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Does Auntie Know Best? Ch. 01

By: mw0212



Billy arrived home from college and walked into his living room. His mum & dad were sat in the living room with Auntie Sam, who was crying. His mum ushered him into the kitchen.

'Your Uncle Pete has been having an affair with his secretary. Sam needs to crash with us for a bit while she sorts things out. Do you mind moving into the spare room so she can have the basement? It'll only be for a while' she said.

'No, course mum. No problem. Is she ok?' Billy replied.

'Yeah, I think so. She's upset, but I think she just needs some time to get over the shock.' She replied.

Billy walked into the living room and looked at his auntie. She was 29 years old, only 10 years old than Billy. She had long red hair and big sparkly blue eyes. He always had a soft spot for Auntie Sam, I guess she was one of his first crush's. 

'There's my favourite nephew! Come and give your Auntie Sam a hug!' Sam called to Billy as he sat on the sofa next to her.

'Hiya Auntie Sam. Mum said you are staying with us for a bit? Does that mean you're finally gonna let me take you out & parade you around?' Billy said cheekily.

'Oh Billy, you're sweet. But I'm not much fun to be around at the moment. Did your mum tell you what happened?' she said.

'Yeah, she told me. Want me to get him for you?' Billy said, smiling.

'You're my protector Billy aren't you. You always have been.' Sam said as he wrapped her arm around her, as she cuddled into him.

The next few days things were pretty chaotic around the house. Billy spent most of the time doing college coursework & trying to keep out of his mum & Sam's way while they reminisced about their youth & how evil all men were! 

One day he was home alone, with his parents at work & Aunt Sam having to go back to her house to collect some things. Billy needed to collect one of his portfolio's from the basement, so he went down into the living room. When he reached up to the shelf to grab his folder, he noticed in the corner of the room a pair of Aunt Sam's boots. They were knee high, brown with a 3 inch chunky heel. He bent down & picked them up, nervously bringing them to his face so he could smell the leather. Fighting the urge to get his cock out and start wanking furiously, he took them up to his room as fast as his feet could carry him.

Once there, he lifted them to his face again. He could smell the leather, but as he pressed his face into the open shaft of the boot there was something else as well. There was a pungent musky smell that he deeply inhaled and it drove him mad. He couldn't resist anymore and started masturbating, rubbing his cock over the leather of one boot while inhaling the shaft of the other. It wasn't long before Billy shot his load all over his Aunt Sam's boots. Now realising that she could be home any minute, he quickly cleaned himself and the boots up and replaced them in the basement. Just as he came back up Aunt Sam walked through the front door.

'Hi Billy.' She said.

'Err, hi Aunt Sam. I just needed to collect one of my portfolio's for college from the basement. Hope you don't mind?' he replied.

'Not at all. It's not as though you're secretly going through my panties now is it!' she chuckled.

Billy laughed nervously as they went into the kitchen. After making them both a cup of tea, Billy tried to continue with his work but the thought of his Aunt Sam's feet & her boots was extremely distracting.

By the time the weekend arrived, Sam seemed to have settled down a bit. She came walking into the kitchen to find Billy with all his paperwork out, on the kitchen table.

'What are you up to Billy?' she said, walking into the kitchen.

'Not much' he replied 'I'm just finishing some coursework.'

'My god, you're all work aren't you! Do you ever leave it & get out?' she said.

'Well, I'm pretty much done. Just tidying things up. Besides, what is there to do? My mates are all off on a binge drinking weekend and it's really not my thing.' He replied.

'Well, I'm off shopping. I've still got Pete's credit card & I intend to give myself some retail therapy! You wanna come? She said.

'Oh, I'm not sure' Billy said.

Sam all of a sudden smooched up to him and grabbed his hand. 'You're not going to let me out all by myself are you? Not while I'm so low still & vulnerable?' As she said this, she teasingly ran her nails along the palm of his hand. Shivers shot through Billy's whole body, as he realised he'd get the chance to spend some quality time alone with his sexy auntie.

'Ok then, I'll come and protect you.' He said.

'Great!' she said and kissed him on the cheek. 'Let me go get changed, won't be a tick.'

Billy got dressed into some jeans and a shirt. He thought he'd better make some attempt to look half decent. As he waiting in the living room, he started getting nervously excited just as Sam walked into the living room.

'Wow, I've just realised how grown up my little nephew is!' she said as she looked at him.

'Well you're not looking too bad yourself!' he replied. Looking her up and down, she was wearing a knee length floral skirt with a crop t-shirt. Completing her outfit were a pair of black leather cowboy boots.

'Nice boots' Billy commented, trying not to look as though he was drooling all over her.

'Thanks Billy. I love them too.' She cooed back, with a big beaming smile.

As they walked through the mall, in and out of shops, Billy could see that her heart wasn't in it. They were in a well known clothes store when Billy saw a lovely black dress.

'Auntie Sam? This would look great on you.' He said.

'Really?' she replied 'isn't it a bit "young" for me?'

'God, no. Not at all. I think it would suit you down to the ground! What size are you? 10? 12?' Billy said.

'Oh Billy, bless you. I'm a 14 & you know I am!' she said cheekily. 'Shall I try it on?'

'Yeah, go on! I reckon it'll look great!' Billy said.

Sam picked out a 14 and headed off to the changing rooms. Billy lingered outside with the rest of the men who were waiting for their wives & girlfriends.

'Well? What do you think!' Sam said, doing a little twirl as she stepped outside.

Billy saw that it looked fantastic. The dress was well fitting & showed all her curves in the right places.

'Wow, that's hot! You look amazing!' Billy said.

'Really? You're not just saying that to make your old Aunt happy?' she replied.

'Old? Aunt Sam you're not old! And yes, you look gorgeous!' Billy said.

She put her arms around his neck & kissed him on the cheek.

'Thank you Billy.' She said.

'What for Aunt Sam?' Billy asked?

'For putting a smile on my face. It's been a while you know, since someone has paid me a straight from the heart compliment.' She answered.

'Well, it's true. And you're worth it.' Billy replied. As he said that, he felt her nails scrape across his neck tenderly, again sending shivers through his body making him shake.

'Are you ok?' she asked.

'Yes, yes. I'm fine.' Billy stammered, trying hard not to let on to his Aunt the affect she was having on him.

After paying for the dress & leaving the store, they returned to the main concourse on the mall. Walking along, they passed a shoe store.

'Ooh, let's look in here.' Sam said.

Walking around they browsed lots of different shoes. Sam picked up a few different pairs of heels, before putting them back. As they walked along a shelf containing lots of different pairs of boots, Billy couldn't help but be mesmerised by them.

'What about these? Wouldn't they look nice with my new dress?' Sam said as she picked a pair of shiny black leather knee high boots.

'Err, yes. They're nice.' Billy stammered in his reply.

'don't you think they would look nice on me though? You don't sound too sure Billy?' Sam said.

'Oh yes, I think they would Aunt Sam. They would.' Billy replied, nervously. In his mind he had already pictured his sexy aunt wearing these boots and it was driving him wild.

Sam chose a size 7 pair & sat down on a bench. She removed her cowboy boots, passing them to the waiting Billy to hold. Then she placed one foot into a boot and shivered as her foot slid into position. She tugged the leather shaft snugly around her leg and pulled the zipper up to her knee. She then repeated the process on the other boot. She then proudly stuck one booted foot out towards Billy.

'Well? What do you think?' she said.

Billy struggled to string two words together and just mumbled.

'Billy? Are you ok?' Sam asked.

'Yes, sorry, they're lovely. Really nice.' He stammered.

She wiggled a foot around and then stood. Standing with her back to him, she looked around and lifted one leg behind her at the knee.

'Are you sure the heel's not too high?' she cooed.

'Nno, no, it's perfect.' He drooled.

He could feel his hands getting very sweaty as he held her cowboy boots. 

'If you approve then Billy, I think I'll take them' Sam said. 'Shall I wear them now Billy?'

'Err, it's up to you Aunt Sam.' Billy replied.

'And you're sure you like them?' Sam asked.

'Oh yes, I love them Aunt Sam. They've lovely.' Billy said in a dreamy sense.

'I'll keep them on then!' Sam said and she walked to the register. Grabbing a bag for her cowboy boots, she placed them in the bag with the receipt for her new boots.

'Shall we find somewhere to get a coffee Billy?' Sam said as they left the store.

'Sounds good to me Aunt Sam.' He replied, still in a daze with the images of his sexy booted Aunt in his head.

Grabbing his hand and tightly wrapping her fingers around his, she led him off down the concourse. 

Billy sat sipping his coffee, trying desperately to avoid eye contact with his aunt, the aunt whom he'd had a crush on ever since he could remember, the aunt whom was sat directly opposite him wearing the sexiest pair of black leather knee high boots he had ever seen. The tension in the air was thick.

'Billy?' Sam said.

'Yes Aunt Sam?' Billy replied, without looking up.

'Can I ask you something? And I want the truth.' She said.

'Err, sure.' He replied nervously.

'Do you find me attractive? I mean, am I still attractive?' she said.

'Yes, you're lovely Aunt Sam.' Billy replied.

'No, I don't mean lovely. I meant attractive. Do YOU find me attractive?' she repeated.

'Err. Well. I'm not sure if this is right us having this conversation is it?' Billy stammered out.

'Well that depends. You've not once looked at me properly since we left that shoe shop. And you're acting very strange. In fact, when I think back to it, you've always been a little nervous around me haven't you Billy?' Sam said.

'Erm, well, I guess so.' Billy replied.

Sam lifted her right boot so that it her toe started to rub on Billy's leg, causing him to almost jump out of his seat.

'You see? The slightest little touch and you turn to mush!' she exclaimed.

'Aunt Sam, this is really embarrassing. Please can we not go there?' Billy pleaded.

'But Billy, it's nothing to be ashamed about? You're my favourite nephew, you know I've always had a soft spot for you! Remember all those times you came and stayed over at my house during the holidays, and we used to snuggle up on the sofa watching films and stuff?' she said.

Billy thought back to those times, and how he used to snuggle right in with her, resting his head on her chest, holding her tightly. She really was his first love.

'Yes I know Aunt Sam, and you're special to me -- more so than you know! But it's still kinda embarrassing.' Billy replied.

'Billy, look at me.' She said. 'I know that feeling you get. I got it with your uncle before he did the dirty on me. It's perfectly natural you know?'

He gazed into her sexy blue eyes, knowing full well that he was under her spell. His stomach was doing cartwheels inside him. She took hold of his hand, gently letting her nails tease his skin.

'I want you know' she said.

'Oh Aunt Sam. You already know. I love you.' He replied, his heart thundering ten to the dozen. 'I love you, I love the person you are, I love the way you make me feel.'

'Especially when I'm wearing my boots huh?' she said smiling.

'Oh Aunt Sam, it's not just that. Yes I love your boots, but it's you that makes them so sexy. So appealing. I can't help it, but when I look at you I go all funny.' He replied.

'I kinda guessed that! Do you remember when you used to see me, and I'd hug you or sit next to you and rub my legs and boots against you?' she said.

'Remember? It's all I could think about for weeks afterwards!' Billy replied.

'I did it Billy because it turned me on too!' Sam replied.

Billy let his hand wander down to touch the shaft of Sam's boot. As he stroked her leather softly, she lifted her leg to allow him a better feel.

'Aunt Sam, do you not think it weird I have a thing for you and your boots?' He sighed.

'Not at all sweetheart. Why do you think I wear them all the time? I do to!' she replied.

'Shall we go and find somewhere a little more private?' Sam said, smiling. 

Does Auntie Know Best? Ch. 02



As they drove back to the house, Billy couldn't keep his eyes off of his sexy Aunt's legs. He noticed the creases in her shiny black leather and the way the light reflected off of them. As she pressed on the pedals, he watch intently as the leather went taught around her leg.

Sam reached across and wrapped her fingers into Billy's, interlocking them. She squeezed gently.

'I've been waiting for this Billy.' She said, as she traced her nails on the palm of his hand sending tingles through his body.

'Are you sure Aunt Sam? I mean, I really don't want to ruin what we have already.' Billy gulped as he nervously replied.

'Shhh. Just you let me take the lead ok? If you don't want to then I understand...' she replied to him, continuing to tease his hand with her nails.

'Err, yes, of course I want to but I don't want to offend you. You are my Aunt after all.' Billy said, feeling embarrassed.

'Listen to me Billy, this afternoon I'm not your Aunt. I'm your fantasy. Your desire. Your teacher & your lover. All rolled into one. If after we are done, it gets weird then at the very least we will have been honest with each other. True?' Sam replied.

'You're right Aunt Sam. I really do love you.' Billy replied, bringing her hand up to his lips and kissed it softly.

Billy turned the key in the front door and walked in. Good, no-one home. He walked into the living room, his stomach turning like cartwheels. Sam walked in behind him, dropped her bag on the sofa and walked up to Billy standing face to face with him.

She put her hands in his, again interlocking their fingers. Her eyes looked into his and he could see her tremble slightly. Their lips touched, gently exploring each others mouths. Their tongue's darting in and out, gently, softly. Their lips locked as she tightened her grip on his hands. His hand reached and touched the base of her neck, moving down her back until it reached her bottom, clenching, grabbing, pulling it into his groin. 

She could feel his arousal through his pants and she started to grind herself against him. Pulling herself away from him, still clenching one hand, she turned and led him to the basement door.

Walking down the steps, Billy was mesmerised by the sound of clicking heels on the steps. She walked over to the bed and motioned for him to sit. As he sat, she slowly unzipped her skirt and teasingly slid it down her long slender legs revealing a sexy black thong. She knelt down beside him and removed his shoes, jeans and socks.

Moving to the bed, she climbed up so that she was astride him looking down on him. Her hands reached forward and scrunched his shirt as she scrapped her nails up his torso onto his chest. His hands wandered down and gripped her boots. He felt the cold soft leather and gently rubbed her legs through it. 

As she let out a sigh, her hands reached up and unbuttoned his shirt. She leaned down and started kissing his chest, her tongue darting across his nipple as her teeth flicked on it. He jerked at this and gripped her ankles tightly, his hands now absorbing the leather feeling beneath him.

As his passion rose, he rolled her over onto her back and grabbed her wrists placing them over her head. Holding them in place with one hand, his mouth & lips nuzzled her neck & her ear. She raised one of her knees and began to grind it into his groin. 

His hand reached under her t-shirt and cupped one of her breasts. Using his fingers, he quickly found her nipple and rubbed it through her bra. Reacting instinctively, she wriggled free & quickly pulled off her t-shirt before laying back down on her back. 

Their eyes met again & their lips lurched for each others. As they kissed, Billy felt her wrap a leather boot across the back of his legs locking him into her. She teasingly rubbed the shaft of her boot up and down, while the heel teased and prodded into him.

Pausing for air, she looked up at him. His big blue eyes were filled with a passion she had not experienced for a very long time. 

'Billy, hold my arms up again. Hold me down while you kiss my body.' She gasped.

Billy reached for her wrist and with one hand held them back in place above her head while his mouth shot down to her cleavage. His lips and tongue slobbered away at her chest, nibbling, kissing, groping, while she continued to lock her legs around him. She could feel her pussy moisten, his ravenous passion now taking her over. 

She reached down with one hand and pushed his pants down, grabbing his arse and pulling him into her. Reaching behind her, Billy managed to unclip her bra and after removing it was presented with the most magnificent pair of breasts he had ever seen. Again, he buried his face into them all the while holding her other wrist in place tightly.

Her free hand was now scraping up and down his arse, up and onto his back, up to the base of his neck. 

'Mmmm you've done that before haven't you?' She sighed as he gently chewed on her nipple, rolling & squeezing it between his fingers. Billy didn't answer, he was too focused on the wonderful sight now before him.

Aunt Sam got up and stood at the end of the bed. Slowly, sexily, she removed her thong. She was now totally naked but for her sexy knee high black leather boots. She reached across to Billy and tugged his pants off. Walking round to the side of the bed, she lay next to him, her head resting on one elbow.

'You like my boots then Billy?' she asked.

'Yes Aunt Sam. Yes, I do.' He replied, mesmerised by the sight of his now naked Aunt laying next to him.

'So you don't mind this?' she said as she slowly lifted one boot and moved it to where his cock was springing at full attention. Smiling, she reached down and started to run her nails across his cock, rubbing it on the leather boot that lay underneath it. 

'Oh Aunt Sam!' Billy gasped as he felt the force of her nails rubbing his stiff cock against the leather. 

As she continued to tease, she swung the other leg round so that it trapped his cock between her leather covered legs. Expertly, she rocked them back and forth, slowly wanking him with her boots as her hands wandered up to his torso.

His head turned to be presented with one of her breasts sat invitingly next to him. His tongue reached out and licked on her nipple causing her to gasp. Her legs pressed together and he could feel her boots wanking him faster & tighter as he licked and kissed her.

He could feel his orgasm rising in his balls as she pumped him. He rolled her onto her back and moved down between her legs. As his face neared her pussy, he could smell the sweet smell of her juices. 

Burying his face into her pussy, he enthusiastically licked and sucked at her for all his life. Immediately, she clamped her legs around him and gripped the bed sheets with her hands.

'Oh Billy, that's it. Oh Yessss.' She started wailing as he licked and sucked. His hands wandered up to her smooth belly as his tongue darted across her lips. She reached down and grabbed his hands, holding him tightly. 

'Oh that's good, yes. Right there. Suck me there.' She cried.

'Yes. Billy. Oh yesss. I'm so close.' She continued.

Sensing that now was the time, he pulled himself up and without any warning, pushed his cock into her wet pussy.

'Oh fuck!' she creamed. 'That's it, fuck me. Fuck your booted Aunt!' 

Billy ground himself into her as her legs locked around his back, rubbing her leather all across him.

'Oh baby that's good, fuck me. Fuck me hard while I wrap my boots around you' she groaned, pulling him deeper and deeper into her.

Billy raised himself onto his knees and lifted her boots so that they rested on his shoulders. Thrusting into her, he could feel her tight pussy clamp itself onto his cock. He grabbed her legs and pushed her boots together, reaching up with his face and nose to inhale that same sweaty aroma that had captivated him before. Kissing and licking the black leather as he fucked her.

'Hmmm. Mmmm. Yes Billy. Fuck. Yessss.' She wailed as he continued to pump her, all the while his face was smothering her boots.

'Baby, fuck me doggy. Turn me over Billy. I want to you to use me. Now!' she screamed as she rolled herself onto all fours.

Positioning himself behind her, he held her arse cheeks while he guided his cock towards her now dripping pussy. Thrusting in, he waited a second while she adjusted herself.

'Hmmmm yessssssss' she sighed.

He withdrew slowly, then thrust back in.

'Yesssss. Fuck your booted Aunt. Fuck me.' She sighed in exhilaration. 'Grab my hair baby. Pull it.' She said.

Billy reached up and grabbed a handful of hair into a pony tail of sorts. Wrapped his hand around it and pulled on it as he thrust into her.

'Oh. My. Fucking. God!!!!!! Yes. Yes. Yes.' Was all she could say, her moans in between each word ensuring that she was in complete ecstasy.

'That's it baby, I'm coming. I'm coming.... Mmmmm, mmmm, Yessssssssss' she cried as her orgasm hit her.

Slumping down, Billy lay down next to her.

'Oh my god Billy. You are amazing. That was fantastic!' she panted as her hand reached across his chest and snuggled into him.

Beaming a huge smile, Billy put an arm around her. He could smell her sexy sweaty aroma, while her booted legs now tenderly draped over his body.

'Now, I think you've earned a little treat of your own!' she smiled as she snaked down his body. 

Reaching his still erect cock, she guided it into her waiting mouth, clamping down with her lips as she slowly started to suck him dry. Her hand wrapped itself around his balls as she expertly used her nails to scrape along. 

Feeling his own orgasm nearing, he was panting.

'Oh Aunt Sam. Yes, that's it.' He cried.

As she looked up at him, she started wanking his cock tightly, faster and faster positioning her legs beside his now throbbing cock.

'Christen my new boots for me baby. Cover them in your sticky load for me. I want to see you release it all over my black leather.' She cooed.

'Yes. Oh Yes. Oh Aunt Sam!' was all Billy could say as what felt like a gallon of spunk shot all over her boots. It shot all across the shaft, down to the ankle, even managing to hit her heel.

Reaching down, Sam removed her boots before bringing them up to her lips. Seductively, she licked and slurped all of Billy's spunk until her boots were pristine.

Sliding up and cuddle him, she wrapped an arm around him and sighed.

'Do you still think it's weird?' she said.

'No Aunt Sam. I think you are wonderful!' Billy replied, exhausted and near delirium.

'That's good!' she said as she cuddled him 'I have lots more pairs of boots for you to christen -- If you want me to wear them for you of course?!?...'