Emily was sobbing as Jack lined his cock up with her ass. She began to squirm as she felt the head pass her tight ring. There was nothing she could do but lay there , She was cuffed in place and they threatened to hurt Katie if she resisted. Once the head breached her ring Emily yelled out in pain "Noooo Please stoop it's too big". As Jack fed a little more cock up her ass he smiled down at her and said "I can stop with you if you want me to take Katie instead". Emily knew she did not have a choice in the matter and sobbed as she said "Please fuck my a..s...s....". Jack kept pushing into her tight passage way until he felt his balls hit up against her cunt. He knew he was all the way up her ass at that point. With a ear to ear grin Jack says to Emily "Now that you took all my cock get ready for your fucking". Jack knew it was going to hurt Emily as he pulled back his cock, He felt the intense tightness of her once virgin ass grip him. Not caring about the pain he was causing her Jack put both hands on Emily's shoulders, Looked down at her tear stained face and rammed his cock all the way back up her ass. Emily grunted with pain as Jack was pulling his cock back, She wimpered "Please go slooowww" as he forced his cock back up her ass. Jack repeated the same thing five or six times till she loosened up a little. After Jack felt she was loose enough he began to piston his dick in and out her her ass riding her as hard as he could with each thrust. Jack could hear his balls smack her twat as he was reaming her hole. Emily would sob as he did this every so often she would plead with Jack "Please not so hard". That was a turn on to Jack and he would ream her harder, Jack then felt his cock ready to blow and wanted to humiliate Emily once more before he shot his load. Jack asked Emily "Were should I cum up your ass or in your mouth and don't forget to say please". Both options were revolting to Emily, but she knew she had to pick one. With pure agony in her voice she wimped "In my ass please". Just as Jack heard the words his cock swelled up and he shot his overflowing load right up her virgin ass. Emily groaned as she felt it in her bowels, It burned where Jack had ripped her.
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