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Yeah but the fantasy mom would see him as a baby but if his girlfriend became the fantasy mom she'd no that before they reincarnated this would be weird and she'd use that to embarrass him for fun
Well what if he has a sister who was secretly sleeping with his girlfriend in secret and after they arrived in the new world together they end up meeting his sister who also died and reincarnated there so now both girls treat the protagonist as their baby
Ok who would you want it to be maybe he has a girlfriend who becomes the dragon queen and his new mom and she could be lesbian and was going to break up with him when they both died and now in the new life she gets to baby him while finding another dragon girl to be with