Chapter Text
Ash hummed to himself as he got ready. It was almost time for his date with June and he was looking forward to it a lot. She was awfully pretty and awfully sweet and had just the slightest edge to her that said she wouldn't let someone walk all over her. It promised to be a really fun evening with her and Pikachu was looking forward to hanging out with June's Charmander as well.
There was a knock on the bedroom door and Ash turned to it. He hadn't even realized that there was anyone outside. Quickly crossing over to it, he opened it and looked with surprise at Jessie standing there. The red-haired woman was looking, er, very much like herself lately. Or, to put it another way, she was enjoying how her pregnancy was making her boobs look bigger and her outfits showed that off quite a bit. And it being summer only made her wear even less and show off more of her heavily pregnant body.
"Can I come in, Ash?" Jessie asked, slipping inside right away and closing the door behind her as she spoke.
"Um, sure," Ash said, feeling Jessie brush past him. "What is it?"
"Looking forward to your date?" Jessie asked, turning around and cradling her pregnant belly in her arms.
"Yeah," Ash said, blushing a bit as Jessie ran an eye over him, picking out the freshly combed hair, the washed face, all of that. "It should be fun."
"And what all will you be doing on the date?" Jessie asked, sitting down on the bed in a way that made her breasts bounce despite how Ash more or less tried not to look at them moving around like that.
"I, well, you know," Ash said, wrenching his eyes upwards, long after Jessie had clearly noticed where they had been lying. "Go for a walk down near the creek, go to her place for dinner, then walking back home under the stars."
"Ah, let me see if I have this straight," Jessie said with a nod. "You'll be fucking down at the stream, you'll eat her out and she'll suck you off back home and then you'll bang in as public of a place as you can manage once it gets dark out?"
Ash spluttered at that and not just because he had thought that June was very cute and that the skirts she wore showed off her legs to very good effect or how she really lavished attention on a popsicle while looking at him yesterday as she thought over him asking her out. It was also because this was Jessie right here, saying this sort of thing. He swallowed hard and tried to get himself together, even as his cock twitched a bit inside of his pants.
"She isn't that sort of girl," Ash said, not really knowing whether that was true or not.
"But you're certainly that sort of guy," Jessie said, stretching and leaning backwards, putting her body on rather clear display. "Are you going to tell me that you aren't?"
Ash blushed as he glanced at Jessie's breasts once more, seeing the large mounds pressed tightly together like that, forming such a deep valley. His cock did a lot more than just twitch this time.
"Now, do you really want to have two different girls be knocked up at the same time?" Jessie asked, reaching out and stroking Ash's waistband, running her fingers along it and pressing her fingertips against the bare skin of his stomach. "Do you want to have your mother have to listen to June's parents ranting about their daughter getting bred by her son?"
"I, I wasn't going to do anything risky like that," Ash stammered, shaking his head.
"Uh huh," Jessie said, looking hugely unimpressed at that. "And a few months back, we were all just going to share a bottle of champagne and watch the fireworks. How well did that work out, Ash?"
At the very least, Ash had learned his lesson from that. He had made a private vow not to get so drunk on New Year's ever again. Sure, someone his age shouldn't be getting very drunk in the first place but if he did, at the very least, he shouldn't get so drunk that making a pass at his mother's girlfriend should seem like a good idea. Never mind having said girlfriend accepting the pass with Mom's blurry acceptance and then, well, one thing leading to another and Jessie finding out near the end of January that Ash had fucked a baby girl inside of her. At least none of them had been so drunk that Mom had been knocked up as well.
"You say that you won't do something like that ever again, but just look at this," Jessie said, pressing her hand against Ash's crotch, rubbing back and forth against the rod there and even wrapping her fingers part of the way around the shaft through the pants as Ash panted. "You go out to meet a pretty girl like that, waving something like this around?" She shook her head and leaned in closer, her eyes constantly flicking between Ash's face and his crotch. "What do you think is going to happen? Seriously, now?"
"I…" Ash blushed, feeling himself getting very hard indeed, his dick straining against his pants as he stared down at her. "I can keep control." He didn't care for the questioning note that had ended on.
"Uh huh," Jessie said with a nod. "Sure you can. I'm going to help you keep control." She undid the button and pulled the zipper down, revealing the hard cock as it swung free. "Don't you worry, I know just how to handle this."
Then she kissed the head of Ash's dick. Ash made a squeaking sound and his eyes went wide as he felt the pressure of the lips. Her plump lips felt nice and her tongue flicking out to run along it made it even better. Ash took several deep breaths as he felt himself getting tended to like this, enjoying it all a ton as he kept on feeling her working along his shaft, going up and down, up and down, kissing and licking her way from the top to the base.
"Jessie," Ash moaned softly, staring down at the older woman as she worked. "This is- you don't need to do this."
"You want me to stop?" Jessie asked, lifting her eyebrows as she stared up at him. "You want to go meet June with a hard cock and full balls?" She gently squeezed the balls in question. "You know what will happen if you do."
Ash especially did now that Jessie had put the image of that in his mind. He swallowed hard as he pictured June leaning against a tree trunk, moaning sweetly as he ran his hands along her black skin, how her pussy would feel as he slid inside of her, how- okay, he really could not go and meet June like this!
"Fine," Ash squeaked. "Keep going. Just-!" He blushed hard as he tried to think of a way to put this that wouldn't sound really perverted. Absolutely nothing came to mind so he stayed silent and decided to just let her keep on going.
And Jessie most certainly could do that. She was starting to suck on his cock now and that was making him feel even better than before. He whimpered softly as he felt her lips forming a tight seal around his cock and her tongue lavishing attention on it as she sucked. She pushed herself down, down, down along the rod, all the way to the base. It seemed impossible that she could handle something like that but she clearly could and it made Ash feel great.
His hands were constantly opening and closing at his sides as he tried to think of something, anything that he could do right now other than just continue to stand here. Well, he could stare at Jessie's breasts. They looked really good from this angle. Really, really good. Big and… big and the way they pressed against each other like that, trapped inside of the top that Jessie was wearing… it was enough to make a guy swallow really hard and try to think of something else. Pretty much anything else, really.
Then Ash realized that he was getting a blowjob from Jessie. Staring at her amazingly large breasts was not the rudest thing that he could be doing right now! So he lowered his gaze back down to her breasts and looked at the large mounds, seeing how the pale boobs pressed against each other as Jessie kept on sliding her mouth up and down along his cock, over and over again.
Ash could remember a lot of what had happened on New Year's Eve but there was a pretty blurry filter over it all. He could generally remember how he had fucked Jessie on this very bed but the exact details of what he had done weren't nearly so clear. That was probably for the best. He couldn't remember Jessie sucking his cock any more than he could remember if he had ate her out but maybe it had happened.
Jessie was showing a lot of skill in this. Like she had a whole lot of practice in doing this sort of thing. Where had she learned how to do such a good job? And did Ash really want to know the answer to that, especially if Mom would come up anywhere in the conversation?
He quickly decided that no news was the best news and just focused on what Jessie was doing. Looking at her working her way along his cock, tending to it and making him feel so very, very good as she tended to him. He was as hard as a rock right now, his cock achingly stiff as he pressed inside of her mouth, his shaft fully erect as her tongue glided over it again and again.
And when she was all the way forward, when the tip of his cock pushed into her throat, Ash knew nothing like that had happened during New Year's Eve. He would have remembered that, just like he remembered, even through the fog, how it had felt when he had first slid inside of her pussy.
She was making some lewd sounds as she did this, a kind of gagging noise that Ash did find pretty hot on top of everything else. And with the pace that she was setting, she was making that sound a lot, constantly producing that kind of wet, gagging sound as she bobbed up and down, forcing her mouth all the way down to the base of Ash's cock before heading back up again. It was pretty erotic, especially when added to everything else that was going on right now and how good Ash was feeling as she kept on going and going.
Did Mom know about this? Ash had no idea which answer he would prefer to be the case there and just shook his head quickly as he did his best to dismiss the idea. No good answers there and he might as well just continue to enjoy what was happening to him as Jessie continued to bob up and down along his cock, again and again and again.
Jessie was setting a wonderfully quick pace, bobbing up and down along the cock again and again. She wasn't fucking her face along Ash's cock or anything but she certainly wasn't taking it slow and steady any more. And Ash was not complaining about that, either. He kept on smiling and staring down at Jessie as the older woman worked and worked and worked along his shaft. Every single stroke felt great and he could feel the bliss rising and rising inside of him as he got closer and closer. There was still a ways to go but that just meant that he could enjoy this even more, take even more pleasure from it all.
Ash really had no idea how long he was going to last for like this. He was just feeling so good right now, the sheer pleasure bubbling everywhere inside of himself, spreading out through every part of his body as he kept on getting sucked off. Part of him never wanted this to end, to keep on enjoying this pleasure for as long as he possibly could. The rest of him wanted to go ahead and cum, to shower Jessie with his load of semen or to fill her mouth up to the top with it. He really couldn't decide which would be better so Ash decided just not to make a choice and just let Jessie do what she wanted to do. Because Jessie most certainly knew what she was doing.
And she was enjoying doing it as well. Her hand had slid down between her legs and was pressing against her shorts, rubbing at the crotch. Ash couldn't actually see very much of that with the rest of her body (breasts) and her head in the way but just the knowledge that she was doing that was enough to make him feel awfully good about it.
Even better than awfully good, really. The pleasure was rising and rising inside of him, getting closer and closer to the surface and Ash couldn't think of any reason to deny it. Just let it continue, let himself continue to feel great from this and to finally get an orgasm from this. He took several deep breaths as he kept on staring down at Jessie working along his cock, stroking his balls as her lips glided along the shaft, down, down, down and then rising up until only the tip was left in her mouth.
"Jessie," Ash moaned softly, panting as he felt himself reaching the brink. "I can't hold back any longer. I'm going to cum."
Jessie seemed pleased to hear that. She made a humming sound around his cock and kept on sucking, her lips still forming a perfect seal around the cock as she glided up and down along it several more times, giving Ash the final bit of pleasure that he needed.
It felt good, of course, to cum. It felt really good and Ash moaned loudly as his hips twitched back and forth, driving his cock as deep into her mouth as he could manage, filling her up all the way. And then really filling her up as he started to cum.
His balls twitched and pulsed, emptying themselves upwards. His cock jerked inside of Jessie's mouth and Ash smiled from ear to ear as he felt the wonderful throbbing of an orgasm. Jessie had closed her eyes but she was still taking absolutely all of the load, letting Ash drain every single drop into her mouth.
And he did. It felt like a really, really large orgasm to Ash and he really enjoyed it, letting himself get swept away in the pleasure as he kept on cumming. Shot after shot of semen flooded Jessie's mouth, getting everywhere inside of her and completely covering her tongue. It was such an amazing feeling and it made Ash feel great.
He could feel Jessie's tongue moving even as he came, as the older woman swallowed the seed that he was filling her with and sending it on down to her stomach. That was a pretty hot thought as well and added a little bit of pleasure to everything else that Ash was feeling right now. He smiled and patted Jessie on the head, stroking her bright red hair as he felt his cock throbbing a bit more.
Finally, the orgasm came to end. Ash felt drained, like he had really unloaded everything that he possibly could into Jessie. And Jessie sure seemed to have zero complaints about how she had been treated. Her tongue was still moving back and forth along the cock even as it softened in her mouth, tending to it and making Ash feel some more wonderful shivers run through himself from head to toe. He liked that a lot and smiled as he kept on getting tended to, feeling the tip of the tongue doing what it could to coax out any cum that was still left in his balls.
There wasn't any more to give and after a bit, Jessie pulled backwards, her lips closing as she slipped free of Ash's cock. She tilted her head backwards and closed her eyes and then started to swallow. Ash watched in fascination as her throat worked several times, her face tight in concentration. Her hand had moved away from her crotch by this point but Ash liked the thought that she had been touching herself as she had worked. It was a very, very pleasant idea indeed and he just might have to give it some more thought later on.
For now, he just looked down at Jessie as she opened her mouth, showing off that she had indeed swallowed all of the cum that she had sucked out of Ash's cock. That was really hot and put him in a really great mood, plastering a nice, big smile on his face as he stared down at her. What a sight. What a great sight. That was something to remember in the future, even when he wasn't thinking about everything else that she had done.
There was probably something that should be said right now but Ash was just feeling too good to think of what it might be. Instead, he just stared down at Jessie some more, feeling this wonderfully warm, pulsing feeling deep in his body as he looked down at her. No, wait, there was one thing that seemed really fitting to say right now.
"Hey," Ash panted, feeling sweaty and sticky and quite, quite good. "Couldn't you have just given me some condoms?"