Helen had recently turned thirty and reaching this age had somewhat depressed her. She wasn't lonely as such - she was a popular and successful teacher with plenty of friends and a good social life. However she had never really been happy with her sex life, and her frustration had by now grown considerably.
She had been through several relationships, and even one or two flings, but none had satisfied her. Part of the problem was that, though not unattractive, she was not physically glamorous. Her short blonde hair had always made her rather tomboyish in appearance, and only in recent years had she swapped her glasses for contact lenses.
These features had always rather overshadowed the fact that she had a very good body, and combined with her quiet, shy personality, meant that the men with whom she tended to become intimate were work associates. And though they were pleasant, her work associates were sexually rather dull.
She longed to have raw, intense sexual experiences, but this had never seemed remotely possible with any of her partners thus far, and she was too shy and self- conscious to go actively seeking such things. She also knew that most normal women would have been happy with the sex life on offer from her previous boyfriends. But Helen was not sure that she was "normal".
For as her adult life had developed, Helen had become aware of a deep and dark craving within her. Though she enjoyed regular intercourse and both giving and receiving oral sex, she had developed a longing - almost a need - for anal sex.
At first she had tried to dismiss it as a phase she was going through. But then she had begun to finger her anus in the bath and in bed, and revelled in the sensations this produced. She had even plucked up the courage to buy an anal vibrator, and by now she was amazed that it still worked with the amount of usage she had given it.
However the physical sensations of having her anus stimulated were only part of her longing to be "buggered" (how she loved that word!) It was the mere idea of being possessed by a man in that way, of being so totally debased, that really made her shiver with delight. She had enjoyed a good, clean upbringing, yet the very fact that she so wanted to experience such a depraved and dirty form of sex only turned her on more.
She had eventually succumbed to temptation and ordered some videos from Holland exclusively dedicated to anal sex. She watched in amazement as she saw cocks sliding deep into tight bottoms, and would masturbate furiously and repeatedly as she imagined this happening to her. She took to joining porn websites, though only those with a large library dedicated to anal intercourse.
She even sought out the most extreme anal scenes. The rougher and harder the anal sex the more she enjoyed watching it, and she loved to hear the girls beg for it the way she wanted to. She also longed to do what she saw so many porn actresses do, which was to suck a cock that had just come out of her arse.
She began to look at each man she knew in a different way, asking herself silent questions about them. "Would he give me anal sex if I asked him?" she would say to herself. "Or would he be appalled by the idea?" As she conversed with attractive men she imagined herself whispering to them something like, "Can I be your anal slut?" or "Would you like to fuck me hard up the arse?" and would suddenly blush in the midst of conversation, much to the bemusement of the men she was talking with.
However Helen's fantasy remained just that - a fantasy. She simply didn't know how to go about turning it into reality, yet her secret desire just wouldn't go away.
One day, Helen was checking a school reunion internet site with which she was registered. She had never bothered to meet up with any of her old acquaintances from school and university, but she sometimes found it interesting to see familiar names and faces and read what they were getting up to. Today however she saw a newly registered name that made her feel differently.
Shawn was a friend from her university days of about ten years ago. In fact he was more than just a friend, as the two has kissed many times, and Helen had even let him fondle her breasts (usually when she had been a little drunk!) Then a very nervous virgin, she had never allowed him to go any further with her, and they had lost touch soon after graduation, much to Helen's eternal regret.
Seeing Shawn's name on the screen, she recalled more strongly than ever their dalliances. She had always enjoyed his flirting and persistent advances - he was a very attractive guy - and secretly a part of her wanted to surrender to them completely. He had always spoken openly of being very energetic and adventurous when it came to sex, and had made it plain that if Helen wanted to try anything, he would gladly oblige.
If only Helen had known then what she knew now. She knew that if she were in the same position now she would let him fuck her. More to the point she would ask him to fuck her up the arse, and in doing so feel very confident that he would happily oblige.
As Helen pondered this she noticed that Shawn had described himself as single. The thought that this was a golden opportunity was inescapable. His email address was right there. What had she got to lose?
Before she could talk herself out of it Helen quickly wrote him an email, telling him a little about what she'd done since they had last seen each other, and asking if he would like to meet up for a drink. Pointedly she remarked that she was single, lived alone, and had missed him.
No sooner has she hit the 'send' button than she was having second thoughts. What if he laughed at her, or told her he had no interest in seeing her? Yet at the same time she was excited, and she had trouble sleeping that night as she imagined what might happen.
As soon as she came home from work the next day she checked her email and her heart began to race as a reply from Shawn hit her inbox. She opened it breathlessly, and was relieved and thrilled to read that he would love to meet up with her, and had enclosed his telephone number.
His voice sounded exactly as she remembered it when she ran she rang him. He seemed genuinely pleased to hear from here, and Helen found herself blushing when he began to flirt with her just like he used to. He lived in London and she just outside the city so it was easy for them to meet. They arranged to have a drink the coming Saturday in a quiet pub she knew not far from her flat.
When they met up at the pub they embraced as old friends do. Helen found him even more attractive than she had remembered him - more rugged and mature. They were soon chatting away happily, Shawn as usual never missing the opportunity to make suggestive comments here and there, gently tapping Helen's knee with his fingers as he did so.
They hours passed by quickly, and suddenly it was closing time. They had both by now become very slightly drunk, and giggled together as the bar staff urged them to leave.
There was a brief moment of awkwardness before Helen grasped the nettle.
"Would you like to come back to my place for a coffee?" she asked, fully aware that when you ask a guy back to your place for a coffee at not far off midnight he is going to expect more than coffee.
"Sure, that sounds like, um, an interesting idea," replied Shawn, and his smile reassured her.
They linked arms as they walked back to Helen's flat, and even some light rain did doing nothing to dampen their spirits.
After giving him a brief tour of her flat Helen poured them another couple of drinks and they sat down together on the sofa. They began chatting away again, but this time the conversation was quieter, gentler.
At what both knew to be the right moment they kissed, Helen's tongue snaking into Shawn's mouth. As they continued to kiss, Shawn gently stroked her hip. Impatiently, Helen grabbed his hand and slid it beneath her top up to her breasts. He cupped her right breast in his hand and squeezed, and though their lips remained in contact she moaned softly.
Helen was more turned on than she had been in a long time, and she felt as though she was losing control of herself. She pulled away the arm that was around him, and unbuttoned her jeans. Then she grabbed the hand that was massaging her breast and pulled it down to her crotch, pushing it beneath the denim and against her now very moist panties.
This time their lips did part and Shawn looked at her quizzically. He remembered as well as she did how at university she had repeatedly never let his hand or any other part of him get below waist-level. Now here she was actually pushing his hand beneath her jeans!
The look of pure lust Helen gave him told Shawn everything he needed to know. They kissed again, even more passionately and urgently than before, and Helen's breathing became deeper as she felt his fingers start to rub her soaking wet sex through the thin silk of her panties. He then pushed aside the material with his middle finger and gently slid it inside her, and Helen disengaged her lips from his, tossed her head back and groaned.
Now overcome with desire Helen withdrew his finger and began to yank off their clothes. Shawn responded with equal urgency after literally almost tearing off their garments they very quickly found themselves naked. They were now both standing, and they stopped to admire each other's nakedness for the first time. Helen had often wondered about the size of Shawn's endowment and she now observed that it was slightly above medium length but unusually thick.
Almost instinctively she dropped to her knees and took it into her mouth, slurping and sucking greedily. He gripped her head with both his hands as she bobbed back and forth on his hard, thick member. Helen was now quite literally dripping wet, so excited was she.
She finally withdrew him from her mouth, and he reluctantly let go off her head. She rose to her feet and dragged him to the bedroom. When they got there it was his turn to take control, pushing her back onto the bed, spreading her legs, and putting his face to her hot wet pussy. His tongue slid inside her and again Helen released a deep groan of ecstasy. He flipped between licking inside her and letting his tongue dance over her clitoris, a combination that sent her wild.
"Yesssssssss!" she gasped. "Don't stop!"
When he finally did stop it was because both of them knew it was time for them to fuck. Helen remained on her back as Shawn mounted her, sliding his cock firmly into her sopping wet pussy.
"Ohhhhh yesss!" she hissed. "Fuck me! Fuck me!"
Shawn proceeded to do just that, pushing his hard cock in and out of her with regular strokes, and raining kisses down upon her face, neck, and shoulders as he did so.
Helen's pleasure was immense, but even now she felt her secret longing starting to build up within her. Even as Shawn's cock gave her pleasure in one orifice, she could not help but imagine it giving her a greater, almost unimaginable pleasure in another. It was like an itch - an itch that she needed to scratch.
Shawn somehow sensed that Helen wanted something more than just vanilla sex, and though his cock remained firmly inside her, he looked searchingly into her eyes,
"What do you want me to do baby?" he asked. "What do you like?"
Helen writhed beneath him, the physical pleasure she was feeling conflicting with the confusion in her head.
"Just tell me," breathed Shawn. "You needn't be embarrassed. I'm unshockable."
Helen realised at that moment that if she hesitated she would never bring herself to tell him. The only thing to do was to just say it, not think about saying it.
She looked him straight into the eyes and said, "I want you to give me anal sex."
For a moment his reaction was one of surprise, and she immediately feared he would mock her, or find such an idea disgusting. Instead his familiar grin reappeared, along with a distinct glint in his eye.
"You're in luck baby," he murmured. "I love anal."
For a moment she thought he was just humouring her, but the urgent look in his eyes as he repositioned himself assured her that he was deadly serious. Her heart began to race with breathless anticipation - something for which she had waited so long was finally about to happen.
"Turn over, and get on your hands and knees" he ordered her.
Helen turned onto her front in breathless excitement. She was about to tell him that there was lubricant in the bedside drawer when she felt his hands part her buttocks and his hot breath upon her. Was he really going to do what she thought he was going to do?
Sure enough she felt his wet tongue press against her rosebud, and she moaned in delight. He pushed his tongue hard against her sphincter and the tip slid inside. He withdrew slightly then pushed it back inside harder and than before.
"Ohhh!" gasped Helen. "Oh my god!"
As he tongue-fucked her arse, holding her cheeks apart with one hand, his other hand rose to her wet sex, and he slid a forefinger inside her. Helen almost went through the roof, her head sinking into the pillow with a squeal of delight.
After exploring her anus with his tongue for several minutes Shawn pulled his face back. His finger slipped from her vagina and travelled upwards. He pressed the tip against her rosebud and it now gave way easily, his finger sliding smoothly up her tight arse, which was now well lubricated by both his saliva and her cunt- juice.
"Ohhh fuck, yess!" she moaned, at an almost unbearable state of arousal as his finger jammed back and forth inside her bottom.
Finally his finger slipped out, and Helen sighed at the sudden emptiness she felt there. But she knew it would not be empty for long.
She looked over her shoulder to see Shawn slowly lowering himself down over her prone buttocks. Then she felt his cock press against her anus. She knew that it would enter more easily if she relaxed, but her excitement was so intense that she simply could not relax. He pressed harder and harder until finally her arsehole opened up and his cockhead pushed past the sphincter and inside. Incredible sensations flowed through Helen's body as she felt Shawn's thick member invade her aching back passage.
"Jesus, yesss!" was all Helen could say as Shawn gripped her hips and pushed his cock firmly up her slick arsehole. Helen was in heaven - the sensations of mild pain and deep pleasure were even more intensely wonderful than she had hoped.
When almost the entire length of his cock was inside Shawn paused, thinking she might need a few moments to get used to it. Helen realised this, and looked over her shoulder to put him straight.
"Don't be gentle with me!" she moaned insistently. "I want it hard! Fuck my arse as hard as you can!"
For a moment Shawn was a little taken aback. Was this really the shy, tomboyish girl he had known at university? Was it really the Helen he had known then who was demanding that he fuck her up the arse as hard as he could? Either he was dreaming or it was, and Shawn was delighted to oblige. He also had not failed to notice Helen's penchant for dirty talk, and rightly suspected that she would appreciate some dirty talk from him.
"You want hard up the arse do you?" he sneered. "You want me to give you a good hard buggering?"
A thrill shot through Helen as she heard his words. "YES!" she screamed. "YES, THAT'S WHAT I WANT! USE ME LIKE A SLUT AND FUCK ME UP THE ARSE!"
Shawn pulled back until only the head of his cock was inside her, grabbed her hips firmer than before, then rammed the whole length of it hard up her rectum.
Helen screamed again, this time in total and utter pleasure, as an orgasm hit her.
Shawn repeated the stroke, then again, and again, until he had built up a rhythm. Soon he was pounding her tight arse, his balls slapping hard against her against her with each thrust.
Helen was now in the throes of such deep ecstasy that she could barely utter a sound, bar a slight whimper with each thrust of Shawn's cock inside her arse. Her head swayed violently from side to side and tears rolled down her cheeks as one orgasm after another rippled through her body.
Sweat rolling down his body as he fucked her, Shawn showed no signs of letting up.
"You like that, slut?" he said through clenched teeth. "You like me ramming my cock up your shitter?"
"Yesss!" wailed Helen. "I love it! Bugger me! Bugger me senseless!"
Thus encouraged, Shawn redoubled his efforts, one of his hands now gripping her shoulder to give himself more leverage. He now began to sodomize her with his entire body weight, drilling his cock so viciously hard up her tight backside that she was almost lifted off the bed with each stroke.
"OHHHHHHHHHH!" yelled Helen, struggling now to retain consciousness as her bliss reached new heights. The physical sensations combined with her long-felt desire to be possessed in this way were almost proving too much for her.
Suddenly Shawn withdrew, and Helen momentarily thought he must be about to ejaculate. But in fact all he wanted to was change positions. He unceremoniously flipped Helen over onto her back, pushed her legs back against her, and positioned his cock once more against her anus. Despite the severe fucking it had already received, her arsehole again did not give way easily. But again Shawn was not to be denied, and he pushed his hard, sweaty cock against the puckered hole until it surrendered.
"Oh my god!" moaned Helen, as she felt his cock slide up her arse once more. He pressed down upon her, pushing her legs flat against her so that her ankles were against his shoulders. Her arsehole was unbelievably tight around his cock in this position, and he needed all his willpower to stop himself cumming. Slowly he started to slide it back and forth inside her.
"You still want it hard up your arse you filthy little slut?" he grinned.
"Yes!" she said gruffly, staring up at him. "Fuck my shitter hard! I'm a dirty little whore who loves having the shit fucked out of her arsehole!"
Helen could hardly believe she was saying such things, but Shawn certainly believed her as he starting pumping his cock back and forth. He gripped the headboard of the bed with one hand and bounced up and down on top of her, the bedsprings creaking noisily as he pounded her tight rectum.
Sweat pouring off of their bodies, the brutal buggering continued relentlessly for at least a further twenty minutes. But the wonderful slick tightness of Helen's arsehole was proving difficult for Shawn to handle, and he knew that his own orgasm was approaching.
"I'm gonna cum!" he gasped as he continued to ream her arse.
Helen snapped her head back over her shoulder, anxious for this perfect fuck to end in the perfect way. "In my mouth!" she breathed huskily "Cum in my mouth!"
Shawn slid his now slimy cock out of Helen's reddened, distended arsehole, and she spun round, still on her knees. She took his cock into her mouth, revelling in the taste of her own arse upon it, and began to bob her head back and forth, moaning in lust.
Shawn groaned as his own orgasm hit him, and the first wad of cum rifled into Helen's mouth. No sooner had she eagerly swallowed the first load than a second spurted hard against the back of her mouth. She swallowed again and again until he was finally spent. She released his cock from her mouth and kissed it softly before he collapsed beside her.
They lay together, exhausted but satisfied. As they lay in happy silence Helen felt as if she was in a dream world. Her most sordid fantasies had finally come true, with the promise of more to come.
After ten minutes of silence Shawn seemed to guess what she had been thinking. "Anytime you want your arse fucked baby," he said, "you just let me know."
Helen sighed in happiness. "Anytime?" she enquired with a laugh. "How about morning, noon, and night every day? Starting now...!"