Risking Judy Ch. 04

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Judy begins to enjoy the boss's gifts.
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Part 4 of the 5 part series

Updated 11/01/2022
Created 06/30/2007
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Just before noon she left and I dashed back to my place by Jason's bed. Jason was reading a newspaper, and gave me the thumbs-up sign as I settled down on my cushions behind the towels.

When the knock on the door came he stood up. I was surprised when I saw that he was still naked and erect.

"Come in, Judy," he said.

My wife entered the room and shut the door behind her. Judy seemed relaxed and she smiled at Jason and noticed his erection.

"Richard and I are getting married again on Friday," she said. "This all ends on Friday...forever. Agreed?"

"Ok."

"And Richard doesn't learn anything about this or what happened last night," she went on.

"What he doesn't know now, he'll never know," he said. "I promise."

She took a step towards him, but he raised his hand.

"Lose the suit," he commanded.

As fast as she could, Judy pulled off the bikini, threw it on the chair and came to him.

This time I could tell she was sexually excited and that she was truly ready to have sex with my boss. I began to feel jealous and sick again.

They kissed hungrily and I noticed Judy was stroking his cock the way he likes.

He sat down and pulled her breasts towards his mouth.

"I'm already wet, Boyfriend," she said. "You don't need to fluff me."

Jason laughed and laid back on the bed. Judy squatted over his thick shaft like before. With one hand my wife guided Jason's penis to her opening, and with the other hand she spread her pussy lips. This time his cock disappeared into her body in one smooth fluid motion.

With his thick cock completely embedded in her womb, Judy shifted onto her knees and leaned forward to kiss him. After a few moments his hips began to pump his thick shaft up into her pussy. Judy's small ass rose and fell in timing with his thrusts. Gradually they picked up speed and I heard a soft slapping sound as their bodies touched. Judy groaned as his thick cock sliced into her with amazing speed. In just a few minutes she broke their kiss and arched her back.

"Oh God, Jason" she screamed. "So fast. You're making me come so fast!"

And a month of pent up sexual energy was released like an erupting volcano.

"Oh Goooood!" she screamed.

She bucked so violently that I thought she might knock the two of right them off the bed. Her orgasm went on longer that any I'd ever seen, with Jason pumping into her hard from below.

Finally, she collapsed on his chest gasping for air.

They rested for a while. He rolled her onto her back without letting his still hard shaft slip from her pussy and he began to fuck her again. This time he fucked her much slower.

I heard the slippery fucking sound lovers make. I heard the sounds of them kissing and watched as Jason pounded his shaft over and over again into my wife's receptive body. Judy wrapped her toned legs behind his calves and held him around his neck with her slender arms. She groaned quietly as he fucked her gently, with slow deep strokes. The smell of sex filled the room as I began to feel sick again.

After what seemed like hours of deep luxurious fucking he increased his speed until his hips were almost a blur. Instantly Judy came again.

Jason could control my wife's body in a way I never could. I was horrified, hurt and jealous. I was furious at myself for starting all this. I wanted to cry and run away, but I couldn't. I threw up on the patio a second time.

"Oh Yes! Oh God Yes!" she screamed as she orgasmed on his enormous shaft, arching her back off the bed and scratching his ass viscously with her nails.

And then he came.

"Here it is, Girlfriend," he said as he reached under her, grabbed her ass and pulled their bodies tightly together.

He plunged his huge cock deep into my wife and began to fill her with his seed.

"Yes, lover yes," Judy said. "Give it to me."

She held his head and kissed him tenderly as he pumped his cum into welcoming pussy.

Finally, Jason collapsed onto the pillow next to her. His cock was so long that it didn't pull completely out of her. They tried to gather their breath.

They were still for so long I began to think they'd fallen asleep.

Finally, Jason propped himself on an elbow - his softening cock was still inside my wife. He smiled at her and she smiled back. They looked deeply into each other's eyes and I sensed that their mating had made them feel emotionally close.

He leaned down and kissed her gently.

"Judy, that was amazing," he said. My wife nodded.

"Is it like that with Richard?" he asked.

"We've been married a long time," she said softly. She reached up and gently stroked his hair.

"Was it ever amazing like that?"

I knew that he was asking her for my benefit.

"You're much...bigger than he is. You feel different than he does."

"You mean better?" he asked.

"Yes," she said after a pause.

I felt like my wife drove a stake into my heart. It wasn't bad enough that I had to share my love with another man. Not bad enough that I had to watch him fuck her and bring her to orgasm twice. But she admitted to him that she liked how his cock felt in her body more than mine!

"Have you ever fucked a man with a big cock like mine?"

"Why is it that men care more about penis size than women?" she said.

"Come on," he persisted. "Did you?"

"Yes. One," she said impatiently.

"Well?"

"A boy I dated in high school had a big penis, but not as big as yours. He popped my cherry at the after-party of the Junior Prom and I found out how amazing sex was. Then we spent senior year looking for any dark spot to be alone. We did it in a stall in the boy's bathroom at school, in his parents' bed, on the pool table in his garage. We kind of went crazy," she said laughing.

Jason kissed her.

"That's when I learned to give hummers. My mother would never have let me get on the pill, so I always made him come in my mouth. It was natural birth control for us."

It hurt more when I realized that Judy was telling Jason, more about her sex life than she had ever told me.

"I can feel you getting hard again," she said with a smile.

"I have to cum twice when I shag," he said. "Or I get the worst case of blue-balls. I think my balls just make too much jism."

He got between her legs again and pressed his hips forward, forcing his cock into her a little deeper.

"Ouch," she said.

"Let's do it again," he said.

"On no, boyfriend," she said pushing him off her. His hardening cock popped out of my wife's pussy. "I'm sorry, sailor but this girl is too sore. You're a little bigger than I'm used to."

My boss sat on the bed, his fully erect cock shiny with his cum and my wife's lubrication.

"Can I suck you off instead?" she asked.

"Well, I guess so," he said feigning disappointment.

"You jerk," she said playfully slapping his big cock.

"Lay on the bed with your head over the edge," he said. "It will be easier for you to swallow my cock that way."

"I don't think I going to be able to swallow it," she said sliding around on the bed. "I'm not very good at deep-throating."

He guided her so that her upside down face looked directly at my hiding place behind the towels.

Jason went to the dresser and brought back a small white jar.

"This is deep-throat oil," he said. "It comes from Thailand. My cock will slide right down your throat. You'll be amazed."

"Ok," she said uncertainly.

He opened the jar and drew out a finger full of white slime that looked a little like soft butter and wiped onto the roof of Judy's mouth. She kept her mouth open waiting for him to mount her head. Jason straddled her head and slowly guided his cock into her mouth. My wife held onto his muscular legs as he began to work his cock in and out of her mouth - using it like a pussy. Judy made a few gagging noises but it wasn't long before his enormous cock was disappearing down her throat with every thrust.


"Good girl," he said. "I knew you could take it all the way down."

Each time Judy started gagging he'd pull his cock out of her mouth and let her catch her breath before sliding his shaft back down her throat.

"I know this is hard for you baby," he said. "I'll try to come fast."

'Considerate asshole!' I thought.

He put his hand on her throat as he fucked her.

"I can feel my cock going down your throat! You are such an awesome cock sucker." "So good! Judy your mouth is so fucking good!"

His fucking motions became jerky and his ass muscles contracted and I knew he was close to cumming. His cock fell from Judy's mouth.

"I'm gonna cum now, baby. Are you ready?" he asked.

"I'm ready," she whispered.

Jason plunged back into her mouth and his cock exploded.

"Oh you bitch," he groaned as he force-feed sperm directly into my wife's tummy.

She sealed her lips tightly around his thick shaft to catch all of his bountiful ejaculate.

Finally he drew his softening shaft from Judy's mouth and collapsed onto the floor next to her. Judy tried to catch her breath as they hugged each other.

"You're wonderful," he said.

Judy smiled like she knew it and wiped his cum off her lips.

"Did you like how my nut tastes? Men are different, right?" he asked.

"Yes," she said.

"Did you like it?"

"You taste nice."

"Better than Richard?"

"It doesn't matter," she said kissing him. "But I'd better get back" She rose and went to where she tossed her bikini.

"Come on, tell me," he persisted following her to the chair. "Does my cum taste better than your husbands?"

Judy gave him an annoyed look.

"Richard's sperm is a little bitter," she said at last. "You taste fresher – sort of like the ocean."

My humiliation was complete.

I knew he had made her say those things for my benefit. I knew Jason was playing a game to prove that he was top-dog. I didn't want to give him the satisfaction of seeing me hurt, but I couldn't help it. I was crushed and I couldn't hide it.

"Tomorrow at 10:30? " he asked as she slipped into her bikini.

"Ok," she said. "But remember, no sex after Friday. After the wedding I'm Richard's faithful wife again. Forever!"

"I know," he said. Then he kissed her. "But until then you're my girlfriend," he said.

"Good bye Boyfriend," she said as she went out the door.

Jason came over to my hiding place and looked over the towels.

"Stand up," he ordered. I did as he said. All my strength and ability to resist him had been totally crushed.

"Be back here tomorrow morning for the next show," he said. "You're going to watch as your wife falls in love with me."

I would have thrown up again if I had anything left in my stomach.

"One more thing. You're not going to say or do anything to stop her from coming to me, or she finds out what a prick you are," he went on. "Is that clear?"

"Yes sir."

"And you don't lay a hand on her," he said forcefully. "Judy is mine."

"I understand, sir."

"And she doesn't touch you either. Not even a hand job. You can wank yourself," he said. "I'm going to ask her what you're doing so don't think you'll sneak a quick poke without me knowing.

"I won't, sir."

"Ok. Get out of here."

I went back to the lounge chairs and Judy was there in just a moment.

"Hi," she said flopping into her chair.

"Hi. How was the class?"

"What? Oh it was wonderful," she said. "The teacher was amazing."

Judy seemed happy and relaxed like she hadn't been for the last thirty days.

"Are you going back tomorrow?" I asked trying to sound as if my heart weren't breaking.

"Definitely!" she said. "It did me so much good." She put her headphones on and got comfortable. "But I think I need a nap now."

"Judy," I started. "I have bad news. My infection is back. I don't think we'll be able to fuck for a while."

"Oh, that's too bad," she said sounding not the least bit unhappy.

"But I should be ok after Friday," I said.

"Ok," she said softly as she fell asleep.

I laid there with my eyes closed and visions of Jason fucking my wife filled my mind. I opened my eyes and rubbed my head. All I had to do was survive a few days and I'd get my wife back, I told myself.

I watched chubby tourists play in the blue water.

"I just hope I can survive tomorrow," I whispered to myself.

The next morning was nothing like the first. Judy woke in a happy playful mood and attacked breakfast like a wolf. She and Jason were polite to each other when I was around, but they always seemed to be whispering or tickling each other when they didn't think I was looking.

Judy and I tanned together on the beach after breakfast. At 10:15 she took off her headphones and began to put on her colorful wrap skirt. (I assumed her muumuu was doomed to stay in Jason's garbage.)

"I'm off to my class," she said cheerfully. She bent over me and kissed me on the lips.

"Have fun," I said.

"Oh, I will."

She strode off down the beach with a swing in her hips I hadn't seen for quite a while. I guessed 'something snapped' like Jason said it would, because Judy certainly seemed to be a very 'happy puppy'.

As I dashed across the grass I felt myself getting hard, and noticed the distinct lack of nausea I'd felt the day before. Strangely, I found myself actually looking forward to watching Jason and my wife fuck. I felt a little frustrated not being able to fuck my wife, but mysteriously, all my jealousy and anger were gone.

I figured that something had 'snapped' for me too.

When I got to my cushion I was startled to see that I was late. Judy and Jason were already naked and kissing.

Judy must have run to his room!

As they kissed my wife pumped his cock with her hand while he kept a firm grip on her small round ass.

He slid his hand down her ass and between her legs.

"You're wet," he said. "I guess you've been thinking about me."

"I haven't been thinking about you. I've been thinking about this," she said lifting his cock.

They both laughed. Then he lifted her off the ground and my wife wrapped her long lithe legs around his waist. He hooked his arms under her legs as my wife held tightly onto his neck.

"Put it in," he said.

Judy reached between them and guided his penis to her opening. He lowered her and his cock slid deep into her body. Judy wrapped her arms around his neck and held him tightly. I'd always wanted to fuck my wife standing, but I wasn't strong enough to hold her up very long. I was afraid that we'd fall or I'd drop her. Jason held her effortlessly.

"Oh God," she said with enthusiasm. "Boyfriend, you feel so good."

He walked to the patio door with my wife still impaled on his monstrous hardness. He turned so Judy's back was towards the door and moved forward until his legs touched the towels that concealed me. Judy's ass was directly above my head. Jason wasn't done humiliating me. I knew he wanted me to have a good view of him fucking my wife without her seeing me.

He lifted her with his strong arms and I had a close up view of his cock emerging from my wife's grotesquely stretched pussy. He slowly lifted her until I could see her thin inner lips wrapped tightly around his round cock-head. Then he slowly lowered her and his shaft disappeared back up into my wife's womb.

"Oh Jason, you're so deep!" she moaned. "Slow baby, please."

He began to fuck her with long slow strokes and I realized that even though I had fucked her hundreds of times, I'd never really seen my wife's pussy stuffed full of male organ. I discovered my wife's pussy looks beautiful with a thick cock inside it!

Beautiful and so erotic that I thought about cumming myself. Jason and Judy weren't looking and the patio was completely surrounded by the bougainvillea plants. I probably shouldn't have, but I actually pulled out my stiff cock and began jerking it.

I watched with thrilled fascination as Jason lifted Judy up and down on his shiny cock. Faster and faster until she began to make the unmistakable sounds of approaching orgasm. My wife and I were less than two feet apart and we were both ready to cum.

In fact all three of us came together. "Oh Jason," she wailed. "Oh lover you're making me cum!"

She drove herself down hard on his manhood as Jason roared with the power of his release.

Actually I was glad they made so much noise, because I couldn't keep myself from making a little noise when I came too.

I shot my sperm onto the patio stones as Jason shot his sperm into my wife.

I could see his ejaculation muscle under his cock pumping as he filled her. He came for a long time while Judy just rested her pretty head on his muscular shoulder and let him fill her womb with his seed.

A small amount of Jason's sperm leaked out of Judy's pussy and ran down her ass forming a growing puddle over my head. Now that they were quiet I couldn't move without making noise. All I could do was watch as Jason's cum dripped off my wife's ass and landed on my neck. It was humiliating beyond endurance to feel another man's cum dripping out of my own wife's pussy and onto my head and neck but there was nothing I could do.

He carried her to the bed and gently laid her on her side facing where I sat hiding.

My wife's perfect body was just an arm's length away, but I couldn't touch her. Only her boyfriend could.

Her eyes were closed and her heavy breasts rose and fell as her breathing returned to normal. Her pink nipples were rock-hard and I could see the areolas were wrinkled and contracted. Jason crawled in behind her and kissed her neck. My wife smiled and reached back to caress his face. I watched a heavy stream of cum flow out of her pussy, over her thigh and onto the bed.

They snuggled together in post-coital bliss and waited for Jason's extraordinarily short refractory period to end.

"Are you too sore for me to fuck you a second time today?" he asked after a few minutes.

"No," she said. "You stretched me out yesterday. A good aerobics instructor wants his students to stretch and I'm stretched."

They giggled as he prepared to enter her again. He lifted her top leg and slid close behind her. He poked his long shaft between her legs and it almost made Judy look like it was her cock. In a way, it was.

He pulled back, changed angle and pushed the head towards my wife's pussy but it bounced forward and didn't enter her. Judy reached down and forced the head into her opening, and then he slid the rest in. Jason laid down behind her so all I could see of him was the shaft of his cock when it withdrew from my wife's wet hole. She closed her eyes tightly as he began to mate with her again.

Gradually I got hard again too. I carefully laid down sideways on the patio, facing Judy and began trying to stroke my cock. I didn't look at my cock because its small size was starting to depress me. I just watched my boss's donkey dick pumping in and out of my wife and I pretended it was my big cock that was fucking her from behind.

I timed my strokes to match Jason as he shafted her and for a moment I really felt like I was fucking her instead of Jason. She was so incredibly lovely. From her perfect small feet to her long smooth legs, to her tight pussy to her gently swaying breasts to her girlish face, she was a goddess!

It was all so erotic that it wasn't long before I felt the cum in my balls ready to explode, but Judy came first.

"Oh Jason! You're making me cum again!" she moaned as she came, making a hideous face that looked like she was in pain.

I came next. It felt great, but just a few drops fell from my cock onto the stones.

Jason pulled his cock out of Judy's pussy.

"Woo, Girlfriend I'm really close," he said. "Where do you want my jism this time?"

My wife reached between her legs, took his cock in her hand and stroked it slowly.

"I want to watch you cum, Boyfriend," she said. "I want to hold your big penis in my hand and feel it when you cum."

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