Your plan was going along swimmingly.
After Kris and Dess's previous rendezvous, something had definitely shifted between them. They still acted normal around others, still hung out with Asriel and Noelle and had fun like usual, but Dess tended to stick closer to Kris when she could get away with it, and Kris even ended up taking it easier on Noelle regarding pranks, just so Dess wouldn't get mad at him. It was odd, given everything you heard about Kris's past exploits, but it might end up being for the better.
Despite your slightly more direct involvement, Kris still had no idea you were there influencing him, which suited you just fine. You were slowly gaining a bit more of a hold over him, but you never took action with it, and thus he never noticed anything wrong.
It did lead to you discovering something useful, however.
Thanks to Ralsei, you found out very early in your efforts that you were able to "project" your focus to close friends of Kris if they were nearby, without actively leaving Kris's body. And sure enough, after their first sinful activity together, Dess was now considered close enough to him that you could faintly feel her essence when she was close, a subtle tug that you could observe her instead of Kris should you wish.
And that opportunity came quite soon, during an average day at the Holiday household. Kris and Noelle were in her room, playing video games, while Dess and Asriel went to her room to do homework. All it took was a small bit of focus, and you wondered what they were up to...
It worked flawlessly. Kris blinked, and the next thing you knew you were looking into Dess's room, as if you were a fly on the wall. Asriel was looking over the homework they had, while Dess was next to him, idly strumming her guitar. In hindsight, you should've expected that he'd be the brains between the two of them.
"You sure you already understand all this?" Asriel asked. "You know Gerson isn't gonna cut you slack just because you were suspended."
Dess rolled her eyes. "I got it, dude, don't worry. I'm only trying to pass, not ace the whole thing." As she turned back to her guitar, you could overhear some of her surface level thoughts. "(Everyone knows Elly is the smarter Holiday kid, anyway...)"
Asriel chuckled nervously. "Come on, Dess, don't you want to be a better role model for Kris and Noelle?"
Dess winced as she played a wrong note at his words. "Oh, come on, Azzy, I'm no role model. You're the golden child."
"Please, I've seen the way both of them look up to you." He leaned back in his chair. "Sure, I get good grades and all that, but you're the cool one. Kris especially keeps trying to do the things you do. The other day, I caught him looking up guitar lessons on the internet."
It did surprise you when that happened. You knew the piano was always Kris's instrument of choice, it's why he didn't hesitate to give you full reign on playing guitar those times it came up in the dark world. If he was looking into it on his own, it was a definite sign that you had already shifted the course of his life, even if in a minor way thus far. You weren't sure how to feel about that yet.
Dess seemed equally confused. "(Guitar? Huh, help him cum one time, and he starts trying to copy me...)" She smirked as she pushed the thought aside. "Well, no reason he can't branch out a bit, musically. Might be good for him."
She glanced at her phone, then jumped up in a mild panic. "Shit, forgot I had band practice today, I gotta go get ready." She put her guitar down and grabbed up some clothes. "You can finish this right Azzy? Thanks!"
Dess rushed out of the room before he could respond. Your phantom presence followed her as she ran to the bathroom and quickly stripped down and got into the shower. You weren't expecting your voyeurism to go this direction, but you weren't really complaining either.
...a troubling thought occurs to you after you catch yourself simply watching the water cascade down Dess's nude body. You're not sure if you're being influenced by Kris, or if the feelings are your own, but... you think you're beginning to develop an attraction to this doe.
You release your focus. Just like that, you're back with Kris, who was completely oblivious to the return of your conscious presence.
This wasn't part of the plan. You'll have to keep yourself in check if you want this idea of yours to work.
The next day was a weekend, and since Kris and Asriel didn't have any homework to do, they naturally decided to stay home and play video games. Dess and Noelle joined them before long, and after Toriel left to do more administrative school stuff, it was just the four of them in the house, crowded around the TV, taunting and yelling about matches in Super Smashing Fighters, just like old times.
Still, it was impossible for Kris to avoid those charged feelings forever. He was next to Dess on the couch, while Asriel and Noelle both sat on the floor in front of them. It was the same seating arrangement they had for years, but now it provided them with certain opportunities.
Dess was the first one out, leaving Kris to fend for himself in-game as Asriel and Noelle both (correctly) assumed he was the greater threat. Kris was so focused on the game that he nearly leaped off the couch in surprise when he felt Dess's hand gently caress his thigh.
He shot her a worried glance, but was only met with a very smug smile, before he turned back to the game. If she thought she could use this as a new way to tease him and throw him off his game, he'd do his best to hold on.
Despite the warmth in his cheeks and the growing tightness in his pants thanks to her touching, Kris managed to keep his focus, and came out on top. Dess immediately pulled back to join back in the trash talk, like nothing happened. Kris was just thankful that, when Asriel and Noelle turned around to playfully accuse him of cheating, he was sitting in such a way that his erection was completely obscured.
Still, the damage had been done, and when the next round started, Kris couldn't stop his mind from wandering to all kinds of lewd things with Dess, and that combined with the other three focusing him down first meant he was eliminated before anyone else.
Kris sat back and complained about it, but still laughed. It was all part of the fun. Though now that he was out...
He glanced over at Dess, who was leaning forward, fully focused on redeeming herself. Kris made sure the other two were doing the same, and decided to retaliate.
He copied Dess's earlier motion and grazed a hand against her thigh, barely touching her fur from where her shorts cut off. Dess stiffened at the touch, then shot Kris a playful glare. She turned back to the game, but made no move to stop Kris, so he kept going, fondling her leg, running a hand up her shorts to feel even higher on her thigh, and at one point he even got bold enough to reach up and grab one of her breasts.
This made her involuntarily hiss, though it was easy to play off since she died in game at the same time. Now that she was out, too, while Asriel and Noelle duked it out, she intercepted Kris's hand and leaned towards him to whisper directly into his ear.
"Such a naughty boy, Kris... But I guess I did start it..."
She held his hand to her breast, so he continued to lightly squeeze her through her shirt, forcing her to bite her lip to not let out a moan. At the same time, she ran a hand over his bulge, causing him to tense up and stifle a gasp as well.
They both knew how dangerous this was, touching each other only a couple feet away from both of their siblings, but neither of them could bring themselves to stop, either.
Their mutual molestation was interrupted by a cheer from Noelle, and they both disengaged to lean forward and watch. The younger Holiday had just managed to clutch out a win over Asriel, who looked to still be in shock about... whatever happened.
Dess laughed loudly. "Atta girl, Elly! Kick his ass!"
Asriel huffed and rolled his eyes. "She got lucky."
"Nuh uh! I beat you, Azzy!"
Noelle's taunts got more smiles and laughs from them, but as they went to set up another round, Asriel checked his phone, then bolted to his feet.
"Crap, I forgot I have work today. Sorry, I gotta go!"
He rushed up to his room and quickly returned with his backpack, containing his uniform and the like, and bolted out the door.
"Damn, didn't even get to make fun of him," Dess lamented. "Oh well, I can do that later." She took the time to check her phone as well, then glanced down at Noelle. "Actually, don't you have a doctor's appointment soon, too, Elly?"
Noelle gasped and stood up. "You're right! I gotta get home so Mom can take me there!" She quickly rushed over and hugged both Dess and Kris in turn. "Bye guys! See you later!"
Then she also ran out of the house, leaving the young human and the teenage doe fully alone.
For how long, they weren't sure, but they weren't interested in weighing up risks at the moment as their lips crashed into each other the moment the door shut behind Noelle.
By now, Kris was beginning to do a decent job keeping up with her in their makeout sessions, and pressed against her body with an equal amount of need.
Eventually, they needed to breathe, so Dess pulled away first, her eyes clouded with pure lust. "Your room. Now. I got some lessons I want to teach you..."
Kris obliged with not a hint of hesitation, and practically rushed her upstairs. They barely got the door closed behind them before they started kissing again, but Dess pushed him away after a moment.
"Remember when I said you'd be learning how to go down on me?" She smiled as she began to work her shorts down. "Now's your chance."
Kris swallowed nervously and nodded. This pleased Dess, so she took a seat on his bed, then spread her legs to show her bare crotch. Kris had seen it before in their previous sessions, but this was the first time he had seen it so directly, with Dess presenting herself.
He felt an urge to lean into it, but hesitated. He knew what she wanted him to do, he had seen enough porn, but he wasn't exactly sure how to do it. Still, he knew he couldn't just sit there and stare, so he took a deep breath and decided to dive in and wing it.
You took over from there and made Kris move his tongue in just the right ways.
Dess moaned out loud as Kris began to lick at her folds, surprised at just how eager he was. She had expected to walk him through it, show him where her clit was and all that, but he was dominating her with skill that he shouldn't have had. He was a born natural at this.
Kris accepted the autopilot he had been sent on, and simply reveled in the noises and moans he got from Dess. That must've meant he was doing a good job, so he kept going, his tongue guided by some strange instinct within him. Dess's hands gripped his hair as he ate her out, bucking her hips as she neared her peak.
She wasn't even able to say anything as her orgasm crashed over her, causing her to buck her hips up into Kris's face as she cried out wordlessly. She only let him go as her hips stopped twitching.
Kris pulled back, panting, his face nearly completely coated in her juices. He smiled up at her, and Dess felt that heat within her grow tenfold at the sight.
She needed him, now. Toriel herself could come through that door and it wouldn't stop her.
Dess pulled Kris up to kiss him, not caring about her own fluids. She pulled back, a few stray strands connecting their faces, and grinned lecherously. "Damn good job, Kris. Where'd you learn to do that?"
Kris genuinely had no idea, so he just shrugged. "Just kinda... did what came natural, I guess."
"Well, keep that up, and you'll have every girl in Hometown lining up for you." It was a light jest, but even as she said it, Dess felt a small pang of... something at the idea. Jealousy?
She checked her phone. They still had about an hour before Toriel would be back from work. She wouldn't be cock blocked by a surprise family arrival again; now was the time.
She set her phone aside and kissed Kris again, more gently than before. "Now, Kris, tell me... want to learn what sex feels like?"
Kris is eager to say that he is, but you beat him to it. "Fuck yes I do."
Dess couldn't help but shiver at Kris's voice. Since when did he learn to talk sexy like that, too?
Kris, meanwhile, was surprised momentarily. He was pretty sure he didn't mean to say that... but the sight of a pantsless Dess reaching for his shorts knocked him out of his thoughts.
He had more important things to worry about right now.
Kris hurriedly shed his pants, then climbed on top of Dess, the same way he'd seen in videos online. It took some guiding from Dess, but eventually he was able to line up his cock with her entrance, and with one more kiss, she pulled him inside.
Once again, Kris could feel himself practically black out from sheer pleasure, while Dess arched her back and moaned loudly. He was stretching her just a bit more than she thought he would, not that she was complaining.
She just let Kris lay there on top of her for a moment, basking in the sensation of losing his virginity, when suddenly her phone buzzed from next to her head.
Their hearts stopped, and Dess felt her stomach do backflips when she picked it up and saw that it was Mom. Still, Kris seemed too frozen in both panic and pleasure to do anything, so she just motioned for him to stay still and quiet while she answered. She knew better than to leave Mom unanswered.
"H-hey, Mom," Dess greeted, trying to sound like she didn't have her younger pseudo-brother's cock inside her. "What's up?"
"December, are you home right now?"
She glanced down at Kris. "No, I'm over at the Dreemurr's right now, watching Kris."
"Hmm, that works, then. I have to leave Noelle at the doctor to tend to some business in the office, do you think you could go walk her home when she's finished in about half an hour?"
Kris knew he should listen to Dess, stay put while she was on the phone with Carol, but part of him was very, very tempted to start trying to move his hips, now that his mind had just begun to process the feeling of her tight walls squeezing him.
You made him rock back and forth before he realized what was happening.
Dess hissed as Kris began to move again, and shot him a glare. "Y-yeah, Mom, that- that sounds good."
"Is everything alright, December? You sound winded."
Kris pushed his hips against hers again, and Dess had to bite her lip to keep from moaning directly into the phone. "Fff... Yeah, I'm fine, Mom, just, mmm, beating Kris at- at video games right now."
"...I see. Just make sure you both keep up with homework, too, okay?"
"Sure thing, Mom, love you!"
The moment Carol said her goodbyes and hung up, Dess tossed her phone away and smacked Kris on his head. "The fuck are you doing? She nearly heard us!"
Kris just increased the speed of his hips now that she wasn't on the phone anymore, and Dess had a hard time staying angry under the sensation of the small human fucking her.
The reality of the situation sank in as she thought that. Kris was fucking her. Kris was fucking her. Kris was fucking her.
Every part of her brain knew this was a bad thing, that she should feel ashamed, that she'd be in so much goddamn trouble if anyone ever found out... But she couldn't stop. She wanted this. And judging by how eagerly Kris was thrusting, he wanted it, too.
This wasn't just a teaching opportunity, anymore. They both knew this. And clearly Kris had already thrown caution to the wind to stop pretending. So, pulling her legs up to wrap around Kris and keep him from even thinking about pulling out, Dess did the same.
She could tell he was close, the way his breathing got harder and his movements more erratic. She just leaned down and whispered into his ear to give him that last push he needed.
"Cum inside me, Krismas..."
You hold Kris's hips as deep as possible as he came. He buried his face into her breasts, moaning as Dess managed to make him once again cum harder than he ever had before.
As she felt his hot seed fill her up, a stray thought in the back of Dess's mind panicked about the consequences of letting him do this. But she shoved the thought aside for now. That was a problem for future-Dess to figure out.
Kris, meanwhile, was lost in bliss. He just had sex, and it felt just as good as what he heard online. The fact that Dess let him do this, and seemed just as excited about it, made him feel... warm, inside, in a way he couldn't quite place, but it felt very nice. You mirrored his feelings.
Once he recovered enough to become lucid again, Kris slowly pulled out, and was left captivated by the sight of his cum dripping out of Dess's pussy. He didn't get to enjoy it for long, though, since she quickly covered herself and grabbed some paper towels she brought up with them to clean up. Kris didn't even remember seeing her grab them, but then again, he wasn't really paying attention while they went upstairs.
Kris wanted to go again right away, which he signaled by kissing Dess passionately, but she just pushed him off after a moment as she reached for her shorts.
"Nope, that's all we have time for right now," she said. "We gotta go pick up Elly from the doctor."
Kris pouted, but nodded and also got dressed. "When... when can we do that again?"
Dess's breath hitched. Even though she had fully given into the pleasure in the moment, she hadn't really thought ahead on how to answer a question like that. "We'll... have to see, Kris. I'll let you know when it's time, okay?"
He nodded, but she could see the slight disappointment in his eyes. She was disappointed, too, but that was the reality of their situation. They just had to continue acting normal around everyone else, and only act on their feelings once they had a moment to themselves.
After a quick trip to the bathroom to freshen up and not smell like sex, the two of them set out for the hospital to pick up Noelle. It wasn't long before her and Kris got up to their usual antics and childish conversations, leaving Dess to simply watch and smile, her mind a tempest of conflicting thoughts.
Kris and Noelle really did get along well... before, she could've easily seen the two of them dating later and life, and she would've been more than happy to cheer them on, but now...
...Dess wasn't sure how to feel. Part of her wanted to be possessive, to keep Kris all to herself, but another part of her knew that what they had was absolutely not sustainable, and would only raise the chances of them both getting in massive trouble the longer it went on. Not to mention how much it would hurt both Elly and Azzy if they found out...
She sighed as Kris picked up a stick with a bug on the end and teased Noelle with it. These were all questions that future-Dess would have to answer.
...I SEE.
YOU HAVE DEVELOPED A PARTICULAR INVESTMENT IN THIS OUTCOME.
VERY, VERY INTERESTING...
I HOPE YOU WILL NOT COME TO REGRET SUCH FEELINGS