The Challenge Ch. 01

"Ray, how about more than just a hug?" Julie asked.

Ray gulped and nodded.

Julie rose on her tip toes again and kissed his lips. It lasted for about five seconds. She smiled and wiped his lips with her thumb. "There. See, not so bad right? That wasn't too gross was it?"

"No, it was fine." Ray replied, smiling weakly.

"Good. Next Saturday let's stay home and watch a movie? Alright?"

"Ok, sounds good."

The following week was similar to all previous weeks. Julie would get home late and Ray would be either asleep or close to it. She was sick of the late shifts and overtime. She made it a point to speak to him or hug and kiss him before heading to bed.

"Yes, it's these shorts again!" Julie teased Ray the following Saturday night, hearing him enter the living room behind her. She was turning on the DVD player. She sauntered over to Ray and sat next to him.

"Arm." She nudged his side and he lifted his arm placing it back behind her on the couch. "No, put it here," she grabbed his hand and put it on her thigh. "I wore these shorts for a reason silly."

"Oh right." Ray rested his hand on her thigh, this time on the side of it, since she was leaning into him on the couch and not sitting on his lap.

They sat like that the entire movie. Ray would squeeze and massage her thigh, occasionally trailing it with his fingers. Julie smiled, thinking about how he was getting more comfortable with her and himself. Plus it felt good.

As the weeks went by, they held hands more often; they exchanged more kisses on the lips. Ray even slept in her bed a few times. Julie would lie against him, pulling her tank top up to reveal the small of her back. Ray knew immediately what she was doing and placed his hand there, gently caressing it. He'd run his finger tips up and down the valley of her spine. She shivered a few times at his touch.

The weekend before their trip to the Bahamas in March, Julie pounced on Ray, pinning him to the floor. They had been having a tickle fight. Ray was winning for the most part, grabbing Julie from behind tickling her side, her butt up against his crotch. However, she eventually got the upper hand and was straddling him on the kitchen floor.

"Got you." She said, looking down at him. Their smiles and laughter faded as they stared into each other's eyes. Julie was wearing similar tight shorts and a tank top and Ray in his standard t-shirt and pajama pants.

"How do you feel about me baby?" Julie asked, releasing Ray's pinned hands, and lowering herself inches away from his face. Her braless breasts smashed into his chest.

"I, uh, I'm getting more comfortable around you."

"Yeah? Are you thinking more about that money?"

"Mmhmm, it'd be great to have."

"Are you thinking more about sex with me?" Julie asked, kissing his cheek slowly.

"Well, um, I have been yes."

"Are you thinking about it now?"

"Umm, well, I - " Ray stammered, beads of sweat forming on his forehead.

"I think you are." Julie said, squeezing her inner thigh muscles on a very lovely erection that Ray was sporting.

He nodded quickly, eyes darting away from Julie's face.

Not wanting to rush things, Julie asked, "Do you think after our Bahamas trip next week, we'd be able to try it?"

Ray nodded again and cleared his throat nervously. Julie kissed his cheek again, then his jaw line, eventually making her way to his lips for a long, beautiful, kiss. "I think I'll take a shower."

Julie got off Ray and made her way to her bedroom. She stripped naked and grabbed her shower companion. Ray's erection was on her mind when the orgasm overtook her.

Chapter 10

"That was another great meal, mom." Ray said the following night.

"Thank you! Here give me your plate." Julie said, making her way to the kitchen sink.

She was rinsing the dirty dish when she felt a pair of hands on her shoulders. Ray was slowly massaging them.

"That feels great," Julie moaned, leaning her head back against Ray. She closed her eyes and instinctively arched her neck toward him. Ray paused. He licked his lips and slowly bent down to place a single kiss on Julie's neck.

"Mmmm, Ray that was very nice. I like those kinds of kisses."

Feeling uncomfortable, he backed away and smiled awkwardly at her when she turned around.

"I know what will be fun! A massage!"

"What? No, I'm no good at that."

"Get up those stairs now!" Julie teased, pushing and poking him along. He got the stairs and tripped, falling backward onto them. He dragged his mother with him.

"You better watch where you're going mister." Julie said, wrapping her arms around him as they lay there on the stairs. She looked into his eyes and placed another slow, long kiss on his lips.

"I like those," Ray spoke up after an awkward pause.

"Do you want kiss here a little bit on the steps before we head up?" Julie asked.

Ray nodded slowly and his mother climbed off of him, sitting next to him on the stairs.

"Ready?"

Ray nodded.

"Great, now just lean in and kiss my lips slowly." Ray complied. It was awkward and only lasted about three seconds before he stopped.

"Good! Now do it again, keep going, alright?" Julie said.

Ray nodded and leaned in again. His mother grabbed his hands, holding them as he kissed her mouth with long, loving, kisses. They sat there on the steps kissing for fifteen minutes. No tongue was used, just sweet, precious kisses.

"How was that?" Ray asked, slightly out of breath.

"It was wonderful Ray," Julie replied, her eyes still closed. She opened them and caressed her son's face.

"Maybe we can do it again soon?"

"I'd love to," Julie smiled, licking her lips then kissing his once more, wiping her saliva away with her thumb.

She stood and led him to her bed. "Ok you sit here, legs out like that. Like a V, alright?"

Ray complied and Julie climbed up onto the bed with her son. She sat facing away from him with her butt up against his crotch. She leaned back and Ray began massaging her shoulders. After several minutes of moaning and complimenting his skills, Ray got brave. He slid the spaghetti straps off her shoulders and continued massaging them. When she felt his breath on her neck she leaned back and closed her eyes. Ray kissed her neck. His hand trailed down to her arms and he kissed her neck again. Julie reached back and ran her fingers through his hair as he kissed her again and again along her neck. "Very good, Ray." She felt his erection against her back, she was out of breath. Ray pulled her shirt up and placed his hand on her tummy, feeling her abdominal muscles contracting with each kiss he planted on her neck.

"Ray, yes, yes baby." Julie whispered. She wondered if tonight would be the night, if they would earn that $20 million. Her spine was tingling with each kiss and then suddenly he stopped. He sat straight up and tried to catch his breath.

"What's wrong, are you ok?" Julie asked, sitting up and turning to face her son.

"Yeah, I'm fine, just uh, I'm fine." He replied, clearly overwhelmed by the moment.

"Ray, are you sure you're ok? " Julie asked again. Ray nodded.

"I can help you if you let me." Julie said, running her fingers down his torso, stopping just short of the budge in his pajama pants.

"I don't know." He said, looking away from her.

"Please? It'll be one step closer for us, you know?"

Ray nodded, still looking away.

"You don't have to watch me if you don't want to. Just sit here and relax."

Ray glanced at her long enough to see her hook her fingers in his pajama pants. He turned away, wincing as his mother tugged at them.

Julie's mouth hung open as air escaped it; her hot breath landing on her son's impressive erect penis. "Oh Ray," she whispered. She lay there looking at his cock as it slowly oozed pre cum. A smile came upon her face as her eyes teared up.

"It's beautiful," she whispered to her son. He just nodded, still unable to watch.

Julie closed her eyes and nudged the cockhead with her nose. She moaned as she took in his musky scent. She brought a hand to the base, causing her son to flinch. She wrapped her fingers around it and peppered the tip with soft, tiny kisses. She lapped up the oozing pre cum with her tongue, causing Ray to shiver.

Julie took one final look at her baby's penis, "This is it. One step closer to a new life. The money will be ours soon," she thought before opening her mouth and engulfing his cock. She took as much as she could to the back of her throat, coating it in her saliva. She then began bobbing her head up and down on it, sucking hungrily. Ray made a noise that sounded like he was going to have an orgasm, but he didn't. As she worked on his cock, she looked up at her son, she studied his face. She could only see the side of it, but she could tell he was wincing in pleasure.

"That's it baby, cum for me. Cum for mommy. We're working our way to be millionaires. Mmmm this taste so good." She thought as she slurped and sucked that juicy cock.

Ray kept making noises, "ahhs" and other various moans. He turned and looked at his mother working on him. Her eyes were fixated on his. He immediately ejaculated in her mouth.

"Mmmm!" His mother moaned and stopped bobbing up and down on his cock. His opened mouth quivered as he unloaded semen. He felt his cock pulsing as it filled Julie's mouth. He watched her throat swallow several times, her eyes never leaving his. He threw his head back and looked up to the ceiling in disbelief.

"See, I can help you if you let me. We can get through this," Julie said, sitting up on the bed and wiping her mouth with the back of her hand. "That was very good Ray, you did a great job!"

Ray nodded, quickly pulling his pants up over his shrinking cock. "Ok, well, thanks. I guess I'll go to bed now. See ya." He hopped off his mother's bed and scurried down the hall to his room. Julie couldn't help but laugh to herself.

"Silly boy."

Chapter 11

Julie lost count of how many times she sucked Ray's cock the next day. Waking her son in the morning by opening his bedroom window curtains and then snuggling up to him in his bed, she tickled him and climbed on top of him. She slid down his thin frame and pulled his pajamas pants down.

"Mmmm, I see something else is awake now too. Gonna let me take care of this for you?" Julie asked, swirling her tongue around the tip.

Moments later Ray was ejaculating into her mouth. Julie smiled, watching her son's stare up at the ceiling, panting heavily as he came.

Every couple hours for the remainder of their Sunday, she was on her knees in front of him in the kitchen, on her knees sucking him off while he sat on the couch, on her knees drinking his semen while he ate his dinner at the table, and finally jacking his cock off and lapping up the cum that would spray into her at bed time.

"Have a good day today?" Julie asked Ray later in the evening as the two of them lay in his bed.

"Yeah, I did."

Julie propped up on her elbow, "Are you getting used me providing you with sexual pleasure?"

Ray nodded and blushed.

"Good." Julie kissed his lips slowly, lightly lapping them with her tongue.

"Do you want to try that? Use tongues?" She asked.

Ray nodded, the two kissing again. "Lick at my lips, and then I'll do the same." His mother instructed. When his tongue touched her own she nearly melted, sinking into him, and swinging a leg over his waist. She held his face and continued kissing him, their tongues slowly circling the other, as she straddled him.

"See, it's not so bad, is it?" She asked her son, out of breath. He shook his head and they resumed making out. Julie slowly started grinding her hips into his. She was wearing a pair of his boxers. She moaned as she felt his throbbing erection slide against her moist outer lips, only two thin layers of material between them.

"I love you sweetie," Julie whispered, resuming her dry-humping and lapping at Ray's mouth.

"I love you too," He replied.

After several more minutes, Julie nearly had an orgasm but stopped herself; she didn't want to chance freaking him out. She broke the kiss.

"Ok, that's good. That was really nice." Julie said, sliding off her son, trying to regain her breath.

"Yeah it was." Ray said, looking back up at the ceiling.

Julie smiled at her son, caressing his face. She moved to his pajama pants and started doing what she had done most of the day, servicing his cock. As she was sucking him hungrily, she felt his hand on her head. He was running his fingers through her hair. She glanced to his eyes and he was watching her. He was no longer nervous about this. He smiled at his mother, lovingly playing with her hair while her head bobbed up and down on his cock. After a few minutes he nodded to her, she nodded back and stopped moving, allowing Ray to fill her mouth with semen. Moaning as she swallowed it down, not taking her eyes off him, not one thought of the money she was offered enter her mind - nor did it the rest of the night, or even the rest of the week. Each morning she woke up early and sucked him dry before he headed to school. Each night he made a point to stay awake for her hungry mouth. Each day Julie would think about him, the noises he made when she sucked him, and the taste of his semen.

Tuesday evening found her in her usual position of Ray's bed with her mouth milking his cock. He groaned as shot his load, gripping her hair a little tighter as he came. "Ahhh that was good mom. Wow."

"Glad you liked it." She smiled and continued licking up any cum she could find.

"Do you like it?" He asked watching her tongue lick at his shaft.

Julie paused and thought about her answer. She thoroughly enjoyed it and wanted to do it all day to him. It felt amazing and after every ejaculation he had, the happier she felt. "I love it."

Ray smiled at his mother. "You like the taste?"

"Well the taste isn't all that amazing. But something about it hitting my tongue, knowing I caused it to happen, can be quite empowering. At least for me it is."

"I see." Ray said, sighing and looking downward.

"What's wrong Ray?"

"Well it's just that, I was thinking maybe, uh, you know, I could do something to you? Seems unfair that you always are doing something to me."

"Yeah?" Julie asked, smiling up at her son, tucking his exhausted penis back into his pajamas. "You'd want to try touching me?"

Ray nodded, "It's just I've never touched a girl, you know, in that way." He explained, blushing as he looked to the side.

"Ray, it's ok, I can teach you. How about tomorrow night?"

"Ok"

The next evening Ray was massaging his mother's shoulders again on her bed, in the same manner he had done the previous weekend.

"This is a good way to start. Next pull my tank top up and start rubbing my belly." Julie instructed.

"Good, just like that. Perfect. Now slowly start inching your fingers down toward my shorts."

Ray did just that for several minutes, except he stopped with his fingers right at her shorts. Julie had been moaning softly and didn't immediately notice his pause and trembling hands.

"Mom, I don't know if I can. I mean I want to, I just, I don't know. I'm sorry."

"Oh sweetie, hey, it's ok," Julie said, sitting up and turning around to face him. She was holding his face, resting on her knees. She gave him several slow kisses on his mouth.

"I want to. I really do. I've never done that before." Ray sighed, hanging his head dejectedly. He was so very awkward around girls. Julie could really see his lack of experience shine through.

"How about we remove any sort of sexual expectations. I'm going to lie back against you like I was. I'm going to take your hand and put it in my shorts. I'll guide your finger to where it should go. Sound good?"

Ray nodded slowly and watched his mother resume her position. "Hand," she said holding out her own. She counted to three in her head, opened her shorts with her other hand and plunged his hand in them.

"Good, now, feel this? This is what you need to rub to get a girl excited. Alright? And then this area right below it, you can run your fingers through as well. Then here is where your fingers and your penis would go. Just like that." Julie said all in one swift motion. She guided his fingers to her clit, ran it through her outer lips, and then dipped his finger into her shaved pussy.

She released his hand, taking it out of her shorts. "There, simple as that!" Julie turned around, smiling at her son. She watched him nod and blush.

"Ok off to bed you go. I'm going to get me a late night snack," Julie winked, referring to the blow job she was about to give him, "and then you need to get some sleep. Two more days of school and then it's spring break and our trip!"

A few moments later, Julie wiped her mouth with the back of her hand. She leaned in and kissed her son on the forehead goodnight. "Goodnight sweetie. Oh and if you want to touch me there again tomorrow, you can. If not, it's no biggie. Takes awhile for courage to build up. If you want to touch me again, just ask, alright?" She explained with a friendly smile on her face.

"Ok mom, thanks," Ray said, rolling over to his side.

Chapter 12

"Yes! Right there, just like that, Ray!" Julie cried out, as her son plunged two fingers in and out of her pussy, while rubbing her clit with his middle two fingers of his other hand. Julie had shown him exactly what she liked and he was doing a splendid job for the last ten minutes.

She was sitting against him on her bed again. He humbly asked for permission to touch her again, Julie couldn't say no. She grabbed his hand and guided it into her shorts.

"Ok, wait! Stop!" Julie commanded, turning to face Ray, her head still resting back on his shoulder. "Ray I'm very close to having an orgasm. Are you ok with me doing that? If so your hand may get much wetter than it is now."

Ray nodded and within minutes she was shaking and moaning against her son. He held her in place and watched as a wave of pleasure coursed through his mother's body. He kissed her neck softly and then held her. For several minutes they sat there on the bed.

Ray kissed her neck once more, "Did I do ok?"

Julie, with her eyes still closed and her head resting against his shoulder, smiled and told him in a tired voice, "Ray you were great. You picked it up really easily. It felt wonderful."

"Ok, cool." Ray replied, smiling back at her.

The next evening consisted of more practice and another orgasm for each. Julie went first, then her son, via her mouth.

Saturday was their flight to the Bahamas, after a brief layover in Miami. The resort was an immaculate, newly renovated, vacation spot. It had its own staff and the rooms were basically villas - each having their own back courtyard with a bubbling hot tub.

"Oh wow, this is amazing, Ray!" Julie placed her bag on the bed, and checked out the bathroom. The shower was huge. Her first thought was that it could easily fit her and Ray in there.

"Look out here! Oh my..." Julie looked into the small courtyard, noticing the hot tub. Ray came up behind her, resting his hands on her stomach.

"Maybe later tonight, I can have some wine delivered, we can get in there, " Julie turned around and tickled her son, "and momma and you can have some fun!"

Julie went back to her bag, leaving Ray behind to blush. "I'm changing into my bikini and then we'll hit the beach."

A few moments later, Julie emerged from the bathroom wearing a brand new bikini courtesy of Bob. It was a tiny, pink with black polka dots, thong bikini. "Well do you like it?" She asked her son, laughing as his mouth dropped open. She approached him, grabbing his hands and placing them on her waist.

"Do you think it's sexy?" she asked. He nodded, glancing down at her cleavage.

"Do you think I'm sexy?"

"I do," Ray answered.

"Are we going to have a good time this week?"