The Downfall of Ash

The Downfall of Ashley

Ashley wasn't happy. She should be, and she knew that, but she just wasn't. She was 33, had an okay career that she didn't plan to pursue forever (but paid the bills), and she had a good-looking boyfriend that she lived with. Craig was one of the nicest, funniest, and most charming guys she had ever met. She legitimately felt lucky to have him -- he looked like a Disney prince and was everything she ever wanted in a man.

The sex was great....at first. Over the years, however, it had gotten stale. Well, stale may have been an understatement -- she hadn't been touched in months and it was starting to have an effect on her self-esteem. Ash knew she was a good-looking girl. She saw the guys checking her out, she saw it in the mirror, and she knew her friends weren't lying when they often complimented her. She was petite at 5'0" and 100 lbs, fit from yoga and running, and her shoulder length brunette hair framed her face perfectly. Her tanned skin didn't hint at her age and she knew she SHOULD feel good...but she didn't. She felt neglected and unwanted.

"Maybe he's cheating on you?" Aja, her closest friend offered. Ash wasn't sure and she knew Aja pretty much always thought the worst of men in relationships. For good reason, Aja was strong minded, constantly single, insanely attractive, and had her share of taken men. Aja's suspicion raised Ash's curiosity but she honestly couldn't see Craig having a girl on the side. She'd kind of be glad if he did as what she suspected was far worse for her self-esteem: she suspected he just was no longer interested in her and had turned to porn for gratification instead.

His long showers, late nights at the computer, and browsing history all almost all but confirmed this. The nights he thought she was asleep beside him and would sneakily stroke to videos at low volume on his phone. In her mind, this was even worse -- she didn't even compare to some girls that he's never met before and who probably would never give him a second glance. But she couldn't open up to Aja or anyone else about that, it was too embarrassing and degrading. Instead she silently carried on in a sexless relationship, feeling worse about both herself and the man she supposedly loved.

Ash's decline was not lost on Aja. She invited her out more often and they started partying -- hard. Ash was no stranger to recreational drug use but she had mostly left that behind her in her 20's. But she had to admit, the late nights out at shows and concerts, capped off with rolling on molly or high on coke really did help her feel better and really gave her something to look forward to. She also looked forward to the confidence boost that seeing Drew gave her.

Drew was Aja's ex of sorts and they remained close friends. Ash didn't think they ever had a serious relationship but definitely enjoyed an off and on again very casual relationship. A casual relationship that Aja couldn't help but gush about over various brunches over the years. The girls all knew about Drew's size, prowess, and girth, but that wasn't what interested Ash -- it was the fact that he actually paid attention to her. He laughed at her jokes, smiled when they talked, and made casual comments about how hot she was at all the right moments. His bold but casual touches to her legs, arms, or lower back made her heart beat faster and gave her that tingle down there that she had been missing for years. And she really, really appreciated the attention. He wasn't as good looking as Craig -- taller but skinny and definitely not a Disney prince, but he was attractive and she felt a definite attraction, although one she knew she would never act on. She didn't even entertain the thought until the texting started.

Ash was on her way to meet Aja at an afterhours when she received a text from a strange number. Aja's phone was on the verge of death and she borrowed Drew's to reach out. After the night passed the texts came coming -- innocently enough although Ash made sure to save the contact as "Becca", Aja's sister...just in case. She didn't think Craig would go through her phone and she had nothing to hide but people take things different ways and no point in being reckless, right?

But over the coming weeks the conversations escalated. Slightly at first -- sly sexual comments, inappropriate jokes. Ash always pretended to be shocked but she wasn't and she was actually still quite enamoured with the boldness. Besides, it wasn't anything too bad -- just harmless flirting. Until that fateful Wednesday night when her phone chimed to Drew's text "You up?" Ash laughed slightly, "Of course -- it's like 9:00" . She didn't laugh at the next text -- A picture of Drew's cock. He was on his bed, the shot of the stomach down, completely naked and with his hand at the base of the largest, thickest cock she had ever seen ...and it was an obvious state of arousal. Extreme arousal.

Ash was shocked. She couldn't breath. She switched her screen off as quickly as she could and glanced at Craig across the room, his eyes still on the TV. She was flushed and her chest was tight. She was upset. She was mad. She was partially disgusted. She got up and walked to the bathroom across the apartment, and as she did so she realized she was also extremely aroused. She closed the door behind her and turned on the tap. She brought her phone our and started texting wildly: "wtf? You can't do that". Almost instantly, Drew chimed back: "Do what 😉?" She rolled her eyes in frustration and took a second to find her words before typing "You know what, you can't send me a picture of your hard dick to me. Super inappropriate and super unwelcome.". It was a longer pause before he texted back "Sorry, couldn't help myself. Apologies". And to that she didn't know what to say. She put her phone back in her pocket and walked out but only after scrolling up slightly to take a more in-depth look at the picture he sent -- was that him? Dude was a freak. She collected herself and left the bathroom for another uneventful evening on the couch.

That night she lay in bed with her mind racing. The picture and exchange coming back to her. Was she too harsh? She didn't think so but she also thought that part of her reaction may have been less in response to what Drew sent and more in response to how her body responded to it. It was just...well, really fucking hot that he just sent it like that. Ash wasn't so much into dick pics but she did enjoy the attention and kind of appreciated that he was obviously thinking about her while he was pleasuring herself. And soon Ashley realized she was wet. Really wet. She reached down and was even surprised herself by how obviously aroused and sensitive she was. She rolled over to Craig, kissed his neck, stirring him awake. She kissed down his chest, over his stomach and down to his cock. He was semi hard and Ash had always loved pleasuring men with her mouth. She took his semi flaccid dick in her mouth, taking him as far as she could while he moaned. She bobbed her head under the covers, hoping he would become more erect but he never did. She caressed her fingertips over his balls and up his shaft, soon stroking his semi-erect shaft slowly in hopes of getting him more erect. He was obviously becoming more excited and she increased the pace of both her bobbing and her stroking until her hand was moving rapidly.... yet, instead of getting harder he came. His semi-hard cock exploded into her mouth, releasing a teaspoon of warm salty liquid before he rolled over and fell back asleep. And disappointed, Ash lay next to him and spread her legs -- rubbing her clit to climax with his taste in the back of her throat.... all the while thinking of another man.

Ash woke up disappointed, got in the shower disappointed, and got dressed in the same state of disappointment. She said goodbye to Craig as he went out the door to work and started getting things together herself. She opened her phone and there was another message from Drew from the night before at 10:45 pm. She opened the thread and all the shock of the night before returned. The text was simple and short: "Is this more appropriate?" and the picture underneath was much the same as before -- Drew taking a picture from his stomach down, except this time his cock was soft and spent, laying on his stomach in the biggest puddle of semen Ashley had ever seen. She stared at it and felt like the room was getting hotter. Her ears prickled and she knew she was getting flushed.

Ash was late to work that day. She told her coworkers that it was because she was dealing with a flood from a dishwasher. She didn't feel guilty lying -- it would have been ridiculous to tell them the truth and admit that she was late because she had to make herself cum twice staring at the pictures. Besides, it was a convenient excuse that allowed her to return home at lunch, remove her skirt, lay on her bed, spread her legs wide and slip two fingers into her tight pussy while thinking of taking Drew's impressive cock deep into her mouth. It was the longest lunch she ever took.

Things progressed rapidly from there. The flirting, the inuendo, the pictures. Ash never sent any and always playfully chastised Drew but never outright told him no again. But she still felt guilty and knew she would never hook up; she just appreciated the attention. The problem was she didn't know how to explain that with him. Honestly, she was pretty stressed with the entire situation and she hoped she wouldn't have to him on Friday when she was hanging out with Aja.

But of course she did, and of course her heart started racing when we sat at the table at the show. And of course all those mixed feelings, as well as those fucking sly smiles he kept shooting at her had her on edge and she had to drink a little more to take the edge off. And of course once she was a little too tipsy she wasn't going to say no to a couple of doses of MDMA -- molly was just what she needed to feel better. Besides, she felt so much closer to Aja, Drew, and her other friends than she did to Craig -- who gave a fuck? And why would she say no to going to the after party at Drew's friend's place in the sketchy part of town? What else would she do? Go home and watch Netflix waiting for Craig to get home from having beers with his friends (more realistically she would tactically go to sleep before he got home and she was wired and wouldn't be able to sleep anyways).

And you know what? When she got there she didn't care that the place was a flop house with a dirty carpet and a musty smell, she was having a great time. The drinks made her feel so good and so did her friends. Even Drew, as much as she hated it, she loved the way he was touching her again -- hand on the small of her back leading her in, hand on her thigh as they sat by the makeshift bar. She couldn't believe she was so torn over the whole thing earlier -- this felt right and, well, it felt great. She never wanted it to stop, which is probably why she followed Drew into the bathroom when he offered her coke.

And as the door locked behind her it just felt right. Just as it did when Drew leaned in to kiss her after she hit her line. Right enough that she kissed him back, encouraging him to slip his tongue deep into her mouth. And it felt right when he pulled her shirt and bra down, haphazardly unleashing her very, very hard nipples. She liked the way he looked at them before kissing her again -- it made her feel sexier than she had in years. She liked his hand reaching behind her, grabbing her ass and pulling her closer. More so than she liked him roughly pushing her against the wall and slipping his hand down the front of her jeans, but she felt the excitement that came with being thrown around like that and fucking loved how he moaned into her mouth in approval as he felt her freshly waxed pussy, as hot and wet as she'd ever been (why had she waxed it, she thought to herself). And she must have moaned back because he was certainly encouraged to slide a finger into her...and then another, and yet another, making sure she felt stretched as he kissed her deeply. And it all felt so good. So good that, minutes later, she lost her vision slightly while she came as hard as she ever had. And then the guilt hit her and she felt very, very bad.

Ash didn't really remember leaving the room but felt like she was having a panic attack and needed to find Aja who, as always, was somewhat dismissive of her problems as she chased some guy. Ash didn't want to tell her what happened -- she could still salvage her self-respect -- but she pleaded with her to leave and her "bff" didn't seem to concerned. "Just sit tight and hang for a bit, we can leave soon." Aja told her softly as she passed her another drink. "This will help" she winked as she sprinkled another dose of molly into Ash's drink. And Ash took it, and laughed at Aja's jokes and comments about the attire of those around them. And slowly Ash started to feel comfortable again. Comfortable enough to make eye contact with Drew when he came back. And to smile when he apologized for pushing things too far. Comfortable enough to apologize for running out and appreciating it when he understandingly shrugged it off and admitted that he was just concerned for her. Ash felt comfortable again...and free...and loved. In fact, she wouldn't change anything about where she was or who she was with. The only thing she would change was her underwear, which was still extremely wet although decidedly less warm than previously. And the night went on as the molly ramped up and Ash really truly enjoyed herself. The shame lingered but the drinks and drugs helped Ash push them to the back of her mind.

Drugs and drinks are good at that -- helping us move past our shame, numb it. So much so that Ash made the same mistake twice. As she came out of the bathroom approximately an hour later she saw Drew standing there, waiting for her. An hour earlier she would have been angry or apprehensive, but now she was just glad to see him, looking forward to more attention. And when he grabbed her by the hand and guided her to the bedroom down the hall she was actually sort of excited. Maybe more apprehensive with every step towards that foreboding door, but excited as her inhibitions had melted away quite a while ago.

As the door shut behind her and Drew pushed her against it she welcomed the taste of his mouth again, welcomed his hardness grinding up against her. She wrapped her legs around him, letting him support her weight -- he was remarkably strong. She felt tiny, petite, and incredibly desirable and she loved it. The fear and apprehension didn't set in until he untangled himself from her legs, set her in front of him and gently, but firmly, pushed her down onto her knees by her shoulders. Fear, apprehension, and molly-fueled excitement as he looked down at her and softly said "I think you owe me" as he unbuckled his belt and unzipped his pants.

Honestly, Ashley would have been incredibly insulted hours ago but she was maybe a little too far gone. She was incredibly aroused and curious about what Drew was packing -- she wanted to see that cock in person. She wanted to feel that hardness in her hands and taste him. So, as he pulled out the largest cock she had ever seen in pictures or in person she instinctively and submissively opened her mouth and moved forward to take him in. And she tried her best, but she was a small girl and he was very big, both in length and girl. Her jaw was sore right away from being forced open so wide and she could hardly get half way down his shaft before it was unmanageable. But nevertheless she tried, moaning as his musk filled her nostrils and his taste permeated her mouth. She looked up at him, seeking approval in his eyes as she brought her hand up to his shaft and stroked wildly but beyond his light moans she saw frustration.

Drew looked down at her and whispered "Lets get more comfortable, that might make it easier". He helped her up and guided her to the edge of the bed, removing his pants completely and sitting on it. He spread her legs and gestured for him to get on her knees in front of him and she did, obediently. She looked up at him and admired him stroking his unbelievable cock slowly in front of her and she felt ashamed again -- not because she was a taken woman but because of how embarrassingly and primally she wanted to make him cum. And that was only reinforced when he reached down, guided her face to his and kissed her deeply before whispering in her ear how badly he'd wanted this.

The encouragement did it's job and Ash hungrily devoured his cock. Kissing the head and shaft as slowly pumped it with her tiny hand. Eventually getting the courage to go deeper and deeper. Ash was proud of herself -- she felt like she was on the verge -- triggering her gagging mechanism but not quite getting there, seductively stroking while her warm mouth took the rest of him in. The hand on the back of her head only further made her feel close with Drew and made her feel satisfied that she weas doing a good job.

When he grunted at her to touch herself she couldn't help but abide -- her pussy was so uncomfortably hot and wet. She scrambled to get her jeans down but only got them halfway before the sight of him stroking his saliva-slick cock and looking at her set her over the edge and she took him back in her mouth. She was peaking from the MDMA and every touch and sensation was so much. The ebb and flow of the drug combined with the situation had her basically in a frenzy. Every small touch on her clit sent shocks through her body and she had to concentrate more than she ever had to just to make sure she wasn't ignoring Drew's cock.

She took the hand on the back of her head again as a sign of approval rather than frustration. She was wrong in that. Gently at first, and then more menacingly and urgently Drew took control. Pushing her down on her down strokes a bit farther than she would like to go -- again gently at first and then with more force. The first time she gagged she took it as an accident. The second time she looked up at him through her watery eyes and became worried -- he was staring at her with menace. Her eyes were forced closed soon after when he pushed down harder, pushing deeper into her throat than any man had dared to before. She gagged loudly and a torrent of saliva poured out of her mouth and over the hand she had supporting the base of his cock. Her body responded strangely as her pussy likewise released a much smaller torrent of liquid over her hand cradling her pussy. Her enhanced tactile senses made sure she felt every drop in both cases but she had no time to marvel at it as soon her head was forced even deeper and with more force as Drew took what he wanted from her.

Ashley moved the hand from the base of his cock to the floor in an effort to support herself. She tried to thrust her head back up to no avail, he held her down, forcing even deeper. She did not move her other free hand from her pussy. With each thrust down Drew held her head slightly longer, until the vision at the periphery started to blacken. He started to accentuate by thrusting up powerfully with his hips. Another torrent was released from her mouth as she gagged uncontrollably.

Ash's head was pounding, her throat was sore and stretched beyond measure, her eyes were burning. And yet, he didn't let up -- quite the opposite actually. Her body heaved and spasmed as he pulled her down with both hands until her lips were at the very base of his shaft, tasting her own saliva mixed with his pre-cum. For split second she thought she was actually going to die there and the molly made sure she felt every sensation to the fullest.

When Drew finally let up she thought it was over until he pulled her head back down, thrusting just as he had done before. The third time she still had that faint hope, trying to plead when her mouth was finally free...but all she could do was gasp for air. Soon the hope was gone. Every time he forced her head back down a little bit of her was taken away and she became consumed with the sensations. The taste, the smell, the burning, the friction from her hand against her clit sending electric shocks through her tense body. She felt empty without those sensations.