Chloe's New Boarding School

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Young girl tries to fit in to new school.
4.8k words
4.75
28.4k
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Part 1 of the 2 part series

Updated 02/16/2024
Created 01/04/2023
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Chloe decided that she hated boarding school. Her father had been promoted at work, which required a two-year stay in Hong Kong. They had tried Chloe in a school there, but after a term, had become very dissatisfied with the education system. Reluctantly the family agreed that she should come back to England to finish her school education. Chloe was eighteen, and needed to complete the last year of A-levels to secure a place at a good university.

Marymount Girls' School was very nice, and the teachers were excellent, but Chloe missed her friends dearly. She had been at Marymount for a whole month now, and hardly anyone had spoken to her. They had been very kind of course, and explained all the eccentric boarding school rules to her, and occasionally chatted to her at meal times or as the girls walked across the grounds from the hostels to the school itself - but there was no one that she could call her friend.

She longed for a real companion, someone to whom she could really talk to, and confide in - someone who would come across to her bed after lights out as she had seen the other girls do in the dormitory, and who would perch on the side of her bed and whisper secrets and giggle together. Nearly all the girls had such a friend, and Chloe could hear them laughing and talking softly to each other until quite late at night. In fact, it was only when the prefect came up to bed that everyone settled down and went to sleep.

Chloe was both afraid of the prefect and in awe of her. Her name was Alison Moncrief - she was a tall, slender girl who carried herself with great dignity. She was practically the same age as Chloe, but was very mature for her age, and could easily have been mistaken for one of the younger teachers. She made Chloe feel inadequate and completely inferior and insignificant. To start with she was frighteningly clever - she had won a scholarship to Marymount, and was destined to go to either Oxford or Cambridge.

She was also very attractive, and she knew it. Her long dark hair fell in waves across her shoulders when she wore it loose, perfectly framing a stunningly beautiful face - if you caught her gaze, her green eyes seemed to burn into you. Alison's complexion was perfect and her flawless white skin made her full lips look as if she permanently wore lipstick, though of course, wearing make-up was forbidden at the school. A slender straight nose, cheekbones to die for and a heart-shaped jawline all contributed to Alison being arguably the most beautiful girl in the sixth form.

There were ten beds in the dormitory, in two rows of five, and because she was the prefect, Alison had an adjoining room to herself, with her own dressing table and wardrobe. The other girls had to make do with shared chests of drawers and footlockers by each bed. As the newest girl in the dormitory, Chloe had been made to take the bed nearest to Alison's room. The established girls preferred to be further away, so that they could get up to more mischief, although Alison was so strict that nothing more wicked than creeping over to another girl's bed to sit and gossip ever occurred.

Chloe was fascinated by Alison. A prefect could stay working in her study much later than the other girls, who had to have lights out at ten, and each night Chloe lay on her bed, pretending to be asleep when the prefect came up to bed, afraid that she would get into trouble if it were discovered that she was still awake.

Alison seldom closed the door to her room so that she could monitor what the girls were doing, and each night Chloe watched intently as Alison sat in front of her mirror to perform her nightly routine. Alison would undo her hair which often hung in a long plait down her back, and brush it with sweeping strokes of her graceful arms, swaying from one side to the other as she did so. Then she would stand and undress. The regulation white shirt and grey skirt would be carefully removed, and standing only in her bra and panties, Alison would carefully fold away her clothes. Chloe would stare at her gently rounded breasts held in a variety of sexy bras. Some were frilled and lacy, others of sheer fabric and almost transparent. School rules did not allow such underwear. There were several male teachers on the staff, and it would be unseemly if the girls were provocatively dressed. Alison, for some reason, seemed to have special dispensation.

Chloe marvelled at her slender waist, the curve of her hips and her long, slim legs. Alison was Captain of both the hockey and the netball teams, and she excelled in almost every sport. An energetic sports routine kept her figure toned and slim, and when she performed rhythmic gymnastics in a tight leotard, she had everyone's gaze fixed on her, both male and female.

Chloe would wait with bated breath as Alison removed her underwear, and then, quite naked, she would reach under her pillow for her nightdress. As she leaned forward to pick it up, her breasts swayed, and the arch of her back above her beautifully rounded bottom always took Chloe's breath away.

Then Alison would slip the nightdress on, climb into bed, and turn off her light.

Chloe always felt guilty watching Alison's bedtime ritual. Exactly why, she could not quite say. But she never stopped watching. She wished that her own body were as lovely as Alison's, but it wasn't and Chloe felt sure that it never would be. Chloe's breasts disappointed her - she was not nearly as developed as Alison. Alison appeared to have a more mature woman's breasts, whereas Chloe had started to develop breasts very late.

At first, it seemed that only her nipples and areolae were growing, forming two prominent little peaks on her chest. She was delighted when eventually her breasts began to form, swelling beneath the areolae and nipples until Chloe had two hemispherical little breasts surmounted by rounded areolae and nipples. The way her areolae swelled and protruded from her breasts embarrassed Chloe - none of the other girls appeared to be like that.

Chloe was short, not much more than five feet tall, and although her waist was narrow, her hips seemed to her to be a bit boyish - she so envied Alison's hourglass figure. Whenever Alison turned to face her, Chloe would look at her flat stomach and the alluring dark triangular patch of hair, that formed a 'V' shape as if to say 'guess what I have down there'.

Chloe had pubic hair that was fair and seemed wispy and sparse compared to Alison - again she considered it to be a feature that was not at all womanly.

One night, Alison was particularly late in coming up to bed and Chloe lay waiting impatiently. She realised that it had become part of her routine to watch Alison, and if the prefect was late Chloe could never just close her eyes and sleep - she had to stay awake for Alison. Chloe thought that perhaps it was because she missed her mother, and needed the assurance that someone in authority was nearby - Alison's close presence to her bed was somehow reassuring.

All the other girls had long since fallen asleep. Chloe tried to sleep but tossed and turned - it was impossible. At last, she heard Alison come into the dormitory and enter her room. Chloe peered through half closed eyes as she lay quite still, watching Alison pursue her nightly routine. Each step was exactly the same as before, until at last Alison stood robed in her nightie and ready to climb into bed.

But then Alison paused, and came out of her room, and walked slowly down the dorm between the beds, as if she was counting the girls and making sure they were all there. Chloe shut her eyes tight, pretending to be asleep.

She could hear Alison's soft footsteps returning, and was surprised when the footsteps seemed to stop by her bed, instead of continuing into her room. Chloe open her eyes a little, and Allison moved silently to the side of her bed.

Chloe was terrified to hear the girl whisper, "Why do you watch me so each night?"

Chloe was too panic-stricken to answer but lay still with eyes tightly shut, still pretending to be asleep. Alison repeated the question, this time bending over Chloe - looming over her. There was no escape, and Chloe whispered back, "Because I can't sleep."

Chloe felt as if she was dreaming as she heard herself continue:

"And because I think you are beautiful. I like watching you."

The realisation of what she had said dawned on her.

"Oh my God," she thought, "why did I say that?"

To her surprise, Alison did not reply but instead sat on Chloe's bed, just where the cover folded down. Talking softly, she asked Chloe various questions about her home, and how she was settling down in the hostel, all of which Chloe answered in eager whispers. At last, someone was showing an interest in her. Her excitement rose and her voice grew louder. Alison put a finger over her lips.

"Ssssh, we can't talk here," Alison whispered, "we will wake the girls. Come to my room, but be quiet."

Chloe followed Alison and tiptoed into her room. Alison quietly closed the door behind her.

"Sit on my bed," she said.

Alison sat beside her and asked a few more questions. Chloe revealed that she was homesick and had not made any friends yet, and Alison put a comforting arm around her. As they talked Chloe felt Alison's smooth fingers lightly brushing her shoulders and upper arms. She was cool and fragrant and Chloe was overwhelmed. Her heart leapt with joy, and butterflies flitted about in her stomach, such was her excitement. Even when the conversation slowly dwindled, Alison continued stroking Chloe's arms. Slowly her fingers moved down the inside of Chloe's arm, and the backs of her fingers brushed softly against her right breast. Was it an accident? It happened again, while Alison looked into Chloe's eyes. It was on purpose!

Chloe felt as if she was dissolving as Alison calmly placed her hand directly over Chloe's breast - over her nipple, which had been poking her nightie into a prominent little peak.

Chloe's throat was closing, and her body began to tingle. She felt her heart pounding in her chest - what was happening?

Alison's fingers deftly untied the little bow that held the top of the nightie closed, and she slipped her hand inside. Chloe shivered, both in fear and delight as she felt Alison gently cupping her breast. She did not know what to do, or how to respond. The touch was warm and soft and felt comforting, but also thrilling.

Alison pulled the nightdress from Chloe's shoulders, and skipped it down her arms. Chloe's breasts were totally exposed, rising and falling with her rapid breathing.

"You are beautiful," Alison whispered, and stroked Chloe's breasts - her fingertips gliding over the upper slopes, down over the pointed tips, and Chloe looked down to watch as her nipples instantly puckered and stood erect under Alison's soft caresses.

"I love your nipples," Alison whispered, "so proud and defiant - they demand to be touched."

Chloe felt imprisoned by her nightie and slipped her arms out, so that the nightie fell to her waist. With her arms now free, Alison picked up Chloe's hand and placed it on her chest. Chloe flinched.

"Don't be afraid," Alison whispered, "if I am touching you, then you can touch me."

Chloe moved her hand over the beautifully rounded breasts, feeling their fullness, and even through the silky nightdress she could feel that Alison's nipples were much larger than hers, and they seemed firm and erect.

As Chloe stroked and fondled Alison's breasts, Alison reached out a hand and placed it on Chloe's cheek. She looked into her eyes and then bent forward and gently kissed her. Chloe felt the touch of Alison's full lips on hers and her heart melted. Instinctively she parted her lips and returned the kiss, and trembled as the tip of Alison's tongue slid softly and wetly into her mouth.

It was so wicked to kiss a girl, but it felt wonderful and thrilling. Their tongues met, flickered lightly one against the other in a little dance and then Alison's tongue dipped deeper. Chloe had no experience in kissing, but she did what came naturally - she sucked the tip of Alison's tongue, and was delighted when Alison moaned with pleasure.

Something was happening to Chloe that she had never experienced before. There was a sensation growing in her, deep in her stomach, and between her legs there was a persistent tingling and it felt as if she was getting very wet. She had touched herself down there on a few occasions, and had felt a wetness develop - it had felt very pleasant, but this was on another level entirely.

As Alison kissed her, Chloe became aware that Alison was undoing her own night dress. She opened her eyes to the glorious sight of Alison's beautiful breasts before her, full and round. She had only caught fleeting glimpses before, and the sight of them now so close and easily within her reach almost made her gasp out loud.

Alison was blessed with beautiful breasts - breasts that any swimsuit model would have died for. They jutted proudly from her chest, appearing to defy gravity - there was no need of a bra to provide uplift.

Alison's areolae were large, and a deep pink colour, in vivid contrast to the perfect milk-white skin that surrounded them. As Chloe had suspected from her first touches through the nightie, Alison's nipples were long and firm, far more suited to a woman than a young schoolgirl.

Mesmerised, Chloe reached out and touched a nipple, tentatively at first, and when Alison sighed and closed her eyes, Chloe grew more confident. She placed her hand firmly over Alison's breast, feeling the long, firm nipple pressing into her palm.

The tingling between her legs surged in intensity. Chloe placed both hands on Alison's breasts, fondling, squeezing and stroking, like an excited child playing with new toys. She looked up to see that Alison was looking at her, an amused smile on her lips. Chloe's fingertips alighted on both nipples, squeezed them, pulled on them - she marvelled at how wonderful they felt as they stiffened under her touch. She ached to take one into her mouth but was nervous. Dare she do it?

Chloe bent her head and kissed Alison's right nipple. Alison sighed contentedly, and dizzy with excitement, Chloe took it into her mouth. Oh yes! It felt so comforting, and yet so exciting. She sucked on the nipple, feeling it swell in her mouth.

The effect on Alison was electric and she quickly stood up.

"What have I done?" thought Chloe, "I've ruined it!"

But far from it; Alison quickly took her nightie off and it fell to the floor.

"Stand up," she instructed and as soon as Chloe was standing Alison pulled her nightie down and it too, fell to the floor. The girls stood facing each other, completely naked. Chloe froze, but Alison calmly pushed her towards the bed.

"Lie, down," she said.

Chloe did as she was told and Alison lay beside her. She bent over Chloe, took her breasts in her hand and offered a voluptuous nipple to the girl's eager lips. Chloe suckled on the delicious teat, and her heart leapt as her sucking drew soft moans of pleasure from Alison.

As she kissed and sucked on one nipple, Chloe fondled the other. All her cares and worries evaporated, and she felt transported into a blissful new world.

Suddenly Chloe felt Alison's hand stroking her stomach, and sliding down to her thigh. The touch was blissful and when Alison's fingertips slid through the soft hair over her mound she shivered with delight.

Alison's long, slender fingers traversed down Chloe's thigh, and then back up, and each time they made contact with Chloe's pubic hair a tremor ran through her. Chloe was now certain that she was very wet - she could actually feel moisture trickling down between her legs. As Alison's fingers caressed her, Chloe's thighs instinctively drifted apart. The caresses were lovely, but now she yearned for an even more intimate touch. Chloe unconsciously flexed her hips, trying to rise up and meet the touch that she so desperately hoped would come.

Alison broke away from the kiss and sat up. The sudden movement made her nipple pop out of Chloe's mouth with an audible plop. She looked down at Chloe, who was panting softly.

Alison smiled and gently put a hand directly between Chloe's legs, cupping it firmly over her mound. Chloe's eyes opened wide - nobody had ever touched her down there!

Alison pressed her fingers down, compressing the soft, moist lips - the touch inflamed Chloe and she gasped. Gently Alison lifted her hand, but her fingertips lingered, and then slowly began to explore, sliding up and down the tender lips, and then gently parting them. Chloe's whole body was trembling, and when Alison's fingertip dipped softly into the wet mouth between the lips she whimpered.

"Ssssh," Alison whispered, as her finger slipped deeper, and deeper still, until Chloe was writhing on the bed, desperately trying not to groan and cry out with pleasure.

Alison withdrew her finger and slid it upwards - up to the point where the lips met, and pressed softly against the little bud that nestled there under its soft folds. Chloe felt the thrill surging, and when Alison began to rhythmically rub her swelling clitoris she thought she would surely pass out, so intense was the sensation.

As Alison lay on her side beside Chloe, she crooked her leg and raised it. She removed her finger from Chloe's clitoris, took Chloe's hand, and pulled it towards her, placing it between her legs. Chloe encountered full, ripe lips, and was delighted to feel that Alison was just as wet as she was, if not more so. Chloe's fingertips slipped easily between the lips, and as Alison had done to her, she explored lower and probed with her finger, feeling for the secret entrance.

The moist silky aperture yielded and her finger slid effortlessly into the hot enveloping sheath. Alison pushed her finger into Chloe again, and moved it purposefully in and out, and then introduced a second finger.

"Do me like this," she whispered, and Chloe inserted another finger, and copied Alison's movements. They stared into each other's eyes as their fingers moved in perfect synchrony, watching the subtle changes in their facial expression as ripples of pleasure ran through them both.

Chloe felt that she could keep doing this forever - feeling such wonderfully thrilling pleasure between her legs was intoxicating, and listening to Alison's soft sighs and moans as she responded to her thrusting fingers was divine. Realising that she could give as much pleasure as she was receiving was truly exhilarating.

Alison started to do something different - while two fingers were deep inside Chloe, her thumb felt for the round nub of her clitoris, and when she located it she started to rotate her thumb over it - round and round, while simultaneously her fingers plunged in and out. It was pure bliss, and Chloe arched her back as enhanced waves of pleasure rippled through her.

"Do it to me," Alison whispered in her ear.

Chloe was no expert, and fumbled a little as she tried to comply. Fortunately, Alison's clitoris was considerably bigger than hers, and easy to find. It seemed very swollen and unencumbered by protective folds. Chloe placed her thumb over it and rubbed, and tried to thrust her fingers in and out as Alison was doing to her. After a few false starts, she soon got the feel of it, and when she developed a steady rhythm she could feel Alison's tight flesh clasping her fingers, throbbing and pulsing around them.

"Perfect," Alison sighed, "that's heavenly! Doesn't it feel good?"

Chloe was not sure if Alison was referring to the rippling pulsations her wet flesh was making on Chloe's fingers, or the thrill Alison was invoking deep inside Chloe - but both felt delectable in the extreme.

"Oh, yes," she murmured," it's incredible!"

Alison kissed her again, soft and tender kisses, lightly brushing her lips over Chloe's, and her tongue dipped once more into her mouth. Chloe moaned into Alison's mouth as delicious thrills coursed through her body.

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