A Hundred Times: Ascending With The Strongest System - Chapter 6 - 5: Further Deeper

When Demon Lord, Syryn Nigh'hart, found that he had gone back in time and turned into his child self, he had assumed to do better with his second life. Commit smaller crimes, keep away from burning villages and inciting other demons, contribute to society, abide by most laws, you know? But then the hero, his old friend, had to fall in love with him and ruin his plans.

Goddess, I cannot take responsibility for your champion, Rowan Windwalker, getting bent. Please don't strike me down!

#Gold Tier winner of WPC (forgot the contest number)#y'all this shit gay so don't go walking in expecting it to not have men sucking faces#N̶o̶ ̶h̶a̶r̶e̶m̶(my dumb self thought harem means mc marries many lovers)#Reformed and immature demon lord (but he's nice now okay. He isn't psycho.) #Hero is an extremely patient man for putting up with the demon lord's nonsense # MULTIPLE POTENTIAL LOVE INTERESTS #Slow Romance#Slow like you have to wait for around 40 chapters (smut too) before it starts #Patience is needed #Lots of it#alternate day updates because I have to study#english is neither my first nor second language so bear with me#The cat is not the ML ಥ‿ಥ some of you are getting the wrong idea.

Adam's life has been a huge disappointment.Growing up, he was a shy kid with no confidence; he had no ambition; he had no plans for the future.He didn't realize the time flowing by until one day he hit rock bottom.His wealth was taken away from him. He had nothing.Now he lives in a single-room apartment, he is making barely any money; he has no friends, no family, and no lover. He is all alone living a pathetic, miserable life.He is so pathetic that he died in his own apartment, slipping on a beer bottle.But fate has other plans for him. He didn't die but ended up back in the past with an upgraded body.Now, with another chance in life, he is determined to strive for greatness.____________________A/N - This is a smut-focused story. Expect a lot of sexual scenes.

As a promise, he went out into the world as an assassin. 3 years later, after becoming the Supreme Assassin, he gave up on everything he had and returned to the ranks of ordinary people. But one day, Kismet, a mystical game created by the National Research and Development had appeared.

Enigmatic hands, spectral frame, and one cunning strike just like the swing of the Grim Reaper. The Supreme Assassin takes on the mystical world, and how his legendary tales sets off, progressively ascending the altar to becoming the best.

- Description from Novelupdates

Coming to my senses... I find myself a desperado.In the depths of azure, black sails flutter.Treasure gleams, blades ring out.Pillage, slaughter, irreverence towards the gods.Youth fades swiftly, all but meat and wine for pleasures.[Slice of Life][Romance Simulation][Business Simulation]