Helen's Anal Craving
by Sexaddikt
Copyright© 2025 by Sexaddikt
Erotica Sex Story: A teacher harbors a secret desire for anal sex, and things become more spicy when she meets her old friend...
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Consensual Romantic Anal Sex Analingus Masturbation Oral Sex Petting Size .
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 reveled 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 had 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 her, 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.
The 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 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.
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