The Challenge Ch. 01

"I hope so." Ray said nervously.

"Do you love your momma?"

"I do. Very much so."

"Then give her a kiss." Julie ordered.

Ray nodded, leaning down to give her a long, tongue-wrestling, kiss on the mouth. "Mmm, love it!" Julie exclaimed, slapping at Ray's butt playfully as they exited their room.

Out on the beach, Julie and Ray wandered into the water, holding hands. They waded out to deeper waters, around five feet. He bent at the knees slightly, and was at eye level with her. She threw her arms around him. Ray got brave again, placing his hands on her waist. He slowly slid them down over the rise of her butt and rested them on her ample, muscular cheeks.

Julie gasped, "Ray!" She smiled and kissed his lips. "Keep them there." Ray nodded and Julie hopped on to his waist, wrapping her legs around him, straddling him. Ray slowly moved out to even deeper water, around five and half feet. He gently squeezed her butt cheeks and held her in place.

As Julie was straddling her son, she made sure to squeeze her legs around him tightly. They kissed, laughed, flirted, and talked about sex. He would ask her general questions about her history, experience, and birth control. She talked openly about the dull sex with Ray's father - explaining it was always brief and not very pleasurable. She told him about Bob and having sex with him. She told him about Ulysses and how great a lover and friend he was. Ray wondered if he would ever be able to be an amazing lover. His mother reassured him that he would be, reminding him that practice makes perfect.

"I would say, since your dad left," Julie looked up to the perfect blue sky to do some math in her head while her son continued to squeeze her butt, kneading the meat gently, "five years ago, it's been around 40 different men I've slept with."

Ray's mouth dropped open, "Forty?!? No way! Are you serious?!?"

"Yep. All were just friends, until they developed romantic feelings for me, then we no longer had sex. I'd be sleeping with two or three, one of them would say they wanted to be my boyfriend, and I'd end it. I'd find another to be friends with to fill the gap. Some were friends of friends, others were coworkers, and so on."

"Wow, I had no idea." Ray said, staring blankly out to the ocean behind his mother.

"Well you and I didn't hang out as much as we do now. So a lot of those weekends I was out on dates, or during the week after work I'd meet up with a friend. By that time you were already in the bed asleep."

"Yeah, you're right." He blinked his rapidly, trying to process this.

"I love sex, Ray. I love it. After your dad left, it's like something was awoken in me. I feel more powerful and strangely enough, more confident. I would go out, meet a guy, and," Julie paused, stopping herself from saying the F-word in front of her son, "we'd have sex."

"See that couple over there, sitting on the beach?" Julie asked.

Ray looked over her shoulder at the gigantic, bodybuilder-looking, black man and his tall, muscular, blonde companion. "Yeah? What about them?"

"He's been checking me out since we got to the beach. I'm confident enough that if I worked a little magic and said the right things, he'd sneak away from his woman and come have sex with me. I've seen the look on his face when he checked me out earlier."

"Really?"

"Yep, and you know what else? I think you should hide in that closet in our room, and watch me put on a nice show for you with him. You'd see just how amazing it'd be to have sex with me," Julie explained, slowly dragging her tongue across her son's lips.

Chapter 13

The mother and son planned it out perfectly. Ray agreed to watch his mother "perform" for him and to wait in the closet for their arrival. Julie made sure he was comfortable with seeing her naked, teasing him that she wanted to see him naked soon.

It was around 10 pm, and Ray sat waiting in the large closet, idly stroking his cock. It had regained its strength after his mother's "desert blow job" from a few hours before.

Julie had spoken to the large black man, named Ronnie, at the poolside bar earlier in the day after leaving the beach. They made plans to meet up later in the evening at the resort's nightclub. She never mentioned his companion, though assumed she would be there with him. She knew with a few well placed "accidental" touches on the dance floor and seductive smiles that he would sneak away with her for a quickie.

Ray's eyes shot open when he heard their room door open, and two people barged in, backed by kissing sounds. He peered out the slightly open closet door into the dimly lit bedroom. His mother was pushing Ronnie back toward their bed, hungrily sucking face with him, and unbuttoning his shirt.

"You sure you're woman won't wake up?" Julie asked in between kisses.

"Valerie isn't my woman. She's just some bitch I'm fucking from the gym I go to. I made sure she drank way too much, she should be cold baby." Ronnie explained.

"I see. Well I'm a bitch you're going fuck now!" Ray nearly choked on his inhale when he heard his mother use that language. He watched her push Ronnie back on the bed. Not taking her eyes off him, she pulled his black pants down, followed by his boxers.

"Yes!" She shouted when she saw Ronnie's massive dick standing at attention for her. She grinned and quickly went to her knees. She grabbed it at the base with both hands and began to devour the huge cockhead, moaning as she worked, glancing over to where she thought Ray would be.

Julie stood up, "Are you ready?" she asked Ronnie, but was mostly thinking Ray in her head.

"Yeah baby, we should probably hurry though."

Julie nodded and slowly reached down to pull her dress up. She wasn't wearing panties. She drew it up slowly past her stomach. Her huge, braless, triple D breasts plopped out when the dress was raised over her chest. She tossed it to the floor and ran her hands up and over her body. Ray's mouth and eyes were wide in shock. He couldn't take his eyes off her. He watched her move her hands over her tight tummy and grabbed her breasts before mounting the man in their room.

Julie guided Ronnie's cock inside her and got to work. Ray watched her throw her head back and run her hand through her hair while she ground herself against Ronnie. He'd reach up and grab her breasts, holding them in place as Julie began bouncing wildly on his cock. Ray was masturbating furiously at this point.

After five minutes of riding and grinding, Julie hopped off the bed and on to the floor. Just like she had done back at home in the shower with her dildo, she reached back behind her and guided Ronnie's cock into her stretched pussy. She moaned as she slammed her butt down on it over and over again. Thoughts of Ray watching her, touching himself whilst watching her, raced through her mind. Not once did she think about the challenge or the money when her orgasm over took her.

"Ah shit!" Ronnie cried out, pumping Julie's pussy full of semen. When Julie could feel his cock stop pulsing and spurting cum, she went back to her knees and cleaned him thoroughly with her mouth.

"I'm going to have to make a trip to Atlanta at some point and meet up with you again. Damn!"

Ray watched his mother pop Ronnie's cleaned cock out of her mouth, "You do that. My sister lives in Charleston too. Hitch a ride with her and we'll have a threeway," Julie lied, knowing she'd probably never see this guy again.

"Will do." Ronnie rose up and buttoned his shirt. Julie retrieved his pants for him. After he put them back on, she walked him to the door, kissing him goodbye. She shut the door and headed to shower, humming to herself as she walked. She winked at Ray in the direction of the cracked closet door as she walked past. He groaned and ejaculated.

Chapter 14

Ray slowly crept into the bathroom where his mother was showering. She was humming to herself. "Is someone there? Hello?" Julie playfully called out to her son after seeing his silhouette behind the shower curtain.

"Oh my! It's you. Does this mean I get to see you naked now?" She teased her son. He smiled bashfully and looked downward.

"Did you enjoy my little show?" Julie asked, closing the shower curtain and splashing water onto her crotch to wash away more of Ronnie's semen.

"I did. It was very hot."

"Hot? You thought it was hot? Ooh that makes me hot!" his mother teased.

"I uh, I ejaculated from watching it."

"Good! I was hoping you were in there masturbating to me." Julie said, rinsing her hair. "Hand me that towel sweetie?"

Ray grabbed the towel and handed to his mother. Julie had turned off the shower and flung open the curtain. He tried to be discreet when he glanced at her naked body. Julie wrapped the towel around her body and stepped out of the shower. Ray followed her into the bedroom. He glanced at her butt as she let the towel drop before him. She grabbed one of the bath robes their room came with and put it on. She climb into the bed and got under the covers, patting the mattress for Ray to join her.

"We should get some rest. It's been a long day of travel." Julie said to her son as he climbed in with her.

With his face inches away from her, he nodded, and then slowly kissed her lips, causing her to moan. "I love you," he whispered, "and I think I'm ready. Tomorrow?"

Julie caressed her son's face and nodded slowly. Her eyes were heavy, "It's going to be wonderful. I'll take care of you; you have nothing to fear Ray." Julie kissed him back. They fell asleep a few minutes later, their foreheads touching.

The next morning they had breakfast at the resort's cafeteria. They served breakfast and lunch, but not dinner since there were several restaurants on the location for guests to choose from. They sat quietly, sharing glances and smiles at each other, occasionally holding hands. Ray was feeling more confident and on the way back to their room, he rested his hand on her butt as they walked.

"Let's try out this hot tub, shall we?" Julie said as the entered the room. She wanted to jump his bones right then and there, but reminded herself to relax and take things slowly. Ray admitted he was ready, but she still worried about freaking him out.

Ray sat in the bubbling hot tub and watched his mother, wearing the same pink, black polka dotted, thong bikini from yesterday, ease into the water and make her way to him. She tousled his hair and sat down on him, her gorgeous breasts grazed his forehead as she lowered herself into straddling position.

"Hi there." She said, wrapping her arms around his shoulder.

"Hi yourself," Ray smiled up at her. Julie gazed into his eyes, unable to look away.

"I can't wait to make love to you tonight. We'll spend time together this afternoon, we'll go get a nice dinner, we'll go for a walk, we'll kiss under the moonlight, we'll head back here and I will give myself to you in every way."

Ray gulped and nodded slowly, his hands resting on his mother's ass. She slowly bent down kissed him. "It's going to be wonderful."

"I hope so. It's just I've never done it before and that guy from yesterday," Ray sighed, "he's a lot bigger than me. You know, down there."

Julie burst into laughter, "You think that matters to me? Don't you know who I am? I am the one woman on this planet that loves you unconditionally. Small penis, big penis, no penis for that matter - I love you with all my heart already!"

"Oh, yeah, I guess I see your point."

"See that's why we're going to have so much fun doing this. I don't care if it lasts five minutes or five seconds. I'm not just some girl! I'm your mother."

Ray nodded and caressed her face with one hand and with his other massaged a butt cheek. He brought his lips to hers sharing another passionate kiss. The kiss coupled with the hot water caused Julie to melt. She sank into him, dragging her breasts across his chest, and rested her head on his shoulder.

"How do I look, Ray?" Julie asked standing before her son later that evening. She was wearing a short, red sun dress, low cut in the front, with matching high heels.

"You look great, mom"

"Do you think I'm sexy?" Julie asked taking a step closer to her son.

"Very." He replied, lifting the front of her dress, seeing she wasn't wearing underwear again, he ran his fingers along her moist slit. "Nice," he smirked.

After dinner they shared a chocolate cake and played footsy under the table. On their moonlit romantic walk, they held hands. They walked out to the pier and watch the waves crash into the nearby rocks. The water was reflecting the full moon. Ray held his mother from behind and pulled up the front of her dress. He slowly massaged her clit, looking around to see if anyone was on the pier with them. He saw no one and began kissing her neck like she loved so much. After several minutes, she began to shake.

"I love you," he whispered in her ear as she came for him.

Back in their room, Julie and Ray stood facing each other, both wearing the large, white, bathrobes that came with the room. The lamp in the corner was the only light on.

"I still haven't seen you naked yet, so you go first." Julie said, reaching out to pull the tie on his robe. He finished removing it, letting it fall to the floor. Julie smiled and looked him over - thin as a rail, lanky, but with a healthy, nice erection for her.

"My turn, pull my tie here when you're ready." She instructed her son. Ray took a deep breath and reached out to her tie, pulling it gently. She wiggled out of it, letting it too, fall to the floor. She took a step closer to Ray and placed her hands on his shoulders, smiling up at him.

Ray nodded, "I'm ready."

"Then come to bed," Julie said, grabbing his hand and leading him to the bed nearby. She climbed in first. Lying on her back she motioned for him to join. He slid in next to her. Ray glanced at her breasts, then up at her face. She nodded. He slowly kissed the nipple nearest him, and then cupped the breast, suckling on it gingerly.

"Do you like it?" He asked.

"I love it." Julie replied as Ray continued kissing and sucking her nipple. After several minutes she stopped him, nodding at him, scooting down the mattress a bit. Ray knew what to do. He climbed on top of her. She opened her legs, wrapping them around him.

"Very good. I'm going to guide you in, and we'll have fun. Ok?" Julie said, grabbing his cock and slowly guiding it in. Ray gasped as the tip entered her. He moaned as her walls gripped his shaft tightly. Julie smiled and closed her eyes, a satisfactory grin on her face, when she felt Ray was all the way inside.

"Ok, you're in now. I think you know how this works, right? Move your hips and have at it!"

"Ok," Ray smiled and did just that. Slowly at first, he moved his hips and began thrusting in and out of her, looking down at his cock, making sure it didn't come all the way out. He would glance back at his smiling mother and nod. "I'm doing it!"

"I know! You're doing a great job too!"

He kept going; it felt amazing, he knew it could not hold out much longer. Julie knew it too, caressing his face as he worked. "There we go, just like that sweetie, just like that. You're doing it!"

"Yes!" He nodded and focused his attention on his mother's face. He kept pounding faster and faster and within, what seemed like seconds, he grunted and ejaculated in her.

"That's it Ray! Hold still!" Julie said, holding his face, watching him wince with pleasure as he injected semen into her. She couldn't help but tear up as she saw the joy on his face.

Ray collapsed on top of her, and Julie ran her fingers through his hair and then scratched his back. Knowing his first time would be quick, she loved every second of it.

"Did I do a good job?" Ray asked, after he caught his breath.

"Oh sweetie, you were perfect!" Julie replied, holding his face and tearing up again. "You're perfect." She kissed his lips slowly and pushed him off her. She rested in his arms and ran her fingers up and down his tummy.

Chapter 15

"Ugh, ugh," Ray grunted a couple hours later, on top of his mother.

"That's it baby, you're doing so good!" She encouraged her son, locking her feet around his butt, driving him deeper. He cried out and shook as he came inside her again.

Later in the evening Julie moaned, biting her lower lip, as Ray gritted his teeth and came in her again after 15 minutes of hard pounding.

Just after midnight, Julie rolled on top of her son, and began grinding into him. She grabbed his face, kissing him hard as orgasmic waves rippled through body.

A couple hours later, Ray slammed into his mother from behind, her eyes rolling in the back of her head. He again pumped her full of semen and collapsed on top of her. She reached over her shoulder and tousled his hair again.

Ray was sucking hungrily on her tits a couple hours after that, as she rode him, while he sat on the bed. She came within minutes. She had several orgasms the next 30 minutes until Ray finally had his.

"Yes! Like that!" Julie grunted back to Ray. He was holding her arms and thrusting mercilessly into her from behind as they stood in the bathroom above the toilet. Ray had taken her by surprise right as she was flushed, spinning her around and having his way with her. It was close to 6 am.

A couple hours later, the two lovers sat in the hot tub. The morning air getting warmer. Julie was slowly gyrating her hips to meet Ray's thrusts. They were exhausted. His head kept dropping, and she was resting her own on his shoulders. His eyes were closed as his finger gently circled her anus. Julie moaned softly, "Mmm, sweetie, I love you," she said above a whisper.

"I love you too," Ray replied. He sat up, grabbing his mother by her butt; he lifted her up and carried her inside, dripping water everywhere. He placed her gently on the bed and began fucking her. Staring intently into her heavy eyes with his own, he pounded into her with long, slow, but powerful thrust for several minutes until he told himself he had to sleep. They both came at the same time; their gaze remained locked on each other as Ray rolled off her. They fell asleep within minutes, laying side-by-side, their foreheads touching - totally exhausted.

Later that afternoon, Ray returned to their room with two 'to-go' boxes full of food from the cafeteria. He undressed and joined his mother in bed. They ate like they were starving. Afterwards, they had sex in the same manner.

"Ahh yess!! Yess!! I'm cumming again!" Julie screamed in the hot tub later that night, the water splashing all around them. Ray hadn't cum yet, he smirked as he watched his mother orgasm again. A few minutes later he threw her on the bed and turned her around. He slapped her ass a few times and continued his assault. Julie as about to cum again, when they heard a knock at the door. Her eyes shot open and Ray dismounted her. She grabbed her robe and quickly tied it.

"Hi. Yes?" Julie said to the employee of the resort that had been knocking on her door.

"Hello ma'am. We have received noise complaint. I am asking politely that you and your companion please keep it down." The employee explained.

"Ah yes, I'm sorry. We were just having sex out in the hot tub. I believe that was orgasm number 3 the neighbors heard." Julie said, causing both her son and the employee to blush and turn away with embarrassment.

"Um, yes, well anyway, please try to keep the volume down."

"Will do!" Julie said, closing the door in the employee's face. She disrobed and jumped back on the bed on top of her son.

The rest of the week was a blur of sex and sweat. In the shower, in the hot tub, in the bed, and in a restroom of one of the restaurants; they had sex everywhere at that resort. All except one location, a place Julie saved for last.

Julie floated on her back in the ocean, her eyes barley open, extending her arms perpendicular to her body as the cool early morning air kissed her nipples. They were scheduled to leave the Bahamas in a few hours. Ray was there too. He was slowly guiding his cock in and out of her pussy in slow, loving thrusts.