The Challenge Ch. 01

"So is that how you treat your date? 'Here' then hand her her coat? Geez, you might as well just toss it to me." Julie rolled her eyes, teasing her son.

"Oh, alright, well - "

"No! I didn't mean actually toss it to me. Hold it open and put it around my shoulders." Julie explained.

"Sorry. Here you go."

"Thanks. Now walk me to the car, open my door for me, you should know all this."

"Well I didn't know this was a date." Ray said.

"Yeah well, it is, so always be prepared." Julie teased, making things up as she went along, she figured she would treat this as a practice date. This way she might be able to see what romance with him would be like.

Dinner was awkward but not a total catastrophe. Julie constantly had to offer her son pointers and reprimand him when he started reverting into a non-date mode. He would slouch, she would tell him to sit up straight. He would look around room and not pay attention to her when she was talking; she had to snap him out of that. He would play with his food; Julie had to remind him not to. She actually had fun spending time with him, and was genuinely entertained by his lack of dating experience - even if she felt she could've been around more to help with these sorts of things. He was terribly awkward and shy around girls. Julie saw a lot of herself in him when she was a teenager. They had virtually identical looking mouths - the same overbite and smile. His eyes were green, not blue like hers. His hair was blond, like Julie's. He was also as skinny as a rail. This reminded Julie of herself as a teen. She was a petite, small, little thing.

"Where are you going?" Julie asked Ray at the top of the stairs back at home.

"I'm going to change and go to bed."

"Oh no, no, no. I'm not done with you."

"What do you mean?" Ray asked.

"Our date isn't over. Come to bed." Julie replied, with a mischievous smile.

"Mom. Really? Come on, I want play that game you got me for Christmas."

"You can tomorrow. But we're not done here tonight. I don't have work tomorrow, remember?"

"Ugh, fine." Ray sighed and walked toward his mother's room.

"Don't sound so happy about it! Do you think your date likes that tone?"

"No, I guess not."

"Good, now get on the bed!" Julie playfully pushed Ray onto her king sized mattress. He sighed and threw his long legs up on the bed. He was 6'1" and seemed to be nearly all leg. Thin, tall, and lanky best described him. Julie smiled and slowly undid his shoes and slid them off his feet. She tickled the bottom of his feet.

"Hey, cut it out."

Julie chuckled and climbed up on the bed next to him. "Put your arm around me."

"Mom, why?" Ray sighed, holding out his arm.

"Stop complaining and just go along with it. I miss spending time with you."

"Alright, fine."

Julie snuggled up next to Ray, resting her head on his chest and ran her fingers up and down his stomach. "You didn't even compliment my dress, Ray."

"Oh, uh, sorry. It's a nice dress." Ray said flatly.

"Wow, I feel so special," Julie replied, sarcastically. She glanced down to his crotch and a generic image of a penis shot through her head. She imagined unzipping his pants and pulling it out to slowly stroke it. She sighed again, not having any idea of how to initiate that with him.

"Are you looking forward to going to college in the fall? I bet you are. It'll be nice to get away from your old mom." Julie asked.

"Nah, you aren't old. I was actually thinking about attending one of the schools closer to home. There's one that is pretty cheap. That'll make things easier for us." Ray explained.

Julie rose up on her elbow, "Oh Ray, no, I want you to go where you want to go. Don't worry about costs."

"It's fine mom, really it is. I like that school. Being cheaper is even better."

Julie slowly looked down to his chest and straightened out his red tie. She almost started crying thinking about, what could be, a huge sacrifice Ray was willing to make. She slowly laid her head back down on his chest.

"Ray, you can go play your game if you want." She said, slowly rubbing his stomach over his shirt.

"Cool, thanks mom," Ray said, starting to sit up. Julie rose with him. Ray put his arm around her, giving her a brief hug before going to his room.

Julie had trouble falling asleep. Bob's twenty million dollars and all she could do for Ray was all she thought about.

Chapter 4

"Are you a virgin?" Julie asked her son, watching his eye widen.

"What!?" He asked. They were lying on his bed, snuggling the next night. Julie entered his room earlier and said she wanted to spend more time with him before work. Ray kept playing his video game, after telling her to come in and have a seat.

"No, I mean turn the game off now, and come spend time with me. Tomorrow I go back to work and you go back to school."

"Alright," He said, turning the game off.

"On the bed." Julie ordered. She snuggled up in his arms just like the previous night and they chatted for awhile. He was in his t-shirt and pajama pants, and she was wearing a white tank top and similar styled pants.

"You heard me, are you a virgin?" Julie asked again.

"Uh well, I uh..."

"Listen," Julie rose up on her elbow looking into his terrified eyes, "you don't have to be nervous or ashamed to tell me something. It's really ok."

Ray gulped and nodded slowly.

"So does that mean yes?" Julie asked. Ray nodded again.

"Ok well that's fine, that's totally fine sweetie," She said patting his chest. "I was just curious."

Julie smiled, resting her head back on his chest. She glanced toward his crotch again and slowly moved her hand down to the edge of his shirt. She slid her hand underneath and ran her long finger nails along his bare skin, looking to his crotch for any sort of indication he enjoyed it. She saw none.

"You know you can ask me anything; anything about that sort of stuff," Julie said, running her finger nails up and down his stomach. "I know we haven't talked about," she paused, "sex much, but I am here for you if you have questions. Alright?"

"Ok," Ray quickly replied.

Julie could tell his breathing pattern was changing a bit. "Does this tickle?"

"A little, yeah."

Julie chuckled and kept trailing his stomach with her finger nails. "So no questions for me?"

"Nope, I'm good."

"Did you know I was 21 when I did it for the first time?" Julie said.

"Mom! Too much info...geez..."

"Oh relax, I'm just saying, sometimes it takes awhile for things to happen. But they do."

Julie lost her virginity to Ray's father. She was still in an awkward phase, still scrawny, and nerdy looking. Over time that changed. Ray's father leaving when she was in her mid thirties helped to speed along her transformation into a sexy, confident, woman.

Ray quickly changed the subject much to Julie's chagrin. They spent the rest of the evening in his room, talking, laughing, mixed with Julie's playful teasing and tickling. She figured she was planting a seed of sorts. She dreaded going back to work tomorrow but was looking forward to next weekend.

"Alright, well I better head to bed. I need my sleep for a long shift tomorrow." Julie said.

"Ok mom. Thanks."

"For what?"

"For everything I guess. All the long shifts you work and your dedication to taking care of us." Ray said.

Julie tried to hold back tears as she hugged Ray. She ended the hug with a quick, but strong, kiss on the lips - something she hadn't done with him in many years. "I love you," she whispered, then ended the embrace.

Another restless night of sleep followed for Julie. She tossed and turned, thinking about Ray, about work, about money. She wanted to ask her younger sister, Sharon, for advice. She would see her next weekend.

Chapter 5

Each night of the following week Julie made it a point to see Ray before she went to bed. She usually got home after dinner and Ray was either in the bed already or getting ready to be. If he was already asleep she would wake him up and talk with him. She would end each evening with a quick kiss on the lips. On Wednesday he was out cold, having gone to bed earlier than normally. She quiet slid into his bed and snuggled up to his back. She felt like being playful and squeezed his butt, causing him to stir.

"Hey, what are you doing?" Ray groggily asked.

"Nothing, just playing. Have you ever had your butt grabbed before?"

"Huh! No."

"You have a nice one."

"Alright, thanks. I'm going back to sleep now." Ray sighed.

"Have you ever grabbed a girl's butt before?" Julie asked.

"No, I haven't. Ok? Goodnight."

Julie felt extra brave this evening and wanted to test the waters, "You can grab mine if you like. If you want to see what it's like"

"Mom! Ok, geez! Can I go back to sleep now?"

"Fine! Remember your Aunt Sharon is staying with us this weekend. Her and I will probably go out to dinner or something. You are more than welcome to join us."

"Ok, goodnight."

Julie slapped his butt again and kissed the back of his neck, causing him to jump. She smirked and headed back to her bedroom, undressing out of her scrubs as she walked down the hallway. She didn't close her bedroom or bathroom doors anymore, thinking that if he wanted to peep in on her, she would simply let it happen - maybe even encourage it. To her knowledge, Ray never sneaked around and attempted such a thing.

Julie rummaged through her top draw and found her favorite shower companion; an 8.5 inch, black dildo with a suction cup at the end - perfect for hands free fun. Holly got it for her birthday a couple years ago. She smiled at her rubbery friend as she stuck it to the glass shower wall.

As the steam from the water rose, Julie turned around and looked at the dildo. She smiled, glancing to her open bathroom door.

"Hey there. It's been awhile hasn't it?" She asked the inanimate object. "We're going to have to keep it quiet; I wouldn't want to wake my son."

Julie went down to her knees in the shower and slowly stroked dildo. "Besides if he saw mommy doing this, he might like what he saw." She kisses the tip and then playfully licked underneath it.

Julie was ready to put on a show. If her son saw it so be it. "And that would be very naughty wouldn't it?" She winked up at an imaginary man, and then engulfed the cockhead. "Mmmm, mmmm," she moaned as her head weaved back and forth and side to side on the dildo.

"Such a nice dick you have here sir." She said standing and stroking the cock before turning around. She slowly swayed her hips back and forth across the dildo.

"You ready for me?" Julie asked, looking back to the wall. "Good," she said, reaching behind her, guiding the dildo into her dripping pussy. She pushed back against it all the way, until her ass cheeks were pressing against the glass. She arched her back, placing one hand on the wall in front of her, while the fingers of her other hand furiously rubbed her clit. She began moving back and forth on the dildo, moaning softly as she did, her cheeks pressing against the glass.

"Are you watching me?" She asked out loud. "You can if you want." She grunted as she started slamming into the mounted dildo. "Ah yes..."

Julie imagined Ray peeping around the open bathroom door, seeing her slam into the dildo, her cheeks slapping against the glass wall. She felt so naughty, so horny, and so motivated to make this happen - to win that money.

"We're going to win it baby, it'll be ours, we can do this! Yes! Yes!" She cried out a little louder this time. If Ray was asleep, that might have woken him. She kept going, pounding into the glass, imagining money raining from the ceiling, covering her bed.

"Cumming! For that money!" Julie's orgasm over took her and she picture both her and Ray writhing in ecstasy on a money-covered bed.

Ten minutes later, Julie stood naked in front of Ray's closed door. She saw no sign that he had been watching her. She slowly opened it and peeped in. He was asleep in the same position she had left him. She felt like an idiot.

Julie sat at the edge of her bed, staring down to her knees. She was looking forward to Sharon's visit tomorrow. She wanted to ask her opinion on the matter. Sharon was the logical, analytical type. Her opinion would be helpful. Holly, on the other hand, would tell Julie to do it and not even consider the consequences and changes to the mother/son relationship that could occur. Holly would probably even ask for some of the money too. "Come on we're sisters! Just a few million is all." Julie imagined Holly saying. Julie climbed into bed. "A penis is a penis," she whispered to herself. "I have to do this."

Chapter 6

Julie cleared her throat as she stood in front of her son while he sat on the couch, busily playing a hand held gaming device. She was wearing a short, tight, blue cocktail dress with matching blue shoes - all courtesy of Bob.

"Oh, uh, your dress. It's very nice." Ray said, before sticking his nose back into his game.

"Well at least that's something. It's nice to compliment the shoes as well."

"Those are nice too," He said, barely even glancing at them.

Julie couldn't help by chuckle. "Walk us to the door."

"Huh? What do you mean?" Ray asked.

"I mean, get up, and walk us to the door. If I were your woman, going for a night out on the town, I'd want you to do that."

"He's a slow learner Julie." Ray's Aunt Sharon called out from the kitchen. She was wearing a similar but black dress. She was 5'9", had blue eyes just like Julie. Julie felt her younger, 37 year-old, sister was the most attractive of the three siblings. Her eyes were sparkling blue, she did not have an overbite, and her face had a sophisticated beauty to it. Her hair was platinum blonde, but much shorter than Julie's. It was in a bob-style and came just past her ears. She didn't have bangs, which added to her elegance.

"I know, but I'm teaching him," Julie wrapped her arm around Ray's as he led them to the door. "Please don't wait up. Leftovers from last night are in the fridge. Alright?"

"Yep. Have fun." He said, remembering to help his mother with her coat.

Julie rose up and kissed his lips, "Goodnight, honey," she playfully said before jabbing him in the ribs.

"Yes, goodnight, honey," Sharon said in the same teasing fashion before kissing his cheek.

"When did you start smoking again?" Julie asked, waving the smoke away from her face.

"Oh, I don't. I mean, sort of. I only smoke like 3 cigarettes a month. Only when I'm out with friends." Sharon explained as the two women sat at a table in nearby nightclub.

"Hmm, well alright," Julie said, shaking her head.

"So do I get to meet him?" Sharon asked.

"Meet who?"

"The guy you're seeing?"

Julie immediately thought about Bob and his challenge.

"Did you say you were hanging out with a fitness model?"

"Oh! You mean Ulysses? Yes sometimes, I think he's out of town this week. We're not really dating each other, just occasionally hanging out." Julie explained.

"How are things with your fellow?" Julie asked her sister.

"Ugh, I don't want to talk about it. Dating a younger guy has its advantages, but he's so possessive!"

"What does Sam think of him?" Julie asked, referring to her nephew, Sharon's college freshman son.

"Doesn't like him one bit, to be honest. Anyway, let's dance," Sharon said, standing and extending her hand to her older sister.

Three hours later, the lovely siblings arrived home, laughing and stumbling their way the kitchen. Julie was the designated driver, so she immediately went to the kitchen for wine to help her catch up to Sharon.

"Couch?" Julie asked, sipping her wine.

"No, let's go to bed, I need to lie down." Sharon replied, motioning Julie to follow.

"Unzip me?" Julie asked, setting her wine on the bedside table. Sharon complied and assisted her sister.

"Wow! Look at those!" Sharon's eyes widened when her sister turned around revealing her implants.

"Like them?" Julie asked.

"I love them! May I?" Sharon asked, holding her hands out.

"Of course." Julie said, arching her back so her sister could inspect her implants.

"I totally forgot you got these, until I saw them in that dress you had on. These feel amazing!" Sharon said, gently squeezing Julie's breasts. "Is there sensation in the nipples? I heard that can be decreased with implants."

"A little yes, but mine seem to work ok."

"Really?" Sharon asked, with a mischievous look on her face. She squeezed a breast once more and then circled a nipple with her thumb.

"Hey, stop that!" Julie squirmed and moved away. "Turn around, let me unzip you."

Later in the evening, the two women lay in bed facing each other. Julie was wearing one of Ray's t-shirts and a thong. Sharon was a smaller t-shirt and boxers.

"So when he left the hospital he sent me flowers and included his number. Figuring, why not do what Holly would do, I called him. He took me to dinner, we slept together, and when he's back from visiting his fiancé in Jacksonville, we meet up on occasion." Julie explained about her relationship with Bob.

"How is the sex?"

"Not bad at all actually. He doesn't do much, I do most of the work, but it's quite enjoyable. I don't always have an orgasm, but it's still fun."

"Good. I guess. I mean, I think it's a bit shady to continue seeing him when he's set to get married soon. Plus he's buying you all this stuff." Sharon said.

"Well actually there's quite a dilemma now," Julie said, sitting up on the bed, looking down to her sister.

"Yeah what is it?"

Julie shook her head, "He's giving away his money; to charities, to his fiancé, and so on. Well he offered me a large sum of money. I won't go into specifics, but it's more than enough to pay for Ray's entire college tuition."

"Wow, that's really nice of him!" Sharon said, rising up on her elbow.

"Well not so fast. I can only have the money if I have sex with a particular person."

"Hmm, ok. Who?"

"Ray."

Sharon's mouth dropped as she looked on in shock. "Ray? You mean, him?" She asked, pointing in the direction of Ray's bedroom.

Julie nodded her head. "I haven't done anything yet. I thought about it, and tried imagining it, but it's really difficult. This challenge can only be completed when he installs a camera in the bedroom AND I turn that camera on to capture, well, the act. If we never do it, then we never do it, and we don't get the money."

Sharon took a deep breath and slowly looked around the room. "I don't know what to say."

"I know. I didn't either. I would rather have your input than Holly's. She would say I should and ask for some of the money probably."

"Yeah she would. Wow." Sharon cupped her mouth with her hand, thinking of the situation.

"Should I? Ray and I would be set with the money I'd get."

There was a long pause before Sharon spoke. "You should tell Ray. Tell him about this and see what he thinks."

"What if he's not interested?" Julie asked.

"Well then I guess you don't get the money. But I'm wondering what if he IS interested? Are you willing to commit that act with him?"

"I've thought about that. I think I could, I mean, maybe. We could be blindfolded and pretend we are different people."

"Right. Well all I can suggest is telling Ray about this and see what happens. That's my final thought on it."

Julie nodded and curled up next to her sister. The two eventually went to sleep.

The next morning, Julie overheard Sharon talking with Ray on the couch in the living room. "You know your mom loves you more than anything and is working really hard to support you."

"Yeah I know. I'm really proud of her," Julie overheard Ray say before entering room.

"She would do anything to help you and to provide a good life for you, you know that right?" Sharon asked.

"Mmhmm, she's great." He replied.

Julie again, had to fight tears and compose herself before entering the room. "Ok, you got everything packed Sharon?"