Thursday
Maggie glanced out the kitchen window. Her eyes scanned the bleak, cloud-filled sky as she put the groceries from her shopping trip away. Everything was gray and dreary, and she could definitely relate. She'd had the time of her life over the last three days, spending lots of quality time with Jack. Finding herself in the middle of a whole day without seeing him left Maggie feeling melancholy.
After putting away her groceries, Maggie entered the dining room. Jack's relaxation device, sitting proudly on the shelf, immediately drew Maggie's attention. It was playing its catchy little tune, and seven of the ten tiny lights on top glowed softly. The little tune was always bouncing around in her mind lately, but there was something soothing about hearing it directly from the device.
Maggie hummed along to the little tune emanating from the device. As she did, her mind wandered, drifting to the verse that she'd come up with earlier that morning.
Go on dates with Jack.
When the line first popped into her mind, Maggie dismissed it almost immediately. After all, she was a married woman. Going out once might be fun, but dates, plural? That was dating, and dating someone other than her husband felt wrong, even if it was with someone as incredible as Jack. As wonderful as living out the previous verses turned out to be, dating Jack was one line she couldn’t cross.
Go on dates with Jack.
Still, it didn’t hurt to think about it, did it? Maggie pictured what it would be like to start dating Jack. He was such a gentleman every time he came over to her house. He was excellent at getting her turned on, too. His kisses were magical. Everything about Jack was just perfect. Maggie couldn’t help but dwell on all the wonderful experiences she’d had with him over the last few days. If she were younger and single, she’d be throwing herself at the prospect of dating such a stud of a man.
Go on dates with Jack.
Honestly, Maggie wondered, would it be so terrible if she started dating Jack? What was dating, really? It’s just two adults spending time together, and that’s not really cheating in and of itself. Plus, it would be helpful for Jack. The poor boy admitted yesterday that he didn’t have a girlfriend. How would he ever gain valuable experience with women unless someone helped him do so? By going on a few dates with him, Maggie would be setting him up for success with whatever girl he would eventually wind up with.
Go on dates with Jack.
A faint smile materialized on Maggie’s lips. Yes, she could absolutely go on dates with Jack. It was harmless fun, and it would even be beneficial for Jack. The more she thought it through, the more she realized that dating Jack was actually a fantastic idea. Maggie made a mental note to talk to Jack about it the next time he was around.
Make contact with Jack.
Or she could talk to him about it right now. Maggie’s smile broadened as she realized that she had Jack’s number saved in her phone. Racing back into the kitchen, she grabbed her phone from the counter and scrolled through her contacts. When she reached Jack’s name, she clicked the button to send him a text and started typing.
“Hey, stud,” she began, “miss me yet?”
A few moments later, Jack responded, “LOL of course, Mrs. Harris! What’s up?”
“Well, I know you’re busy today, but I was wondering when you’d be free tonight. I thought it would be fun if we could go out and make up for some lost time.”
“You mean like a date?” Jack texted back.
“Exactly!” Maggie typed. “What do you think?”
“I think that would be great,” came Jack’s reply, along with a smiling emoji. “I could be over at your place around 7:00, if that’s fine.”
“Perfect.” Maggie typed out. “I’ll see you then!”
Suddenly, Maggie’s entire day became infinitely better. Jack was coming over tonight! Not only was he coming over—he was coming over to take her out on a date. Their first date.
Maggie felt butterflies in her stomach as the realization hit her. It had been over twenty years since the last time she’d gone on a first date with anyone, and that date was rough. Her first date with her husband was so awkward. They were both kids who didn’t really know what they were doing. Maybe tonight, Maggie realized, her first date with Jack would make up for her last first date. She was walking on clouds as she pranced to her closet, imagining what the perfect first date with Jack might look like.
A few moments later, the woman eagerly searched for an occasion-worthy outfit, jostling and rustling hangers full of dresses. As she eliminated one dress after another, she found herself frowning in disapproval. This one was too casual. That one was too formal. None of them showed nearly enough skin for Jack. Just as she was about to walk away in frustration, she saw it.
Reaching past several other outfits, Maggie’s hand plunged into the far back corner of her closet. When it returned, she found herself holding a hanger containing a dress. This wasn’t just any dress, though. This was a scandalously short, low-cut black dress with a plunging neckline that showcased more cleavage than anything else she owned. She’d purchased it years before, and after wearing it out one time on a date with her husband, she dubbed it “the forbidden little black dress.”
Maggie slipped into the dress, immediately remembering the reaction it stirred up, not just in her husband but in pretty much every other man she’d encountered that night. She never wore the dress again because, at the time, the idea of anyone other than her husband looking at her like that felt wrong. Now, the idea of Jack looking at her with that sort of hunger turned her on like nothing else could. Appraising herself in the mirror, she smiled at what she saw. This was the perfect foundation for an incredible first date with Jack.
Maggie had undergone a transformation by the time Jack knocked on her front door at precisely 7:00 p.m. Her hair was perfect. Her makeup was flirty. Her dress hugged her curves and showed off tons of skin. Maggie couldn’t help but smile as she swung open her front door, and Jack’s jaw nearly hit the floor. Maggie sensed the boy's persistent, gentle confidence crumbling for the first time this week as he cleared his throat.
“Wh, wow,” he stuttered, looking the older woman up and down and drinking in her generous cleavage. “Mrs. Harris, you look great.”
Maggie grinned seductively. “Why thank you, Mr. Morris. So, what did you have planned for us tonight?”
The teenager paused for a moment to compose himself. “I was thinking,” he finally began, “there’s this nice restaurant that I’d love to take you out to. They have this really awesome outdoor seating area that overlooks the river. I’ve heard it’s a great place to bring a cute girl. After that, if it's okay with you, I thought maybe we could come back here to watch a movie. Does that sound good?”
“That would be wonderful,” Maggie purred.
Jack extended his arm, which Maggie took, and the two were off. As they drove to the restaurant, Maggie found herself gazing at the young man while they chatted. He looked fantastic tonight in his slacks and button-down shirt. His sandy hair was combed neatly, and the way he smiled every time he glanced at her from the driver’s seat set Maggie on fire. As much as she was looking forward to dinner, part of Maggie wished they could skip it and go straight back to her place to fool around.
When they arrived at the restaurant, Jack opened Maggie’s door for her and took her by the arm, leading her inside. Maggie smiled when Jack stepped up to the greeter and told them he had a reservation. He had really thought of everything. A moment later, they were led to a beautiful table on the back patio. Maggie felt the eyes of a man at a nearby table on her as she took her seat across from Jack. A shiver of delight traveled down her spine. If some stranger was looking at her like that, what was Jack thinking?
Dinner was absolutely wonderful. Maggie loved hearing Jack talk about his life, almost as much as she enjoyed taking every chance she could to flirt with him. As they talked, Maggie kept catching Jack’s eyes drifting down to her generous cleavage. It was so thrilling for the woman to know that she could captivate the young man so strongly.
By the end of their meal, Maggie had to fight not to drag him to his vehicle. Once both car doors were closed, Maggie was all over Jack, straddling him in his seat as her lips pressed hard against his. Jack’s hands roamed up and down Maggie’s back, and the woman moaned passionately into his mouth as their tongues dueled.
Somehow, the two separated long enough for Jack to drive back to Maggie’s home. As soon as they stepped through the front door, Maggie could hear the tune from Jack’s device begin playing in her mind. For some reason, she hadn't heard the melody during their absence, but now it had returned, making up for the lost time. As the tune played, all of the lyrics she’d come up with over the past week came flooding back, reminding her how much she wanted this young man next to her.
Make contact with Jack.
Maggie took Jack’s hand and led him over to the sofa. With a playful smirk, she pushed him down. As the woman straddled him, Jack looked up at Maggie with a grin on his face. She could feel his bulge pressing into her, driving her wild. Smiling brightly into his eyes, she toyed with one of the straps on her dress.
Show some skin for Jack.
“I’ve watched you undress me with your eyes all night long,” she said, resting a hand on his chest. “How about you do the real thing?”
Without needing any more prompting, Jack took Maggie’s dress by the hem and pulled it up and over her head. She heard the boy sigh as her black lace panties and braless tits came into view. With the dress up and over her head, Jack tossed it on the floor nearby and stared at the woman in the dimly lit room.
“Like what you see?” she grinned.
“I like it so much,” Jack replied, his hands rising up to cup her breasts. Maggie closed her eyes, enjoying the sensation as Jack fondled her for a few moments. “You are so hot, Mrs. Harris,” he breathed.
Be kissy with Jack.
“You’re pretty hot yourself,” Maggie admitted, leaning forward until her lips were barely hovering above his. “Now, kiss me, Jack.”
Almost immediately, their lips met in a passionate embrace. Maggie groaned as their lips parted, and she felt Jack’s tongue meet hers. The two kissed for what felt like forever as their hands roamed and explored each other's bodies. Maggie slowly began grinding her hips up and down on Jack’s shaft. He was enormous and so hard. Even through all of his clothes, his cock felt so good.
Masturbate for Jack.
And if it felt so good over all his clothes, Maggie reasoned, it would feel infinitely better with all his clothes off. As their tongues dueled and his hands roamed up and down her back, Maggie’s fingers went to work, tugging Jack’s belt loose. After undoing his belt, she unbuttoned his slacks and then grabbed his pants and underwear by their waistbands.
She groaned, breaking their kiss, and pushed herself off Jack, saying, "I need to get these off you." Taking the hint, Jack lifted his hips off the sofa while Maggie tugged. An instant later, Maggie let out a gasp as the young man’s cock came into view. It was her first time seeing it like this, and it looked so big and so sexy.
As she pulled his clothes off and tossed them over by her discarded dress, Maggie gave serious thought to sliding her panties aside and just taking him inside her. He was so big. It would feel so good inside of her, filling her up. As much as she wanted to, she knew that was a line she couldn’t cross. She was a married woman, after all. A little fooling around with the neighbor kid was harmless fun, but she knew she couldn’t go overboard.
Instead, she sank down on her knees in front of the boy. Taking his cock in one hand and his balls in another, she slowly began stroking him off. Not too fast at first—she wanted this to last. Jack groaned happily as Maggie’s hands ran up and down his hard member, pumping him slowly and sensually. As she did so, a new line to the melody in her head started to materialize.
Give some head to Jack.
A grin crept onto Maggie’s face as she considered the words. Wouldn’t that be naughty? She was so close to his cock already. It would be so easy to lean forward just a bit more, to take him in her mouth, and really make their first date memorable. Still, she had her doubts. Maggie practically never gave her husband head. What would it be saying if she never blows her hubby but goes down on Jack on their first date?
Give some head to Jack.
Even so, Jack's cock looked delicious. As Maggie continued lovingly stroking him off, she couldn’t help but get more and more turned on by the thought of taking him in her mouth. Jack was always so good to her. He helped her throughout the house. He was such a gentleman on their date tonight. He was so sexy. Would it really be so bad to take him in her mouth, just for a little bit?
Give some head to Jack.
Maggie’s grin broadened. Of course, it wouldn’t be so bad. So what if she doesn’t give her husband head? It’s not like he’s out here earning it like Jack is. He’s always on the road for work, leaving her here alone to fend for herself. Jack comes over. He helps get things done. He makes her feel wanted and alive. If anyone deserves to get a little head, it’s Jack.
Maggie made up her mind, looked into Jack's eyes, and slowly brought her head forward to where she was still stroking him off. Without breaking eye contact, she slowly brought her lips to the tip of his cock, giving it a gentle kiss. Jack took a sharp breath, and Maggie planted another kiss on his cockhead before gradually pushing down once more. Her lips parted as she took him deeper into her mouth.
The boy let out a groan as Maggie took him as far as she could. For a moment, she remained there, groaning on his cock as she massaged his balls. Then, slowly, she pulled back until just the tip was in her mouth. Her tongue swirled around his crown, and Jack sighed at the sensation. Then, moving slowly and deliberately, Maggie began bobbing on him. She started off slow, taking time to enjoy the experience. Gradually, her pace increased, along with Jack’s moans of approval.
As she slammed her face on his cock faster and faster, Maggie’s arousal kept building. Before long, her hand made its way beneath her panties, and the woman found herself groaning and moaning on Jack’s cock as he played with her clit. As she bobbed up and down, she felt her own orgasm drawing closer. Maggie could tell Jack was getting closer with his grunting and groaning.
Finally, Jack grabbed a handful of Maggie’s hair, pulling her down on his cock. Letting out a loud cry, he erupted, filling her mouth with shot after shot of his hot cum. At the same time, Maggie found her own orgasm hitting, and she let out a scream onto his cock as she shuddered and shook. She still did her best to swallow as much of his seed as she could, but in her ecstasy, several gobs leaked out onto Jack’s cock and down onto the sofa.
Finally coming down from their mutual orgasms, Maggie pulled herself off Jack’s member and smiled at him. She had a flushed and sweaty face, messy hair, and thoroughly smeared makeup. Even so, she felt better than she had in years. Giving Jack’s cock one last kiss, she looked back up at him and grinned.
“How’d you like that?” Maggie questioned the young man.
“I loved it,” Jack admitted. “I know I can’t wait for tomorrow.
“Oh? What’s tomorrow?”
“Oh, uh, well,” Jack stuttered. “I’m coming over to spend more time with you. Right?”
“Oh, right!” Maggie smiled. “I’d like that. And who knows, maybe we could even go out on another date.”
Later that night, Maggie rested in her bed as she reflected on her day. It started out pretty bleak, but it got pretty incredible once she had her date with Jack. He really was such a wonderful kid. And getting to blow him later on? That was the icing on the cake. She could hardly wait for tomorrow, when he'd come over and give her more of his tasty cum.
As the woman drifted off to sleep, the little tune from Jack’s device grew fainter and fainter in her mind. In her dining room, the device grew more and more quiet, and the eight lights that once shined bright barely remained lit. Moments later, the ninth light came on, burned for a few seconds, and then all the lights flickered and went out as the device grew silent.
