Volume 7 Chapter 33 The Final Night*
Edited by: Kanaa-senpai
It was going to be a late one…
The long expedition was finally ending tomorrow, which meant tonight was my last night with Cassandra. Though it had been a short trip, I’d actually spent more nights with her than anyone besides Regina-san or Ilse.
She had been incredibly reluctant at first, but she’d gradually softened her stance. By last night, I felt like she had finally started to accept me.
I’d reached my minimum target, but I really wanted something more—something more “lovey-dovey.” I wanted Cassandra to be the one coming onto me. I wanted her to truly be my lover. Considering the Ordeal¹ and her prickly personality, it was probably a greedy wish, but we had already cleared the steepest hurdles. This one night would be the final showdown to see if I could actually capture her heart.
(First, the shower,) I thought.
”Yeah,” she replied.
After we finished eating, the two of us headed into the short-stay inn I’d secured. Cassandra didn’t seem particularly shy or hesitant; she just gave me her usual straightforward responses. Come to think of it, I’d never actually seen her look embarrassed. While the idea of a flustered Cassandra was a huge turn-on, this stoic side was just part of who she was.
”Cassandra, I have a request. Will you hear me out?”
”…As long as it’s within my power,” she said.
She had mellowed out so much that she gave me a positive answer before even hearing the details. Of course it was within her power. It might be a little embarrassing for her, but we were alone in this room. There was a good chance she’d accept.
”We’ve finally managed to get close, so I was thinking… I’d like us to act like actual lovers tonight.”
”…Even if you say ‘lovers,’ I have no experience. I won’t be very good at it,” Cassandra replied.
”You don’t have to be good at it. Just… try to act out the image of what it would be like if you actually had a boyfriend.”
This was my secret plan to win her over: Lover Roleplay. If this made her think, (Being in a relationship is actually pretty nice,) then I’d win. Just as she said, it seemed she had never had a lover before. She had been so focused on her work that she’d never even considered it.
Based on her current Affection Level, she wasn’t exactly head-over-heels for me yet, so the push had to come from my side. But I wanted her to start looking at our relationship in a positive light. It would be lonely if it was just “mission over, goodbye.”
”…I will do my best. But what exactly does someone ‘acting like a lover’ do?”
”Thanks. Well, I want you to think of the specifics, but I think lovers generally crave one another. Don’t overthink it, though. For starters… let’s try a kiss.”
”…Fine,” she said.
She had a serious, almost pained look on her face, but she was going to go through with it. We’d done it countless times on the bed, but we had never shared a kiss while just standing there. The order of operations was completely backward, but that didn’t matter. I just wanted to enjoy her.
Standing face-to-face, I pulled her close. Cassandra slowly closed her eyes, and I pressed my lips to hers. She actually hugged me back. Her core was solid—the undeniable physique of a veteran Knight—but her breasts were incredibly soft as they were crushed against my chest.
We started with light, pecking kisses, which gradually evolved into a passionate exchange of tongues. We’d done this enough that we weren’t clashing teeth anymore.
”I tried to make that feel like a kiss between normal lovers. How was it?”
”…How am I supposed to answer that?” Cassandra asked.
”Did you feel… I don’t know, a sense of calm? Or maybe your heart racing? Did you feel anything like that?”
”…I suppose. I might have felt a little bit of that.”
She wouldn’t give me a straight answer, but her cheeks were flushed. Her heart was definitely pounding. She probably associated kissing with the intense pleasure of the bed, considering every time we’d kissed before, it was coupled with extreme ecstasy.
”Let’s head to the shower.”
”Understood.”
I couldn’t just jump straight into the main event; we needed to clean up. I’d had a mock battle with Captain Emily earlier today, and though I wasn’t filthy, I wanted to be fresh. I washed myself quickly and then invited Cassandra in. I had her sit on a stool and started washing her hair for her.
”Cassandra, any itchy spots?”
”No, I’m fine,” she said.
Once I finished with her hair, I moved to her body. While soaping her up, I let my foam-covered hands wander to her breasts, kneading them lightly.
”Ah… ♡ Are you planning to do it here today?”
”No, not yet. I’m just teasing you a little.”
”I see… Nn… ♡”
Her breasts were large and soft, and they felt incredible to massage. I wanted to keep going forever, but I held back. I gave her “secret garden” a very brief caress before finishing the shower.
Cassandra mentioned she wanted to groom her pubic hair, so I stepped out first. I waited for her in a gown rather than standing there naked. I was glad she was taking care of it, though I found myself wishing I’d suggested a “Shaving Play” scenario. Maybe it was still too early for that?
”Sorry to keep you waiting,” she said.
”It’s fine. Let’s start over here. Come here, Cassandra.”
”Yeah.”
I wanted to use a massage to lead into the foreplay, so I put off the heavy stuff for a moment. I pulled her close, just enjoying a moment of stillness. We didn’t speak; just feeling each other’s body heat through our skin was enough to relax us both.
”This isn’t so bad, right?”
”…No. It’s not bad at all,” she said.
Maybe because she was conscious of the Lover Roleplay, her tone was much softer. She seemed genuinely relaxed.
”Alright, time for the massage.”
”Yes.”
Since this was our last night, I was going to use this massage to slowly, meticulously build her up. I didn’t need to do this to enjoy her, but it was all part of the play.
I used rose-scented oil, tracing my fingers over her neck, her collarbones, and the sensitive tips of her breasts. While I was technically giving her a massage, I was mostly enjoying the way her soft flesh shifted and molded under my touch.
”Nn… ♡ Ah… ♡”
As I kneaded them gently, her n**ples reacted, budding and hardening. I wondered if she was enjoying this as much as I was. I made sure to give them my undivided attention. Slowly. Carefully. Leaving no part untouched. Using every trick I knew.
”Nn… ♡ Today… ♡ You’re being even more… thorough… ♡ than usual… ♡”
”Well, if we’re lovers, I want my partner to feel as good as possible.”
”I see… ♡ Haa… ♡ Hah… ♡”
Cassandra wasn’t frigid by nature. If you stimulated her correctly, she felt everything, and she got wet. Over the last few days, her body had become perfectly tuned to me; her sensitivity had skyrocketed, and her v**ina was already yielding and loose.
It helped that any soreness was instantly fixed with Healing Magic². Her breath hitched, her cheeks stained a deep scarlet, and her body jumped every time I rolled or pinched her n**ples. It was incredibly erotic.
”Cassandra…”
”Nn… ♡”
I couldn’t help myself. I leaned in for a kiss, and it turned deep instantly. The usually untouchable Knight was now radiating a lewd aura, her tongue tangling with mine.
Just like with her breasts, I took my time exploring the inside of her mouth. The mouth is an erogenous zone too, and the way she twitched ever so slightly was just too cute.
”A massage like this isn’t bad either, is it?”
”…If it’s between lovers… I suppose this is fine too… ♡”
”Then that means right now, it’s ‘not bad’?”
”…Yeah… ♡”
When I pulled back and asked her, she gave me a much better answer than I expected. Maybe I’d teased her so much she was getting impatient.
”Alright, let’s continue the massage. Open your legs a bit.”
”……”
She silently moved her legs. As expected, her private parts were already glistening, slick with an overflow of nectar. I didn’t say anything as tacky as pointing it out; I just started caressing her slowly, starting from the outside.
”Nn… ♡ Right there… ♡”
At this point, “massage” was just a label. This was pure foreplay. Cassandra was beginning to mutter, her voice practically begging for more pleasure. It was time to move to the next stage.
”Okay, massage is over. Now it’s my turn to enjoy myself.”
”Yes… ♡ If we’re lovers… then we do it… ‘together,’ right?”
She was really trying to wrap her head around the whole “lover” concept. Things were going great. I told her I was going to enjoy myself, but I stayed focused on her for a bit longer. I knew it wouldn’t hurt her if I just went in, but I wanted to do this right.
Slurp…
”Ah… ♡ You really do… love my breasts, don’t you?”
”You’re attractive everywhere, Cassandra. I can’t help it.”
”Hmph… I don’t see what’s so special about them… ♡”
Her words were her usual self, but her eyes were hazy with lust. I took one n**ple into my mouth, licking and suckling, occasionally giving it a playful little nip.
With my other hand, I teased the other n**ple—flicking it, squashing it, and rubbing the areola. Her favorite was when I pulled and stroked them simultaneously, so I made sure to mix up the sensations to keep her on the edge.
”Nnn… ♡ Nothing but my breasts… ♡”
She sounded like she wanted more attention elsewhere, so I used my free hand to roam over her neck, ears, and ribs. None of these spots would make her climax on their own, but when layered with everything else, they were devastating.
”Ah… ♡ Kuu… ♡ I’m… I’m going… ♡”
The build-up from the massage had been so thorough that she reached a light climax just from that.
”Nfu… ♡ Making me go all by myself… isn’t fair.”
”Is that so? I’m having a great time just watching you, so I don’t see the problem.”
”Right… I forgot… what kind of man you are.”
She looked at me with that familiar exasperated expression. Was I being treated like a total deviant? Probably. I moved my tongue down to her flower. She was already soaked, but I didn’t care; I latched onto her clitoris.
”Ah… ♡ So suddenly… ♡”
The wet, sucking sound of me latched onto her was one of her favorites. To match the rhythm, I slid my fingers inside her, stroking the v**inal walls. The inside was a swamp of thick, syrupy fluids, making a messy, squelching sound every time my fingers moved in and out. I was pinned between her muscular thighs as her hips writhed to escape the sensation, and I savored every sweet moan she let out.
”Again… ♡ I’m going… ♡ Ahhh… ♡”
This time, the dual stimulation of the clit and her insides sent her over the edge. She clamped down on my fingers with incredible force—a testament to her physical training.
”Haa… ♡ Haa… ♡ Are we… still doing more?”
”No, I’m finally going to put it in.”
Cassandra asked me with a bright red face, having already climaxed twice. Her ragged breathing, messy hair, flushed cheeks, and moist, pleading eyes… she probably didn’t realize it, but she looked incredibly sexy.
Since the foreplay was more than sufficient, it was time for insertion. I had her hold her own legs back, aimed, and thrust my hips forward. I was swallowed up smoothly.
”Fu… ♡”
”Man… Cassandra, you’re way too hot like this.”
”What are you saying… ♡ This is only because… you toyed with me so much… ♡”
”Maybe, but you’re still the best.”
”Hmph… ♡”
She looked away, but when I started grinding my hips while buried deep inside, licking her Portio with the head of my member, she melted instantly. But the way her walls were pulsing and squeezing me… I felt like I was the one about to lose it. I’d been holding back for so long, after all.
”Ah… ♡ Not there… that’s my weak spot… ♡”
”I know. That’s why you love it, right?”
”Kuu… ♡ You pervert… ♡”
I wasn’t even doing anything that perverted, but she clearly didn’t like being the only one at the mercy of pleasure. Maybe her pride would be appeased if I joined her. I shifted positions into a Seed-Planting Press³, prioritizing my own release.
I lowered my weight onto her and pumped my hips; the room filled with the rhythmic slapping of skin and the wet sounds of stirring her insides. Her sweet voice in my ear and her face twisted in ecstasy pushed me over the edge.
”Cassandra, I’m coming. Ungh…!”
”Ah, ah, ah, ah… ♡ Daisuke… ♡ Ah! Kuu! Nnn… ♡”
I surrendered to the mounting pressure and poured everything into Cassandra’s womb. Her body spasmed in sync with the pulsing of my release; it looked like we’d managed to finish together.
She looked like she was waiting for a kiss, so I leaned in. This time, she was the one who reached out, pulling me into a deep, active kiss. Now this felt like lovers.
”I’m really happy you came to me first, Cassandra.”
”Only… because we’re ‘lovers’ right now… ♡”
So it was a limited-time offer. That was a shame. But we were just getting started. Thanks to my Insatiable Skills, we could do this all night. Up until now, we’d mostly stuck to doggy-style or missionary—positions where I did all the work. I didn’t think she was ready for Cowgirl yet, but maybe a seated face-to-face position?
”Let’s change things up. Just hold onto me.”
”Okay. …Haaa… ♡ This is… so deep… ♡”
I sat up while still inside her and lifted her into my lap. Cassandra gasped, surprised by how much deeper I sank into her due to her own body weight.
As her womb was pushed upward, her v**ina squeezed me tight with a slurp-squelch sound, and a mixture of her juices and my s**men came gushing out of the gap where we were joined.
”In this position, you can control the rhythm a bit, but I’ll support you for now.”
”Uu… ♡ I, I understand… ♡”
I didn’t know exactly what it felt like to be skewered like that, but the stimulation was clearly intense for her. I held her soft buttocks as she began to slowly move up and down, enjoying the way her breasts swayed and her internal grip tightened.
”Nn… ♡ Fu… ♡ Fu… ♡ Fu… ♡ How’s this? Is this… okay? … ♡”
”Yeah, it feels amazing.”
She started with a simple vertical motion, but soon she started grinding her hips. It looked like she’d found her own sweet spot and was leaning into it. She loved it when I hit the very back, so every time she dropped her weight down deep, she’d shiver. She was having mini-orgasms one after another.
”You’re getting good at this. You really are incredible, Cassandra.”
”Nn… ♡ Stop praising me for… something like this… Uu… ♡”
”It’s true that I didn’t start liking you just because of your body, but if we’re lovers, having good compatibility is a great thing, right? I want to kiss my ‘lover’ while we do this.”
”You’re a hopeless man… Nn… ♡”
Her words were a rejection, but her body was honest; the moment we kissed, her insides clamped down in joy. We stayed connected in a deep kiss while I let her handle the rhythm below. It felt so much like a real couple that I got swept up in the moment, whispering sweet things into her ear.
”You’re so cute. You really are a charming woman, Cassandra.”
”Don’t say that… ♡ Not now… ♡”
”I’ll say it whenever I want. I love you, Cassandra. Not as a roleplay, but from the bottom of my heart.”
”Nn… ♡ I… I… ♡ Ahhh! I’m going… ♡”
Her answer to my confession was a feverish kiss, a tight embrace, and a sudden, violent climax. Her face was melted in a sweetness that no ordinary lover could match. I, however, missed my chance to finish again.
”I’ll take that as your answer, Cassandra.”
”Nnn… ♡ What… are you talking about… ♡”
She still wouldn’t give me the words. Even though her body was screaming “Yes.”
”Fine then. I’ll just keep going until you give me a clear answer.”
”…You really don’t know when to quit.”
”Is that a ‘no’?”
”…No. I’ll stay with you as long as my body holds out. After all… right now, I’m Daisuke’s lover… ♡”
She looked exasperated, but also a little happy as she accepted my request for an extension. It was going to be a very late night.
—
Summary:
Daisuke spends the final night of the expedition with Cassandra at an inn. He proposes a ‘Lover Roleplay’ to deepen their bond before they part ways. The night escalates into intense intimacy where Cassandra begins to lose her stoic composure.
—
Trivia:
- Daisuke has spent more nights with Regina and Ilse than Cassandra.
- Cassandra has zero dating experience despite her age and rank.
- Healing Magic is used to prevent physical soreness from repeated acts.
- Daisuke’s affection for Cassandra isn’t just physical; he explicitly confesses love
—
Character Insight:
Cassandra shows significant growth by moving from ‘reluctant’ to ‘actively participating’ in the seated position. Daisuke shows a more romantic side by prioritizing her emotional reaction over his own immediate climax.
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Lore And Worldbuilding Context:
The author uses ‘Lover Roleplay’ as a narrative device to bridge the gap between a transactional relationship and a romantic one.
—
Glossary:
Notes:
• Cassandra – 175 cm tall, short brown hair, muscular frame; stoic Krieger heir, daughter of a Knight‑Class father and Housekeeper mother, once ‘The Ogress’ and Royal Knights VP. B‑Rank defense specialist leading the Third Unit, bound by oath to serve Daisuke as a slave. Cold aura hides trauma from her father, hatred of Otto and traitorous adventurers, and a thawing intimacy with Daisuke.
• Regina – Late‑twenties Onee‑san with blue‑purple hair, green eyes, marine‑blue thigh‑split dress, thigh‑high socks, and a large‑breasted figure. She runs Daydream (BSS), mentors Nora and Rita, and is a respected senior Beastman and elite courtesan famed for her Masterpiece body. Insecure about her age, she’s targeted by the protagonist’s revenge and part of Daisuke’s circle hoping she’ll retire to follow him.
• Ilse – Seventeen‑year‑old tiger‑type beastman archer with pointed ears, a thick tail and petite frame. Once a merchant‑guild worker turned bandit, rescued on an escort mission and now Daisuke’s companion. Blunt, headstrong, diligent; bow‑skilled, scavenger talent, high Fortitude. Informal with Daisuke, craves his attention, teases him, asks for the ‘aahn’ feeding, uses magic and flashes a wry smile at his overwhelming strength. Energetic slave girl, bold and perverted about rewards.
• Emily – Thirty‑year‑old Captain of the Knights’ Order, B‑rank adventurer‑equivalent, sports wavy purple wolf‑cut hair tied back, a powerful aura and wicked older‑sister‑like smile. Married, leads the Third Unit, chaperones a high‑school girl party, teases Daisuke with disciplined charm. Recently recovered from battle, unconscious and being carried by Cassandra, wielding a segmented great scythe.
• Daisuke – Mid-40s Japanese B-Rank adventurer with a youthful face due to the Green God’s blessing, he hides his overwhelming strength while mastering Earth/Wind magic, regeneration, stealth, speed, transformation, Item Box, healing, and unique fire magic—plus the rare Ordeal and Foresight skills. Wields a one-handed sword and buckler, excels as a chef, and quietly dominates the adventuring world. Coordinates teams, mentors Rin and Cassandra—whom he’s romantically pursuing with deep empathy for her trauma—while dating Ines, pursuing Regina and Dietlinde, and managing slaves Ilse, Liese, and Camilla. Leads lake investigations and Royal Knight missions, travels toward the Royal Capital, and is revered as the knight-saver who vowed to protect them all.
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Edited by Kanaa-senpai.
Thanks for reading.
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