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.
She winked, then opened her mouth and stuck out her tongue. When she touched the tip very lightly against the head of his cock, he thought he was going to die from pleasure. But somehow, amazingly, that wasn't the maximum of what he was capable of feeling. It was even better when she began to run her tongue all over the head. There was a small spot on the underside that she paid particular attention to, sending almost overwhelming waves of pleasure through him as she teased it with her tongue. It was like the focal point of all the nerves in his body.
He groaned as she stimulated him, somehow keeping it to a whisper, though admittedly a loud one. She smiled as she heard the sounds coming from his mouth; she was enjoying doing this to him.
Then she sucked it in between her lips, and he gasped. At first she took only the head in, and he didn't need to see the compression in her cheeks to know that she was sucking it. The reverse-pressure was an even more intense feeling than the tip of her tongue had been. He began to shudder as the pleasure overtook him.
Even inside her mouth her tongue continued to work it, rolling over and under it as she sucked.
Then, still sucking, she lowered her head and let him slide further into her mouth. Jeff was in heaven. This was the most exquisite feeling in the whole world.
But she wasn't done yet. She lowered further still, and he wondered just how far she was willing to go. He could feel himself at the back of her throat now; there was nowhere to go but down.
That was exactly where she was aiming. He felt himself actually sliding right into her throat as she managed to take his whole length in.
"Oh my god!" he gasped. "I don't believe it!"
She pulled out until she had only about half in her mouth, and laughed around it, no doubt amused by his na�vet�. Then she began to move her head up and down, sucking and licking all the while.
His hips began to get into the motion, so she wrapped her hand once more around his cock to help control how deep it went. She bobbed up and down on it, driving him wild with ecstasy. He lay his head back and closed his eyes, blocking out all external stimuli except the feel of her mouth around his cock.
She was moving quickly now, almost violently. It was with only the greatest self-control that he kept himself from grabbing her head and spearing her throat with his dick; she certainly wouldn't appreciate that!
Then he felt something happening. The pleasure, already beyond anything he had ever experienced before, began to climb to new heights. It was like a pressure building in him, nearing a boiling point. In a few seconds he was going to explode.
"Oh god oh god oh god oh god!" he began to moan as it intensified. The world was spinning around him; he couldn't think straight. All he knew was that he was about to experience something he had never felt before.
When it hit, he shook with ecstasy. He felt his cock throbbing wildly, and felt something shooting out of it. He was having an orgasm! His first orgasm, in Rachael's willing mouth. She showed him no mercy, but continued sucking as hard as she could as she swallowed everything he gave her.
Somehow he survived the extreme pleasure, the overloading of his senses that he had never even thought possible before. His dick stopped pulsing and the pleasure waned. He found himself lying in his bed literally gasping for breath as Rachael let his softening member slip from his mouth. She licked her lips as she stared up at him with a grin.
"So how was your first orgasm?" she asked.
"My god!" he exclaimed. "That was amazing! I never knew it could feel that good."
"It gets even better," Rachael said, moving up his body. "But you're probably not up to it at the moment."
"Probably not," he replied. "I'm exhausted."
She lay her head down on his chest. Her body against his felt so wonderful, so peaceful and relaxing. Instinctively he wrapped his arm around her.
"Why don't you get some sleep?" she suggested.
"Thanks. I am pretty tired. It's nice to have you here with me."
"I'll wake you in a couple of hours after you've had time to recuperate, and we'll make it official."
"Official?"
"Yes," she grinned. "You haven't had your cock inside a girl's pussy yet, so depending on your definition, you're still technically a virgin."
He laughed. "I guess I am. Just make sure it doesn't stay that way."
"Don't worry; it won't."
Jeff closed his eyes, thrilled at the thought of what she was going to do to him and at the same time, content to just lie here snuggling with her. Her body felt so soft and warm that he almost felt like he could just lie here with her and forget about the sex.
With that wonderful thought, he drifted off to sleep.
Later that night he dreamt that he was lying there immobile while a beautiful woman kissed him all over his face, neck, and chest. He was more than a little aroused, and she kept staring down at his crotch to check on his progress. All in all, it was a wonderful fantasy.
Five minutes later he realized that it wasn't a fantasy, but reality. He had been half awake the whole time, and as full consciousness took him, he recognized the beautiful woman as his aunt Rachael. He slipped his arms around her waist.
"Good morning, sleepyhead," she grinned.
"Is it morning all ready?"
"About four o'clock. A good time for sex."
"I've never heard that before. Four o'clock in the morning is a good time for sex?"
"Of course. Any time is a good time for sex."
He laughed. "Okay, I'll grant you that."
"So judging by your little guy down there," she said, nodding toward his erect member, "it looks like you're ready."
"He's not so little," Jeff complained playfully.
"No he isn't," Rachael conceded. "Okay, your big guy down there."
"Much better."
She rolled onto her back. "But if we're going to do this right, you're going to have to loosen me up a little."
"Loosen you up?"
"Stimulate me."
"Stimulate you?"
Rachael laughed. "You really aren't experienced, are you?" she asked.
"I don't think that's in any doubt."
"All right. I'll guide you. You can start by kissing me."
"That much I can do," he grinned. He leaned over and pressed his lips against hers. She closed her eyes and let it happen. A little boldly, he slipped his tongue between her lips, and she accepted it eagerly.
The kiss was absolutely wonderful, and he wanted it to last as long as possible. In the end, it was Rachael who pulled away. "I can't believe it," she said.
"What?" he asked, worried that he had done something wrong.
"I'm never the one to break the kiss," she laughed. "It's usually the other person who has to come up for air first."
"I cheated," he grinned. "I breathed through my nose."
She grabbed his head and kissed him again, but this time it was a short one. "Now kiss my neck," she said.
"Yes Mistress," he teased.
"Ooh, I like that! Maybe we can play that game next time. Right now is more a learning experience."
Jeff lowered his head to her neck. As she had done to him, he stuck out his tongue and flicked it against her skin, and she jumped as a chill ran through her body.
"Who taught you that trick?" she asked.
"You did, don't you remember?"
"Oh yeah. Do it again."
He did.
She shuddered in delight as he teased her like that. His licks turned to kisses, which he spread all over her neck. He could hear her breathing growing heavier, and he watched with arousal as her chest rose and fell as she breathed in deeply. Her breasts gave a delightful little jiggle with each movement, which he found very sexy.
"You're staring," she told him.
"Oh, sorry," he said.
"Don't be sorry. I like it. But I'd like it more if you did more than stare."
"What do you want me to do?"
"I want you to touch them."
"Okay!" he grinned enthusiastically, reaching out with his hand. He didn't hesitate, but began to run it all over her breast. She closed her eyes and sighed in pleasure. He took that as a good sign, and began to squeeze and rub it, gently at first but gradually more and more firmly. His fingers went to her nipple, and he ran his fingertip around the outside of the areola. He knew that he was sensitive there, and supposedly girls were even more sensitive, so he wanted to see what her reaction would be.
She sucked in her breath in a loud gasp, which thrust her chest out even more. That meant she was really enjoying it. He continued to trace around it for about thirty more seconds, then pinched her nipple gently between his thumb and forefinger.
"Oh god," she whispered, and he grinned. It was fun to give her pleasure like this.
But the other breast wasn't receiving any attention. He knew what he wanted to do with this one. Instead of touching it with his hand, he leaned down and flicked his tongue against the nipple. The sudden pleasure along with being caught off her guard like that caused her to give out a brief but loud squeal. They both suddenly froze, and Rachael put a hand to her mouth in embarrassment. They lay there immobile for about ten seconds as they listened for any sign that Brit had awakened in the next room. Only after they were sure that she was still asleep did they dare even start breathing again.
"Sorry, Jeff," said Rachael with a nervous giggle.
"It's my fault," he told her. "I shouldn't have licked you like that."
"No, that's exactly what you should have done," she grinned. "In fact, I want you to do it again. I promise I won't shout this time."
"Okay." He lowered himself again and began to tease her nipple with his tongue. Her reaction this time was more subdued. She merely gasped and shuddered with the pleasure of the contact.
He was enjoying this as much as she was. It felt good to be doing this to her, to be causing her body to react in this way. There was a bit of pride there; here he was, an ordinary fourteen-year-old boy, and he was giving pleasure to a nineteen-year-old girl.
"Jeff," she said. "Put your hand between my legs."
He did as instructed, sliding his hand down her abdomen to her pussy. She spread her knees to offer him better access, then put her hand on his and began to guide it in gentle strokes. He felt moisture down there; he had heard that when women got aroused they got wet like that, just like men got hard.
"Do you feel that there?" Rachael asked, placing his fingertips against the top. He felt a little bump. "That's my clitoris," she told him. "It's just as sensitive to me as your dick is to you. So make sure you don't neglect it."
He ran his fingers around it, feeling it growing and opening up for him. She returned to her quiet moaning and heavy breathing as he stimulated it with his fingers. His mouth went back to her nipple, and this time he sucked it in between his lips.
The rest of her pussy was opening up as well. Experimentally, he slid a finger inside.
"Oh god, Jeff, that's good!" Rachael groaned. "Just like that."
He ran his fingers around and inside, feeling her opening up more and more for him. Her body was starting to move now, her hips rocking forward to spear herself on his fingers.
"It's time," she told him. "I want to take your virginity now." She spread her legs even wider than they were already, and he stared down at the beautiful, inviting, pink opening.
He rolled over on top of her, positioning his hips slightly above hers. She grasped his member and placed it against her entrance.
"Now slowly stick it in," she said.
Jeff lowered his hips, gasping at the wonderful feeling of her pussy surrounding the tip of his cock. As he pressed further, he felt the warm softness enveloping him, caressing him.
Finally, he was all the way in, and he was lying completely on top of her.
"Do you like that?" she asked.
"Oh yeah," he replied.
"Then what are you waiting for? Fuck me."
He drew back, then plunged in again. Her own body rose up to meet him. The smile of intense pleasure on her face was enough encouragement. He began to rock back and forth, penetrating deep inside her. He started slowly at first, then gradually built up the tempo.
She wrapped her legs around him and held him there as if forcing him ever deeper inside her. He continued to slam her with his cock, and she bucked underneath him.
They kissed each other passionately, wildly, insanely. It was the most wonderful feeling to lose himself in the lust and just go crazy with her. Somehow they managed to keep one tiny inhibition; rather than scream out like they wanted to, they kept it silent, with only the occasional gasp as momentary spikes in the pleasure shot through them.
He had thought that her mouth had felt exquisite around his cock, but it was nothing compared to her tight little pussy squeezing it and the rest of her body against his. Just like she said, it had been more intense with her mouth, but to not only have the stimulation on his cock, but also to feel her breasts and to be face to face with her supreme beauty was the most amazing feeling in the world.
She began to take charge, controlling the tempo and writhing her hips against his. He was more than happy to let her lead; she was the more experienced of the two after all, and therefore knew what to do better than he did.
He didn't know how long it lasted; the world had disappeared as well as all sense of time. There was nothing but Jeff, Rachael, and the boiling hot passion between them. But that passion wasn't constant; on the contrary, it intensified with every second that passed. He could feel the pleasure building again just like it had with her mouth, and knew that he would reach the ultimate goal soon.
Rachael hit it first. She gritted her teeth and shut her eyes tightly as her body tensed up. He could feel the walls of her pussy tighten, squeezing his cock as she shook with orgasm. He had done it! He had given this girl the ultimate pleasure!
That thought was enough to push him over the peak as well. He slammed into her one last time and released, feeling his cock pulsing inside of her. He gasped with each spasm as he emptied himself deep within her body.
The climax itself lasted for what seemed like forever, but he knew it could only have been a few seconds. Then the pleasure began to fade, leaving him tired and spent. He collapsed on top of Rachael, too weak to move.
"Roll over onto your back," she whispered.
"What?" he asked.
"Roll over onto your back. You may be younger and just a little smaller than me, but you're still pretty heavy."
"Oh, sorry."
She laughed as he rolled off of her. She took her previous position at his side, with her warm body pressing against his and her head on his chest. He put his arm around her.
"Congratulations," she said. "You're no longer a virgin. And by the way, you're the best fuck I've had in a long time."
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 United States License.