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

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"Mattie, can I have a word please?" his stepmother asked. She had called him Mattie ever since she was first introduced to him. His father had used the name and it seemed to stick, in fairness, Matt preferred her using it as his birth mother called him Matt and he wanted to distance himself from that woman as much as possible. She had done the dirty on his father with one of his best friends and although she had insisted on having custody of her son, Matt had asked if he could stay with his father.

Serena had been introduced to the family 7 years ago and she had proved to be an excellent maternal figure for Matt despite being a few years younger than his father. She and Matt had quickly established a special bond which his father had encouraged and she was always enveloping her stepson in hugs for no reason sometimes; he in turn always went to her first when he was seeking advice on topics rather than his father. She was always at pains to ask "What about Mattie" whenever his father was making arrangements to do things or book holidays. As 'Mattie' got past the age of majority he started to have thoughts about his voluptuous stepmother that perhaps he shouldn't have. She was very beautiful but that was amplified when she shot him a broad grin which seemed to be more often than not. He had developed into a breast man thanks to her and now it seemed all he could think about was her chest.

He had sneaked a peek at one of her bras while it was in the laundry and saw it to be a 36DD; his subsequent research demonstrated that this was, while not rare, a substantial size. Neither could he ignore her sizeable round butt which she inadvertently showed off regularly in her exercise shorts. She only stood 5 7 and her brown hair cascaded across her shoulders but all in all, she was the epitome of perfection, just right for his wank bank fantasies. As Matt stepped towards the living room where she had hailed him from, he noticed his laptop sat on the coffee table. "I appreciate you are a man now" she began, adding "But we need a word about some of the websites you've been browsing."

The colour on Matt's face drained at this announcement, he knew exactly which sites she had referred to, it was an activity that seemed to be taking up more and more of his time. His only hope was that the volume of the various video browsing had hidden his keyword searches for mature or stepmom videos and stories on the likes of Literotica.com. With a slightly broken voice, Matt asked, "What browsing is that?"

"Porn, young man. Pornographic videos to be exact" Serena stated sitting with a rod straight back. She did lean forward and placed a comforting hand on his knee as her tone softened "Look I appreciate you are curious and all but learning from those things isn't healthy, it's not a reflection of real life. Have you slept with a girl yet?"

Matt was floored by the question for a moment but eventually mumbled "No I haven't" as he shook his head.

"And am I right in saying that you are watching those so you know what to do when the time comes?" Serena pressed on oblivious to her stepson's discomfort at the subject matter.

The reality was that Matt used them to get himself off quicker and that a number of the videos he watched were about big-breasted mature women. "Errr... yes. Yes, I want to be a good partner when the time comes." He knew his stepmother's default stance on most subjects was to rally behind the female viewpoint, not appreciating what it was like to be a horny teen boy with a ready supply of porn to help him whack off, but he figured saying what he did would at least earn some brownie points back to mitigate her disappointment.

"Well, there are a number of books and websites your father and I could direct you to, we would happily fund those investments in your education" Serena stated, failing to appreciate the euphoria Matt got while whacking off, especially to MILF porn when the actresses looked a lot like her, Syren De Mar being one of his favourites for her likeness of Serena.

Matt squirmed while he composed his words but countered her by saying "I appreciate that, I really do. My concern though is whether a dry book or web script can really purvey the emotional connection between two people."

Serena looked confused and stated, "I'm sorry I don't understand."

"Well," he began "a friend of mine lost his cherry to a hooker and it filled the required sexual education for him but it ultimately left him a little emotionally stunted." It was at this point he played his trump card, "I could do the same but I want my partner to enjoy it just as much as I want to but I'm worried that it will leave her disappointed, especially if it were her first time as well. It could really put her off, you know? I don't want it to be just a sexual act, I want it to have an emotional connection as well." Who was he kidding, he was a young male with hormones running and he needed to get off regularly and the porn inspired him to achieve this.

"I'm very proud of you for your grown-up attitude on a very important topic, I really am, but I'm at a loss to work out how these videos can give you an education in emotions" Serena stated patting his knee once more.

Matt could sense he had the upper hand in this and so continued "I'm not sure how much porn you've seen lately, well, some of the actresses show just how much they appreciate individual acts. I fully appreciate that they are just acting but it's no different from a footballer selling a dummy to an opponent it at least teaches me how others might handle a situation rather than me having to react to them blind when the time comes." He hoped this argument might at least head off her banning him from watching porn; he was old enough and plenty of his mates watched it so why shouldn't he.

Serena sat for some time mulling his words over in her head before she eventually replied "Yes, I can see your side of the discussion now. Thank you for putting your stance forward so eloquently." Matt wanted to do a fist pump at her words, it sounded like he had won her over. "Is it practical help you need?" Serena asked.

Matt was floored once again by this latest comment, not knowing where it was heading he stumbled "Err... yes, I guess. I just want to be the best I can be when the time comes."

His stepmother's expression was proving hard to read, all he wanted was to be able to continue whacking off to porn. "Well, I suppose I could help you with that. It is a parental duty to prepare the next generation for the world ahead" a steely resolution in her voice.

Matt didn't have a clue what she meant and said, "I'm sorry I don't understand."

"You know help you, give you some practical tips" she stated. Almost an Ewwww moment but Matt slowly nodded as though he understood even though he didn't. Just then he was properly bowled out as she added "I can't have sex with another man, I love your father too much. I do however want to help in some way, I feel it's my duty as a stepparent, I couldn't help noticing the number of videos you watched on the topic of anal sex, more specifically anal sex with mature women." Matt stayed silent as she finished what she was saying "I can teach you how to fuck me in my ass, some girls may not like it but it is a sure way to avoid pregnancy and so I strongly recommend you do your best to persuade them of its merits. If you are speaking from authority of having done it, you will be just as eloquent as you were with me earlier."

"Errr... you mean... that is to say... you... you... you... you know, you'll let me perform anal sex" he blustered, adding "And you're going to let me inside your butt?"

"Yes," Serena answered matter of factly. "A lot of women enjoy anal sex, me included, I want to help you to be a better man to all the young girls out there."

Matt was still wondering if he pinched himself, he'd find himself asleep; his wank fantasy was offering her butt to fuck. "Errrr... errr... errr..." Matt stammered, still not believing what he was hearing.

"Come on, we don't have all day. Stand up, drop your trousers and show me what we're working with. Not a word of this gets back to your father, you understand me?" Serena prompted with an accompanying stern expression. Matt slowly stood up, still waiting for the joke to be proclaimed, he unbuttoned his trousers and allowed them to shimmy down his legs. His dick was making a sizeable lump in his underwear prompting Serena to state "Come on, off with those too" pointing at his underwear. Matt drew in a deep breath and then pushed them down around his ankles making his erection spring up. On impulse Serena gasped and proclaimed "My, you will prove popular with the young ladies when you start sleeping with them. That's impressive."

Matt started to grin broadly as he asked, "Bigger than Dad?"

Serena was still staring at his hard dick inches from her face. In an almost trance-like state, she slowly proclaimed "Yes, longer and wider." He flexed his dick as she was saying that and it leapt slightly from his crotch.

He was silently screaming in his head 'Go on, put it in your mouth. Suck it.' Serena sat staring at it briefly before her right hand came up and grasped the base of his cock. The pulses shooting around inside him generated a heady, almost euphoric, feeling.

She cast a gaze up at him and asked, "Have you ever had a girl use her mouth on you before?" He shook his head and she smiled broadly as she turned her attention back to his hard dick. 'Good' she thought while opening her mouth and taking him inside, 'All future times will be compared to me from now on.' Matt groaned loudly as her lips closed on his length, it felt amazing and if he didn't focus, he could well be coming in seconds. He had seen in countless videos women going down on their male partners, and it had to be said going down on other women in lesbian videos. Serena took him as deeply in her mouth as she was able and then pulled back, drawing her lips tightly along each vein and ridge of his cock. Just when he thought she would fully withdraw from his dick she changed course and ducked her face forward once more.

Matt was standing there cradling the back of her head in one hand and with his head tilted back groaning "Oh my god that's good." He didn't look down at her and if he had he would have seen the corners of her mouth curled up in a grin.

She had never intended this to happen but hearing his reaction, knowing she had him in her thrall, knowing he was feeling for the very first time an intimate connection with someone, knowing she had such a nice cock close to hand all combined to have her pussy buzzing at this most unexpected of situations. It pulsed like it never had before but then it had been so long since she had sucked on a cock and even then, it wasn't as special as the one before her. It was this last thought that galvanised her into action; she was going to make him come with her mouth alone. He was young, he would rejuvenate easy enough and they had plenty of time before her husband was due back.

Matt couldn't believe how amazing it felt to have his dick sucked, judging Serena to be some kind of expert the way she was pleasuring him. Sadly, after only a few minutes he started to feel the well-known sensation in his balls; he was going to come and there wasn't a damned thing he could do about it. He brought his head back to look down at his beautiful stepmother, her gaze was fixed along his length and she had a determined expression. He had seen in videos that quite often the men warned the woman when they were about to come but he was so overwhelmed that the best he could manage was a deep growl and then proceeded to fire his come at the back of her throat. Serena blinked her eyes while he was coming and once she thought he was done she slowly pulled back while keeping a tight suction on his dick. Once fully removed, she looked up into Matt's gaze and theatrically swallowed load down her throat she smacked her lips and said "Very tasty."

Matt was still struggling to retain his composure. His hot stepmom had just sucked his dick until she came in her mouth and not only had she swallowed his come, she was still sitting there with a tight grip on the base of his cock. "Erm... I'm not really sure what to say... and that was really nice and all but... you know... how was that teaching me about anal sex?"

While maintaining her grip on the base of his cock she replied "Yes, I can see why you'd ask but the reality is that once a man has come, he can normally hold off his second round substantially longer. Basically, I don't want you coming too quickly. Does that make sense?" Matt nodded eagerly; knowing he hadn't done yet was enough to keep his dick hard. Serena now stood up as she pushed him to sit back on the sofa behind him, she let go of his dick to announce "The trick you need to learn first and foremost with anal sex is the importance of lubrication. A girl's vagina produces its own juices to make it enjoyable for both parties, anal sex however needs assistance. It's best to use a main brand lubricant that you can get from many shops or pharmacies; we don't have that to hand so we need to improvise." She walked over to her handbag and extracted a small tube and held it up for Matt to see "Hand cream or body cream has a suitable viscosity and will make a suitable alternative."

'I've seen blokes use their own spit in the movies but then that's not to say they didn't use lubricant in the background' Matt contemplated in his head. As it was Matt didn't care as he was about to fuck this gorgeous woman up her butt and she was going to let him willingly. He kept quiet as Serena turned to face away from him, removed her skirt and panties, she then squeezed an amount of the cream on the tips of her fingers before reaching behind her and worked it into her sphincter.

"It's vitally important to use a lot of lubricant. I've been doing anal for a while now and so I'll be able to accept you easier than a first-timer but we'll cross that topic on a future occasion" Serena stated.

'Future?' thought Matt 'That sounds like this won't be a one-off.'

He was stunned further when Serena turned back to him and knelt before him. She squeezed a generous amount of cream in her hand and grasped his dick once more saying "Once the receiving hole is prepared it's important that you are also generously covered." She then set out to coat his entire length with a sheen of the cream. Matt loved having her work his dick again; he had seen plenty of videos where MILF's worked a dick with the hand until the bloke came over her hand although having come already he was determined not to come too soon this next time.

Serena stood back up and Matt got a close-up look at her sparsely-haired pussy as he contemplated 'Maybe I'll get to try that out one day if I play my cards right, especially if there are to be repeat occasions.'

Serena turned around and wiggled her butt at him saying "Okay both participants are now prepared. I'll take the lead as that means the recipient can control how much is taken and how quickly." Matt was just enjoying seeing close up that wonderfully full round butt pointed at him from inches away; his first instinct was to lean forward and start to kiss his way around the fleshy cheeks. Serena made to sit down until her butt was nudged against the head of his dick. She then reached between her legs and took hold of his dick to aim the head at her anus. This was another occasion where he revelled in the feeling of her hand on his dick. She pushed her hips down a little bit until the head of his dick nudged inside her slippery butt.

The thing that his video-watching hadn't prepared Matt for was just how warm it felt to be inside her butt. Serena gave an appreciative groan and Matt followed suit as she pushed her hips further so he slipped further inside her. His elegant stepmother that had been an integral part of his life for the last few years then sat back up only to then stall and then sink back down on his dick a little further than before. Matt was in seventh heaven having his dick buried in a very snug butt, the fact that the butt belong to his gorgeous stepmother just amplified the sensations further, it was then that he discovered what true beauty was. She turned to look over her shoulder at him and after groaning said in a hoarse voice "I hope it feels nice for you as it feels amazing for me. I haven't had anal in some time."

All he could do was nod. His balls were tingling once more and he was trying to think of anything other than letting his come fly, especially after Serena started a steady rise and fall along his dick. It didn't help when she started mewling and groaning appreciatively as she fucked herself. She leant forward and braced her hands on his knees to get some extra leverage and as their fucking intensified Matt took a firm hold of her hips which seemed to encourage her to fuck herself harder. With a strained voice, he groaned "I can't hold off any longer, I'm coming" and as he let his come fly, he added, "I'm sorry."

Serena sat down fully and waited until he had finished coming. She then leant back against him and took his right hand, pulling it around her and placing it directly over her clitoris as she gasped "I'm close, rub me there to get me off. Please I beg you." She still had her hand over his and her prompting encouraged him to determinedly rub his fingertips over the fleshy nub he could feel. A couple of minutes of this treatment and her breathing was reaching a crescendo so he looked over her shoulder just in time to see a long stream of clear come shoot out from her pussy towards the coffee table. While she was coming, her anus gripped his dick further which had failed to deflate due to the firm grip her ring had on the base of his cock.

The couple sat like this for a while until their breathing returned to normal. Serena pulled herself up looked over her shoulder asked, "Did you enjoy that?" to which Matt nodded enthusiastically and so she added, "I did too, especially as you made sure I came as well." Looking over at the coffee table she said, "I haven't squirted for some time, I think that's a true demonstration of just how enjoyable it was." The crucial things were that she hadn't moved and Matt's dick hadn't deflated much. She squeezed his dick with her anus and asked, "I take it someone could go again?"

Matt didn't want to look this gift horse in the mouth and replied, "Yes please, assuming we have enough time."

He was momentarily disappointed as Serena sat upright and disengaged his cock but then she went and knelt on the floor on her hands and knees saying "Shall we try a different position" wiggling her butt in his general direction. Matt sat on the edge of the sofa so he could discard his trousers and underwear, he then went and crouched behind her backside thinking back to what he had seen in countless movie clips. As he plugged her anus with the head of his cock Serena tilted her head back and groan "Oh that feels so good as it goes in" which was enough encouragement for him to slowly bury his dick back in her sphincter. With each passing thrust, Matt gradually increased his depth until he was really going to town on her butt, all the while with a background soundtrack of Serena's gasping and groaning.

Conscious of their previous coupling Matt let go of one of her hips and reached around to feel around her clitoris and labia. Serena just had time to gasp "Grab my hair at the back of my head." Again, his video browsing proved useful as he had seen something previously and grasped her hair with his left hand while the right was diddling her clit. "Yes, yes, yes" she wailed as her anus gripped his dick tightly. This was an obvious sign that she was coming and in return, he gave a further five short thrusts until he held still as he came coating her bowels once more.