After seeing Lady Dietlinde off, I considered heading to a tavern. The inn served meals if you asked, but I was in the mood for a change of scenery. Back in my previous life, I’d frequent izakayas or bars alone until my health started to fail. Sitting at a table by yourself is a lonely affair, but at the counter, you can chat with the owner and enjoy your drink. I’d just been out with Mercedes, Ines-san, Juliet, and Sylvie-san yesterday, so it wasn’t as if I’d been cooped up, but drinking solo has a certain peace to it. I started scouting the entertainment district for a place with a decent atmosphere.
”You’re Daisuke, right?”
I turned, squinting at a familiar face I couldn’t quite place. I’ve always been terrible at remembering men’s names.
”You’re the leader of Kenta’s party, aren’t you?”
”Daisuke-san, good evening.”
It was Alberto-san, the blue-haired beastman who’d been coaching the Working Women Party. Kenta-kun was standing just behind him, looking a bit sheepish.
”Good evening, Alberto-san,” I replied. “What brings you out?”
”Kenta and I were just heading out for a bite. Why don’t you join us, Daisuke? Don’t worry about the tab; I’m treating the rookies today.”
Since I hadn’t settled on a place yet, I figured I’d take him up on the offer. I could use some pointers on the adventurer life anyway.
”I appreciate it. I’ll join you then.”
”That’s the spirit! I’ll show you a good time,”
Alberto said with a smirk. He reminded me of a certain senior I had back in my old life.
He led us to a club where women performed on a stage. It was a respectable enough place; the dancing was provocative, but it wasn’t a strip joint. The dancers wore revealing outfits that showed off plenty of leg and cleavage, their hips swaying with a rhythmic, erotic precision. Their sultry glances were enough to make your heart skip a beat. It was a pleasant way to enjoy a meal. As for the “adventure talk” Alberto was giving? None of it actually stuck in my head.
The entertainment district naturally had plenty of shops catering to women as well. If anything, there were more of them. I saw a group of barkers shouting, “Hey ladies, how about some d**k? You want some d**k?” It reminded me of the touts in N-City back in Japan shouting about tits, and I had to stifle a laugh.
”That was a great meal. Thanks for the treat.”
”Alright, now that we’ve got some food in us, it’s time for the second round!”
”Thanks-ssu!”
”Wait, I should probably—”
”Don’t be a spoilsport! Come on!”
Alberto dragged a reluctant Kenta-kun toward our second stop. It was a tiered brothel where you chose a girl from a lineup to take to a private room. Alberto immediately pointed out a beautiful beastman woman and disappeared. Kenta-kun looked like he wanted to bolt; his face was twitching with nerves. (Hang in there, kid. I used to be just as stiff.)
The girls ranged from cute to elegant, humans to beastmen, though most were quite young. That seemed to be the standard in this world. After the dancing at the last place, I was firmly in the mood for a mature, “older sister” type. As I stood there indecisive, a woman in a marine-blue dress approached me. She looked to be in her mid-twenties with sharp green eyes and blue-purple hair pinned back with a barrette. A deep slit in her skirt revealed a glimpse of a thigh in a silk stocking, and her low-cut dress didn’t leave much to the imagination regarding her impressive bust. She was exactly my type. Technically, counting my previous life, she was probably younger than me, but in this body, she was the perfect older sister.
”Welcome. Is this your first time here?”
”Yes. Alberto-san recommended the place.”
It turned out she was the floor manager, and Alberto was a regular. I wondered for a second about him being a married man, but it wasn’t my place to judge a guy who was paying for my dinner. (If I can’t do my Private Power Generation, I won’t get experience points, but one day is just a margin of error.)
”You can pick any of the girls in the lineup and head upstairs,” she explained. “Which one do you like? If you tell me your preferences, I can make a suggestion.”
She was exactly the vibe I wanted. I decided to take a gamble.
”Can I nominate you?”
”Me? Are you sure?” she laughed. “I’m flattered, but you don’t have to be polite. We have plenty of younger girls available.”
She was kind and had a way of making you feel at ease. My mind was made up.
”I’m sure. I’d like you to be my partner.”
”Well, if you’re certain… I’d be happy to. Let’s go.”
She took my arm, pressing it firmly against her chest. The sensation of her weight was incredible. She gave a quick instruction to another staff member and led me toward the stairs. Kenta-kun was still paralyzed in the lobby, surrounded by girls trying to sell themselves. (Good luck, buddy. Don’t let them eat you alive.)
We entered a private room on the second floor.
”We have soundproofing magic tools here, so you don’t need to hold back.”
”I see.”
Those tools were expensive; this place was definitely top-tier.
”Let’s start with a shower, shall we?”
Actual running water—another luxury. It had been nearly a decade since I’d been in a place like this, counting my time in Japan. I started to feel a genuine flutter of nerves.
”Oh? Are you nervous?”
”To be honest, I’m not really used to shops like this…”
Since it would be too complicated to explain that it had been ten years when I currently look seventeen, I just played it off with a vague excuse.
”Hehe. Don’t worry. I’ll take good care of you.”
”P-please do.”
We stripped down, and I couldn’t help but stare. She was stunning. Her skin was flawless, her waist was narrow, and her curves were perfectly balanced. She’d even groomed herself neatly—a detail I appreciated. After a quick rinse and a herbal mouthwash, she led me to the bed.
”Can I ask your name?”
”It’s Regina. And yours?”
”Daisuke.”
We shared a kiss that started light and quickly deepened. The wet smack of our lips was the only sound in the room. Her body was soft and smelled faintly of flowers. Regina eventually pulled back, a mischievous glint in her eyes.
”That was a lovely start. How about we try this?”
Regina started licking my n**ipss while her hand went down to stroke my c**k. It was incredible—so incredible that I felt like I was going to hit my limit way too fast. I had to take control.
”That’s… that’s amazing,” I gasped. “But if we keep going like this, I’m going to finish too soon. Let’s switch. I want to feel your breasts, Regina-san.”
”You’ve been staring at them this whole time, haven’t you?” she giggled. “Go ahead. Be as gentle as you like. ♡”
I reached out, cupping the weight of her breasts in my hands. (Okay… time to go on the offensive.)
I pulled Regina-san close. While one hand gently kneaded her breast, the other traced the line of her spine. I moved my tongue along her neck, ears, and collarbone, searching for a chink in her armor. I kept her n**ipss as a final prize-they weren’t her only erogenous zones. (For a seasoned woman like her, a little teasing might be the most effective play. Let’s see if I’m right.)
As I held her, that sweet, intoxicating scent unique to women sent my pulse racing. It was a mystery how she smelled that good so soon after a shower.
”Ah…♡ Right there… that’s the spot… mmm…♡” Regina said.
I had found them. Regina-san’s weak points were her back and the nape of her neck. With the opening established, I finally turned my attention to her n**ipss. I sucked, licked, pinched, and rolled them between my fingers. I kept my touch light.
”Nnnh! Haah… that’s wonderful♡,” Regina replied. “You’re really getting into it. Ready to go inside?”
”Yes,” I said. “Uh, wait-do you have any protection?”
”Don’t worry, I’m on the pill,” she said. “It’s safe.”
(Whether it’s a literal pill or some fantasy equivalent, if she says it’s fine, I’m taking her word for it.) Regina-san lay back on the bed, and I rubbed myself against her, letting us both get used to the friction. She was already slick. It was time.
”Now, come in♡,” Regina said.
I lined myself up and thrust forward. I slid in with a wet, squelching sound. The slimy internal membranes pulsed and writhed against me; this was leagues more intense than her handjob earlier. It felt like I was being milked. I wasn’t just worried about not lasting-I felt like I’d blow in seconds. The pleasure was so absolute that restraint was impossible.
”Haah…! It feels… so good…!” I gasped.
”Fufu, thank you,” Regina said. “Go ahead… move for me♡”
If I stayed still, she’d finish me off without me lifting a finger. I thrust my hips, trying to mount some kind of counter-offensive. With every shove, the room filled with the rhythmic slap of skin on skin.
”Ah♡ Ah♡ Yes, it’s so good♡,” Regina moaned.
She was definitely enjoying it, but she still had too much composure. I stayed upright, shifting my weight to find a better angle. Desperately fighting the urge to finish, I pulled back to rub against the sensitive entrance, then lunged deep to grind against the back of her, tilting my hips left and right.
”Ahnn!♡ Right there!♡ More… give me more!♡” she cried.
I was supposed to be the one ravaging her, but Regina-san’s body was just too much. When I shoved inside, she took it with a soft, squishy welcome; when I pulled away, she clamped down, her internal folds clinging to me like a vice. I wasn’t finding her weakness-I was just taking critical damage. I was at my limit. Her breasts swayed wildly with every thrust. I couldn’t help myself; I reached out, kneading them and burying my face in the heat of her skin. When I latched onto a hardened n**ips and gave it a sharp little nip, she finally gave a genuine flinch.
”Ahhh!♡ You really are a breast man, aren’t you? Careful with the teeth, okay?” Regina said.
”Yes… haah… haah…” I panted.
Regina-san still looked composed, but I was done for. (The gap in our experience levels is a damn canyon…!)
”Regina-san, I’m… I’m gonna go…!” I yelled.
”Mmm, it feels so good♡,” Regina said. “It’s okay, just let it all out inside me♡”
I knew I’d lost, but I gave one last desperate struggle, swinging my hips with everything I had. I didn’t care about the “defeat”-I just wanted to make her feel something. If I could make her lose it, even for a second, it would be worth it.
”Ah!♡ Ah!♡ Ah!♡ Ah!♡”
”Aaaaagh! I’m coming! I’m filling you up! Take it!”
I lunged forward, locking my lips with hers as I buried myself as deep as I could go. I froze there, pressed tight against her. Regina-san seemed to realize it was the grand finale and squeezed me back just as hard. Her slick warmth tightened, those undulating folds milking every last drop out of me. I fired my load deep into her, burst after burst. (Go! Reach the bottom! Impregnate her!)
After the brain-melting climax, I couldn’t move. The taste of our entwined tongues and the lingering heat of the e**culation left me paralyzed. My lungs were burning. That was incredible.
”Mmm♡ You certainly had a lot stored up. That was lovely♡,” Regina said.
She smiled and praised me, but it was a total loss. Whatever. It felt good, so who cared? It’s not like s*x is a competitive sport. Once I regained the use of my limbs, I pulled out. A thick trail of s**men leaked out of her. She said it was fine, but seeing it made me a little anxious… and, honestly, incredibly turned on. (I can’t get it up again now, but that image is going to fuel some solo grinding for a long time.)
[Requirement for experience points met. Skill “Sexual Technique” acquired.]
A third round was physically impossible, so we spent the remaining time cuddling. When the clock ran out, I showered. Regina-san, back in her s*xy dress, walked me to the door. We shared one last kiss.
”Come back soon, Daisuke-kun,” Regina said.
”Yeah. I’ll definitely come see you again,” I replied.
That was half-politeness, half-truth. I had no chance of “winning” against her right now. I’ll come back for a rematch once my Sexual Technique level goes up. I know you shouldn’t think of s*x in terms of wins and losses, but being finished off that one-sidedly stung a little. (My mistake was probably skipping the foreplay and going straight for the gold. I’ll have to conduct a post-game analysis when I get home.)
By the way, when I bumped into Kenta-kun outside, he looked like a ghost. I don’t know if he got a dud partner or if he just got milked so hard his soul escaped through his pores. Hang in there, Kenta-kun.
Summary:
Daisuke encounters Alberto and Kenta while scouting for a place to eat in the entertainment district. Alberto treats them to dinner and then takes them to a high-class brothel. Daisuke chooses Regina, the floor manager, and they begin an intimate session in a private room.
Daisuke loses his virginity to Regina-san in a fantasy-world setting. Despite his attempts to ‘win’ through tactical s*xual maneuvers, he is completely overwhelmed by her experience. The encounter concludes with Daisuke gaining a ‘Sexual Technique’ skill and reflecting on his defeat.
Trivia:
- Daisuke loses EXP-gaining opportunities if he skips his daily ‘Private Power Generation’ session.
- The world has soundproofing magic tools, indicating a level of high-end magical consumer goods.
- Alberto is married, yet frequents brothels openly as a ‘regular’.
- Daisuke compares the local barkers to those in N-City (Niigata/Kanazawa) from his past life.
- Regina’s affection for Daisuke didn’t actually increase due to a debuff called ‘Effect of the Ordeal/Suffering’.
- Regina’s sweet words were confirmed to be professional ‘lip service’.
- Contraception exists in this world in the form of a ‘medicine’ (pill).
- The protagonist views s*xual encounters as game-like challenges with win/loss conditions
Character Insight:
Daisuke shows a preference for maturity and competence over youth, choosing the manager Regina over the ‘Number Two’ popular girl. Kenta is portrayed as a complete novice in adult environments.
Daisuke shows a mix of vulnerability and competitive pride; he is more bothered by his ‘one-sided’ defeat than the actual act. Regina is revealed to be a master of her craft, easily managing Daisuke’s emotions and physical reactions while maintaining her own composure.
Behind the Scenes:
The author, Osamu, mentions shifting to a more erotic style (Nocturne) due to reader demand and uses hearts (♡) for ease of writing.
The author notes that this is the protagonist’s actual first time (not a delusion) and highlights the ‘frightening’ nature of women who can wear such perfect masks of affection.
TL Notes:
1 ↩ Nocturne: A reference to ‘Moonlight Novel’ (Nocturne Novels), the R-18 section of the ‘Shosetsuka ni Naro’ website.
2 ↩ Private Power Generation (Jika Hatsuden): A common Japanese slang/euphemism for m**urbation.
3 ↩ -san: A common Japanese honorific used as a title of respect, similar to Mr. or Ms.
4 ↩ Sexual Technique (性技): A literal RPG-style skill acquired by the protagonist in this fantasy world system.