Chapter 1

Maybe I wasn’t paying attention. Maybe I had been reading too much isekai fiction and had, subconsciously, decided to try my luck. I knew intellectually it was ridiculous, but hey, maybe you could only read so much of that garbage before you started to internalize it, just a bit.

Whatever the actual reason, the truck did hit me. I saw it out of the corner of my eye a few seconds before it hit me. I didn’t move, and it never stopped moving.

Frankly, it hurt more than I thought it would.

On the plus side, it was over pretty quickly too. My eyes had been open until the very last second, which is why it was such a surprise to me that I then had to open them again.

I took in my surroundings with what I deemed an admirable degree of calm, considering I was floating suspended over a pit with gusting flames, creeping tentacles, and the ugliest, most misshapen faces that may or may not have once been human.

“Didn’t think I was that bad a guy,” I said absently.

“What makes you think it’s a question of morals?” a voice asked. I looked up, and immediately wished that I hadn’t. Floating a few dozen feet above me was a a beholder. Yeah, full on Dungeons and Dungeons style flying eyeball, except this one had six fluffy wings protruding out from the eye instead of the typical horrifying eye-stalks.

An ascended beholder? I wracked my brain for everything I knew about the aberration.

Insane, xenophobic aberrations that warred on themselves only slightly less frequently than they did other races. Perfect.

“I really don’t know why I said something that stupid. You’re right, I have no reason to think that morals had anything to do with it,” I said, deciding to go the obsequious route on the off chance that this beholder was slightly less homicidal than the rest of its peers.

“I’m not going to hurt you. You’re already dead, after all,” the beholder said, a slight tinge of annoyance in its voice.

“Ah, I was wondering about that,” I said. “Nothing really hurts, but I guess the pit of horrors down there should’ve tipped me off.”

“It does for most people,” the beholder agreed.

There was a short pause. “Soo...” I said.

“Oh, right. I’m not normally the one introducing people to this, but you’re a bit of a special case.” The beholder cleared his ... throat. “My name is Uriel. I am an angel. I have been sent here to offer you another retry.”

The eye, Uriel if he was to be believed, looked at me expectantly.

“Uriel. Bible-style Uriel.” I said.

“Yes. The very same actually.”

A delusional beholder. Mildly blasphemous, but I could work with that, I thought, ignoring the monster’s sigh (and how was it making all of these noises with just an eyeball and some wings?).

“Retry? Special case?” I asked. It seemed safer to stick to short questions.

“Yes. You died. And what’s worse, you did it to yourself. Which, honestly, is unusual, even for you.”

“I don’t recall this ever happening before,” I said politely, as if it was some trivial fact the aberration had overlooked.

“Of course not. You still have a human’s mindset since you haven’t ascended yet. If you remembered all of your past attempts, if they can really be called that, you would go totally be insane and poof. There goes your chance at ascending to the next level,” Uriel, as I decided to call him since he almost certainly was reading my mind, flapped his wings a bit, as if to punctuate his point.

“I think I’m getting the picture,” I said musingly.

“Really? Usually it takes people longer.”

“Humanity is an experiment by some higher beings which has several stages, of which Earth is only one, probably an earlier one, and we’re given retries until we have enough ‘points’ to ascend to the next level. We accumulate points through various acts on Earth, probably impressive ones if its a point based system, and since I’m dangling over a pit of eldritch horrors I have to assume I did not accumulate a great number of points,” I said. I would’ve made a few grand gestures with my hands, but, on trying, I realized I was totally paralyzed from the neck down. Which, at this point, just seemed par for the course.

“No points, actually. You’ve had some bad runs, to be sure, but this is actually the first time you’ve died with no points. Even toddlers usually end up with a few points,” Uriel said.

“I didn’t learn to walk until I was three,” I admitted.

“Fascinating,” Uriel said, in a tone that made me realize that he was genuinely interested in how someone could be as much of a screw-up as I was.

I would’ve puffed my chest out in pride, but, you know, paralyzed.

“How many points do I need to ascend?” I asked. “Just so I know for next time.”

“Not many. A few thousand. Most people get that much by their third or fourth try. Certainly keeps us busy coming up with new souls,” Uriel said, the eye shaking as he chuckled.

“I assume I’ve been at it a bit longer. Special case and all.”

“Oh yes.”

“A lot longer?”

“Oh my yes.”

“Enjoying this?”

“Immensely. It’s been a while since we last spoke. You called me an abomination beyond description and vowed that your next life would be your last.”

“Long time ago?”

“Over a thousand years,” Uriel said, with glee. “They call you the eternal sucker upstairs.”

I nodded. That seemed about right. “Is it a luck thing, or...?”

“Oh not at all. Everyone gets lucky eventually,” Uriel said. “You managed to botch those lives in truly spectacular fashion.”

I couldn’t help but be curious. “For example?”

“Most spectacularly, you were a well respected general during the American Civil War. Had more points than you had ever managed to accumulate, and it wasn’t even close.”

“I botched it.”

“Pickett’s Charge, they call it,” Uriel said, unable to hold back a small giggle.

“So you can lose points.”

“Only in truly special cases. Pickett’s Charge.” The stupid looking eyeball, which was definitely not an angel in my book, giggled again.

“Couldn’t come back from that?” I asked, still curious despite myself.

“Graduated last in your class, failed at war, fled to Canada, then ended up back in America failing at being an insurance salesman before you drank yourself to death,” Uriel said. “But, well, we’re not here to dwell on your very long and very unsuccessful past.”

“Of course not,” I said dryly.

“Frankly, your string of failures, amusing as it is to the rest of the multiverse, finally attracted the attention of the big guy. He was not pleased that we had turned out such a dud. Really gave it to quality control, let me tell you. But, he decided, since you’d been at it for so long, that he’d throw you a bone. Really went out of his way, let me tell you. You should thank him next time you see him,” Uriel said.

“The bone?” I asked, trying not to snap at the meandering giant eyeball.

“A new difficulty. Most people only get to choose between easy, normal, and hard. The classics, you understand. And most people choose normal, since even the added points from hard don’t really make it worth a life that will almost certainly be a failure.”

“I’ve been picking normal too?” I asked, certain that I hadn’t been since I wouldn’t even play Call of Duty on anything but the lowest difficulty.

“You’ve been picking easy for the last five hundred years straight. Apparently you were sure that the lower point allotment for success would be balanced out by achieving some success. Which, of course, you never actually achieved.”

“So what’s the special difficulty?”

Uriel zipped closer, his wings almost batting me in the face. “He was going to call it ‘very easy’ but, apparently, he was inspired by your reading choices in your last life. Thus, we have a new difficulty exclusively for you, called...” Uriel trailed off, as if waiting for an angelic drum roll. Or, judging from how he was looking at me, some spectator input.

“Can I guess?”

“Please do!”

“Isekai mode. It’s an isekai difficulty.” I said, trying desperately not to cringe.

Uriel burst out laughing. “Yes, yes, exactly right! You’re the only human to ever actually need an ‘isekai’ difficulty level. Congratulations!”

“So what, I get a cheat code or something and you’re going to drop me into some fantasy world?” I asked. That didn’t sound so bad actually.

“Of course not,” Uriel said, sounding taken aback. “Do you have any idea how difficult it is, how many angel hours it takes to make an entirely new world? We had to work overtime for almost an eon after the First Bay of Pigs just to put everything back where it was.”

“So, not an isekai?” I said.

“It’s a difficulty, not a way of life,” Uriel said. “You’re going to be put back on earth, in the same life you were just living, but things will be easier for you. You’ll barely get points, naturally, but at least you won’t be such a constant reminder of a well intentioned angel’s momentary slip-up that, frankly, could’ve happened to anyone.” Uriel trailed off into muttering at the end. I decided to ignore the disquieting idea that I was quite literally looking at my creator.

“Then what’s the difference?” I asked. “Forewarned and all that. Wouldn’t want to let the big guy down. Again.”

“Life will be easy. It will, in a key way, be harder for you to fail than it will for you to succeed. Play the lottery? Win the lottery. Join the military? Find yourself catapulted to command of the United States armed forces in the easiest war your country has ever fought. It took almost two seconds of work, but G-man assured us that there was no way even you could mess things up this time around.”

Now, I won’t lie, my first thoughts on unlimited success were not in, ahem, a professional context. After all, I had died as an eighteen year old. I had needs. Needs which, to this point, had gone entirely unfulfilled.

“Yes, even that,” Uriel said dryly.

“I didn’t say anything.”

“You didn’t need to. That, above every other consideration, even the idea of eternal bliss after a successful ascension, has been your overriding motivation in choosing easy. It hasn’t helped all that much, and it’s barely worth any points on easy, let alone isekai, but you will persist I imagine.”

“Everybody else is getting laid,” I argued.

“Actually, there’s a direct inverse correlation between the amount of time someone spends ‘getting laid’ and the likelihood that they will end up ascending,” Uriel said, adopting more of a lecturing tone. A particularly large burst of fire shot up from below, as if in agreement.

“Novelty isn’t worth anything?” I asked.

“A bit,” Uriel said.

“There are a lot of way to have novel sex,” I argued, feeling defensive at my instinct despite knowing that arguing with an ancient angel was usually a waste of time.

“Only a handful of men, and yes, they were all men, have ever ascended as a result of their sexual feats. And, I suspect I don’t need to remind you, that you are no Casanova.”

I stared back at the angel, insulted despite my best efforts to restrain myself. “I am now,” I said, in sort of the same voice that Christian Bale used in Batman Begins.

“Please don’t waste your new gift on an endless supply of meaningless sex,” Uriel said, any trace of amusement having fled from his voice.

“I will become the greatest sex machine to ever walk the face of the Earth. Women will see me and their panties will turn to ash. My face will be on every cutout on every shooting range in the world, so that father’s have their chance to practice defending their daughter’s from me,” I vowed, my voice taking on some of the same qualities as the preacher at my local church when he became particularly impassioned.”

“You will never ascend like that,” Uriel warned.

“Who needs ascension when you have endless pussy!” I cried, unable to hold back an insane laugh. “Take that, you walking copyright infringement. You unoriginal, pseudo-angelic piece of flying turd.”

My laugh cut out suddenly as I dropped two feet lower. One of the tentacles gliding along the sides of the pit made a swipe for me, falling a precious few inches short. I gulped audibly.

“Not again. Never again,” Uriel warned.

“Sorry. I’ve never been a winner before,” I said, blushing despite myself.

“Is it really winning if it’s handed to you on a silver platter?” Uriel asked. I got the impression it was a rhetorical question and, since I was already on the verge of being dragged into a pit of utter nightmares, I said nothing.

“I’m going to send you back now. And we’re going to have regular checkups. Checkups that will ensure you spend a reasonable amount of time on self-improvement, and not just gratuitous sex,” Uriel said.

I nodded absently, wondering if I would be able to get Courtney Combs to break up with her college boyfriend. Merited further investigation, I decided.

“Now I remember why I usually let the interns handle you,” Uriel said.

“I won’t let you down Xanathar. This will be a fresh start for me, one filled with wonder, joy, and more orgasms than even Will Hunting could count,” I promised.

“If you don’t get any points this time I’m going to make a unilateral decision of sending you to the pit. He’ll forgive me if it’s you,” Uriel said.

There was a tugging motion at my navel and suddenly I was flying through the air, Uriel rapidly becoming nothing more than a pinprick below me. I closed my eyes and let a wide smile overtake my face.

Finally, my master plan was coming together. The fools! If there had been any wind in the weird, purgatorial hellscape it would have stolen my laugh away. As it was, the sound awkwardly faded away below me as I soared.

Okay, so I hadn’t predicted anything. Or known this would happen (though I wasn’t surprised to hear about my string of past lives). But finally it was my time to shine!

“Careful there,” a soft voice said. “That guy almost hit you.”

I opened my eyes. Again.

Now this was what an angel was supposed to look like. With newfound confidence, I let my eyes drag over my savior.

Just over five feet tall, she had silky black hair, soft hazel eyes, a button nose, and the kind of innocent expression that I usually only saw on the faces of pornstars before they got ravaged by an elephant dick.

I noted idly that she was still grabbing on to my hand. No doubt Uriel had sent her to pull me out of the way of Truck-kun, blessed be his name.

“You saved my life,” I said, as breathily as I could manage, clasping the woman’s hand in between two of my own. “How can I ever repay you?”

She blushed. “You don’t need to repay me. I just did what anyone would do.”

I nodded. This was good. She was playing the classic role of the reluctant hero, which meant that I was obviously supposed to play the role of a grateful damsel.

I glanced around with exaggerated, jerky motions. The entire crowd was looking at me. Huh, that was new. Well, I did almost just get run over.

“Follow me,” I said to my savior, pulling her along behind me. There had to be a private corner around here somewhere so that I could thank her properly.

“Oh,” she said, before quickly catching up to me, matching me stride for stride.

I pulled her into a conveniently located nook in the closest alley to the street. It was dark, and a bit smelly, and there was rotting garbage along either side of the alley, but for my purposes it was perfect. I sent up a short prayer to Uriel for delivering my first supplicant. Perhaps I had been wrong, and He was not as much of an aberration as I had originally thought.

“You shouldn’t dismiss what you did,” I said, pulling the woman by the arm until she was so close our faces were almost touching. The blush on her face was deep. It was, I imagined, the sort of blush women got when famous guys like Brad Pitt or Steve Buschemi started paying attention to them.

“My name is Chad,” I said, coming up with a new name on the spot. My name had been Doug, but Doug was dead now. All that remained was the appropriately named Chad. “And I won’t let you undermine what you did by saying that anyone would have done it. You saved my life, and I will forever be grateful.”

“I’m glad. That I could help you I mean. My name is Carla,” she said.

I let my unoccupied hand drift down to Carla’s bottom and gave it an appreciative squeeze. She gasped and I gave her what I thought was a charming, but slightly cocky, smile.

Her other hand flew up, no doubt to caress my face, and I caught it with the hand that wasn’t giving her bottom a thorough investigation.

“Relax darling, we have plenty of time,” I said. I gave her bottom a rougher squeeze. My cock was like an iron pole in my pants. I couldn’t wait to finally be rid of my virginity, especially to such a gorgeous woman. A dank alley wasn’t how I had imagined it (my beat-up Chevy had been my expectation) but, well, whatever. It was more about the partner than the place.

Then, Carla didn’t something I never could have expected. She headbutted me.

My head rocked backward, thumping against the brick wall behind me.

“What the hell?!” I cried. “I think you broke my nose!”

There wasn’t any blood, and my nose was perfectly straight, but still. That had hurt.

Carla looked as surprised by her actions as I was. “I’m sooo sorry. It’s just, you were being kinda weird you know? Like, we don’t know each other, and you just took me to this public alley and groped me. You seem really cool, and sexy, and smart, but buy me dinner first, you know?”

Isekai difficulty my ass. Women were still incomprehensible creatures, even now.

“So you don’t want me fondling your ass?” I asked, looking for some actual clarity.

“Not in a smelly back alley three seconds after learning my name,” Carla admitted.

“Fine. Fuck it. Whatever. Your loss,” I said. I left the alley without another word, just knowing that Carla was staring at my retreating back, wondering what she had lost.

So far, the big man’s new scheme was not living up to expectations. What would it take for a brother to get a little love?

I trudged back home dejectedly. Sometimes it was really hard to stay positive. Even with all the odds in my favor I still somehow managed to fuck things up.

This, I thought, was my lowest point. All the stars in alignment for me and I still couldn’t get my dick wet. What was the point of even being born? Sartre was right. Hell was other people.

I made a mental note to spend some more time browsing cool quotes on Goodreads. Maybe some girls would like that brainy shit.

I was so disillusioned that it was all I could do to make plausible excuses to the people calling out to me as I walked home.