The Bottom was Only The Beginning Ch. 01-02


Chapter 1

Their meeting was nothing special. They were both sophomores at the University of Wisconsin and found themselves to be more or less neighbors in the student area of Madison at the beginning of the fall semester. Josh was studying economics but wasn’t sure what her major was, regardless, he and Ashley’s schedules meshed such that he found himself running to campus at the same time as her nearly every Tuesday and Thursday morning. After a few weeks, they were exchanging courteous smiles and Josh found himself timing his walks to class so he could catch a glimpse of her as often as possible.

She didn’t dress to impress but she always managed to turn heads whether they were exchanging small talk or he was watching her from afar. She was a natural blonde and wore very little makeup but had a very deliberate style about her. With an unseasonably warm introduction to the semester, she typically wore lightweight dresses or casual shorts with a tank top. No matter how nonchalant her outfits seemed, there was always a hint of sexuality peeking out. Ashley’s shorts were dangerously short, accentuating her very long, toned legs and when she wore dresses, the fabric clung to her tight ass and firm breasts just enough to let Josh’s imagination run wild.

Eventually kind smiles turned to small talk and they got to know each other a bit. She had a boyfriend but promised she would “never marry a guy like him” and he had a long distance girlfriend that he had dated since high school. The small talk was innocent enough and they found they had friends in common. Inevitably, they made halfhearted promises to get together outside of their short lived walks and exchanged numbers.

It was near midterms when Josh finally saw Ashley’s number flash on his cell phone. He was organizing his notes on a Friday night when she called.

“Hello?’ Josh answered; he heard lots of shouting and a heavy bass line in the background.

“Josh? Hey it’s Ashley!” she shouted over the music. “I think I’m across the street from your apartment, you around?”

“Yeah” he replied. “Decided to take it easy tonight” he remarked, trying to play it cool.

“Ah, great! I could use a glass of water, mind if I came over? This place is packed and I can’t even find the sink” she yelled.

“Yeah, no problem, I’m in the basement on the North East corner, I’ll crack the door.”

Josh couldn’t help but feel nervous. It was late on a Friday night and she had obviously been out partying while he stayed in and prepared for a test that was still weeks away he hoped she wouldn’t find him lame. He tried to busy himself with dishes but kept his ears perked for any sign of her. Barely five minutes after she called, Josh heard footsteps descending his staircase and a knock at the door.

“Josh?” Ashley said as she pushed the door open.

He turned and saw her Ashley as he never had before. Gone were the seemingly conservative sun dresses and instead she was sporting what basically amounted to a black, one-piece swimming suit with fishnet stockings and large black heels. She had applied makeup very theatrically, with long fake lashes and glittering green mascara.

“Fuck those guys know how to throw a party” Ashley remarked as she closed the door. “It’s insane in there between the DJ and everybody rolling their faces off.”

“Sounds like something else” Josh said, “The music sounded pretty, uh, sweet on the phone”

Ashley smirked at him. “Yeah, it was pretty sweet; I’ve been dancing for hours. God, I need some water, would you mind grabbing me a glass? I can hardly see straight at the moment.”

“No problem” Josh replied.

Ashley sat down at the kitchen table across from him and busied herself playing with her tightly strung leggings.

Josh handed her a glass of ice water and watched her eagerly drink it down. There was a light sheen of sweat on her heaving chest that she absent mindedly tried to wipe away as she gulped the cold water.

“God that tastes good” she said, her chest still pumping. She placed the glass on the table as she ran her hands along her stockings. Either she was trying to make Josh lose his mind with her long strokes along her tan legs or she really loved the feel of her fishnets.

“God it’s intense in there, I almost lost myself dancing.” She said, looking at him intently for the first time. “I promised Taylor I wouldn’t take party hard without him but that place is fucking worth it” she said as she finished of her glass of water, ice clinking as she emptied it. Josh took it from her and went to fill it up as she stretched her long limbs, running her hands from her torso down her legs.

As Josh filled the glass again, Ashley watched him intently, running her fingers along the top of the one piece.

“So Josh, do you party?” Ashley asked

“Yeah, totally” Josh replied. “I mean you only go to college once right?”

“No, I mean do you party party?” Ashley said, as she reached for her clutch. “Have you ever taken these porno before?” She asked as she removed a small Ziploc with some pills in it.

“Dunno, what are they?”

“Ecstasy,” Ashley said “and some really fucking good pills at that”

Josh hadn’t taken ecstasy before but was eager to seem impressive. “Well…. Not in a while I suppose.”

“It’s some good shit, want to have a little fun, maybe dance a little?”

“Yeah yeah, I’m down” Josh replied anxiously. “It’s good you say?”

“Uh huh” Ashley uttered as she rose from her seat. “It’s really fucking good.”

With that, Ashley plucked a pill out of the baggie and placed it on her tongue. As she neared Josh, she looked him straight in the eyes as she reached up and clutched the back of his head, mouth to his. She kissed his lips hard and he felt his mouth open to hers. Her tongue snaked into his mouth and he felt a pill pass from her tongue to his. She withdrew and placed a hand over his mouth.

“Swallow” she ordered and Josh took the pill without any water. As he did, the satisfaction on her face was excruciating for him. “Good boy, now let’s hear some music.”

Josh put on a club mix and Ashley began to slowly sway. She smiled at him and grabbed the volume control, cranking it as loud as it would go. With that she grabbed his hands and pulled him to the middle of the kitchen. She turned and pressed her body tight against his in time with the music. She was being overtly sexual, bending over and rubbing her ass against his crotch, looking back at him with her mouth opened to a deliberate pout. She turned to face him, leaning in for a kiss before pulling away, grinning mischievously. The mixture of her grinding and coy looks was having the desired effect and as the drugs began to kick in, her seduction was even more intoxicating.

Josh began to feel the music more intensely, her touch sending shocks throughout his body. He ran his hands along her ribs and down her thighs, relishing in the electricity of their connection. Josh raked his fingers along the seams of her one-piece, feeling the warmth of her body against his.

“Told you it was good shit” Ashley said as her hand encased his. She leaned in for a kiss as she repositioned his hand to her firm ass. His thumb and index finger were within the crease of her ass and he felt the warmth of her crotch radiating through his hand. She forced his hand to squeeze her tight ass as she slid her tongue into his mouth. Apparently not satisfied, she moved his hand lower as she stared him directly in the eyes. He felt the moist warmth of her pussy through her skimpy outfit. Josh clutched her swollen wetness as Ashley gasped, her lips slowly breaking into a grin.

Ashley slowly gyrated on Josh’s hand in time with the music, one hand behind his head and the other on his waist, his fingers searching for more direct contact with her pussy.

“You promise to not tell anyone about this?” Ashley asked through short breaths, his fingers tugging at her underwear. “Because if you can keep a secret, I’m going to fuck the shit out of you.”

With that, Josh slid two fingers into Ashley’s sopping pussy. Her wetness coated his fingers and began running down his wrist as he curled a finger into her.

“I bet your girlfriend never turns you on like this does she? She’s not a little slut like me is she?” Ashley smirked, pushing him deeper into her. Ashley gasped as Josh pushed a second finger deep within her. “Does she let you fuck her like a whore? Does she do the kinky things a nasty little boy like you likes?”

Josh thought he would be put off hearing her talk about his girlfriend but it thrilled him at the same time.

Looking at him hard, Ashley curled a heel around his torso, his fingers deep within her. “My boyfriend says I get too carried away sometimes,” the tips of his fingers turning back towards himself, pumping in and out. “He says I get too dirty, that I ask him to do things that a normal girl wouldn’t ask for.”

Ashley turned, pushing her ass against his throbbing cock. She pulled her bathing suit to the side and began rubbing her finger in circles around her puckered asshole as he pushed a third finger into her wanting pussy.

“He says that it’s not natural for me to play with my ass.” Ashley withdrew her finger from her ass crack and slid it into her mouth. Coating it with saliva, she eased it out and placed it at the entrance to her hole. “He says only dirty whores like it in the ass.” Ashley pressed the finger into her anus, Josh still within her dripping pussy.

“But I can’t help it, I just like how it feels and I don’t think that makes me a whore for getting pleasure from it.” She pushed deeper, to her third knuckle. “Then again, if it does make me a dirty whore, I don’t really care.” Ashley began pumping in and out of her asshole. “You don’t think it’s too dirty do you Josh?” she asked while grinding on his crotch. He felt her finger pushing on the thin wall separating her finger from his

“No, I think it’s sexy” Josh replied, mesmerized by the sight before him.

“Oh, that’s good to hear, you think it’s sexy that I’m a little ass slut?”

“Yes ma’am” Josh replied, he wasn’t sure why he called her ma’am but Ashley smiled as the words left his mouth.

“You think my tight asshole is sexy do you?” With that, Ashley withdrew her finger from her ass and pushed it into Josh’s mouth, watching closely. “Show me how sexy you think my asshole is” she commanded and pushed her finger down Josh’s throat. “Good boy,” Ashley commented, pumping her finger in and out of his mouth. Josh sucked her finger and tried to swallow it. He curled his tongue around her musky finger as she pushed in and out. “Very good boy.”

Josh was starting to enjoy her praise and was eager to please her. Her touch felt heavenly and the music seemed to flow through their bodies

Ashley placed her hand on Josh’s chest and maneuvered him to lie on his back on the ground, she quickly removed his jeans and he found her standing above him, straddling his head.

“You promise you don’t think my little ass fixation is dirty?”

“No, I love the taste of your ass” Josh responded.

“Then taste.” Ashley spread her ass cheeks apart and lowered herself onto Josh’s eagerly waiting tongue. He couldn’t tell if she was embellishing or not but she enthusiastically ground her asshole onto his mouth. Her body shuddered and she let out a guttural moan. “Oh this is what I wanted, yes….” She hissed.

“I want you deeper; oh I want all of your tongue in my ass. Fuck me with your tongue boy.” Josh hardened his tongue and pushed against Ashley’s clenched anus. After sustained effort, he managed to push his tongue into her. He could taste the sweat mingling with her pussy juice as it dripped over her asshole.

Ashley leaned forward into a sixty-nine and took Josh’s erection into her mouth. He was so completely engrossed with pleasing her that the sudden pleasure caught him by surprise. She knew exactly what she was doing and managed to time her motions with the music. Josh doubled his efforts as Ashley reached between her legs to toy with herself. Ashley picked up her rhythm, strumming herself and intermittently taking Josh’s cock into her mouth. Her moans grew loader as he tongue fucked her ass while she pleasured herself. Josh felt her beginning to spray his face as an orgasm overtook her. Ashley’s moaning progressed to full yelling.

“God yes, lick my ass, fucking lick that whore ass. I’m going to cum, just keep….. Uh… just keep licking my ass, boy. “

With that, Ashley showered Josh’s face as she lost herself to the wave of a powerful orgasm. Ashley’s anus clenched and relaxed over and over again on Josh’s tongue. She coated his face and chest with her juices, moaning with pleasure as her body shuddered. Her orgasm had scarcely subsided before she began bobbing on his cock, sliding her crotch up and down on his face.

“You have to feel how incredible a tongue in your ass is, Josh. I promise you are going to like it.” Josh grunted and arched his torso up, trying to give Ashley better access.

“You want my tongue in your ass don’t you?”

“Ugh huh” Josh grunted though it was muffled by Ashley’s thighs clenching his head. Ashley began rimming Josh’s virgin anus while she stroked his cock, grinding on his face all the while.

“You see, it’s not disgusting, it feels good doesn’t it?”

“Yes.” Josh was surprised at how good it felt, Ashley tongued his hole hard while stroking his cock with a tight grip.

“My boyfriend won’t let me play with his ass, he says only faggots like their asses played with but I think it’s sexy, opening a boy up like a bitch.”

Josh responded to her words trying to get his torso closer to her face. Ashley was alternating between licking his ass and sucking his cock as he felt a finger pushing against his ass for the first time in his life. Maybe it was the drugs or maybe it was Ashley playing him so well, but he desperately wanted to feel her inside of him.

“What would your girlfriend think if she knew how badly you wanted my finger in your ass?” He thought he should be offended but his want for her simply kept increasing. “Would she think you’re a faggot or just a pervert?” Ashley noticed his response to her words and actions and was further encouraged.

“It seems you like it in the ass as much as I do, don’t you?” Ashley pushed her finger into Josh’s ass. He was conflicted by sheer lust and shame for his want at the same time.

Ashley pushed deeper and began pumping in and out while taking Josh’s cock deep in her throat. The feeling was incredible and unlike anything he had ever experienced.

“Maybe he’s right, maybe only faggots like getting fucked in the ass like this. Maybe this is what it takes to get a homo off, sucking his cock and fucking him in the ass at the same time.” Ashley began pumping faster as Josh’s muffled moans reverberated between her thighs

“Are you going to cum while I fuck you in the ass?” Ashley asked. “Are you going to cum like a little faggot?” Josh was lost in a wave of emotions but was blinded by want. He humped the air blindly, searching for release. Ashley laughed cruelly. “Ha ha ha, you are! You are going to cum like a faggot bitch!” “Cum faggot, cum while I fuck your ass and suck your cock.” Ashley’s mouth engulfed Josh and he was lost in one of the most powerful orgasms of his life. His entire body shook as he spewed into Ashley’s mouth. For all of her bold talk, even Ashley wasn’t prepared for the amount of sticky cum spewing from his cock.

As the aftershocks subsided, Josh lay in a haze as Ashley sat up and began rummaging through her purse. Noticing him stirring, she turned and put her mouth to his, unleashing a flow of warm semen into his mouth. Josh had never tasted cum before and was repulsed at the idea. Ashley spit what remained onto his face and held a hand over his mouth. She nodded and mouthed “swallow” with a grin across her lips. Begrudgingly, Josh swallowed the massive load he had deposited in Ashley’s mouth.

Some of the spit and cum that Ashley had spit on him had managed its way into Josh’s eye and he was having trouble seeing. At the same time, Josh kept swallowing his saliva trying to get the aftertaste of himself out of his mouth. He then felt Ashley’s playing with his spent balls before moving her hand lower towards is recently violated ass. She easily slipped two fingers into his ass and Josh forced his eyes open as well as he could.

“I think I’m going to have some use for you, boy” Ashley remarked. “Smile, bitch.” A flash of light temporarily blinded Josh as he realized Ashley had taken a photo of him, covered with semen and her fingers up his ass.

“Insurance” Ashley noted and with that she grabbed her purse, adjusted her disheveled leggings and primped her hair. She dialed a number while still slowly toying with Josh’s ass.

“Hey Taylor, I’m at Chandler and Orchard, Meghan was having some sort of breakdown but I think she’s fine now.” Ashley leaned close to his ear while holding the phone at arm’s length”…and I got my ass tongue fucked by a boy I barely know and covered his face with cunt juice before he came in my mouth.”

Placing the phone back to her ear: “Uh huh, sure, baby. Mind meeting me outside, I’m ready for bed. Thanks.” after a pause she laughed “I think I can do something about that for you. Great, see you soon then.” Ashley stood up and blew Josh a kiss as if it was the most natural thing in the world. Her brazenness was astounding to him.

Ashley let herself out and Josh stole glances of her waiting through the blinds. When her boyfriend arrived, he watched as she kissed him passionately with the mouth he had just came in. To his amazement, he witnessed her massaging the crease of her ass as she made out with her boyfriend. He wondered if he noticed anything different about her taste. As their kiss broke and they began to walk off, She turned back and gave a Josh a wicked knowing grin.

Chapter 2

Josh didn’t see Ashley for the next two weeks on their typical route to class. The memories of her impromptu visit were racing through his mind constantly but he was nervous that she had changed her mind and was avoiding him. Hey couldn’t concentrate on classes and anything his girlfriend said on the phone seemed unbelievably droll to him. He couldn’t stop thinking about the way Ashley had turned him on that night.

Another week passed, Josh was woken by his phone ringing. It was nearly 2am but any anger Josh had was quickly dismissed when he saw that it was Ashley calling.


“Miss me?” Ashley responded.

“Of course I have.” Josh was embarrassed by how enthusiastically he responded.

“I bet you have you filthy little boy, have you been dreaming about my ass the same way of been dreaming about yours?”

Josh was at a loss for words.

“I’ll take that as a yes. I bet you’ve even been playing with your asshole remembering how I got you off, isn’t that right?”

“Yes…” Josh answered meekly. He had been playing with his ass at night when he masturbated.

“You don’t have to be embarrassed; lots of faggots finger their own ass when they jerk off.” Again, Ashley’s voice had a strange effect on him, the degradation excited him and he felt the blood rushing to his crotch.

“Tell me boy, have you jerked off thinking off my asshole?”

“Yes” he replied

“Naughty boy, I hope your girlfriend doesn’t find out” Ashley let her words hang. “And tell me, how badly do you want my ass?”

Josh was lusting at her every word by this point. “More than anything, I’ll do anything for your ass.” Josh took his hard cock out of his jeans to try and get some relief as she toyed with him.

“I thought you would, but you know that I’m a very, very dirty girl and I might ask you to do some very filthy things to get inside of me, you don’t mind do you?”

“Yes, I love how dirty you are and I’ll do the filthiest things to please you.”

“Good boy, now you can prove it. I’m outside.”

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