This week's prompt was proposed by @tigger_sub.The word that she proposed was "Training" I am afraid that I used the prompt a little differently that perhaps she intended but I am sure that you will all enjoy the results.
Josh hated training courses. The idea of sitting on uncomfortable chairs in small rooms with freezing air conditioning listening to boring presenters who didn't have the first clue about what it was like to work in a real job in the real world just made him irritated. Even though his boss knew how he felt about training courses he still found himself sitting on an uncomfortable chair in a freezing room waiting for the presenter to turn up. His boss had given him some kind of line about everyone needing to complete a personal development activity for their annual review. In an attempt to warm himself up he got up and helped himself to the coffee sitting in the corner and then checked his watch, 8.30 am. He was surprised that he was the only person who seemed to turn up. "That would be right," he thought, "I get stuck here in a stupid course and there isn't even another person to talk to." He wandered over to the desk and selected a chair just before a woman with flaming red hair walked through the door carrying a thick leather briefcase.
"Hello," she greeted him before she made her way to the whiteboard at the front of the room.
"Hello," Josh replied, with his eyes glued to her ass as she bent over to look inside her briefcase. The fabric of her skirt stretched enticingly over her full round butt. "It doesn't look like there are many turning up this morning," he continued, unsure of what else to say.
The presenter turned to face Josh. He had to remind himself to keep his mouth closed as she walked towards him. The neckline of her blouse stretched open to display full round breasts that looked like they were about to fall forwards. Stopping in front of him she leaned forward on the desk until Josh could almost see her nipples. "That is OK," she smiled at him. "I prefer small intimate groups." As if it was the most natural thing in the world she slipped her butt onto the desk in front of him. "So," she continued, completely business like. "Today is all about your personal development and pushing your boundaries," her voice dropped slightly as she leaned forward and touched the side of his face, letting her finger trail down the side of his neck, "Tell me about some of your boundaries Josh."
Suddenly it seemed as if Josh's pants were not big enough for his cock, "Uh I don't know," he stammered fidgeting in his chair, trying to find a position that put less pressure on his throbbing cock. In front of him the presenters fingers nimbly popped open a couple of buttons on her blouse to reveal a very low cut bra and even more of her impressive cleavage. "What kinds of boundaries were you meaning?"
"Well this course is about personal development," the woman replied as she continued to unbutton her blouse. Even though Josh had been freezing earlier he suddenly felt hot. "So I was thinking personal type boundaries," The woman slipped off the desk and stood in front of him, "like taking your clothes off in front of a stranger." To emphasise her point she shrugged out of her blouse and let it slide to the floor, "Have you ever done that Josh?"
Josh fidgeted, not sure where to look. "No," He replied quietly unable to take his eyes off her breasts.
"Would you like to?" The woman reached behind her waist and Josh heard the sound of a zipper before her skirt started sliding down over her hips.
"Maybe," he replied glancing towards the door.
She followed his gaze, "It is OK," her voice was comforting, "I made sure it was locked so that we wouldn't be disturbed," the skirt joined the blouse on the floor. She looked so tempting standing there in front of him in her underwear.
On an impulse Josh stood up and began unbuttoning his shirt. "What the hell!" he grinned as he shrugged out of his shirt and followed suit with his jeans. He stood before her with his cock straining against his boxers unsure of what was going to happen next but determined to be open to whatever came his way.
Taking a step forward the woman reached out and stroked his cock through his boxers. Josh held his breath, wondering when he was going to wake up. It had been so long since a woman had touched him there that he was sure that this had to be a dream. The woman slipped her hand under the waistband of Josh's boxers and curled her fingers around his shaft. "So you haven’t answered my question," she moved her hand slowly up and down and Josh began to wonder if he would be able to contain himself, "Do you have any boundaries?" She moved until she was close enough that Josh could feel her breath on his neck. He shuffled his feet as her hand slid down over his testicles cupping them gently before continuing further back towards his ass crack.
Josh felt his butt cheeks tighten as her fingernails scratched the skin behind his testicles. His cock throbbed in response, taking him completely by surprise. Her fingers slid further back, towards the forbidden zone. The place that he had always maintained was outwards only, except in the deepest darkest corners of his fantasies, ever since he had seen that image. Her finger stroked around his asshole tantalising him. His body betrayed his mind, opening itself up to her caresses even as his mind screamed out to tell her to stop.
For the first time he noticed her eyes, the glittering lust he saw there. "I will stop any time you tell me to Josh," she whispered. "But until you say stop I am going to keep on exploring,"
"I don't want you to stop," Josh was stunned to hear his own voice say those words.
She pulled away from him slightly and reached out for the waist of his boxers. "Maybe we should get rid of some barriers then." She slipped the garment down over his hips freeing his cock. "Mmmm," she bent down and tasted him briefly," Josh moaned sharply, alarmed that he would shoot jizz into her mouth and spoil the moment but she released him. "I do like sausage but I am after more exotic fare today."
Quietly she moved to stand beside him, running her hands down his naked back to cup his butt before she slipped her finger lower to caress his butt hole. Josh took a deep breath as she smeared some lube and slipped her finger inside him. Sensation exploded through him as she moved her finger gently in and out. His cock was like a rock in front of him and he couldn't stop himself from gripping his own shaft.
"That's it," the woman's voice whispered in his ear. "Relax and enjoy the moment."
Josh nodded, frowning in concentration as sensations he never imagined possible sizzled through his body. The woman pushed her body against him, rubbing her crotch against his thigh as she finger fucked his ass. Josh's head was spinning with pleasure.
"Would you like more?" her voice interrupted him.
"Yes please." He heard himself say.
She removed her finger and there was a pause before he felt the cool pressure of something else opening him more. He pushed back against the implement eagerly, still surprising himself with how much he wanted this. There was a moment of slight discomfort and then the pleasure ripped through him. His hand gripped his cock hard as she fucked his ass spreading him further than he thought would be pleasurable. His whole body tingled and he felt something building. It was like an orgasm but at the same time not. Before he could stop it he exploded, groaning as cum covered his fist. His whole body spasmed in pleasure before he collapsed forward on the desk still twitching with aftershocks. Feeling completely dazed he turned his head towards the woman, She sat on one of the chairs with both of her feet up on the desk. Still recovering Josh watched as she fucked herself with a thick pink dildo. Her fingers moved quickly on her clit as the pink plastic moved in and out of her slippery wet cunt.
Her movements became more frantic as Josh watched until her mouth formed a perfect O and her body arched out of the chair. As she relaxed and slumped into her chair a huge smile spread across her face. "Well done," she congratulated him as she came back to life. "I think we can definitely say you have pushed a boundary or two today."
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