Isekai Hero Bartender

Was I just getting older, or were my hangovers getting worse since I’d started cutting down again? I could just about feel the angry, disheveled snarl of hair crying out on my scalp. My mouth was filled with cotton balls. Blood hammered my head like the world’s worst drum solo.

Wynnie looked the opposite of how I felt. Simply radiant. Her plump cheeks flushed with a rosy shine as she propped herself up on her elbow.

"Good morning, sunshine! You must've gotten in late last night."

“Gnrf.”

“Up drinking?”

"Yeah, sorry about that. I ended up having a chat with Shivai, and we settled on a new cocktail to add to the menu."

"Oh yeah? What did you two talk about?"

My mouth felt sticky and dry. I hadn't done anything wrong, and I knew it. Yet it didn't feel right to sleep beside her all night without letting her know that Shivai had made a move.

Or at least, I was pretty sure she had. In Europe, a quick bisou was tres chic, non? Just a, um, friendly little gesture between pals.

This wasn’t Europe, of course. And the kiss, though little, felt more than friendly.

I stalled, looking out at the coming day. Sunlight streamed in through the cracks between the curtains in our shared bedroom, catching motes of dust as they glittered, suspended in the air.

I was becoming accustomed to waking up like this, feeling an idyllic peacefulness from a slower pace of life than back on Earth. Not having screens constantly vying for my attention certainly helped. But one thing I wasn't used to was just how warm it was upon waking. The sheets were damp with a thin layer of sweat, and I could feel the day already growing uncomfortably humid.

Still, if we were talking uncomfortable, nothing beat Wynnie's question. It was time to come clean.

"We talked a bit about my sword training with Lady Talia," I started, building up to it. "And some cocktail stuff. Oh, and I talked to her about using her charm on customers. She won't do that anymore. I think."

She smiled, so wholesome and tender. "I knew I could trust you to handle that!"

Of course she trusted me.

"Oh, and she kissed me. Kind of."

Her eyes grew wide. Silence stretched between us a beat too long, and my pounding heart decided to break it. It thumped audibly in my ears.

“On my neck. Below my ear. I, uh, I didn’t—”

Yet before I could apologize and tell her how sorry I was and that I wouldn't let it happen again, she giggled.

"Jeepers! I knew it! I knew she couldn’t hold back! I knew she would make a move!"

She was still giggling. Was it one of those nervous giggles where she didn't know how to react?

But if that was the case, then why was she smiling?

"I'm really sorry, Wynnie. It was such a surprise that I didn’t have time to react."

“Typical succubus. So impulsive.” She caught her breath and looked meaningfully at me. "Did you like it?"

"It wasn't even on the lips."

"Yeah, but did you like it?"

There it was: that weird, clamped-up feeling in my throat again. I didn't want to make things weird, but I also wanted to make sure that our relationship was built on a foundation of trust and honesty.

"Her lips felt nice, I guess."

“But did it make you feel gooey inside?”

“Um. Right before anxiety knotted my stomach, yeah.”

"And did she use her charm on you?"

"I didn't see any flashing eyes, if that's what you're asking. I might've had more than a few drinks, though."

She shrugged. "Alcohol doesn't change who you are. If anything, it just makes you more you. It shines a light on the truth within."

That's what I'd always believed, too. People who got angry and violent when they were drunk usually harbored an angry and violent personality, even if they hid it while sober. People who became more promiscuous after some drinks, well, they always wanted to let loose. Alcohol just gave them permission.

As for me, I always felt self-conscious without some liquid courage. Booze freed my opinions and turned up my volume. After a drink or six, I didn’t fear the vulnerability of having feelings. I just told people that I liked them.

Drunk Drew was a lover, not a fighter.

And after our evening together, I had to admit that I actually really liked Shivai. I still wasn't sure I could trust her completely. She could probably charm the teeth out of an alligator.

"Yeah, I liked it," I confessed again. "But I won't let it happen again. Promise."

"Is that so?"

"Yeah. I'll tell her that the dagger training date she had planned is called off. Maybe I can put a bit of distance between us."

She scooted out of bed, touching her dainty toes down to the warm wooden floor. I could see through her nightgown slightly. The barest hint of the woman underneath poked out less aggressively than usual, since it wasn't cold like most mornings.

Her brown hair fell loosely around her shoulders, and she combed it back with her fingers, searching the room for something to tie it back with. She snatched a ribbon from her nightstand and swept it into her usual messy bun.

"Actually, I think maybe you should take her up on that."

"What?"

"The date. Don't cancel it. If you're learning how to sword fight from Lady Talia, you might as well learn to use a knife, too. Shivai could make a good teacher.” She crossed the room to her dresser, giving me a sly, inscrutable glance as she passed. "It’s not much, as dates go, but you have to start somewhere, I guess. Just don't rush into anything."

My head swam, trying to figure out the rules of this world—and our relationship. She'd mentioned wanting to explore other women at some point, but also wanting to keep it intimate for now.

It couldn’t be a test. Wynnie was earnest, not sneaky. Her measured tone made it clear she’d thought this through.

“Just so I’m clear on what you’re suggesting, you think I should go on a knife date with Shivai?”

“Yes. And, if you like it,” she picked nervously at her nails. “I mean, if you like her, perhaps you could go on a real date, too.”

“Is that what you want?”

“It might be nice.”

Still in her nightgown, she rooted around in a messy drawer of her dresser. Only the barest tangle of lace spilled out from the top. She picked up a black, almost see-through thong, and tossed it aside, searching for something different.

"Anyway, I hope you're not too hungover to run some errands this morning."

She looked over her shoulder at me. Her shoulders dipped as her fingers slipped under the straps of her nightgown. It fell in a ringed heap around her dainty feet.

I blinked. "Huh?"

It took me a second to remember what she'd just said. I was distracted by the bare, ample backside she'd just revealed.

Goodness, but elves in this world were different from what I'd expected. In my roleplaying games, they were all supposed to be tall, willowy, pale, and without too many curves. Wynnie—Wynderriel—was tanned, freckled, and wildly voluptuous.

“You seem distracted.” A coy smile. “Can you run errands?”

"I mean, yeah, I'm good to go. Just a little headache. And a bit of regret, but I think that has mostly faded into confusion," I added, chuckling.

After careful deliberation, she selected a pair of wide, unflattering panties. An apologetic smile lifted her cheeks. With a shimmy, she slipped them on before turning her attention to the dresses draped on hangers.

She had a few to choose from now. Her fingers lazily walked between each option, sliding the wooden hangers to the left as she considered and then moved on. When we’d first met, I was pretty sure she'd had just the one, plus maybe a dirty spare for laundry day. Now, a small variety of cuts and tones promised a look for any occasion.

Her gaze settled on a lavender and indigo sundress. She pulled it off the rack and held it against her body, sticking one leg out. I laughed quietly to myself. Funny that women tried on outfits the same way in two different worlds.

I gave her a thumbs up and a nod of approval. “That one. Definitely.”

“You say that every day!”

“You look beautiful every day.”

“Charmer,” she muttered. She stepped into the dress daintily and pulled it up, looping her arms through the straps. "Okay, good. You keep talking about this ice cream stuff. I don’t know why the cream has to be cold for it to taste fancy, but you got a girl curious!”

“Would it help if I told you that melted ice cream is a miserable experience?”

“No! That just makes the riddle harder!”

Well, something was harder, that was for sure. I couldn’t watch Wynnie squeeze herself into her top without having more of those reasonable guy thoughts. The upper swells of her breasts spilled out from the low neckline as she cinched the strings on her chest tighter.

She let out a soft grunt with the last cinch. Her fingers delicately twisted the laces into the beginnings of a knot. Then she paused, looking at me.

“Everything okay?”

“So squishy.”

Pink flushed across her cheeks, and she looked down with a soft smile. “In a good way?”

She still didn’t believe that some men had exquisite taste. In that corset-like dress, her booba was the most motor-boatable squish-fest I’d ever seen. I wanted my face, cock, and hands all to feel that lustable, juicy tit-flesh at once.

So, maybe exquisite taste was slightly undercut by my lascivious id. Whatever.

“In a great way,” I assured her.

“If you get ice cream supplies, maybe I’ll let you untie this bow later.”

"Consider it done," I said, saluting her smartly.

"I'll stick around here and tend to our guests," she continued. Her hands smoothed out the fabric where it bunched and clung to her body. "Oh, and I need Shivai out of her room soon."

Immediately, I grimaced. Kicking the succubus out sure sounded like retaliation to me. And here I’d thought Wynnie was surprisingly open to sharing the love.

I wondered if the Good Inn had an open room for her—just until things cooled down here.

Wynnie laughed, noticing my reaction. "Oh, no. I'm not kicking her out. Just a temporary relocation. More sailors will be coming to port soon. I'm pretty sure we'll have a full house, and we could use the extra coin.”

“A temporary relocation to where? A cot in a storage room?”

“We’ll figure it out. We should have another day before we get overwhelmed, I think.”

I let out a sigh of relief. Then I hopped out of bed, preparing to dress myself for the day. My manhood hung heavily in my boxer briefs, the outline more than visible as the last vestiges of my morning wood shrank away.

She caught it, though. Her eyes darted below my waist. Her hands, still smoothing the last crinkles in her dress, stopped, waiting. They picked anxiously at the loose fabric as though considering undoing all of her preparations so far.

"We have some time before you head out to the farm for cream, you know."

"Oh, sure. I figured we'd have a bite to eat first. Breakfast, coffee, make sure the guests are set," I said.

"And we still have at least half an hour before it gets too hot for comfort in here." Wynnie chewed on her bottom lip, letting the implication hang.

I may not have maxed out my intelligence stat in real life, but my insight skill had to be decent, at least. In short, I was picking up what she was putting down.

"Do you want to go back to bed real quick?" I asked.

"Absolutely. But how about, instead of real quick, we stretch it out a bit? No need to rush."

"Good thinking. We'll make sure you climax at least twice." I licked my lips, looking forward to both the rush of feverish liquids hitting my mouth for the first, followed by the agonizing, arrhythmic convulsions of her sex gripping mine for the second.

And why not? Maybe the third, too.

Her thumb and forefinger tugged at the string holding her chest in. Physics immediately ensued.

Wynnie drew near. “I’m going to smooch you everywhere.”

“Even here? You could cover Shivai’s kiss with your own.”

I pointed to the spot on my neck where the succubus had marked me with her lips. It still felt hot and sticky, tingling with a curious electricity.

On tiptoes, Wynnie kissed me on the opposite side.

“No. Everywhere but there. That part can be for her.”

“Oh?”

“Just see how it feels to let her touch linger on you. Think about her hot breath on your ear as her emotions took control and gave her the courage to make a move.” Wynnie’s thumb slid beneath my waistband, questing downwards. “Imagine her here with us, now. Watching my cunt sheath you whole, just waiting desperately for her turn to join in.”

Small fingers wrapped around my cock. My pounding pulse beat in her hand as I hardened in her grip.

I was imagining it, alright. As long as that’s what Wynnie wanted.

I couldn’t wait to hear her high-pitched wails and surprisingly dirty talk. Nobody else could make, “Oh, goody gumdrops” sound so inappropriate.