Comforting Tutor

[musicankane]

Jake smiled and leaned closer to her, "I'd kiss you until the end of the world." He whispered and kissed her, trying to do just what she had said and be more aggressive. Though not really aggressive just a bit more forward. Why would he need to calm down, he felt fine and the feel of her lips against his was the most incredible thing ever. His hands came up of their own accord and pressed against her sides, holding her. His thumbs gently stroked her side, and it took everything in his power to not slip his hands up to touch her breasts. He kept having to tell himself that she was doing him a favor, and he shouldn't dare to take advantage of it by pushing it further than she let him.

 

[w0ndergirl4]

Jake was definitely a fast learner, Sarah thought as she felt the teenage boy push his tongue back into her mouth. That was a good thing. Not that he was ready to be unleashed on the female population of the high school after just a few kisses, but he was making progress. The fact that his hands were creeping slowly up either side of her body was testament to his new found willingness to be more aggressive. In fact, if he got any more aggressive, he'd be copping a feel, she realized.

After a few moments, Sarah leaned back, breaking the kiss. This time as she pulled away, she couldn't help but glance down at Jake's lap. The erection in his pants seemed to have grown even larger.

"Alright, Tiger," she said as she took hold of his wrists and pushed them away from her body, smiling to let him know that she wasn't angry at him. "Before we do anymore practicing, I need to know something. Have you, well, have you ever had an...an orgasm?"

 

[musicankane]

Jake blinked, surprised at her question. What teenage boy hadn't jerked off before. Sure he knew he came across as a goofy shy guy, but surely she couldn't think that he had never even touched himself. He knew his dick up and down, so he nodded, "If you are asking me if I masturbate then yes of course I do. I'm not that hopeless Sarah, I have the internet in my room and porn is a wonderful thing. It's more real life expereince that I am hopelessly without." He told her chuckled softly.

He shifted in his seat and adjusted himself in his pants. "I guess it wasn't a good thing for me to get all hard on you huh?"

 

[w0ndergirl4]

"It's okay," Sarah said with a giggle. "I just wanted to make sure you weren't going to cream in your pants while we were making out. Not that you would be the first guy to do that while I was kissing him."

Sarah stood up and walked over to the desk to get a drink of water before turning back to face Jake who was still sitting on the bed. The bruises on his face and the swollen lip reminded her just how rough Jake's life had been lately, and she found herself wanting to do something to make him happy, something more than just letting him kiss her a few times.

Stepping back over to where he sat, Sarah looked down at Jake, "Well, since you're such an expert, what with all of your internet porn experience and all, we should probably move on to the next lesson." With that, the blonde reached down and lifted her tank top up over her head and tossed it down on the bed. Without hesitating, Sarah reached behind her and unsnapped her bra, then let it slip off her shoulders and arms, falling to the floor.

Sarah stood in front of Jake, her breasts bared to him, hoping she really could trust him not to tell anyone about what they were doing together. Her breasts weren't big, but they were big enough, and they were perfectly shaped, her skin smooth and devoid of any tan lines. "Have you ever touched a girl's breasts?"

 

[musicankane]

Jake watched her carefully as she came back toward him. He smiled up at her, just because he was nervous. Then before he could react she pulled her top up over her head and tossed it to the side. His eyes went wide as he looked at her incredible midsection. Then without even much of a pause she popped open her bra and let it drop.

Jake was seeing breasts, real and up close for the first time in his life. Sarah's breasts were amazing, perky, firm, beautiful nipples, just all around mouth watering melons. He looked at her in shock and she asked him if he had ever touched a woman before.

HE could only shake his head and say, "Wow." Then he swallowed quickly before the drool fell out of his mouth.

 

[w0ndergirl4]

"I'm going to take that as a 'no'," Sarah said with a soft laugh as she eased herself back down onto the bed next to Jake. "Well, each girl is different. Some will like having their breasts played with, and others won't so you'll have to learn to listen for clues."

Reaching down, Sarah took hold of one of Jake's hands and lifted it up to her left breast. She hesitated for a moment, his hand just inches from her chest, "It's a good idea to start out a gentle until you know what she likes, and remember, the nipple is usually the most sensitive area for any woman."

Without another word, Sarah placed Jake's hand on her bare breast and waited to see what he would do next.

 

[musicankane]

Her breast was extremely soft, and warm. His hand felt wonderful in his palm, the soft weight of her mound in his cupped hand was something he never thought he would get to experience. He was frozen at first, his eyes just staring at his hand on her breast. Then he licked his lips and flicked his thumb over her nipple. The soft nub gave way to his thumb with each passing stroke.

He lifted his hand, forcing her breast to move up. Jake couldn't help the smirk on his face. He squeezed his hand gently and began to gently stroke her breast, sliding his hand along the underside of her breast rubbing her smooth soft skin. God she was perfect, this girl. Everything about her was flawless.

 

[w0ndergirl4]

Sarah waited patiently as Jake worked up the courage to finally start moving his hand against her breast. She knew this was probably a little overwhelming for him, but she also knew that he was an eighteen year old boy who'd never touched a naked girl before, which meant sooner or later his desire was going to overwhelm his fear. Sure enough, after a couple of moments he began to stroke her nipple with his thumb.

The blonde's nipple was already partially hard, but once she felt Jake begin to rub it with his thumb it quickly grew completely stiff. It had been a couple of months since Sarah had been with anyone, so even though she wasn't really attracted to Jake, she was beginning to get slightly aroused.

"You're doing good," she said with a smile. "You can use your other hand now too."

 

[musicankane]

Jake felt her breathing change, as if she were enjoying his touch. Her body arched against him and pressed herself tighter to her palm. She told him to use his other hand and he did, immediately bringing up his hand to cup her other breast. He found his hands working together, moving her breasts in sync. He noticed that she liked it when his thumbs flicked over her nipples, so he focused on making sure he did that.

He licked his lips and realized his mouth was watering. He smiled softly and said, "This is insane. I can't believe how awesome this is." He shifted in his seat a bit, as his cock throbbed painfully against his pants, the zipper was now digging into his skin and pinching a little.

 

[w0ndergirl4]

It's kind of working for me too, Sarah thought as she felt Jake focus his attention on her nipples. Better than I ever thought it would, she admitted to herself as she realized that she was getting a little wet from having her tits fondled.

"You can press a little harder if you want to," she said, trying to sound non-committal about it. Even as she said it though, Sarah noticed Jake shifting slightly as if he was in an uncomfortable position. She realized it was probably due to the serious boner in his pants.

"Everything okay?" she asked, wondering if maybe she should put a stop to this before she left him with a painful case of blue balls.

 

[musicankane]

Jake paused what he was doing and looked at her. He didn't realize she had asked him a question at first, but then he frowned and nodded. "Yeah my pants are a little tight, and now that I am....excited. My zipper is digging into me." He took his hands from her breasts and reached down to try and adjust himself. Nothing worked though.

He stood up and tried to tug his pants higher but it only made the zipper grind on him more. "Do you think I could just unzip a bit, it hurts?" He asked her only pleading slightly.

 

[w0ndergirl4]

Wow, there cowboy, Sarah thought as she heard Jake ask if he could unzip his pants. She was starting to wonder just how far this little instructional lesson was going to go, how far she was willing to let it go. She didn't want him to be in pain, and she didn't want him to cum in his pants, but she was afraid if she let him unzip his pants he might start to get the wrong idea about where this was heading.

"I guess if you're wearing underwear, it would be okay, I mean, I don't want you to hurt yourself, but...you can't take it out, okay?" she agreed, still not quite believing she had let things go so far. It was one thing to feel bad for Jake, but another to let him feel her up and then start taking his clothes off.

 

[musicankane]

Jake let out a sigh of relief as she gave him permission. He was wearing underwear and it should be okay to just get rid of the zipper. "Thanks." He told her and popped open his fly. His pants fell to the floor and left him in only his boxers, but more importantly than that was the massive tent in his boxer shorts now. It tented his shorts so much that if she looked down his waist band she would see all of him.

He blushed and casually rubbed himself, "Sorry about this." He said, feeling uncomfortable and stupid standing in front of her with just his boxers on. "Maybe we better not..." He said bending down to grab his pants again.

 

[w0ndergirl4]

Sarah was caught off guard slightly when Jake's pants fell to the floor revealing the rather large erection in his underwear which were pushed straight out away from his body, straight out toward her. She couldn't help but think that Jake was significantly more well endowed than she'd imagined, judging by the size of the bulge there.

"Maybe we better not..." He said bending down to grab his pants again.

"Jake, it's okay. You don't have to be embarrassed," Sarah said, reaching out to take his hand and pull him back down onto the bed. "It's okay that you're getting hard, to be honest, I'd be offended if you weren't."

"Now, do you have any questions for me about breasts or nipples or, well, anything?" she asked releasing his hand as she sat in front of him topless.

 

[musicankane]

Jake sat down which made his dick bob in his shorts and turned to her. She was being so cool about all this. Though he felt better when she told him he should be hard. In a way in made sense right? She was a girl and what they were doing was basically a wierd foreplay. Foreplay was to get ready for sex and part of getting ready for sex was him having a hard on.

He looked at her and gently reached over to caress her breast. His fingers trailed across her hard nipple. "Your nipples are hard too. Does that mean I turned you on too?" He asked her, wondering he had the same effect on her as she did on him.

He smirked, "Man I am going to have to jerk off so hard when i get home."

 

[w0ndergirl4]

With Jake once again sitting next to her on the bed, and his hands once again moving to her breasts, Sarah found her attention fixated on the seemingly massive erection in his boxers. She was sure Jake was bigger than her last boyfriend, maybe bigger than any man she'd been with. Okay, focus on something else, she told herself, and remember this is Jake we're talking about.

"Well, it's true that most girl's nipples get hard when they are aroused, but don't assume just because they are hard that that's the reason," Sarah responded as she let the awkward teenage boy continue to explore her chest with his hands and eyes. "My nipples are really sensitive so they get hard a lot, especially if I'm cold."

"Man I am going to have to jerk off so hard when i get home," she heard Jake say under his breath.

"Don't forget, we still have some studying to do before you go," Sarah pointed out with a smile. Even as she said it, the blond couldn't help but wonder whether Jake would be able to focus on school work after getting so turned on. She knew she wouldn't if it was her, not until she'd had a chance for a little release...

"Maybe we should stop," Sarah said, realizing that things had already gone much further than she had ever intended and were dangerously close to spiraling out of control. But then again, was it really fair of her to get Jake this worked up then expect him to just shut down and focus on teaching her trigonometry or history?

"Unless...well, maybe you could just do it here," Sarah suggested. "Jack off, I mean."

 

[musicankane]

Jake gasped at her. There was no way she could be serious, how could even do it here? He couldn't just jerk himself out of his shorts and start stroking with her watching. Unless she left the room, but if she did that he would need something to look at, at least a picture. Though if she stayed he could look at her tits, but then she would be watching him.

Talk about awkward, hell even if he tried it would feel wierd. What would Sarah being doing, sitting patiently waiting for him to cum? He could imagine her sitting her with a bored look on her face waiting for him to hurry it up or something.

He chuckled because he had no other idea how to respond to that, "Jerk it here? Yeah right Sarah. Look this has been the greatest day of my life, thank you so much. I mean I never thought something like this would happen to me. But to just start wanking it right in front of you...I don't know if I could do that."

His hand absently went to his member and kind of rubbed himself through his boxers without realizing it. The primal part of him really just wanted to fuck the shit out of Sarah. They were pretty much halfway there. Hell if he whipped his dick out all she would need to do would be sit on him, or lay back and let him simply slide inside. He shivered lightly at the thought and then chased it away, that was too far.

 

[w0ndergirl4]

"Look this has been the greatest day of my life, thank you so much. I mean I never thought something like this would happen to me. But to just start wanking it right in front of you...I don't know if I could do that," Jake said, clearly embarrassed by the thought.

Sarah started to object and explain that what she was suggesting was that he slip into the bathroom and take care of things in there. She certainly wasn't suggesting that he do it right in front of her while she watched. That would be completely weird. But, as she thought about it, she realized that there was another option, but could she actually do it?

"Would it help if I, well, if I touched it?" the blonde asked, her gaze once again moving down to the prominent tent in his boxers. "Why don't you take it out and let me see it. If you're too embarrassed to let a girl see you naked then you'll never be able to be intimate with someone. Go ahead, no reason to start getting shy now."

 

[musicankane]

Jake had his mouth open to say something but when she told him to let her touch it, he shut it quickly. This was insane, but it was like he stepped not into Sarah's room but instead paradise. He swallowed and waited for her to start laughing or move away or something, but she simply waited for him to make a move.

He looked down at himself and then back up at her slowly, "Are you sure?" He asked. She was right though, he could never be a man if he never wanted a girl to see his dick. That was part of it after all, if he was going to have sex, then eventually the girl he was having sex with would see his penis.

He stood and took a deep breath, "Okay Sarah, but you have to promise not to laugh or anything." He told her, then slipped his fingers to his waistband. "Here goes nothing." Then like ripping off a bandaid he jerked his boxers down.

When he stood up straight his cock was hard and bobbing in front of him. It definately seemed to know that she was there and it was like his cock pointed right at her face. He turned bright red and waited to see what she would say to him.

 

[w0ndergirl4]

As Jake stood up, Sarah actually found herself getting a bit nervous. Part of it was that she was afraid she might be letting things get out of hand, and that either Jake would start to get the wrong idea or that he might tell someone about what they were doing together. But that wasn't the only reason her chest felt tight and her stomach was flip-flopping. There was also a certain tension coming from the fact that she wanted to see Jake's cock. It was silly, really. She wasn't attracted to him, but at the same time, it was hard not to be curious about what was in his pants, especially after seeing the extremely prominent bulge in his pants.

And then it was there, pointing straight out at her, in all of it's massive, magnificent glory, Jake standing in front of her, his underwear on the floor around his ankles. Sarah didn't say anything at first, as she sat up a little straighter, her eyes following Jake's manhood as it bounced slightly in front of her. It was definitely bigger than any she'd seen before, except maybe in a dirty movie.

"Okay, well...one thing's for sure, you don't have to worry about disappointing any woman you're with, scaring her maybe, but definitely not disappointing her," Sarah said with a smile.

"It's big and that's a good thing, trust me," she added. "And you obviously don't have any trouble getting hard, so that's good too."

"Why don't you go ahead and sit back down?" Sarah suggested as she patted a spot on the bed next to her.

 

[musicankane]

Jake felt a whole lot better by the way she reacted to his cock. He was nervous of course, the first time a girl was seeing his penis and not only seeing it but seeing it hard and ready for action so to speak, he couldn't be more nervous. What if he was too small? Too big? Too thin? Too wide? Curved in a weird way? There were so many things that could make his penis a freaky or useless penis. But she reacted in only a favorable way. She praised him, well not exactly praised him but at least gave him encouragement and assurance that his dick was a good dick.

He let out a breath of relief and sat down beside her again. His eyes wondered down to look at her breasts and he really wanted to touch them. But more than that, now he wanted to touch her with his dick. He was out and naked for her now, he wanted to feel her skin along his shaft. He wanted to feel to touch of someone else on his manhood rather than himself.

This seemed to be going over some kind of line, but it seemed silly to be naked with Sarah and sitting here only to not have her even touch him. Something about it felt like now that the taboo or resistance line had been crossed there was no reason to stop now. Hell she might even suck his dick or even better let him put his dick inside of her. Now wouldn't that be something incredible. He was so close to possibly losing his virginity he could hardly fight the shakes.

 

[w0ndergirl4]

"Okay, I'm just going to reach out and touch it now," Sarah said as she lifted her hand off her lap and extended it in Jake's direction. "If you want me to stop, or anything I do makes you uncomfortable, all you have to do is say so, and I'll stop, okay?"

Sarah tentatively let her fingertips glide along the top of Jake's massive boner, her thumb curling underneath it, forming a ring around the girth of it. She scooted a few inches closer to him so that she could reach the base of his cock. As she began to very slowly stroke down to the base, his curly pubic hair tickling against her hand, then back up to the swollen head, Sarah looked up at Jake, to gauge his reaction.

"You okay?" she asked. "Make sure you tell me if you think you're going to cum, okay?"

 

[musicankane]

He wasnt uncomfortable, nervous yes but not uncomfortable. He watched her hand wrap around him and held his breath at her touch. He expected it to be suddenly just insanely amazing. Then as she started to stroke him he realized that it felt almost the same as when he did it. Different though, she didnt move like him, didnt stroke the same way. It felt good but it was more because it was different to have someone else stroking him.

He nodded when she told him to warn her when he was cumming. He felt stupid just sitting there letting her stroke him. So he moved his hand back up to cup her breasts again. He trailed his fingers over her soft skin, feeling her and taking advantage of being allowed to touch her.

 

[w0ndergirl4]

Sarah almost stopped stroking Jake's cock when she felt him reach out and start to fondle her breasts again. She'd already let him play with her bare breasts, so what was the big deal, right? Of course, the first time she hadn't been jerking him off while he did it. Pushing the awkward thoughts to the side, the blond focused on increasing the speed that her hand was moving, gripping just a little more firmly than before. She was sure that she could feel Jake's penis getting even harder and thicker in her hand.

"Okay, now you're gonna want to try to hold out for as long as you can," Sarah explained as she looked up at Jake's face. "You don't want to be one of those guys who cums really fast before the girl even has a chance to get going."

"I'm gonna touch your balls with my other hand," she warned him before reaching over with her other hand and sliding it beneath his sack to cup his testicles. "Some guys really like that, but if you don't just let me know."

 

[musicankane]

Apparently Jake wasnt going to be one of those guys who didnt like to have his balls touched. He let out a gasp as her hand cupped him and suddenly the name of the game changed. Her strokes and caresses of his balls made him ripple with pleasure. He was forced to drop his hand from her breast and catch himself as he leaned back on the bed a bit.

"Oh my god that feels amazing." He panted, his eyes watched her stroke him. Though he made sure to watch her breasts jiggle and sway as she worked on him. "Fuck you are so beautiful Sarah." He breathed. "I would do anything to be with you." He confessed.