The Cherry Poppers Ch. 05

Story Info
Does Jason pop a record number for a weekend?
6.2k words
4.7
133.8k
18

Part 5 of the 29 part series

Updated 11/01/2022
Created 10/24/2007
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
BlewWater69
BlewWater69
2,580 Followers

Jason glanced at the clock and noticed that it was ten. He needed to get up soon but also felt like more sleep. He dozed a bit until he felt a hand touch his face. He opened his eyes to see a naked Kim leaning over him.

"Thanks, Jason," Kim whispered.

"You're welcome," he replied softly as not to wake Claire. "I'm glad you enjoyed it."

"Oh, I did. We'll have to do this again if you're willing," Kim responded.

Jason almost jumped for joy but held back, willing himself. If they wanted to do it again, wild horses couldn't keep him away. Oh, yes, he was willing alright. "Anytime."

"Good. Would you care for a shower?" Kim asked.

"What about Claire?"

"She's out like a light. She could sleep through a hurricane," Kim stated.

"Okay," Jason agreed, since he needed to get going anyway. It was now 10:30.

Kim backed off the bed and Jason cautiously followed. Kim was right, Claire never moved. Jason grabbed some shower towels along with his bath kit and Kim wrapped herself in the same blanket again. When they exited the room for the showers across the hall several brothers saw them and smiled, calling hello.

Jason got the water going as Kim hung the towels. They managed to make it behind a curtain and into a stall before anyone else entered. Jason loved Claire's big tits but there was something incredibly sexy about Kim. It wasn't like one thing stood out but the whole package together was like near perfection. He soaped her back for her eventually letting his hands move around front and cup her breasts. They were perfect handfuls for him.

"You have nice big hands," Kim stated.

"Good for swimming," Jason responded.

"Good for a lot of things," Kim replied, turning to kiss him.

Jason eagerly kissed her back but wondered, 'What am I doing here? I'm supposed to be with Claire, who's in my bed now, and here I am with Kim.'

They soaped each other and washed each other's hair. Kim's long hair was far tougher to do than his. He loved her brunette hair and the way it shone brightly when wet and clean. Jason shaved and she watched but with both hands on his now stiff cock. When he finished rinsing he was ready to get out but Kim had other ideas.

Without saying a word, she squatted down and kissed his bulging cockhead. Her hands were already teasing the flesh and massaging his balls. Kim licked the head a few times before looking up.

"Can I suck it for a little while? I've wanted to since I first saw it last night," she asked.

Looking down, Jason realized there was no way or no one in their right mind that would refuse her, "Sure you can."

Kim smiled broadly and then surprised him by taking the complete head and more inside her mouth in one swift move. "Ungh," he moaned as she proceeded to wash her tongue over and around his blood engorged cockhead. He could feel her tongue ring rolling across his flesh.

"Oh, my god, Kim. That feels great," Jason praised.

Kim's tongue teased back and forth under the head of his cock making him groan loudly as the silver stud ball rubbed deliciously across his sensitive nerve endings. She kept that up for a while until his legs started to shake, then she backed off.

"Like that?" Kim said with a knowing smile.

"God, that was fuckin' great," Jason growled.

He watched as Kim teased him for a while longer. He was content to cum in her mouth if that was what she wanted but again was surprised when she stopped and stood up. She kissed him. 'Is she stopping?' he wondered.

"What to fuck my ass?" Kim said, breaking the kiss.

"Huh ... I guess so," Jason concluded.

"I'd let you fuck my pussy again but I'm afraid I'm too sore. Your cock is big but I think I can handle it," Kim proclaimed.

"You sure you can handle it," Jason queried.

"It would help if we had some lube but saliva will have to do," Kim said, spitting on the head of his cock and rubbing it in.

"You're in luck," Jason said, producing a little tube of Vaseline from his kit.

Kim gave him a funny questioning look but he just said, "Don't ask." She got it and chuckled.

Together they lathered her asshole and his dick. Kim leaned against the wall and Jason crouched to align his cock with her small little rear passage. Entry was even tighter than her cunt had been. Eventually the head popped past her sphincter muscle and lodged in her ass. Kim stiffened and grunted.

"Oh, fuck," she said. "On second thought, my cunt couldn't hurt this much."

"You want me to ... "

"No, just give me a minute," Kim professed.

Jason did then started pushing in slowly. It took a while but eventually he was deep in her bowel. She was unbelievably tight back there.

"God, you're fuckin' huge," Kim lamented.

"Yeah," Jason replied, smiling but she couldn't see.

"Go slowly please."

"Okay."

He did, fucking her in slow short strokes. After a time he was able to build to a good rhythm. She was smaller than him and he had to keep his legs bent to fuck her ass. Kim braced herself against the wall and Jason palmed her nice breasts as he fucked her ass. When he started to feel that old familiar roiling in his balls, he picked up speed again and fingered her clit with one hand.

"Oh, fuck me," Kim pleaded. "Your dick is so huge in my poor little ass."

Jason fucked her harder. He was getting ready to blow and fingered Kim's clit desperately in an attempt to get her there too. It was working and pretty much at the right time.

"Ungh," Kim growled leaning back into him. "That feels so good. Fuck my ass, Jason. Cum in my ass."

Jason sped up one last time but was rushing headlong to climaxing. He thrust into her a half dozen more times and then howled. He pushed one last time deep inside Kim and held still as his orgasm crested. His cum blasted into her ass and coated the abused walls of her tight bowel. Kim grunted and, leaning back into Jason, came too. His fingers were still teasing her sensitive clit and right nipple.

They rode out their respective climaxes together. If not for the shower they surely would have been sweating from the effort of the ass fucking. Kim slid off his beast of a cock and reached back to feel her gaping asshole.

"Wow, you stretched my poor little butt like a crater," Kim said jokingly.

"You okay?" Jason asked.

"Yeah, sure. I will be. Thanks, Jason."

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

They cleaned each other off and went back to the room. Eventually they got Claire awake and up too. It was near noon so they grabbed a quick lunch together before the girls headed out. Jason got jealous eyes from most of the other brothers as they ate. The girls left but not before they discussed the next weekend and made tentative plans for Saturday again. Kim was fine with going out with Kyle again, who they ran into just before leaving and filled him in on the plans for next weekend.

Jason had to hurry. He had studying to do and then to get ready to meet Caitlin for golf. He called her to set the plans. He got Nina, her roommate first, and Nina went to get Caitlin. Soon Caitlin was on the phone.

"Hi, Jason," Caitlin said.

Hi, Caitlin. Can you be ready by two?" Jason asked.

"Yes, but I have a question. You think Chad would like to go too with Nina?"

"Ah, I don't know. He has a paper due tomorrow but he might be able to get away for a while. I could ask. It would be fun to double date. Is that what you two are thinking?"

"Yes, exactly. Nina had fun at the frat party and she would like to go play miniature golf as well," Caitlin explained.

"Well, I'll ask Chad but it's fine with me if she comes with us whether he does or not," Jason offered.

"Oh, that's nice of you but I think she is hoping Chad can make it."

"Hold on," Jason said.

Chad was at his desk writing as Jason put the phone on mute. "Did you hear that?" Jason asked.

"Sort of," Chad said. "Nina wants to go too and she wants to know if I want to double with you guys?"

"Exactly. Can you?"

"I'm almost done with this paper. Are you going to be back early?"

"I hope to be. I've been burning it at both ends and need to study and rest some before Monday is here," Jason claimed.

"I'll say you have. Well, as long as we are back relatively early I can go," Chad stated.

"Good. You'll make Nina happy and Caitlin also."

Jason got back on the phone and told Caitlin. The girls were happy and the plans were set. At 1:45 Chad and Jason jumped in his car and headed for the girls dorm. Both were ready and by 2:05 they were on the road out of town to the one miniature golf course they knew to be open this late in the season.

It was a fun miniature golf course with some interesting yet tough holes. Jason won the competitive game in which the girls were surprisingly very good. In fact, Caitlin beat Chad but he beat Nina by just one stroke. The girls work at a miniature golf course must have helped their game. They had a great time with many laughs. Nina and Chad were good together again which gave Caitlin and Jason a few minutes alone at various times.

Caitlin shocked Jason about half way through the game. She snuck up to him when they were alone and said, "I've been thinking about something big since the last time we were together."

"You have?" Jason questioned but with glee in his voice.

"Yes, I can't seem to get him out of my dreams - wet dreams, I think you call them," Caitlin said jokingly.

"Well, I know he was happy to make your acquaintance too," Jason agreed merrily.

"Would he like a repeat performance?" Caitlin asked, smiling.

"I know we both would like that," Jason replied.

"Good," Caitlin said.

"What about Nina and Chad?" Jason queried.

"I think Nina likes him. That should take care of itself," Caitlin hinted knowingly.

"I see," Jason said, then, "Hey," as Caitlin slapped his butt playfully.

After golf they went to get something to eat at the diner. It was just starting to get dark as they left. Caitlin suggested they go watch the planes again at the Mercer County Airport. No one seemed to care what they did as long as they didn't just head back to the college.

Jason pulled the Camry to a stop in practically the same spot as before. Two other cars were there too but fifty feet away. Caitlin was up front with Jason and Chad in the back with Nina. Jason looked back and Nina and Chad were already in one corner of the backseat kissing. When he turned back to Caitlin, she was smiling and whispered to him.

"I told you it would take care of itself."

"So you did," Jason chuckled lightly.

Caitlin was already up on her knees leaning across the console. It was dark now but still plenty of light from the airport runway floods. The other cars probably couldn't see what was going on as they couldn't tell in those cars either. But inside the car, it was easy to see. She kissed Jason and tongues were immediately doing battle. Jason liked this woman's forthright nature about sex. Caitlin seemed to know what she wanted and to go for it.

It wasn't long before her hand was in Jason's lap. He was already semi-hard from the hot kissing session and grew more so as Caitlin gently squeezed his clothed cock. Jason would have liked to be alone with Caitlin. He wasn't much for group sex, at least with other guys present. The night before with Claire and Kim had been his first true threesome, but that was beautiful with the two women. In the car, he also wished they had more room. He knew Caitlin was a virgin and he was already on a roll, having popped three cherries already this weekend. Why not try for a fourth? He wondered what the record was for the contest in a weekend. 'Four had to be up there,' he thought.

Caitlin had been unbuttoning his shirt and kissing his neck and chest. She returned to his lips with a smile. They kissed again for many long hot minutes. His cock was now becoming uncomfortably tight in his jeans. Caitlin felt him shift and realized his discomfort.

"You need to let him out," Caitlin said jokingly.

"It's a bit cramped in there," Jason chided.

"I bet based on how excited he feels," Caitlin whispered giggling, returning her hand to his groin. "Shall I release the beast?"

Jason glanced back to see if Chad or Nina were looking but they were slumped down on the seat in the dark. Caitlin followed his eyes and from her position could see better. She looked for a second then turned back to him.

"They are quite busy," Caitlin informed quietly. "Not likely they will care."

"Okay," Jason agreed.

Caitlin immediately went to work on his belt. Her expert hands had him open quickly and his dick free. Her fingertips teased the head making Jason moan softly. In seconds Caitlin could feel wetness on her fingers and realized he was leaking pre-cum. Her fingers smeared it around the head.

Caitlin looked into Jason's eyes but without waiting for any kind of response leaned down. Jason could feel her hot breath blowing on his cockhead as her fingers worked both his cock and balls. He leaned back to give her more room. He would have liked to put the seat down but that wouldn't work with the others in the back.

Jason next felt Caitlin's mouth engulf the big head of his cock. He groaned as she swirled her tongue around the surface of his cockhead and applied suction and increased hand strokes to add to his enjoyment. He groaned again a bit too loud and knew the others had to hear. He couldn't help himself though. Caitlin's mouth was talented and knew how to tease him to the greatest affect.

"Oh, god," Jason hissed as Caitlin descended lower.

He tried to be quiet but her mouth was feeling incredible on his cock. The combination of her hands and mouth were a lethal pair in bringing on his orgasm. He could already feel his nuts beginning to tighten for release.

Jason was just settling in to the blowjob and wishing he could see Caitlin's tits and feel her pussy when a vehicle pulled up about ten feet away. He looked over to see an older woman looking at him. She turned from looking as soon as their eyes met but he wondered if she saw what Caitlin was doing. Caitlin's head was below the side door but her ass was up in the air. It wouldn't take much imagination to know what was going on if the woman had noticed. Jason immediately felt uncomfortable.

Jason ran his hair through Caitlin's hair and managed to get her to look up. He nodded his head towards the door but Caitlin looked at him confused.

"Someone just pulled up right next to us," Jason whispered.

Caitlin looked out the window, "They can't see anything," she said.

"You don't think so? I know the woman saw me," Jason claimed.

"You think they care?"

"I don't know but it is just weird having an audience," Jason professed.

"You want me to stop?" Caitlin queried.

"No, but ... "

"I got an idea. Want to go back to our dorm?"

"Yeah, sure but what about ... "

"Hey, Nina. Want to go back to the dorm?"

Jason thought he heard sucking and Chad moan just before Nina answered, "What? Why?"

"A car is right next to us. Not much privacy," Caitlin stated.

Nina was now sitting up and Jason caught her face in the rearview mirror. Her lips were all moist. "Okay with me," Nina said. "You want to head to our dorm?" Nina was heard asking Chad. He must have nodded yes, because she replied. "Okay, Chad says."


Jason started the car and pulled away. Caitlin was still leaning over the console with her hands holding his erection. He glanced over at her as they drove down the road.

Caitlin smiled and said, "I'll keep going if you promise not to hit anything."

"I'll be careful," Jason said, smiling back.

Jason had trouble concentrating on the road with Caitlin lazily sucking his cock. She had him close to cumming twice on the trip to her dorm only to back him down. He was so horny he could have screamed by the time they arrived at the dorm parking lot. Fishing his cock back in his pants for the walk into the dorm would be difficult.

Caitlin leaned back to get out of the car like Chad and Nina were doing. She saw Nina glance over the seat, see Jason's big cock, lick her lips, and then smile at her. Caitlin was smiling as she turned back to Jason and his worried look. He wasn't moving.

"What's the matter?" Caitlin asked, but then realized and giggled. "You can't get him back undercover?"

"No ... thanks to you," Jason scolded but merrily.

Caitlin glanced around the full but quiet parking lot, "Lean back a little," she said.

Jason did as he was told, moving the seat. Caitlin gave him an amused smile as she settled back into his lap. Her mouth was once again around his cockhead. Jason glanced around but they were fairly safe in the darkened parking lot. Caitlin was quickly playing beautiful blowjob music on his cock again. He groaned as she brought his desire back.

"Oh, fuck! You do that so well," Jason grunted, getting closer to cumming.

Caitlin backed off only to say, "Thanks," then was back on his cock.

Jason wanted more from this hot chick though. His thoughts turned to her pussy and he found himself wanting that cherry. 'God, I've changed in the last few weeks,' he realized. 'Here I was accusing Mark of being immoral taking all those cherries. Now I'm the one that can't wait to pop another.'

If Jason didn't stop her soon he was going to explode in her mouth. He was so charged up he wanted nothing better but still he yearned for her pussy. He couldn't believe he was doing it but he found himself pulling her off his cock just before his balls reached critical mass.

"What?" Caitlin questioned, sitting up and not sure why he had stopped her.

"Ahh ... ," Jason stuttered, not sure how to tell her all of a sudden what he wanted. That he wanted to fuck her. He finally got out, "What about you?"

"What, oh ... I'm okay. I can get my kicks sucking you off," Caitlin claimed.

"Well, I'd like to do something for you," Jason stated.

Caitlin looked at him trying to read his face. Her hands were slowly stroking his saliva slick cock. She looked at him in such a curious way Jason wondered if he had asked too much. Finally, just as he was about to tell her forget it she responded.

"Chad and Nina are probably in our room by now. We could leave them alone and just climb in the back of the car." Caitlin asked.

"Sounds good to me," Jason agreed, unsure how they would have arranged things in the small dorm room anyway with Nina and Chad there.

Caitlin went first and Jason followed, staring at her ass as she went. Her weight loss program was paying dividends, he noticed. She didn't have that much to lose in the first place and her efforts were emphasizing the curves of her nice body.

In the back seat they fell into each other's arms kissing. The kissing grew hot and Jason's exposed cock still jutted for his pants, erect and leaking pre-cum. Caitlin saw it and slurped on the head of his cock for a while. Jason was so aroused he couldn't stand it anymore.

"God, Caitlin. I got to cum soon," Jason pleaded.

"You want me to finish you and then we can work to get him hard again?"

"Sure," Jason agreed, too far gone to care anymore.

Caitlin dropped her head back into his lap and half way down on his cock. Jason thought his head was going to explode as she began an aggressive attack on his dick. Her fingers teased his bloated balls and stroked his steely hard cock. Caitlin had three-quarters of his cock in her mouth and down her throat when he couldn't hold back.

"Fuck," Jason shouted.

Caitlin backed off his cock to the head just in time as Jason's cum blew into her mouth. She had teased him so much he came in buckets much like the first time she had sucked him. Her mouth struggled to remain sealed around his cockhead and gather the significant cum as it filled her mouth. Just when she began to worry she couldn't hold it all he slowed to a trickle. She sucked lightly on the head, gathering the last of his cum, before backing off and swallowing. Caitlin was glad to be able to breathe normally again.

BlewWater69
BlewWater69
2,580 Followers
12