Roleplay Phone Sex – Holly’s Promiscuous Cheerleader Days – Part I

Welcome to my Permiscuous Cheerleader Blog where I tell you a story from my naughty College Cheerleader days.

  “Hey Holly,” Jessie said eyeing her up and down. He stood to her left, a few tepid feed away, over six feet of hulking man, sweaty and still sealed within his football gear.

Just the way I like them.

“Oh, hey Jessie.” She wondered if he could see how soaked the bench was.

“So, uh, you wanted to see me?”

“Yes, Jessie. You won us the game. You know what that means.” she said her cheerleader outfit hugging snuggly on her body.

He swallowed. “Uh, yeah.”

Holly stood up and gently grabbed Jessie’s hand. “Step into my office with me please.”

“Uh, okay.”

And so the Permiscuous Cheerleader ritual began.

The Howlers formed lines on both their sides, watching as she carried Jessie along to the largest stall. It doubled as a shower, giving ample room for whatever sexual debauchery her and her Howler of choice decided to indulge in. It had been made up just for her comfort: a wool rug on the floor, a fuzzy pink seat warmer over the toilet, and a small shelf in the corner for her candles. This was a special, secret place, just for her and her Howlers.

“Don’t bust a nut too quickly Jessie,” she heard one of them tease. She could tell he was blushing; his hand was hot with a quickening pulse.

“Show Holly a good time man,” she heard Kyle counter with encouragement. “Bust her open for all of us. You deserve it.”

He does, she thought. It had been some time since Jessie had first dibs, and she wanted to make it special for him.

Holly pulled Jessie into the stall and locked it behind her, turning everything on the outside into white noise as she steadied herself for what was to come.

“You know the drill,” Holly the Permiscuous Cheerleader said. “You get to do whatever you want to me. So?”

She held her gaze on Jessie, challenging him to let loose. He looked nervous, which would have surprised anyone but her. While Jessie liked to put on a show for his buddies, in private he was very reserved, projecting a quiet intensity she found irresistibly cute. But tonight she was determined to bring him out of his shell. It was his night; he deserved it.

“C’mon,” she encouraged, “what’s something you really wanna do? You know me, I’m up for anything.”

Holly spun in a quick 360, flipping her skirt up just as her back was facing him, tantalizing him with a brief flash of her cotton black panties.

Jessie swallowed hard. “How about anal?” he whispered.

Holly’s heart skipped a beat being a Permiscuous Cheerleader she loved being dirty. She tilted her head forward and cupped her left ear. “Come again? Speak up.”

“How about anal?” he said louder, his cheeks growing flush at the word.

“Yeah, tear that ass up!” someone yelled from outside.

Holly’s asshole quivered at the thought. “You wanna fuck me in the ass?”

Jessie nodded slowly.

“You continue to surprise me Jessie. I guess deep inside, you’re just as dirty as the rest of them.” Holly turned and bent over, caressing her taut cheeks with her hands. “So you want my ass huh?”

“Yes,” Jessie said. He began removing his pads, then his jersey, exposing his moderately toned chest. It was light on body hair, giving him a youthful boyish look Holly found very appealing.

“How badly do you want your cock in my ass?”

She slipped her thumbs underneath her panty line and pulled them down, slowly, maximizing every precious second for his benefit.

“So badly,” Jessie admitted. He stopped to admire the exceptionally sculpted curvatures of her ass before pulling his pants down, revealing his half-hard cock. It flopped out aggressively, calling out to Holly like a force of nature, and she answered back, spreading her cheeks to reveal her tiny pink asshole. Despite the abuse it had taken, it looked as tight as a virgin’s, which she took great pride in.

“It’s all yours baby.” She ran her left index finger over it, in sweet, soft circular motions, taunting him. “Use it how you want.”

“I want you,” Jessie whispered. “But first, I wanna see you.”

His voice was husky, commanding and deep, guided by a lust Holly could see in his eyes, overcoming all his thoughts and senses. In that moment she was his, and it turned her on beyond belief.

So she obeyed, smiling with elation as she removed her cheerleader’s top, then her skirt, all in one unhindered graceful motion, the way she had a hundred times before. She stopped a moment to watch him watching her, following his eye line as he scanned her Permiscuous Cheerleader body, first across her breasts, pert and pale and topped with cherry pink nipples, then down to her stomach, toned and flat, before landing at the pretty pussy that sat between her legs, shaved and ready for whatever her team wanted that night.

At that moment though there was only Jessie

and with a sudden burst of masculine force that gave Holly chills, he bounded toward her, cock throbbing red and swaying side to side with his movements. Her mouth watered at the sight. She had to taste him first, the urge was too strong, burning in her throat.

“First I have to taste you,” she said. She got down on her knees to meet his manhood at eye level. A bead of precum sat heavy on the tip, glimmering under the fluorescent lights like a precious jewel. She stuck her tongue out and delicately pressed it against his cock hole, just long enough to feel his pulse, then pulled away, bringing a long, thin line of precum with her.

“Oh fuck,” Jessie moaned. His cock shivered, sending more precum bubbling to the surface, so much she feared he might come right then.

“Wow Jessie, look how turned on you are. God, it’s so hot.” She pressed her tongue against his cock hole again and flicked it, up and down, lapping up the copious amounts of precum that had started pulsing out of him. “Mmm, you taste so good.”

“You feel so good,” Jessie responded in his delirium.

Holly relished the sight. The thought that her tongue had so much power, the power to give him so much pleasure, was enough to put her on the edge as well.

Now it’s time to seal the deal.

Holly pressed her fingers against the underside of Jessie’s balls and gently drew the entire length of him into her mouth, as far as she could, until his cock head hit the back of her throat, tickling it in that special way that gave her goosebumps, all the while gliding her tongue across his underside, relishing the feel and taste of his flesh, thick and veiny and salted with sweat. She hummed her satisfaction, sending it surging across his body.

“Holy shit, oh fuck,” Jessie sputtered. He placed his hand against the back of her head and pressed, using just enough force to hold her there, just the way he knew she liked, and she took him, as far and as long as she could, until she couldn’t take anymore, and she was left gagging and gasping for air. Just like a good Permiscuous Cheerleader should.

“How do you do that?” Jessie asked, in awe at the sheer power on display.

“Lots and lots of practice,” Holly said between breaths. She wiped the hand across her dripping mouth. “It’s how you get good at anything. It’s how you got good at football, and it’s how I got good at sucking cock.”

“And you’ve sucked a lot of cock?”

“You already know the answer to that.”

Holly knew what he was really asking. She had seen it a hundred times, from nearly every guy she had been with. It was jealousy, primitive and primal, the kind that men couldn’t help but have for the kind of woman she was. He wanted her for himself, as they all did, and depending on the kind of guy the sentiment came from it was either cute or annoying. In Jessie’s case it was the former. He was a sweet guy, soft but assertive.

“Oh, right,” Jessie said, looking slightly embarrassed.

Holly assured him with a soft smile and placed a gentle kiss on the head of his cock. “Don’t worry baby. Out of all the Howlers, yours is my favorite.”

Jessie’s eyes got wide, and a small smile cracked across his lips. “Really?”

“Mhmm.” She started stroking him, gliding her hand along the slickness of her saliva, up and down his length. “I love your cock Jessie. It’s so perfect; long and thick in all the right ways. Ways that make me feel so good.”

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I hope you enjoyed the first part of my Permiscuous Cheerleader Blog. Part II comes out on Wednesday so make sure you check back in. Can’t wait till then? You can listen to me tell you the steamy story in my own sexy voice on my audio. Loved this blog and want to hear more? Check out my Student Teacher Blog.

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Holly 

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