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Shen felt as another pup began to slowly crown, stretching his cloaca wider then it had any business stretching. He squeezed his eyes tightly, his face crunching as he pushed the child's head out."Breath Shen" He heard Boss Wolf familiar voice chime, realizing he had forgotten to breath as he was squeezing the child out. Shen took in a deep lung full of air, his swollen belly rising, then falling again."Unnf, ugh" Shen grunted as the pup's head popped out, relived that the hardest part was over yet again. He tried to enjoy the minor decrease in pain as the baby was pushed into Boss Wolf's waiting paws. But he was reminded all to soon that it couldn't last, he could feel as the pups still enclosed in his stomach squirmed impatiently, fighting to be the next one out."d-damn" He curse aimlessly to no one, no one could help him after all' Even if Boss wolf was willing there was nothing that could be done to pause the labor. He leaned over on his stomach and pushed hard as a painful contraction came, one more child pushed it's way into his birth canal."f-fuck" he felt the pups in his stomach push hard again their encasement, causing his belly to protrude, he rubbed his wing up and down his belly, hoping the loving gesture would calm them although it hadn't helped stop their stirring yet.Shen gave another hard push, not waiting for a second contraction as the child's travel seemed painfully slow, he just wanted this torment to be over, the pregnancy had lasted all to long, now he just wanted the things out. Even with a litter of this mass Boss wolf would not be satisfied, but he needed the general, one wave of his paw and the canons construction stopped, and his army would turn against him."ahh-AHHH!" Shen screamed as the baby made it to his wore opening. As he pushed it became apparent that this would be the alpha of the litter, as it was much larger than the rest. Some of the pups were even malnourished as his body could not provide enough food to feed them all an acceptable amount, but was able to tide them over till now.Shen screamed again tilting his head back on the chair and squeezing his wings tight against his bloated midsection. "Ahhhh!! Get it out!" He wailed to boss wolf, doing all he could to push the monstrosity from his body, harboring a great deal of disgust with his new children, how could they do this to him, hurt him so.His entire body shook as he pushed as hard and long as he could manage, the pain flowed through his entire body, making him shake and stir. His cloaca felt like it was going to tare, it couldn't seem to fit the large head passed, and for a moment Shen swallowed with worry at any complications that might arise."Comon Shen, push a little harder" Boss wolf sounded all to delighted in this moment, he brought his paw up to Shen's cloaca, sticking a finger inside, past the child's head as he caused Shen to wail, he swore his body had torn at that moment. Wolf carefully moved the child along until it's head became unstuck, and with hard, constant pushing began to leave Shen's body.Tears fell from Shen's exhausted eyes as his cloaca felt as if it were burning, soon the child's head had fully emerged and Shen let out a long breath. Carefully Boss wolf pulled the body from Shen with slight only resistance, Shen momentarily groaning.Before he could rest he felt his birth canal opening once again, promising new pains and struggles that came with each individual child. He cried tears of exhaust, knowing he was far from done, he could feel the rest, multiple children still moving, filling his stuffed stomach to the brim, waiting for their chance to emerge from the womb and have their own opportunity to hurt mommy.