Volume 5 Chapter 5 Simulated Experience☆*
Edited by: Kanaa-senpai
Today, I have a major mission: to give Regina-san cosmetics as a present. Regina-san is always beautiful and wonderful, but she tends to hold back a bit because of the younger girls sitting on the shop’s dais. Well, given the shop’s direction of pushing younger girls, and the fact that she is completely past the marriageable age¹ in this world, it can’t be helped.
By gifting cosmetics to such a Regina-san, I want her to feel a little more cheerful. After finishing my date with Clarissa-san, I have Regina-san called for me at the brothel “Daydream (BSS).” I didn’t see Rita or Nora today. Since they are popular girls, this is normal.
”Welcome. Thank you for coming today, too. ♡” Regina-san said.
”Good evening, Regina-san. I look forward to your help today,” I replied.
As usual, we link arms and head to a private room. No matter when I come, the pressure is marvelous. Should I make it lovey-dovey s*x today, or make it intense? Maybe a situation play is also on the table. We enter the private room and engage in some small talk.
”Come to think of it, I heard a ‘Dungeon Upheaval’ occurred in the dungeon. Were you okay?” Regina-san asked.
”The ‘Dungeon Upheaval’ itself was fine. A lot happened and I ended up having a duel, but as you can see, I’m healthy,” I said.
I thought about hiding the story of the duel, but it would be worse if it were found out later and damaged our relationship of trust. I gave up and told her.
”You did something dangerous like a duel? I can understand the circumstances, but don’t overdo it, okay?” Regina-san said.
”Yes, I am reflecting on it,” I said.
”Fufu, you’re going to prove that your invitation to stay together after I retire isn’t a lie, right?” Regina-san asked.
”That’s right. I won’t die until then,” I replied.
Since that topic came up at just the right time, I’ll give her the cosmetics first. I’d be lucky if Regina-san fell for me with this, but it might be difficult.
”As part of showing my seriousness, I’ll give you this as a present,” I said.
”Oh, what could it be?” Regina-san asked.
”They are cosmetics that came out of a treasure chest in the dungeon. I won’t use them even if I have them, so please, by all means, use them,” I said.
”Eh? I use some because of my job, but cosmetics are expensive if you sell them, you know? A full set should be worth dozens of gold coins…” Regina-san said.
Regina-san is hesitant to accept, intimidated by the price. However, she is glancing at the box containing the cosmetic set, so it doesn’t seem like she doesn’t want it. In that case, I’ll give her a push.
”That’s a down payment. If you’re coming with me, it’s only a matter of whether the time is early or late,” I said.
”It’s certainly expensive, but you don’t think I’ll make up my mind with just this, do you?” Regina-san asked.
Regina-san sees right through my inner thoughts. It’s true I thought the win rate was low.
”You got me. As expected of Regina-san,” I said.
”Fufu♡ I’m watching you closely, aren’t I? Aside from that, this is a bit expensive, you know? Isn’t it more expensive than the total amount I’ve been paid here so far?” Regina-san asked.
”I suppose so. If you’re concerned about it, please do a little acting in this play,” I said.
”Acting?” Regina-san asked.
”Yes. You could call it situation play, where we imagine a certain situation and act… it’s a situation like… It would be great if Regina-san could do it like…” I said.
”Hmm, I’ve never done acting before, but is that okay?” Regina-san asked.
”Yes,” I replied.
”I understand,” Regina-san said.
I can enjoy myself enough just doing things as usual, but something like this isn’t bad once in a while. First, we both take a shower, and the play begins.
* * *
Knock knock.
”…Daisuke-kun, you’ve come again,” Regina-san said.
”I’ll come as many times as it takes until Regina-san says yes,” I replied.
”…Well, fine. Come in,” Regina-san said.
Obtaining Regina-san’s permission, I enter her room.
”Regina-san, it’s been three years since your senior died. It’s about time you moved on,” I said.
”But I… that person… besides, I’m not young anymore,” Regina-san said.
The situation this time is “a widow who lost her adventurer husband and a junior adventurer.” I thought about a stepmother situation, but I rejected it because it treated Regina-san too much like an older woman.
”No, Regina-san remains as beautiful as before. Aren’t you young enough?” I asked.
I take Regina-san’s hand and woo her, but Regina-san casts her eyes down sadly and turns away.
”…Even if it’s like that for Daisuke-kun, I am already…” Regina-san said.
”Or do you dislike me?” I asked.
”There’s no such thing as… disliking you,” Regina-san replied.
”Then let’s ask your body whether Regina-san is young or not,” I said.
”Eh?” Regina-san said.
I hug Regina-san from behind and knead her large breasts.
”W-wait, Daisuke-kun!? If you do something like that… ah♡” Regina-san cried.
”If I do something like that, what happens?” I asked.
Even through her clothes, I knead Regina-san’s favorite n**ipss, and when I give them a quick tug, a sweet voice leaks from Regina-san.
”It’s no good, Daisuke-kun! I… that person… ahn♡” Regina-san moaned.
”But your senior is no longer here. There’s no need to hold back,” I said.
”Haaa♡♡” Regina-san sighed.
As I say this and lick her neck, she trembles with a thrill and the strength leaves her knees. Before she can slump down, I hug and support her, continuing the breast caress with just one hand.
”If it’s been three years, you must have a lot of pent-up frustration, right?” I asked.
”That sort of… thing is… haa♡” Regina-san said.
I carry Regina-san, who is gradually melting from the assault on her n**ipss and neck, to the bed and make her get on all fours.
”Haa♡ haa♡ It’s no good, this kind of thing♡” Regina-san panted.
”You say that, but you’re actually expecting it, aren’t you?” I asked.
When I reach my hand through the gap in the deep slit and touch her private parts, her underwear is moist and wet. This time, as a special request, we are playing with her wearing not just the dress but her underwear as well. Judging from the wetness, it seems Regina-san is enjoying it too.
While kneading a n**ips with one hand, I target her clitoris from over her underwear, and her voice leaks out, unable to endure it.
”Nngh♡♡ Spare me already♡” Regina-san begged.
”Your body isn’t saying that, you know?” I said.
Reaching my hand around from behind Regina-san, I squish and knead her n**ipss, giving them a quick pinch every now and then. My other hand focuses the assault on her clitoris from over her underwear, and I suck and lick her neck. I focus the assault on Regina-san’s favorite spots, but she still resists with words.
”Kuu♡♡ No♡ Any more than this is no good♡” Regina-san said.
”Now then, let’s see what’s happening down there,” I said.
I pull the hem of the dress up over her waist and shift the crotch of her panties to expose her private parts. I knew it from touching over her underwear, but she is sufficiently wet.
”This place is honest. You’re already completely prepared to accept me,” I said.
”There’s no… such thing♡” Regina-san replied.
For a Regina-san who won’t admit it despite such a great flood, punishment is necessary. I quickly take off my trousers and underwear and rub my rock-hard c**k against Regina-san’s private parts.
”No♡ Just that is no good♡” Regina-san said.
”If you really hate it, please run away,” I challenged.
I deliberately advance my hips slowly, but Regina-san did not try to run. Her body, which continued to be teased, surged hotly and welcomed me, contrary to her words. It’s slippery with the overflowing love juice, and it feels very good.
”Haaaa♡♡ It went… in♡♡” Regina-san cried out.
”Ugh…! As expected of Regina-san…!” I groaned.
Since I can’t see her face and it’s hard to kiss, I’ve never done it with Regina-san from the back. However, Regina-san’s v**ina squiggles and wriggles as usual, trying to milk me dry. Because of this truly masterpiece organ, my limit approaches all at once. Since I can’t afford to lose, I transform my c**k for Regina-san. I make it a little longer and emphasize the flared edges of the glans. With this, I gouge the weak points of the side walls and thud against the Portio; finally, signs of surrender begin to emerge.
”Aah♡♡♡ No♡♡ Because it feels good there, it’s no good♡♡” Regina-san moaned.
”It means Regina-san and I have good compatibility,” I said.
As I grab her large, round, soft buttocks and slam my hips against them with a smack-smack, the strength in Regina-san’s arms fades more and more. Even in that state, her v**ina tightens with a squeeze-squeeze to match the thrusting, so I don’t have much leeway either. Since I’m at it, I want us to go together, so I’ll thrust a bit more intensely.
Increasing the pitch all at once, I attack with fast, long strokes, and Regina-san’s limit also draws near.
”Haaaa♡♡♡♡ No♡♡ I’m going♡♡ I’m going to climax from being violated by my husband’s junior♡♡” Regina-san screamed.
”Regina-san, please take it all!” I shouted.
Finally, I stab in deep and e**culate into her uterus with a gush-gush. As expected, doing it with Regina-san feels great.
”Haa♡♡ haa♡♡ I was made to go♡” Regina-san panted.
”You felt my seriousness, didn’t you? Will you come with me?” I asked.
”…If you do this much to me, I have no choice but to admit it♡ What a helpless boy♡ I’ll follow you, Daisuke-kun♡” Regina-san said.
”Thank you very much,” I said.
Finally, I close the situation play with a passionate kiss. At the end, I was able to hear Regina-san say “I’ll follow you,” so I’m very satisfied. I like lovey-dovey play the best, but this is good once in a while.
* * *
After finishing the situation play, we move on to a little pillow talk. I want to hear Regina-san’s impressions too.
”How was it for you, Regina-san?” I asked.
”Fufu♡ It was fresh and fun♡” Regina-san replied.
For someone who said it was her first time, her acting was good. Since I’m a ham actor, I think I was probably terrible. It was fun, so it’s fine though.
”Well then, please continue from here as usual,” I said.
”I understand♡ The sweet, sugary play Daisuke-kun likes, right? ♡” Regina-san replied.
Since my s*xual preferences are wide open to Regina-san, “the usual” gets the point across. It’s a mix of happiness and embarrassment. This time, I cover Regina-san, who I’ve had lie on her back, and caress her large breasts. Since she’s already wet, it’s unnecessary, but I can’t leave this out.
”Ahn♡♡ Daisuke-kun really loves breasts, don’t you? ♡” Regina-san said.
”I love them. Because they are my beloved Regina-san’s breasts,” I replied.
”Geez, saying things like that♡♡” Regina-san said.
Though her words sound like she can’t help it, she smiles very happily. She really is a charming woman. I munch and suckle on her breasts, and while kneading them with both hands, I suck and lick her n**ipss. One way or another, Regina-san also likes her n**ipss, so she is properly feeling good.
”Ahn♡♡ Is it only that one? ♡♡” Regina-san asked.
”You seem like you’re not satisfied,” I teased.
Since Regina-san, who had settled down once, had become aroused again, we connect in the missionary position. The back wasn’t bad, but as expected, this is better. I can see Regina-san’s beautiful face, and it’s easier to kiss. At the finish, Regina-san clings to me, so the sense of satisfaction is amazing. While exchanging deep kisses with Regina-san, I move my hips. Since it’s a sweet, sugary play, I don’t make it intense at first.
”Nnh♡♡ haa♡♡ More♡♡ Please♡♡” Regina-san begged.
”Understood,” I said.
In response to her request, I gradually make it stronger. Of course, my hands knead her breasts, and I squish, pinch, and pull her n**ipss. Since I’m also thrusting without missing Regina-san’s good spots below, Regina-san’s reaction gradually becomes sweet and melted. The strength with which she pulls me close becomes stronger, and her legs are crossed behind my waist, refusing to let me go. I have no intention of running, but I’m happy that Regina-san is also feeling good.
”Ah♡♡♡ Nnh♡♡♡ It’s good♡ I feel like I’m about to go soon♡” Regina-san said.
”You like this too, don’t you?” I asked.
While lightly pressing her stomach with my hand, I push my hips in deep to shake her uterus with a thud-thud. Regina-san, whose Portio was developed by me, lightly climaxes intermittently from just this.
”Ah♡♡♡♡ Ah♡♡♡♡ No♡♡ I’m going♡♡ I’m already going♡♡” Regina-san cried out.
”It’s the last spurt!” I shouted.
Since Regina-san is almost at her limit, I’ll make it intense for the last spurt. I rub the v**inal walls with long strokes and knock on the Portio with a tap-tap. I pinch her n**ipss a little strongly and give them a quick tug. When I lick her neck too, Regina-san arches her back greatly and reaches a climax.
”Haaaaaa♡♡♡♡♡ I’m c**ming♡♡♡♡♡ Daisuke-kun♡♡♡” Regina-san screamed.
”Me too! I’m going!” I shouted.
Since Regina-san went, her slippery v**ina, smeared with plenty of love juice, milks me as if pulling me deeper and deeper. Without resisting that, I press the glans against the cervical opening and e**culate into the uterus so much it seems like it would make a throb-throb sound. Being able to come inside my beloved Regina-san feels very good.
* * *
After remaining connected with a deep kiss for a while, I reluctantly pull my body away. I lie down next to Regina-san just like that and move on to pillow talk.
”Today was a situation play, but I was happy to hear Regina-san say ‘I’ll follow you.’ Does that mean it’s okay now?” I asked.
”Fufufu♡ That was still acting♡” Regina-san replied.
I ask her every time, but she won’t readily give her consent. Judging from her reaction, it’s just one more push though. Burying myself in Regina-san’s breasts until the very last minute, I decided to go home for today.
—
Summary:
Daisuke visits Regina at the brothel to gift her expensive dungeon-looted cosmetics, hoping to cheer her up and convince her to leave the brothel life. They engage in a ‘widow and junior’ roleplay scenario where Regina acts out a surrender to his advances. Although she playfully claims her agreement to follow him was just ‘acting,’ their bond deepens through the session.
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Trivia:
- Regina’s insecurity about her age highlights the harsh social standards of this world, where she is considered past her prime despite her clear beauty.
- The mention of Rita and Nora being ‘popular’ suggests they might be busy in future chapters when Daisuke needs them.
- Daisuke’s ability to ‘transform’ his body during intercourse suggests a unique physiological or magical power set that isn’t fully explained but impacts his efficacy as an ‘onanist’ protagonist
—
Character Insight:
Daisuke is transitioning from a mere customer to a prospective partner/savior for Regina. While Regina maintains her professional ‘acting’ facade, her willingness to engage in complex roleplay and her reaction to the gift show a shift toward genuine emotional reliance. ‘…I’ll follow you, Daisuke-kun’ serves as a pivotal, albeit roleplayed, admission.
—
Lore And Worldbuilding Context:
Dungeons are sources of high-value luxury goods like cosmetics, which hold significant economic power (dozens of gold coins). The brothel ‘Daydream’ operates with a hierarchy where younger girls are prioritized on the dais, indicating a youthful-centric beauty standard in this fantasy setting.
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TL Notes:
The author notes that this chapter was delayed due to illness but saw a record high in page views. The scenario was based on a suggestion from a reader (‘self-restraint Section Manager’) but was ‘arranged’ to fit the characters.
—
TL Notes:
Notes:
• Regina – Late‑twenties Onee‑san with blue‑purple hair, green eyes, marine‑blue thigh‑split dress and thigh‑high socks, large‑breasted figure; runs Daydream (BSS), mentors Nora and Rita, respected senior Beastman and elite courtesan famed for her Masterpiece body. Insecure about her age among younger girls, she’s a target of the protagonist’s revenge and part of Daisuke’s circle hoping she’ll retire to follow him.
• Clarissa – Early‑20s librarian with soft, graceful features, blonde shoulder‑length hair, sparkling eyes and warm natural charm; she radiates a gentle older‑sister aura, curvy figure and large breasts, and offers a slightly pressuring smile when discussing makeup. A glamorous merchant’s daughter, long‑haired and rose‑scented, knows geography well, casually helps Daisuke, survived many failed engagements, and is now his associate after their recent date.
• Nora – Petite beast‑girl with long curled grey hair, drooping ears and a tail, called “Number Two” at Tagtraum and Daydream. She works as a sex worker at Daydream, specializing in oral techniques (Deep Throat), serving Daisuke arm‑in‑arm, playful yet serious, fighting and sharing beds with the protagonist, luring clients with erotic charm and squeezing them dry while using cuteness to toy with men’s hearts.
• Rita – Standing 175 cm tall, this wolf‑type Beastman girl boasts dark brown hair, a fluffy tail and pointed ears. Her athletic, sprinter‑like build shows toned abs and massive stamina, while her long tongue and confident grin mark her as the famed “Number One” of Daydream. Popular and friendly, she thrives on competition and challenges.
• Daisuke – Mid-40s Japanese reincarnated adventurer, B-Rank with high AGI/DEX, wears a ten-year-old watch and Radiant Iron gear. He wields Healing, Fire, Ground Shrink, Flash Move, Mental Memory and massive Item Box. Mentor to Liese, Camilla, Rin; dates Ines; pursues Regina at brothel Daydream; leads a household, cares for slaves, avoids the spotlight, and explores the continent.
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Edited by Kanaa-senpai.
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