Chapter 11: Jeff's First Time

Jeff's mouth dropped open. Had he really heard her correctly?

"Er ... what?" he asked.

"Look, Jeff, I know you're a real gentleman, but I've been flirting with you all night, and you haven't made a move yet. I'm really starting to get impatient."

"I ... I don't..."

"Let me spell it out for you. I want to have sex with you. There. Now, are there any objections?"

"Um ... no objections here," he said.

"Good." She reached around behind her back, undid her top, and took it off. Jeff's heart literally skipped a beat as he saw he bare breasts. They were every bit as beautiful as Allison's! Rachael then slid the bottom half of her swimsuit off, and Jeff found himself looking at a real live naked woman for the first time in his life.

"Now your turn," she grinned, and grabbed the waistband of his suit.

"Hey!" he exclaimed, but she giggled and pulled it down. His rock-hard member sprang free.

"That looks delicious!" she said, staring at it. Then she put her hand on it, and he felt an exciting thrill. It wasn't the first time a girl had ever touched him there, but knowing what was going to come later made it feel twice as good!

Her hand stroked it up and down, sending wave after wave of pleasure through him. She smiled at him as she did so, showing that she was enjoying this teasing.

"But we have to do this right," she said. "If this really is your first time, you want to do it in your bed rather than on this uncomfortable old couch." She released his cock and stood up, grabbing his hand and pulling him to his feet. "Come on," she said.

"Where are we going?"

"Up to your bedroom," she replied.

"But we're naked!"

"I should hope so. We're about to fuck, aren't we?"

"But what if Brit catches us?"

"Wouldn't that be funny?" Rachael laughed. "Anyway, we'll be careful."

Still hesitant, he allowed her to lead him up the stairs to the front room. It was all dark up there, and they took a few minutes to let their eyes adjust. To Jeff, it seemed that she picked a spot right in the middle of the house to wait, where she could be seen from just about every room. Jeff was a ball of nerves. What if Brit came down just now for a drink of water?

But it didn't happen, and a minute later Rachael led him to the staircase.

He had never noticed the creak of the stairs before, but now it sounded like even the tiniest of noises echoed through the house. He almost held his breath going up those stairs, but somehow, an eternity later, they made it to the top. It was just a quick trip down the hall to his bedroom.

Rachael, however, had other plans. Instead of stopping by his open door, she led him past it.

"Where are you going?" he whispered.

"I thought it would be much more fun to take the scenic route," she whispered back. As they neared Brit's door, he realized that it was open!

"She'll be able to see us!" he whispered in alarm.

"Not if she's asleep."

"But what if she's awake?"

"That's a chance we'll have to take."

Jeff tried to pull away, but Rachael grabbed him with her other hand and pulled him harder. To avoid making a ruckus, he had to give in. His heart pounded in his chest as he realized where Rachael was leading him: right to Brit's door!

He opened his mouth to protest, but it was too late. Even a whisper would be too loud here. Frightened half out of his wits, he found himself entering his little sister's room.

She lay there sound asleep in her bed, to his immense relief. But what if she woke up? Rachael and Jeff were standing there completely naked in front of her.

"Isn't she adorable?" Rachael whispered, and Jeff put his finger to his lips in a gesture for silence. But Rachael released his hand and walked over to the bed. Jeff stood there petrified in fear. What was she going to do? Was she going to deliberately wake Brit?

As Rachael leaned over and kissed her on the forehead, Jeff felt panic rising. That simple touch might be enough to wake her. But the girl didn't stir, and Rachael silently walked back over to him.

"Can we get out of here now?" he asked.

"Not yet," Rachael responded. "First you have to kiss me."

"Kiss you?"

"Yes."

"Here?"

"Yes, I want your first kiss to be with me, right here, in your little sister's room, right in front of her. You have to admit, this will definitely make it memorable."

But--"

"Kiss me or I wake her up."

Jeff leaned in and tried to give her a quick peck, but Rachael grabbed him and pulled him into her. He nearly lost his footing, but managed to keep from falling. Pressed up against her naked body and with their lips locked in a passionate kiss, he felt both excitement and fear.

Then he felt Rachael's hand go to his cock, and she began to stroke it again. Jeff tried to pull away, but she held him fast. Did she actually mean to have sex with him right here in Brit's room?

She let it go on for another five minutes, then pulled away. "Okay, I think I've tormented you long enough," she whispered, and finally they passed through the bathroom to his room. He quickly closed both bathroom and hall doors and locked them, then Rachael turned on the lights.

Jeff squinted in the sudden glare, but it only took a few seconds for his eyes to adjust. The two of them stood there naked.

"I hope I didn't scare you," she whispered. "No, on second thought, I hope I did. I don't know about you, but there's nothing like a little shock or panic to get me in the mood."

"Well, in my opinion there's nothing like a little shock or panic to scare me out of the mood."

"You're just not used to it. So we'll just have to work on it some time."

"You don't have to, really," he said.

"We'll save those lessons for later. You were such a good sport, I think it's time for your reward. But first, you have to answer a few questions, so I can find out the best way to treat you."

"They're not going to be like those questions from earlier in the evening, are they?"

"Not just like them, they are the questions from earlier in the evening. First, are you a virgin?"

"That's none--"

"If I'm going to have sex with you, I think it is my business. Tell me the truth, Jeff. Look, it's easy. Whether you're a virgin or not, you won't be five minutes from now, so it really doesn't matter, does it?"

"All right. I am. Satisfied?"

Rachael grinned. "I was hoping I got to be your first. I don't want you to have any preconceived notions when I teach you how to have sex the Rachael Craven way."

"And I take it you're an expert?"

"You'd better believe it. Now, I have just one more question, and again, I want you to be honest. Have you ever had an orgasm before?"

Jeff sighed. "Oh, all right. Not that I remember, and I'm sure I would know if I had, so I'm going to have to say no."

"That's even better," she grinned. "Jeff, this is going to be a night you'll never forget." She stepped in close, put her arms around his neck, pressed her body up against his and kissed him. Since she was actually half a head taller than him, she had to lower her head and he had to raise his, but it all worked out in the end. At first he was too startled to do anything, but as she continued kissing him, he just did what came naturally. Her mouth opened, and her tongue probed his. She sought out his tongue and began teasing it with her own. Getting into the spirit of it, he reciprocated by rubbing it up against hers.

A moment later she broke away, smiling at him. "We'll have plenty of opportunities to practice that later," she said. "I could sense your inexperience, but it's nothing we can't fix with a few practice sessions."

"You're making this sound like school," he said.

"It is. Sex-ed, to be precise. But with less emphasis on theory and more emphasis on practice. Unfortunately they don't give degrees in this, so you're just going to have to trust me that I'm qualified to be your teacher."

"You must be the stereotypical hot teacher that all the boys in the class fantasize about."

"And most of the girls, too. You're fortunate to get this one-on-one tutoring from the most popular teacher in the school. Usually I prefer bigger class sizes, if you know what I mean."

Jeff laughed. Apparently she was into orgies, which wasn't surprising.

"But for right now, I'm all yours," she told him. "Now, since this is going to be your first orgasm, we need to do it right. So I'm going to give you a choice. Do you want to stick it in my pussy, or my mouth?"

"Your mouth? Really?"

"Haven't you ever heard of a blowjob before?"

"Yeah, I've seen pictures of them on the Internet, and Allison--" He suddenly paused, realizing that he had just about revealed that he had seen that video. Did Rachael know about it?

"What about Allison?" Rachael grinned.

"Um ... I..."

"Did you spy on your father and stepmom or something?"

"No! Of course not!"

"And you said you've never had an orgasm before. Knowing Allison, if she had given you a blowjob, you definitely would have had an orgasm. So I'm guessing you saw a certain video on the internet, right?"

The bright red color of Jeff's face gave him away. Rachael merely gave an amused laugh.

"Oh, don't worry, Jeff," she said. "I know all about that video. I've got a copy of it myself. Great masturbation material. I never fail to get myself off when I watch it."

"Does ... does Allison know?"

"Of course. There's really no reason for her to hide it from me, since I'm the one who convinced her to have sex with him. He was my boyfriend at the time, and I thought she'd get a kick out of fucking him. She's always liked trying new things, and the idea of doing it with one of her students got her really excited. Of course, if I knew he was going to set up a hidden camera, I would never have let it happen. As soon as he put that video up on the internet, I dropped him like a rock. No one hurts my sister like that and gets away with it."

"You mean ... you let your own sister ... have sex with your boyfriend?"

Rachael shrugged. "Why not? Allison likes to share her guys with me, so why shouldn't I reciprocate?"

Jeff gasped.

"But we're getting off the subject. We were talking about blowjobs. Specifically, me giving you one."

"Yeah!" he exclaimed, excited. "Just knowing how sensitive I am there, I'd imagine it would feel pretty good."

"You'd better believe it. Though I can't confirm it for obvious reasons, I've heard that the most fulfilling orgasms for men are in a girl's pussy, but for the most intense orgasms, you just can't beat getting sucked off. So do you want to try it?"

"Um ... will I get another chance to put it in your pussy?"

"After we sleep for a few hours first. You're young enough you should be able to have multiple orgasms, but since this is your first time, you haven't built up the stamina you need. Especially since I'm going to make sure the one in my mouth blows your mind."

"So you're going to blow my cock and my mind at the same time."

Rachael laughed. "I love it when you talk dirty. Go lie down on the bed and let me take care of you."

Jeff did as instructed, eager to get on with the activities. He couldn't believe she was going to actually suck him off!

But rather than get right to the action, she lay down next to him, leaning in and putting an arm around his neck. She kissed him on the cheek.

"But I thought..." he began.

"The longer you build up to it, the better it feels," she explained. "And I'm aiming to make you pass out from the pleasure."

"That shouldn't be too difficult, with my inexperience."

She slid over on top of him, and he felt her amazing chest rubbing against his own. Instinctively he wrapped his arms around her waist. She smiled, then lowered her lips and kissed him deeply and passionately. He was in heaven; here was this astonishingly beautiful woman seducing him, something he had only dreamt of before. How could such a wonderful experience possibly be true?

She lowered her head a couple of inches and kissed him on the chin, her eyes still staring up at him. That sent thrills through him, perhaps because of the thought of this dominant woman taking a submissive position. As she lowered to his neck, he shivered from the chills running down his spine.

She touched the tip of her tongue to his neck, and he literally jumped from the sensation. Rachael giggled. "Just pulling out an old standby from my bag of tricks," she explained. "I can tell you liked it."

"Oh god, yes!" he smiled.

She did it again, but this time he merely gasped. She began to bathe his face and neck with kisses, driving him wilder and wilder with passion. By the time she finished, he was groaning in pleasure. The wide grin on her face showed that she enjoyed doing it to him.

She lowered herself to his chest then, kissing him first on the shoulders and along the collarbone. While this felt nice too, it was a more subtle pleasure, perhaps designed to cool him down a little so he wouldn't lose it too early. He relaxed and let the sensation overcome him. Then she lowered again, this time kissing him in the center of his chest. She moved to the side and made a circle around his nipple, at first a couple of inches away but circling slowly toward it.

"Not quite as fun as doing this to a girl," she said, "but it works on a man too."

His breaths were coming in gasps now as that circle grew tighter, especially as she teased him with that reference to sapphic love. His body was becoming more aroused and more sensitive as each second passed. The anticipation was almost painful.

Then she flicked her tongue against the nipple and he shook with the pleasure. Rachael certainly knew how to drive him crazy! Her tongue worked over the nipple energetically, almost savagely, and he began to groan once more. She worked it for several minutes until he thought he couldn't take it any more, then moved over and began to give the same service to the other one.

She was absolutely right about drawing out the experience. It was an exquisite torture as she kept stimulating him for as long as possible. She worked her way down his chest to his stomach, but only millimeters at a time. She deliberately avoided any contact with his cock, which by that time was aching for release. She was teasing; he knew that. But at the same time, he also knew that in the end he would thank her for it. It was so incredibly erotic to lie here while she kissed him all over his body. Still, it wasn't something that could last; he needed her to finish what she had started. He groaned in both pleasure and dissatisfaction, and she picked up on the signal.

"I think I've been toying with you long enough," she said. "Don't you agree?"

"Oh god yes!"

"All right. I've finished with the appetizers; let's go on to the main course." She lowered her body and positioned herself between his legs. He watched in eager anticipation as she reached out with one of her hands. At the moment she wrapped it around his cock, he gasped in pleasure. She had already done that earlier in the evening, but he hadn't been half as aroused as he was now. The nerves were all on full alert, and the slightest sensation sent electric thrills through him.