Friday Flashback – Personal Development

From the vault of Erotic Adventures comes this little gem. It is happy to see the light of day again. I hope that you all enjoy it.

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.”

The Washing Basket Part 2

Several months ago I posted The Washing Basket Part One  of a story and only just realised that I left you all hanging. As part of my Christmas holiday clean up here is part two. You may need to refresh your memory of part one and you can do that by going here.

“So,” her voice crackled like ice across the room sending a chill down his spine. Automatically his eyes travelled to the space under the bed where he knew she kept her implements. His buttocks twitched under the skirt, inside her panties; HER panties. The look on her face left him in no doubt, she was not impressed and he would be punished. Deep inside a little flutter of excitement made itself felt tempered only the slightest bit by fear. What would his punishment be? It had been a long time since he had felt the sting of her palm on his bare buttocks but something in her tone, the way she held herself and the light in her eyes told him that he was going to be receiving something much more than a mere spanking. 

“I see that you managed to amuse yourself while you were waiting for me.” Her eyebrow raised. Howard was not fooled. He knew that glint, guilt flushed through him, he had betrayed her trust. Maybe she wouldn’t merely punish him in the way that balanced on the fine border between pleasure and pain. Maybe the consequences for his adventure would be more serious. The elation he had felt at the thought of a punishment evaporated and the cold chill of fear settled in his belly.

“Do you like wearing women’s clothing then Pet?” She walked towards him slowly. For the first time he noticed the collar in her hand. His heart skipped a beat, she did intend to punish rather than banish. She stopped in front of him, and stood for a few moments looking into his eyes. Her expression was unreadable. For a few moments he looked back at her hungrily, it had been weeks since he had seen her and he wanted to take in every detail of her face but her eyes held him captive. 

Placing the collar around his neck, she broke the spell, “You haven’t answered my question.” She whispered as she fastened the buckle, smoothing the strap and making sure it sat comfortably on him.

His throat felt as if it had closed up, “Yes Miss,” he managed to reply in a hoarse whisper.

She snapped the lead into the ring at the front of his collar, “And so you thought you would wear my clothes,” she pulled his head downwards so that his face was pushed against the bed. Every nerve in his ass was stretching out of his skin, straining to feel what was coming next. He felt the fabric of the dress being lifted upwards to expose the white cotton of her knickers stretched over his buttocks. The crack of her palm against him filled the room, the sting shot a tingle of pleasure/ pain up his body making him grunt into the bed. 

“Did you like the feeling of the dress over your cock?” She asked as she rubbed her hand over the place she had just slapped sending more tingles through him. When he didn’t reply immediately she clenched her fist digging her nails into his skin.

“Yes Miss,” his voice came easier this time even though his body was coiled with tension waiting for the next blow.

He was not disappointed, a second and third sting resounded through his body before he felt tension in the lead as she bent down to pull her case from underneath the bed. With the sting of her palm slowly fading he listened intently to the sounds of her snapping open the lock and rummaging through her implements. He heard several things being placed on the bed beside him. He desperately wanted to turn his head and see what she had put there but even more he did not want to interrupt the flow of what she had in her mind. Resolutely he kept his face planted into the bed. 

Her hand smoothed over his ass again before she pulled the leg of the knickers across into his ass crack. The elastic cut into him, squeezing his testicles together and stretching the fabric tight over his engorged cock. “Did my knickers feel nice over your cock pet?” She asked as she scraped her nails over the mark her hand had left.

This time he didn’t hesitate, “Oh yes Miss,” he almost wriggled in pleasure as he remembered the feeling of her dried juice scraping against his cock. 

The sting of her palm on his bare skin was so much more intense than her hear earlier blows. “You dirty, dirty boy.” She replied. There was a pause as she bent down and picked up her small whip and then another intense flash of pain as she flicked the thin ribbons of leather over his bare red ass cheek. His grunt of pain was echoed loudly across the room. 

“If you like dressing like a woman then maybe you deserve to be treated like one,” she spoke through her teeth as she flogged him several more times. Howard clenched his fists beside his hips, his ass felt like it was it was on fire and he was starting to wonder if this would be the day that she pushed him too far. As always though she stopped just as he was reaching that point. 

Her hands left his body and Howard found himself straining his hearing to determine what she was doing. There was the riiip sound of Velcro tabs being adjusted. Her first touch was cold and wet as she slipped her finger into his ass. He gave a small moan of pleasure in response. 

“I think if you want to dress like a woman then you should be fucked like one,” she pushed his legs apart and moved between them. Howard held his breath as he felt himself being opened by the dong she was wearing in front of her. The elastic of her panties pulled even more tightly over his scrotum and kept his cock even more constrained but he didn’t care. Every sense was focussed to the pleasure of his ass being stretched and she pushed herself deeper into him. Finally her pubic bone came to rest against his ass.She stood resting part of her weight against him with the plastic dildo buried in his ass for a few moments, ” would you like it hard and fast like this,” she pulled out of him and plunged back in, slapping against his ass several times. Her hands gripped his hips tightly distracting him briefly from the intense feeling of being fucked. Suddenly she stopped, holding herself still with the tip of the dildo resting against his hungry asshole. He almost cried out in desperation as the sensation of pleasure drained from him. She was so still he could almost imagine she had left the room.

“Please,” he whimpered, fretting that she was going to withdraw from him and that she would leave him like that, crashing down from the heights of his pleasure. 

Then she pushed herself into him ever so slowly, sliding in stretching his ass open ever so slowly until her hips were resting against his ass again. 

“Or slow like this.” Her fingers gripped his hips as she began to penetrate him ever so slowly. The sensation was surprisingly intense, as if she were stretching out his pleasure making him ache for more but at the same time frightened of her slamming into him. 

“I don’t know,” he whispered, unable to think in terms of his desires. He wanted it all; all of her and every piece of pleasure or pain she desired to give him. He was completely at her mercy. 

“I like it fast,” she decided slamming her hips against his ass. 

The room was filled with the sound of her slapping against him and his groans of pleasure. He could feel the orgasm building up. He tried to dismiss it but the intensity of it was almost too much for him. Suddenly he felt a sting of her palm against his skin. For a millisecond the pressure of his orgasm was gone, but then she slapped him again. He was so lost in his experience that he couldn’t tell the difference between pain and pleasure. Every stroke from her cock, every slap of her palm, the cutting sensation of her knickers around his balls, everything was just sensation layered upon sensation. 

“You like being fucked like a woman?” She asked harshly in between slaps.

“I do, Miss, I do.” He replied with heartfelt fervour. 

“You are a dirty, dirty boy.” She slapped him again, harder. “I should tie you up somewhere and invite all my friends around so that they can all come and fuck that slutty, dirty ass of yours,” the image of being treated like a plaything for Miss and her friends was almost too much for him.

“Please Miss,” he whimpered, gritting his teeth to keep control of his body. Involuntarily he pulled away from her to prevent his orgasm.

Angrily she flipped him over and stood over him while he sat on the bed. “Suck my cock and wank yourself until you cum.” She commanded. The look in her eyes sent a small quiver through him. He didn’t argue. As he put his lips around her rubber cock he could feel the buzz of the vibrator sitting against her cunt. Se watched his hand wrap around his cock and begin to stroke intently. Her body spasmed slightly and a trickle of moisture ran down her leg. It was too much he let go of himself and groaned loudly as his cum jetted out of him covering his belly and his hands.