tagFirst TimeThe Cherry Poppers Ch. 10

The Cherry Poppers Ch. 10

byBlewWater69©

Jason headed back to his frat room to plan out the weekend. It would take exact timing and plenty of preparation if his plan was going to work. He felt that a good plan, no matter how farfetched or difficult, could be accomplished if the planning was precise.

When he was ready, he dialed Stephanie, but not her cell phone; he called the room hoping to get Pam first. This first part of his plan was shaky, he admitted to himself, but necessary to get the ball rolling. Luckily, it worked and Pam answered the phone.

"Hello," Pam said.

"Pam, it's Jason," he said.

"Hi, Jason. I'll get ... "

"What're you up to on this Friday night?" Jason asked.

"Oh, nothing much. I have studying to do ... "

"You shouldn't be sitting home studying on a Friday night," Jason stated.

"Well, maybe not but ... "

"Is Stef there?"

"Yes, I'll get her for ... "

"Do you know if she has plans?"

"I don't think so but here, you can ask ... "

"I'm going to ask her to dinner. Would you want to go too?" Jason asked.

"Aah ... well ... I don't ... it would depend on Stef," Pam concluded.

"Let me talk to her please?" Jason asked.

"Okay," Pam said, somewhat glad to be able to pass the phone.

"Hi, Jason," Stephanie said coming on the phone.

"Hey, Stef. My date cancelled for the night. You up for going to dinner?"

"Sure," Stef replied.

"I feel bad though. I asked Pam what she was doing and she said nothing. Shouldn't we be nice an invite your roommate too?" Jason queried.

"Aah ... I ... aah ... guess that would be okay," Stephanie agreed tentatively.

"I think you're right, Stef. It's only dinner and we can drop her off later."

"Sure."

"After all, won't want her knowing about your lessons," Jason said chuckling.

"Yeah," Stef agreed but didn't chuckle too.

"You haven't told her, have you?" Jason questioned.

"Aah ... I wouldn't ..."

"I mean it's okay if you have and I know roommates like to discuss everything. I talk to Chad about a lot of things too," Jason offered.

"You do? Did you tell him about us?"

"Stef, I had to kick him out of the room the other night when you came over, remember? What do you think he suspected?" Jason questioned.

"Yeah, I guess you're right, but you didn't tell him about the ... aah ... I mean the ... "

"Lessons? No. Just that you would be over and we wanted to be alone."

"Oh, okay."

"Have you told Pam?"

"Well, sort of," Stephanie confessed, whispering now.

"You did? What did you say to her?"

"I told her lots of the things I've learned," Stef allowed quietly.

"What did she say?"

"Oh, god, Jason, she was just amazed," Stephanie whispered into the phone.

"We can talk more about it later," Jason said.

"We can ...?"

"Ask her if she wants to go," Jason stated.

He could hear the two women talking but it was muffled. Stephanie probably had her hand over the phone. It took about a minute but then Stef came back on and said it was all set and Pam would join them.

"I'll pick you up at six-thirty," Jason said, it was four-thirty.

"Okay, we'll be ready. How should we dress?"

"Nice, dresses preferably," Jason stated.

"Really? You mean it? I mean ..."

"Is that a problem? I have a very nice place in mind."

"Jason, we don't have much money ... "

"Don't worry, I've got it covered," Jason proclaimed.

"Okay, we'll be ready."

Jason hung up with Stef, impressed with himself he had pulled it off. That had gone almost exactly as scripted. All he had to do now was get them talking about the training. At some point he could offer to train Pam too. He made the dinner arrangements at a fancy French restaurant. He hoped to soften the women with good food and wine. It didn't hurt that one of his frat brothers was a waiter there. He briefly thought, 'God, I'm getting really devious trying to pop these cherries. I hope this isn't changing me.' He dismissed the thought quickly.

The dinner went exactly as planned except he had a hard time bringing up the subject of training. They had a wonderful time and the ladies looked gorgeous even though they lacked really fantastic dinner dresses. They both had on the best dress they had at school, which was still quite elegant. Stef's was red and worked well with her dark hair. The dress showed her improving shape and left her cleavage very much in view too. It made Jason wonder how she ever fit in it before the diet. Pam's dress was blue and hugged her sleek frame as well. She didn't have the curves Stef had but made up for it with lots of expansive exposed leg on her tall frame.

Jason hoped to talk to the two roommates alone about the training but when one went to the ladies room, they both went, so that didn't happen at dinner. The food was fantastic and they drank two bottles of wine with it. They split two desserts and Jason paid the bill despite protests from Pam that she should pay her portion.

As they were reclaiming their coats from the coat room, Pam said she needed to run to the bathroom again. This time Stephanie remained with Jason as he gave the valet the ticket for his car. As they waited, he had a few minutes to talk with Stef. The ladies seemed to have more of the wine than Jason and Stephanie hugged his arm affectionately as they waited for the car.

"Shall I run you both back home?" Jason asked.

"Oh, do we have to end the evening so soon?" Stef said, squeezing his arm.

"What do you have in mind?" Jason questioned.

"I don't know. It was such a lovely evening though, I was hoping it didn't have to end."

"Well, it's only nine-thirty. We could do something else. You think Pam wants to head back?"

"I don't know. What're you thinking?"

"I'm thinking how great you looked in that dress tonight. Pam too. Maybe you need some more training," Jason queried with a smile and a kiss.

"Maybe so," Stef agreed and kissed him back.

"I can't wait to get that dress off you," Jason claimed.

"Oh, really," Stephanie mused. "What about Pam?"

"What? You want me to remove her dress too?" Jason asked playfully.

"No, I didn't say that," Stef proclaimed but with a giggle.

"You think she could use some training too?" Jason asked, hoping to plant the seed he wanted.

"Oh, is that why you invited her? So you could train us both?" Stephanie questioned calmly and astutely.

"No, of course not, but the poor girl shouldn't be left home on a Friday night."

"I guess not but I thought we were going to be alone tonight afterwards. Isn't that what you said? I wanted you all to myself."

"You want me to take her home?" Jason asked.

"Well, what are you thinking about?"

"I was thinking about us all going back to my place for a few more drinks," Jason allowed.

"Pam too?"

"Sure, we're all having so much fun. That is unless you want me ... "

"No ... okay. It's okay," Stephanie agreed.

The car and Pam both arrived back at that moment. Jason helped the valet open doors for the ladies and they were soon off to the campus. Pam said something about the wonderful desserts and the conversation on the dinner lasted about half way home.

"What're we doing now?" Pam asked. "You need to take me back?"

"Only if you want to go back. Stef and I decided we would all go back to my place for more drinks," Jason told.

"It was great of you both to have me out with you, but I should leave you two ... "

"Nonsense, we discussed it and agreed we'd all head back to my place, right, Stef?"

Stef glanced at Jason but said, "Yeah, Pam, we're going to have a few more drinks at Jason's.

"Well, okay, if it's okay with both of you," Pam allowed, not really wanting to head home already either.

Jason parked his car behind the frat as usual and walked the ladies to his room. Chad was out with Nina for the evening, so they had the place to themselves. Jason opened more wine, not wanting to get anyone sick mixing drinks, and served glasses to the both of them. They listened to music and talked until Jason broke out a deck of cards. By the second glasses of wine somehow the game turned to poker.

"What're we playing for?" Stef asked with a giggle caused mostly by the wine.

"Me to see you take that dress off," Jason stated joking.

"Not fair. You have more clothes on than we do," Stephanie countered but still laughing and with Pam agreeing as well.

"All the better," Jason claimed with a laugh.

"What about me?" Pam questioned.

"You can take your dress off too when you lose," Jason replied.

"Oh," Pam said, but stopped there even though she looked like she might say something else.

Jason began to think he might get what he wanted without any discussion of training Pam. He lost the first hand and so did Stef. The girls jokingly argued that jewelry counted and Jason allowed her to just remove her bracelet. He removed his shoes and they dealt again. This time Jason won and both girls took off jewelry. The third glass of wine preceded the next hand and Stef won. Jason lost his socks and Pam the last of her jewelry like Stef. A couple more hands and Jason lost his watch and the girls their shoes. The next loss would start the fun. Jason half expected them to call an end to the game but they didn't.

Pam won the next hand and Jason had to remove his shirt. He still had a tee on underneath. Stephanie had nothing left, so her dress came off. Jason and Pam both cheered and whooped when she stood and unzipped it. Her lacey bra underneath barely contained her huge tits and matched her panties in pink as the only remaining articles of clothing. Jason won the next hand and Stef had to remove her bra. He expected her to quit but instead she took it off letting her magnificent breasts swung free, the nipples excited already. Then he got to watch Pam stand and removed her dress. She acted very shy about it, despite the alcohol, but went through with it.

Jason watched, as did Stephanie, as Pam undid the zipper and removed the sleeves from her arms. The dress dropped down to her waist revealing her much smaller bra covered breasts. They might have been less than half the size of Stef's but they worked for her on her tall slender body. Her flat tummy flared out to nice hips and those long shapely legs made Jason's cock begin to harden in his pants. Her baby blue bra and panties looked exquisite on her.

Stef won the next hand and laughed heartily that they would be the ones going next. Jason decided to keep things interesting and stood to remove his pants rather than his undershirt. Both girls watched with rapt interest as his semi-hard cock tented the front of his boxers before he sat back down. Pam was next and shyly removed her bra. Her arm tried to cover her nipples afterwards but Jason got a quick look. They were nice breasts, just not a good comparison to Stephanie. Her nice sized areolas were chocolate brown, as were her nipples, and distended they looked quite suckable, like Hershey's kisses.

Jason drained the last of the second bottle of wine into their glasses. While he moved around, the girls giggled together, and watched his now hard dick bounce with each step. When Jason sat back down, Stef came to him and stole her hand up his boxer pant leg. She leaned over and kissed him. They were all joking around and laughing but Stef's hand caused his boxer's to ride up and the head of his cock protruded. It was in her hand now but Pam could definitely see it. As Stephanie kissed him, he noticed Pam's eyes on his cock and then they meet. The smile on her face had changed to a more wanton look.

Stephanie and Jason broke the kiss. Stef was looking into his lap and teasing his cockhead with her fingers when he motioned for Pam to come next to him on the other side. She hesitated briefly but then crawled over. Stef glanced up to see Pam moving but instead of saying anything, just lowered her head. Jason moaned as he felt Stef kiss his cockhead and then take it into her mouth. He put his arm around Pam's shoulder and pulled her close. His lips met hers in a sweet first kiss.

Pam had long since stopped trying to hide her tits and Jason's hand found her taut nipple. He teased it gently at first and then more urgently as they kissed passionately and Stef sucked his cock. Jason was so turned on with the two of them, he was sure he was feeding some pre-cum to Stef as his dick reacted. Pam moaned in his kisses and helped him remove his shirt. He leaned back and let Stef remove his boxers. He had pulled Pam over him so he could suck on one nipple while he tweaked the other. Jason swore he felt her shudder with a small orgasm as he plied her tits.

Wonderful Stephanie was busy practicing her deepthroat skills when Jason resumed kissing Pam. His one hand had slid down her flat belly and found the wet spot on her panties. His fingers were making Pam moan into his tongue active kiss. They were teasing the material of her panties into the seam of her sex. The pressure on her clit was making Pam gasp and kiss him more urgently.

"Oh, fuck, Jason," Pam moaned quietly.

"Take them off, Pam," Jason whispered back into her warm wet mouth, her thick brown hair hanging over their faces.

She complied quickly and they resumed kissing. Now his fingers played in the crease of her cunt, drawing more moans from Pam. Jason also groaned as Stephanie sucked his cock deliciously and palmed his balls. They were beginning to draw up tight to his cock but he didn't want to cum yet. 'How do I do this so I can fuck them both,' he thought.

Jason could tell that Pam was getting close. He slid a finger into her hole to check her barrier. He was surprised when it met little resistance and eased right into her hot tight cunt. Had he been wrong about her being a virgin or was there some other reason. He forgot about it as Pam groaned with the exquisite feel of someone else's finger in her pussy. Jason's thumb rubbed over her clit and it sent Pam over the edge. She gasped into their kiss as the blissful waves of pleasure coursed through her body.

After Pam had finished cumming, he broke the kiss with her to tell Stephanie to mount him. Pam and he watched as she quickly dropped her soaked panties and climbed over his waist. She loved riding his cock most of all and wasted no time settling down over it. She was so wet, the steely hardness of his cock plunged right into her core. Stef gasped as the big cock spread her open and filled her wonderfully. She settled all the way down before starting to move slowly.

"Come up here," Jason said to Pam, indicating she should straddle him.

"Oh, god! What're you going to do?" Pam squealed.

"I'm going to eat you, my dear," Jason responded with a broad grin. "Anyone ever eat your pussy before?"

"No," Pam growled with lust.

Jason used his hands to guide her tight ass over his face. He couldn't see Stef now but he could feel her slowly working his cock in and out of her cunt. She would grind her pussy down on his cock when she had him in deep. It felt great to Jason but better to her. He was thankful she had chosen to go slowly; it gave him time to relax and settle into the fuck without too much worry of cumming. Stef, on the other hand, was getting closer by the minute.

Pam gasped when Jason started kissing her inner thighs. She had her back to Stephanie and looked down at Jason between her arms that supported her. Her long legs splayed out on either side of his head to get her pussy to his mouth. She shuddered when his tongue found her folds and started licking them. She purred like a kitten when he probed his tongue deep into her furrow and found her hole. The purr turned to a near roar as he pushed it inside and wiggled it around her hyper-sensitive opening.

"Oh, god, Jason. Don't stop ... please don't stop," Pam begged.

"Fuck," Pam heard Stef shout behind her. "God, I love this cock."

Jason had no intentions of stopping. She tasted delicious and he wanted more. He eased a finger into her from behind and Pam squealed again. Jason moved his mouth up to find her clit. He circled it with his tongue several times before sucking the knob into his mouth. That was all it took and Pam lost it. She screamed and he felt her juices flood his finger. He eased his mouth down to replace his finger and capture her nectar. He feasted on her cum as Pam ground her pussy into his face.

From somewhere, it seemed far away with his ears covered and face buried in Pam's cunt, he heard Stef scream too. He could tell she was cumming as well from the way her cunt was clamping down on his cock and trying to milk the cum from his balls. Fortunately he wasn't ready just yet and managed to hold off somehow. He had to try to think of other things though than the true erotic scene taking place in the room. Jason couldn't focus on having one hot girl getting off on his cock and another in his mouth if he hoped not to lose it himself.

When both women had shuddered through their respective orgasms and lay still gasping for air, Jason managed to push Pam to the side. The sight of Stef, with her huge tits quivering off the last of her climax, nearly drove him there. Somehow he managed to keep in the moment.

"Pam, switch with Stephanie. Stef, come let me eat you, babe," Jason commanded like the maestro with an orchestra.

"What?" Pam queried as if making sure she heard right.

"Climb on my cock," Jason instructed.

"But, I aah ... I've never ... "

"What's the matter? You don't want to fuck me?" Jason asked.

"It's not that. It's just that ... "

"She's a virgin like I was," Stef said. "It's okay, Pam. Fuck him if you want to."

"But he's your boyfriend," Pam questioned.

"He's not my boyfriend, are you, Jason? He's got other girls too. He's just teaching me the ropes like I told you. Isn't that right, Jason?" Stephanie extolled.

"Aah ... yeah, that's right," Jason replied, surprised Stephanie was taking this so well.

"He can teach you too like we discussed," Stephanie said.

'Like they discussed? Who was using whom?' Jason wondered. 'Had they planned this all along? Had his great plan played right into their hands?'

"Okay," he heard Pam acknowledge.

A somewhat stunned Jason watched the two women change positions. They both watched as Pam squatted above him with her long legs. Stef helped her align Jason's cock to her cunt hole.

"Okay, just settled down on it slowly," Stef instructed like she was now the teacher.

"Oh, god," Pam gasped as the big head lodged into the opening of her virgin pussy.

"That's it. Go all the way down slowly. When you can't take anymore of his big cock, start going up and down easy," Stephanie explained.

They both watched Pam impale herself on the big cock. She grimaced as the monstrous intruder invaded her extremely tight wet passage. She seemed to whimper a little at the beginning but didn't stop until most of Jason's cock had disappeared inside her.

"You're much bigger than her finger," Stef whispered to him as she now straddled his chest, her big tits slapping his head on either side like soft pillows.

"She took it pretty easily," Jason whispered back to Stef.

"She lost most of her barrier to her finger a while ago," Stephanie offered. "She's still a virgin though, another for your collection."

"What collection?" Jason asked, not sure how she knew.

"Remember you told me in the field that you had done five others and I was the sixth. Now you have seven," Stef claimed smiling at him.

"Oh, that," Jason sighed, somewhat glad his secret was still intact.

"Any more virgins I can help you deflower?" Stef asked quietly amused.

"I don't know," Jason whispered. "You know of anymore?"

"Maybe," Stephanie retorted.

He couldn't tell her they had to be on Dr. Jenny's charts as such, "You dropping any names?"

"Not yet," Stef chuckled.

"Then sit on my face," Jason commanded.

"Gladly," Stef replied.

Jason could feel Pam working her pussy on his big cock as Stef moved into position over him. Pam's pussy was so tight he hoped he could hold out long enough to get her off. As Mark had always said, that was a big part of the job of a cherry buster: make sure the lady cums the first time.

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byBlewWater69© 2 comments/ 95546 views/ 6 favorites

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