Addiction

All comments and feedback are gratefully received as I'm hoping the feedback will encourage improvements in my work. This is a work of fiction from the deep dank recesses of my mind and any resemblance to real people is purely accidental.

This story depicts initial reluctance of mature anal sex, if this not to your liking, please visit some of my other submissions, otherwise I hope you enjoy.

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Lenny's position in the lecture room afforded a perfect view. Turn your head one way and you could scan through the door glass down the corridor, turn the opposite way and not only did you get a good view out of the window but you could cast your gaze on the girl everyone considered the years hottie. She didn't capture his imagination though; she was too high maintenance and too young for his tastes. He had a thing for MILFs and the one stood at the front of the class was his prime masturbatory fantasy. His position provided a side on view to admire the swell of her breasts that she tried to hide under jackets or baggy jumpers but as she turned to write something on the board, inadvertently stretching for the top left corner of the board, the swell of them stood out for his hungry attention.

Lenny wasn't a grade A student, he did okay in most subjects, always in the top ten but it was Andrea's class that he hit it out of the park. The blonde always seemed pleased when he entered work and always gave little message feedback to encourage him further. As her class was the final class for a couple of days each week, Lenny always stayed back to help her pack books and teaching aids away ready for the next day. Lenny couldn't shake the feeling that the brunette was distracted today but he couldn't put his finger on why. The class had been their normal attentive self, even with it being the last of the day, few seemed distracted or bored but still something nagged away at him.

The class had ended and as per usual he was the last student present, ferrying books back to shelves when Andrea picked up her phone to read a message that had just come in. She clicked it closed and put it in her bag before announcing "I need to go see the Principal. Finish up here and off you go for the day" she gave him her usual smile but there seemed something missing in its warmth today.

Lenny wanted to smell her perfume one last time and so, as the door closed behind her, he reached into her bag with the intention of smelling her phone. A quick look at the screen showed that she had not locked the phone after all 'Whoops, I'd better lock this for her' was his initial thought but then another thought cropped into his head 'I wonder if there are any photos of her on here' and so he found the Galleries icon to scroll through the images. He hadn't realised how lucky he had been, another ten seconds of inactivity and her screen would have locked itself automatically.

There were the usual suspects of scenic views, family gatherings and then a new text came in. The screen showed the first couple of lines that read 'Get home as soon as you can. I'm ready to take your a...' Frustratingly the preview ended there and so Lenny switched to her message icon to read more. This is when he had the first shock, Andrea had saved a number of messages from her husband about how she liked having his cock in her butt. Other messages were her replying that his having to work away sometimes frustrated her when she needed a dick in her butt and that she would frequently use dildos and vibrators to tide her over. After a second's pause Lenny took a series of photos with his own phone of some of the messages. He was momentarily stunned that the subject of his wank fantasies liked anal sex -- according to what he saw a lot.

Lenny then switched back to the photo archive and came across the next gold mine. They had been taken by her phone and showed someone's cock penetrating a woman's ass -- he guessed a woman by the shape of the hips. Some of the images showed a tattoo on the small of the woman's back -- a tramp stamp and this made Lenny's head spin. He had seen this tattoo once before. It was some months ago when he was helping Andrea clear away and she was scurrying under a desk to retrieve something and her blouse had ridden up to reveal the very same tattoo. His mouth was dry, his legs shook and he had to steady himself against the desk behind him - He had found photos of Andrea taking a dick up her butt - straight away he forwarded them to his phone. He was going to enjoy himself tonight flicking through these as he flexed his hand along his own dick.

When the photos he wanted were all transferred to his own phone he quickly set the message he had read to unread and then discretely returned her phone to her bag -- after locking it of course. His return home was made in record time and on arriving home he settled down to time alone with his hand; only it didn't last as long as he had anticipated due to his excitement. Thankfully that excitement meant he recharged quickly and performed the same very quickly. It was during his post come hiatus that his inspiration struck. He had the perfect material to use as a bribe to get her to allow him to have his way with her body -- what a treat that would be. But would he dare? He actually liked Andrea as a tutor but that chest and now he had seen it, that butt was really all he could think about.

The next opportunity to raise the topic was on Wednesday. Once again, he was the only one left helping clear the books when he tentatively asked, "Can I ask you a personal question?"

"Of course" came Andrea's reply.

"I have received some information about someone and wondered what to do with it" Lenny replied coyly.

"What kind of information?" Andrea asked.

"Well, I found your messages and photo's about having a cock up your ass. If it gets out, it will ruin your career and I would prefer that didn't happen as I think you're an excellent tutor but I can't ignore the fact you like getting butt fucked and I really, really want your butt. I love anal sex and think you are adorable. I heard a few years back that a schoolteacher took part in porn movies; when it came to light, she lost her job and perhaps more worryingly couldn't find anyone else to take her on and I wouldn't want that happen to you." Lenny stood there waiting for her reaction.

As soon as he mentioned 'cock up your ass' the colour drained from her face, unbeknown to Lenny her sphincter gave a small pulse at the subject. Lenny held up his own phone to show one of the images she was familiar with. "I... I... I" was her stumbled reply. "How...?" she asked shaking her head in disbelief.

"Look, I don't want you in any trouble but I can't ignore what I've now seen. The how is irrelevant, all that matters is what we do from now on." Lenny sounded more controlled than he was actually feeling but she wasn't picking up on his nerves, all she could focus on were his words. "If anyone else had found these, the images would be all over the place by now. I'm doing this because I care what happens to you. The genie is well and truly out of the bottle but I can't ignore that you seem to have a desperate liking for something that I share." He took a deep breath and figured now was a time for masterfulness "Now I want that ass or these start getting leaked."

"I... I... I" was her only reply again as she looked aghast.

Lenny removed a tube from his pocket saying "I even came prepared. Now is the time and here is the place. What's it to be?"

"I... I... I can offer you some money to keep quiet. I don't have much though" she replied as she looked around her. Lenny could hardly contain his excitement at the prospect of her looking around her room.

He went and locked the door and pointed at the far corner storeroom, figuring giving her time to think would work against him. "I don't want money, I want ass. In there will do, as long we don't dawdle about no-one will ever know. Now off with the panties please." He figured ordering her around was preferable to her having to process her own actions.

She was still looking around her with a confused expression but amazingly made her way to the room. Once she was out of sight of the door, Andrea gave Lenny one last look which he replied with a smile and a nod, after another pause, she was prompted to lift her skirt above her hips and hooked her thumbs into the waist of her panties. She gave one final pause as she stated, "I want this noted that I'm doing this reluctantly as I can't afford for this to get out."

Lenny shrugged and replied "Noted." This prompted her to push down and the panties came to rest around her ankles. Her cute curvaceous arse was in profile 'It looks amazing' was Lenny's thoughts as he licked his lips. He stepped up behind her and pushed on her upper back so that she leant over the shelving unit in front of her. In actual fact Lenny had only tried anal sex one time previously but it was enough to start a fascination for the topic which was only fuelled further knowing his favourite subject of his wank bank liked to participate - frequently.

He undid his trousers and vigorously worked some lubricant along his length and then applied the excess to her anus. She jumped slightly at the touch but otherwise remained with her rear end presented to him. His aim was true and he lodged the head of his slippery dick in her rectum making Andrea draw in her breath. Lenny was having to focus on anything his eyes could see rather than on him actually having his dick inside the warm snug ass of his hot teacher. He doubted many students would have her in their own wank bank, there were after all far younger female teachers but Lenny had developed a taste for MILF's through his mothers friends and his friends own Mom's but this one really was the cherry on the cake.

He pushed his hips further as she slowly took his length inside her. Andrea wasn't worried about taking his dick as it appeared no longer than her husbands but the girth of the thing was stretching her more than she had for some time. She was doing this reluctantly but she had enough intelligence to know it would not be a one time thing, he would want this fairly regularly she guessed. Secretly though she hoped he would continue to demand it of her, his dick felt nice as it was lodged deep in her bowels. Lenny took a good grip of her hips as he started to thrust away, working his steel hard length repeatedly in and out of her snug hole.

He had done enough internet research to know that few women climax without addition stimulation but this one visit to her back door was very much about getting him off but not until he had enjoyed her gripping ass sufficiently and so he was suitably shocked when the woman in front of him started to increase her gasping and groaning to such an extent that she had to shove her balled fist in her mouth to muffle the noise. She then started to shake and quiver while pushing her hips back at his cock as her ass muscles clamped down on his dick. This did it for Lenny who gave one final hard thrust and then started to coat her bowels with his come.

The two stayed joined together for some time. Lenny's cock was reluctant to subside and her sphincter was reluctant to relinquish him just yet. Eventually though Lenny was concerned about being discovered and so pulled back with an audible pop from her anus. This was new for Andrea; she frequently took her husband in her rear and he had never generated that reaction before. Lenny was over the moon, the sensations he had felt with an experienced exponent of anal sex had far excelled what he had expected. He hurriedly refastened his trousers and, figuring it was best to remain the dominant one, instructed "You'll be making payment for my silence the same time every week." She nodded her understanding, inwardly relieved she would get to feel the same sensations again. Lenny added "That was amazing by the way" and once he could see her lowering her skirt once more, he unlocked the door and exited the building.

For her part Andrea went to the toilet to clean herself up but then returned to her room and sat for some time while she gathered her thoughts. 'How would their next class together go after he had sodomised her?', 'What did it mean that she enjoyed herself so much?', 'How would she feel the next time her husband fucked her ass?' and as her rectum twitched at the memory 'His cock felt so good buried inside me' were all thoughts rattling around her head. She was brought down to earth as the cleaners knocked to see to the room. Andrea smiled at the older woman, nodded and said "Good evening" as she picked her bag up to make her way home. Her husband Tony was working away again today and so she could mull over her thoughts all evening.

The next time Lenny was in her room things progressed in their usual manner only this time he didn't hang back to help her clear the room for the next day. Part of her was relieved as she doubted, she could stop him if he demanded the next instalment. Indeed, Lenny was tempted but figured he would get more ass by not being greedy and so left it until the following Wednesday. Following the usual pattern, the tall strapping lad held back and helped tidy the room and as the last items were cleared away, both were anxiously holding their breath until Lenny asked, "Ready to make your next payment?"

Andrea smiled at him and nodded as she lifted her skirt clear of her hips. Lenny was surprised when he noticed she wasn't wearing any panties, the realisation of which made his pulse jump at the realisation that his favourite MILF was looking forward to it. Little did he know she was looking forward to their bonding more than he was. This time, once he had buried his entire length in her anus, Lenny pushed her skirt higher so that he could take a photo of his cock inside her including the slag tag on her lower back. The other new dimension was when Lenny, instead of grasping her hips for leverage, reaching around cupped her bountiful breasts. Future couplings would see him lifting the soft round orbs clear so that he could play and pull on her ripe nipples.

She was similarly pre-occupied on her journey home, so much so that she didn't see that she was being followed. Lenny followed her as some of the messages made him suspect that her husband worked away frequently. If that was the case, he had a plan forming in his head that would take this to a whole new level. Over the course of a couple of weeks Lenny would go by her house at varying hours of the day to work out the pattern of vehicles, home surveillance and such. A couple of weeks later on a Monday evening, he followed her home and when he failed to see the husbands car decided to step up to the front door and rang the bell.

Andrea swung the door open and stopped dead on seeing him on the doorstep "Well, aren't you going to invite me in?" he asked.

Despite being wrong footed Andrea stepped aside and asked, "What are you doing here?"

Lenny, exuding all the confidence he could muster, smiled and announced "You're about to make your next instalment. I think twice a week is a better arrangement and you will tell me whenever your husband is working away so that I can come over to feed your back door all evening and night."

Andrea was rooted to the spot with her mouth agape completely stumped by this new dimension. The more she thought about it, the more she liked the idea but that didn't stop her from saying "But Tony's not away this evening, he'll be back around eight."

Lenny was slightly disappointed but none the less shrugged and replied "Oh well, we still have a couple of hours. Skirt up and titties out, let's get on with it." Lenny followed her into the living room and once she had removed her panties and removed her blouse, he pushed down on her shoulders so that she knelt in front of him and asked, "Do you take hubbie in your mouth?" Andrea was looking up at him as she nodded and her gaze fell on the lump in the front of his trousers. "Good you can show me how you worship a cock then."

Without further bidding she reached up and undid his trousers, pulling them down to his ankles and almost immediately engulfed his cock in her mouth. Lenny had had a few blowjobs before but as they from girls his age, receiving the same attention from someone more experienced was a totally different experience. He was tempted to get her bent over before coming but figured he'd only require a short recuperation time, especially with the prospect of getting buried in her ass on the horizon.

Her mouth was too good at what she was doing and he had to let his load go way quicker than Lenny would have liked but he consoled himself in the knowledge that she would be doing so again in the future. With time ticking on Lenny needed a little recuperation time and so his next instruction was "Go sit on the sofa, I'm going to repay the compliment by finally getting a taste of that pussy." She really did look hot with her only clothing, her skirt, bunched around her waist. Kneeling down before her, Lenny's first port of call were her breasts where he could finally get his lips wrapped around her firm nipples.

Again, it wasn't his first time experiencing having the rubbery nub in his mouth but these far eclipsed the young girls buds he had encountered before. The gasping and moaning he was generated was also different, more intense, as Andrea cradled his head against her breast as tiny pulses shot around inside her. His devotion of the MILF was well founded and knew it would set a trend for years to come. Eventually though Lenny progressed downwards and took her clitoris between his lips and under his tongue and once he worked his tongue down so that he could burrow inside her -- she really did taste delicious.

It provided the short interlude needed and he knelt upright with his reinvigorated dick pointing straight at her pussy. In a flash Andrea put her hand down to block his way "You can have my ass anytime but my pussy is only for my husband. Sorry."

Lenny shrugged as he was more interested in her back door anyway and so he replied "So be it. Get down on your knees so you can take me up the arse." Andrea quickly complied, scrambling down on to the floor and presented him with her ripe peach of a butt. Lenny was getting very adept at applying lubricant quickly and within less than a minute he was slowly pressing forward his dick as her butt engulfed it in it's warm snugness.

The accompanying groans and moans and her beseeching him to "Fuck that ass" and "Go deeper. Oh god, go deeper" were her suitable encouragement. It was about now that it dawned on Andrea that she had become addicted to the treatment Lenny administered on her. At the same time Lenny was coming to the realisation that he was becoming addicted himself to her tight back door. Thankfully the two concluded with plenty of time for Lenny to make his exit and Andrea to grab a shower before her husband landed home.

The next time Tony was working away Andrea sent Lenny a short message which meant he had the opportunity to fulfil his promise. He turned up at her house soon after she landed home and the entire evening and most of the night were spent with his cock erect and either nestled in her rectum or with her lips wrapped around it. It afforded Lenny a suitable length of time to practice his oral attention on her juicy pussy or him to lie back and enjoy the qualities of the MILF's blowjob of which she was proving very accomplished. Andrea spent many happy hours that night on her hands and knees with Lenny buried in her ass behind her, he was proving a suitably proficient at working her back door.

It was every youth's dream to have his hot tutor addicted to his cock. With the exception of her pussy, he was denied nothing although that in turn was yielded a couple of weeks later. Lenny was stopping overnight once more and had her knelt before him on the bed ready to take him back into her anus. He had already fucked her butt earlier that evening, coating her bowels with his come, when he took up position knelt behind her but this time, as he took a firm grip on her hips, he sunk his entire cock inside her snug pussy. Andrea had protested and tried to wriggle free but Lenny had too firm a hold and just started to fuck her pussy as though his life depended on it. Andrea's protests withered away under his onslaught and from then on, he was allowed in any hole he wanted. His cock just felt too good when it was buried inside her sending her to even more heights.