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
