Kinktober 2020; 4. Extreme

 

Can you handle the EXTREME!

To Dan the simple hand printed poster was a personal challenge, almost an insult. He certainly could handle the extreme. His whole life had been a series of increasingly daring challenges. From surfing monster waves and swimming with sharks to climbing the jagged peaks of the Himalayas he'd always sought the next challenge. Adventure was in his blood pushing him forward, onward, upward, where lesser men couldn't dream of following. He couldn't imagine what could possibly be "EXTREME" in a place like this. A rundown store in a dingy corner of a half empty mall. Curiosity, more than anything drew him in despite his better judgement. A bell jangled as he pushed open the door summoning an unkempt old man from a back room. 

"Hello, welcome to the world of the EXTREME!" The old man scratched at his grey bread as he recited what was clearly a rehearsed script "Prepare to be astounded. Your mind will be expanded. Your world will be upended. Your limits will be discarded. Here at the emporium of the extraordinary."

Dan stared at the old man as his patter ran down an uncomfortable silence growing between them.

"Forget it," he muttered, turning to leave.

"Wait Dan " the old man's voice stopped Dan in his tracks "If you leave now you'll never know."

"Know what?" Dan asked, reluctantly allowing himself to be drawn back into the conversation. 

"Know what it is we do here of course," the old man said with the smug smile of a salesman who knows he's hooked his mark "You've been chasing rumours of our unique service for most of a year, are you really going to walk away now you're here?"

Dan's eyes narrowed at this. How did this man know why he was here, his name even?

"Okay, I'll bite," he said "what exactly do you do?"

"Excellent," the old man beams, "now normally I'd talk you through our process but in your case I think it might be best just to show you."

The old man waved his hands in the air tracing a complex pattern Dan couldn't quite follow. There was a brilliant flash of light and everything went black.

When Dan came back to his senses he found himself alone in a motel room. The room was small but tidy and afternoon sunlight streamed through the single window. None of that mattered to Dan though as he stared down at his own body.

"Holy shit!!" He squealed "I'm a fucking girl!"

It was ridiculous, impossible, absurd but it was also true. He was a woman, slim with smooth pale skin. There wasn't a trace of the deep tan and strong muscles he had spent so long earning but his shoulder still bore the tartan tattoo he'd gotten after completing the three peaks challenge the first time. He was smaller now too a petite 5 foot or so if he had to guess although his shifted perspective made it hard to gauge with any certainty.

 He poked cautiously at the small firm breasts that now adorned his chest watching them rise and fall in time with his breathing. Slowly, reluctantly his gaze moved further south, past his flat stomach to the point where his thighs met. 

There was no sign of his usual equipment there just the slight swell of a smooth feminine mound.

"Oooh crap," his voice wavered on the edge of panic "how is this even possible."

Firmly he took hold of his emotions. He hadn't given into panic when his chute failed at ten thousand feet and he didn't intend to start now. Strange as this situation was he didn't seem to be in any danger. 

He wasn't in any pain, in fact now his initial shock has worn off he feels rather nice. A cool breeze made his sensitive new nipples tighten. He touched them and gasped as the brief caress sent a hot wash of excitement rushing through him.

"Oh, okay," he sighed, allowing his hands to begin roaming over his body. "I guess that old man wasn't lying about offering a unique experience but I don't see what was so extreme or challenging about feeling up a cute girl from the inside…"

As he spoke he felt something solid under the pillow where he lay. Pulling the object free he found himself holding a huge dildo! It was obscenely large. As long as his arm and so thick he couldn't even wrap his hand around it. Attached to it was a handwritten note

"how about this for an extreme challenge?" It said.

"You have got to be kidding me!" he said shaking his head. 

The thought of this monstrous thing being used to ravage the delicate body he currently occupied was… Well it was just… It was actually kind of exciting he was forced to admit. His pussy tingled as if agreeing with him and his curious fingers found it wet and eager for his touch.

"The hell with it." He declared "I've never backed down from a challenge in my life and I'm not about to start now."

He took a firm grip on the outsized phallus but he didn't use it just yet. Experience had taught him that preparation was key in all kinds of endeavors and that went double in the bedroom. Instead of plunging straight in he caressed his female body relishing the way it responded to his experienced touch. He'd always enjoyed foreplay when he was with a woman but this? Touching this woman's body and feeling its responses as his own, that took things to another level.

Soon the dildo was pressed against his pussy as he teased himself with it, letting his excitement build as his juices coated its surface. Only when the hot ache between his legs grew almost unbearable did he drove it home. 

A wordless moan of ecstasy came from his mouth as the thing stretched his sex to its limits. The delicious, impossible, wonderful sensation of being filled for the first time overwhelmed him. Without needing his conscious command his hips rose to meet it, inch after inch of the rubber shaft sliding against the tender nub of his clit. 

In moments his climax broke over him. He shuddered and thrashed uncontrollably the grip of his first female orgasm. It was so much more than anything he'd experienced as a man. It was like he was cumming with his whole body!

It felt like a long time before the waves of pleasure subsided enough for him to regain full control of his limbs and carefully eased the dildo out of his now sore and over stimulated pussy. He was just thinking that the rumours he'd heard about this place didn't nearly do it justice when he found the second note.

"Hmm, not bad for a warm up" it read "I think now you might be ready for a real challenge…"