Risking Judy Ch. 05

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Judy and the boss go to a private island.
3.8k words
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Part 5 of the 5 part series

Updated 11/01/2022
Created 06/30/2007
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We fell into a routine. Every morning at 10:25 my wife left me on the beach to take her aerobics class taught by Jason. And every morning at 10:30 I was treated to, what I began to think of as, a live sex show with beautiful actors.

We all were getting something that we liked. Judy was getting her daily orgasm - actually Jason gave her two. Without Judy's knowledge, Jason permitted me to watch the sex show as long as I shot my cum neatly into a small garbage can he set out on his patio. And Jason cured his blue balls by cumming frequently into my wife.

One morning at breakfast Jason asked Judy if she'd like a change. By then he was pretty much ignoring me.

"Dr. Feel-good has invited us to visit him at his farm where he grows his Skunk weed," he said.

"I've had enough sun," Judy said. "A car trip sounds like fun. Can Richard come too?"

"I suppose so," he said with irritation in his voice.

We went out to Jason's rusty blue Nissan. Judy got in front with Jason and I jumped in the back.

We drove deep into the lush verdant country just outside of Negril. We passed abandoned sugar cane fields and tiny colorful cement block churches. Jason stopped to pick up two hitchhiking Jamaican schoolgirls in matching uniforms. They climbed in back with me. They were cute and giggled a lot but wouldn't respond to my questions. Shy I guess. We dropped them off at a dirt road that led to their school.

After about an hour Jason parked the car next to a road-stand where a round Jamaican woman in a colorful dress was selling drinks. We walked behind the road-stand and found Dr. Feel-good sitting on a bench next to a large shed made of unfinished wood.

"Welcome Mon," he said warmly to us all but was seemed especially happy to see Judy.

He gave her a hug that lasted until she pushed him away. We all laughed but I was beginning to tire of his constant hitting on my wife.

"Let me give you a tour of my little farm," he said. "The little paper cups on the table hold the seedlings, and under the table is where I keep my bags of soil and fertilizer. My ganja field is down this dirt path, behind a grove of trees."

"I'm not going down there," Judy said. "These are new sandals."

"I'll stay here with Judy," Jason offered. "You guys go on ahead."

"Ok," I said. I knew better than to argue with Jason.

The doctor and I walked to the ganja field alone. As we went through the trees he lit a huge spliff and passed it to me. I hadn't been high since we'd gotten to Jamaica so I took it, and we smoked as we walked.

The field was disappointing. The whole thing covered an area no larger than most back yards, and all the plants were thin and short. I had expected a forest of ganja plants standing taller than a man could reach.

I felt myself getting higher as we walked around.

We went back to the shed using another path and we arrived at the back door. He opened the door and the strong aroma of potent marijuana assaulted me. All around the room, thousands of plants were hung upside down to dry. Through a gap in the plants I had a view into a dimly lit room. In the room a plastic bag served as window covering, and cans of food filled shelves along the unfinished walls. I assumed that I'd found Dr. Feel-good's home.

I looked into a corner and stumbled backward in surprise. On a small bed two people were wildly fucking.

I leaned forward for a better look and realized that it was Jason and Judy. Jason was on top and he was still dressed except that his shorts hung around his ankles. His naked ass rose and fell with amazing speed as he fucked down into my wife. Judy's naked legs, with her new sandals still on her feet, were wrapped tightly around him. Her shorts and panties sat in a small pile on the dirty floor. Apparently they had been in too great a hurry to fully undress.

"Your woman's a pretty lady," I heard from behind me. I turned around and saw the doctor smiled mischievously at me, but it only made me angry.

"She love the big bamboo," he said moving his hips in a fucking motion.

"You should get out of here," I said with growing annoyance.

I turned back and watched them fucking again. I grew even more depressed and dejected than before. Before I had been important to them in some way. But now it was just about them. They were simply two lovers addicted each other. Two lovers who couldn't wait to undress and mate. And all they needed from me was to leave them alone.

"I think she'd like to ride the bigblackbamboo," Doctor Feel-good said.

"Come on," I said pulling him out of the shed. I'd finally had enough of him.

"Turn me loose," he said angrily.

"Stay away from my wife," I said. I could tell he was pissed, but I didn't care.

"Respect, Mon," he said smiling malevolently.

"I'm serious," I said. "Let's go. We'll circle back and give them time to finish."

The doctor lit another spliff and we smoked it as we walked. By the time we arrived at the front of the shed I was much too high. Judy and Jason were sitting on the bench looking happy and relaxed and glowing.

"Richard," Jason said laughing. "You don't look so good. We'd better get you back."

"Oops," Judy said when she stood. "I'd better use the ladies' room before we go."

"Here pretty lady," the doctor said as he put his arm around my wife's waist. "Let me show you."

"I can find it just fine myself," she said pushing him away. She went back into the little shack.

"Come here Doctor," Jason said. "I've got something for you." Jason pulled a small crumpled white piece of cloth from his pocket and handed it to the doctor.

"Ya Mon," the doctor gleefully said as he unfolded it.

It was Judy's panties!

He put them to his face and inhaled deeply.

"Oh. So sweet."

I could have strangled him then and there. And I was pissed at Jason too.

"Jason," I said. "Keep him away from Judy!"

"You still haven't learned, have you?" he said menacingly. "You're going to pay for that later."

'Oh no,' I thought as I calmed down. I watched the Doctor sniff and fondle my wife's panties and grew angry again.

"Give me those!" I said reaching for them.

"No way, Mon," he said jerking them away. "I might need them later," the doctor said laughing. He mimed masturbating into Judy's panties.

Mad rage filled me and I lunged at him.

The ganja however had been too strong. I stumbled and fell at his feet.

"Let's go killer," Jason said picking me up. Judy came out of the shack and the three of them carried me back to the car.

They laid me down in the back seat and Judy got in front with Jason again. I was getting higher and higher and I felt like I needed to sleep. I dozed off. When I opened my eyes Judy was gone! Jason was looking down at his lap.

"That's nice," he whispered.

I knew instantly that my wife was showing him 'Judy's Car Trick.'

Jason had taken everything from me. He had mastered me in every way. I looked up at the roof of the Nissan and listened to the sounds of Judy fellating my boss.

"Here it is," he said softly, and I knew Judy was draining him of his second load of the day.

"Thank you," he said after a long while.

"My pleasure," she whispered as she sat back up. "No! Leave it out. I like how it looks."

"Ok girlfriend," he said laughing.

I passed out again.

Thursday finally came. One more day until I got my lovely wife back. I was not, however completely sure she would want to come back.

At breakfast Jason pulled me aside.

"I am going to invite you two to take a boat to a deserted island where there is a nice beach," he said as Judy cruised the buffet. "Unlike the ganja farm trip,youare going to decline the invitation. Clear?"

"Yes Jason," I said obediently.

"However you will encourage Judy to go," he ordered.

"Yes sir," I said. He wanted me to make it convenient for him to fuck my wife and I was going to do it.

As it turned out, she jumped at the chance to go to the island without me. I helped her pack a bag for their trip as Jason packed a cooler with food and Red Stripes. She was incredibly excited bout the trip.

I kissed her good bye as they left the house. My phone rang and the headhunter started pestering me to make a decision about the job offer in Hawaii.

"The raised their offer again," he said. "But this is it."

"I don't know," I pleaded. "I just can't think now."

"You've got to move on this now," he said. "They're talking to someone else, but they really want you. They'll wait a few days, but if they don't hear from you by Monday they're going to offer the position to this guy from New York."

"Ok. I get it," I said. "Bye."

I went down to the sea and walked along the beach. It was a perfect day for sunning and lots of hot girls had their tops off. I gazed at boobs in various shapes and even some with nipple rings but none as nice as Judy's boobs. I was lonely for my ex wife and the day passed slowly.

They got back to the house around sunset. Judy was sunburnt and very drunk. I took her to our bedroom and helped her get undressed. As I applied sunburn lotion I noticed that her normally white ass was burned bright red. I turned on the ceiling fan to cool her and left her to sleep off the beer.

Jason was sitting in the living room, drinking a Red Stripe. He looked sunburnt and drunk too.

"What a great day! Sorry you couldn't be there," he said with a chuckle.

"Was Judy tanning with her bikini off?"

"Sure was," he said smiling. "I just told her to get naked and off it came. Hell, she spent the whole the day with it off." He had certainly changed my formerly modest wife.

"Well at least there was no one there to see her."

"Yes there was," he said.

"You weren't alone on the island?"

"Nope," he said. "Doctor Feel-good was there."

I couldn't believe my ears! I started getting angry. That sneaky son of a bitch was there!

"Why was he there...sir?"

"I invited him," he said laughing.

"Did he see my wife naked sir?"

"Of course," he said taking obvious joy in my humiliation. "I told you that you'd pay for shooting off your mouth other day."

I collapsed into a chair. I thought of the three of them eating, drinking, swimming together all day, and my wife naked the whole time. And the lecherous Doctor Feel-good finally able to see the perfect body he'd lusted for all week. I was crushed.

'Why didn't I keep quiet the other day?' I thought. 'None of this would have happened if I'd just been respectful to Jason, like I should have!' I hated myself then.

"Besides I didn't like the way you treated him. The Doctor's my friend. That makes him your better too," he went on. "You don't mind that I let him see your wife naked, do you?"

"Whatever you do is fine, sir."
"Good. 'Cus that's not all," he said and waited for my reaction.

"What else, sir?" I said almost too afraid to ask.

"He fucked her, too."

I was in shock!

"Oh my God," I said covering my face. The room started to spin.

"No. It's not possible!"

"It happened, dude," he said smiling broadly.

"Judy doesn't even like him...sir," I said trying to gain control of myself.

"I told her to fuck him," he said. "At first she said no. She said she only wanted to have sex with me."

He took another sip of his Red Stripe. He watched his words sink in and then went on.

"I told her it would really make me really happy if she fucked him. She thought it over and said since she'd already had sex with him that first night on the beach, doing it one more time wouldn't hurt."

Jason laughed out loud and slapped his thigh.

"She said 'I'm not married so anything goes'," he said.

"They did it on the beach, sir?" I said feeling defeated.

"You bet! And what a sight. He took her doggy style to keep sand out of her pussy. He's a very considerate guy."

He sipped his beer and went on.

"I know your wife didn't like the Doctor, but once he fucked her she really got into him," he said as if I'd be glad to hear.

"And he really got into her," he said laughing at his own joke. "His big black hands squeezing those pure white boobs until she screamed. That long jet-black cock slicing into your wife's little pink pussy. Her yelling, 'Oh Doctor! I'm cumming! You're making me cum so hard.' Him yelling, 'Take this white bitch.' It was really something to see."

"You just stood there and watched, sir?" I said.

"No," he said clearly enjoying my total defeat.

"I took pictures," he added. He took a drink and went on.

"Then we all went skinny dipping in the ocean. I was hard from watching them fuck so I asked Judy to give me an underwater blow job. It felt great standing in that cool water with her warm mouth attached to my cock. But she couldn't hold her breath long enough for me to cum, so I just fucked her. Did you ever fuck your wife in the ocean before?"

"No sir," I said softly.

"You should. Judy likes it," he said. "It was a great day. The three of us swam naked, took pictures naked and even ate lunch naked. And it was great having a pussy there. Whenever one of us felt his cock getting hard, we just bent Judy over and stuck it in her. We must have fucked her ten times today, and she usually came too."

He shook his head.

"You've got an amazing wife, Dude," he said. "I was thinking of postponing your wedding tomorrow so I could use her a couple more weeks but I think I'm going to let her marry you."

"Thank you sir," I said. And I meant it. I had no doubt that Jason could keep Judy as long as he wanted.

"Oh. One thing," he added. "I want you to leave your room tomorrow an hour before your wedding. I'm going give Judy a load of quality sperm as a wedding present and I don't want you there."

"Yes sir," I said.

"I always wanted to fuck another man's bride on her wedding day," he said. "You don't mind if I fuck your bride, do you?"

"No sir," I said obediently.

"Good boy," he said. "I'd really like to show you the pictures we took today but Judy threw the camera overboard."

"However," he went on. "I remembered how she took your camera away, after you took those nude wedding photos."

He held up a small black chip like a trophy.

"So I pulled out the memory card when she wasn't looking," he said proudly. "The whole day is right here."

He tossed it to me.

"Souvenir of your trip to Jamaica," he said.

The next morning I woke to the luscious feeling of a naked Judy snuggling against me from behind. Her small hand stroked my rigid dick. I drifted between sleep and wakefulness and savored moment...then the terror hit me.

"What are you doing?" I said slapping her hand off my cock. I was terrified what Jason might do if he learned that his girlfriend had touched my cock.

"Come on," she said like a spoiled child. "There's nothing wrong with your dick."

"You're not supposed to touch my dick until tomorrow," I said sternly.

"I'm horny," she said pleadingly. "Your fiancée wants to get laid before her wedding."

"I'm sorry babe," I said. "I just can't."

"Ok," she sighed. Judy rolled me onto my back and kissed me on the lips. "Richard I love you so much."

"I love you too," I said feeling every word in my heart. "More than you'll ever know."

"I can't wait to be your wife again," she said. "It's going to be perfect...pure. And it's going to last forever.

She jumped into my arms and we held each other tightly.

"I know," I said with my face covered with her pretty, fragrant hair.

The wedding was planned for eleven o'clock so we began to dress as soon as we'd showered. Judy donned a simple white spaghetti strap dress of cotton. It went all the way down to her bare feet. The dress material was loose enough that she didn't need a bra so underneath all she wore were white panties. Jason's cook brought us flowers and Judy put some in her hair and pinned one to my Hawaiian shirt.

When I'd finished dressing I sat on the bed and watched her finish her make-up. She was so beautiful I almost couldn't stand it. I went to where she sat and put my arms around her, careful not to spoil her work. She placed her arms over mine.

Suddenly Jason barged into the room. I looked at my watch. It was ten o'clock.!

"What are you doing in here?" he said to me.

"I..." I stammered too afraid to answer.

"The groom isn't supposed to see the bride before the ceremony, you mope," he said. "Get out of here."

"He doesn't have to leave," Judy told him. "Richard, don't go."

"No," I said moving towards the door. "He's right. I'd better go."

"Please Richard," she pleaded. "Stay. Don't leave!"

"I've got to go," I said moving towards the door. I knew that if I delayed my departure Jason would punish me later. "I'm going out to talk to the pastor."

I closed the door and then paused to hear what they said to each other.

"It's Friday, Jason," she said angrily. "It's over."

"You're not married yet."

"Let me go," she said and I heard movement in the room, perhaps a struggle and then the sound of a kiss.

"Just one more time," he said.

"No," she said more softly. I heard them kiss again.

"It's my wedding day," she whispered.

"I know," he said almost too soft to hear.

The sound of rustling clothes and bodies falling onto the bed slipped through the door. I wasn't surprised but couldn't help feeling dejected, so I left. I went outside and saw the pastor but no one else was there yet. I sat in a folding chair and waited as Jason fucked my wife for the last time...I hoped.

Gradually people arrived. Just before eleven o'clock Doctor Feel-good showed up.

"Congratulations Mon," he said as we touched fists in the Jamaican way. "She's a special woman."

He smiled triumphantly.

"Thank you Doctor," I said politely.

"Ja mon."

Just then Jason came out with Judy on his arm. Judy's dress was a bit disheveled and there were no flowers left in her hair.

"Let's get this show on the road," he said. "I'm giving the bride away. I think that's appropriate, don't you Richard."

"Yes sir, " I said automatically.

"Uh oh," Judy said. "I need to go to the little girls' room first."

"No you don't," Jason. "Come on. This won't last long."

"Yes I do," she said forcefully as she tried to pull her arm free from his grip.

"No," he said laughing. "Look the pastor's waiting."

He dragged her to the dais and I followed. The ceremony was short, which was fortunate because we just had time to pack our bags before we had to leave for the tiny Negril airport. Jason had decided to stay longer so I called a cab to drive us there.

"I'm going to miss you," Jason said to Judy as the cab arrived. He put her bag into the boot and wrapped her possessively in his strong arms.

"I'm already sorry I agreed to give you away," he said. He kissed her much longer than mere friends kiss. Judy pulled away, jumped into the back of the cab and closed the door.

"It's too late," she said out of the window. "Richard, hurry up and get in. We're going to miss the plane."

An angry Jason disappeared behind us as the cab sped away, down the bumpy single-lane road.

We didn't talk much on the plane back to Chicago. I began to worry about what Jason would do when he got back. He had beaten me into submission and established dominance over me. But worse, I was sure that he'd want to fuck Judy again and there was nothing I could do to stop him.

We landed at O'Hare airport, got our bags and began walking towards the taxi stand.

I grew depressed as we rolled our bags past dozens of airline departure gates. Each step brought us closer to my evil boss.

"'Stop!" Judy said. "Richard, look." She pointed towards a departure gate.

"What?" I said.

"That plane's going to Honolulu," she said.

"So?"

"Let's go!" she said.

"Have you lost your mind?" I said.

"No," she said firmly. "I think I've finally found it. We've got nothing here in Chicago. I'm unemployed, you're in a thankless job and we hate the weather!"

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