"Shouldn't it be lubed?" Roberu asked. He was wearing his old middle school uniform that barely fit anymore.
"Of course not, you're not a weakling, are you?" his “oneesan” answered.
"What?" Roberu was lost. "But won't it hurt?"
"It will. That's part of the experience. For what would you learn of this otherwise? Wrong kinds of thoughts. Life hurts. You're still young” – it was hard to forget that the woman was half a decade younger than him – “and on the cusp of adulthood. There're still fantasies in your head. Oneesan is here to teach you some truths about life and one of the most fundamental of those is that life hurts.”
Roberu was eyeing the strap-on Suisei was attaching on her waist. It seemed unnecessarily big, certainly bigger than his. Fear was rising inside him. But the woman droned on falling into an archaic speech pattern:
“This is a lesson the ancient samurai taught to their pages. You want to grow up to be like them, don't you? You want to be a strong man? Then you have to deal with pain. Do you think the ancient samurai learned this by using lube?”
She seemed to have gotten far too into her role here and their play had switched into something else entirely. But Roberu could just nod as she approached him and pulled his pants off.
“Come now, on your knees. Bite the pillow if you have to, but this is something you have to endure in order to grow. Relax, take a deep breath.” Her gloved fingers entwined themselves with his, pressing him against the bed.
He concentrated on his breathing while his oneesan put her thing against his anus, her other hand moving to take a strong grip of his waist. He could feel it most clearly, realizing that there had never been anything like it pressing against his skin there, the object feeling most foreign – and then, suddenly, the sharp pain of of a rectum riven. He let out a yelp and and through the pain tried to form a word – only to realize they hadn't agreed to a safeword.
