Kigenzen 10000-nen no Ota
The Otaku in 10000 B.C.

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both have loser MC (10,000 BC has cooler and more likable MC than 2200 AD) both have otaku MC both MC did it with almost all girl in the manga both have some sort of conflict both use s*x as power source both explain certain sexual acts (10,000 BC it's all the firsts in 2200 AD its the absurd new ways) both crated by the same author 

Both are in a kind of Stone Age where both characters use their "superior modern knowledge" to solve problems. THE PHYSICAL: In Dr. Stone, the main character uses Scientific Knowledge to build things that make Stone Age Life easier, little by little (recreating lost technology e.g. soda, alcohol, lightbulb, transportations, you name it). THE METAPHYISCAL: In Kigenzen 10000-nen no Ota, the main character uses modern knowledge of sexual techniques to "solve problems". Unlike in Dr. Stone, the main character here does not create modern, physical things. He forms relationships to the tribes through sexual intercourse with the prehistoric females using a variety of positions unheard of before (e.g. missionary, sixty-nine, cowgirl, usage of dildos). Basically, if you want a Dr. Stone but hentai, read Kigenzen 10000-nen no Ota. I recommend these two if you want to see a clever use of modern knowledge in a place that is similar to the Stone Age.  read more 

One man having multiple relations with many partners. Even though the two stories are set at very different time periods both main characters find themselves waking up at different periods of time trying to grasp the dyer situations they are in. Both mangaka's show amazing display of artwork, unveiling some sensual scenes between the characters.  

Both stories involve time travel through the periods, while Kigenzen's male protagonist go's into the prehistoric times, Hime Monogatari's female protagonist go's into today's time. Both narratives are very humorist in showing what happens when you put two extremely different ways of life together. Both manga's have impressive art work and notable H rated scenes that look down right splendid in each page. 

Both main characters find themselves in custody by busty arrogant women who have hidden motives for keeping them under lock & key. Both manga have interesting stories and great art work with good detailing on the male and female characters. Both manga have comedy, romance, and H-rated content .