Boy in need of Sex Ed

kinkyyoungster

Literotica Guru
Joined
Apr 15, 2006
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517
The School is Johnson Private School. A school with both girls and boys who many have had sexual experiences except one young man. The man's name is Jack and he has never pleased a woman in his life and the reason being is not because he wasn't attractive it was because he was shy and never knew how to please a woman. One day before school was over he was told by a female classmate Clarissa to meet her in the health class on the first floor. Not knowing why he was approached by this he did so anyways wondering why Clarissa one of the most attractive girls in school would want to meet him. Clarissa shows up in the health class right on time as she said she would but with a friend of hers Jack wasn't aware of showing up with. Jack starred at the both of them and takes a gulp of his own saliva wondering what is to happen now.

Jack is "5'7" short brown hair and a nice build all over and shiny green eyes that anyone would get lost in.
 
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OOC: Do you need someone to join you? You should really turn on your private messaging if you're going to be doing rp here..

I would be more than happy to play this role if you like.
 
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Clarissa stood before him in the health room with her friend off to the side. Some would she definately say she did that school uniform alot more justice than it deserved. She walked around almost pacing, her lovely light brown locks spilling down her shoulders.


"Jack is it? It has come to my attention that you have never been with a girl before, is that correct?"


She leaned her face in close to his to look into his almost scared eyes.
 
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Jack takes another gulp of his own fluid as Clarissa moves her face towards his and looks deeply into his eyes. Traying not to get too nervous around this young beautiful woman Jack responds to Clarissa's question.

"N..no I haven't c..Clarissa.."

Jack says out breathing a little heavy for he's never been this close to woman before. Jack turned his look away from Clarissa down to her nice wet pouty lips. They had to be the sexiest lips he has ever seen but dared to not make a move on her.
 
She gave him an almost devilish smirk. She always seemed so sweet to everyone, but now she had this naughty look in her eyes. She got him to sit in a chair and got close to his face again.

"I assume you do know how to kiss right?"

Before he could say another word, she had straddled him on the chair and had pressed her soft sensual lips against his. He tasted better than she thought he would and she wrapped her arms around him pulling him in closer. She could feel him becoming aroused through the soft cloth of his uniform pants. She even began to feel herself get wet through the thin cloth of her underwear as she felt him get harder and harder, deepening the kiss. She just got wetter and wetter and began rubbing herself against the bulge in his pants. She pulled away with an almost hungry gaze.


"Do you like this?"
 
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Jack starred into Clarissa's eyes and nodded his head by the feel of her body on his. He's gotten plenty hard ons in his life but feeling a woman on top of it gave him a feeling far different then having his hand wrapped around it. Whether she had close on or not it still felt good to have such a woman straddle him in the chair.

Feeling her soft lips for the first time made him crave for more and he could tell from the look in her eyes she was hungry for attention. With her lips away from his Jack leans in and kisses her back slowly kissing her soft lips with no tongue just a deep passionate kiss as he moved his hands to her side to hold her in his lap.
 
He kissed her back and devoured her lips his. She had not expected this, and he was a lot better than she thought he would be. His lips felt so good on hers and she wanted even more. No one had kissed her like this. It was spontaneous and not routine like all the other kisses had been. He was different. She began rubbing herself again him again as it provided the sweet friction she craved against her clit. She had not expected to be dry humping him in this classroom, but things were becoming a lot hotter than expected. The need was becoming greater and greater as panties were becoming soaked with her own fluids. She backed off of him panting a bit and slid off the panties from beneath her plaid skirt and kicked them aside. She unzipped his pants and found his length. It was absolutely glorious to her eyes and she ran her tongue across it almost teasing. She realized that this first session was getting a bit out of hand, but she needed some relief. She had not been with a guy in months and it was driving her crazy. She straddled over him and slid down on his length. It felt wonderful as she began to rock wonderfully against him feeling herself become a slave to this feeling.
 
Jack watched as Clarissa backed away breathing heavily from the friction she was giving his hard by dry humping him. He then watched as she removed her soaked panties from her skirt and gazed at them as she kicked them to the side amazed that he made her so wet by just kissing her and letting her dry hump him. He looked back at Clarissa deep in her eyes realizing that he was doing the right thing to pleas her and he loved it.

He saw the same hunger in her eyes as before and he knew that there was no turning back now not that he wanted it to end. This feeling he felt was unbareable he wanted more. Want he wanted he soon got as Clarissa moved her hands to to his pant zipper and undid them quickly. She starres as she sees his hard member fully erect. Unable to take the heat Clarissa runs her tongue over the head of his cock making Jack moan lightly for the new feel of a wet tongue touch his member. Not long does it take to feel the extreme wetness of her pussy as she slides on his shaft causing him to moan a long moan from the feeling he got of her wet pussy.

Jack felt like he was about to cum right there and then but he knew that would ruin the fun so he held himself as Clarissa rocked her hips against him making Jack moan more. He got so turned on by this feeling and being able to smell her sweet sex caused him to moan again before planting a deep kiss on her soft lips once gain.
 
Rocked and bucked against him, moaning greatly and crying out. She pushed against him harder and harder wanting to feel him as much as she could. Her sweet popular girl exterior vanished as was desperately bringing herself to orgasm. He was alot bigger than her last boyfriend had been and she felt so full for once. Rocking harder and harder bringing her closer and closer. Every part of him felt good. Even his lips were making her melt, but she couldn't let him know that. She had to try to remain in charge, even as she felt herself begin to shake. She clamped down on him as she felt herself scream and shudder from her orgasm and she knew his would not be far behind.
 
Feeling her buck harder and harder against him caused him to moan louder. He couldn't believe what was happening right now. He was being fucked by the most popular girl in school and it turned him on so much. He held her tight to his body as she continued to buck. Not too long does her body start to shake as she screams out in an orgasm. Jack felt her pour her juices all over his hard member. Unable to take it anymore he hold her waist tight as he thrusts his hard cock into her sweet wet pussy hard causing her to moan out loud which made Jack dump his load in her pussy.

The feeling of cumming in her sweet pussy made Jack want more but wanting to make it more pleasureable for her he slowly traced his hands over the side of her nice figure as he slowly leaned in and kissed her once again. He couldn't stand from being away from her soft lips they were so soft and wet.
 
She felt so hot as he thrusted into her spewing his seed inside. She clung to him panting and felt him kiss her once more and run a hand down her body. Breaking the kiss she realized they'd made quite the mess. His pants were now probably covered in their juices. She hated to leave him, but it was nearly 4:00 and she had a club meeting. She slowly got off him, his seed still dripping from her slit and slipped her still wet underwear back on. He'd felt so good and she was definitely sure she wanted him as her lover now. She was going to teach him everything she knew and make him better than her sorry ex that couldn't please a girl if his life depended on it. She'd stayed with him because her friends had suggested that it would help her boost her status. She'd absolutely hated him, but stayed until he cheated on her with some slut. Jack was different, he was humble and possibly romantic. She'd actually had a crush on him freshman year, but had been advised not to even think about it. She smiled and gave him a quick kiss.


"I'll see you tomorrow, Jack.. Although I'd love to stay a bit longer, I have certain obligations I need to attend to.. Oh, and don't mention our little rendezvous to anyone. No one will believe you.. Until next time.. "


She walked off almost sensually and met her friend on the outside, then went off to debate team..
 
As Clarissa left Jack sat in the chair still trying wrap his mind what just happened he had to be dreaming. Just to make sure he pinched himself and feltthat it wasn't. Even though it wasn't a dream he still couldn't believe what had just happened. He had just had sex with the hottiest girl on campus...and for his first time. Realizing his private area was still out he quickly snapped back to reality and covered himself up. He was feeling a little flustered from the even that justtook place so he figured he'd do something about it.

Carefully leaving the class room to make sure not to be caught by the any faculty members Jack walked to his room still having the image of what happened in that room. He was never going forgetthis for the rest of his life he thought. He then recalled what Clarissa said before she left

Oh, and don't mention our little rendezvous to anyone. No one will believe you.. Until next time.. "

She was right no one would believe him and it was a little bit of a shame he couldn't tell anyone but then again it made it all more exciting. Wanting to get washed up Jack takes a shower in the boys locker room and heads to his room to start his homework with some complications on keeping his mind focused on the work.
 
She sat in the meeting, still kind of distracted. She was still think about him and how he'd felt inside of her. She thought of how she could arrange their next meeting and what she'd teach him then.. It was a thursday and tomorrow she didn't have anything planned. It would be perfect.


"Clarissa, do you have any objections to trying to get more of a selection for drink machines in the lobby?"


She was slightly startled but answered accordingly.


"No.. I think it's a great idea.. It'll bring in more profits for us to work with."


That was a close one. She walked off to her dorm and began writing a note. She folded it gently and gave it to a friend to give it to a friend to give to his roommate to give to him. Inside it simply read...


Dear Jack,

Need your help studying. Meet me at the library after 4th block.

signed,
Clarissa

P.S.: You won't be needing any books


The whole next day she could think of nothing else but what happened in the health room and she sat at a lone table in the library..
 
Jack paced himself to the library after 4th block like the note Clarisa sent to him had said. He walked in and saw that only a few students were in the library. He looked around looking for Clarisssa til he finally spotted her near sitting at a table near one of the big windows at one of the ends of the library.

He looked over her body as he walked towards her amazed at how beautiful she was today. As he got closer he recapped the events in the health class yesterdayand started to get a hard on already. He tried to walk at his steady pace trying not to hint other students he had a hard except Clarissa for he thought she would just enjoy the reaction her body ws giving him.

As he reaches the table he takes a seat at the right sde of Clarissa but kept a friendly distance between them for not wanting others around to hint at anything.

"It's good to see you again Clarissa. How has your day been?" he asked politely being a gentlmen to her and trying not to make any sudden moves on her to cause suspicions.
 
"It's good to see you again Clarissa. How has your day been?"

She smiled at him and caught a glimpse of his eyes. No wonder she'd crushed on him back then.

"Pretty good actually. We're finally making progress on that economics assignment."

She scooted the chair closer to him and smiled at him again. She then began to whisper softly near his ear.


"Your probably wondering about yesterday.. I honestly had not expected things to go that far that fast, but I do not regret it.. I've asked you here because I'd like to know if you'd be interested in doing more like what happened back in the classroom. I'll show you how to please girl jack.. I'll show you everything.."


She saw his mouth hang open and laughed a bit.


"but seriously.. Are you interested?"
 
Of course Jack was interested. He wouldn't let an oppurtuinity like this slip away. To have the hottest girl in school to teach him how to please a woman was like a dream of his. He collected himself from laughing a little and turned his gaze at Clarissa's. "Of course I would just let me know where and when and I'll be there." he said and continued gazing into Clarissa's nice light blue eyes which he could get lost in for eternity.

Not too long does it take for Jack to get dirty thoughts in his head and his member starts to twitch in his pants. "So what did you have in mind for lesson one?" he asked trying to ignore the bulge in his pants as he waited patiently for an answer from Clarissa.
 
She smirked a little and whispered gently into his..

"To start off, we have to break you of that fear and shyness.. Lesson one will be digital penetration and breaking you of fear."

She could tell he didn't know exactly what digital penetration was so she used blunt terminology.

"You're going fuck me with your fingers... Your challenge is to get me off twice in this library without getting caught and using only your fingers. I will squeeze your hand if you are doing well and pinch it if it is not working.."


She got up and motioned for him to follow her over to the bookcase and sat on the floor with a book, her back facing the bookcase. She removed her outer uniform jacket and placed it on her lap.


"Let's get started.."
 
Having an idea on how to approach this Jack sat down next to Clarissa on her right side and just like her took a book as well. He got as close to her as he could so he could reach his fingers into her slit. Slowly and crafeully Jack moved his left hand over Clarissa's right leg and under her plaid skirt and gently touched the outside of her panties causing her to moan lightly. Jack slowly and carefully rub Clarissa's panties agaisnt her now wet pussy and looked at the nearest end of the book aisle hoping no one would walk by and catch them.

This method of fingering her without getting cought turned Jack on more and more but he carefully continued to rub her outer pussy slowly with a little more pace trying to arouse and not get caught.
 
She began squeezing his hand slightly, showing him that he was doing good, but she knew her body reactions were saying enough. It was torture, not being able to moan out like she wanted, but if she was heard they'd be kicked out.. She felt him slide a finger inside and bit her lip, squeezing his hand harder, trying to look like she was reading.. He was rubbing her in a way that made her question if he had truly been a virgin before the other day. Most guys screwed it up and just jammed their fingers inside and asked if you liked it. Not him, he was rubbing her genly, and the feeling was driving her insane..


"Are you sure you haven't done this before?"
 
After reaching a finger inside her sweet slit Clarissa bit her lip and lightly spoke out.

"Are you sure you haven't done this before?"

Jack looked at her with surprise and responded.

"No I haven't but by that remark I must be doing a good job."

Clarissa said nothing but a light moan as she bit her lower lip to keep her from moaning out as loud as she wanted to. Jack kept his position on the floor next to Clarissa as he fingered her pussy a little faster and rubbing her clit at the same time making her bite her lower lip harder from screaming with such pleasure.
 
His fingers slid in deeper rubbing her to no end. It hadn't even been five minutes and she was already about to cum.. She dug her into his shoulder to muffle her screams as her body shook and she came.. She heard footsteps and quickly got to her feet pretending to read Shakespear's "As you like it"..
He got up beside her and they walked to another area of the library... They went into a downstairs area with older books and she kissed him softly once they were out of sight..


"That was great.."


There was excitement in her eyes and the kiss had not been her teasing. She really was starting to like him again.


"Jack, I'll make you a deal. If you can get me off again in under 5 minutes, I will go on an actual date with you. No hiding, no shame, a real live date. Actual talking, possibly dinner, the whole nine yards. The catch is that I will be standing up right here and you have to be to. You have to keep me from screaming and keep going, even if you think you hear someone coming.. Are you up for it?"
 
Jack could hardly believe what he was hearing. First he engages sexual contact with this beautiful young lady and now she's giving him the offere to go on a date with her and all he had to do was please her again in under 5 minsjust like before. All he had to do was not make her scream and to keep going even if he heard someone. It would be easy to not get caught for it was an old section of the library and he knows no body would wantto look at old books. The screaming part might prove a little difficult but he was up for the challenge.

Taking her offer and planning on doing it right like the first time Jack gently pushes Clarissa against the book shelf and moves against her body. He could feel the heat emitting from her body and made Jack's bulge in his pants twitch. Not wanting to waste his 5 minutes starring at Clarissa's beauty. Steadily but quickly Jack moves his hand up Clarissa's inner right thigh with the top of his fingers closer to her slit. He slowly approaches her slit and moves her panties to the side and slowly enters two fingers instead of one this time and startto slowly finger fuck her still wet slit.

Clarrisa starts to moan lightly by the way Jack was working her pussy like no other man has slowly and passionatly like his kisses. As he works a little faster she start to moan louder but Jack got an idea so no one could hear her. Quickly but gently he places his lips on hers and kisses her passionatly as she moans in his mouth. As he gets a rhythm going fingering her pussy he starts to use his thumb and rubs her clit slowly like before.
 
She felt two fingers enter in this time and she cried out. Gently sliding in and rubbing her insides. He began to pick up the pace and she could not hold back her moans and soft sighs. As she got louder he muffled this sound by kissing her deeply. He rubbed her clit in addition to his other ministrations and she wrapped her arms around his neck as she kissed him back. Her kiss became wild and devouring and neared the edge and plunged in orgasm.. Her body shuddered once again and she clung to him feeling quite weak from it. This had not been what she expected. She had expected him to be shy and easily controlled. This was not the case. He was different. She actually wanted to get to know him. Even though she'd been hurt many times in the past, she was willing to take that chance. She looked him in the eyes and had a different look on her face. For that moment she wasn't the most popular girl in school anymore, she was just a girl.



"So when do you want to have that date? I'm pretty free tonight.."
 
Feeling that he succeeded in winning a date with the wonderful Clarissa put a smile on Jack's face. After she rivered her juices on his hand he looked at her and smiles as he saw something different in her eyes this time around it was not of hunger but of some sort of innocence. He looked over deeply in hers as a warming feeling in his body took over not of lust for her but of deep feelings one would have over a loved one. He wasn't close to saying he loved her but he found a new feeling towards her and he liked it.

He couldn't quite put his finger on what he saw in her eyes but he didn't mind it. Feeling the warmth of just being in her presence caused Jack to smile a warm welcoming smile to her which caused her to smile back. As for the date Jack didn't give it too much thought for all he really wanted to was to get to know her better. "How about we just go out for a small bite to eat and get to know eachother better?" Jack asked to see if Clarissa was up for chatting for the night when he felt a warm sticky substance on his hand.

Getting caught in her eyes made Jack forget he still had her fluids on his hand and fingers. He then raises his hand and says as a joke. "I think we should clean up first." he said with a light nervous laugh still trying to get used to being around her and not knowing what to and not to say for he never really got to know her personally and he was hoping that he could get the chance to.
 
They both retreated to the bathrooms and she came back when she was done cleaning herself up a bit. They decided to go back to the dorms and change then meet at a lamp post. She picked out a tank top and a pair of jeans. She put on a simple hoodie over that and walked out to meet him.


"Hi.."


She looked like a normal girl and kind of shy..
 
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