7 comments/ 90781 views/ 55 favorites Chloe's Cherry By: YoureWet Harry stopped pedalling and slowly cruised towards the houses she had told him about. One of the doors was ajar, and he could see her face in the semi-darkness behind it. Harry approached the door and she quickly opened it up, backing away to let him push his bike into the living room. He closed the door behind him and turned to face her. She was smiling at him nervously, with red cheeks, and a look on her face that said she couldn't believe they were doing this. She looked so beautiful, he thought, so demure. He couldn't believe she was going to let him do this either. She was only 18, and still had a few weeks left before leaving school. He was a full twenty years older than she was. Harry scanned down her 5-foot frame slowly and without subtlety. He wasn't usually able to do this - with the other parents around he could only sneak glances - but now he could drink her in properly. Her slim but curvy body was accented with a white vest top which clung tightly to her breasts and stomach. Below this she wore a little blue and white skirt made of a stiff fabric which flared out at 30 degrees and hung in rough waves which circled a few inches away from her smooth legs. It can't have been more than a foot from waistband to hem, and the way it hung only made it look shorter. Harry guessed it covered what it intended to with only an inch or two to spare. It was perfect for what they had in mind. "Hi Chloe," he said, with a huge grin on his face. "Hey," she replied, beaming sexily. Here they were at last. Together. Alone. And, after today's internet chat, horny as fuck. They kissed briefly, like old lovers, and then made some small talk about the messy state of the room. Chloe and her mum were still in the process of moving in. Every surface was covered with unopened boxes. There was a sofa, but it wouldn't be possible to sit down. "So, shall we go upstairs?" she asked, smiling naughtily. Harry smiled back and raised his eyebrows, and watched her start to ascend. He followed Chloe up the stairs a couple of feet behind, so he could look up her skirt. She looked back at him. "Are you walking behind me so you can look at my ass?" she asked, jokingly. "Yes," admitted Harry. "Oh," said Chloe nonchalantly, and she carried on walking up the stairs - more deliberately now, so he could enjoy the view. The stiffness of the material prevented the skirt from draping, so the back stuck out behind her at an angle. From where Harry was, he could see right up it. He tracked his eyes up her thighs to her peach-shaped ass, which was half-exposed to his view. It was a thing of beauty - pink, smooth, and perfectly shaped. In between her bum cheeks he could see the thin trace of a green G-string. His eyes followed it downwards to where it disappeared into a diamond-shaped gap between her upper thighs. As she climbed, her thighs would separate for a few moments at a time, opening the gap and giving him brief tantalising glimpses. He saw the material widen out, barely covering her pussy. He could just about make out the outer edges of her pussy lips, and then her legs would come together again, hiding them from him. Harry had a firm semi already. He had fantasized about seeing up Chloe's skirt ever since he first met her - it was the smallest part of his fantasies about her, but now it was happening. She was letting it happen; allowing him to see her flimsy G-string beneath. There was no question that he was going to be taking her virginity tonight. Just the thought made his dick ooze a few drops into his boxer shorts. But they'd been wet with anticipation all day anyway. When they reached the top of the stairs, Chloe took Harry's hand and led him into her room. The lighting was subdued. A large bed sat under a sash window, decked in black cotton sheets. A computer desk sat to the side of the bed, and various boxes lay scattered around the floor. This would do fine. Except: "There's no curtains," noticed Harry, "we don't want anyone seeing us." Harry's wife didn't know he was here, of course; she'd gone to bed, leaving him downstairs smoking. He often stayed up a few hours later than her, thinking, listening to music, watching TV. He didn't usually cycle into town to deflower schoolgirls though. Chloe found a spare sheet and Harry hung it carefully on the curtain rail to afford them the privacy they were going to need for what was coming. "I brought some wine," Harry said, producing a bottle. Chloe found some tumblers and he poured them half a glass each. "Cheers," he said, and they chinked glasses with a giggle. Harry turned to the computer desk and connected his iPhone to the speakers, so they could have some background music. He noticed the webcam, and smiled to himself. He'd watched her masturbate for him on that webcam. She'd told him she loved him with that keyboard. He turned around again. Now that everything was set up, he could take his new girlfriend in properly. Chloe was sitting in her little outfit on the edge of the bed, her skirt flattened on her lap, with lovely smooth silky legs poking out and her bare feet hardly touching the floor. Her knees were slightly apart and her thighs were lightly pressed together as they disappeared under her skirt. She looked absolutely good enough to eat. He gazed back at her face and she was smiling a little too much, slightly nervous. She looked so young, so innocent, and so beautiful. Most of the boys in her school wanted her, but she had rejected them all and chosen to give him her most prized possession: her virginity. It was, in anyone's book, a great honour. His mouth suddenly felt dry. He swallowed and sat down on the bed next to her, never taking his eyes from hers. Harry took her hand in his hand and leaned in to kiss her. It was brief, but electric. He shuffled closer to her, releasing her hand, and putting one arm snugly around her back. Then he gently placed his other hand just above her knee. They leaned into each other, closed their eyes, and kissed more deeply. Harry loved the way Chloe's lips felt - they were huge and soft and wet, and enveloped his whole mouth. He had kissed her like this once before. He'd gone out in the day a week earlier and secretly met her for a picnic; they'd had their first kiss then. In fact he'd ended up on top of her, grinding her through her shorts, and she had been kissing him aggressively in return. Her kissing now was more gentle and passionate. Her tongue was less probing and more relaxed, and she allowed him to tongue her back tenderly. Months of yearning were finding their first tender expression. Harry became hard quickly, and his dick automatically slid upwards inside his trousers, lubricated by the wetness he'd been experiencing all day. As they carried on kissing, Harry slowly slid his hand from Chloe's knee to the upper surface of her thigh. She started kissing him more insistently. This was the first step, and they both knew it. Harry started inching his hand upwards. Her leg felt amazing - warm and smooth and perfect. He got harder and harder the further his hand moved, the closer it got to her pussy. He wanted to touch it so badly. He had fantasized about this for so long; it would be the first time she would ever be touched there by a man, and he was hoping that she would be extremely wet for him. Their mouths pressed harder into each other and their tongues became more solid; their movement more rapid and insistent. The ice had been broken and they were both enjoying this moment; they both moaned with desire, and with the unspoken promise of what was to come. Harry slid his hand an inch further up Chloe's leg, and moved it inwards so he could touch her delicate inner thigh with his fingertips. Chloe gave a high but quiet moan, and instinctively moved her knees apart a few more inches, so he could have access. As Harry stroked her sensitive skin, he imagined her pussy getting wetter under her skirt. She knew where his hand was headed, and he knew she wanted him to touch her there, to take her innocence. Tonight, she was giving herself to him completely. Still they kissed, constantly, as if this might be the only chance they would ever get. Chloe stroked Harry's stomach through his T-shirt as they kissed, while his hand continued its slow and deliberate journey up her virgin thigh. His hand touched the hem of her skirt. A milestone: the last line of defence before her panties. It offered no barrier; he crept his fingertips slowly underneath the loose skirt, and the material slid easily over them. There was no resistance. He savoured the situation as he slowly pushed his hand further up her skirt. So many times he'd sat next to her, in her uniform, and chatted to her politely as he wondered what she would do if he just slid his hand under her school skirt and started touching her there. Chloe shuffled slightly on the bed, moving her knees further apart and fully separating her thighs. He could feel her warmth on his fingers now, a damp heat emanating from between her legs. He continued sliding upwards. Soon her thigh began to curve inwards again. He felt the contour, enjoying the feeling of knowing what was coming next. Her thigh would continue to curve inwards until its most sensitive point, right at the top, where it met the skin around her pussy. He slowly let his fingertips drift up the curve of her thigh until he nearly reached that point. He paused, savouring where his hand was, and what he was about to do with it. They carried on kissing rhythmically, with renewed vigour, both knowing what was going to happen next. Harry waited as long as he could bear, then slowly detached a finger from Chloe's thigh. He moved it slowly through open air, just a few millimetres, until he felt fabric. Her underwear. He slid his hand in a little more, until his finger was nestled in the crotch of her G-string. It was narrow here, mostly edging, with a centimetre of thin fabric between. He felt the edges curl around his fingertip as he applied slight pressure. Gently, he started stroking her pussy through the material. Fireworks went off in his head as the moment caught up with him. He had crossed a line now, a line he was only supposed to cross with his wife, and a line Chloe had never crossed with anyone. They stopped kissing, and Harry looked at Chloe while he gently rubbed his finger up and down, lightly massaging her pussy through her panties. She had her eyes closed, enraptured. Harry felt a sway of emotions. Nobody had ever touched her there before, and she had permitted him - chosen him - to be the first. How many times had he fantasized about this? Here he was with his hand up her skirt, rubbing her pussy through her underwear. From here, anything could happen. She opened her eyes and smiled at him, then put her hands behind her and leaned back. She seemed happy, content, as if there was nowhere she would rather be, no one she would rather be with, and nothing she would rather be doing. She closed her eyes once more. Harry focused on the feelings in his finger. He could feel the two edges of the G-string curling snugly around his fingertip, slightly chafing him as his finger slid in the groove they formed. The fabric between them had initially felt rough against his skin too, but as he moved it up and down it was becoming slick. Chloe was getting the material wet, almost slimy. He pressed a little harder with his finger. The flesh below gave way and the fabric slipped easily between her pussy lips, oiled by her juices. He heard her quietly gasp. With the material hugging his finger like this, he couldn't feel her directly yet, but he knew now there would be no need to remove her panties just yet - he could just slip his finger under the fabric and he'd be inside her pussy lips, feeling her wetness. She had chosen her outfit well - the G-string offered no defence at all. Harry watched Chloe's glowing face as he moved his finger to the edge of the G-string. He rolled his fingertip to the edge and around to the other side. Slowly, millimetre by millimetre, he moved his finger inwards, his fingernail sliding against the inside of the G-string, until the tip suddenly felt very warm, and very wet. Harry gave out a long low moan of fulfilment. He had dreamed of this moment for so long, and finally he was here. His finger was inside her pussy lips, sliding in her juices, and she was even wetter than he had imagined. He started running his fingertip around, hardly moving, sliding frictionlessly just a few millimetres up and down each time. Chloe's mouth fell open slightly and she moaned, quietly and contentedly. He watched her quietly purring, with her head back and her eyes closed. She looked so beautiful, and her gentle moans made him feel so good inside. He felt his dick twitch. It was pressing hard against the inside of his jeans now and he could feel that he was soaking his clothes in his own precum. A large dark area was showing on his trouser leg. He'd never been so turned on in his life. Harry shifted his hand and turned his finger downwards so the whole length could slide through Chloe's wet groove. He bent his fingertip so it pressed inwards against her warm slippery flesh, then he gently slid his finger down until he felt the slight dip at the entrance of her pussy. No one had ever put a finger inside there, except Chloe herself. He applied gentle pressure and bent his fingertip, pushing the soft part of his finger against Chloe's virgin hole. Time seemed to stop; he felt every sensation as her pussy gradually yielded to the pressure, his fingertip slowly pushing the sides apart. He was still on the outside; the wetness was only on the pad of his finger so far. As he pushed slowly inwards, the wetness spread further. He curled his finger more and felt the end of his fingertip go inside her, then a little more and his fingernail was sliding against her wet vagina. Then he gently pushed, and the end of his finger slipped inside her, up to the first knuckle. Chloe opened her eyes and looked at him with a serious, lustful expression as she gave out a deep moan of sexual relief. Harry was hopelessly turned on. He could feel the wetness streaming out of his dick; there was no stopping that now. This had gone well beyond fantasy. He had his finger inside his favourite schoolgirl's soaking wet pussy. He had fantasized about this so many times. He'd wanked himself off every night thinking about fingering her. She'd be behind the bar at the rehearsal room and he'd be to one side of her. They'd both be talking to someone else, but while they talked, Harry would sneak his hand up her skirt - behind the bar so no one could see. And then he'd make her cum while she bit her lip to stop herself making any noise. Or, he'd drag her into an empty dressing room at the theatre, sit her on the dressing table, lift her skirt, rip her knickers off and then finger her until she came - then send her off to the stage with no panties on, and her own cum dripping down her thighs. When he'd had those fantasies, he had never dreamed they would come true. They flashed quickly through his mind as he slowly and gently fingered her in real life. Suddenly, Chloe sat upright and went for the button at the top of Harry's jeans. She kissed him as she grabbed the top of his jeans with both hands and tore the button from its hole, separating the two halves. Harry breathed in sharply. He had expected Chloe to enjoy being touched, but he hadn't expected her to dive in without being asked and rip his jeans open. This was good. The sudden release of pressure around his waist made Harry feel free, and the fact that this young virgin had done it made him feel dirty and sexy. Chloe unzipped the fly on the jeans in another moment, and his rock-hard cock was relieved from the pressure it had been under ever since Harry looked up her skirt on the stairs. His cock slid around wetly inside his boxers as Chloe folded back the button flap letting her see Harry's underwear for the first time. She flattened her hand and placed it directly on the visible part of his underwear. Parts of it touched his cock, and parts of it found the wetness which was all over his boxers and jeans. "You're soaking wet!" she exclaimed. Harry just smiled and nodded. No one had ever made him as wet as Chloe made him; this was fairly typical for him after they'd been talking for a few hours online, but it was the first time Chloe had felt it. "Like I said, I'm always wet now," he replied, "ever since I met you." Chloe cupped her hand around where she could feel Harry's dick. It was pointing along Harry's thigh, at right angles to his legs. She squeezed it firmly but gently and was rewarded by a long sigh from Harry. More wetness oozed out of the end as she played, while Harry gently fingered her with a slow and shallow in-and-out motion, her juices slowly flowing down his finger. "Let's lie down," she suggested. "OK!" Harry laughed, then he pushed Chloe's shoulders firmly backward with both hands. She went crashing downwards onto the soft bed with a squeal of excitement, her skirt flapping up over her stomach, revealing her navel and panties to his lustful gaze. He leaned over and took off his shoes before turning around and lying down face-to-face next to his beautiful teenage mistress. He brushed the hair off her face and stroked her cheek with his palm. "I love you," he said, then he kissed her. It was a loving kiss, full of deep emotion, and they melted into each other. Chloe looked into Harry's eyes. "I love you too," she said. They carried on where they left off. Harry slid his hand onto her navel, across her exposed panties and down onto her wet pussy, pushing his finger inside her once more. Meanwhile Chloe put her hand inside Harry's jeans, and then inside Harry's boxers. Her skin felt cool against his groin as her hand moved around inside his boxers, searching for his dick. She found it quickly, and pulled it into a more vertical position inside his underwear. It was wet all over from his precum. She slid her hand up and down the shaft while Harry sighed and moaned and, in response, pushed his finger inside her to the second knuckle. She gasped loudly and started moving her hand faster on his dick. Harry pulled his finger back out and rubbed two fingers around inside her lips, wetting them with her juices. Then he pushed the two fingertips against her hole with a little more force than before. They quickly slipped an inch inside her, stretching her pussy as they went. Chloe cried out in pleasure, which just sent more wetness out of Harry's dick and made it twitch in her hand. She squeezed it tightly. Harry was in heaven, his two fingers slowly fucking the gorgeous schoolgirl, while she massaged his shaft like an expert. "Does that feel good?" he asked. "That feels amazing," she told him breathlessly, "but take your jeans off, I want to hold your dick properly." Once more, Harry was delighted and turned on by her taking the initiative on the night she was losing her girlhood. He pulled his jeans down over his knees and feet and threw them over the side of the bed. Harry turned back, in just his T-shirt and boxers, to a vision lying on the bed. Chloe had removed her skirt, and was looking up at him with her long hair trailing behind her on the duvet. Her white vest top remained, then a strip of smooth bare flesh below, ending at the top edge of her green G-string. The triangle of material now lay off-centre, nuzzling against her leg on one side, exposing her pussy. Her lips were puffy, and still met in the middle, forming a neat line - she had obviously never had a cock inside her. Harry drank in the sight of this beautiful girl in her underwear, and felt like the luckiest man alive. Here was a young woman who could have any man she wanted, and she was giving herself to him. More fluid came out of his dick as he sat back on the bed, next to her hips. Chloe's Cherry Chloe grabbed Harry's cock through his boxers. Now free of the jeans, she could feel along the whole length, right to the end. She could feel his balls underneath, and she could feel the soaking wet material where the end had been earlier, and where it was now. It was pressing against the material of the boxers, pushing them out like a tent, and where the end of his cock touched the fabric there was a huge droplet of wet precum that only seemed to be getting larger. She put her thumb in the liquid and moved it around. Now it was Harry's turn to moan. Chloe was touching the most sensitive part of his dick through the wetness and the fabric, and it felt amazing. He hadn't felt this good with a woman touching him for as long as he could remember. "God that feels so nice," he said. They looked at each other and smiled. They were already old friends, even though they had been talking for only a few weeks. Being here, now, felt so right. It felt inevitable, like a force of nature. They were lost in each other now. Harry sat next to Chloe as she played with the end of his dick through the boxers. He started stroking her thighs. The soft young skin felt incredible beneath his fingers. Again he moved upwards and quickly found his way between her pussy lips into her amazing warm wetness. Again he pushed two fingers inside her, and this time she arched her back as she cried out. Then her cry became a moan, and then a sigh. In response, Chloe traced her hand upwards along the material of the boxers to the elastic at the top. She lightly traced along the top of the elastic, caressing the bare skin, and giving Harry goose bumps. Chloe smiled at him mischievously. It was such a turn-on. Harry knew what was coming next, and savoured the anticipation. Chloe's hand dived down inside the elastic and found his dick. With her other hand she pulled the elastic down and his cock was finally free, a sudden coolness hitting it. Harry pushed his fingers deeper than he had before, making Chloe's back arch again, and putting a big smile on her face. Then Chloe started moving her hand up towards the end of his dick, slowly but firmly. Harry held his breath as he knew what was coming. Soon enough, Chloe's fingers reached the bell end and rubbed over his special spot. Harry cried out and his head fell back as his neck muscles disintegrated. This was the most sensitive part of his dick. Chloe had just brushed past it but it was the most intense feeling. Harry responded by pushing his fingers further inside her, and she cried out again. Chloe seemed to enjoy the control she had over him. Playfully, she moved her hand back down over the same area, trying to figure out the exact spot she'd touched. He cried out again as she travelled past it. Up she went again, grinning at him. "Does that feel good?" she asked. Harry could only nod and grin before her hand touched his spot again and he cried out again, no longer in control of his voice. She teased his spot over and over again, until he was bucking with pleasure and moaning constantly. He couldn't even focus on fingering her anymore; she was in control now. Chloe stopped and Harry realized his eyes were closed. He opened them as she grabbed the sides of his boxers and started pulling them down. She giggled as he helped her pull them past his feet, then he turned around suddenly and pushed her flat onto the bed again, to more giggles. "I want to lick your pussy," he said. Chloe writhed on the bed at the idea, and smiled a big happy smile. "OK," she said excitedly. He leaned over Chloe and kissed her on the lips, then the neck, and then he moved his hands to her hips. He felt like a teenager himself. He moved his head close to her body and kissed the lacy material on the front of her G-string. Chloe wriggled. He pushed her thighs apart to make room for his face. He got down and gently kissed her pussy and G-string. Chloe gasped. Harry put his tongue out and gently licked the outside of her pussy lips. She moaned and shuddered. Harry held her hips tightly to stop her from moving. Now he was in control again. He licked up and down the slit between her pussy lips. They were closed together so he was still not tasting her, just teasing her. She writhed on the bed in anticipation. Then, applying just enough pressure, he forced his tongue between her lips, and licked quickly upwards, lapping up her juices. It was the sweetest pussy he'd ever tasted. Chloe moaned loudly, and then squealed and tensed up when he flicked her clit with the end of his tongue. He pulled away and she relaxed and sighed. "Is that good?" he asked, smiling. Chloe nodded and grinned. Harry performed another lick between her pussy lips, from bottom to top, licking her clit and then pulling away again. She moaned and gasped, and this time she arched her back when he touched her button, and collapsed back onto the bed with a sign when he stopped. He repeated this a few times, each time Chloe responded more when he licked her clit, until she was moaning heavily and almost screaming at the end. Harry paused for a second, then Chloe took control again. "Take my panties off," she ordered. Harry grinned at her. On the day he'd declared his feelings for her, Chloe had undressed down to her panties for him on the webcam. As she'd modelled them for him, she'd told him that he could take them off any time he wanted. It seemed so long ago now. He was going to take his time over this. He started by rubbing his finger in her panty crotch again, and pressed inwards, so her G-string rode up between her lips and into her wetness. Then he grabbed the side strings and pulled slowly downwards, teasingly, savouring the feeling of finally removing them. He slowly pulled the waistband over her pussy and down her thighs, while the crotch stayed in place, nestled in her pussy. He slid down further until the crotch came away, a thread of clear wetness connecting it to her pussy for a moment before breaking. She sighed at the feeling, then he pulled the G-string all the way down to her feet and off. He glanced down at it - the inside of the material was white with her fluids - then threw it on the floor. Chloe was now naked from the waist down. Harry could see her pussy in its full glory for the first time. It was completely shaved, and her pussy lips were pink from her arousal, and glistening with her juice. "God you're beautiful," he told her. Harry lowered his face once more to Chloe's pussy. He kissed it again, then pushed his tongue between her lips. Chloe was writhing on the bed and moaning at the touch. He licked around inside her lips, licking her clit, and licking the soft pink parts of her pussy. He teased her hole a little but didn't push his tongue inside just yet, preferring to massage the whole area. The room was filled with Chloe's moans and sighs and cries, a cacophony of lust and desire. He could have stayed here forever. It was a beautiful moment, sexual and loving at the same time. Harry moved his head upwards and kissed Chloe's shaved mound, then her navel. He pushed her vest top up and kissed her stomach. He worked his way up, pushing her vest away as he went, kissing in a line until he reached her bra, then he kissed inside her cleavage, and all over the exposed parts of her breasts. Chloe sat up and removed her top, and then her bra. She was completely naked now. Harry sat up and put his arms around her waist, then bent down and kissed her nipples, flicking them with his tongue and sucking them into his mouth. They got hard instantly. Then Chloe grabbed Harry's T-shirt and pulled it quickly over his head, forcing him to release her. They were both naked now. Naked and ready. A moment passed as they looked at each other. "I think it's time to put that condom on, Harry," she said. This was it. Chloe was ready to lose her virginity. He'd fantasized about it, and then they'd talked about it online, and now it was finally going to happen. He'd wanted it so badly for so long. He'd wanted to make this a night she would never forget. He'd wanted to make it special and amazing and satisfying. This would make it perfect. He was going to make love to her. Right now. He reached down and grabbed the condom from his jeans. He unwrapped it and slipped it over his bell end, then showed Chloe how to smooth it down over the shaft. She did it slowly and seductively, wanking him off slightly as she went. Harry moaned gently as she rolled the condom down bit by bit until she reached the end. Then she lay back on the bed with one arm above her head and the other resting on Harry's knee. Harry shifted Chloe slightly across the bed so she was in the middle, her legs apart. He knelt between her knees and looked down at her, his dick standing to attention, ready for action. "What do you want me to do now, Chloe?" he asked with a smile. "Fuck me, Harry," she said, "I want you to put your dick inside me, right now." This was it, his ultimate fantasy was coming true. His gorgeous teenage friend was lying in front of him, completely naked, and asking him to take her virginity. He leaned forwards over Chloe and held his weight with his left arm. With his right arm he held his condom-covered dick. He gradually edged closer to her, until the end of his dick just touched her pussy. He teased the end up and down between her pussy lips, as he had with his fingers. She shuddered and let out another moan. "Are you ready?" he asked. "More than ready," she smiled back. Harry pushed the end of his dick against Chloe's pussy. The angle was just right - it slid into place right over the entrance. Another centimetre and he would be penetrating her. He hoped it wouldn't hurt her too much. She was as wet as a girl could get, but she was going to be tight. He pushed gently, and met gentle resistance. Chloe held her breath. He pushed a little harder. There was some give, but still resistance. Harry stopped for a minute, with his dick in place, and leaned in to kiss Chloe. He really didn't want to hurt her. They kissed for a minute like old lovers, then pulled apart again. "Do it," she commanded. Harry gulped. He pushed a little harder, then a little harder, then a little harder still. Suddenly he felt the resistance give way with a rip. Chloe screamed at the top of her voice as her pussy opened up, for the first time ever, to allow his dick inside her. The feeling was almost indescribable; Harry felt it in his bones. It was as if everything was stuck together inside her, and he was forcing it apart, almost tearing it open, irreversibly. He was just a centimetre inside her but it was obvious that she would never be the same again. This was a permanent change to her body. She was no longer a virgin. Harry had deflowered Chloe in just a second, and now she was a woman, and they were lovers. "Are you OK?" Harry asked, concerned. Chloe was red in the face and panting. She couldn't smile, there was too much going on for that. She shook her head. "I'm fine," she said. Harry took it slowly. He withdrew and pushed back in, no further than before, playing with the penetration that he'd achieved. The condom meant he couldn't feel Chloe's wetness, but he knew it was there, and he was dipping into it each time. Chloe just breathed deeply, recovering from having her cherry popped. The redness slowly faded from her face. Then she looked at him seriously. No words were needed. Harry withdrew once more and Chloe braced herself. Harry pushed in again hard, forcing entry, and opening her pussy wider and deeper than before. Chloe arched her back and screamed again. It was unsettling, feeling that he was tearing her open and making her scream, but it certainly proved she was a virgin. There was less pain in her face this time, he thought. She looked at him lustfully, and he leant over and kissed her passionately, with his dick still half an inch inside her. They continued kissing while Harry played with the length he'd opened up, pulling in and out slowly so Chloe could feel every movement. She was melting into his kiss now. The pain had passed, and he was giving her pure pleasure. It felt amazing for him too. He couldn't remember ever having a pussy as tight as this. Even with the condom, he could feel it squeezing his dick hard. And the way she was melting into his kiss while he slowly made love to her was deeply satisfying. They held each other tight, their mouths melting together, moaning with lust, as Harry continued slowly fucking her. Every few strokes he'd add a little force and push a little deeper, opening her up a little further. Each time she would shudder in his arms and gasp into his mouth, then melt into his lips again. Eventually the resistance stopped, and he seemed to break through into an opening inside her. He slid an inch further with ease, until he was about halfway inside. He stopped trying to go further, and just fucked her slowly with half his length. Chloe seemed uncomfortable, though. She broke off the kiss. Her face seemed unhappy, somehow. Harry lifted himself with his arms and looked down at her, concerned. "Are you OK?" he asked her. She bit her lip and furrowed her brow, as if considering something, before answering. "Harry, take the condom off." His jaw dropped. "What?!" he asked. "I want you to take the condom off," she repeated. This was not the plan. He was married; having an affair already jeopardized that but getting her pregnant would pretty much end it. It was too risky. "Chloe, I don't want to get you pregnant," he replied. On the other hand, she had a tight little pussy that was soaking wet and he couldn't even feel it properly. He'd been silently cursing the condom since they began. "I won't get pregnant if you don't cum inside me," she said. Harry felt himself being swayed by her logic. "Chloe, you might. I don't want to take that risk." Chloe just looked at him. Her eyes seemed very big all of a sudden, and her face was pleading. He wanted it to be perfect for her, and it was what he really wanted too. It was just the risk. Harry's head was spinning as he searched for a compromise. "Well, look, I'll try not to cum inside you, but if I do, you have to promise to take the morning-after pill, OK?" "I promise," she said, then she reached down and pulled the condom off him and threw it on the floor. The cool air blew against his dick and he felt naked freedom again. It was delicious. He was going to put his dick inside his lover and feel her wetness all over him. And he might get her pregnant. The thought thrilled him. This was a dangerous game now. He knew she didn't have any birth control except the condom. If he came inside her ... The idea spurred him on. It was sexy as hell. Fucking bareback, with all the additional pleasure and all the additional risk it involved. All of a sudden his dick seemed even harder than it was before. Harry moved back into position as Chloe laid back on the bed. Once again he reached down and teased her pussy with the end of his dick. Except, now he could feel her wetness, and she could feel his. It was mind-blowing. Their fluids ran together, soaking her pussy lips as he rubbed her directly with the end of his uncovered dick. Yes, this is what he had really wanted all along. This was the real experience. Tonight was about making love, sharing each other's fluids and bonding with each other in the most intimate way possible. How was it going to feel putting his dick inside Chloe's pussy now? The anticipation was almost unbearable. He manoeuvred again so the end of his dick was pressing against Chloe's entrance. So much wetness. He pushed ever so gently and slid halfway in again with no resistance. He couldn't believe the way her pussy felt inside. It was like a swimming pool, filled with her juice; the end of his dick was completely bathed in warm fluid. He pumped in and out slowly, enjoying every nuanced feeling. Chloe just lay there, writhing gently, and clearly enjoying it as much as he was. They grinned at each other. "God, it feels so good," he said. Chloe smiled back, and nodded as best she could. Harry could have stayed inside Chloe like this forever. He wasn't even close to orgasm yet. The combination of lack of sleep, the lateness of the hour, and the alcohol he'd had tonight, were all helping him to stay in control. And anyway, tonight wasn't about him. It was about Chloe. It was about showing her how amazing sex could be with the right person, and making sure her first time was something she remembered fondly for the rest of her life. He could cum any time. "Let me suck your dick," Chloe said. "OK," Harry laughed, "fine by me!" He popped out of her and sat up beside her. Chloe sat up too, cross-legged. She told Harry to lie down, then got on all fours beside him. She kissed him on the lips, passionately, then started a chain of kisses down his neck, down his chest, across his stomach, and then she kissed the end of his dick. Harry sighed loudly; it felt lovely just to be kissed down there. Then Chloe put her tongue out and licked the end of his dick. That was even better; Harry moaned and more precum dripped out of him. Then she took the end of the dick in her mouth, and closed down around it with her lips. There was nothing Harry could do except moan in appreciation. With his dick in her mouth, Chloe flicked the end with her tongue, making Harry writhe with pleasure. But Harry was feeling restless somehow. He didn't like just sitting there and taking it. "Let's do 69," he said. "Lie down." Chloe lay down on the bed, still completely naked. Her legs were angled apart, and her pussy lips no longer met in the middle. Instead, they gaped open slightly, letting Harry see the pink interior, which was dribbling with her juices. Harry climbed over her on all fours, with his head near her waist. He sat down a little so Chloe could take his dick in her mouth. She closed her lips around it as before and licked the end. Harry leaned down and licked Chloe's pussy between the lips. Harry got in closer and focused on Chloe's clitoris for a while, flicking it with his tongue and then sucking it into his mouth. Meanwhile Chloe was taking more and more of Harry's dick into her mouth, licking all over it. They both moaned continuously. Harry pushed his head further down and licked the opening to Chloe's pussy, savouring the taste once more. Then he stuck his tongue straight out and pushed his head inwards so his tongue penetrated her. Chloe writhed and gave a muffled moan with her mouth full. Harry started fucking Chloe with his tongue, making it as hard as he could. He could really taste her insides now, and it was the best tasting pussy he'd ever had. Chloe continued to writhe, while she moved her head up and down his dick, letting him fuck her mouth while his tongue fucked her. They continued the 69 until Chloe stopped writhing and lay still, slowing her sucking on his dick too. Harry wasn't sure if she'd cummed or if she was just ready for a break. He looked up at her, through the tangle of their bodies. "Do you want some tea?" Chloe asked him. He laughed. "That'd be lovely, actually," he said. They took a toilet break, made some tea, and sat on the back doorstep chatting for a while. Chloe wore a robe and Harry was still naked. "It's funny, you know, most people do all this stuff over several months, but we've done it all in one night. You've fingered me, you've licked me out, we've done 69, we've fucked." "Did you want to take it slower?" Harry asked, suddenly concerned. "No!" she laughed, "I just think it's funny." Harry got the idea she was quite proud of herself. It matched the way he was feeling precisely. He leaned over her and pushed her down onto the floor, pinning her shoulders down with his arms. "Mmm, kinky!" she smiled. Chloe's Cherry He kissed her, hard, and she responded passionately. Harry undid the tie on her robe and reached down and felt between her legs. She was still soaking wet. They continued kissing while he stuck two fingers up inside her pussy, making her moan loudly and arch her back. "Let's go back upstairs," she said. They went up and kissed some more. Chloe caressed Harry's dick, still slippery from his wetness, while Harry fingered her. She was so wet, he tried putting three fingers inside her, and succeeded easily. She moaned loudly at that. Then he got his little finger into position and shoved that inside her as well, for good measure. "How many fingers have you got inside me?" she asked him. "Four," he told her. "Mmm, feels good," she said. Then they were fucking again. It was just like before. Perfect wetness; Harry slid in and out with ease. But he was still only halfway in at most. It was time to show Chloe what the full length of his dick felt like inside her. He pushed but the angle wasn't quite right to get further inside her. "Put your legs up", he told her. Chloe raised her legs and rested them on Harry's shoulders. Now he could really thrust into her. Harry pushed; there was still quite some resistance. He started fucking Chloe faster, getting some momentum. Chloe was shuddering by now at the speed and intensity of Harry's fucking, and she couldn't stop moaning with pleasure. Harry decided it was time to go further. He took a big plunge into Chloe and put more force behind it. Chloe's pussy stretched once more and she screamed. Harry kept the rhythm up and pushed hard on the next stroke, too. Chloe screamed again. He fucked her harder and harder on every stroke, trying to ram his dick all the way inside her. Each time her pussy opened deeper for him, and each time she screamed at the top of her voice. The only thing on his mind now was to fill her with his cock, to let her feel the whole thing inside her, to give her a proper fucking. Soon Harry was pulling his dick slowly the whole way out, to let her breath, and then ramming it inside her as hard as he could, forcing his way through the last untouched parts of her virgin pussy, and making her scream every single time. He didn't know if the screams were pain or pleasure, but they were turning him on immensely. Soon Harry was fully inside her, and grinding against her pussy on each stroke. He wasn't opening her up any more, but she was still screaming every time he rammed his dick into her, and she was so tight he had to use some force anyway. He kept up the rhythm without respite, sliding out slowly until his dick was only resting at her entrance, pausing for effect, and then suddenly ramming himself inside her as hard as he could. Chloe screamed and screamed, completely driven by lust. Her face was getting redder, her skin was hot where he held her, and she was breathing fast. Again and again he pounded her pussy. Her screams changed tone slightly; she sounded like she might die from the fucking she was getting. Then she gave one long scream and stopped. Her face was bright red and she was panting, and she looked like she was trying to say something. Harry looked at her quizzically while she got her breath back enough to say it. "I think I just came." Harry grinned. His job was done. Chloe had given him her virginity, and he had taken it well - carefully and lovingly. And he'd given her an orgasm; the first orgasm she'd ever received from a man. Harry couldn't imagine how a young woman's first sexual experience could be any better than that. He was very proud of himself. "How was that?" Harry asked. Chloe couldn't speak again for a minute. She fanned her face with her hand, and hyperventilated slightly. Then she grabbed him around the neck and pulled him towards her. "That was amazing," she said, and snogged his face off. Harry pulled away after a minute. "I love you," he said. "I love you more," Chloe joked, and snogged his face off again. Then she looked at him. "Now I'm gonna make you come." After the screaming, which turned him on more than he would have ever guessed, Harry was already very close. He let Chloe lie back while he propped himself up with his arms, and started fucking her slowly. He was doing it for himself, now; it was his reward for getting her off. He chose a rhythm that would make him cum quickly, and relaxed the pace and force of his thrusts. It was a very gentle fuck now, slower and less insistent than before, but designed to stimulate his special spot as much as he could. Chloe was tight and her insides rubbed insistently against his cock, so it wasn't long before he could feel his orgasm approaching. "I'm really close," he said, pulling out of her. "What are you doing?" Chloe asked. "Wank me off babe, I'm ready to cum." Then he got his second surprise of the night. "I want you to cum inside me," Chloe declared. "What?! No! Just wank me off," he protested. He couldn't believe his ears. Was she serious? He tried to guide her hand to his dick, but she wouldn't let him. "Cum inside me, please, Harry, I want to feel what it's like. Please?" Harry had no resistance left. He urgently needed to cum. He thought about doing it himself, but he couldn't help being completely turned on by this gorgeous schoolgirl begging him to cum inside her. She'd melted him. The idea of squirting his sperm into her unprotected pussy melted him too. It would be fine, as long as ... "But you are going to have to take that morning-after pill tomorrow, OK?" "Yes, I'll get it as soon as the pharmacy opens, I promise." She pulled him down and kissed him passionately. "Now squirt your cum in me," she said, guiding his dick back inside her with her hand. Harry fucked her as slowly as he possibly could, savouring every last moment of the sex, holding her close and kissing her neck, telling her how much he loved her, running his hand through her hair. He revelled in the feeling of her soaking wet pussy around his dick as he felt the orgasm building inside him. He delighted in the fact he'd just taken her virginity, making her cum in the process. He started shaking uncontrollably. He slowed down even more, to make it last. His fantasies - fantasies he'd had for months - had all come true, tonight. His orgasm was building to the point of no return now. He lifted his head and looked at his young lover. She was lying there, wide-eyed and smiling, looking as sexy as she ever had, and happier than he'd ever seen anyone. "Cum for me, babe," she said, and she squeezed his dick with her pussy and pulled him down and kissed him. He pushed his dick inside her as far as it would go and she arched her back and cried out again. He was so, so turned on. The cum was boiling in him. The end of his dick was on fire. So close now. He pulled his dick nearly the whole way out, then he felt her squeeze the end with her pussy and it pushed him over the edge. This was it. He was there now; he could feel it rising inside him. If he wanted to pull out, now would be the time to do it. "I love you," he told her, studying her face and gazing deeply into her eyes. In that moment, he realized that he couldn't rely on her taking the morning-after pill. There would be some excuse, some reason, but she wouldn't take it. Deep down, they both knew why she wanted him to do this. And, deep down, he knew that they both wanted the same thing in the end. Harry and Chloe. In love. Together. Now he had an opportunity to seal that forever. With one final decisive stroke, he shoved his dick all the way into the teenager's soaking wet pussy and came violently inside her, splattering his semen right through her unprotected cervix and into her young fertile womb. He screamed her name as he felt it shoot out of him, and Chloe cried out in ecstasy as she felt something like lava splashing against her insides for the first time in her life. He squirted and thrusted into her, over and over again, holding her body tightly to his as he shuddered and spurted his orgasm inside her while she screamed with delight. There was so much, it never seemed to end. So much teasing and so much phone sex and cam sex so that finally he had a ton of it waiting just for Chloe. He couldn't stop it now, even if he wanted to. He was overwhelmed by the desire to impregnate her, deliberately and uncontrollably sending load after load right into the heart of the schoolgirl's unguarded reproductive system while she moaned her heart out in blissful appreciation. She'd begged him for it, begged him to let her feel his cum inside her, and he'd given it to her in abundance. Now she was filled to overflowing with his hot sticky semen, and there was nothing anyone could do about it. Not his wife, not Chloe's mum - nobody. He felt himself tense again at the thought of it, and he helplessly pumped the last of his seed deep inside her receptive teenage body. As the last remnants of his orgasm died out, they both collapsed in a hot sweaty hug, still joined by penetration, and completely spent for the night. They were in heaven. They'd consummated their affair, and Chloe was now Harry's mistress. They belonged to each other now. There was no going back. Nobody could undo what they had just done. They bathed in the joy of it all. There was nothing to say. No words could touch this. They just looked into each other's eyes, until the sun streaming through the window indicated that it was morning, and it was time to face the rest of their lives, together.