The Challenge Ch. 01

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Author’s Note: I’m not sure if the amount of money offered in this story is realistic. I made a post in the forums asking about it, but got no responses. I left the amount as is. As is the case with most of my stories, there is a small amount of interracial themes, along with older man/younger woman in this story as well. Feel free to leave comments at the end.

Editing thanks go to Todger65!


Chapter 1

Julie smirked, chuckling to herself as she felt Bob’s still-working 70 year old penis twitch and spurt semen inside her. Her hands were resting on his large, round, belly as she watched him moan and convulse below her. Reaching upward, he cupped her fabulous new triple D sized, teardrop-shaped implants he had given her a few months ago for her 41st birthday.

“Good?” She asked, raising an eyebrow while rubbing her hands on his belly.

“Oh yes. Very good.” Bob groaned, releasing her breasts, propping himself up on his elbows.

Julie smiled, leaning forward, dangling her breasts in front of his open mouth. Bob flicked his tongue across a nipple, and then placed several kisses across the bulbous breast meat. She swayed her shoulders back and forth, playfully dragging her breasts across his white, Santa Claus-like beard. She giggled to herself at the tickling sensation before sliding off Bob and resting next to him on the bed.

“Sorry I didn’t last that long Julie.” Bob apologized.

“Aww, don’t worry about it. It’s no big deal,” She said, throwing her arm around his chest, sighing contently as she felt semen ooze out of her. She loved that feeling. She loved having sex with him. While not as energetic as other partners, he was always funny, and made her feel comfortable. They have been sleeping together occasionally for about 6 months – shortly after she took care of Bob during a quick visit to the hospital where she was employed as a nurse. She couldn’t resist his charm. He was much older than any man she’s had sex with, but the single mother didn’t care.

“Well I do worry about it. I guess I should be glad the thing works, but still, a lovely woman like you should be getting yours during sex.”

“I’m telling you, it’s ok. I had a nice orgasm earlier when you went down on me. It’s that beard!” Julie teased, running her fingers through it.

“Well, alright, I guess I don’t feel as bad then.”

Julie smiled, continuing to run her fingers through his beard, “So have you and Robin set a date yet for the wedding?” She asked, referring to Bob’s 62 year old fiancé, who lived in Jacksonville, Florida.

“Not yet, but It’ll be this year sometime. We need to figure out if we’re having it in Florida or here in Atlanta. I suspect it’ll be Florida since most of her family is there. She’ll then move in here with me. So sadly, our little trysts will either have to come to an end or be few and far between!”

Julie nodded, “Well that’s certainly understandable. I wouldn’t want you to get in trouble. She’d divorce you and take all your money!”

“Oh no, we can’t let that happen,” Bob replied, reaching down to spank Julie a couple times. “That’s actually something I wanted to talk to you about.”

“Oh, want to give me a nice chunk of it?” Julie teased.

“Yes, I do actually.” Bob answered without hesitation.

Julie rose on her elbow, looking into Bob’s eyes, “Really? You’re serious?”

“Yes, I am, on one condition. I’ve already set most of it aside to donate to charities, and a nice amount for Robin, should I pass away first.” Bob explained.

“So what’s the condition, what are you talking about?”

“Well, I figured I’d have a little fun with people. I’d like to see what they are willing to do for several million dollars.”

“Hmm, alright. So where do I fit in with this?”

“As you know I’m a pervert. I love sex, and every kind of sex. I love having sex with you, Julie, so I figured why not challenge you in a sexual way?” Bob asked.

“Well this sounds like fun already! What did you have in mind?”

“You love your son, Julie? Would you do anything for him?”

“Well, yes of course, but what are you talking about?” Julie asked, her eyebrows narrowing, not entirely sure what Bob was hinting at.

“If I offered you enough money so you and your son would live comfortably for the rest of your lives, on the condition you accept and successfully passed the challenge. Would you do it?”

Julie paused, the concerned look on her face not leaving. She thought about all different scenarios in her mind. Anal? They had done that. Did Bob want some sort of threeway with her and someone? She didn’t see how a threeway would be worth millions of dollars. Suddenly her eyes shot open. Thoughts of urine, feces, animals, entered her mind. Certainly Bob would never challenge her to do that. But she wasn’t sure, maybe he would. She thought about her 18 year old son, Ray, and how hard she worked as a nurse to provide for him – many long hours, many exhausting shifts, in order to save up bahis firmaları for his college tuition in the fall. A million dollars, or even half that, would be a huge relief for them.

Julie sat up in Bob’s bed and continued thinking. She asked herself if she would do nasty things involving bodily waste for millions of dollars. She tried to figure out why Bob would want her to do those sorts of things. She then thought of her son again. They could get a new, nicer house, a new car for each of them, and tuition would be paid for through a bachelor’s, master’s, and doctorate degree – should Ray decide to go that far with his education.

“Yes! I would drink urine for sure I guess. It’s a sterile fluid anyway. Shit on the other hand…ugh…I could give myself an injection of antibiotics after I eat it, or just go the emergency room afterward to get checked out. This is so gross…” She thought to herself, before turning around to face Bob.

Julie sighed, “Yes, I would do it. Whatever sexual challenge you give me, I would do it. If you were to give me enough money to support Ray, yes I would do it.” She flinched as she imaged someone taking a shit on her, and then shuddered to shake the thought from her head.

“Good. Because I want you to make love to him.” Bob replied.

Julie paused, blinking a few times. “Who? My son?” She asked, as relief started to fill her thoughts and her heart rate settled.

“Yes, your son. I will give you, say, 20 million dollars if you make love to your son for me. I would set up a camera in your bedroom and the video feed would go directly to me and only me.”

Julie closed her eyes and exhaled deeply. She opened them and stared at Bob. A weak smile came across her face. “I thought you were going to ask me to eat shit or something.”

“Ha! Oh goodness no, my dear! Never! I’m a pervert but not that perverted.” Bob laughed.

Julie chuckled softly. “Why my son? Why would you want me to do that?”

“Truthfully I’m not sure. Perhaps a psychologist would need to figure that out and give you an answer. Maybe if you were my mother, I’d make love to you. Maybe your son came across as awkward and shy to me when I met him last year and perhaps I feel he needs a woman to show him a thing or two. Maybe I wished I had an older woman in my younger years to teach and guide me. It could be any of those reasons and more.”

Julie sat in silence, slowly turning around, facing away from Bob to look out his bedroom window, “I don’t know what to say,” she whispered.

“I’d say that 20 million is more than enough to support you and him for the rest of your lives, granted you are responsible with it,” Bob paused, nudging her ribs, causing her to jump out of her trance. “You could live comfortably, and not blow it on houses, cars, boats, or whatever. He would have to get a job after college, and not live off that money. If you do all these things I’m sure he’ll have some left to pass on to his children one day.”

Julie slowly nodded in agreement. “So you’d install a camera in my room?”

“Yes. One that you can turn on when you see fit. The video feed would go directly to my personal laptop, sort of like a webcam, but in your bedroom.” Bob explained.

“Am I the only one you are giving these challenges to?”

“Oh I don’t know dear,” Bob said, running his fingers up and down her back. “I’m sure I’ll come up with something for someone else, should I get bored.”

“I don’t know, he’s – ” Julie trailed off. Her son wasn’t exactly a ladies’ man. They never really talked about sex.

“You can take as long as you need, there’s no deadline for this. I’ll pay for whatever new clothes you want, or makeovers, or vacations you want to take him on – whatever you think will help you and him be able to do this.”

“What if he doesn’t want to do this?” Julie asked.

“Well it takes two to tango, dear.”

Julie smirked, looking down to her lap, sighing deeply. She closed her eyes, thinking more about the money, the request, and her son. “A penis is a penis,” she told herself in her head, trying to rationalize this challenge.

“If you want to think about it, you can. Let me know what you decide, or don’t. Your silence would be the answer. If I install a camera, and months, or years pass and if doesn’t happen, that’s fine too. As I said there’s no deadline. If my surveillance software captures video footage of you and him having sex, then you get the money. Also, rest assured, I would not upload the video to the internet. I’m not even sure how to do that to be honest!” The old man joked.

Julie shook her head and climbed in the covers to lie on her side, still facing away from Bob. She blankly stared out of his bedroom window. She thought about Ray and wondered what he was up to at the sleepover at his friend’s house. They were probably staying up all night to play video games. Images of his thin frame, kicking a soccer ball around in the backyard popped in her head causing a smile to come across her kaçak iddaa face. He loved soccer.

“Well, do you have an answer?” Bob whispered in her ear, and then smelled her shoulder length, dirty-blonde hair.

Julie didn’t answer; she closed her eyes instead, as Bob ran his hand up and down her waist and hip.


She sighed, rolling onto her back, looking up at Bob’s face. He brought his hand to her cheek, caressing it gently. “Twenty million dollars, Julie,” Bob reiterated, running his thumb across her lips.

“Twenty million dollars,” He said again. Julie opened her mouth slightly and took Bob’s thumb in, slowly rolling her tongue around it, then gently suckling on it.

“What do you say?” Bob asked, taking his thumb from her mouth, moving his hand down to her breast, then rubbing his saliva coated thumb across Julie’s erect nipple, sending tingles down her spine.

“Yes.” Julie said flatly. “I’ll do it.”

Chapter 2

Julie stood nude in her bedroom in front of the full length mirror in the corner next to her closet. She turned from side to side observing her body. Anytime she saw herself naked she couldn’t help but think of her past – how she used to look. When her husband left her and Ray for a younger women five years ago, it was actually the best thing to happen to her. One of the positive outcomes was Julie losing close to 20 pounds via dieting and exercising. She slimmed down, sporting a firm and somewhat toned body. A six-pack set of abs isn’t visible, but she looks as good as she did shortly before she got pregnant at age 22, with Ray.

She ran her fingers through her hair. No longer did she have a long pony tail, instead maintaining a shorter, shoulder-length look was another change she made to her appearance after her ex left. She had bangs that slightly parted and were very cute.

Julie smiled in the mirror, looking into her own blue eyes. Her overbite was very noticeable, and she was made fun of as a teenager for it, but now she loves her toothy grin. It wasn’t quite a “horse mouth” but resembled a Marie Osmond-like toothy grin. It never seemed to bother her sexual partners, who always asked for and complimented her fellatio abilities.

She turned to the side to admire her well toned and shapely butt, running her hands up and down her sides. Sex was another positive change that occurred for Julie after her husband left. It happened so much more frequently in the last five years. Perhaps it was her way to get even with her ex or perhaps he leaving her awakened something inside her. Perhaps it was a self confident, motivated, stress-free attitude – one that enabled the then 36 year old to go out, have fun, make friends, make love, and enjoy life.

Enjoy life she did. She shunned any sort of committed relationship the many suitors wanted with her. Not only did she not have the time, due to her work schedule, but she didn’t want herself, or her son, to be hurt again. She didn’t want to remarry only to have that fall apart as well. It was a form of fear that being hurt created, but she chose to ignore it for the time being, opting to deal with it at another time. So instead, she opted for the “friend’s with benefits” method of satisfying her sexual needs. Her older sister, Holly, advised that this would be best for her. Holly was always a sexual creature, sharing lovers, swinging, and being very open about it. Julie was never quite as promiscuous as Holly, but looked to her for advice and someone to emulate to some degree. Holly always shared her sexual wisdom with her younger sister; sometimes even asking her to try certain things, suggesting certain positions or methods, and expanding Julie’s own sexual knowledge exponentially.

There were many friends that came and went. Usually the men that went were the ones that developed feelings for Julie or found a woman that wanted a long term romance. There were a few, however, that understood her and had no issues with being a friend who occasionally provided sex. One such friend had very similar desires as Julie. She met Ulysses on a blind date. He was black, a few inches taller than her at 5’10”, long braided hair, and a perfectly muscled fitness model. He traveled a lot, but anytime he was in town, they would make a point to go out for a late dinner when Julie’s shift was over, or have dinner at his apartment. Either scenario ended with enjoyable conversation followed by even more enjoyable sex.

Julie turned to face the mirror, pulling one of her large breasts toward her mouth, licking the nipple playfully, and thinking about Ulysses. She released the breast, staring blankly into her own eyes. Her thoughts went to the previous night with Bob and his challenge – twenty million dollars. She sighed, looking down and rubbing her temples.

“This should be easy,” she thought, walking toward her bathroom. “Maybe I should talk to Ray about it, maybe it’ll all be ok,” she pictured informing her son of this challenge as she turned on the water faucet in the shower. kaçak bahis She moaned while the hot water poured over her, gently pinching a nipple, and sliding her other hand down her abdomen. She casually rubbed her clit, now thinking about her last evening with Ulysses three months ago. She slid two fingers into her pussy and moaned softly again. Her thoughts quickly shifted to Ray. “How do I even begin to do this? He may be angry or terrified.” She thought, licking her index finger of her juices before plunging it back in and making a circling motion. She attempted to think of things from Ray’s point of view. She thought about what Bob said: a young man benefiting from an older teacher. She shook her head and smirked, the mood had passed. “I would never hurt you, Ray. I have to figure this out though.”

Julie lay on her bed, naked, looking up at the ceiling, as the ceiling fan helped to air dry her. “Should I let him catch me naked? Should I try flirting with him? What if it freaks him out? Maybe I should take it slow,” she asked herself before hearing Ray arrive.

The front door pushed open and Ray called to Julie from downstairs, “Mom? I’m home.”

There was a pause as Julie took a deep breath, not moving from her position on the bed. “I’m up here.”

“Ok” Ray said as he started to climb the stairs. Julie remain laying on the bed, she wanted to test herself to see what would happen if he saw her naked. Closer and closer he got to her bed room. She couldn’t hold out anymore, she grabbed the white robe next to the bed and was loosely tying it when Ray came into view.

“Oh hey there. Hey.” Julie nervously said. She usually called him “sweetie” or “baby” but didn’t this time.

“Hey mom. No work today?” He asked, standing in Julie’s doorway.

“Nope, I’m off today! Come in, come sit.” She said, sitting down on the bed, patting the mattress next to her. She straightened her hair and checked her robe, it was revealing quite a bit of cleavage, but nothing too outrageous.

“Ok.” Ray sat on the bed next to her and scratched the back of his neck.

“Soooo…” Julie said, placing her arm around Ray. “Have fun last night?”

“Yeah it was cool. We mostly played videos games. Just stuff like that.”

“I see, I see,” Julie looked up at his hair, tousling it with her other hand.

“Hey,” Ray annoying bent his neck, moving his head away from her hand. Julie poked him in the side.

There was an awkward silence as Julie struggled to come up with something to say. “Do you, uh, I was thinking, since I don’t work today or tomorrow that we could hang out.”

Ray shrugged, “Yeah ok, that’s cool I guess.”

“Great!” Julie responded a bit too enthusiastically. “Let’s go to dinner tonight. First, I need you to trim those trees next to the driveway. I don’t want any limbs falling on a car if it ices up again. Ok?”

“Oh crap, I forgot about that. Yeah ok, I’ll do it.”

Julie smiled, watching Ray sigh as he looked down to his knees. She cleared her throat, and turned slightly to her side, so the possibility of her open cleavage brushing up against his arm would increase. She gave him a very awkward huge, then whispered, “Thank you,” into his ear. She rose up and gave him a slow kiss on the cheek.

They had always been affectionate. Hugs and kisses were always the norm in their close relationship. But this one was different. It wasn’t a peck; it was a slow kiss a woman gives a man. He nodded and got up to leave afterward. “Alright I better take care of that stuff now.”

Julie nodded, watching him leave. She looked down to her cleavage, a nipple was poking out. Ray hadn’t noticed. She sighed then stood to remove her robe. She climbed back into bed tried to think about this challenge; getting that 20 million and not focusing on how stupid she felt.

Chapter 3

Julie stood in her full length mirror once again, except this time she was wearing a new dress Bob had gotten her. It was black, came down to her knees, had long sleeves, and a low neck line which revealed yet more cleavage. It wasn’t normally what a mother would wear for dinner with her son. She was planning on wearing it to dinner with Ulysses when they got a chance to hang out.

Julie turned toward her door as she heard her son knock. “Come in.”

“Hey mom, are you re – ” He stopped mid-sentence, his eyes trailing up and down her frame.

Julie huffed, “I said something nice! Go back and change! Wear a tie, too.”

“Sorry,” he mumbled as he left to change out of his blue jeans and long sleeve t-shirt. Julie shook her head and sighed. She had opted for a teacher role. Slowly teaching her son about dating and if it led to something more, so be it. She knew there was no way tonight would be the night for this to happen. It couldn’t – mainly because Bob hadn’t yet installed the camera in her room.

“Much better,” Julie said, walking past Ray down the stairs. He was wearing khakis and a blue long sleeve shirt with a red tie. “Would you grab my coat please?”

“Sure,” Ray said, handing her the long black coat. “Here.”

“What are you doing?” Julie asked.

“Your coat? Didn’t you want it? Here.” Ray said, holding the coat out to her.

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