Book 7: Chapter 11:

After a few more hours of fishing and relaxing together, Alice’s dad eventually returned with his friend and his truck to mark the end of their little fishing trip. Getting the boat back to the manor was much easier than taking it out to the lake seeing as how they actually had a proper transport for it this time around rather than have to rely on a golf cart that probably never should have been capable of pulling the boat in the first place.

As for any other fish they caught, all of the fish were released back into the water. There was no need for any of them to keep the fish they caught when William’s kitchen was more than stocked with enough food to last them all a considerable amount of time.

Having a fun time was more important than eating any of their catches. And as far as all the members of The Soaring Wolves were concerned, they had a great time. They finally got to meet each other in real life, had fun fishing together, spent hours simply relaxing under the sun on a boat in the middle of a private lake – they could not have asked for a better way to meet up and bond in real life. Well, some of them might have preferred if there were some fun drinks involved, but what they had was good enough.

They also took pictures of each other whenever any of them did catch a fish, so they still had immortal proof of their catches.

But as challenging as catching that massive carp might have been, there was a new challenge that Ryouta had to overcome. A challenge that he was worried about ever since he first started dating Serra and Cassandra. A challenge that always had more fuel added to its fire whenever Ryouta finally overcame one aspect of his worries, and now they were all coming back for one final showing.

First, he was afraid of accidentally getting his girlfriends pregnant. He didn’t feel ready to have sex in the real world yet. He didn’t believe that he was ready to be a father in case things didn’t go as planned.

Then there was the fact that simply so much time passed that he was worried about doing it in general. What if his girlfriends were already used to his avatar and his size? Ryouta was obviously smaller, both in general size and when it came to the equipment between his legs, than Fenrir was. Sure, he still did plenty of non-penetrative sexual things with his girlfriends in real life, but those were all things where size really didn’t matter. What if, when he tried to have actual sex with them, they were disappointed because of their experience with him as Fenrir?

And then he got more girlfriends. He didn’t feel like it would be right to lose his virginity with only some of his girlfriends and to take theirs while leaving the others out. He wanted to wait until everybody was together. He figured that was the fair thing to do and almost the more romantic thing to do. But now, because of that waiting… it meant that he would have to please five different women in the same night. While being a real-life virgin. How was he supposed to do that? Especially when he was already anxious about not being able to compare to Fenrir?

It seemed like everybody but him was looking forward to the night together with excitement, too. Sure, he was excited, but the mountain of stress on his shoulders prevented him from really getting excited about it. Normally, just the thought of getting to have sex with five beautiful women would have gotten him at least a little bit hard, but the anxiety overwhelmed whatever excitement he had.

That was the bad part about being the only man in their relationship. Being the only one with a dick might have been a massive ego booster to him, but it also meant that he practically had to do the jobs of five men. As a virgin. With women who he loved and thought were more beautiful than anybody else in the world.

Needless to say, the performance anxiety was real.

But if there was one thing that Ryouta learned after dating his girlfriends for so long and making the mistake of hiding his worries from them, it was that the most insanely idiotic thing he could do at the moment was to not confide in them. Before he met them, he would have tried his best to bottle everything up to force his way through his worries. Even while dating them, he made that mistake a few times.

Yet, time and time again, he was reminded of how foolish it was to do that. His girlfriends reminded him every single time his worries came to light that he was more than welcome to lean on them for their support.

That was why, no matter how harmful it was to his ego or the perception of his own masculinity, he made his decision.

He wasn’t going to simply bottle his fears up and hope that he would be fine. He wasn’t going to force himself to “man up” nor to view this as anything that had to do with being a real man. Instead, he chose to be… himself. He chose to simply be Ryouta, and Ryouta was a man who wanted to believe in his girlfriends. That was why, after dinner when they were all back in Alice’s room, he got his girlfriends together so that he could talk to them.

“What’s wrong?” Azalabulia asked, sitting behind the other girls on the bed.

“It’s… really embarrassing to admit,” Ryouta said, “but… I’m going to be honest. I’m kind of terrified.”

It was immediately to the others what he was talking about between the fact that they were talking about it and that there was nothing else they could imagine him being scared about. “I think we’re all at least a little bit anxious,” Eva said.

“I don’t suppose that you could grow a dick to help me out here, could you?”

“Sorry, that’s a bit beyond my abilities.”

“Is there anything in specific bothering you, my hero?” Alice asked.

“It’s just different in-game,” Ryouta said. “When I’m in FTO, I’m Fenrir. I’ve got my ideal body and… size. And I’m more confident in general. But here in real life, I feel like I’m a downgrade in basically every aspect. I’m worried about disappointing no matter how many times we’ve done it in-game.”

“I… don’t think you need to worry about that,” Azalabulia said. “I’m sure we all feel the same way to some degree.”

“Hey, I’m the only normal MMO player here. The rest of you are weirdos who made your in-game bodies close to your real ones.”

Cassandra pinched his cheek for that remark. “Don’t call us weirdos while we’re trying to support you.”

“But what if stupid humor at a time like this is my coping mechanism?” Ryouta pulled his cheek away from her.

A sigh slipped past Cassandra’s lips. “I don’t know what we can do to prove that your real body is even better other than by actually doing things. Even just doing what we usually do, I think that’s more fun than doing anything in game with our avatars. Right?”

Alice nodded in agreement. “Absolutely! Even if I can do more in-game due to having working legs and whatnot, I much prefer the fun we have had in reality with our true bodies.”

Cassandra looked at Serra next. Serra ended up getting lost during the conversation, though, so Cassandra had to repeat her question. Once Serra actually knew what the question was, she answered with text on her phone that read:

Yeah. Grinding and oral and all that is way more fun in real life than in-game. Also, your real dick is better than your avatar’s dick because it belongs to your real body instead of to a fake body. The real thing is always better than the fake thing. Would you like my real boobs less if I made my avatar’s boobs as huge as Aza’s?

Ryouta couldn’t help but to laugh at the comparison. “You’re right,” he said. “Thanks. Looking at it that way does make me feel better about it. And no, I’d love your real boobs more even if your made your in-game ones as big as Aza’s or bigger.”

“Wh-what?” Azalabulia asked, having no idea why her breasts were suddenly a part of the conversation.

Now that Serra gave her opinion on the matter, she scooted backward on the bed toward Azalabulia and sat herself on top of the larger woman’s lap, leaning her head against the front of Azalabulia’s chest as her hands reached up around their sides to squeeze and play with them. Azalabulia might have been curious about why her breasts were being talked about, but that curiosity was replaced by the flustering distraction of Serra groping her.

“Then… I guess we just have to figure out how to do this now,” Ryouta said.

“Is there really something else we have to figure out?” Eva asked.

“Yeah. How to start.”

“Oh! I know!” Alice said. “All of us can get into our lingerie while you are outside of the room, and then you can come into the room to the sight of us waiting for you on the bed!”

“That sounds like the ultimate harem dream, but… I think coming into the room and seeing five women on the bed waiting for me might be a bit too much for me to handle,” Ryouta said. “Like… I feel like that would probably put way too much pressure on me. Make me too anxious to actually do anything.”

“That is more than understandable, my hero,” Alice said. “Would it be better if we proceed simply as we are right now? Without having a grand reveal or anything of the sort? At the very least, I figure that if we simply get right into it, it would not seem like such a big deal.”

“I can only go one at a time. I… think I might get performance anxiety if it’s the first time and everybody else is waiting within sight.”

Before saying anything else, Alice reached forward, wrapped her arms around Ryouta, and pulled him in for a hug while setting the side of his head against the top of her breasts.

Ryouta might have enjoyed that sort of pampering, but he was still confused as for why he was suddenly receiving it. “What’s this for?”

“For being honest and trusting us enough to talk about this. Even with how much society has progressed in recent decades, I am aware that men still have so much pressure forced onto them when it comes to these matters. In addition to how much I appreciate your trust in us, I wish to reward your bravery as well!”

“I’m already afraid that I’m not being enough of a man right now, and now you’re going to make me cry.”

“Oh no, the love of my life, my hero, is going to cry! I will surely judge your character in a negative manner as a result of such a display of weakness.” Alice brought him off of her chest to instead hold him by his cheeks to position his face in front of hers. “If you cry, I will kiss each tear that visits your cheeks. And I will continue kissing you whether they stop or not. So please, my hero, if you wish to cry, then cry. I would never view you for the worse because of crying, nor would anybody else.”

“I know. It’s just that… I feel like now would be a really bad time to cry, but you make me happy and… secure enough that I want to cry.”

“Well, if you put it that way, then you are going to make me cry as well! I suppose we will all end up crying together at this rate.”

Ryouta shook his head before leaning forward just a bit more so that he could reach Alice’s lips with his own. “Thanks. And I love you.”

Alice’s lips curled into a smile. “I love you as well, my Ryouta.”

After a quick kiss, Ryouta had an idea. “I think I know how we can do this.”

“Oh?”

“If I do it alone with whoever’s first, I think I should be fine for everybody else to come join in after that. Though… it kind of makes me feel guilty doing it that way. I feel like then I’d be obligated to do it alone with everybody to make it fair, but I also want us to all be together during it. I mean, part of the reason we waited so long for this was so that we could do it in real life together. At the same time.”

“I can understand where you are coming from with that thought process. However, my hero, when it comes to situations such as this – it is impossible to truly be fair. After all, somebody will always have to come first while somebody else goes last. Even more important than that is that we are all comfortable, you included since you will be doing most of the work! If the options are to overwhelm you with pressure and stress, or to take it easy at the cost of being slightly less ‘fair,’ then I am sure we will all agree to the latter.”

“She’s right,” Eva said. “And honestly, it’s not that big of a deal. The plan is for the rest of us to join in after the first round basically, right?”

“Right,” Ryouta answered.

“And after you do it once in real life, there probably won’t be any problems in the future. Right?”

“Yeah. Well, I’m hoping so.”

“Then let’s do it that way. You’ll get some experience in with Cass and get over the initial anxiety since it’ll just be the two of you, and then you can feel like Mister Experienced while the rest of us are a bunch of awkward virgins. Anybody object?”

“I think that sounds like a wonderful plan!” Alice said.

Serra, who wasn’t able to keep up with everything being said, simply held up her phone with a message that told them she didn’t mind how they did things as long as things got done eventually.

Azalabulia was alright with it as well and she showed as much with a nod of her head.

Then there was Cassandra who remembered that she said she would be going first. “Ri-right… I – I did say I’d go first. Suddenly… I think I feel the same way he does. Doing it in-game is one thing, but with my real body… even if we’ve done things before, we’ve never actually—yeah. I think I’d rather it only be the two of us the first time, too.”

“Then it is settled!” Alice declared. “The rest of us will go wait in the guest room next to this one. Once you two are done, we will come back over and join in on the fun!” She was already trying to push the others out of her bedroom immediately after saying that. “The sooner we give them space, the sooner we will have our own turns!”

“Wait,” Ryouta said. “There’s one last thing, if I want to be completely honest with everybody.”

“You can tell us,” Azalabulia said.

“I’m… still afraid of accidentally getting one of you pregnant, but that’s… probably always going to be there until I’m ready to have a kid. It’s just that – what happens? I mean, I know that Eva got me condoms, and Cass is on the pill, but still. What if something happens?”

“Well, my hero, answer me this,” Alice spoke up. “If – and that is a very large if, one of us gets pregnant without planning for such an event, you would still love the child and wish to do your absolute best by them, yes?”

“Of course. I mean, I’m looking forward to having kids someday, just… maybe not right now. I think I want to enjoy a few more years of us all having fun together without having to plan around kids first. So yeah, I’d still love the kid as much as I would even if they were planned.”

“Then there is your answer. If one of us just so happens to – ah, wait. Allow me to rephrase this in a more appropriate manner.” Alice cleared her throat. “My hero, if you were to bless us with your divine seed to bestow upon us the greatest honor of carrying your child, then I am sure said child would be blessed with an incredibly happy and fulfilling life.”

Ryouta stared straight at her for a couple of seconds before laughing. “I’m ashamed of myself for how effective that was.” The other girls weren’t doing any better not laughing because of that either.

“She has a point,” Eva said. “Even if one of us gets pregnant… we all want kids. Maybe not right now, but any kid who does get born ahead of when we’re ready is still going to be loved and raised just like they were planned for all along, right?”

“Yeah. I feel way better about that now. That’s one of the perks about actually talking about something instead of trying to act like it’s not a problem.”

“Wow, who would have thought that talking about our problems can help fix them,” Cassandra teased. “But maybe that’s common sense to us and not you because we’re normal people instead of ‘normal MMO players.’”

“That’s bold teasing for somebody who’s about to get this dick.”

Cassandra’s eyes widened from the blunt and vulgar response, but she still smiled. “If – if you can say that, then it sounds like you’re ready for us to finally do this.”

“I agree!” Alice said, resuming her task of trying to push everybody else out of the room. Before anybody else could say anything, she already had them out of the room and closed the door behind her.

Only Ryouta and Cassandra were left.

And the two of them sat there on the bed together like a couple of awkward virgins who never even held hands before.

“This is… kind of funny,” Ryouta said. “I mean, how many times have we had sex in-game?”

“At least a few dozen times… probably,” Cassandra answered.

“And we do stuff together all the time in real life. Even stuff like clothed humping.”

“Ye-yeah?”

“That’s basically what we’re about to do, just with clothes in the way. But now this feels way more… serious.”

“We could… probably start with something we usually do. Like… I could give you… you know.”

“I’m tempted to take you up on that offer, but I’ve already got five of you I have to last through. If you do the usual, I’m going to want to cum from that, and I should probably save my stamina for the main show.”

“I guess, but… I could still do it just to get you hard.”

Ryouta grabbed Cassandra’s hand and pulled it down to his crotch. “Does that feel like a problem?”

A nervous smile stretched Cassandra’s lips, surrounded by her reddened cheeks. “So – so much for performance anxiety. By the way… this might sound weird, but, since you were being all honest with us… can – can I watch you put the condom on?”

“That’s not something I ever imagined somebody asking for, but I don ‘t see why not.”

“I’m just curious! Like… I’ve seen people practice putting them on bananas and stuff, but never a real dick. I don’t even understand it myself, I just want to see it.”

“Maybe you have a secret condom fetish that’s now awakening.”

Cassandra rolled her eyes.

Though, as soon as Ryouta asked his next question, her eyes looked interested rather than sarcastic. “Want to try putting it on for me?”

“Wait… can I?”

“Why not? If you’re curious about watching me put it on, I figure you might be curious about trying to put it on yourself.”

“I didn’t even think of that. So… yeah, I kind of want to try it.”

“Then wait right there,” Ryouta said and then got up from the bed to go over to the small bag that Eva took out earlier. It was the bag with all the different condoms in it. There were about three of each, and each set of three was for a different size, made of different materials, and also had different textures. He took this bag back over to the bed and set it down between them. “I… have no idea what size I should choose.”

“Large?”

“I appreciate the flattery but I think that might be a bit too much. They’re not supposed to be loose, and those would probably be loose.”

“But you’re… big.”

“Cass, I love you, and please never watch porn if you already think I’m big.”

Cassandra crossed her arms over her chest. “Hmph. I’ll have you know that I have watched porn before. That doesn’t change that you’re still big to me.”

“One, I love you. Two, I kind of want to try watching porn with you sometime. Three… if you really want to help me, go ‘hmph’ again.”

“Is this about tsundere fanservice?”

“Yes.”

“Then… hmph.” She looked down at his crotch. “It’s not like I want to help you or anything… you idiot.” And then she saw the pitched tent of his pants throb. “Se-seriously? You’re getting that worked up over something like this?” More throbbing. “You really are the worst…” And even more throbbing. Yet, with every throb, she found it harder to continue the act. Not only that… but seeing him react to her like that was just as exciting to her as her acting was to him. After how honest he was, openly talking to them all about his insecurities, she felt the need to reward him for that just like Alice did. Only, Cassandra had her own method of rewarding him that she knew he loved.

“Thanks, Cass Cass. You’re the be—”

“Shut up. I’m not doing this for you, so I don’t want to hear your praise.”

Ryouta was actually taken aback for a moment before he realized what she was doing.

She was giving him an overdose of the tsundere fanservice that he loved so much. Even though he didn’t have that talk with William yet about his honest feelings as part of the deal that he made with her, she was already going all in.

“Hurry up and take your pants off!” Cassandra said with a pout.

Ryouta was more than happy to oblige her, greeting her with an erect length that sprung out in anticipation as soon as it could.

“Wa-wait,” Cassandra said. “Doesn’t – doesn’t this thing look even bigger and harder than usual? A-and I’ve never seen it… move so much.”

“Do you understand the true power of tsundere fanservice now?” Ryouta asked. Out of everything that he had ever done in real life before with his girlfriends, he never felt hornier than he did right now.

Cassandra gulped and slowly reached her hands toward it. “H-how gross… getting this excited over… over…” She pulled her hands back to cover up her face. “I’m sorry, I can’t. Acting like that is way too embarrassing right now…”

Ryouta grabbed her by her wrists to pull her hands away from her face, allowing him to place his lips right against her own for a long, passionate kiss that she closed her eyes for. “It should be illegal to be as perfect as you.”

When she opened her eyes, she looked dazed as if she was confused why the kiss stopped. “But… I wasn’t able to do what you want.”

“You can try again some other time. Besides, you trying and then getting too embarrassed is just as good as you staying tsundere the whole time.” He lowered one of her hands down to his cock so that she could feel the living evidence of his statement. “Does it feel like I’m any less excited?”

“Seriously… this thing is going to break me if it’s this hyper. Wa-wait, did it just get even harder?! Why does it feel like it’s throbbing even more now?!”

“I guess because it can’t wait to break you,” he whispered into her ear, causing her to shiver and even let out a slight moan.

“I – I’m starting to think the performance anxiety was a scam.”

“Maybe it was. Maybe I was just trying to get you alone.”

“Mmnn…”

“Don’t you have a condom to be putting on for me?”

“Ye-yeah…”

Ryouta looked down at the bag and the first condom he spotted looked perfect. It advertised itself as a tight fit, and he was pretty sure that condoms were supposed to be tight, so he went with that one. “Then here. Use this one.” He placed the condom in her hand before scooting backwards and resting down against the bed with his hands behind his head.

“What – what do you think you’re doing getting all comfy like that?”

“I’m making it easier for you to get to my dick. Plus I want to be comfy while I enjoy the show of you putting it on.”

“Don’t you think you’re a bit too confident right now?”

“I promise you that the confidence is only an act to disguise the fact that my heart feels like it’s about to burst out of my chest at any second. Well, it’s fifty percent that and fifty percent pure arousal. It’s easier to be confident once extremely horny.”

“I feel like the opposite is true for me.” Cassandra sighed and tore open the condom packet. Next was actually trying to put said condom on. Positioning herself between his legs, she was still wearing her clothes from earlier in the day as she reached down with each of her hands. One hand wrapped its fingers around the base of his length to hold it steady while her other hand fiddled with the condom.

“Need help?” Ryouta asked.

“I – I can do this.”

“Do you know how to?”

“I’ve seen videos. When’s the last time you watched how to put one on properly?”

“That’s… a good point.”

Cassandra got back to work. Rather than hold onto his cock with one hand, she grabbed the ring of the condom with one hand while pulling on the tip of it to stretch it out a little. The ring looked thinner than he was thick, but it was also stretchy, so she didn’t worry about it and instead wrapped her fingers back around his cock with one hand as her other positioned the ring around the tip of his length. All she had to do then was “roll” it downward and that seemed to go pretty well. Though, it was stopped about two thirds of the way down his length and the ring seemed to be making an indent into his cock. “Is… this alright? I – I forget how far it’s supposed to go down and how to tell if it’s the right size.”

“I guess we probably should have paid more attention to sex ed. But I mean… it feels really tight, so it shouldn’t slip off. And there’s still space at the top, so it shouldn’t get ripped or anything.”

“Yeah. I… think that’s right.”

“You know, we sound like a couple of teens who never paid attention to school.”

Cassandra smiled and laughed a little. “Yeah, we kind of do.”

“Maybe that’s the secret to feeling young forever. If people in their fifties want to feel young again, all they have to do is have no idea whether a condom properly fits or not.”

“I’m not sure it’s that simple, but maybe you should let Eva know about that theory so that she can do some science. Have her fun around asking a bunch of people in their fifties if they know how condoms work or not and see if there’s a relation to how young they feel.”

“Pfftt. We’ll let her know later.”

“Yeah. So… now what?”

“Well, I have my dick out but the rest of my clothes on, and you still have all of your clothes on, so we should probably get naked.”

“That makes sense.”

“Something else that makes sense is, since I let you put my condom on, it would only be fair for me to take your clothes off for you, right?”

With a bit of a nervous blush once more coloring her cheeks, Cassandra nodded.