Sneaking in from Behind (Closed)

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xTerrax

Guest

"Okay so just need to set up the timer right...?"​

Ashley was fiddling with her phone, going through the settings and figuring out how she could possibly send a timed picture. While she was a mother, she was barely thirty-five years old, so she figured that age was no excuse. Besides, she was desperate to take this picture; it was more than just a lewd photograph, but an attempt to save her marriage that was in a very rocky place. You see, Ashley Simmons was a wife and a mother, but the former was something that she might have neglected a bit. Coming from a very Christian household, she never felt very...sexual. While this wasn't a problem at first, her husband, Jake, grew more and more frustrated that his wife wasn't interested in anything more than missionary position, with the lights off...and that was on a good day.

What is more, Jake was increasingly jealous of the fact that Ashley, his wife, often spent more time with her son's classmates, seeing as she was constantly at the school volunteering. This wouldn't have been a problem, if not for the fact that many of her son's friends were all over her. After all, Ashley (while she did not act like it) was a sex bomb; a gorgeous woman standing at about 5'7" tall, with big perky breasts and a perfect hourglass figure. But by far, the most noticeable feature of Ashley is her big, thick ass. It was a near obsession for a lot of men, including her husband. Again, this was the source of endless frustration from Jake, because Ashley would never, ever, let him so much as grab her ass. For her own reasons, she found it all so very crude.

But after a big fight they had about three days ago, just as Jake left to a business trip, Ashley felt compelled to move out of her comfort zone. This involved her going out and looking for some underwear that she'd never ever dream of wearing. In the end, she picked out a leopard pattern thong and wore it the second she got to her room, locking the door behind her in case her son decided to come in.

"Okay... so in this position...I uh..."​

Ashley, posing in her bed, bent over and pushed her ass out for the phone's lenses. With just a flash, she got up and blushed red, seeing herself in such a lewd, provocative position. It was definitely out of her comfort zone and she wasn't sure that she could send it.

Closing her eyes, she used the voice command of her phone...

"Send to Jake."

...

"Sending to Nate."

Nate?

"Oh god no!!" Ashley said, opening her eyes wide in panic and she frantically tried to stop the phone. Of course, this was impossible, but it didn't stop her from trying.

"Cancel! Cancel!"

But of course, it didn't matter. In just a few seconds, Nate - a friend of her son's - had just received the following picture:
 

Nate had certainly been one of the men who had oogled and been a part of the official Ashley booty club. After all while she did her best to hide that fantastically amazing ass of hers, not even loose pants could hide the definition of her full round ass, or delay his fantasizing about it.

He had her number only because he had wrangled it out of her a few months back, and from then on once in a while he would flirt over the phone with her, not to mention whenever he had a chance to in person. Of course, being the modest wife and volunteer with her son, Nate had joined every event that her son did JUST to get closer to him.

She had shut him down respectfully every time, but the truth was that only made Nate want her more. He was handsome, and though younger than her he had a year or so on her son and had him as his friend, though it was clear it was the MILF that he was really after.

He had been at home when the text first came... he had been in the shower. They had had a practice for the team and Nate was just finishing up his shower. Walking out from the bathroom wrapped in a towel though he picked up his phone and swiping to unlock, to say his jaw hit the floor was an under statement.

" Holy... shit."

He stared at the photo in disbelief for a few minutes. After all Ashley had shut him down every time previous to this. Instantly he knew it had to be a mistake... but a slow, evil grin crossed his face. Moving over to his bed he sat down on the edge as he typed back.

Well that's one way to get my attention... I knew you had to have the biggest and most beautiful ass of all time.

He hit send without a second thought. After all in Nate's mind, the game was now officially on, and he was going to take FULL advantage!
 
"Oh god, oh god..."

Ashley was sitting down, opening her computer as she desperately looked all over the internet for a way to delete a text message. Unfortunately each article and post seemed to be more useless than the last. Nearly whimpering from what had just happened, she nearly missed the vibration of her phone until the flashing light has captured her gaze. With a heavy heart, she anxiously opened up her phone and saw the text message:

Well that's one way to get my attention... I knew you had to have the biggest and most beautiful ass of all time.

"Nate, please delete that picture. It wasn't for you!" was all that she could muster back.
 
Nate could tell by the position that she was in that she must have intended the photo to be for her husband he would have to guess, but that didn't make a difference to Nate at all. Since she didn't reply right away he set his phone down again and taking off his towel he headed over and threw on a pair of black shorts.

As he came back though he saw the text and smirked.

Oh there's no way I am deleting that picture.

He was well aware that she was probably mortified but he didn't care. Feeling a surge of confidence he added

Besides, I knew that you secretly wanted to show your ass off... it's huge Ashley... or should I call you Assley.

Sending that he moved and reclined on his bed leaning against the headboard. Until she replied he was going to study and admire the fixture of his fantasies, namely her beautiful thick ass!
 
Ashley tossed herself in the bed, contemplating all sorts of ways that she could maybe get out of this mess. Maybe a lawyer? She had the money for it, at least thanks to Jake who worked hard to support this family. Still, what recourse would she have if Nate decided then to show people the picture? Even if she got Nate in big trouble, the damage would be done.

Oh there's no way I am deleting that picture.

"God damn it!" she muttered out loud, a mortified look on her face as she read those words.

Besides, I knew that you secretly wanted to show your ass off... it's huge Ashley... or should I call you Assley.

"It's not huge! Please Nate stop this. I'm a married woman." she typed back, nearly smacking her face for having said "It's not huge". While she wanted to defend herself, saying that probably gave Nate more of a reason to tease and torture her.
 
Nate was studying the curves and contours of her ass not to mention how that thong looked perfectly framing her beautiful hips and each ass cheek when he received the reply. He was SURE then that she was on the defensive about her own body.

Oh you're right, I shouldn't...

He of course was giving her hope, and yet within the next minute he had sent the next message

But I can't help it, you're wrong, you have a huge and beautiful ass Ashley, besides, I know you enjoyed taking the photo... your hips are turned up pushing your ass back begging for more.

He knew he was torturing her, but then again she had tortured HIM for much longer, so he didn't feel much remorse!
 
Nate was becoming more and more cruel, or at least that is what poor Ashley felt like when reading those text messages. The false sense of hope, the lewd language...it was nearly bringing Ashley to a panic attack.

But I can't help it, you're wrong, you have a huge and beautiful ass Ashley, besides, I know you enjoyed taking the photo... your hips are turned up pushing your ass back begging for more.

Did she enjoy taking the photo? Maybe.

But that was for her husband.

"Nate, this was for my husband. Please delete that photo. What do you want from me? Do you want me to flirt along with you? Just tell me and make this stop."
 
Nate knew that she probably thought that he was being cruel, but he considered it for a long few minutes. What exactly did he want out of this. He knew in regards to this he held all the cards, but she had to know he wouldn't delete the photo.

I don't care if it was for your husband, and I don't care that you want me to delete it. I'm not going to and if you keep begging I'm going to post it everywhere.

He took a break to consider it but added

There's a party this weekend, you're going to attend, and during the party I'm going to show you what I want Ashley. For now, you're going to use your phone to take another picture of your ass, but you're going to do it without the thong.

He wasn't asking, he was demanding, pushing her even further.
 
I don't care if it was for your husband, and I don't care that you want me to delete it. I'm not going to and if you keep begging I'm going to post it everywhere.


Her heart skipped a bit, as Ashley couldn't even think of what her next move should be.

There's a party this weekend, you're going to attend, and during the party I'm going to show you what I want Ashley. For now, you're going to use your phone to take another picture of your ass, but you're going to do it without the thong.

Ashley needed to do something; that much she knew. Already this picture got her in deep trouble and in her mind, there was nothing in the world that Nate could do in order to get another picture of her ass. That's when it hit her; she could outsmart Nate. Maybe play along with his fantasies and get something embarrassing? Maybe even make him see how ridiculous he was being?

"Can you first tell me about what you'll want at the party? Are you going to call me Assley or are you hoping me to go in as your girlfriend?"
 
Nate could tell that he was pushing his luck with her, but then again as she clearly considered that she could barter herself out of having to take that picture, he considered her own text. There was so many depraved dirty things he wanted to do to both her and that beautiful ass of hers that he had to admit he was a bit overwhelmed when she asked that.

No, everyone knows you're married, so going as my girlfriend would be out.

He was rational and right about that, but he smirked to himself.

I'm going to hunt you during the party. Every time you're alone, I'm going to be there, I'm going to make you show me that beautiful huge ass in private... and you're going to be man handled the entire night. Now that you mention it though Assley sounds like a good name for you for the party.
 
I'm going to hunt you during the party. Every time you're alone, I'm going to be there, I'm going to make you show me that beautiful huge ass in private... and you're going to be man handled the entire night. Now that you mention it though Assley sounds like a good name for you for the party.

The sound of being "hunted" somehow made things sound a little excited. Granted, just thinking that made Ashley feel sick to her stomach with sheer guilt, but in that second that she was true to herself, she somehow felt a slight twinge of excitement. She read the rest of his text, her breathing just slightly heavier.

"But where at the party will you get me alone? There's bound to be a lot of people. Are you going to drag me into a closet, or a room? And how are you going to man handle me? I need details Nate, otherwise you won't get that picture."

Of course, Ashley didn't want to egg him on, but she felt that if she texted him a bit more provocatively like this that she could fluster him into giving up.

Or at least...that's what she hoped.
 
The fact that she was clearly trying to get details out of him hadn't escaped his notice, nor did he mind all that much either. Even as he leaned back though his one hand was reading her text while his other slid into his boxer shorts, feeling how hot and hard he was getting.

Oh that's going to be the fun part. I might get you anywhere, shove you face first into a closet and hump your massive ass with my cock while I hold you there.

He of course was now rapidly revealing some thoughts and fantasies

I may drag you down onto a couch and force you to kiss me and make out with me right in the party. who knows... the night is going to be amazing.

He knew that she was probably trying to embarrass him, but he didn't feel embarrassed. He felt so fucking horny, though he added again.

Now Assley, you're going to tell me just how wet all this is making you... and if you lie, I will punish you even harder at the party.

How he would know was a bluff, but he was willing to think that she might not consider that!
 
Oh that's going to be the fun part. I might get you anywhere, shove you face first into a closet and hump your massive ass with my cock while I hold you there.


"Oh god..." she thought to herself, breathing heavier and heavier. A slight moisture going on her though, as a slight ache grew between her thighs, inside of her inner lips. She whimpered at the thought of something so crude, of being inside a closet secretly while Nate, someone half her age, would be dry humping her.

I may drag you down onto a couch and force you to kiss me and make out with me right in the party. who knows... the night is going to be amazing.

"Ugh..."

Somehow the thought of being forced to do something, such as kiss him and make out in the middle of the party, send shivers down Ashley's spine. She arched her back a bit, trying to fight off against the disturbingly lewd thoughts crawling in her head.

Now Assley, you're going to tell me just how wet all this is making you... and if you lie, I will punish you even harder at the party.


"I'm not wet...so maybe you'll have to punish me even harder at the party. But I'll just try to hide from you and not give you a change to get your hands on this huge ass that you love so much."

Her mind wasn't in the right place and this plan of her was rapidly backfiring...
 
Even with himself not being there, Nate could tell that she was feeling it. Her texts weren't as fast or as frantic to try and get him to get rid of the picture as before, and she was responding to him, sexting with him in fact.

As she texted that back though she probably didn't even realize that she revealed her lie in her own text.

If I have to punish you then you're lying to me Assley.

He knew that she probably didn't even consider that, but he smirked as she was playing back.

Just for that I am going to hunt you even harder... your huge ass is going to be mine.

He paused there and flipping to the camera mode of his phone, he turned the screen and aiming it at his groin he took the picture of the black boxer which was tented with a clearly almost eight inch long length tenting it.

Look at how hard you've made me Assley... I'm going to lick your ass, I'm going to finger it at the party, and right now, you're going to take that picture of your ass without your thong.

He hadn't forgotten it... and he wanted it from her before the debauchery of a night was ended for now.
 
If I have to punish you then you're lying to me Assley.

She read that text, all the while her skin was feeling more and more hot. A soft whimper escaping her mouth as she thought of all the dirty stuff that this man wanted to do to her. In the back of her mind, she wondered if this was the excitement that she was missing out on for her entire life...

Just for that I am going to hunt you even harder... your huge ass is going to be mine.


"Ooohhhhhh" she moaned, his hand moving between her legs, to feel how wet she was getting. Her eyes stared into the phone, watching a picture of a huge tent growing in what looked like to be Nate's boxers. They then opened wide, as she began to wonder how big it was.

Look at how hard you've made me Assley... I'm going to lick your ass, I'm going to finger it at the party, and right now, you're going to take that picture of your ass without your thong.

She squirmed on the bed, yearning for more.

"Tell me more and instead of a picture you'll get a video."
 
Well that offer certainly was more than he had considered possible especially with how conservative she had appeared with even their conversation.

As she texted that though he considered it carefully.

I will tell you more, but only by voice. You'll do your video live for me, and I will tell you all about what I am going to do to your fat firm beautiful ass.

He then sent her a link which would open up a private video sharing site on her computer, it was secure and wasn't being recorded but would live feed her for his viewing pleasure, meanwhile he had his phone ready to call her and tell her all about his dirty lustful desires.
 
I will tell you more, but only by voice. You'll do your video live for me, and I will tell you all about what I am going to do to your fat firm beautiful ass.

..

And that's how Ashley soon ended up setting up her phone to film herself.

Bent over her bed but still wearing her thong, Ashley's heart beat raced like no one could ever believe. Once Nate would open the link, he'd be greeted by the sight of Ashley's famously huge ass, covered by a flimsy piece of cotton. Of course, maybe he could even see the slight moisture, practically dripping down her thigh.
 
Nate waited patiently, and as he dialed into the number, the sight of her famously huge ass caused the first sound that she would hear from his end to be a deep gutteral groan of pure desire. Collecting himself though he grinned.

" Oh that's it... you're famous with your huge ass... but it's even better in person Assley."

His voice was thick with desire but he added.

" shake your ass for me... I can see you were lying to me, you're soaking right down your thigh. I'm going to enjoy hunting you... I'm not going to show up in a way you think... I'm going to find you and no matter where you are your ass is mine."

He breathed sharply, though added hastily

" I'm going to force you to kiss me, I'm going to drag you down onto a couch and finger your tight ass... your virgin ass i'm betting, but your not going to be when I am done with you Assley."

He watched her video, fixated as he was sure she was as horny as he was!
 
" Oh that's it... you're famous with your huge ass... but it's even better in person Assley."

Thankful that her son wasn't home yet, a soft, slightly high pitched moan escaped Ashley's lips. She stuck it out on the camera, pushing it back while she began sliding the thong down her cheeks.

" shake your ass for me... I can see you were lying to me, you're soaking right down your thigh. I'm going to enjoy hunting you... I'm not going to show up in a way you think... I'm going to find you and no matter where you are your ass is mine."

She then, as he commanded, began to lewdly shake her ass for him. Another moan escaped her lips, feeling her thong pulled halfway down just as she shook her hips, making her feel the tremble and jiggle of her ass, putting up a private show right there and then.

" I'm going to force you to kiss me, I'm going to drag you down onto a couch and finger your tight ass... your virgin ass i'm betting, but your not going to be when I am done with you Assley."

"Oh...oh...god...." she moaned, while she kept shaking her ass for him. Peeling off her thong, she exposed her huge ass to Nate, before tossing the underwear to the floor. At that moment, if Nate was looking, he'd get a good look of her pussy lips, pink and incredibly wet with her own excitement. She got back to the bed, shaking her naked ass before saying out loud "Please tell me more! What do you want me to do now to hear more?!"
 
Nate couldn't say he had a plan here. He was making it up as he went, but then again he did have fantasies that he had jacked off to for the last year or so.

As her high pitched moan came from her though Nate listened as he watched her ass push back and up, though even as she did the thong began to descend down her thighs he could hardly believe that the shy beautiful mother was willingly doing that for him!

As she lewdly shook her ass though her moan was met with his groan as he admired it.

" Oh shit yeah, look at that huge ass... I can see your beautiful ass shake Assley."

As she moaned and fully peeled off her thong, as she got back to the bed he considered her plea for more.

" Spread those thick thighs and finger your hot dripping pussy."

Only when she had did he continue with his descriptions.

" Oh shit... I'm going to force my fingers right into your ass on the couch... I'm going to keep you prisoner and make you cum with my fingers in your ass..."

His other hand was sliding up and down his cock as his voice was raspy and shorter with his clear lust. His eyes were fixated on her ass as he told her more about his desires for her, but he stopped there, wanting her to show him her reactions to what he was doing to her!
 
" Oh shit yeah, look at that huge ass... I can see your beautiful ass shake Assley."

Ashley continued her lewd display, shaking her ass for the camera. Her pace even picked up a bit, her cheeks trembling while the excitement made her drip on her bed sheets. Another moan escaped her lips, this one louder than the one before, just as her nipples began to harder within her bra. Her sexual drought, which she had considered a virtue for all these years, must have repressed urges for her. Otherwise, she probably would not be in this position...not that she minded.

At least not at this moment.

" Spread those thick thighs and finger your hot dripping pussy."

"Oooh..." she moaned softly, doing as Nate commanded and slowly parted her thighs. In doing so, the camera got a lewd display of her inner lips, aching with pure desire, glistening in the light with her excitement. Her fingers traced the outer contours of her shaven pussy, just as her fingers began to slip inside. Her muscles clenched at the single single, just as she slowly began to pump her finger.

" Oh shit... I'm going to force my fingers right into your ass on the couch... I'm going to keep you prisoner and make you cum with my fingers in your ass..."


"I'm...not going to let you..." she protested, although obvious to the both of them that she was just trying to hear more about how he'd do disgusting things to her body. She continued to pump that finger in, make a slight wet noise as she did so. The guilt inside of her grew, but so did the excitement which overpowered the former. "You want my big ass?... You're never going to have this..." she then added, slipping her finger out of her pussy just to slap her own ass for the camera. She then placed both her hands onto her bed, gripping on the sheets.

She was so close to cumming.
 
Nate groaned as he watched her huge ass shake... it was honestly a thing of beauty and was the center of his desires. Even as he watched her heavy thick ass cheeks shake with the force at which she was shaking her ass, and Nate certainly did notice how she picked up the pace. He didn't really give much thought to why she was doing what she was doing, mostly because he didn't care!

As she spread her thighs slightly he grinned as he saw her glistening shaved pussy lips.

" Ahh look at that, you even shaved your hot soaking wet pussy for me."

Though as she pumped her finger and protested, his voice was so thick with desire as he retorted to her.

" Did I say I cared if you were going to let me or not? I don't need your permission... not anymore."

As she said that and slapped her own ass he noticed how she slapped her own ass, but seeing how she was quivering, he was willing to bet that she was close to cumming right there on camera.

Even if you run, I am going to catch you, and I am going to make you take my cock inside your tight virgin ass Ashley... you're going to be mine, and just think, one more week and then all your dirty depraved thoughts will become reality."

He growled though as she could hear him calling her a fat ass slut, that her huge ass was all his, that no matter what she did he was going to fuck her ass and even more so that he was going to do it on camera... he put his phone onto speakerphone as he yanked his cock out and began to jerk himself off as he said all this, she knowing he was going to cum to the sight of her huge beautiful ass!
 
Even if you run, I am going to catch you, and I am going to make you take my cock inside your tight virgin ass Ashley... you're going to be mine, and just think, one more week and then all your dirty depraved thoughts will become reality."

Those depraved words didn't stop there. Ashley groaned and moan, hearing Nate's voice over how she was going to be his. Those objectifying words, over him calling her a fat ass slut and that her big ass was going to be his...it sent shivers down her spine. The turning point was when he described, in detail, that he was going to shove his thick inside of her ass. How he was going to dominate her body, how her body was all his for the taking. She never, ever imagined that someone would speak to her in that way and not for one moment did she think that she would actively enjoy it.

But here she was, her mouth open wide as she groaned and moan, her nails digging into the bed sheets while her legs shook. "NATE!" she moaned, shaking her ass in a futile attempt to stop herself. In just a few seconds, her orgasm hit; shivers running across every inch of her skin and her cum running down her pussy like an open faucet. She even collapsed on the bed, her knees making her push out her ass towards the camera, her face on the bed as she desperately tried to catch her breath.
 
Nate smirked as she took every comment with a wiggle or shake of her ass... how her body rocked and small little gushes of her excitement would dribble down onto her thighs... and even as he certainly told her how he was going to use his strong hands to pry her ass cheeks open and force his huge cock into her virgin ass, he could tell that was the tipping point.

" Fuck yeah ASHLEY."

With a final cry of her name Nate arched his own back, she having to imagine what he looked like as he came, though as she came so hard, he watched how she collapsed onto the bed.

" Oh shit that huge ass is going to be mine."

He grumbled as he caught his breath, but he added boldly.

" Reach back and spread your ass cheeks, show me the hole that's going to be dominated by me next weekend."

He knew she would... she was his slut now.
 
" Oh shit that huge ass is going to be mine."

She heard those words and somehow, felt a twinge of pleasure around her pussy, even though she had just reached her climax. The excitement subsided a bit, but quickly came back. Her body was only willing for more, but was actively craving it. How else could she explain her own actions, just moments after Tyler said:

" Reach back and spread your ass cheeks, show me the hole that's going to be dominated by me next weekend."

Her hands reached out to behind her, very slowly as if she was extremely hesitant. Within the span of a few seconds, her hands grasped her own ass cheeks (or at the very least, as much as she could handle) before spreading them apart. She showed him her asshole, Nate's goal for next weekend. Even now, she taunted him "I'll try to keep this away from you..."
 
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