MTL - Black Technology: Starting From the Space Jumping Machine - Chapter 50 through the stars

Two hundred lifetimes! Two hundred miserable deaths! Leon is a 27-year-old man who experienced a rollercoaster of 200 reincarnations within 180 days. He was so unfortunate that he even died once when he was about to masturbate to hentai! Each death carries the regret of his virginity as he keeps dying without getting a chance to fulfill his only wish…losing his virginity. But his luck finally changes after the 200th death, and he encounters the Goddess of lust, who makes him an offer to be reincarnated with a gift. (Ding! System awakening…) (The super Harem system…) (Ding! The host has seen the secret garden of a heavenly beauty, reward!) (Ding! Mission issued: have sex with the sex mistress!) “All heavenly beauties shall be mine!” Join Leon on his journey to enjoy life to the fullest as a virgin who got his hands on a sex hack, conquering heavenly beauties and even Goddesses! Additional Tags: R-18, HAREM, ACTION, ROMANCE, ADVENTURE, REINCARNATION, SYSTEM, Overpowered Protagonist, ANTIHERO, SMUT

You are the ruler, I am a subject, you want loyalty, I’ll give you loyalty. You are the ruler, I am the subject, you want my sacrifice, I will sacrifice for you. This lifetime, we’ll only be ruler and subject…… cannot become the one who accompanies you to experience everything.

A deposed empress, a failure of a substitute. Charging into battle, he was the emperor, and she, his general. But within the intimacy of their military tent, he was her husband, and she, his wife.

But everything was star-crossed. For the one he loved the most, he would push her into hell again and again.

- Description from Novelupdates

Madeline Celeste d'Aumont is the first daughter of Duke Aumont and Duchess Louise-Marie d'Aumont who has been engaged to the Second Prince of Pays Des Abrutis since she was a child. The Second Prince decided to marry a woman closer to his own age and broke off the engagement to Madeline who was left with a broken heart and a reputation as being an unwanted woman even before she was an adult. The Duke decided to help his daughter regain her confidence and reputation by sending her to the Academy de L'échec.

Ito Aoi was the son of a Kendo master who ran a dojo in downtown Tokyo. One day while crossing the street to get some Yakitori, Aoi was hit by a delivery truck and woke up as the trash first son of Duke Montfort, Guy de Montfort. Duke Montfort also sent his son to Academy de L'échec only Aoi instantly recognized that he was now living in the world of an Otome Game that his sister loved to play and talk about all the time. Aoi recognizes that Madeline is the villain from the game. Aoi also recalled his sister saying that Madeline was terrible in the game, but is she really?