The Challenge Ch. 01

Aunt Sharon gave Ray a long goodbye hug, then gave her sister an even longer embrace, whispering in her ear "Let me know what he says."

The next challenge Julie faced was telling her son.

Chapter 7

Three nights later Julie stood in front of her full-length mirror, this time in her white bath robe. "Well Ray? What do you think?" She asked her reflection, and then loosened the tie on her robe, letting it fall to the floor revealing her naked body.

"Do you want to? Do you want to have, uh, have sex with me?" She asked her son in her head.

"This is so stupid!" She said, kicking her robe out of her way and climbing on to her bed. She looked at the wall opposite of the bed, near the mounted TV. She stared at the camera hidden just below the TV. Bob was there the previous evening and the two of them tested the camera with his computer.

"Feel free to put on a little show for me if you like dear," Bob suggested. Julie rolled her eyes and saw him to the door.

Back in her bedroom, she rehearsed her lines over and over again. She ran through several scenarios in her mind. The one she settled on was waiting until Saturday night and telling him over dinner. She would then propose the idea to him and wait for his reaction. He would either laugh it off and tell her no thanks, or say "yes let's do it!" She practiced undressing for him in the mirror. It didn't feel right though, it didn't feel natural.

Julie sat up and hopped of her bed. She went to grab her shower friend from her top drawer and headed toward the bathroom door when her cell phone vibrated on the bed. She wondered who could be calling this late as she went to pick it up. She saw on the caller ID it was her friend Ulysses. He must be back in town.

"Hello?" she answered.

"Hi Julie, its Ulysses. Sorry to be calling so late."

"Oh it's ok, how are you? It's good to hear from you again."

"I'm good, just arrived back in town. I know it's been a few months, but I was thinking we could hang out soon and catch up."

"Yes! I'd love that!" Julie replied, tossing the dildo on the bed.

"Great. Can I take you to dinner Saturday night?"

"Saturday?"

"Yeah, I know it's short notice, but if you don't have plans we could go to dinner then back to my apartment if you like." Ulysses proposed.

Julie thought about Saturday, she had planned on telling Ray of the challenge, but this would give her a way out. She could put it off for a little while longer until she got more courage. She thought carefully for a few moments then gave Ulysses an answer.

"Yes! Yes!" Julie cried out, clutching Ulysses tightly, locking her feet around his muscular ass as he drove his cock deeply into her over and over again.

The two friends had been going at it for over an hour; Ulysses bringing Julie orgasm after orgasm. He kissed along her neck and rose up to look upon her gorgeous body. He ran his hands over her breasts and smiled at her. "You're beautiful," he said.

She nearly came again looking up at his sweaty, perfectly muscled body. "So are you!" she replied in between breaths.

"It's been a long day for me. Would you be ok if I finished a little earlier tonight?" Ulysses asked.

Julie smiled weakly, "Go right ahead."

"Hold on tight then," He said. Ulysses bent down to bring Julie up. She wrapped her arms around him, and locked her feet again. Ulysses was on his knees and began thrusting into her. He was grabbing her ass cheeks and slamming his thick rod into her stretched out pussy. Over and over again for several minutes he thrust up into her, touching bottom each time.

Julie arched her back, and threw her head back. Ulysses brought a tit to his mouth and suckled on it as another orgasm coursed through Julie's body. He wasn't far behind. Releasing the nipple, he gritted his teeth and picked up the pace. Julie unwrapped her arms around his neck and held them out to her side, perpendicular to her body. Her eyes rolled in the back of her head; she was in paradise.

"Ah Julie, yes!" Ulysses cried out, as his own orgasm over took him. He thrust several more times into her while his cock injected semen into her womb. Out of breath, he slowly lowered her back to the bed as his cock spurted a few more times, his cum overflowing out of her onto his mattress.

"Thank you," he whispered in her ear, sluggishly rolling off her, resting next to her on the bed. Julie smiled and came out of her trance. She rolled over, placing her hand on Ulysses' six pack stomach.

"Ulysses?" Julie spoke up 10 minutes later.

"Yes?" He replied.

"Do you think I'm a bad person?"

"What? Of course not. I would never be friends with a bad person. Why do you ask?"

"Well, to be honest, I have been offered a lot of money to do something that I'm not sure I can do." Julie explained.

"Well does it involve hurting someone?"

"Not really, I don't suppose. I've been offered a lot of money to have sex with a certain person."

"Whoa, I see. Is this person of legal age?"

"Yep."

"Are they someone you know and care about?"

"Yep."

"Would you be having sex with them or would it be more like making love?"

Julie paused and thought for a moment, thinking about Ray's sweet smile. "Love." She replied sheepishly.

"Well then, I say do it. No one is getting hurt and you'd be doing something beautiful and getting paid for it. The person offering you this money to do this has their reasons I guess, but I'd say do it. Make love to this person, make it beautiful, and graciously accept the money."

Julie smiled. Ulysses was right. She was going to tell Ray about this and work toward doing it. Valentine's Day was coming up next week. She decided to tell Ray then.

Chapter 8

Julie left a note for Ray that she wanted to speak to him about something when she got home from her shift. All day she rehearsed what how she was going to tell her son. That Valentine's Day evening she got home around 10:30pm as usual. She headed to her bedroom, undressed and put on her white bathrobe. Knowing her own child as well as she did, she knew nothing would happen that night. However, she wanted to be prepared for any unpredictable outcomes of their conversation. She told herself if that meant Ray would become enthusiastic about this challenge and excitedly ravaged her, then she wanted be able to have as little clothing as possible in order to make this go by quickly. Perhaps Ray would want to see her naked, in which case, she would simply stand and disrobe for him. Her instincts were telling her none of that would happen that night.

Julie slowly crept down the dimly lit hallway to Ray's closed door. She looked down to her robe and loosened the tie slightly and made sure just enough cleavage was showing.

Softly knocking on the door, Julie asked just above a whisper, "Ray? May I come in?"

There was a pause. "Hey mom, sure."

Julie entered the room, sitting on the bed, as Ray say up, rubbing his eyes. "Did I wake you?"

"No, I was dozing off but not completely asleep." Ray replied.

"I see." Julie said, looking around his room, occasionally looking down and playing with her long fingernails.

"So what did you want to talk about?" Ray asked.

There was a long pause as Julie gathered her thoughts. "Ok. Well, I have to tell you something that's a little strange and I want you to remain calm. I will explain something and then present you with a question. If you say no, that is totally fine. Alright?"

"Alright, no problem. Is everything ok?"

Julie didn't answer. Instead she tried to recall her memorized lines. "You know my friend Bob. You met him last year, and you saw him last week when he stopped by. Well he's an interesting man. I think I've mentioned to you that he's pretty wealthy and has bought me presents from time to time."

"Mmhmm, that nice dress, right?"

"Very good! Another compliment from you on my dress." Julie smiled at Ray, and then continued her dialog.

"Well as you can see Bob is an older guy, I'm not sure he has much time left. Or perhaps he thinks he doesn't. He has set aside a lot of money to give away to charities and maybe some family he has left. But he's also doing something else with his money. He is issuing challenges to some of his close friends. If they meet these challenges he said he would give them a certain amount of money."

Ray nodded, paying close attention and putting two and two together. "So he's going to give you money?" He asked with a smile on his face.

"Well I'm not sure. He offered me a challenge. He offered me a large sum of money to do something that, truthfully, I'm not sure I should do. To be honest, the challenge involves you as well Ray."

"It does? What does it have to do with me?"

Julie paused again. The conversation wasn't going quite as she imagined, but she adapted and continued. "It has something to do with both you and me sweetie."

"Uh, ok, well what's the challenge?"

Julie took a deep breath then placed her hand gently on her son's. She paused again, caressing his hand with her thumb. She looked up into his eyes.

"He wants you and I to have sex."

Ray's eyes widened and he withdrew his hand from his mother's, he backed away from her on his bed, looking as though he had just seen a ghost.

"What?!?" Ray cried.

Julie held up her hands. "Please just relax, calm down."

"You mean you and me, doing it?" Ray asked, with a look of terror on his face and his voice shaking.

"Ray, calm down and listen to me. Calm down." Julie said.

Ray was nearly out of breath, sitting on the edge of his bed, looking to the floor.

"You can say no. Alright? It's fine, really it is. There is no deadline for this. If it happens, it happens, if it doesn't, it doesn't. It's as simple as that. There is a camera in my room that I can control that would capture it if it does happen. Bob would need proof. Ok?"

Ray sat there looking down to the floor, rubbing his temples. After a few moments he spoke up. "I don't know what to say."

Julie smirked to herself. That was the third time she's heard someone say that; first herself, then her sister, and now Ray.

"Ray, It's ok. This isn't something we must do or else. If you don't want to, we don't have to do it at all."

Ray sighed and shook his head. "How much did this guy say he'd give you."

Julie cleared her throat, "Well if you must know it's enough money to pay for all your education and for us to live comfortably. Probably for the rest of our lives."

Ray turned and looked toward the wall behind his bed, facing away from Julie. "Please. How much?"

Julie paused, "Twenty million dollars." She watched Ray inhale deeply and resume his position of looking down to the floor.

"It's just I've never done anything before. You know, with a girl. I, I," he sighed, "we could use that money though."

"I know we could. But we'd be fine without it sweetie."

Ray's voice lowered to just above a whisper, "You've worked so hard. All those long shifts and overtime. Ever since what's-his-face left us." Ray said, referring to his father.

"I know, I know, " Julie replied, her voice trembling as she placed a hand on her son's shoulder. Ray flinched at her touched, but then settled.

Ray shrugged, "I mean, I guess we'd be stupid not to. I just don't know."

Julie gently massaged his shoulder with his hand. "Look I'm going to bed; I want you to do the same. Ok? Sleep on this. If you can. You don't have to give an answer tonight or tomorrow. If your answer is no, then that's fine with me. If it's yes, then we can think about how to go about handling this. Alright?"

Ray nodded, still unable to look at his mother. Julie rose on her knees and kissed the side of his head. "Remember, I love you more than anything. We'll talk more about this later. Try to get some sleep."

Chapter 9

Julie felt like an immense weight had been lifted. She slept soundly for the first time in a long time. She was a little concerned that Ray was freaked out by this, but felt relief in being honest with him and letting him decide if they should pursue this challenge.

That evening Julie got home at her usual time. She undressed and put on her white robe again, in the event she needed to turn her camera on and undress quickly for a brief intercourse session with Ray. The more she thought about sex with him, the less it seemed like a business transaction and more about giving herself to him - for money yes, but also as a teacher.

"Come in." Ray answered the small knock on his door. Julie entered his room as Ray averted his eyes and pretended to straighten up his bedside table.

"Hi. May I sit?" Julie asked.

"Sure."

Julie sat on his bed, smiling softly at her son, who was still busying himself by cleaning his table. She looked down and adjusted her cleavage again, this time showing just a little more than the night before. "Just wanted to stop by and say goodnight."

"Oh ok, cool."

"Thought anymore about last night?"

Ray went still, no longer shuffling papers and trash around. He slowly sat on his bed, and resumed the same position from the previous night. He was looking down to the floor. He slowly nodded his head.

"Yeah? So what's on your mind?" Julie asked nonchalantly.

"Well," Ray said, slowly turning in his bed to face his mother, "that's a lot of money. You've sacrificed so much for me."

"Ray - " Julie started to interrupt.

"No, just hang on. I think, I think we should possibly consider that challenge."

"Yeah?" Julie smiled and straightened herself up on the bed.

Ray nodded and slowly looked up her eyes, his face fraught with fear. Julie almost laughed, but only smiled back at him. She reached out and took his hand.

"Ok, well we can talk more about it tomorrow night. I don't have work Saturday. We can brainstorm some ideas of how to go about it. I mean, I'm sure you know how to do it; I just meant how we can handle it. Deal?" She asked, squeezing his hand.

"That'll work."

Julie, releasing his hand, caressed his face. "It'll be ok, we'll work this out. Alright? No need to be nervous. Come here, give me a hug."

Julie stood, extending her arms to Ray. "Oops." She noticed her robe was almost completely open in the front, nearly exposing her breasts. She adjusted herself and held out her arms again. "There, that's better."

Ray nodded and smiled weakly, bending down to hug her. Julie closed her eyes and rested her head on his chest. Ray slowly moved his hands to her waist. He usually wrapped his arms around her shoulders. Gently placing them there he pulled her in tighter against his body. She couldn't help by smile; her body was warming against his, just as her mind and heart were warming up to this idea of making love to him.

Julie ended the embrace, smiling up at her son, "We'll get through this. Don't be scared, we'll work it out!" She said, caressing his cheek. She rose to her tip toes and kissed him quickly on the lips before making her exit.

"Goodnight. Love you," she said, and then headed down the hallway. She began untying her robe as she walked to her bedroom. Tossing it on dirty clothes hamper, Julie stood nude in front of her full length mirror, examining her body and chatting on the phone with her sister, Sharon.

"Don't worry Sharon. I know what I'm doing. Please trust me. He's open to the idea; I think this will all work out for the best." She ended the call to her sister and climbed into bed. She fell asleep with images of her nude body rolling around on a pile of money.

"May I?" Julie asked Ray the next evening. He was sitting on the couch in the living room playing his hand held gaming device.

"Huh?" Ray asked, looking up at his mother. She wore a spaghetti-strap white tank top, with no bra, and pink short shorts, with no underwear.

She smiled looking down at him, "Sit?"

"Sure."

"Thank you." Julie said, plopping down on Ray's lap. "Now then, let's turn this off and set it down," referring to his gaming device, "and let's chat about our situation. What are you most comfortable with? What are your thoughts on how to proceed?"

Ray looked down to his hands resting on his stomach. He glanced at his mother's nearly bare thigh on his lap. "Uh, well, I mean - " Ray started to say before Julie interrupted him.

"Ray wait. Let's do something with your hands. You have a woman sitting on your lap. Here, take this hand and put it here on my thigh, and bring the other one back around me and rest it on my lower back. See?" Julie smiled down at her son after placing his hands on her. "Now, where were we?"

Ray cleared his throat nervously. "I guess we could try going on a date again or something." He hand was trembling on Julie's thigh.

"That's a great idea! A good start too." Her smile quickly went to a frown. "Oh Ray, you're shaking. Relax." She held his hand still on her leg. "See, it's just me. You have to get used to touching me more. I figured that'd be a good start too. Don't you think?"

Ray nodded and watched his mother move his hand slowly up and down her thigh.

"Just like that. See? It's soft isn't it?" Julie asked.

"Yeah."

"I'd love to buy you a new car. I'd buy myself one too." Julie said looking off in the distance as she moved his hand on her thigh. "Maybe sell this house, buy a new one. Gosh, we could even move to another city or state if you wanted."

Julie released Ray's hand and kept talking. She didn't notice that Ray kept moving his hand up and down her thigh, gently squeezing it.

"Ooh, maybe we can go on a vacation after all this. You know?" Julie asked. She looked down at Ray whose eyes were focused on her thigh. He was rubbing and squeezing it. Julie smiled and watched him. She doubted he had ever touched a woman's leg before. Julie looked up to the ceiling trying to think of a way to push this further and not freak him out.

"That feels good baby," She whispered in a slightly sultry tone.

"Huh? Oh, sorry." Ray released her thigh, putting his hand back on his stomach.

"No, don't stop," Julie said, reaching down to guide his hand back to her thigh. This time she slid it further toward her shorts and hip.

She leaned down and whispered again in ear. "You know maybe for spring break next month we can go on a trip. Bob said he'd pay for anything to help us do this. Does that sound nice?" Julie asked in a sweet tone.

Ray simply nodded. "We could go to the Bahamas. Just you and me." Julie said. Ray only nodded again, looking at his hand on her thigh.

They sat in silence for several more minutes before Julie spoke up. "So, a date tomorrow night?" She asked sitting up.

"Yeah, maybe dinner."

"Great! I look forward to it!" Julie exclaimed, rising off her son's lap. "I'm heading to bed. Feel free to come hang out if you like." She winked before walking off. As she climbed the stairs to her room, she began peeling her clothes off. She would be ready for him should he decide to show up. He never did.

The next day was fairly normal between them, besides Julie giving more hugs and more pecks on the lips than usual. That evening they went to a nice restaurant. Ray complemented her dress and shoes without being reminded this time. Overall he seemed a bit more natural on this particular date.

About halfway through dinner, Julie reached out and grabbed his hand. She caressed it with her thumb. Ray glanced from her hand to her eyes. She was smiling softly at him. They gazed into each other's eyes for several seconds before Ray blinked, shaking himself out of the trance.

"I'm sorry. This just feels, I don't know, weird still." He said, looking down to his food.

"Ray, it's ok. I know. Let's just slow down a bit then shall we? Let's relax."

Ray nodded and they finished their meal. The rest of the date was fine. He escorted her to the car, and then from the car to their house. He even escorted her to her bedroom door. He gave her a hug goodnight.