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.
