The Cherry Poppers Ch. 19

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Sorry to all it took me this long to write another chapter. I hope to keep this story going to conclusion now. Thanks to all of you that have written to encourage me to finish this.

Jason’s mind raced about what Beth had said the night before. So much so, that he couldn’t study. Her statement, she loved him, and his similar response back, had him wondering, ‘Did she mean it the way he thought? Should he even continue to tutor Sheila in Spanish?’ He tried to tell himself it was his duty to help her and Beth would understand. But he wasn’t being paid to tutor Sheila, nor was he doing it purely out of a sense of duty to help a fellow student. No, he hoped to fuck her and capture her cherry. That he couldn’t deny, even to himself.

His confused and troubled mind worked overtime until he fell asleep on his bed still trying to study. He woke when Chad came into the room from a work-out to shower and change. Jason jumped up when he saw the time, knocking a book off the bed on the floor. He needed to get ready to see Sheila. ‘It wouldn’t be polite to cancel at the last minute,’ he told himself.

After showering and getting ready, Jason had a few minutes, so he again tried to study. This time, not only did he fight the thoughts of Beth, but his stomach was growling. He had grabbed a quick lunch in the frat kitchen earlier but he was hungry again and the chef was off on Sunday nights, which caused the brothers to fend for themselves.

Jason thought he would talk to Sheila about getting something to eat first. He drove over to her sorority, in case she agreed, so his car would be there when they finished studying later. He walked in the front door and made his way to her room. He passed several girls that smiled sweetly at him and said hello. He admonished himself for wondering if any of them were virgins. ‘This contest is changing my attitude towards women and not in a healthy way,’ he realized as he knocked on Sheila’s door.

Sheila answered almost immediately and invited him in. She looked great Jason observed as he took a seat at her desk opposite her bed. Her blue shirt fit tight and Jason thought he could see the outline of her nipples. Her jean skirt was very short and rode way up her dark legs as she sat on the bed. ‘If she parts her legs I’ll surely see her panties,’ Jason surmised. She began talking to him about being glad to see him and thanking him for tutoring her today as she shifted her long sleek ebony legs. Jason was trying not to stare and to stay focused on her face, but his eyes wanted to watch her uncross and cross her legs. He fought the urge. He didn’t realize that Sheila was trying to get him to notice her naughty lack of underwear.

“Hey, you want to get a bite to eat?” Jason asked. “I’m starved. I don’t think I can concentrate on Spanish right now until I eat.”

“Okay,” Sheila answered, not seeming too upset to be putting off studying.

Jason drove them to the diner. The conversation along the way was mostly questions Sheila asked him about the swim team. His practices were about to start as the season approached. He would be even busier soon than he was already. He didn’t relish that.

She told him about her track practices. She had a few months before spring practice started in earnest but she tried to stay in shape by running a lot. A sprinter and long jumper were better off if they kept their muscles fairly toned even in the off season. He commented on that.

“Your legs look pretty toned to me,” Jason complimented.

“Thanks. I didn’t think you were noticing,” Sheila quipped.

“I was trying not to stare,” Jason stated in defense.

“I was sort of hoping you would,” Sheila claimed affably.

“Might just from now on,” he replied.


They ordered two different sandwiches and split them, each having a half from the other. Sheila asked him questions on Spanish while they ate. She seemed intent on getting the tutoring part of the evening out of the way. They had left the books back in her room but he still helped her sound out some words and on several points of grammar.

After eating, Jason paid the bill and they hurried back to her room. Sheila’s roommate wasn’t back yet so they got right into studying. He helped her through a dialogue and they covered a mock quiz from the end of the chapter. After about an hour she felt good about her progress.

“I’m getting it. I think I can handle it from here,” Sheila claimed.

“Yeah, you’re getting much better with pronunciation and grammar,” Jason praised.

“Thanks to your help.”

“Just a Good student,” Jason acknowledged, closing one book and handing it back to Sheila.

“You don’t have to leave already do you?” Sheila asked.


“Well…,” Sheila stammered, “I was kinda hoping we’d finish like we did last time.”

“How’s that,” Jason played coy.

“You know… in the car…at the airport.”

“You mean in the backseat,” Jason said jokingly.

“Well, we don’t need the backseat anymore,” Sheila stated. “We can stay right here and use the bed.”

“Oh, yeah,” Jason mused.

“What’s this acting uninterested,” Sheila scolded. “You need encouragement?”

Jason Side escort watched as she brazenly spread her legs. The short skirt rode high up on her thighs letting the light from the desk behind him illuminate her legs. He looked this time and was shocked to not see any panties at all. Instead her dark shaved pussy greeted his hungry eyes immediately. Jason’s expression must have given away his thoughts based on Sheila’s next comment.

“Surprised, big boy?” Sheila queried merrily.

“I little,” Jason said, recovering somewhat. “It was pretty daring to walk around like that, girl.”

“Actually, I tried to flash you the moment you came into my room,” Sheila admitted. “I’ve been hot for you all day thinking about you coming over. I wanted you to fuck me right then and there, Jason.”


“Doesn’t matter,” Sheila said about her virginity. “I want you to be my first.”

“You sure about this?” Jason said halfheartedly, but scolded himself at the same time for being such a gentleman.

“Definitely… I’m ready… as long as it’s with you.”


“You just going to sit there or are you going to come over here and get this?” Sheila asked leaning back on her elbows on the bed which exposed more of her beautiful mocha skinned pussy to his view.

Jason wasn’t sure what expression his face showed but if it looked anything like the desperation in his eyes had for that pussy, it was probably evident what he really wanted. He stood and in doing so suddenly noticed his cock was already responding for him. He took the two steps toward the bed as Sheila sat back up to greet him.

“Let me help you,” Sheila offered, her eyes now focused below his belt at the rising bulge.

Jason stood before her at the side of the bed and watched her hands intently as they opened first his belt, the button on his jeans, and then undid his zipper. He couldn’t believe how this previously somewhat shy girl was suddenly so bold.

“What about your roommate?” Jason questioned.

“She won’t be back for hours,” Sheila pronounced.

His pants dropped to his ankles and Sheila wasted no time making his boxers join them. His semi-erect cock bounced freely and continued to rise and point towards her face.

“Shit… I couldn’t wait to see him again in the light,” Sheila stated. “He’s beautiful.”

“He’s happy to see you again too, babe.”

“I’m going to make him even happier,” Sheila claimed taking Jason’s cock softly into her hands. “He’s so big and warm.”

Sheila’s hands caressed Jason’s firming member and she moved it around as if inspecting every aspect of it. Jason watched hungrily as her hands brought him to full hardness. His legs trembled a bit when her pink tongue flicked from her mouth and licked tenderly at the tip of his head.

“Oh, god!” Jason bellowed.

“You like that, big boy?” Sheila said, looking up into his eyes as she continued to tongue his sensitive cockhead.


“Good… there’s more,” Sheila said and immediately engulfed the whole head into her hot, wet mouth.

“Oh, fuck,” Jason growled.

“Later,” Sheila mumbled with his cock still in her open mouth.

“He promises to make it wonderful for you,” Jason offered.

“I’m hoping so,” Sheila agreed.

She returned to sucking on the head and stroking the shaft with her hands. One hand reached down to cradle his hanging testicles and rolled them back and forth. Her inexperience still showed a little, but she more than made up for it with her anxious attempts to please him. As she tried different things, she glanced occasionally to his face looking for reactions. He aided her by moaning praise with each especially pleasureful lick and suck. He reached out and caressed the side of her face as she looked intently into his eyes. Jason pushed forward a little encouraging her to take more. Sheila tried, took some, but gagged a little when the big head pressed to the back of her mouth.

“I can’t take too much,” she sputtered as she cleared her throat.

“Try to yawn when it’s in the back of your mouth and let it ease down your throat,” Jason coached.


Sheila tried that and actually got a little more before still gagging. She leaned back laughing.

“What’s so funny?”

“You’re coaching me at everything these days,” Sheila said laughing.

“Yeah, I guess I am,” Jason agreed amusedly. “Lean backwards.”

Jason peeled off his pants and boxers and squatted on the floor between Sheila’s splayed legs. He stared at her beautiful pussy with just the slightest hint of pink visible between the folds of her dark labia. ‘God, it’s gorgeous,’ Jason thought.

He looked into her now pleading eyes as he pushed her legs further apart. He glanced down at her feminine charms and could see more of the pink inner core in this position.

“You shaved completely?” Jason noted.

“I thought you’d like it like that,” Sheila proclaimed. “The other girls think their guys prefer a clean…,”

“It’s beautiful,” Jason avowed.

“You think so?”

“Completely,” he declared.

Jason parted her pussy with his Side escort bayan fingers and watched, mesmerized, as the rich wet pinkness came into view framed by the mocha lips of her sex. He felt drawn to it like a moth to the flame. His mouth suddenly felt wet and hungry.

Jason kissed along the lips of Sheila’s splayed pussy. He vowed to himself to bring her to two orgasms before attempting to take her offered cherry. She would be number thirteen but he tried not to think of that as he teased her inviting cunt.

“Oh, god,” Sheila moaned, turned on by his tender kisses.

Sheila had thought of this day since high school. Like all girls, she thought about the day she would lose her virginity and her plan had been to lose it to a white guy. Here she was with a white guy she cared a great deal for, kissing her pussy, and hopefully soon going to finally make her a woman. She was incredibly nervous, especially with his huge dick, but she was ready too.

Jason licked along Sheila’s inner lips before move lower and to her center. He focused his tongue movements on the edges of her virginal vagina. He could see her intact hymen. His tongue traced around it making Sheila growl with need. Her pussy was wet and getting wetter by the second. He lapped at her sweet juices and teased all around before moving to her ultra-sensitive sex organ. Even when he shifted to focus on her clit, he played around it for a good long while, driving Sheila insane with need. Her hands grabbed handfuls of his hair and pressed his mouth to her stiff little pink pearl.

“Oh, good god…please, Jason! Please lick me there!” Sheila howled.

Jason smiled to himself, but complied with her wishes and sucked the urgent bud into his mouth. His tongue immediately played over the sensitive tip, driving her right up her climactic ladder. Her legs were taut as bowstrings and squeezed his head mercilessly as he fought hard to maintain his control over her rising orgasm. Her nectar coated his face as he attacked her clit. Sheila bucked off the bed against his face. She was there. Her super sensitive clit throbbed like a tuning fork, and sent shockwaves out from her core.

“Shit! Oh, fuck…suck it, please…aah…,”

Jason tried to overpower her strong legs but it was no use. Her legs were far stronger than his arms and he gave in to the near crushing pressure against his ears as she rode his mouth like a bucking bronco.


Jason tried to breathe the best he could as he continued to lick her hard pebble. Sheila bucked against his face and drenched him with her girl cum. Jason lapped at the essence of her. She tasted great and he lapped for more even as he fought for breath.

Sheila felt like her head was going to explode from the blissful pleasure radiating from her sex to every pore of her body. Her body held still, in a lock-tight position, as the waves of incredible ecstasy washed over her like wonderful warming electrical currents. It seemed to last a good long time but yet ended way too soon. Finally, she slumped to the bed giving Jason a much needed chance to breathe.

Jason recovered his breathing as he watched Sheila’s heaving chest settle too. He then realized he wanted to see those nice tits with their chocolate nipples. He undid her shirt as she just lay there enjoying the afterglow of her incredible orgasm. She seemed oblivious to being stripped. Jason opened the shirt to indeed find she was braless. Her cute full breasts were like upside-down cupcakes in size. The distended nipples were pushing out a good half inch, inviting his mouth which quickly engulfed one.

“Oh, nice,” Sheila moaned as she felt Jason suck on her excited nipple and tease the other.

Jason played with her tits for a good long while, sucking each nipple a couple times before kissing back down her belly. Sheila tried to stop him saying she couldn’t take anymore but he didn’t listen. Soon he was driving her nuts with his mouth again.

“Oh, fuck,” she groaned as he sucked deliciously on her labia minora.

Jason worked hard to get her off again and was rewarded fairly quickly with another good burst of her nectar as she came rather fast this time. It was not as intense as the first but you couldn’t tell that from the flood of cum on his face. He continued to eat her until she pushed away his head and tried to roll to her side. He held her though and climbed on the bed between her legs. He shifted both their bodies the long way on the bed. He moved over her, his cock like a raging rod of steel, eager to penetrate the core of this black beauty.

Sheila realized what was about to happen and looked up at him with imploring eyes. A sudden nervousness was evident on her sweaty face.

“Be gen- “

“Shh,” Jason said. “I will. Just relax, babe.”

“Jason, I’m not on…,”

“I’ll pull out.”

She watched intently as he aligned his cockhead with the soaked center of her being. He felt the entrance to her pussy and positioned himself to break her hymen. He looked up into Sheila’s brown concerned eyes. He leaned down and kissed her. They kissed passionately and his intent was to distract her. He succeeded Escort side somewhat until he shoved forward once his cock was in line with his goal. The first thrust wasn’t hard enough and caused Sheila to wince and moan in pain. Jason rapidly followed with another to get it over with and sunder her maidenhead. He succeeded this time in breaking right through.

“Ahh … Oh, fuck!” Sheila growled. “Ouch! That fuckin’ hurt!”

Jason held still, “Just relax, babe.”

“Easy for you to say,” Sheila claimed with a grimace. “You’re not the one getting stabbed by a big blunt pole.”

Jason waited with her until she relaxed a bit. Her death-grip on his sides relented a little. He eased forward slightly, making her stiffen again, as a little more cock spread her further open. He waited again before repeating the pattern. It took a few more moments before he was over half way buried inside her body. He liked the contrast of her dark skin next to his as his white dick sank further into her black hole.

“Oh, geez,” Sheila groaned.

“How’s it feel now, beautiful?” Jason asked.

“Like a huge pole inside me,” she responded.

“Just give it a minute.”

“You think that’s going to help,” Sheila accused sarcastically.

She waited with him though, and soon even she had to agree the pain was being replaced by a dull ache. It returned a little when Jason moved, but lesser each time. She could even feel him pushing deeper. She couldn’t believe he could fit that monster cock so far inside her.

Jason waited till she was ready before withdrawing nearly to the entrance and pushing back in slowly. Her wet pussy was opening and starting to stretch to accommodate the big intruder. She was still incredibly tight, but her pussy began to react favorably to the feeling.

“Oh, god,” Sheila gasped.

“Getting good?”

“Much better.”

“You’re over the worst part now. You’re going to love the rest,” Jason declared.

He moved with the practiced ability of a thirteen time cherry taker. He pulled out slow and eased back in at near imperceptible speed. He did this long enough until Sheila actually started to urge him on with her hands. She also learned the rhythm and proved adept at keeping up with him.

Jason gradually increased the pace as he learned what Sheila could take. Soon, it was her urging him on faster. He readily complied and even pushed deeper into her, making her groan pleasurably with the new fuller sensation.

“Oh, god, Jason.”

“Like, it, babe?”

“You know it. You were right. It feels good now. The pain is mostly gone.”

“Ready for a little more?” Jason asked pushing even deeper and hitting her cervix.

“Oh, fuck! You feel a mile in me. It feels like you hit bottom too.”

“Not really, but we’ll hold it here for now.”

Jason fucked Sheila with long smooth strokes. She soon matched him by fucking back into each thrust. Her low moans turned to groans of pleasure and then gasps of bliss. In no time Jason was pumping her full of thick cock and she loved it. Her moist tight tunnel gripped him in a velvety sweet embrace. Her strong legs added to the force of her return thrusts. She would be a wild fuck once she got used to it, he could tell.

“Oh, what a sweet pussy,” Jason praised.

“You think so?”

“Beautiful, like you.”

“Thanks, your dick feels good now too.”

Jason wasn’t sure how much more he could take. Sheila’s pussy was so incredibly tight. He pulled back and then thrust his steely cock back into her. Sheila groaned beneath him as he picked up speed and fucked her good. She seemed to be over any feelings of pain. Instead her strong sprinter’s legs encircled his hips and pulled him to her on each plunge like she couldn’t get enough. Jason’s cock found Sheila’s cervix repeatedly but unlike other girls, she didn’t seem to mind. She only groaned with approval.

The blissful pleasure from fucking soon had Sheila enthralled. She urged Jason to go faster with her hands, legs, and gasps of delight. Her mind became clouded with the intense pleasure emanating from her pussy as Jason probed her depths. Each inward thrust gave her wonderfully intense ecstasy, while each withdrawal had her feeling empty of cock and wanting more quickly.

Both rode the powerful waves of happiness to the ultimate high. Jason was fucking Sheila with abandon now. Sheila was taking it and urging him for more. She couldn’t get enough of the feeling of his big cock inside her. Fucking was even more magnificent than she had imagined. The words of her friends that had been here before her couldn’t come close to explaining the feelings she felt now. A chorus of delight rang out in her ears as she barely heard her own words of bliss.

“Oh, Jason… Oh, baby… fuck me good. Oh, god!”

Jason’s mind cleared for a brief moment and thankfully so. He somehow realized, through his own pleasure clouded brain, that he couldn’t cum inside her. He so wanted to complete the act properly, and fill her no longer virgin hole with a hot bath of his sperm, but that was not to be this time. Incredibly, thoughts of Beth rushed into his head at that moment. He wanted to feel guilty for what he was doing but instead those same thoughts made him growl with intense desire. He pounded into Sheila a few more times pushing her over the edge. He could feel every part of her tighten suddenly and he couldn’t hold back any longer either.

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