Jennifer woke up smiling, feeling more refreshed than she had in months. All night long, her dreams had been full of little reminders of how well she tackled her tasks yesterday. Completing chores. Checking items off her list. Watching the virtual confetti fly. It left her feeling a sense of accomplishment, as though she had really done something worth doing.
She also dreamed about Nate. A lot. It felt as though every time she accomplished something in her dreams, she’d look up and there was Nate, smiling at her, melting her heart. It made a lot of sense to Jennifer. Nate created the app just for her. Everything she accomplished yesterday was because of her son. She definitely owed him for that, she decided.
Jennifer eagerly grabbed her phone off the nightstand and opened up Nate’s checklist app. A grin spread across her lips as it loaded a handful of new tasks for the morning, along with a reminder that she was nearing level five. Her eyes scanned the list of new tasks, landing on one titled “wake-up call.” Intrigued, Jennifer clicked on the task, feeling a sense of motivation as the familiar confetti flowed down the screen.
Jennifer read the instructions for the task. It was pretty self-explanatory. She was to go to Nate’s room and wake him up so he could get ready for school. Normally, Jennifer would wait until she was dressed for the day to make sure Nate was up, but today it just felt right to go down to his room straight away. She was wearing the same tank top and pajama shorts he'd seen her in last night, so her attire wasn't particularly inappropriate. Besides, she already clicked on the task in the app; she might as well complete it and earn the points.
Jennifer opened the door to her room and crossed the hall, grabbing hold of Nate’s doorknob. Without giving it much thought, she turned the knob, pushed open the door, and stepped into her son’s room. Before she could finish scanning the space, her eyes went wide, and she froze in her tracks, gasping at what she saw. There was Nate, lying in his bed, sound asleep, completely uncovered, and stark naked. Naked and very erect.
Her eyes went wide as she saw her son in this state for the first time in his adult life. Almost immediately, she found herself focusing on his cock, mouth agape. It was absolutely enormous, easily the biggest that she’d ever seen in person. Jennifer held her breath as she stared. It wasn’t that it was just long. It was also girthy, with veins that drew her eyes up and down its length. There was no other way to put it—Nate was hung. Despite her shock and the fact that this was her son, Jennifer couldn’t help but find the sight incredibly arousing.
Reminding herself that she was Nate’s mother, Jennifer regained her bearings, forced her eyes down to the ground, and stepped back out of her son’s room. Pulling the door shut, the woman took a deep breath. Part of her wanted to erase the image from her mind. Another part of her knew she never could. Deciding to complete the task she set off to accomplish, the woman brought her hand up to the door, knocking loudly several times.
“Hey, kiddo!” She called, doing her best to sound like a cheery mom that hadn’t just been ogling her son’s dick. “Wakey wakey!”
She heard Nate grumble from the other side of the door, confirming that he was up. Jennifer told him she’d see him downstairs shortly and then scrambled back to her room to catch her breath and check the task off her list.
Jennifer tried to put the image of her son’s cock out of her mind, but it followed her all morning long. She tried to shake it off by tackling items from the checklist, but that didn’t help. It seemed like the more tasks she completed on the app, the more she thought about his big, stiff member, and the more the thought turned her on. Initially, she was disgusted with herself. After all, this was her son whose cock she kept thinking about. As she completed more items on the checklist app, though, it became easier and easier to justify her growing feelings of lust.
By the time she reached level five in the app, Jennifer had it all figured out. She hadn’t been with another man in years. It was only natural that seeing a cock, especially one so impressive, would trigger strong feelings inside her. It wasn’t that she wanted her son. That would be absurd. She was just in need of a good, hard fucking. Jennifer felt a sense of relief when she realized that her arousal wasn't due to her son, but rather because this was the first cock she'd seen in a long time, and it was truly amazing. With this newfound revelation in mind, she set off to complete even more tasks on the app and felt better by the minute.
When Nate finally wandered downstairs for breakfast, Jennifer had completed nearly a dozen items on her morning checklist. The feeling of accomplishment and appreciation for her son’s part in it was so strong that as soon as she saw him, she pranced up to Nate, wrapping him in a massive hug as she gave him a kiss on the cheek.
“Well, good morning,” Nate grinned as they separated. “What was that for?”
“Oh, I was just feeling thankful for this amazing app, not to mention my genius kid who created it,” she replied, holding up her phone with a screen full of checked-off items. “Look around; this place is spotless, and I couldn’t have done it without your help.”
It was true. The house looked better than it had in ages. There wasn’t a cobweb to be found, and Jennifer had even managed to make a massive breakfast for the two of them.
“I knew you’d get hooked on that app,” Nate said as they sat down to eat breakfast. “I bet it will change your life in no time.”
“It already has,” Jennifer said as their eyes met.
After breakfast, Nate headed off to school, and Jennifer set about earning more points on her checklist. One by one, she completed items on the list, earning her way closer and closer to the sixth level. She especially enjoyed the “Self Care” prompts, practically running to her room to get herself off every time one popped up on the list. Each time, she found herself thinking about Nate and his massive cock as her fingers worked her clit.
The first time she started masturbating to the thought of Nate, she reminded herself that it wasn’t that she was attracted to her son; she was just in need of a cock, and she happened to see his last. The second time, however, she found herself admitting that Nate really was sexy. By the fourth time the app told her to go get herself off, she had come to a surprising conclusion—she truly wanted Nate. Of course, she’d never act on those wants; she was his mother, after all. Still, that didn’t mean she couldn’t embrace the fantasy for her own private time.
“Oh yes, oh fuck, Nate,” she moaned as she stroked her pussy. “Yes, fuck me, Nate. Fuck me so hard.” As the thoughts of fucking her son flowed through her mind, Jennifer came harder than she had in years, screaming in pleasure as her body shuddered. After the self-care session, Jennifer was delighted to watch the confetti fly as she checked off the item and was doubly rewarded by stepping up to level six in the app.
Jennifer had completed everything on her list about fifteen minutes before Nate was due home from school. She was even on the cusp of moving up to the seventh level, with just ten points to go. Eager to advance, she hit the refresh button, but no new tasks showed up. Furrowing her brow, she hit the refresh button several more times, with the same result each time.
“Come on, come on,” she grumbled, hitting the refresh button a few more times. “Give me something.”
After a few more tries, a new task finally showed up on the list. Jennifer smiled at having a new task to check off her list, but then her eyes went wide as she saw the title.
“Relationship coaching with Nate” read the solitary unchecked item on the checklist. Jennifer gulped, wondering what kind of relationship coaching the app wanted her to do. She took a deep breath, letting her finger hover over the task before finally clicking on it to see the description. As the confetti popped across her screen, Jennifer felt a sense of ease. She could do this. It would earn enough points to bring her up to level seven. She just needed to make it happen.
As the confetti cleared her screen, Jennifer read the task description. “Nate doesn’t have a girlfriend,” it began. “This may be due to being unsure of himself. Find out what's holding him back and offer to do whatever it takes to help him feel at ease."
Jennifer considered the instructions. It was true; she couldn’t remember Nate ever having taken a girl out on a date. Nate’s dad died right around the time that most dads were beginning to explain all of this stuff to their sons. Jennifer started to worry. Should she have noticed this before? Could she have done anything different? Nate was tall and attractive. He should have girls falling all over him. Had she failed him as a parent? The app was absolutely right, Jennifer realized. She needed to help Nate.
By the time Nate walked through the front door, Jennifer knew exactly what she needed to do. Calling her son into the dining room, she gestured for him to sit down at the table across from her.
“Um, what’s up?” Nate asked. “I’m not in trouble, am I?”
“No, of course not,” Jennifer replied. “If anything, I’m the one who might have done something wrong. Nate, when your dad passed, I just kind of took it for granted that the other men in your life would make sure you got through to adulthood, and I took a back seat to teaching you about relationships and everything that goes along with it. Then today, I had a revelation. You’re a high school senior, just a few months from graduation, and I’ve never seen you go out on a date. That’s not typical, especially for a smart, good-looking young man like yourself. That’s why I thought it would be a good idea if I sat down with you and found out if there’s anything I can help you with.”
“What do you mean?” Nate asked.
“I mean, I want to know if there’s anything holding you back. If there is, I want to help you get through it. I’m your mom. I want you to succeed in everything, and that includes relationships.”
Nate paused, looking over his mom briefly before speaking again. “I suppose,” he began, “there are some things that I could use help with, but only if you really wanted to do it.”
Jennifer smiled, eager to help her son and earn the points in the app. “Honey, I’d help you with anything. What’s bothering you?”
“Okay, so my biggest problem that I’m having now is really that I’m nervous about dates. I mean, I kind of get how they go. You pick the girl up. You go do something fun. You take her home, and if it goes well, maybe you give her a kiss, right?” Jennifer nodded her head as he continued. “The thing is, I’m just kind of nervous about all of that. That’s probably the place I’d need to start if I really wanted to feel more confident.
Jennifer’s eyes lit up as she realized what she could do to help. “Well, then, let’s do it!”
“Do what?” Nate asked.
“Let’s go on a date! If that’s what you’re feeling uncomfortable with, the best thing we could do is practice it. Come on, I don’t have any plans for tonight, so let’s help you get over this. Get your homework done, then go plan a date for the two of us. It’ll be fun.”
Nate grinned. “Really? You’d do that for me?”
“Absolutely,” she smiled back.
About an hour later, Jennifer was nearly ready to go out on her date with Nate. After her jump to level seven in the checklist app, the program came up with all sorts of great tasks to help her get ready. She found a great outfit—a super cute blouse that showed a hint of cleavage, paired with a powder blue skirt that showed a lot of leg. She got her makeup on. She even managed to take a break to get herself off once more as she fantasized about Nate’s cock. By the time Nate was taking her out the door, she was within twenty points of reaching level eight.
The date itself was absolutely perfect. More than once, Jennifer found herself forgetting that she was out with her son, getting lost in the dinner conversation and mild flirting over dinner. Later, they went to see a movie, and Jennifer found herself feeling very content as she nestled up into Nate’s arm. She knew she shouldn’t, but as the night wore on, the mother found herself wanting Nate more and more, in ways that a mother shouldn’t want her son.
Then, during the drive back home, Jennifer’s phone dinged with a notification. Turning her phone’s screen on, she noticed that the notification was from her checklist app. Remembering that she was nearly at the eighth level, she opened the app. When she saw the item on the checklist, her eyes went wide. The task was just two words long—”First base.”
Jennifer's heart pounded. She was fairly certain she knew what the app was going to tell her it wanted her to do. Part of her wanted it too. Clicking on the task, she enjoyed the confidence boost from the flying confetti, and she silently read the description as Nate continued driving them home.
“Was it a great date? Show him you liked it and help him practice for the real thing by taking Nate to first base. Let Nate know he treated you well by returning the favor with a sexy makeout session.”
Jennifer’s head spun as they neared their home. Could she really do this? She knew she wanted it. If she was honest, she wanted more than that. At the same time, Nate was her son. Her son just took her on an epic first date, she acknowledged. If a guy she’d never met took her on a date that amazing, she’d probably be in his pants by now. The least she could do is let Nate see how a girl his age would react to such great treatment. As they pulled into their driveway, Jennifer made up her mind.
“Thanks for letting me take you on that date,” Nate smiled as he killed the engine. “It was a lot of fun.”
“What makes you think the date’s over?” Jennifer purred, unbuckling her seatbelt and turning to face her son.
“What do you mean?” Nate asked, a faint smile on his face.
“What I mean,” she began, moving her face closer to Nate’s as she spoke,” is that you treated me really well tonight. I had a great time. And when a guy gives a girl a great time like you did tonight, sometimes, the girl will want to show her appreciation. Sometimes, a girl wants to make sure her guy knows that she wants more. Sometimes, a girl wants this.”
In an instant, Jennifer shifted into Nate’s lap, straddling him in the seat as she pressed her lips into his. Nate let out a little groan, closing his eyes and kissing Jennifer back as he wrapped his arms around her. Jennifer moaned into Nate's mouth, allowing her tongue to slip into his mouth as they began to kiss. Gradually, all the woman’s reservations melted away, leaving nothing but a fiery hot passion as they kissed in the front seat of Nate’s old sedan.
“Oh, God,” Nate moaned between kisses. “Oh, Mom, I want this so bad.”
“Me too, baby,” Jennifer moaned. “You kiss, oh, God, so good.”
Somehow, the pair managed to get from the car and into the house as their makeout session continued. Jennifer groaned as Nate pressed her into the wall and planted kisses up and down her neck. As he did, she could feel his cock grinding up against her leg. She couldn’t help but remember how sexy he looked when she found him naked in the morning. Part of her wanted to get him naked right now, to see what his cock looked like once more. Another part of her realized that she would be going too far if she did.
Deciding that she needed to put an end to this before she let herself go too far, Jennifer gave Nate a gentle push backward. Once the two were separated, she smiled at him, leaning in to give him a little peck on the lips.
“Now that’s how you finish a date,” she smiled into her son’s eyes. “Thanks for taking me out tonight, Nate. Now, it’s getting pretty late. I think we’d both better get to bed.”
Nate leaned in to kiss Jennifer once more, and after letting the kiss linger for a few seconds, the woman playfully pushed him back once more, swatting his butt and telling him to get upstairs. A few minutes later, Jennifer was up in her room, groaning as she fingered her pussy to more fantasies about Nate.
