Libby & John: First Time


"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. Libby got up and walked to John. He watched her uncoil from the sofa, and once again marveled at the beauty and grace of this creature. 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 everytime 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."

Libby could tell how upset and uncomfortable John was, he was so upset he didn't even apologize for the 'fuck' this time. "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 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..."

"Getting close? Close to what?" And it was John's turn to watch the dawn of realization. "You mean you were going to...?"

John's face flushed again and he hated it as always. "Yeah."

"and that's bad?"

"It would've been... embarrassing, and messy."

"I've never done that before."

"You've never done what?"

"I've never made a guy... um... squirt before... I wish you hadn't stopped."

"Have you ever... you know... had an orgasm?"

"Lots of times... but never with anyone else..."

"Were you... uh going to? I mean now?"

"It felt really good but... no not yet... I probably could though..."

"Like that?"

"I suppose so... it... um... usually takes a little more... direct contact..." John was relieved to see the blush rush through her cheeks too.

"Libby I don't want to rush things... You're important to me... you have been for a really long time." John turned as he said it and leaned against the wall facing into the kitchen. He didn't want Libby to see his uncertainty. He heard her rustle, sensed her walking up to him and jumped a little when he felt her hands on his sides. She slid her hands up under his arms and held his shoulders back as she hugged him from behind.

"John, lets just let what happens happen... and if you wanna... um let it go then... let it go." Libby whispered in John's ear.

"Are you sure Libby?"

"I've never been more sure of anything in my life... I want to feel you... I want to make you feel good... I want to... be a real couple, in every way. I've never felt this way with anyone else before, and I think, maybe, I've always felt this way about you, I just didn't realize it." Libby's hands slid over John's chest still holding him close to her. Her hands slid lower, to his belt. John wanted her to stroke him so badly that his stomach sucked in every time her fingers approached his belt. Her fingers slid just inside his belt, and he tingled as she slid her fingers through his pubic hair. His cock had shriveled during their conversation but it was enormously hard now and he twitched when her finger made its first contact with the head of his cock. As a matter of fact it was the first time any female fingers had ever made contact with his cock.

Libby's voice was husky as her fingers struggled to feel the hardness that was encased so tightly in its cocoon of denim, "John, I want to learn, I want to learn with you, I want to feel you, I want you to feel me."

The feelings that were being created by her fingers were so much more intense than the feelings that he was able to create with his own hand. He turned in Libby's arms and she pulled her hand out of his pants as he pressed his pelvis against hers. John's lips caressed hers in a soft emotion filled kiss. He felt her lips part slightly, tentatively and his opened slightly, his tongue entering her mouth, her lips opening wide. John pulled back and looked at Libby, her brown eyes moist, intense.

"Libby, I want you so badly, but I don't want to rush things... maybe we should... umm slow down some..."

"John, we've been friends for years, I think I've always really loved you, I wasn't sure before but I am now, I want to learn with you, but, I want you to like it too."

"Libby I should go, I have to work in the morning. It's my first day, Dad got me a job with a concrete company, I really need to get some sleep... and I don't want to rush this." Then he smiled at Libby, "You want to try an experiment?"

"What kind of an experiment?"

"A 'certainty that you want me' kind of experiment."

"Ok, and if I do your 'experiment'" and she made quotation marks in the air, "Will you loosen up some? Will you understand what I've been trying to tell you all night? That I love you, that I always have loved you? And that I'm sorry it took me so long to realize it?"

"Well, I'll at least understand that you want me like I want you..."

"Ok I'll do it... whatever it is I'll do it." Her expression was a mix of frustration and pleading.

"When you go to bed tonight, touch yourself... Make yourself umm you know, and see if you think of me at the uh, right time... but you have to be absolutely honest."

"You really want me to do that?"


"You'll do it too?... and think of me?"


John kissed Libby quickly and walked out of the apartment quickly before he lost his nerve. As he sat in his car with his head down against the steering wheel he couldn't believe he hadn't gone for it. 'What the fuck is wrong with me? I've loved Libby for so long, and now I have my chance. First I almost came just dry humping her, to the point where I embarrassed myself and then I give her a stupid exercise? Awww fuck!' He turned the key and drove away.

Libby heard his car leave. She couldn't believe his car was actually leaving! She figured he'd come back, what guy didn't want to fool around. All these years she'd thought of John at the movies while fighting to keep guys hands out of her blouse, let alone out of her pants, fought off the octopus her dates had become while they were dropping her off in front of her parents house, ignored the lusty stares she got from her school mates. She had eventually alienated all of her boyfriends and the end result was that she finally understood how much she loved John, and she WANTED him to touch her and he wouldn't. What's wrong with me? She thought.

'Maybe he really does love me, maybe he's right and we should take it slower.'

She lay down on the couch and idly stared at the TV. 'He really wants me to masturbate? What if I don't think of him at the moment.'

Her hand slipped down to her chest and began drawing small circles around her nipple, and felt the little rush of tingles as it hardened beneath her finger. She thought of the feelings when she felt them rubbing against John as he held her close, of the tingles that she got just from him touching her arm, how she felt his arm brush her breast as she held him close while they walked to the car from the party.

Her hand traveled lower, over the smooth skin of her stomach showing below her shirt. Her hand absently undid the button of her jeans and slid inside. As her finger slid down through her pubic hair and felt her lips she found them engorged, with wetness seeping, she collected a touch of her juice and spread it over her clit, her two fingers forming a nice pocket for her clit as they began to travel in lazy circles.

It felt so nice to have John's weight on her, he was so cute, suspending his weight on his elbows as he hugged her. The feeling of his cock against her... she shivered and her fingers picked up their pace, pressing harder and she felt a renewed flow of juices lubricate her. She felt so lewd as she pressed against his hard on. She'd never done anything but try to let whoever she was with know that she wasn't interested in 'that', at least not with them. But she loved the feeling of trying to get John interested, of being able to let her desires be known. She remembered the tingles as he ground his hard on against her, how much she wanted him to take her clothes off and slide into her, where no one had ever gone. She thought of laying there exactly how she had, but naked this time, wondered if it would hurt, wondered if it would feel good, the feeling of fullness as he slid into her the first time... then her conscious thought dissolved as her orgasm took over.

Her head went back, her back arched, breasts thrust out, nipples at their maximum hardness. Her legs quivered as the sensation invaded her entire body. Her pussy clenching, her clit hard and sensitive, bursting in pleasure with each orgasmic wave. Her body began to relaxed, her ass hit the couch again and she shuddered an after orgasm tremble, her finger jerking across her clit setting her off again as she once again tensed, her moans that she distantly realized were hers.

"Oh! Oh god oh god..." she said to herself panting, trying to force air to her lungs. She had masturbated for years now but never had an orgasm that intense before. She lay on the couch, a thin sheen of sweat covering her body, beginning to feel cool in the night air. She pulled an afghan over her exhausted body and immediately fell asleep, legs apart, jeans undone, blouse pushed up around her neck, breasts exposed.

John thought about the evening on the short drive home. He had such a fun time at the party, the people he'd always assumed were different than him seemed to accept him as one of their own. He was still reeling over Libby, god he loved her so. He knew he did, he knew he had for so long. He walked in the house, went upstairs to tell his parents he was home, and went back down to his lower floor bedroom. His erection had never fully deflated and it caught his boxers as he slid them down. He laid in the darkness thinking about Libby, her face, her shoulders, her breasts, her flat stomach almost idly stroking the length of his cock.

He wondered what she looked like naked. He knew she would look every bit as beautiful as he expected her to. He wondered if she was 'doing the experiment' right then. His mind's eye had an image of Libby in her bed, legs spread, rubbing her clit. He had a flash of tingles, realized the pace of his hand had accelerated and that he had passed the point of no return, he tried to hold off, to stave off the inevitable, his body tensing, the veins of his neck standing out, the muscles of his arms and legs taut as he fought the rising tide, but his hand never stilled. He finally gave in to the pleasure, his hand still stroking his cock as the pearly white semen flew out of his cock to land on his chest, his stomach, the first three jets intense in volume, distance and intensity of sensation.

"Ohh! Oh... unh..." rough course grunts with each contraction of his balls forcing out another flying streamer of cum. The intensity of the jets diminished but not the intensity of the sensation as the cum boiled out of his cock, running down over his hand to pool in his pubic hair at the base of his cock. The speed of his hand slowed, not touching the oversensitive head of his cock but stoking up and down the still hard shaft of his cock. His breathing slowly settle back down to normal, his eyes slowly closing, rolling back in his head as an exhausted slumber threatened to over take him. He reached wearily into his dirty clothes hamper for a towel, wiped his chest and stomach off, shuddered as the towel wiped off the still sensitive head of his cock. He dropped the towel to the floor, rolled over on his side and was asleep, a content smile on his face.

Morning came early to John and although he thought he was in good shape he was doubly sure he wanted to go to college now, he used muscles he didn't know he had. He came home tired, dirty and a little frustrated that concrete could seem so fucking complicated. It seemed so simple from the outside, but there were so many considerations to keep in mind while it was being poured, different additives, levels, forms, all sorts of shit he'd never considered.

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byJust_John1© 31 comments/ 697078 views/ 64 favorites

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