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As he worked girlfriend it just a bit farther inside he carefully watched her body react, her facial expressions, her breathing, even how she moved her hips. He had had lots of opportunities now to learn her expressions of both minor discomfort and greater pain and he used what he'd learned to experiment more. He delighted when he could tell she was experiencing new sensations inside her where nothing had ever touched before and studied her facing expressions closely. He carefully added a bit of pressure on the handle of the rod delighting when a little more disappeared inside her. He even listened for familiar or new groans from her. He watched with excitement as she needed to move her hips, the arch in her back and her legs adjusted to the new sensations deeper inside. He couldn't resist carefully easing her legs a little higher and wider apart again Hardcore watching her face to determine if that increased or decreased the pressure inside. He even told her when he could tell, "There that helped a little didn't it? You need to feel it touch you deeper Holly" he added warning her he was going to push more. As he increased the pressure once again he heard her groans intensify and he felt more resistance on the rod, but suddenly, out of instinct she rolled her hips more pulling her knees up and he felt the pressure give way and the rod ease a few millimeters deeper which caused her to let out a hard exhale. He quickly replied, "That's a good pain slut, feel it touch you even deeper inside like you needed." He held the pressure there but didn't push more watching her still moving and adjusting her body. He delighted as she seemed to work her hips a little wider then push her knees a bit more towards her shoulders. He gave her a few minutes to adjust and delighted as she seemed to constantly move her body trying to find comfort. After she seemed to minimize her movements he began to carefully increase the pressure. For the first several moments it does not seem to go any deeper and just before he's convinced it can't go farther he sees her bite her bottom lip and push her ankles and feet wider and that tiny adjustment suddenly allows the rod to penetrate a few more centimeters. After the time he's spent with her he has been learning her sounds, expressions and reactions and when the rod worked that bit deeper he could tell it was causing her discomfort deep inside. He didn't try to work it deeper but he kept his hand on it keeping pressure on it. It was at that moment, more then any moment before that Roger realized just how much he enjoyed power and control over another person and watching them struggle with pain he was causing. She didn't even realize when he first made contact that fingers from his other hand had moved to her clit. But unlike any time before his intention was to stimulate and amateur pleasure her clit while she experienced pain in a place she had never felt anything before. Holly's body and mind were so confused. She felt a painful pressure deep inside where she didn't even know she could feel anything, black let alone pressure and pain. Yet the stimulation at the top of her sex sent different sensations deep in her body but in a very different way. "I can see the fluids just gushing out from you Holly. Do you feel then oozing down to your bottom? It hurts but you want...no...need more. I won't let you down Holly" he said his voice soft and for the first time he really focused on stimulating her clit wanting to fill her body and mind with confusing, contrasting sensation. While he had zero desire for her to feel pleasure he hoped he could hard fuck convince her that the pain was pleasurable or sexually stimulating. Just to have a bit more fun after he was confident his clit stimulation was working at making her feel pressure even with the painful pressure deep inside her sex, he decided to try one more thing he thought to be cruel and he stopped rubbing her clit and used that hand to tap, tap, tap, over and over on the end of the metal rod. “Did everyone see that? The innocent little girl I remembered playing with barbies was sitting across from me trying to scare me out of my job with a story so terrible and horrible that it would have scared me if it weren’t for the fact that it was my little sister telling it. My lungs were absolutely killing me from panting so hard and my face was really stinging from the cold, not to mention my wrists from the snow getting under my gloves. Hard to do when I know you're out with him. “It might be a good idea to black close the door, Paul.” I spoke again once we had privacy. "Just checking that your girlfriend reflexs were nearly back to normal. Behind hard fuck her, James had his cock out. I imagined slipping myself into her tight little holes, every single one of them, and tearing them up as Hardcore my engorged member destroyed this little whore. I'm sorry. Jim growled at them but carried on walking towards us. What do you think boss?” Jennifer asks. She turned to the others. YOUR COCK IS FILLING MY SWOLLEN LITTLE PUSSY UP WITH YOUR CUM. Jill opens the bedroom door. Who was I to judge? No one seemed to notice my short dress and un-crossed legs. The first dog had moved to stand very close to her face and opening her eyes, which she had previously screwed tightly shut in fear, she could see the huge angry red cock hanging down. I just needed to push him a little more and he would fall in line. Her duties weren’t onerous amateur as all she had to do was care for Jeff and make his life as comfortable as possible, the cooking and cleaning was done by other staff who the Thomas’s employed in their large sprawling mansion. Tommy has to be careful what he says to her, if not she will get too turned on and attack him in a heartbeat. “What? The only dilemma she encounters on a nightly basis is that Dr. Cadbury is now on the night shift rotation and makes it a nightly habit of hitting on her. Misty and the Old Guy (Part 2) He said you new aren't you? She pulled back, caught a breath, and swallowed again.