The True Endgame

Book 7: Chapter 12:

Once it came to stripping Cassandra, Ryouta felt himself more at ease. He might not have been in the usual body he used when it came to having sex, but now that he was actually stripping her, the process was the same. Something like that should have been obvious. Of course taking her clothes off would be the same whether it was in real life or in-game. Yet, he didn’t realize that it really would be the same until actually doing it. And because of that, he found himself feeling just a little bit more confident in what he was doing.

Unfortunately, no matter how many times he might have practiced before with her bras in real life, Ryouta still had no idea how to get her bra off without being extremely clumsy about it.

“Are you sure you don’t want me to do it?” Cassandra asked.

“I – I’m sure,” Ryouta answered as he sat on his knees behind her, his fingers fumbling around with the clasp of her bra.

“Are you sure that you’re sure?”

“No, but normal sure will have to be – there!” With a triumphant declaration, Ryouta successfully managed to unclasp Cassandra’s ball and was quick to pull it over her arms so that he could hold it up overhead as if it were a trophy.

Cassandra looked less than impressed with his bold display. “You’re lucky I love you.”

With a smile, Ryouta tossed aside the bra and brought his hands to the front of her body, allowing each of them to grope and knead her breasts. “I know. I don’t think that there’s anybody luckier than me.”

“Well… that’s debatable.”

“Is it?”

“Mhm.”

Ryouta placed a single kiss on side of her neck. “You’re not going to elaborate, are you?”

“Not at all.”

While he might have technically still been a virgin in real life, her breasts were anything but unfamiliar to his hands. Well, to more than his hands. His hands, mouth, and his tool were all more than experienced with her chest. Groping those heavy mounds, lifting them up, teasing their peaks – all of that was already natural to him despite the act of putting a condom on being something entirely foreign and uncomfortable.

“He-hey… shouldn’t we hurry up since we already put the condom on?” Cassandra asked, holding a moan back. “And the others are waiting…”

Ryouta kept one hand at her chest while his other hand slipped down into her panties, his fingers clumsily feeling around before finding her clit to focus on. “The more aroused you are, the less it’ll hurt, right? I think it works that way.”

“Is that seriously what you’re worried about?”

“Why wouldn’t I be? You’re my girlfriend and I love you. I want this to hurt as little as possible.”

“You know, it might not even hurt. Not every girl feels pain the first time.”

“Wait, really? I thought first times are supposed to be extremely painful for girls.”

“Yeah… no.”

A deep sigh of relief left Ryouta’s lips. “Hearing that makes me so much less nervous.”

Cassandra turned her body to the side, grabbed his head with a single hand, and pressed her lips against his. “Even if it wasn’t something you needed to worry about… thanks.”

“You’re insanely cute right now.”

“Shut up.”

Ryouta couldn’t help but to grin in response to that. “By the way, have I ever mentioned how amazing your boobs are?”

“A few times.”

“Dang. You don’t blush anymore when I say that.”

“You say it every single time you touch them. And a ton of times when you’re not touching them. What’d you expect?”

“So, in other words, I’m unoriginal.”

“You are, but I still love you.”

Ryouta gave her a playful pout. “I guess I’ll have to try to be original then.”

“You can try.”

Feeling challenged, he leaned in closer to her ear, his lips less than an inch away from them, and then… he pulled away. “I can’t. I was going to try to whisper something really cheesy and dirty, but I started to cringe just imagining myself saying it.”

Cassandra poked his forehead and then kissed his cheek. “You’re a dork. Don’t try to act different. All you need to do is be yourself.”

“You know, you’re actually pretty calm about all of this now. Was putting the condom on really the hardest part?”

“I’m forcing myself to stay as calm as possible. If I don’t… then it actually might end up hurting.”

“So wait, I do need to worry?”

“You don’t if you don’t talk about it and make me think about it.”

Taking a deep gulp, Ryouta tried his hardest to shake all of his worries out of his mind so that he could only focus on what was important. Right now, what was important was making sure that she was aroused. He already felt her getting wet with his fingers, but she wasn’t getting as excited as usual. That meant either he was performing worse than usual, which he wasn’t a fan of believing, or she really was more nervous than she was letting on now. If it was the latter, then it was time for him to bring out all the stops. Not to mention that said stops would also get him more excited and ready for it.

While he kept one hand at her chest and another against her crotch, his latest attack involved one of the first things he ever discovered about her.

Biting.

His head was already close to her neck, so he opened his mouth and sunk his teeth into the skin of her neck. He might not have had Fenrir’s fangs to bite deep into her neck—deeper than he probably ever should even in-game—but he was still able to bite her hard enough that she squirmed in a mixture of pleasure and pain. It was kind of ironic when he thought about it. In order to spare her from pain, he first had to cause pain.

And he was pretty confident that his plan was working seeing as how he felt her get even wetter as a result. He also found himself getting smacked on the forehead which told him that he bit her enough. “Sorry, was that too much?” he asked after pulling his mouth away from her now-bruised neck.

Cassandra reached up to touch at where he bit and recoiled as soon as her fingers touched the bruise. “I swear if this leaves a mark. What if Alice’s dad sees it?! Or the maids?! People on the plane and in the airport?!”

“They won’t be able to see it if you wear a sweater.”

“Sweaters aren’t the solution to every problem!”

“But they could be if you believe in the power of the sweaters.”

“No.”

“That was way too quick of a denial.”

“N-o. Was that slow enough?” Despite her sass, Cassandra looked happy. Peaceful, even. Sure, her neck still hurt because Ryouta bit her with the force that he would normally use in a video game where she only felt a very minimal amount of pain, but she was still smiling and had nothing but endearment in her eyes as she looked at him.

“I’ll try converting you some other time. For now, uh… do you think we’re ready?” Ryouta asked, looking at her much in the same way that she looked at him. She may have refused to join the cult of sweater worshippers that he so dearly wished to expand, but she was still the woman he loved with all his heart.

“I… think so.” She pulled his hand out from her panties and leaned back on the bed so that she could lift up her legs and pull the only remaining cloth on her off. With that, she was left totally bare and exposed to Ryouta. Neither nude around one another was another thing that neither of them were inexperienced with, including in real life. But now that they knew what was about to happen, it was impossible not to feel like this time was different.

Even so, neither of them intended on wasting the time nor arousal they had.

First, Ryouta reached behind her to grab one of Alice’s pillows so that he could pull it closer. “Lift your head for a moment,” he said. Once she did, he positioned the pillow directly underneath her head. “There. Is that better?”

In classic Cassandra fashion, her cheeks turned a shade of red from the thoughtful gesture. “You really do worry about things you don’t need to.”

“Hey, your neck health is important to me. Can’t have you hurting your neck when we’re only just beginning.”

Cassandra rolled her eyes before reached up to wrap her arms around Ryouta’s neck. “Whenever you’re ready… I’m ready”

“Alright. I’m gonna do it.”

“Don’t say it like that! That just makes me nervous.”

“What if I bite your neck while doing it?”

“I – that… well… if – if, and only if, you bite as low as you can so I can cover it up… fine.”

With permission for his plan, Ryouta brought his head back down to hers and didn’t waste any time in finding a good spot to bite. He bit her right where her neck met her shoulder, sinking his teeth into her skin to hopefully overwhelm her with pain and some pleasure so that she wouldn’t be stressed out and end up in even greater pain. Meanwhile, as his right arm worked on keeping himself propped up over her, his left hand reached down for his cock and took ahold of it. The condom was still on and he was still hard, so he had everything that he needed. Now, all he needed to do was position his crotch against hers and feel around.

Ryouta couldn’t exactly see what he was doing due to basically still having his face tucked against her neck, but he at least knew what he had to do. That involved grabbing his cock and aiming for her entrance. It was a different sensation than what he was used to with the condom on, but he did find her lower lips and knew that he was close. All he had to do after that was aim a bit lower since he already knew the real entrance was always a little bit lower than expected, get a bit of help from Cassandra in the form of her raising her hips for him to make penetration easier, and then… he did it. He finally did it. He slid his cock into her.

Going slow and carefully to make sure that she wouldn’t be in any pain, Ryouta pushed his cock into Cassandra and kept on going until he had a reaction from her.

And that reaction was feeling her drag her nails down his back with enough strength that he felt like she made him bleed.

Ryotua left his cock inside of her, but he let go of her neck with his teeth and brought his head up so that he could look down at her. “What’s wrong? Did that hurt?” he asked. Though, he didn’t even need to ask once he actually noticed her expression.

With tears forming at the corners of her eyes, Cassandra was clearly forcing herself to keep her mouth shut as she shook her head from side to side. “No-not at all.” Even when she talked, it was abundantly clear from her voice that she was in a great deal of pain.

“Sorry. Here, I’ll pull ou—”

Cassandra wrapped her legs around Ryouta’s waist. “Don’t you dare.”

“What? Why not? We can wait until the pain weras off.”

“Just… kiss me.”

Ryouta still planned on pulling out, but that didn’t stop him from doing as requested and kissing her. It was during the latest kiss, though, that Cassandra found the courage and determination to tighten the hug of her legs around his waist, pushing his cock even deeper into her until the entirety of his length was sheathed within her. A pained moan forced itself past her lips as her eyes rolled backward a little, her nails once more digging into Ryouta’s back.

“He-heh… there,” Cassandra said. “Con-congratulations on losing your virginity, you bastard.”

That was when it hit Ryouta. He finally, finally lost his virginity. After so damn long waiting and putting it off at every opportunity, always finding excuses due to all of his worries and insecurities… there he was. And to make it even better, he just got some highest quality tsundere fanservice in all of existence. He wasn’t even aware that such premium fanservice existed. “You’re the best, Cass Cass.”

“I – I know. Now… gi-give me a few minutes.”

“I can do that.”

Seeing as how Cassandra clearly had no intention of letting him pull out given the strength of her legs’ grip, Ryouta opted for kissing her to try and make her feel better. Whether it was kissing her lips, her nose, her cheeks, or her jaw or chin, he tried his best to make her feel better in what little ways that he could. He figured that this helped since the longer it went on for, the wider her smile grew and the less pained she looked.

“Alright… I think I’m ready,” Cassandra said.

“Are you sure?” Ryouta asked.

“Yeah. Just… you know, don’t be too rough.”

“I won’t. Promise.”

Cassandra loosened her legs around Ryouta so that he had enough space to do some of the work himself.

And now it was time for exactly that. Ryouta pulled his hips back just a little so that he could begin to pull his cock back, but he made sure that the top third of his length stayed inside of her and gently pushed right back into her with the rest of it. He wasn’t sure whether she was arching her back because of pain or pleasure, but he did know that he was grateful she switched to clutching the bed sheets instead of trying to dig through his back.

He sped up only a little over time. Cassandra’s comfort was his highest priority. Between frequently checking on her with whispered questions and making sure to watch her face, as embarrassing as that might have been to her, Ryouta never once sped up his movements without first being sure that she could handle it.

And handle it she did. Her back’s arching became almost entirely driven by pleasure as she grew accustomed to having his size inside of her. Sure, she was still uncomfortable, but she knew that wasn’t going to go away anytime soon – at least, she knew that it wasn’t going to go away soon during this first night. The majority of pain going away was good enough for her. Even so, she had an idea. “Bi-bite me more,” she whispered up to Ryouta.

Ryouta, who was practically lost in lust and was inspired with enough confidence to do anything at the moment, wasted no time in satisfying her request. He bit down on where her neck met her shoulder on the opposite side of where he last bit her, and he bit hard.

“Nngh!” A loud moan forced itself out of Cassandra. Fortunately, her idea worked just as she hoped it would. If there was only a minor amount of pain left, then that was pain which could easily be overwhelmed by a much more pleasurable variety of it. That made it far easier for her to focus solely on the pleasure. And when she was able to do that, she found herself steadily getting closer to an orgasm.

“I’m – I’m close,” Ryouta grunted out after pulling his mouth away from her.

Cassandra wasn’t about to try and talk since she knew that she would most likely make embarrassing noises if she did, so she nodded her head instead to let him know that it was alright.

Ryouta picked up on that but still tried to hold back for as long as possible. There was still a bit of hope inside of him that he would be able to make her orgasm before he did, though he knew just how unlikely that was given that it was their first time. Once he returned to biting her, though… he succeeded. He felt her entire body tremble underneath him. Her passage tightened around him just as her legs did, she arched her back and pushed her breasts up against his chest, and she pushed her head back against the pillow as she shut her eyes and tried her hardest not to let any noises out.

While Ryouta might have succeeded, Cassandra did not. Holding back the pleasured noises was simply impossible. They made sure to get out whether she approved or not, and those noises combined with the satisfaction of making her orgasm were enough to make Ryouta cum. Unfortunately for Cassandra, she wouldn’t get to feel him shoot it directly inside of her like she was so used to in-game, but Ryouta still got to feel all the usual pleasure as he pumped the condom full of his seed.

Once both of their orgasms were over, Ryouta relaxed on top of her, being careful not to put all of his weight on her, and there was no way that the idiotic grin stretching his lips would be going away anytime soon. “How – how was that?” he asked, already sounding out of breath.

“Didn’t… didn’t hurt at all,” Cassandra answered, also sounding out of breath.

“You’re a horrible liar.”

“Shush.”

Their lips found their way against each other once more and stayed like that for a few minutes. It was only when they remembered that they still had four girlfriends waiting for them that they finally broke the kiss and allowed Ryouta to pull out.

Ryouta went pale as soon as he looked down at the condom.

“What’s wrong?” Cassandra asked.

“I – I… I think it broke,” Ryouta answered.

Cassandra leaned up in an instant, which was something she regretted due to how sore she felt, and looked down at the condom. Her immediate reaction was panic as well but, given that she actually knew about her body, she relaxed right after. “Don’t worry about that. That’s normal.”

“It’s not normal for a condom to break!”

“It didn’t break, you dork. All that stuff is on the outside. It’s just… discharge. It’s normal. It doesn’t even look like actual cum.”

Hearing that calmed Ryouta down enough to properly examine the situation. He also did this by pinching the tip of the condom and rolling it around, feeling that his cum was trapped inside of it. “It’s even sticky,” he said after getting some of the white discharge on his fingers. He also ended up getting a bit of her blood on his fingers given that the condom had spots of blood mixed in with the discharge all over it. “I… I had no idea girls did this.”

“Please don’t describe it. I already feel embarrassed enough seeing that much of it.” She then looked down at the sheets and saw the combination of blood and wetness soaked into them. “Shit. I think that’s going to stain…”

“I doubt Alice is going to mind.”

“I mind! It’s embarrassing!”

Ryouta placed a hand on top of her head to pet her. Such an action would normally receive a flustered and cute response from her. Instead, Cassandra looked like she was about to kill him. “Wha-what’s wrong?”

“Is that the hand that you were just touching the condom with?”

He then realized what was wrong. He basically ended up wiping some of the bloodied discharge into her hair. “A-ah… sorry. I—”

“I’m going to kill you.”

“I’m just uh… going to go and get a wet towel, alright?”

Cassandra’s only response was to glare at him as he got up, went over to the private bathroom attached to Alice’s bedroom, and got a towel. Though, he did figure that he might as well take the condom off and throw it into the bathroom’s trash before returning back over to the bed with the towel.

That was when he noticed something. The side of the condom was torn. It wasn’t just his imagination, either. The side of it was actually torn open. Once again full of panic, he checked the condom out. Fortunately, the tear didn’t extend past his glans from what he could tell. It was nothing more than a scary reminder telling him to wear a properly fitting condom the next time seeing as how this one was clearly too tight if it ended up tearing.

Two back-to-back panics weren’t good for Ryouta’s heart. That was why, after tossing the condom in the trash and bringing a wet towel over to Cassandra to wipe her hair where he petted her, he flopped facedown onto the bed and sighed.

Sex was both far easier and far scarier than he ever imagined it being.

But he did finally have sex, and that made him proud.