Chapter 1: First time

The sensation was overwhelming as his cock entered a pussy for the very first time. Delightful flashes of tingles that coursed through his body, his attention focused on the warm wet feeling of her lips surrounding his cock. Her lips gave way slowly, a gentle thrust separating them, the moisture leaking as they parted giving him entrance. The warm sheath lubricating the tip of his cock, dragging up the skin, pulling on it gently, felt unlike anything he had ever felt. Reversing, his cock pulling on the lips, gathering more of her moisture, the lips extending slightly, lubricating more of his cock for the return slide back into her. She had a frown of concentration, a distant inward gaze as she concentrated on feeling the fullness she had never felt before, the slight pressure as the dull head of his engorged cock pressed against her hymen. The feeling he felt as he hit the hymen, an encompassing softness and increased pressure surrounding the head of his hardness, the back pressure on the head of his cock as the hymen bowed inwards under his slow but relentless attack created intense sensation that flowed from his cock to all reaches of his body. He hesitated, reared up on his arms and looked down at her, a quizzical look on his face.

"I'm ready... Go ahead."

He pressed forward slowly. She felt the burning sharp pain of the hymen slowly tearing.

"Do it... do it quickly, please."

He thrust forward sharply and was rewarded with the feeling of being fully one with this woman, as she grunted with the sharp burst of pain in her loins. He held still, deep within her, whispering in her ear... "are you ok? Did I hurt you?"

Her breathing was fast and shallow as she felt her inner walls absorbing his shaft. The sharp pain dulling to an ache, but being slowly overcome by a heavenly feeling of fullness, the tingles from his pubic bone pressing against her clit increasing as his body moved subtly with each of his deep breaths.

He could feel her entire body beneath him, her legs spread wide to accept him, her nipples, hard, pressing against his chest, her flat stomach against his, her sparse pubic hair blending with his. She held him with her arms wrapped tightly around his neck, her body feeling his vibrations as he struggled to remain still.

"Its ok... I'm fine."

John's hips pulled back slowly, his gaze still concentrated on her face, looking for any signs of pain, he stopped again with the head of his cock placed just in the entrance of her pussy, watching the slight grimace as the crown of his cock crossed the plain where her hymen had so recently been attached. The struggle to remain still was the hardest battle he had ever engaged as the sensations of his cock sliding so freely in the tight, warm and wet sheath that her pussy provided. The desire to slide in again was almost impossible to fight. His balls pulled up tightly to his body, his cock amazingly hard in its efforts to spew his seed inside this wonderful refuge.

"uhh! Ohh... You feel so good Libby... so very good..." and he let his hips fall, feeling the most amazing sensation of his 18 year old life. The gentle tugging of the skin over the entire surface of his cock, wonderfully lubricated, was so far ahead of the sensation he got when he stroked his own cock in his masturbatory efforts. His body was focused on the feelings emanating from his cock, his legs twitching in response to the bursts of pleasure coursing through his body, every muscle taut, still trying to overcome the instinct to repeatedly plunge his cock into her, fast, hard and repetitively.

"John... Fuck me... please..." Libby's breathing was still labored and she still felt the slight burning pain when the crown of his cock passed over her most tender area. While the pleasure was building the slight pain kept it from becoming the level of pleasure that signaled her orgasm. John thrust harder into her, gaining slightly more depth, forcing air out of her almost explosively. John felt the onset of the rush of sensation, the absolute tightening of his balls, the tense vibration of every muscle as he thrust into Libby again and again, her moaning had taken on a different timbre.

"shit... Libby... I uh... I'm going... going to... I can't stop... it..." Libby wrapped her legs around John and pulled him close to her as he thrust deep inside her. She could feel his cock grow slightly and felt as John's body burst with each shot deep within her depths. John pulled back and thrust deeply into her again and Libby felt a deep sensation as the crown of his cock rubbed her G spot followed almost instantly by a shower of sparks as his pubic bone pressed against her clit, the friction more intense as his body twitched with each orgasmic flutter.

The feelings that John was feeling were almost indescribable. The rush as his cum raced up the hard shaft of his cock, the warmth as he was fully encased in her pussy, the slight fluttering as he held his cock deep within her, his cum bursting forth from his cock, he felt as if his entire being was deposited through his cock deeply into his girlfriend. The current of pleasure that flowed through his body built him up to a tenseness unlike anything he had ever felt. The aftermath was the feeling one gets after a good massage, the relaxation, the warm glow that flowed through his body, completely at peace.

As he caught his breath again he rose up on his arms and looked down at Libby, the level of emotion was deeper than anything he had ever felt. He never would've imagined over the years that he would ever be in this position. His past with Libby was long and checkered.

John had always had a crush on Libby, since he met her on the first day of high school. He enjoyed talking to her at the parties, on the phone like they had over the years. Then as graduation approached John had a growing fear that he would lose touch with her forever. Their friendship had grown and waned several times over the years, and John could never figure out why. He knew that he found Libby attractive, he always enjoyed her company, but she had gone through phases where she became distant. It wasn't in John's nature to push, so he just let her go her way.

They were just starting to rediscover each other in the waning months of their senior year, John had gotten a coy happy birthday from Libby, surprising him that she remembered. Like all men with all women, he only knew her birthday was somewhere between January and December. Although John watched Libby from afar they really hadn't socialized together since mid way through 11^th grade. John had watched Libby suffer through several failed relationships, including a particularly rough one that ended a couple of months ago.

The last time he had talked to Libby was when he ran into her at the local soda shop. The students congregated there after school to trade war stories from the day, to eat a quick burger before after school sports, and to pair off occasionally, budding high school romances blossomed, flared and crashed, some in an afternoon, some over a period of months, most somewhere in between.

Libby had been sitting in a booth with Kelly, a friend of hers and had called him over to sit with them as he walked in the door. John was happy to see her smiling face as he slid into the booth. They had chatted about the day, who was falling for whom, which teacher was the total ass of the day, the normal trials and tribulations of an average American high school student.

"So, John, I read an article in Cosmo the other day that said all guys masturbate, is that true?" This from Kelly, completely out of the blue.

"Say what?" John looked wide eyed at Kelly in disbelief. Yes John masturbated, Cosmo was probably pretty correct, at least for 18 year old males, and from what he could figure it wasn't a matter of 'whether' but 'how often' and he never, ever, admitted it, let alone talked about it.

"I'm serious! Do you masturbate?" Kelly had a smile in her blue eyes as she asked the question. John looked deeply at her before answering, trying to determine what the smile said.

"umm I, uh, I have..." John said and hating the feeling of heat that went with the blush that crept over his face.

"See? I told you, even mild mannered John is nothing but a pervert..." and Kelly's voice lost its definition as John realized he was out of place, the sole Dolphins fan in a bar full of Jets fans, the sole soccer fan in a room full of football fans, the feeling one has when you realize you are no longer involved 'in' the conversation but have become the topic 'of' conversation. A really shitty feeling.

And the laughter coming from Libby wasn't the beautiful almost musical twinkle like sound that he looked for, almost groveled for, it was a biting, bitter laugh. John stood up, and slowly made his way to the door, not saying a word, but vowing never to set foot in that place again, never to talk to either of them again. He hadn't been back since and hadn't had a substantial conversation with Libby since either. He sometimes wondered, particularly when he saw Libby, whether he was making a mountain out of a molehill, then he remembered the hurt of the ridiculed, the outsider, and he always looked away.

Over the past few months it became apparent that Libby was trying to get him to talk to her. She would show up in crowds and always seemed to gravitate to him. The first few times John turned red and slowly wandered off. After a while, he was comfortable to stand next to her in silence and finally, only recently, he had started to respond to her questions, short answers but responses none the same.

Then came graduation, a huge crowd affair and once again Libby ended up next to John the crowd swirling around them, Libby walked up to John, stood on her tiptoes and kissed him on the cheek.

"Umm what's that for?"

"Congratulations John... and... well, thanks"

"you're welcome but thanks for what?"

"Thanks for being a friend... when it was hard... thanks for always being there."

" Uh sure, no problem" John wondered how she considered it being a friend when he had been avoiding her for the past year, but hey, if she wanted to believe that, who was he to argue?

As John leaned down to kiss Libby's cheek the crowd surged and pressed them together, as his lips were just making contact she turned her head and caught his lips with hers. Her arms went around his neck and pulled his face to hers, her soft lips opening, her tongue pressing for entry, finally gaining it she kissed him fully open mouthed. John was stunned to say the least. As she pulled back slightly she took his bottom lip between hers and suckled it gently. Her eyes opened and she looked deeply at John. The rush of emotion that John felt was unlike any other. He knew he loved this woman, knew he always had, as hard as he'd tried to avoid it, to suppress it, it all came back in that instant, looking deeply at her.

"What're you doing tonight John? You going to Georges' for the party?"

"Hadn't really thought about it."

"Can we go? I mean can you take me?"

"What about Kelly and the others... I don't really know them very well... I... Umm... I don't really fit in... with them I mean..." John hated the blush that flushed his cheeks, he knew he blushed and hated it every time.

"Come on John... It'll be fun I promise..."

"Really Libby I don't think so..."

"Are you still worried about that time in the soda shop? With Kelly I mean?"

"Yeah, that wasn't very much fun."

"Don't worry about that John, I'm really sorry that happened, I knew that was still bothering you, we'll talk about that later."

"But..."

"No buts John... Pick me up at my apartment at 7?"

"You have an apartment?"

"Yeah! Its really cool... you'll like it, I just got it last week. Mom and Dad are helping with it while I'm in school. They figured it'd be easier to find one now instead of waiting 'til college starts in the fall."

"Where do I go?"

Libby gave John directions, another quick brush of her lips with his, and she disappeared into the crowd. John caught a glance at her as she reached her normal group of kids. She caught his eye and smiled at him across the crowd, then was lost as the group wandered over the hill. He was still stunned but once again noticed the surrounding crowd, almost as if he had just woken up, his friends patting him on the back in congratulations on his graduation. He smiled, his focus still inward as the realization that he'd had his most passionate kiss ever in the middle of a crowd with a girl that he'd resigned himself to loving from afar.

When John got to Libby's apartment he walked to the door and knocked.

"Hey John! Come on in..." and she walked into the apartment to drop in to an older upholstered chair. "We don't have to stay at the party too long but we do have to go..."

"Its ok I'm ready for this... You ready to go?" His shoulders hunching slightly, his back straightening as if he was just called from the waiting room to the dentist chair for a root canal, he had an intensely forboding feeling as he entered the apartment. He had a feeling that he knew had to be reminiscent to the one the Christians had right before being fed to the lions.

"No, no sit down John" and she patted the sofa next to her. She pulled her legs up, sitting Indian style with legs crossed at the ankles, her jeans tight around her slender thighs, her white shirt showing just a little of her flat belly, her pert, small but expressive breasts, unconfined by the restriction of a bra, as was her normal style. John sat on the far end of the couch and looked at this woman. She was breathtaking, her small ski-ramp nose, chiseled jaw, pure white teeth, with just a slight turning of the front one to give her smile character. Her jaw gave way gracefully to a thin long neck that dissolved into shoulders that made one want to kiss them, with skin that looked so soft, clearly outlining the underlying shoulder bones, which were partially hidden and playing hide and seek under her slightly longer than shoulder length dirty blonde hair. Her hair, while beautiful and well maintained with a shine that made even the sun more beautiful, was always slightly disheveled, the silky tresses not quite willing to cooperate. John had found that all other women paled in comparison to Libby, and now had living proof sitting in front of him.

While John and Libby had never had a boyfriend/girlfriend relationship Libby kept John from putting the make on anyone else. John had tried to revolt from the situation by having a girlfriend and flaunting her in front of Libby but it didn't seem to bother her and it bothered him, a lot. While Libby always seemed to have a boyfriend, they changed regularly and never seemed particularly important to Libby. John had loved Libby from a distance for many years now, it had to be at least four.

Libby had always described their relationship as one of friendship, a brother sister type of friendship, although John never really understood that. He always fought with his sister like cats and dogs. Over the years John had been her confidant, her sounding board. She hung out with a different group of kids, revolved in a different circle than he did. She was the football player crowd, he was soccer, she was party oriented and he was cerebral, not quite dorky but perhaps slightly ostracized for his intelligence. He was the one she would call when she got home from the party everyone wished they were invited to, but John hadn't attended.

Although the idea of going to this party was completely against his idea of a good evening, he would do anything for Libby, and besides he had this brief interlude alone with her, and the added bonus of being able to watch her all evening.

"I'm so psyced school's over... Have you decided what you're doing in the fall? We haven't talked in so long I don't even know where you're going or if you're going to college."

"I got offered a couple of soccer scholarships, but I haven't made up my mind yet. I have to make a choice in the next week or two."

"Cool! a scholarship?"

"Yeah, a full ride... I'm going to work over the summer to try to save some money but I won't even have to pay for books, and as long as I live on campus I even eat for free."

"John we should go, but I have to tell you something first."

"uhh ok..." that sinking feeling coming on, John was sure what she was going to tell him was that she was meeting someone at the party, so all he had to do was drop her off. He was taken aback by the abrupt change of subject, he almost glanced, almost looked to see I the lions were circling.

"John, I'm really sorry I've taken you for granted while we were in high school... I umm... really do appreciate you being there for me." John's insecurity hit a high peak. "... was wondering if, umm we could like, be a couple for a while... Kind of try it out I mean... um... you know what I mean?"

It was the first time in recorded history that John ever saw Libby as anything but completely sure of herself, the first time he ever saw a lack of confidence in her demeanor, shy, insecure. He noticed that she was still cute when she blushed, actually even more attractive, if that was possible.

"You mean... you and me?" John's eyebrows rose in incredulity.

"I mean, I know we've always been like brother and sister, but I've always compared the other guys to you and... well... I never really had any fun with them like I do with you..."

"Really? You mean you and me?" John knew he was repeating himself but he just couldn't quite help himself. "But we're... um, so different... You hang out in different circles Libby... what would your friends say? Like, Kelly goes out of her way to make me feel like shit..."

"That's because you intimidate her... You're smart. I think she likes you."

"That's nuts."

"Can you think about it? I mean for a little while?" She leaned over and cut off any response he could've given by kissing him lightly on the lips. She pulled back and looked deeply into his eyes. He noticed how bright her eyes were, the color of the Mediterranean off of Greece, dark blue, and just about as deep. "Come on John, we've gotta go."

John didn't even notice the ride to the party, couldn't even tell you if he stopped at the stop sign or not, never noticed the traffic light. He could only hope he was driving on instinct and actually obeying at least some of the laws of the road. His mind was reeling when they walked in the party and Libby took John's hand.

As all parties do, this one rose and fell over the hours, the house filled, people got drunk, people passed out, people left. The keeper of the keys evaluated everyone before they left to determine that someone in the group was sober enough to drive. Libby drifted off during the party and John spent some time actually talking to Kelly and Libby's other friends for the first time, and, surprisingly, found that he was enjoying himself. It was the first party he ever went to that he didn't just hang out in the shadows and observe.

Libby came and went throughout the party, always departing with a brief kiss, and when she touched his arm as she came back he felt that flutter of the heart, the burst of warmth that gave him confidence that he'd never had before. He'd have to figure out the dynamics later. He got through the keeper-of-the-keys test with flying colors, he didn't really drink much during the evening, but he did have trouble saying the alphabet backwards, always had sober or not. Again his mind was reeling as Libby took his hand and held him close as they walked towards the car. John could smell Libby's hair, feel her hip move as she walked, feel her breast rub against his arm as they approached the car.

He was amazed at the turn around he'd gotten from Libby and was still somewhat dubious. He was still afraid this was some kind of a joke but he knew Libby would never do that to him, well, perhaps... he hoped as hard as a human being could hope that she wouldn't. As John pulled up in front of Libby's apartment he opened his door and went to Libby's side of the car with the thought of opening her door for her. She was already standing by the car by the time he got around it with an unsure smile on her face.

"I'll just walk you to the door..." John felt as awkward as the phrase sounded. He was thankful for the darkness, as he knew he was blushing again.

"You don't want to come up?"

"Um uh... yeah... sure... I mean I'd love to!" John hated it when he stuttered.

As they walked in the door Libby once again settled on the corner of the sofa and John stood just inside the entrance watching her, unsure where he should sit. As Libby got up he watched her uncoil from the sofa, and once again marveled at the beauty and grace of this creature as she walked to John. Her small pert breasts, nipples slightly erect and showing through the fabric of her top, her slim hips and flat stomach that only the young can achieve, long tapered legs, the shape of which was still apparent even through her jeans, ending in slim ankles and dainty white sneakers. The way she moved was hard to describe, fluid, languid, feline perhaps.

She put her hands up on John's chest and laid her head against his chest. John's hands, as if with a mind of their own, slid around Libby. He had always wanted to hold her like this, her hair smelled of strawberries and tickled his nose, her shoulders felt so small in his arms, her small body pressing against him.

"hmmm this feels good John, it feels right..."

John was terrified. He shuddered slightly and tried to implore his cock to remain soft. With a mind of its own it continued to grow and he started to worry that Libby could feel it.

"what's wrong John?" Libby said misinterpreting his body language, the growing tenseness as he tried to keep his hard on away from her, his body stiffening with the effort. Her hands slid around his back and her hips pressed forward. John could once again feel the blush caress his cheeks as his hard cock made contact through his pants with her flat belly. Libby looked back and could see the embarrassment on his face. She looked at him deeply once again before sliding from his arms and walking towards the small kitchen. "Do you want a beer?" she asked over her shoulder.

"Umm yeah I'd love one" He was unsure if she had broken off contact because of his embarrassing condition.

"Have you made a decision John?" the nonchalant manner the question was asked threw John off for a moment.

"... a decision?"

"Yeah, about you and me" Libby looked at him through the little opening between the kitchen and the dinning room/living room.

"oh! Uhh I dunno Libby. We've been friends for a really long time, I wouldn't want to fuck that up. Oh! sorry" Scrunching up his shoulders, his hand in front of his mouth as he realized what he said. He adored this woman, he wanted to be with her so badly, but the possibility of losing her friendship was almost more frightening than the fact that she seemed to like him, almost like she had harbored the same feelings he'd always had.

Libby walked into the living room and settled back down on the couch. "John, come sit down with me..." and John walked over to the recliner and sat down. "John, over here..." and Libby smiled tolerantly at John. He decided the only way she wouldn't see him constantly blushing was to have an eternal sunburn.

John wanted nothing more than to be a couple with Libby... He smiled as the irreverent thought popped in his head that he'd really like to couple with Libby too... but he had to be sure. He knew if she wasn't serious, and if he didn't play his cards exactly right he would blow something he had longed for for so many years and a friendship that would make life so bland if it went away. He sat stiffly next to Libby.

"Libby, you're beautiful, you're popular, I've thought about being with you for so long... I... uh... I'm just... shit, I don't how to say what I'm feeling..."

"I don't understand John, we always have fun when we're together, we've known each other for so long, you're the best friend I've got, I just can't see anything wrong with it."

"Yeah, but... well, like now is a good example. I've never been at a loss for words with you, until now, I've never been uncomfortable being near you, until now. I've always been able to tell you anything with no fear, and now... well I don't know what to do..."

"what do you mean... you don't know what to do?"

"I don't know if I should just sit here and talk to you or kiss you..." John looked down at his hands in frustration. He'd never felt so awkward. "You... um, have experience, and I... well... I don't."

"I don't have as much experience as you think I do John."

"But you've had boyfriends..." a plaintive tone to his voice showing the anguish that John was feeling.

"Yeah, and every time they wanted to makeout I just couldn't get into it. I... umm I thought about you... There! I said it. That's usually why we broke up." Now it was her turn to turn red and look down at hers hands clenched tightly in her lap.

"You thought about me?" The look of incredulity returned to his face. "Really?"

"Yep." And she turned her face to look sideways at John.

"Why didn't you ever, well, tell me or something?" He was struggling to keep his face from breaking into a totally shit eating happiest moment of his life type grin.

"I thought you'd make the first move. I didn't know how... and girls aren't supposed to..."

"I had no idea! I thought you thought of me as... a... umm, brother or something." John again looked down at his hands, shuffled his feet under the glass coffee table a bit. "I'm... uh, I don't know what to do again..."

"Whaddaya mean John?"

"I mean I don't know whether I should try to kiss you or... fuck." Frustration was apparent in his voice and by the clenching of his hands.

Libby could tell how upset and uncomfortable John was, he was so upset he didn't even apologize for the 'fuck' this time. She tried to make a joke to get John to relax. "John, it would be my first time so, if that happens we probably should kiss a time or two beforehand, don't ya think?"

John turned and looked at Libby, staring deeply into her eyes. Libby could actually see the wheels turning and realization dawning as he understood she was teasing him. She was fascinated by the transition as realization came, then a hearty laugh. She felt so much better knowing they had passed the most awkward time and their relationship had returned almost to the comfortable state but a little deeper than it had ever been before in that moment.

Libby leaned over to John and gave him a small kiss, just a brushing of lips more than anything. John's response was to kiss her back his hands still in his lap he followed her slightly as she pulled back. She laid down into the corner of the couch and John slid down with her laying his head on her chest. Libby put her arm over John and held him close to her, John's fingers idly tracing random patterns on her arm. Goosebumps rose on her skin as the tingles went from his touch to spread throughout her body. She was amazed at what a simple touch from John could do.

John leaned up to kiss Libby once again, kissing her lightly on the chin. Sliding up against her, he could feel the swell of her breasts against his chest, her legs next to him, the upper half of his body on top of her, his arms supporting his weight and he leaned in and kissed her. Her lips were so soft and supple, they parted and took his bottom lip between hers, gently suckling. His reaction was almost instant as his cock once again hardened. He was sure she could feel it against her side and he tried to slide a little more of his body off of her so she wouldn't notice. As he lifted up slightly she bent her leg forcing it under his hips giving him no choice but to slide fully between her legs, his cock pressing against her pussy through their clothes. Her tongue invaded his mouth and wrestled with his tongue as her hips began a subtle undulation.

John's cock tingled like it had never tingled before and he lost the fight against the instinct to grind into her harder. She pushed hard against him sliding down further on the couch to a fully reclining position and he let his weight settle a little more firmly on her. "hmmmm" she moaned into his mouth as they continued to kiss.

John was amazed that just grinding with her could produce such sensations. He felt better than when he stroked his cock, except for perhaps, right before he came. The feelings just grew and grew in intensity and he felt his balls pull up against his body preparing to unload in his pants.

"oh... oh... Umm..." and John pushed himself off Libby staving off the impending orgasm and embarrassment.

"John, what's wrong?"

"Uh nothing... really..."

"Come on... what's wrong... that didn't feel good to you?"

"oh god did that feel good."

"Then why did you get up?"

"Because"

"Because why? Come on John! What's wrong?" her voice became imploring and when John worked up the courage to look at her she looked as if she was on the verge of tears.

"It felt too good Libby... I was... umm... getting close..."