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"He quickly did as he was instructed, hoping his new Office Manager wouldsoon stop this humiliating ritual."Good. I can see you're wearing a panty-liner, and that reminds me," shesaid, reaching into her handbag. "Here's the diary you purchasedyesterday. Very girlie. I've took the liberty of filling it out with aperiod tracker for you."She smiled, aware his small penis was hardening, tenting the panties."I hope you're not going to have heavy flow again," she said, brushingher palm lightly against his bulge.He flinched away as pre-cum oozed onto the panty-liner."Get dressed," she said and left his office for her own desk.He pulled his trousers up with relief and sat down, hating every secondof his humiliation. He could handle the women's clothing privately, evenpublicly to an extent if he accessed a part of his mind and shut the fearout. But he hated, despised, Kelly's embarrassing games.He opened the diary, smiling without humor. Pink pen clearly indicatedthe start and end of each. I used a small amount of vegetable oil from the kitchen to lube up her asshole and anal canal. I also used some to lube head of my cock that I had now positioned at her backdoor entrance. I slowly began to press the head of my cock into her anal ring. Now., I said gently in an almost whispered voice as I concentrated on not hurting her. She tried to push the air from her ass, but my cockhead was partially blocking the flow. This caused her asshole to open a bit wider than it would have for a normal fart. This was the opportunity to make some progress in getting her loosened up. As the fart escaped her rectum, my cock slowly pushed further inside her. How does it feel so far? I asked her. Surprisingly, its not hurting this time. But, as of now cant really say I enjoy it either. she said with a look of disappointment and indifference. Thats okay sweetheart. Im not really even half way in yet. The worst of it is over. When I get you loose enough to actually FUCK you, you might change.
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