The Challenge_(0) by tw_holt

Author’s note: First of an eight part series.

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 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 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.

“Julie?”

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. 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.

“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?”

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.

“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?”

“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.

“Oh Ray, this is beautiful,” she trailed off in a euphoric daze. The sun was rising on the couple, who decided to be extra adventurous shortly before they were scheduled to return home.

Ray grabbed her and pulled her up, she wrapped her legs around him, and they kissed as the sun rose over the horizon.

“I love you, so very much.” Julie told her son.

“I love you too. I want to do this forever with you.” Ray replied.

“We will.” She said with a soft smile, the orange light of the sun illuminating her face.

Later that day they collapsed on Julie’s bed back home, exhausted. They had barely gotten any sleep in the last few days. “Mom, my penis is not doing too well.”

“Let me see,” Julie said, unzipping his pants, and pulling it out of his boxers. She smirked, “Yep, you my son, are chafed pretty badly. I’m fairly chafed too. The tip is red. It’ll be back to normal in a few days. Moisturizing lotion will help.”

She collapsed on the bed next to him, “We’ve been going at it quite a bit. Probably need to rest a little. After a nap we can use some lube from my top drawer, it may provide extra lubrication”

“Yeah,“ He said, opening his arm for her to snuggle into.

Shortly after midnight on Sunday morning, Ray wiped his forehead of sweat. Julie was sweaty too. They had been going at it for over an hour. The bottle of lube was next to the bed. Ray rolled onto his back, taking her with him. She ran her fingers through her hair and flung sweat playfully onto her son. He shook his head and smiled back up to her. They continued, shaking the bed, rolling around and writhing in ecstasy for another hour.

The camera in Julie’s room was off. There had been no mention of Bob’s challenge or the money in the last few weeks.

Chapter 16

It was May. Julie took Ray’s picture in his cap and gown on his high school graduation day. “I’m so proud of you!” She said as they embraced.

The last month and a half since their Bahamas trip, they made love every day. In the morning before Ray went to school, and later that night when Julie returned home from her shift. On the weekends they never put clothes on or left their bed. For the next several weeks this was the routine.

That night, Julie rose on her elbow, gently running her hand on Ray’s chest. “I talked to your Aunt Sharon today.”

“Oh yeah? How is she?” He asked, casually caressing her butt cheek.

“Good. Having some problems with the guy she’s seeing, but otherwise good.” Julie paused, not yet wanting to tell Ray that Sharon asked about the challenge and how it was going.

“Ever feel like you’re forgetting something?” She asked her son.

“Yeah sometimes, why?”

“I think we’ve both forgotten something.” She replied, looking at the corner of her TV on the wall, where the camera Bob installed was slightly poking out.

Ray laughed, “Wow, yeah I guess we have forgotten something!”

“Do you still want that money? Do we still need it?”

Ray paused, “We don’t need it. We have each other.”

“You read my mind. All I need is you, sweetie.”

“It would be nice though, wouldn’t it?” Ray asked.
“It would. It would indeed.” Julie said, reaching down to grip his cock. “I have an idea.”

“Julie, Ray! Come in, come in!” The jovial Bob greeted them at his door the next afternoon. “What do I owe this honor?”

He led them to his study area. He sat in a chair behind a large desk, while Julie and Ray sat in two chairs in front of it. She was smiling at Ray, “Do you want to start?”

“Sure,” He said, standing and extending his hand to his mother.

“Remember what we talked about; just pretend he’s not there.” She reminded her son.

“Yep,” Ray nodded and leaned in to kiss his mother. They made out passionately for a few minutes. Bob’s eyes widened as he stood and moved to one of the chairs on the other side of his desk where his two guests were sitting.

Julie chuckled and began to unbutton Ray’s shirt, still kissing him. She then unzipped her shorts, with Ray assisting at sliding them down. They slid down to her feet and she stepped out of them. Ray removed his shirt, and Julie did the same for hers. Again, wearing no bra or underwear she was already nude. They resumed kissing and Julie unzipped his pants, pulling them down. She went to her knees and fished out his cock and then began to hungrily suck at it. She motioned Ray to lie on the nice wood flooring of Bob’s office. Julie turned around and climbed on Ray, she continued sucking him off, and he went to work on her pussy – licking and swirling his tongue all around inside it while in a lovely 69 position. She paused and looked up at Bob. He was stroking his cock. She grinned and resumed sucking Ray’s.

After she had an orgasm from Ray’s excellent oral skills, they broke the 69, and Ray sat up. She straddled him and began bouncing wildly on his cock. For several minutes she rode him to another mutual orgasm. When she calmed down, she kissed Ray, and then got off him – his sperm dripping onto the floor as she crawled over to Bob like a hungry cat. She grabbed his cock and took it in her mouth, sucking as Bob looked on in shock. She sat on her knees and grabbed her tits, letting them plop on Bob’s lap, engulfing his cock. Within a minute he was ejaculating in her mouth. She slurped up as much cum as she could and crawled back over to Ray. They both sat on Bob’s floor, holding each other and smiling at him.

Bob couldn’t move for a few moments as he regained his composure. He slowly stood, putting his cock back into his pants. He turned and held onto his desk for support. He went over to his chair, plopping down in it, taking a handkerchief and wiping beads of sweat his forehead. After a minute or so, he opened a drawer to his right. He rummaged for a pen, and began writing something. He cleared his throat and started to stand. He again, held on to his desk for help with balance as he made his way to Julie. She stood up and looked at him curiously.

“Here,” Bob said, handing her a check, his hand slightly shaking. “Happy Mother’s day.”

Julie opened the check. It was made out to her and it was for $40 million dollars.

A week later, Julie threw a wad of $100 bills in Ray’s face, and resumed bouncing on his cock. Their bed was covered cash, not all of the $40 million obviously, but just enough to make rolling around on a cash-covered bed as they made love, fun. She scooped some more cash in her arms and threw it in the air above them, the mother and son laughing as it rained down on them. Ray slammed her down on the bed, his hips bucking forcefully into her.

“Fuck me! Yes! Harder!” Julie commanded, as she grabbed some more bills on the mattress. She wrapped her arms around Ray and released the bills. He rose up and pulled her with him, making her scream in pleasure with each thrust.

“I love you!” She cried out as the orgasm overtook her. Ray lowered her onto the bed, and kissed her tenderly.

“I love you too.” He whispered and kissed along her neck. He rolled over to his side, his face inches from hers. She gathered up some more cash and let it float gently down onto them. They smiled at each other and drifted off to sleep, with their foreheads touching.

The end.

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