The Cherry Poppers Ch. 07

"Sh... it ...," Stephanie grunted. "Oh, god, Jason. Don't stop ... please don't stop ... ahh ..."

Jason waited for her to finally relax before removing his mouth and slowing his teasing of her cunt with his fingers. Her juices had flowed from her cunt and he now lapped them up off his own fingers. When he was done he sat up a little to look at Stephanie. Her eyes were closed and her breathing raspy.

Jason pushed his running pants down over his fully engorged cock. It was starting to ache and he could see right where he wanted to put it. A blowjob would have to wait. He wanted in her virgin pussy now if she would let him. He figured he had earned it as her teacher and for two great orgasms. He moved into position between her legs. This brought Stef's eyes open. She stared at his monster cock for the first time.

"Oh, my god! It's huge!" Stephanie exclaimed.

"It's pretty good size," Jason admitted.

"Jason, please don't. It's going to kill me," Stephanie pleaded.

"It'll be fine," Jason stated, trying to assure as a voice of experience.

"It's too big!" Stephanie contented. "I've never ... I mean ... it's going to hurt too much for my first time."

"I've done a few before you," Jason professed.

"A few virgins?" Stef questioned.

"Yes."

"You have?" Stephanie continued to query, not sure she could see that thing inside her or anyone else either.

"Yes, just relax. Let me take charge," Jason said. He had to admit he was getting experienced at this.

"I don't know," Stephanie still pleaded. "You're too big. It's going to kill me."

Jason rubbed the head of his cock back and forth tenderly in her slit. Her wetness from two cums and his mouth let it slide easily. The feeling felt great to both of them and Stephanie sighed despite still being very nervous. He worked it slowly on the surface and against her clit. Stephanie moaned with the contact. She stiffened though, when he pushed the head into her opening on one backward stroke.

"Oh, mother of god!" Stephanie shouted. "Jason, it's going to hurt too badly!"

"It will hurt for a brief moment but you'll be fine. You're pussy is primed from your two orgasms," Jason evenly stated, like the voice of reason and knowledge.

"It's so big."

He shoved forward a little, lodging the head into her cunt and encountering her cherry. 'Here is another one for me to pop,' he realized. Jason studied Stephanie's face. It was painted with fear and the discomfort she already felt. He hoped this was easy for her.

"Oh, god, Jason," Stef croaked.

"Stephanie, what are you?"

"What do you mean?"

Jason shoved hard forward. His cockhead ripped apart her hymen and penetrated slightly beyond. She screamed and hung to him with white knuckles. Jason stayed perfectly still while Stephanie endured the pain. He watched her face and the tears forming in her eyes.

"You're a woman now, Stephanie," Jason announced.

"It hurts, Jason. Oh, god, it hurts."

"Just relax a minute," he said, not moving.

It took several more minutes but eventually the worst of the pain passed. Jason still waited until the pained look began to drain from Stephanie's pretty face. He slowly started to move. It was just a fraction at first and a little more each time if she didn't protest. Stephanie became accustomed to his girth but he still was only partly in her. When he pressed forward, she would stiffen again. It took a while before he was able to go much deeper.

Stephanie's pussy was extremely tight but slowly adjusted to the large intruder. Jason started slowly and kept his strokes relatively shallow for a while. Stephanie still clung to him but he could feel her relaxing a little and her pussy began to react with more wetness. He kissed her lips and her cheeks where the tears had wet them. A couple times he stopped moving and kissed and sucked on her nipples. Stephanie seemed to like that.

"I am a woman now, aren't I," Stephanie said out of the blue at one point.

"Yes, you are," Jason agreed. "And from now on you'll feel the joy of being a woman."

"I hope so," Stephanie proclaimed.

Jason took his time. He even sat up a little from time to time, just high enough to see over the ridge and the tall grass. He didn't see anyone and felt they were still alone despite her earlier scream. Pretty soon he was able to establish a decent pace fucking Stephanie. She groaned but didn't seem to want him to stop. At one point she even grabbed his sides and pulled him to her.

Jason's dick felt incredible inside Stephanie. Her pussy was warm and wet. The tightness was incredible and he was able to go pretty deep inside her now. Part of his cock was still outside her womb but she was taking nearly six inches and not protesting. He could feel his balls churning. They were excited by this pretty girl and his taking of her virginity. He tried not to think conceited thoughts like, 'this is my sixth virgin,' but like any guy, those thoughts crept into his head even as he fucked her still.

He wanted Stephanie to cum for her first time. Mark had expressed to him the importance of trying to get the girl/woman off the first time so she would know the joys of sex and not just the pain. Jason kept up a pace that allowed him to simmer while bringing Stef along. It took a while but eventually she was meeting his thrusts and even pushing back. Her moans changed too from discomfort to ones of pleasure.

"Jason, it's starting to feel good," Stephanie said at one point, as if she was surprised herself.

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

"Oh, god. It feels good. You're so huge inside me. It feels like you're up in my stomach," Stef remarked.

Jason realized they hadn't planned for birth control. "Stef, do I need to pull out?"

"Oh, Jason ... geez ... you better," Stephanie stated.

"Okay," Jason said, with a little disappointment in his voice.

He would have loved to stay inside her when he came. But she was right, he needed to pull out and not risk pregnancy. Cumming inside her would have been so sweet, he knew.

Jason continued at a steady pace until Stephanie showed advanced signs of her pending climax. He picked up the fucking speed when he sensed she was close. He was pretty sure he could last himself but it had better be soon too he realized. It was, for Stephanie urged him faster.

Jason was fucking her good now. Stephanie was groaning loudly and guiding him to her with each thrust.

"Oh, fuck me, Jason. Keep fucking me. It feels so good. Ahh ... "

Jason sped up and fucked her at near full clip. His own orgasm was straining his balls. He tried to think of other things but her pussy was just to incredibly tight so they never lasted long. He was thankful when she eventually exhaled loudly and bucked off the ground.

"God, I'm cumming ... cumming so good!" Stephanie shouted, louder than Jason would have liked.

"Me too," Jason gasped, trying to hold out for a few more strokes for her.

"Oh, my god ... cumming ...," Stef croaked.

"Oh, fuck," Jason yelled, and he pulled back quickly, extracting his cock from her cunt.

Stephanie was too far into her own climax to care too much, but she could immediately feel the loss of his cock from inside her. It felt like cold air was rushing into her now that he had stretched her open. Her pussy seemed sad, like she was, for the loss of its new friend. However, Stephanie could feel shots of something hot and wet between her tits and over her belly.

Stephanie opened her eyes and tried to focus down between her breasts. What she saw intrigued her immensely. The little hole in Jason's cockhead opened and a fairly weak pulse of white viscous cum shot out onto her belly just above her pubic hair. She could see more of his cum right beneath her chin, between her tits, and a trail down to where the last shot had landed. As she watched, still coming down off her own orgasm, she saw his cockhead leak more cum into her pubes. She had missed all the forceful blasts but watched transfixed as his cock continued to leak more cum.

She had never seen a guy's cum before other than in a porno a high school friend of hers had shown her. In real life it was far more fascinating. Her right hand stole up to her chest and dabbed tentatively into one of the cooling whitish puddles. It stuck to her finger and made a trail from the puddle to it as she pulled her hand slightly back. She rubbed it between her fingers feeling the gooey texture. 'God, it's his seed,' she realized.

Jason was up on his strong arms over her. He watched as she touched the cum on her chest. She looked amazing to him bathed in his spunk. 'Not much sexier,' he thought, 'than a woman wearing a guy's cum and playing with it.' Jason moaned softly at the end of his orgasm. He slid back onto his heels and looked up Stephanie's body. She had cum between and on the insides of both tits. Her belly was covered and her pubes were streaked with his cum. He could see the whitish residue of her own juices around the entrance to her pussy. He didn't see much blood, only a faint hint of pink in her cum on one side. He stared amazed knowing he had just been the first to enter that hole.

They looked at each other until they were breathing normal. Jason glanced around but still no one seemed to be nearby. He turned back to look at Stephanie and smiled.

"You alright?" he asked.

"It hurt badly at first but that was fantastic at the end. You're good with a girl ... woman, Jason," Stephanie praised, happy to now be able to be called a true woman.

"Thanks. A little experience helps," Jason admitted.

"Exactly how many girls ... women have you fucked that were virgins?" Stef quizzed.

"Six," Jason stated, suddenly feeling a little guilty for deflowering that many himself.

"Wow! That is a lot, isn't it? I mean I don't know but I would think that was a lot."

"I think it is compared to most guys," Jason agreed.

"Well, I guess I picked the right guy then with experience to help me," Stephanie decided.

"I guess so," Jason said, reaching for his pants, uncomfortable with the discussion.

"What do I do about this?" Stephanie asked, indicating the huge load of cum cooling on her skin.

Jason couldn't think of anything else so he used his jock strap to wipe her off as best he could. It got most of it and he pulled his pants on without the strap. He shoved it into his pocket. They dressed quickly and headed back. They passed three people running, two guys and a girl, on the way back. It was doubtful they had heard anything, though, as they were still heading towards the field on the path.

They walked back since Jason no longer had anything protecting his cock from flopping about in his running pants. It gave them plenty of time to talk. Stephanie thanked him repeatedly for being such a thoughtful and caring sex partner. Jason tried to remain humble and not embellish on it too much. He was surprised, though, when Stephanie asked what's next.

"Next? What do you mean?"

"Well, Jason. Even I know there is something we haven't tried," she said and put her finger seductively into her mouth.

"You want me to teach you to do that too?"

"Sure! Since you're such a good teacher and all."

"Well, I suppose I could," Jason said, not believing his own reluctance.

He worried where this was headed though. He already had a submissive to contend with, two hot babes in Claire and Caitlin, he'd love to fuck Kim again, and now Stephanie practically begging him to teach her the ways of the Kama Sutra. How much could one guy handle and he was supposed to be fucking virgins. 'Oh, god,' he thought, and visions of that redhead at the party came to him.

"It'll be fun," Stephanie was saying as he picked back up on the conversation.