Another Year at St Cat’s Ch. 07

Challenging Times

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Friday, 5 June

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Fay re-read the words on her screen with a heady mixture of excitement and anxiety. Up until now, his challenges had stretched her inhibitions a little without demanding anything that made her really uncomfortable, but this seemed to be in a whole other league. She still wasn't entirely sure she was doing the right thing, everybody knew the dangers of talking to strangers on the internet. On the other hand, it did seem to be helping her with her problem.

It's something she'd struggled with as long as she could remember. Perhaps it was to do with her childhood. She was the middle child of a large family; she had two younger sisters and two older brothers.

Her parents were very loving, very happy together, and not shy about showing their affection for one another. Fay still blushed at the memory of walking in on them in the kitchen one day after leaving school early and finding them expressing their love for each other in a very explicit way. She could still feel the hot flush of embarrassment as she bolted upstairs, her feet thumping on the stairs. Their 'hands on' behaviour had had quite an effect on her; instead of making her feel more liberated it had had the opposite effect, making her feel quite reticent, almost prudish, about sex and nudity.

She would have been sprinting upstairs to the bedroom she shared with her sister. A bedroom they'd shared until she was fourteen. She'd shared a bedroom virtually all of her eighteen years, and perhaps this was another reason she had a problem with pleasuring herself. It simply wasn't something she had a lot of experience with.

At least she had the dorm to herself at the moment. Both Macy and Miss Brittan, the art teacher, had been suspended until the end of term after what the headmaster had called 'the incident in the art room'. As much as she enjoyed the freedom of having the room all to herself, her inability to fully satisfy herself made her feel like it was an opportunity wasted.

Her ex-boyfriend hadn't been any help either. She shuddered when she thought of the last time she'd seen him, at Easter and they'd made love. Well, the truth was, they'd attempted to make love but he'd finished way too soon. Almost as soon as he'd entered her he'd uttered a strangled gasp, his body jerking wildly, as she felt his hot juices draining from his body along with all his passion and enthusiasm.

"Never mind, sweetie," she'd whispered, as he collapsed heavily on top of her.

Around that time, she'd discovered some very informative websites, and it no longer seemed normal to have a boyfriend who wasn't interested in her pleasure. Having an orgasm once or twice a year no longer seemed so normal. She dumped him a few days later, just before she came back to St Catherine's, using the excuse that having a long distance relationship wasn't working for her.

Still, dumping her boyfriend gave her one less person to confide in and her problem was such a difficult thing to talk about. Who could you ask about something like that? Certainly not your parents or your doctor. And how could she raise it with her roommate Macy? "By the way Macy, I've been having problems achieving orgasm when I'm masturbating, have you got any tips?" Yeah, right.

Ironically, Macy would probably be able to offer some good advice, she certainly had a lot of experience in that area. Fay sometimes heard her, in the still darkness of the night, touching herself. The subtle rhythmic motion of her hands beneath the thin sheet, her flushed face pressed tightly into her pillow to muffle the sounds of her pleasure. Fay always lay still, pretending to be asleep as her friend gasped and wriggled, feeling jealous of her friend's evident enjoyment. Her emotions a strange mixture of arousal and frustration as she listened to her friend's breathing becoming more and more laboured, the soft, yearning sighs becoming hot, feverish sobs as her friend stroked herself towards yet another orgasm. Her passionate moans becoming gradually more and more urgent until she came, a few tense seconds of silence followed by a long, low moan of sublime contentment.

Eventually, frustrated at her inability to find a solution, Fay had started to seriously research her issue on the internet. Before that, she'd just surfed websites and lurked, invisible, in chat-rooms trying to pick up tips on how to achieve that elusive orgasm. But nothing had seemed to help, and she'd got more and more involved, eventually plucking up the courage to chat to someone: "Neal25".

They'd started to play an online game of "truth or dare". Fay usually went for "truth", wanting to know more about the man she was chatting to and had found out that he was a 25 year old teacher, originally from London. Conversely, he usually went for "dare" and had set her a number of increasingly risky, and sexual challenges.

She'd completed her latest 'dare' today. She could remember exactly what he'd written, word for dangerously exciting word: "I want you to go all day without wearing knickers. To make this more difficult, you are to wear a dress or skirt. The thrill here is being naughty. Bad. Risky. Someone might see. All day, I want you to think about how bad you're being. Come on frustratedGrl, I dare you!"

The plaid uniform skirt that they were required to wear in the summer months only came down to her mid-thigh and so she'd spent all day self-consciously tugging it down to her knees especially when she was climbing stairs, and crossing her legs so tightly that her legs had gone numb. It had been a bright and breezy kind of day outside and she'd been able to feel the fresh air flowing around her bare thighs, a constant reminder of her nakedness. Knowing that if the breeze caught her skirt just right it could fly up, exposing her as the wanton girl she was. It had made her feel every bit as naughty as he'd predicted.

Of course, when she logged on later that evening, 'Neal25' was very keen to find out all about her day. She smiled when she read his words, it was pretty clear how keen he was to hear about her day.

Neal25: how did you get on, frustratedGrl? did you complete the dare? how did it feel?

frustratedGrl: yes! :-) it made me feel naughty and bad and scared, all at the same time. at lunchtime, the canteen was packed. waiting in line one of the male teachers pressed up against me and i couldn't help wondering how he'd react if he knew my little secret! i went bright red :-o

Neal25: what a naughty girl you are! did it turn you on?

frustratedGrl: i just felt too nervous today; i guess i feel a little aroused when i think about it now

Neal25: you're so hot! so it's your turn, truth or dare?

frustratedGrl: hmm, i think... truth

Neal25: ask your question then....

frustratedGrl: does hearing about my day arouse you? are you hard? :-o

Neal25: oh yes, very

frustratedGrl: wish i could see! are you touching yourself?

Neal25: a little, are you?

frustratedGrl: maybe a little :-)

Neal25: i'd love to find out more but i've got to go soon and now it's my turn

frustratedGrl: aw, i was just starting to have fun! truth or dare?

Neal25: i dare you to take a naughty picture of yourself outside. it could be topless or completely nude or maybe just wearing a see-through top. it doesn't matter as long as you feel out of your comfort zone. it can be anywhere outside: in a field, in some woods, down an alley. you need to send it to me, i'll explain how tomorrow. i don't need to see your face, it's best if we both remain anonymous so wear a mask, a big sunhat, or just crop the picture

frustratedGrl: you seem to have given this a lot of thought! when do i get to see a picture of you?

Neal25: when it's your turn! you can dare me whatever you like

frustratedGrl: hmm, outside, really? i'll try but i'm not sure i can, what if someone sees me?

Neal25: well that's what makes it risky; it wouldn't be a much of a dare if it was easy

frustratedGrl: ok, i'll try, but no promises...

Neal25: can't wait!

**session ended 22:14:12**

Fay closed the laptop and got into bed. How on earth was she going to do this? Tomorrow was Saturday, which gave her the opportunity to go somewhere, but realistically it would have to be within walking distance of the school. There were some secluded spots along the river, up towards the reservoir. Eventually she drifted off to asleep, still pondering her options.

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Saturday (Morning), 6 June

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Major Farnsworth hiked along the path through the trees. He walked steadily feeling the rhythmic thump of his camera and binoculars bumping against his chest through his waxed jacket. His black Labrador, Betsy, trotted along behind him faithfully. After his wife had died, he'd got into the habit of taking long early morning walks before breakfast. This route was one of his favourites: a hilly, three mile loop starting from his cottage at the edge of the village of Eastbrook, up through the woods, and back along the river near St Catherine's school. Although he'd been retired for many years now, he still got up at six am every day, the habits formed by a lifetime in the army hard to shake off.

He'd found that this quiet part of the day, just after the dawn chorus was best time to spot birds. After he'd retired, his wife had encouraged him to find a hobby that kept him outdoors and active, and bird-watching allowed him to use the skills of camouflage and moving around unseen that he'd built up over his years in the forces. Today he was hoping to spot a desert wheatear; a friend at the local bird-watching club had sworn he'd seen the rare bird somewhere down here near the river (although he didn't get a photo), so he was walking along the ridge and keeping an eye out for its distinctive sandy brown plumage. So far he hadn't seen much. Some blurred pictures of a barn owl and greater spotted woodpecker wouldn't impress anybody down at the Eastbrook Bird-spotters Club.

He paused when he spotted movement: something pink and white among the dull greens and muddy browns of the forest, in a patch of sunlight down in the reeds and tall grasses near the river's edge. Something almost luminescent in the early morning sunshine. Was that a person? The major held the binoculars up to his eyes, leaning against a thick oak tree to steady himself.

It was a teenage girl! In his experience, it was unusual to see a teenager up and around at this time of the morning. She was looking around nervously, it looked like she was making sure she was alone. He waited patiently as she had a good look around then quickly unbuttoned her jeans and sat down on a picnic bench, slipping off her trainers then easing the tight denim from her slender legs.

"Good grief, I think she's undressing, Betsy!" he muttered as he slipped behind a tree trunk, his years of army training kicking in as he blended into the shadows in his dull olive jacket and brown cords.

He wondered where she'd come from and what on earth she was up to. The first question was probably the easiest. She looked about eighteen or nineteen so she was probably from St Catherine's, the school about a mile downstream. He pondered the second question as he watched her unbuttoning her white blouse and sliding it over her pale shoulders. Was she sunbathing, or about to go for a swim? He'd heard a lot of rumours about the school. Was it was some kind of bizarre initiation ceremony?

Whatever the reason, he wasn't complaining. He had an excellent view of her through his powerful ex-army binoculars, feeling a warm surge of arousal as he realised she wasn't wearing a bra under her blouse. She was a pretty young thing with long, dark, silky hair and a pleasing, almost classically beautiful face with high cheekbones and plump lips. Her body was slim with sleek, firm breasts sitting high on her chest. His hands trembled a little as he watched her holding her mobile phone out in front of her, obviously taking pictures of herself clad in just a tiny pair of white knickers. What did the youngsters call them? Selfies? Perhaps she was taking pictures for her boyfriend. If so, he was a very lucky young man.

He watched intently as she put the 'phone down on the table and glanced around anxiously. She looked ready to bolt at the slightest noise, like a young deer grazing out in the open, wary of predators. He felt his cock stirring into life as he watched her hook her thumbs under the waistband of her panties. He slipped further behind the tree as her head swivelled in his direction, although she'd be unlikely to spot him at this distance. It gave him the opportunity to put down his binoculars and grab his camera. He had a high power telephoto lens, ideal for capturing images of rare and exotic birds, and he'd rarely seen anything more exotic than this mysterious girl. Peering through the viewfinder he was rewarded with the glorious sight of her leaning against the bench with one hand, whilst slipping her last item of clothing off of her lean legs, revealing an almost bare pussy, just a thin landing strip of dark hair. He watched her lift each foot in turn then toss the little tangle of white onto the weathered wooden table along with the rest of her clothes, a little crumpled pile of indigo and white. He felt himself quickly become fully hard, the little major in his trousers saluting the sight of her gorgeous naked body glowing palely in the morning sunshine as he snapped away happily.

He zoomed in a little more and held his breath, drinking in the unexpected vision of her firm, young curves as she once again held up her phone at arm's length, taking more pictures of herself as he took pictures of her. No makeup or jewellery, just a natural beauty against the backdrop of the English countryside.

After quickly snapping a couple of photo's she was finished. He couldn't suppress a soft groan of disappointment as she hurriedly started to pull her clothes back on, the show over for today. He only had the chance to take a couple of pictures of her quickly buttoning her blouse and pulling on her jeans before she finished dressing and was slipping her shoes back on. He watched her scurry away down the riverside path in the direction of the school, unwilling to move on until her white blouse completely disappeared behind the bushes and reeds.

"Well, Betsy, that certainly beats seeing a desert wheatear " he said, already looking forward to downloading his pictures and examining them in all their high definition glory on his laptop.

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Saturday (Night)

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Fay sat on her bed cross-legged, just the glow from the laptop's screen lighting her face. She chewed her fingernail as she examined the images she'd downloaded from her mobile trying to decide which ones to send him. Not the ones that had captured the bottom half of her face or that distinctive diamond-shaped birthmark on her left shoulder. Eventually she selected the two where she was just wearing her knickers, the early morning sunlight slanting across her naked boobs. She bit her lip nervously as she hit the Send button.

frustratedGrl: do you like them?

Neal25: very much, they're very sexy pictures; how did it make you feel?

frustratedGrl: nervous, liberated, decadent, i was covered in goose-bumps! i'm not sure whether it was the cold or the excitement!

Neal25: excellent, well congrat's on completing the dare!

frustratedGrl: my turn! my turn‼

Neal25: OK, truth or dare?

frustratedGrl: i think it's time i got to see a picture of you ;-) i dare you to send me one

Neal25: maybe, but i can't show my face, you know the rules are that we both remain anonymous

frustratedGrl: it's not your face i want to see :-)) come on, you've seen me

Neal25: ok.... wait a minute...

Whilst she waited, Fay changed position, stretching her long legs and lying on her side, and using a stack of pillows to support her head. She unbuttoned her blouse and caressed her boobs, squeezing the firm, springy flesh beneath her thin bra. As she re-read the text, she started to absent-mindedly stroke the pale, silky skin of her thighs beneath her plaid skirt as she impatiently pecked at the laptop's keyboard with the other hand.

frustratedGrl: come on! you're not shy, are you? :-p

Neal25: ok, here you go...

Fay double-clicked the thumbnail with trembling fingers and caught her breath at the image that filled the screen. It was a dim, low-resolution black-and-white image of a young man seated in a large, black leather chair. It was from the neck down, and showed him reclining, his dark towelling bathrobe open exposing the lean, muscles of his hairless chest and his taut stomach. He had the tight, athletic build of a swimmer or footballer. She bit her lip as her eyes slid lower, taking in his tight, light-grey shorts clinging to his lightly-haired thighs. She leaned a little closer, examining the large, unmistakeable bulge in them as she used one hand to peck at the keyboard, whilst the other slid beneath her skirt and began to stroke herself through her white uniform panties.

frustratedGrl: omg, is that really you? you haven't cheated and copied a pic from the internet?

Neal25: no, it's really me

frustratedGrl: wow, you're hot, mister Neal25 :-p

Neal25: thanks, can we continue now?

frustratedGrl: oh yeah, believe me, i'm more ready than ever :-o so truth or dare?

Neal25: truth: are you touching yourself right now?

frustratedGrl: what a question?! maybe a little...

Neal25: tell me more...

frustratedGrl: right now, i'm lying back on my bed, typing with one hand, whilst gently running my fingertips along the edge of my knickers with the other. it feels so nice. naughty but nice!

Neal25: first, stripping off in public, then sending me pics, now playing with yourself. what a naughty, naughty girl you are!

frustratedGrl: hey, stop distracting me! it's my turn now, no bending the rules!

Neal25: ok, truth or dare, sexy?

frustratedGrl: truth: if you were a teacher at my school, what would you have done if you'd caught me without knickers? :-o

Neal25: well, obviously, any girl so flagrantly ignoring the rules around school uniform needs correction

frustratedGrl: oh yes, i desperately need some 'correction' ;-)

Neal25: so i'd take you back to my study, bend you over my desk and give you a damn good spanking!

frustratedGrl: ooh yes...

Neal25: can you imagine that? being forced to bend over my hard wooden desk, your bottom stuck in the air, my hand on your back pinning you down as i ease your skirt up over your shamefully naked buttocks

frustratedGrl: yes, I'm so ashamed at being caught! i feel so naked and vulnerable as you raise your hand...

Neal25: I slap you a few times, loving the harsh sound of my firm hand on your soft, rounded arse cheeks

frustratedGrl: ouch! i squeal, the tender skin of my bottom all hot and tingly, I squirm and kick my legs but you hold me firmly

Neal25: what a wicked, dirty girl you are, walking around without any underwear, I say as i spank you again

frustratedGrl: I'm sorry, I whimper, please stop, it hurts!

Neal25: i pause, running my hand over your smooth skin, feeling the warmth of your reddened cheeks as i caress your gorgeously pert arse

frustratedGrl: what are you doing? have you finished? i say hopefully, trying to stand up

Neal25: stay down, girl, i say sternly pushing you back down roughly and tapping your ankles, making you spread your legs a little wider

frustratedGrl: please, sir, no more (my bottom's warm and tingling, but i'm starting to tingle somewhere else too!)

Neal25: with your legs wide apart i can't resist slinding my hand between your warm thighs and exploring your nakedness, i smile when i feel how moist you are