowly wanked me. Her left arm ran under my neck to my chest, pulling us together. I felt her soft breasts pressed up against my back as she kissed the back of my neck.

"Good morning baby," she said softly between kisses.

"Hi," I said as the cobwebs cleared.

"Do you like waking up like this?" she said seductively.

"Oh yeah."

"Good. 'Cus it's about to get better," she said. "It's been thirty days since this nice hard dick has had any fun, and we're going to start catching up...right now."

Suddenly Jason barged into the bedroom.

"Hey guys...oops," he said playfully. "Sorry. Looks like I picked the wrong time to invite you for breakfast."

"Jason!" Judy laughed as she franticly pulled the covers over naked bodies. "Don't you knock?"

"Ja, mon," he said imitating the Jamaican patois. "Get up. Cook has set out a amazing buffet and she gets pissed if it sits around too long."

"Alright," she said. "Get out so we can get dressed."

"I don't mind waiting," he joked.

"Out!" she said throwing a pillow at him.

"Ok," he said heading out the door. "Chill, mon. But hurry up."

"Sorry baby," Judy said when he'd gone. "We'll have to wait until after breakfast."

Judy kissed me passionately on my lips.

"Then I'm gonna' rock your world!" she said.

A thoughtful look passed over her lovely face and her blue eyes lost a bit of their sparkle.

"Richard," she said earnestly. "I love you so much. You know that, don't you?"

"I know hon."

She took me in her arms and held me for a long time.

"I love you too," I said. "More than you'll ever know."

It was sunny and warm so we put on our swimming suits and went out to the patio where the cook had set a dining table next to a long buffet table. Jason was already there.

"The watermelon is wonderful," he said.

"I think I'm just going to have coffee," she said pouring a cup.

I took a plate and headed to the buffet table. When I returned they stopped talking suddenly. 'What were they discussing?' I wondered.

"Babe," Jason said. "Why don't you get some thing to eat? Cook takes it personal when folks ignore her work."

"Ok," Judy sighed and went to get some food.

"Jason, there's going to have to be a change of plan," I said, when she had gone. "Judy is taking this way too hard. We're going to have to shit-can the effort to get you and Judy together."

"No, Dude," he said smiling. "It's just initial shock. She's going to get past this. The mind always tries to find a way around an uncomfortable thought. It's automatic. Something will snap..." He snapped his fingers. "...and then she'll be a happy puppy."

"I'm sorry Jason, but I've made my mind up. This all has to stop right now."

Jason stared at me with a look that got harder as the seconds passed. I thought for a moment he might fly over the table and attack me.

"Who the fuck do you think you are?" he said angrily. "You're nobody. You're a peon.I saywho fucks who. And you don't say anything except 'yes sir' when you're spoken to."

He took a forkful of watermelon and went on.

"You've been way too uppity lately and it's about time for me to put you back down in your place," he growled. "There's gonna be a change around here. From now on you're going to be punished each time you get up on your hind legs."

He stood up and came over to where I sat.

"I'm really sorry. I didn't mean for this to happen..." I started.

"I think you did," he said emphasizing each word by pocking his thick finger into my chest. "I don't think you ever planned to share Judy. I think you were more than happy to waste my time and my money dangling your wife's pussy in front of me, just to jerk it away at the last minute. Well, Dude now you're going to have to be punished."

He sat back down and thought a minute and I began to get nervous.

"You're right, Richard. There is going to be a change in plan," he said. An evil smile crossed his face.

"You're going to learn your place. You're going to learn to be obedient and you're going learn respect for your betters."

I was convinced by then, that I'd made a terrible mistake in coming to Jamaica.

"Here's you first lesson," he went on. "For attempting to come between your better and his future girl friend you will get exactly the opposite of what you just asked for. I am going to fuck Judy all right," he said shoving another piece of watermelon into his mouth.

"But it gets better," he said with growing glee.

"I'm going to fuck your pretty wife, but as long as we're in Jamaica, you're not," he said smiling.

"And so you can see how much fun she has fucking a real man, you're going to watch. And while your watching your better have his way with your wife you will be thinking long and hard about showing respect for your betters."

"You're crazy," I said sounding braver than I felt.

"Really, Dude?" he said. "What do you think your wife's going to do when she finds outyouplanned all this?"

"She won't believe it."

"She will when she finds out you lied about the jock rot to prepare her for me," he said cutting another piece.

"I can get the doctor to say that..." I stopped. The doctor wouldn't lie for me.

"... that you told me about her nipple biting trick," he went on.

"... that you showed me her nude wedding pictures to get me interested. You know. The ones you told her you deleted," he said.

I felt like I'd been punched.

"And what about those pictures we took last night? Isn't she going to wonder why you just stood there holding her dress up while I took nudie pictures of her? Or why you didn't stop me from blasting jizz all over her pussy?"

He chewed slowly and let it all soak in.

He had me. If Judy heard all that she'd divorce me in a flash.

"Jason, I..." I started. He held up his hand to silence me.

"She's coming to my bedroom for a private conversation at 9:30. I want you at my patio door at 9:25," he said rising from the table.

"So, the plan goes forward and you keep your mouth shut. And if you do one thing to spoil this, you can kiss your pretty wife good-bye. Are we clear?"

"Yes," I said feeling sick.

"What?" he said.

"Yes sir," I said meekly.

Jason walked back to the house and I considered swimming out in the ocean to drown myself.

Judy came back with her food and we finished breakfast in silence. I guess we both had too many terrible thoughts in our minds.

We went down to the beach after breakfast. Spreading out our towels on white plastic recliners and lying down to take in some of the early sun. My cell phone rang and I saw it was the headhunter again.

"Look. I'm sorry. I really can't talk about the Hawaii job now," I said.

"Take the job, Richard," he said. "They think you're holding out for more money and they've raised the offer by $15,000. But that's it. I have to give them an answer very soon."

"Not today. I'll call you back soon. I promise," I said, hanging up.

Around 9:15 she sat up and took off her headphones. She pulled her muumuu back on.

"I'm going to check out the aerobics class schedule," she said. "I'll be right back."

When she left, I cut across the grass to get to Jason's patio door as he had ordered.

Jason's patio was surrounded by an arch of beautiful red bougainvillea, so even with his patio doors open, no one could see into the room. He had moved two patio chairs into the open doorway, and draped several towels over them. There was a cushion on the patio just behind the towels.

"Sit out there," he said. "Stay behind the towels and don't make any noise." I sat on the cushion and peered into the room through a gap in the towels.

A knock came from the door and he went to open it.

"Come on in, Babe," he said.

Jason took Judy's hand and guided her into the room. He brought her back to the bed and sat her down. He sat down beside her. They were just a few feet from where I hid.

"I wanted to talk to you because I've decided to tell Richard what you did last night," he said.

"Oh my God!" Judy gasped.

"You insulted me. You must think I'm hideous. I'm sitting right next to you and you choose some black guy you just met."

"I didn't choose anyone," she said.

"I don't cover for people who insult me," he said.

"Jason," she said. "I didn't mean to insult you. I think you are a very attractive man. I always have. And I certainly didn't want...what happened."

Judy started to cry again. I had to fight the urge to barge into the room and strangle Jason. My mind was in high gear - searching for some way out. I had no ideas.

"Richard will never forgive me," she sobbed. "I've betrayed my wonderful husband."

I had to turn away because it hurt too much to watch Judy crying. He let her weep a while.

"Ok Babe," he finally said. "I'm not heartless. You give me what you gave Doctor Feel-good last night. You restore my manhood and prove that I'm attractive. And I'll keep my mouth shut."

Judy's mouth dropped.

"You can't be serious," she gasped. "I couldn't let it happen a second time. Never – never!"

"Fine," he said. "Let's go tell Richard."

"No, please. I can get you money."

"No money," he said. "I want your sex."

"I just can't," she whispered. "I can't."

"If you want me to keep your secret, you can," he said with an encouraging tone.

"It's no good," she said. "Even if Richard didn't know what I did, I would. My marriage is ruined," she sobbed. "It was pure. It was perfect and now I've ruined it."

"Get re-married," he said smiling.

"What?" she said looking up.

"I know the bible too. The Old Testament says that a man can divorce his wife just by saying, 'I divorce thee' three times. Have Richard divorce you."

Judy stood in shocked silence.

"I'll throw you a beach wedding on Friday afternoon, just before you leave," he said. "You can renew your vows. Make a fresh start. Your marriage will be perfect and pure again because it will be brand new!"

"I don't know," she said sadly.

"It's the only way," he said firmly. "You go back down to the beach and think it over. But if you aren't back her by 10:30 ready to show me how much you like me, I'm coming down to talk to your husband." Judy sniffled and rose to her feet. She turned and walked out his room with her head down.

That was Jason's secret plan. His 'third phase.' A temporary divorce!

"You can come out now," he said to me. I stood but didn't come into the room.

"That was cruel," I said.

"The worst is over," he said. "You'll see. Now get out of here and be back at 10:25 sharp.

"Ok," I said dejectedly.

"By the way, you've just gotten a sudden relapse of your jock rot," he said with an evil grin. "If your little pud touches my bitch without my permission I'll cut if off. Got it?"

"Yes sir," I said feeling like a fly falling deeper and deeper into a spider's web.

It was quite a while before Judy got back to the beach. She had her sunglasses on to hide her eyes – still red from crying I guessed. She sat on her chair and pretended to read her book.

'Tell Jason no,' I wished I could say to her. 'I'll forgive you. Our marriage will be fine.' I wanted to say, but I couldn't.

"Richard, we need to talk," she said finally.

"Ok," I said with trepidation.

"I want to get married on Friday," she said firmly.

"What are you talking about?"

"I always wanted a beach wedding. It will be a real wedding, " she said holding my hands.

"We're already married," I said.

"Divorce me," she said.

"What?"

"Divorce me so we can have a real beach wedding!"

"No," I said.

"Yes," she said. "The bible says a man can divorce his wife by saying: 'I divorce thee' three times. And I want you to do it."

"Judy, we don't have to do this," I started.

"Please baby," she said with the most heart breaking tone. "If you love me, if you want our marriage to be pure, you'll do this."

I was trapped.

"Ok," I said at last.

"Good!" she said. "Now say it."

"Are you sure?"

"Yes," she said.

"Ok," I said. "I divorce thee, I divorce thee..." I paused, momentarily unable to cut free the only woman I'd ever loved. My mind reeled – desperately searching for a way out – but there was none. I was lost.

"I...divorce thee."

Judy sat down.

"We're single again...in the eyes of God," she said looking down at her feet.

Be sat together in silence as her words echoed ominously in my mind.

"There's a 10:30 aerobics class," she said after a while.

"You're fine like you are," I said. "Judy, you don't have to go."

"Yes I do," she said.

She pulled her muumuu over her head and bent down to kiss my head.

"Bye Richard," she said.

It really was good-bye. A deep sadness gripped my heart. I'd just divorced the love of my life and she was on her way to meet with a handsome conniving man. A man intent on fucking her.

I ran back to Jason's patio praying for a miracle.

"I told you that first day we met her that I was gonna take her Ferrari ass for a test drive," he said when he saw me. "And it's finally about to happen. I hope you enjoy the show," he said laughing. "I know I will."

"Now sit down," Jason ordered. "And don't make any noise or Judy learns the truth."

I sat down on the cushion and opened the gap in the towels so I could just see into the room.

There was a soft knock on the door. He opened the door and my lovely wife walked in still wearing her muumuu.

"Jason..." she said.

"No more talking," he interrupted. "Are you ready to treat me like you think I'm hot; to treat me like your boyfriend?"

Judy looked at the floor and nodded.

"Good. First of all, take off that thing and put it in the garbage," he ordered.

Judy pulled the muumuu over her head and put it in the can by the door and turned to face him.

She looked magnificent standing there – barefoot – wearing only her tiny turquoise bikini. In the dim light it was easy to imagine what she looked like naked. Jason pulled his suit down and stepped out of it.

"Oh," Judy said quietly when she noticed his huge cock pointing directly at her. It had seemed huge to me the previous night in the dark. But in the light it looked even bigger! It was long and stood out strait from his torso like a spike. The head was bulbous and the shaft widened to a much greater thickness at the base. But what was most amazing was the thickness. It really did look like a donkey dick.

"How about a kiss, girlfriend?" he asked. She took a step towards him, but he stopped her.

"No-no. Lose the suit."

Judy looked down and pulled on the bow on her right hip and the knot came loose. Holding the bottoms with one hand, she pulled on the other bow until it opened too. She slowly drew the tiny bottom between her legs and set in on a chair. My wife stood facing my boss, naked from the waist down!

I felt ill. It was really going to happen. My wife was really going to fuck my boss and there was nothing I could do to stop it.

Judy reached behind her back and pulled on the string tie. Her heavy breasts came free from the bikini top as the knot yielded. She held the bikini against her breasts and looked up at Jason and then down at the huge shaft pointing directly at her pussy. She seemed too shy to reveal her last secrets to his hungry eyes.

At last she lifted one hand to her neck, she pulled the tiny top over her head and placed it beside her bottoms on the chair.

Judy straightened her hair and turned back revealing to him her magnificent body in all its naked splendor.

She stood with her hands at her hands at her sides, glancing at his monstrous member. I could clearly see her upturned pink nipples, but they were not hard, so I knew that she was not sexually excited.

I knew she had to service Jason, but I prayed she'd be as mechanical as possible. I didn't think I could stand it if she started to enjoy fucking him.

"You are so hot!" Jason said.

Judy smiled a little.

"Why don't you turn around?"

Her narrow hips rocked as she turned.

"Beautiful! Now come here and kiss your boyfriend."

She padded over to where he waited, her full breasts swaying slightly. Jason pulled his cock out of the way, grabbed my wife's small ass and pulled their hips together. He leaned down and kissed her briefly but Judy's hands stayed at her sides.

"Is that how you kiss your boyfriend?" He asked.

My wife wrapped her slender arms around his neck and leaned close to his body. Her perfect breasts pressed into his muscular chest as their lips came together again.

This time the kiss lasted for quite a while, their tongues exploring each other's mouth for the first time. In spite of the painful jealous feeling felt, I had to admit that it was a lovely sight. Judy on her toes, her lean smooth body tight against his tall muscled frame.

I hated the thought, but they were made for each other in a way she and I never were. Judy was finally with the god-like male who matched her perfection.

"Stroke me," he said. "I love to kiss a woman while she strokes my cock."

Judy leaned back, took his trunk-like cock into her small hand and began to wank him.

They kissed again – this time longer and with growing passion.

Finally he broke the kiss. They stood looking into each other's eyes for a moment, Judy still slowly stroking his thick cock. Jason leaned back and took a breast in each hand. He touched them gently, brushing the nipples and then softly squeezing them and testing their heft.

Jason sat down on the bed. Grabbing her hips with his large hands he pulled her to him and took one of her pink nipples into his mouth. I saw his mouth working and I knew he was using the technique I'd told him about on the plane. Biting her nipples to get her ready to fuck him. My wife made a little sound, and I knew the nerve connection from her nipples to her pussy was working.

When he switched to the other nipple Judy's hands came up and tangled in the thick hair on the back of his head, holding him to her breast. He nipples were hard and I knew my wife was becoming aroused.

Jason let go of Judy's tits and moved back on the bed. He laid down - his monstrous shaft pointing obscenely up into the air.

"Ok, Girlfriend," he said. "Sorry for the rush, but you've been keeping me waiting for far too long. Mount up."

Judy climbed onto the bed, straddled his thighs and shuffled up to his big cock. It reached all the way to her belly button! Jason put his hands behind his head and watched her work.

My wife had to get up on her feet and squat over his shaft, due to its length, something she'd never had to do with me. She held his shaft with her right hand and reached between her legs with her left hand to open herself.

'No!' I whispered soundlessly.

It was painful to watch, but I couldn't look away. Judy pressed her pussy down against my boss's cock - the thin moist lips wrapped around the bulbous head. She placed her small hands on his muscular chest for balance.

Nothing happened for a while, but I could see strain on Judy's face as she pressed herself down on his stiff cock.

"Ouch," she said, as the cock-head finally slipped into her body.

For a while it looked like that was all my wife could stuff into her pussy. She closed her eyes and furled her brows as she strained to get more of his cock into her moist hole.

Her heavy breasts rose and fell as her breathing became more labored.

I looked down between their bodies again I was surprised to see that half of his cock had disappeared! Her steady pressure was succeeding in getting her pussy absorb his huge cock.

Their bodies drew closer, and only a few inches of Jason's thick shaft separated their bodies. Judy's face relaxed a little and I saw droplets of sweat forming between her breasts.

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