Jill Goes To College

Jill's arms strained under the weight of the wavering stack of books she held as she made her way down the narrow hallway. With each careful step, she struggled to prevent her grip from giving way while maintaining the precarious balance of the teetering pile. As she reached the closed door of her dormitory room, she firmly planted her chin against the top of the stack and lifted her knee from the bottom to help support her tired, shaking hands. As she fished into her pocket, rummaging for her keys, Jill was too preoccupied on the task at hand to notice the subtle moaning coming from within the room.

"God damn history paper," she muttered to herself as she fumbled with the keys before pinching her fingers around the small metal object and pulling it from her pocket.

Bracing the stack of books between her knee and chin, Jill slid the key into the hole and turned, using her bodyweight to push the door open. Stepping in to the small dimly lit room, the heavy door still held open by her leaning body, she froze as her eyes fell upon her roommate's bed. Amid the tussled blankets, her roommate Haley was situated on her hands and knees as some unknown male knelt behind her assailing her with frantic thrusts of his well muscled pelvis, filling the room with the sound of repetitious, wet slaps.

"Oh my god!" Jill blurted out, stunned by the obscene sexual display that now lay before her inexperienced eighteen year old eyes.

"Oh...Hey...Jill," Hayley managed to force out between thrusts, as she turned her head to acknowledge the recent entry of her shocked roommate.

Staring dumfounded with mouth agape for a few agonizing seconds, Jill soon regained her senses with enough form to pull her widened gaze away from Haley's sweaty, lurching body and stumble backwards out of the room, letting her books topple to the floor.

Scrambling to prevent them from spilling out into the corridor, Jill fell to her knees grasping with futile hands as the door slowly closed shut in front of her. Exasperated with the effort, she sank down between her knees in frustration and stared at the remaining book in her hands before slamming it to the floor as well. Shaking her head in frustration, she stared down at the copy of The Decline and Fall of the Roman Empire looking back at her, before slowly gathering up her scattered belongings.

"Haley, Haley, Haley," she muttered to herself in reference to the many promiscuous exploits of her sexually adventurous roommate. "I should have known."

After regaining her composure, Jill settled into a comfortable cross legged position as she patiently awaited the exit of her roommate's visitor. Letting out a prolonged, exasperated sigh, she flipped open her notebook and began scribbling down ideas for her recently assigned essay.

Exactly twenty seven minutes later, the door opened and Haley's "friend" stepped out into the hall, zipping up his pants as he glanced down with a satisfied smirk.

"Uh...see ya later," he said, blushing slightly as he turned abruptly and headed off down the corridor.

Jill shook her head, flipped her book closed and hauled herself to her feet, placing her hand against the slowly closing door, just as it was about to click shut.

"Hey roomie!" Haley greeted cheerfully as Jill stormed into the room and slammed her backpack down onto her bed.

"Jesus Haley," she fumed, casting her roommate a scornful stare. "Can't you at least put a sock on the door or something?"

Haley laughed as she reclined on her bed, stretching out amid the ruffled sex-stained sheets and blankets.

"What's the matter Jilly?" she asked with a sarcastic smile. "Didn't you enjoy the show?"

"Ummm...No!" Jill countered back. "That image is going to be burned into my mind forever."

"Well, you should be glad that you didn't walk in a few minutes earlier then. That would have really damaged your innocent little mind."

"Yeah,I bet," Jill returned."So was that that guy?"

"Oh just some guy from the swim team," Haley answered with her characteristic nonchalance. "Great ass...but a bit of a premature ejaculator. He even tried to..."

"I don't want to know!" Jill snapped, cutting her off and throwing her hands up in frustration.

"Oh come on Jilly!" Haley stated emphatically. "Lighten up. You know...you could use a little of what I just had. It might help you to relax."

"I don't need to relax! I need to get started on my paper. And unfortunately, I've been spending the last half-hour sitting in the hallway because my roommate was slutting it up with some...guy...again! And...stop calling me Jilly!"

Jill closed her eyes and fell back on her bed, immediately regretting the words that had just left her lips.

"Haley...look, I'm sorry. I didn't mean that..."

"It's okay," Haley reassured, joining her roommate on her bed. "I know you're stressed out. When is your paper due?"

"The 20th," Jill said softly as she ran her hands through her hair.

A brief moment of silence ensued, followed by a loud, thunderous laugh as Haley clutched her sides and pumped her legs in hilarity. Jill turned and shook her head in confusion.

"Next...haha...the 20th?"'

"Yeah," Jill squeaked, pursing her lips into a pouty expression. "Why?"

"That's like two weeks away! You still have forever to finish your stupid paper."

"It's not that much time," Jill shot back, staring down her laughing roommate. "I have to make an outline, and get some more references and..."

"Jill," Haley stated bluntly, her humorous expression turning surprisingly stoic. "It's Friday. Your essay isn't due for another two weeks. You're going to be okay."

Jill took a deep breath and fell back onto the bed as she processed her roommate's flighty advice.

"Why don't you come out with me tonight?" Haley pressed on, slapping her hand against Jill's thigh in a playful, light-hearted manor. "There's a party off campus. It's supposed to be really good. I know a couple guys that are going to be there...."

"I don't think so Haley," Jill said, waving her hand in dismissal. "I don't really need to be set up right now."

"Oh, I beg to differ," Haley retorted, hopping back up to her feet. "I think you need to be set up more than anyone I know."

"Oh yeah? And why is that?"

"Because sweety," she said, giving her a concerned look. "You...really need to get laid."

"Haley," Jill groaned, turning away in disappointment. "You know my situation."

"What situation?" she blurted out emphatically. "Jill, you're a hot, nineteen year old college girl. You should be having the time of your life right now."

"And...having the time of my life means getting laid by a bunch of strange guys?"

"Well,it wouldn't hurt!"

Jill smiled and shook her head.

"Oh come on," Haley continued. "I thought you were done with all that religious stuff."

"That's not the point. I still want to wait until I get married before I have sex."

"Jill, Jill, Jill, Jill, Jill," Haley muttered, pacing across the room. "You have no idea what you're missing."

Jill shrugged her shoulders.

"It's not like I haven't thought about it, but...."

"But what?" Haley pressed. "Even if you don't want to have sex, there are other things you can do."

Jill cast her roommate a sceptical glance.

"Uh, yeah..." she began, looking bashfully down at the floor. "I don't really have any desire to suck a dick."

"Haha," Haley, laughed out loud. "Wow. I don't think I've ever heard you say 'dick' before."

Jill returned her laugh with one of her own.

"And..." she continued, placing her hands on her hips in an authoritarian pose. "Sucking a dick can actually be pretty fun."

"Yeah, I bet," Jill shot back, her expression retaining its sceptic appearance.

"Well...," Haley muttered as she flipped through the clothing in her closet. "You know...There is one more thing that might give you a little...gratification."

"Oh yeah? What's that?"

Haley glanced back over her shoulder, casting her roommate a devious glance.

"Think about it," she said, her eyes scanning downward as she wiggled her ass in a provocative manor.

Jill's mouth fell open as she realized the implications of her roommate's suggestive gestures.

"Oh...my...god!" she exclaimed, pounding her hands into the bed. "You're not suggesting that I..."

"What?" Haley asked, her face beaming with a brazen, unwavering smile. "Get fucked in the ass? Yes Jilly, actually that's exactly what I'm suggesting."

"That's disgusting," Jill snapped, waving her hand dismissively.

"Oh come on," Haley said, spinning to face her roommate. "You can relieve some of that sexual tension that you so obviously need to get rid of...and you can retain your precious virginity."

"I...don't think so. Why? Have you...?"

Haley cast Jill a knowing glance.

"Oh my God...You have!"

"Yeah," Haley stated simply, turning back to her wardrobe. "I've done it quite a few times."

"And...you...like it?"

"I Love it. As long as the guy knows what he's doing and you use enough lube it can be...amazing."

Jill remained unconvinced.

"In fact," Haley continued, smiling at the obscene thoughts running through her filthy mind. "Sometimes it feels better in my ass than in my pussy."

"Doesn't it hurt?"

"It can," Haley replied with a shrug as she turned away and peeled off her t-shirt. "But then again...I don't mind a little pain now and then."

"Ugghh, Haley!" Jill fumed as she turned away from her undressing friend. "Do you have to do that right in front of me?"

"Lighten up girl," she shot back as she pulled her panties down her legs. "Nothing you haven't seen before."

Haley grabbed a towel and wrapped it around her slender body.

"Although...," she said, as if recently enlightened by a new idea. "That might be another way you could...relieve some sexual tension."

"Excuse me?"

"You could go lez," Haley answered with nonchalance that Jill found eerily dismaying. "Girls can be fun too. Not as fun as guys in my opinion, but..."

"I think that's enough information for one day," Jill piped in, cutting her off before she could reveal any more of her sordid advice.

Haley turned and laughed with amusement, taking enjoyment in her roommate's discomfort.

"You know what Jill?" she said, skipping over to her dresser and pulling open one of the drawers. "I think I have the answer right here."

"Oh really?" Jill answered back, her voice dripping with skepticism as her roommate rummaged through the drawer. "And just what might that be?"

"Well...," Haley muttered as she continued searching. "I was going to wait until your birthday to give this to you but...I think it might be a good idea to let you have it now."

Jill's curiosity was peaked by her friend's enigmatic comments, although she pretended to show no interest.

"Ah! Here it is!" Haley proclaimed, pulling an object from the drawer.

Jill then watched as her roommate walked towards the door, tossing the object on the bed.

"Well, I'm going to have a shower," she said with mischievious smirk. "Enjoy."

As Haley left the room, Jill stared in astonishment at the object on her bed. Lying on the blankets beside her, encased in plastic packaging, was a slender, pink vibrator.

* * * * * * * * * * *

Jill sat at her desk, leafing through her book and scrawling notes on a piece of paper. She had been at her task for a couple hours, but she was finding it extremely difficult to concentrate. Aside from the distracting sounds of drunken college kids roaming the hallways, her thoughts kept going back to conversation she had had with Haley earlier that night. Maybe her roommate was right? Maybe she should consider branching out and trying some new things? After all, wasn't college the time to be having fun?

She slammed her book closed in frustration and glanced up at the clock. It was 11:30 on a Friday night and she was sitting in her room, working on an essay that wasn't due for two more weeks! She wondered what Haley might be doing. 'Probably getting drunk and hooking up with some guy', she thought as she laughed quietly to herself. As much as she tended to frustrate and annoy her, Jill possessed a certain envy for her roommate's carefree attitude and self-assured confidence.

She glanced over at the drawer in her night table that now held the new toy that Haley had so generously bestowed upon her. Although she would never admit it, Jill was fascinated by her new possession. She had always thought about getting one, but had been far too embarrassed to buy one herself. She also could not stop thinking about her roommate's naughty suggestions. She had always intended to save her virginity for marriage, but she had never given much thought to oral or anal sex. It wasn't like she didn't fantasize once in a while, she was just intimidated by the blatant manner in which Haley talked about sex. In fact, ever since she had come to college, her hormones had been running rampant. She had never had so many sex dreams and erotic thoughts in her entire life!

Jill let out a deep breath and pushed her books aside, reaching for her computer mouse. She was about to check her email when she became struck with an uncharacteristically naughty idea. She paused for a moment in hesitation before typing the words 'anal sex' into Google.

After browsing through the results and viewing numerous pictures and stories, she came upon a site that streamed short clips of pornographic videos. She would never admit that she watched dirty movies, but the accessibility that the internet offered made it just too hard to resist. She often became aroused by watching them, but her arousal would soon give way to feelings of guilt and shame that tended to make the situation less enjoyable. She had especially been drawn to videos featuring regular sex although on this night, her interests were drawn elsewhere.

She located a video featuring a young blonde woman who appeared to be around her own age. For some reason she felt drawn to clips that had actresses with physical features similar to her own. She pressed play and leaned in with growing interest. The clip began with the man tossing the woman on a bed as she quickly assumed a position on all fours. He then began licking her from behind, paying much attention to her ass, going so far as to stick his tongue right inside. Jill was beginning to wonder what that might feel like, when the man placed his penis against her tiny hole and pushed himself easily inside. As she watched the sexy couple work though an assortment of different positions, Jill felt herself growing wet and she placed her hand between her legs and pressed her thighs tightly together. As the scene came to an end, with the man spraying his costar's backside with his seed, Jill quickly closed the window as her usual feeling of shame began to creep into her consciousness. She then deleted her browsing history, as she usually did before preparing for bed.

Twenty minutes later Jill was in bed, tossing and turning as she struggled to find a comfortable position. Dorm room beds were small and hard, but it was the renewed clamor in the hallway that really prevented her from finding the loving embraces of slumber. She groaned with displeasure as she flipped her pillow over to find a cooler side before pulling the covers up over her head. She knew that Haley would be coming home drunk at around three A.M. and she wanted to be fast asleep by then.

Unable to get to sleep ten minutes later, Jill reached over and opened her night table drawer.

As she inspected the small plastic vibrator in the dim light of the darkened bedroom, she ran her fingers gingerly down the shaft, feeling every bump in the soft rubber. The core of the toy was made of hard plastic, giving it a stable base, but the exterior was sheathed in a soft pliable rubber, formed into the shape of a real penis. There was a black dial protruding from the base that functioned as a switch for the vibrating function, with three levels of intensity.

Jill turned the little black knob and the toy sprang to life, vibrating in her hand and emitting a quiet buzzing noise. She wrapped her hand around the rubber shaft, feeling the pleasurable sensation as the vibrations coursed up her arm. She found herself getting excited by the mere action of holding the naughty object as she lay there in bed. She turned the dial again and the faint buzzing turned louder as her hand began to shake. Startled, Jill turned the vibrator off and buried it under the sheets.

A few seconds later however, her curiosity got the best of her and she once again scooped up the vibrator into her eager hand. Before she could change her mind again, Jill scrambled to remove her underwear before turning the little back switch once again. She could feel her pussy begin to drool at the mere thought of using the toy and shoved her hand under the blanket to place the soft rubber tip over her clit. She had masturbated plenty of times before, but never with an object. The thought of using something so realistically penis-like sent shivers of anticipation up her spine.

As the buzzing toy touched her little fleshy button, her toes clenched and she let out a startled sigh as the reverberations sent blissful waves of pleasure through her entire pelvic region. Jill pressed the tip harder against her clit and began shifting it back and forth, rubbing her sensitive appendage as the vibrations continued to tantalize her growing lust. As good as the experience felt however, there was something else she wanted to try. Moving the rubber shaft lower, she slipped the spongy tip down over her flushing lips before slowly pushing it inside. For the first time in her life, a penis (albeit a fake one) was inside her tight little virgin hole. She twisted and turned the toy, coating it with lubricating fluids as she worked it deeper inside. As she slipped it inside, Jill began to think about what it would feel like to have a man attached to the dick. She thought about the weight of him on top of her. She thought about the feeling of his lips on hers. She thought about his hands all over her body.

Jill began sliding the vibrator in and out as she reached down with her other hand and pressed a finger against her little pink clit. She thought about what it would feel like to have a man's tongue inside her. She imagined that it was a pair of lips on her clit instead of her own finger. She imagined a man's face in between her legs, licking and sucking...

She then thought about what it would be like to have a guy's dick in her mouth and she stopped. Taking a deep breath, she pulled the wet dildo from her eager, wet hole and held it up above her face. The moonlight from the window was spilling in, causing the toy to glisten with a shimmering sheen as she inspected it with growing interest. Jill then turned the vibrator off and placed it at her mouth. As soon as she felt the moisture from the rubber tip wetting her lips, she grew even more aroused and slipped it into her mouth. Swirling her tongue around the life-like head, she closed her eyes and imagined it was real. She could taste herself on the rubber toy, which only turned her on more. Although she would never admit it, she quite enjoyed the taste of her own pussy and reveled in the idea that she might be licking her juices off a real cock.

She slipped it farther into her mouth, her soft lips gliding easily along the wet shaft, feeling every bump in the soft rubber. The toy had fake veins fashioned along its length, which she originally found quite humorous. At that moment, however, she relished the life-like quality as she slipped it in and out of her hungry little mouth.

After wetting the mock penis with her lips and tongue she pushed it back into her virgin pussy, gently working it inside. As she sawed the rubber toy in and out with increasing speed, her thoughts began to drift back to the video she had watched. She thought about that little blonde woman moaning as she took that dick deep in her ass. As the filthy recollection overtook her thoughts, Jill placed a finger in her mouth and wetted it with lines of saliva before reaching around to place her fingertip at her anus. She had never played with her ass before. In fact she had never even thought about it. But as she imagined what that porn star must have felt when that man was licking her there, she pushed the vibrator deep inside and gently massaged her asshole with soft circular motions of her little wet finger.