The Cherry Poppers Ch. 05

"Oh, geez, Caitlin. That was awesome," Jason groaned weakly.

"Wow, you cum a lot," Caitlin chided. "I thought for a second there you were going to drown me."

"Sorry ... ," Jason started to say.

"Just kidding. I loved it," Caitlin added.

"Okay, good," Jason replied.

"What now?" Caitlin asked.

"What? Oh, I ahh ... I'd like to do something for you."

Caitlin's brown eyes search his face. Jason stared at the cute brunette. He really liked her. She had a great personality and cute dimples when she smiled. He believed she liked him too. He at least knew she liked sucking on his dick. They looked at each other for long minutes until Caitlin finally spoke.

"What're you referring to?"

"Well ... we could strip down and I could use my mouth on you like you just did to me. Or," he couldn't resist, "we could get it on."

"Which would you prefer?" Caitlin asked, looking a bit unsure.

"That's up to you," Jason offered.

"What if I said both?" Caitlin asked.

"Really," Jason queried.

"Yes, but ... but I should tell you ... ahhh, you probably won't believe this but ... ahhh, I've never done ... either," Caitlin finally got out.

"Ahh," Jason tried to act surprised and was by the admission of no oral. "Would you like to?"

"Yes, definitely. But to be honest, Jason, I'm a little scared. I don't want to mess things up between ... "

"That's not going to happen," Jason said. "Just let me help you."

Jason started undoing Caitlin's blouse. She watched him with rapt curiosity. Amazingly this blowjob artist had never given herself completely over to a man and she felt anxious but excited at the same time. Jason had her blouse open exposing the lacy bra beneath. Caitlin's breasts were not as large as Claire's or as shapely but they looked to be a full B-cup as Jason pushed her shirt from her shoulders.

Caitlin was leaning low against the backdoor to avoid being seen so she helped him by reaching behind and unfastening her bra. Jason watched the soft tantalizing flesh of her breasts come into view as he helped her take off the bra. He stared at her tits as her nipples were exposed. Caitlin had small brown nipples that were fully erect and still only less than a half inch long. Her nipples were cute in their tininess. Her breasts were decent handfuls and Jason's hands immediately sought them out.

Caitlin looked into Jason eyes as if searching for any sign of rejection but instead found his returning smile. His hands palmed her firm yet soft tits and grazed over the bullet tight nipples.

Jason looked up from her tits into her eyes and said one word, "Beautiful."

Caitlin seemed to exhale like she had been holding her breath and said, "Really?"

"Gorgeous," Jason reiterated but differently.

"You're not just ..." Caitlin's words and breath caught in her throat when Jason descended to her right nipple and sucked it into his warm, wet mouth quickly.

"Oh, god," was all Caitlin could mutter then.

Jason feasted on each breast in turn and played with them for a good ten minutes. They were soaked with his saliva and slightly flushed from his constant handling when he undid her jeans. Caitlin helped him and soon they and her panties join the rest of her clothes on the floor of the car. She was naked before a man for the first time.

Jason pulled Caitlin to him making her sit lower in the car. As he did he got a good look at her pussy in the dim light from the few parking lot floods. She was not shaved like the other women had been this weekend. Maybe she didn't believe in it or maybe she just hadn't been prepared for them to go this far. Either way Jason found it refreshing to stare at her natural pussy.

Caitlin had a tuft of brown hair atop her cunt and more sparse hairs running down the sides of her labia. Her mounds were puffy and Jason could make out moistness in the slit of her pussy, evident as the light fell on her. He positioned himself between her open legs and glanced up to grin at the nervous looking Caitlin.

"I know you're going to like this," he said to ease her nervousness.

Caitlin watched intently as Jason settled over her sex and looked at it. His fingers parted the outer lips and opened her to his gaze. Despite her nervousness, she was wet inside and invitingly pink. Jason kissed the inside of her thighs and moved all around her pussy. He teased her a bit before actually moving to her inner core. Caitlin watched excitedly as he ran his tongue along her gash.

"Oh, geez," Caitlin purred as she felt his tongue touch her.

Jason kissed Caitlin's inner labia and then probed his tongue into her pussy. He sought out the entrance to her virgin cunt and wiggled his tongue around the opening. Caitlin moaned loudly as he pushed his tongue into her and tasted her growing wetness. He spent a good bit of time working on her cunt hole before moving higher.

Next Jason pulled back on her clit hood with his fingers and exposed her little knob. He teased all round it driving Caitlin crazy. Her fingers were now in his hair and she moaned as his tongue caressed the sensitive tissues around her clit. After teasing her briefly he swiped his tongue several times across her clit. Caitlin stiffened under him and grunted loudly. Jason could feel her increasing lubrication with his fingers and tongue. He tasted her nectar as it seeped from deep inside.

When Jason finally decided to suck her clit into his mouth, he had Caitlin built up to a frenzy. She grunted and started to buck up off the car seat to meet his probing tongue and sucking mouth. Jason could tell she was close. He moved two fingers to her cunt hole and teased around the opening but refrained from trying to penetrate her. The added stimulation along with his attack on her clit was too much for Caitlin.

"Oh, fuck! Jason ... oh, god, I'm going to cum," Caitlin screamed.

Jason hoped no one was near the car for surely they would have heard her. He tried to stay in place sucking her clit and finger teasing her as she squirmed and trembled. Her orgasm washed over her like nothing she had ever felt before. The waves of blissful pleasure emanating from her cunt spread like a raging fire throughout her body. Her own hands pulled and mauled her nipples as she shuddered to conclusion of her first oral induced climax.

Caitlin's head was back and her eyes were closed as she panted and fought to recover from the wonderful orgasm. She felt Jason's hands leave her but was not aware of much else. It wasn't until she felt something new touching her cunt that she opened her eyes. Jason was positioned above her with his cock poised at her cavity entrance.

"You ready for this?" Jason asked, his lust-dominated voice showing his need too.

Caitlin would have liked a little more time to recuperate but could see that Jason was ready. 'Oh, god, here it comes,' she realized. 'He's going to fuck me now.'

"Caitlin, you ready or not so sure now," Jason pressed, as he rubbed his cockhead along her slick pussy.

"You're going to go slow, right?" Caitlin pleaded.

"Don't worry," Jason claimed.

She did worry though as she felt his cockhead nudge up against her opening. Jason pressed in until he was starting to enter. It didn't take long for him to feel the obstruction blocking the entrance to her pussy. He aligned himself for the thrust which was becoming near commonplace for him this weekend.

"Ready?" Jason asked, as he leaned in to kiss Caitlin.

She kissed him back and replied weakly, "I guess so."

Jason immediately thrust hard. He didn't wait for her to prepare for the pain. He tried to catch her by surprise in order to get it over with before she could concentrate on worrying. He was becoming quite good at deflowering women and knowing just how hard to make the initial thrust. His cock pierced right through Caitlin's hymen like a harpoon. He then held still giving her time to recover.

"Ouch ...!" Caitlin cried. "Oh, shit. Ungh."

"You okay?" Jason questioned.

"Shit! That hurt!

"Sorry but you knew it would at first."

"Yeah ... but it still hurts."

Jason waited for her to relax. He could feel some of the tension leaving her as she settled back down as the pain weakened. He moved his cock just slightly allowing Caitlin to get used to it. She moaned a little but didn't beg him to stop.

Jason thrust a little deeper which again made Caitlin moan loudly. She was incredibly tight and despite her moistness, it was slow going as her cunt reluctantly opened to accept the intruder.

"Oh, geez," Caitlin groaned as his cock penetrated further. "You feel like a giant bat inside me."

"It will feel better soon," Jason tried to reassure.

"Shit, it feels like you're stabbing a knife up into my belly," Caitlin complained.

"Should I stop?" Jason asked.

"No, keep going," Caitlin allowed.

Jason worked slowly but methodically and gave Caitlin all the time she needed to adjust to the pain and new sensations. Finally he started to develop a rhythm and in short order Caitlin's moans started to sound more like pleasure than pain. Jason was thrusting deep into Caitlin with slow long strokes. Her hands clung to his sides trying to control his depth and speed. After a while though her hands were actually pulling him to her, so he sped up.

"Oh, geez," Caitlin hissed. "That feels incredible now. Your cock is so huge inside me. I can't believe how good it is starting to feel."

"It's going to get even better, babe," Jason proclaimed.

"Oh, god! I think I'll keep this thing inside me forever," Caitlin shouted.

Jason, encouraged by Caitlin, was now fucking her at a strong steady pace. His balls were beginning to churn from the incredible tightness of her cunt. He wanted her to get off too and hoped he could hold out. Fortunately Caitlin was groaning loudly beneath him and he felt sure she was nearing her climax also.

"Ahh," Caitlin moaned. "So good. That feels so good, Jason."

"It's going to feel better in a moment," Jason claimed with a gasp.

He started fucking her harder, faster, and deeper. Caitlin groaned at the intense feelings running through her body. Her orgasm was coming on like a freight train. Exquisite licks of pleasure were coursing through her body, starting at her pussy, and manifesting themselves in her brain and nipples. Her fingers were aggressively tweaking them in an unending effort to answer the delicious itch there. Finally everything crested at once.

"Oh, fuck me!" Caitlin howled. "Oh, shit ... Ahhh ... "

"Here's my cum," Jason shouted, realizing all at once they had given no thought to her unprotected womb.

"Ahhh ... " was all Caitlin replied as her orgasm took over.

Jason's cock pumped load after load of cum deep inside Caitlin. She could feel his hot spunk mixing with her own juices and the combination only heightened her climax. Her body went stiff and her cunt clamped down on its own on Jason's cock, milking him of every drop of cum he had left.

"God," Caitlin finally muttered after her intense orgasm was over.

"Whew," Jason added too. "That was great."

"It sure was," Caitlin agreed, letting the fact he had unloaded in her not matter for now.

They rested together until both were breathing normal. They then dressed and Jason walked her to the dorm. She offered for him to come inside but it was getting late and he had plenty to do, so he declined. They did agree to try to get together again the following weekend. Caitlin kissed Jason goodbye.

"Thanks," she said. "That was great."

"You're welcome and thank you too," Jason responded.

They kissed one last time and then Jason left. He wasn't sure what happened to Chad and if he planned to stay the night or not. It was only a five minute walk across campus to the frat so he didn't worry about waiting. Back in his room he tried to study but thoughts of the incredibly wild weekend kept entering his head. He wondered if he had indeed set a record for the most conquests in a weekend.

The next day after classes Jason went to work as normal. This time, however, he was on a mission to see if Kim was listed in Doctor Jenny's records. He was delighted to find that she was. She had gone early on as a freshman to see the doctor. There next to her birthday date in the normal spot was the asterisk. Mark must have entered her card in the records as Jason hadn't been working at the infirmary until second semester the previous year. So he now had the evidence he needed to prove four virgins undone in one weekend. Four cherrys popped over three days. Was it a record though? 'Had to be,' Jason thought. 'No one else could possibly have done more."

After work Jason raced back to the frat. He called Mark on his cell as he sprawled across his bed. Mark was working but about to head home too.

"Hey, Little Brother. What's up?" Mark answered the phone.

"Hey, Mark. How's it going, Big?"

"Stay in school. Work is definitely not as much fun," Mark claimed.

"Oh, yeah? I guess I can see that, especially after this weekend," Jason replied.

"Why? What was so special about this past weekend?

"What's the record for most cherries in a weekend, three days?" Jason asked.

"Not sure I know, dude," Mark said. "Why? You score a couple?"

"Better than that!" Jason confirmed.

"Yeah? Well, I did two on a weekend so you're going to have to beat that. And I think if you look back in the log several brothers, you'll find one dude that did three.

"How about four?" Jason boasted with pride.

"What? No fuckin' way," Mark said, but kept his voice low for the office.

"Yes, way, dude!" Jason exclaimed. "Four, count em, four from good old Doctor Jenny's charts."

"Wow! You're the man. I knew you had it in you, that's why I picked ya," Mark stated.

"Well, that gives me five total. When did you hit five?"

"Not till at least Christmas as I recall so you are ahead of my pace. Good going, Little."

"I might be on a record pace then," Jason allowed.

"Might at that," Mark said but chuckled. "Listen to you, the guy that wasn't sure this was for him. Now you're trying to break the record. Well, good luck."

"Thanks."

"Don't forget to log your entries. You might forget details if you don't. You might also call Mr. Caulfield. He is a generous guy and might be impressed with your weekend performance."

"You think so?"

"Never know. He can surely appreciate what an unbelievable accomplishment four is in one weekend."

"Í guess so."

"See ya, Little. I got to finish up here. Call me anytime, especially with this kind of news. You just made my week," Mark professed.

"Thanks, Big. Talk to you soon," Jason responded.