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Tales from School

Part 7

Tales from School, by Some Writer


Part Seven: First Time


Tim and Ruby lose their virginity.


In the intervening few weeks since their respective sexual encounters, Tim and Ruby had become firm friends, and more besides. They had first started talking to each other one lunchtime and had found that they enjoyed each other's company. Tim had never spoken much to Ruby before but now found that she was caring, funny and strong-minded, not the shy awkward type he had thought her to be. Likewise, Ruby had found that Tim was not the annoying geek that she had first taken him for, but was in fact a kind, funny boy who looked at her in a way that no boy had before, not even Oliver; a gaze borne of love and desire, the two indistinguishable from each other. She had not spoken to Oliver since their last meeting but that no longer mattered to her, now that she had found Tim.

"So, I was wondering if you wanted to come over to my house after school," Ruby suggested one lunchtime.

"Yeah, that would be cool," Tim said before sipping his drink, not realising her intention.

"My parents will be out," Ruby mentioned nonchalantly. Tim stopped drinking and looked for clues in her expression.

"Oh right," he said noncommittally, unsure if Ruby was trying to imply what he hoped she was. Ruby took Tim's lack of interest to mean that he was not having the same thoughts as her. So it was that they walked home from school together, both wanting the same thing but believing that the other did not. They arrived at Ruby's house and went up to her room.

They sat on her bed, side-by-side, an awkward atmosphere filling the room. They turned to each other and hugged before kissing, more of a smooch than a passionate lovers' kiss. Their lips met again and again as they kissed. It was not the first time they had done so, but it was still a relatively new activity for the couple.

After a while, Tim slipped his hands underneath Ruby's jumper and began rubbing her back, feeling that he should do something to advance matters but afraid that trying to remove her top might be deemed too forward. He was proved wrong when he felt Ruby take hold of the hem of his own jumper and slide it up his torso. They broke off their kiss to awkwardly remove each other's jumpers. Emboldened by Ruby's initiative, Tim reached around Ruby and fumbled with her bra until he managed to undo the catch before pulling the straps down Ruby's arms. Then he was kissing her again, this time on her neck before moving slowly downwards.

Tim guided Ruby to lean backwards and she lay on the bed as he explored her upper body with his mouth, kissing down her upper chest onto the soft pillowy mass of her breasts, squashing his face against her large breasts, sucking on her teats as if feeding from them. He paused his frantic kissing to gaze at her semi-naked body. Ruby realised that Tim was the first person to see Ruby naked from the waist-up (Oliver having only been concerned with her lower half) but she did not feel nervous or worried about what he would think of her body.

"You're beautiful," Tim declared with a silly grin on his face, and for that she pulled him to her again and kissed them, their naked chests pressing against each other. Tim ran his hand down her side to rest falteringly on her waist. Ruby stopped kissing him and nodded at him with a smile and a twinkle in her eye as she whispered: "Go on." Tim's hand immediately moved to the middle of her waist and unfastened her trousers. Together they slid the trousers down and Tim pulled them from Ruby's ankles, leaving her totally naked beside him. He paused to look over her naked body.

Ruby's figure was classically feminine, comprised of curves and soft edges, the opposite of waif-like supermodels. Her legs were round and almost exactly circular, with smooth youthful skin and a few dotted moles. Her bush was thick and full, brown curling hairs sprawling this way and that. Her stomach was round rather than flat, but could not be termed large. Her large breasts had collapsed onto her chest with the force of gravity, her perky nipples sticking up into the air, the only sharp points on her curvaceous body. Her areolae were large, and almost the same colour as her skin, but slightly duskier. Her neck and face had a perfect complexion. Her face was pretty with a cute small nose and full cheeks.

For a moment, Tim mentally compared her body to the slender figure of Miss X, but that whole experience seemed so unreal now, like a private fantasy that had never occurred. Ruby was here - very real, and very attractive.

"So beautiful," Tim re-iterated, his right hand brushing tenderly through Ruby's hair. She lay on her back whereas he lay on his side, using his left arm to keep himself propped up. Ruby could not stop smiling back at him. Tim ran his hand down her side again to rest on her hip, ready to draw her to him again.

Instead Ruby spread her legs. "Touch me," she told him with a longing in her voice that made his heart glow. He placed his hand on her pubic mound, able to feel her wetness - her labia spread apart by the position of her legs, the secrets of her slit already exposed to his roving hand. Tim explored her sex with his fingers. He knew where the clitoris was to look at a girl's pussy, but that turned out to not be much help when the only sense available to him was touch. He found what he believed to be the right place and his novice fingers began rubbing in varying circles and lines.

"Mmmmm," Ruby said and pulled his head towards her to kiss him again as he fondled between her legs. She kissed him so deeply that their tongues met for the first time, initially by accident but then by design as they explored each other's mouths. Tim's fingers worked busily on Ruby's clitoris, too inexperienced to consider doing anything else with her pussy.

They stopped kissing and Ruby closed her eyes as she enjoyed Tim's awkward but earnest fumbling. Tim lay looking at her face, now slightly flushed, her mouth open as she quietly panted, moans of pleasure escaping infrequently from her lips while he continued rubbing for many minutes before Ruby broke the silence in the room.

"Uhhh - yeah - mmmm, yeah... I'm close," Ruby whispered, "yeah, yeah, uhhhhhhhh, uhhhhhhhhhh!" She came, her body trembling slightly beside Tim's, their two forms wedged together on the small single bed. He grinned with pride at his achievement and as her breathing slowed again, he became particularly aware of his unsated erection. Ruby lay with her eyes closed for a while and then opened them to look at him.

"Did you want your clothes or anything?" Tim asked, not sure what he was meant to do at this point. Should he point out his own needs, or were they going to stop there and redress?

"Let's just lie here for now," Ruby said and then realised that there was not enough room on the bed for both of them to lie on their backs. She shifted on to her side and shuffled away from Tim, starting slightly as her naked bottom touched the cold painted wall. Tim moved to lie on his back beside her and she began idly rubbing his chest with her hand, at which point she noticed the bulge - much more obvious when he lay on his back - in his trousers.

"Is that...?" she asked vaguely and Tim nodded. "Oh," she said. "I hadn't realised."

"You can pretty much assume that if there is anything vaguely sexual going on, it'll be like that," Tim explained. "It's not exactly rare."

"Oh," Ruby said and she giggled. "Can I take a peek?" Tim nodded enthusiastically and she unbuttoned his trousers and slid down his zip. His grey Y-fronts had a huge obscene bulge in them. Ruby shifted slightly so that she was able to push down his trousers and underwear, at which point his cock sprang free. It looked just the same as Oliver's had, and about the same size. She wrapped her hand around it and looked into Tim's grinning, expectant face, and her eyes scanned back down, slowly, over his whole body.

Tim had short brown hair and a slightly thin face. His body was similarly thin, the bumps of his ribs visible on his sides, his arms very slender yet somehow strong. Hair covered his pectorals, disguising any lack of muscle, and ran in a faint line down the centre of his chest. His hip bones stood out slightly but his stomach was not too thin. His legs were hairy, but outdone by the thick tufts around his proud cock, which was erect and demanding attention. Ruby made a decision.

"Get up and open the drawer under my desk," she told Tim. Bemused, and slightly unhappy about the interruption of his prospective hand-job, he completely removed his trousers and underwear so that he could stand up and open the drawer. Inside he found a condom, which he recognised as being a free one that they were all given during sex education. He held it up for Ruby to see. "Yep, that's it," she said. "You up for it?"

Tim swallowed hard and nodded. Ruby shuffled back into the centre of the bed as Tim carefully opened the condom wrapper, trying to remember what they had been shown in sex education. He got the condom the right way up and put it on top of his dick, holding the teat closed while he tried to roll the latex down over his cock. After a couple of attempts he managed it, and rolled the smothering sheath as far down as he could. He climbed onto the bed between Ruby's legs and lay over her, fumbling to guide his dick into the right position.

"That the right place?" Tim asked.

"Not sure," Ruby admitted. "Try it." Tim pressed forwards and Ruby felt his prick jab against her pubic mound.

"Down a bit and left a bit," she told him and this time his dick was in the right place. Ruby gasped out loud and then gently bit her lip as her pussy was penetrated for the very first time. It was a wonderful feeling, but too much for her to bear. Tim was smiling as he felt her pussy wrapped around his dick, glorying in the claustrophobic feelings of his cock's natural home. "Wait a minute," Ruby pleaded as she let her body adjust to the new situation.

As the two of them lay there in silence, Ruby felt that she should do something with her arms and legs; they were resting on the bed, in the absence of any other ideas. She tried to wrap her legs around Tim's back in mid-air but that proved too uncomfortable. She slid her legs down his body until her feet were on the mattress again, but this time they were planted next to his knees, her legs looped around his thighs, leaving Ruby's legs interlocking with Tim's. She reached her hands around his body and clasped them together behind his back, meshing the fingers with each other so that she could keep her hands together easily.

Ruby nodded at Tim and he began trying to thrust. Such a simple action turned out to be an incredible struggle as he realised that he was not sure of exactly how to do it. He tried using his legs but his feet had no real purchase. He tried bucking his hips but that seemed ineffectual. Ultimately he used his thighs, pivoting from his knees, his body moving in patterns that did not seem to properly match the angle of Ruby's vagina. Ruby held tight to him as he found his way, feeling more like a boxer in a ring clinging to her opponent than a delicate woman being made love to.

At first Tim kept his head above Ruby's, ready to kiss her, but that was too difficult due to them both bouncing around awkwardly. Ultimately it was easier to bury his head over her shoulder and work on the thrusting. He was now getting it sufficiently right that it was becoming quite pleasurable and he began grunting in Ruby's ear as he fucked his way towards orgasm.

"I'm close," he said gruffly in her ear, feeling that he should let her know.

"Go on then," Ruby said simply and then, aware that those words seemed inadequate, added a line from some porn she often watched: "I want you to come inside me." That was all the encouragement Tim needed and with a couple of brutal thrusts he reached his end, feeling his hot come spill from his dick, deep inside her.

Tim raised his head up to look at her and they both grinned stupidly at each other - grins that refused to fade for the rest of the day.


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