Chloe's Cherry

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.