Jill Goes to College
written by:
DamonX

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 trepiditious 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, lighthearted 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 skeptical 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 skeptic 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.

As the tip of her digit stroked her tiny, puckered hole, she felt every wrinkle and smooth patch of skin with tactile clarity. With her shy little orifice growing moist and slippery under her finger, Jill pressed a little harder, feeling the tightly closed opening slowly give way. Letting out a quiet moan, she slipped her tip in a little more as her diminutive ring hugged her finger around the knuckle. She was amazed and enticed by the smoothness of her internal walls and pushed her finger in deeper as her pussy grew damp around the plunging dildo. She decided she liked the sensation, although she couldn't decide if it was the physical feeling of her finger in her ass, or the simple naughtiness of it all that aroused her so.

As her virgin asshole soon accommodated the circumference of her thrusting finger, Jill decided to go one step farther.

Emptying her holes of both finger and toy, she pulled her legs up and placed the head of the vibrator at her tight little anal entrance.

"Well, here goes nothing," she muttered to herself as she began to push.

Jill tried to relax, but was having a difficult time due to the thickness of the toy. She reached her other hand down and applied a constant pressure with both hands as she laid he head back and closed her eyes. Slowly and gradually, her tight muscular ring gave way to permit the invasion of the plunging rubber cock. As it slid in half way, Jill began to twist the vibrator, working it in and out with short, careful strokes. It was a strange sensation, but it didn't really hurt as much as she thought it would. Again, it seemed to be the psychological stimulation that was the greatest stimulant.

Again thinking back to the video clip, Jill thought about herself on her hands and knees like the woman in the scene. Tossing the covers off, she rolled over and assumed a similar position with her head lying flat against the mattress with her ass up in the air. In the new position, she began to work the toy deeper into her own ass as she complimented the anal stimulation with a little clitoral action as well.

Her breath began to grow ragged as she pressed her clit with firm, consistent strokes of her nimble little finger. Reaching back to the butt end of the vibe, she flipped the switch back on, sending pleasurable reverberations pulsing through her greedy little asshole. The vibrations combined with the rubbing of her fingers on her clitoris sent a wave of pleasure streaming down her spine and she jammed the toy deeper into her twitching body. She became so lost in the new sensation that she almost didn't hear the sound of a key turning in the door.

With frantic urgency, Jill dropped to the bed and yanked the covers up over herself. She had just enough time to reach down and cease the quiet buzzing as the door slowly opened. Her heart was racing as she pretended to sleep, her eyes wide with embarrassment as she stared at the wall and listened intently.

She could hear Haley rummaging through her things as if searching for something. After a few minutes of this, she left and closed the door quietly behind her. Jill let out a deep breath of relief as she slid the vibrator out of her ass and rolled over onto her back. As she held the rubber toy in her hand, she began to wonder...What would a real dick feel like?

* * * * * * * * * * * * *

When Jill awoke the following morning, she was looking forward to another session with her new favorite toy, but unfortunately Haley had returned during the night and was fast asleep in the bed next to hers. She didn't want to risk being caught, so she decided to postpone her play date for another time. She was still feeling a little frisky however, so she slipped her flip flops and headed to the shower. After taking a few minutes to shave her legs, Jill began to inspect the thick thatch of hair adorning her pubic region. She had noticed that the women in porn movies tended to have relatively little pubic hair and began to wonder if she should as well. She began trimming it down carefully, but before she knew it, she was completely bald. Jill suddenly felt very sexy, and she lightly stroked her hand over her hairless mound as the warm water streamed down over her body. She brushed her fingers against her smooth, wet lips and reached around to run a tip over her tiny little asshole. As she lightly touched her tightly closed hole, she remembered the night before, amazed that she had been able to fit the vibrator inside her.

Upon returning to her room, Jill found her roommate deep in slumber. This was not uncommon since Haley tended to sleep until noon or longer on weekends. After quietly getting dressed, Jill gathered her belongings and headed out the door to go to the library. As she sat alone in the large empty building, Jill once again found it difficult to concentrate

"Ugh," she growled, tossing her pen down in frustration. "What is wrong with me?"

After about an hour more of fruitless, non-productive studying, Jill came to a decision. With unwavering resolve, she gathered her books and hurried back to her dorm room.

"Haley?" she said, pushing her door open and scurrying inside, just as her roommate was crawling out of bed. "I need you to do me a favor."

Haley looked up with surprise for a brief moment before her stunned visage softened into a knowing smile.

"Well, that didn't take long at all," she said with a satisfied smirk.

* * * * * * * *

Later that night, Jill sat sipping a strawberry-kiwi wine cooler as she watched Haley getting ready in front of the mirror.

"Do you want to borrow some make-up?" Haley asked, holding her eyes wide as she applied her eyeliner.

"No thanks," Jill answered politely. "I don't really like to wear make-up."

"Yeah, I've noticed that."

"Why? Do you think I should?"

As she spoke, Jill nervously checked herself out in the mirror. Although she had always received al lot of attention from boys throughout high school, she remained self conscious about her appearance, usually opting for a plain, tom-boyish style of dress. Her blonde hair, which was usually tied back in a pony tail, hung straight down her back in a simple, unassuming fashion. Her skin still retained most of the tan it had accumulated from her summer job, teaching swimming lessons to children, giving her a vibrant, natural looking glow. She had declined borrowing one of Haley's skirts, choosing instead a pair of jeans and a tight fitting white top.

"So what did you tell him about me?" Jill asked, changing the subject as she nervously picked at the plastic label on her bottle.

"I told him everything he needs to know," Haley answered casually. "Don't worry. He really knows what he's doing."

"I can't believe I'm doing this," Jill exclaimed, burying her face in her hands. "Maybe we should call this off."

"Not a chance," Haley countered. "You need this. And besides...the guys are already expecting us."

"It just seems kind of...weird. Having you hook me up with a guy you used to date."

"Oh we didn't date," Haley explained, grabbing the bottle from Jill and taking a drink. "We just fucked a few times."

"And you couldn't have set me up with someone that hasn't...oh I don't know...been inside you?"

Haley laughed at her friend's comment, almost spewing wine cooler out all over the mirror.

"Trust me," she said, handing the bottle back to Jill. "For you first time trying anal...you want to make sure the guy knows what he's doing. And Braden...Well, he knows what he's doing."

Jill managed half a smile as she looked down into the now empty bottle. She could already feel the effects of the single drink as the alcohol coursed through her blood, slowly washing away her trepidation. Aside from being unaccustomed to drinking, her 5'4 frame and slender figure were both major factors contributing to her low tolerance. She was still extremely nervous however, as her mind began to race with expectations. In an effort to preserve her much desired virginity, she was about to allow some stranger access to the most private area on her body.

As she reached for her second drink, Jill watched her roommate apply her make-up, standing in front of the room's only full sized mirror. She had always been somewhat jealous of Haley's free spirit and confidence, even if she had been disapproving of some of her sexual exploits. Always popular with the guys, Haley not only had the looks, but the attitude to go with them. She was a little taller than Jill, with long, dark brown hair and sexy dark brown eyes. Her body was lean and slender, although she never seemed to exercise or watched what she ate. She preferred a provocative, flirty style of dress to Jill's plain, small town attire with preference for short skirts and tight fitting mini dresses. This night she had chosen a short, black skirt and a tight fitting black and white top that dipped low enough to display a tantalizing amount of cleavage, even though her breasts were moderately sized at best.

"Ready to go?" Haley asked, giving herself one final look in the mirror before turning to her friend.

"You know what?" Jill said introspectively as she set her bottle down on the desk. "I think I will borrow a skirt.

* * * * * * * * * * * * * * * * * * *

A few minutes later the girls left the dorm carefully smuggling their drinks through the hallway in their purses. Jill felt strange wearing a skirt, especially one so short, but Haley had assured her that it looked very appealing. She trusted her roommate's judgment concerning fashion although she remained self conscious regarding the length of the little white skirt and found herself continually holding it down as she walked. She had also replaced her shirt with a little pink top that seemed to go better with her skirt. She was actually skeptical about wearing white, but Haley had convinced her to wear the color as she claimed adamantly that it went well with her nicely tanned skin.

The two roommates strolled across campus, keeping out of sight as open alcohol was prohibited in University public areas. Twenty minutes later they found themselves in an off campus residential area that served as housing for many of the college students as well as the majority of fraternity houses. Jill felt her heart beating faster and faster as the pair approached their destination, a small, non-descript house situated along the tree lined street. She nervously finished the remainder of her drink as they approached the front door.

A young man in his early twenties opened the door and immediately exchanged some playful banter with Haley, who could hold her own against anyone when it came to witty repartee. His name was Scott and he appeared to be a cookie cutter image of the guy that she tended to go for. Good looking, clean cut, cocky, and most likely a total prick.

They entered the house and made their way into the living room where Scott's roommate was situated. Jill's heart skipped a beat when she saw him, blushing nervously since everyone in the room knew what the two girls had come for. Braden was a twenty-two year old music student with a dark complexion and a friendly smile. Although not the usual type of guy that Jill was attracted to, she immediately found him to be quite attractive. His dark brown hair was styled in a way as though to appear messy, even though it was obviously purposefully done. His green eyes were so prominent that she thought they must be contact lenses, although it may have simply been due to the contrast with his dark complexion. He was dressed in a pair of faded jeans and a tight fitting black shirt, outlining a muscular body that Jill thought would be more suited to an athlete than a musician. He also had earrings in both ears and a tattoo along the underside of his forearm. She had never been a fan of tattoos on guys, but for some reason it didn't seem to bother her on Braden.

The four sat around talking and drinking for the next couple hours although Jill remained quiet throughout most of the conversation. She constantly found herself pulling the tiny skirt down her legs in a self conscious effort to hide her exposed thighs as she noticed both men stealing casual glances. As they talked, her theory about Scott was confirmed. He was a prick. Haley always referred to it as ‘confidence' and not ‘cockiness' but Jill disagreed. He was a narcissistic, self obsessed asshole who always seemed to bring the topic of conversation back to himself. Actually, he seemed perfect for Haley who tended to portray many of the same traits, although in much more tolerable doses.

Braden, on the other hand, seemed relatively humble. She could hardly believe the two could be friends since they seemed to possess personalities at polar opposite ends of the spectrum. She was secretly thankful that her roommate had set her up with Braden and not Scott.

As the night wore and Jill drank more and more, she soon found many of her previous inhibitions slowly drifting away. As she became more talkative, Braden began paying her more attention until soon they were exchanging smiles and knowing glances from across the coffee table.

"Hey Braden," Haley said finally with a suggestive tone. "Why don't you go show Jill your guitars? I'm sure she'd love to see them."

Jill blushed immediately since everyone knew the real intent behind Haley's suggestion. Braden smiled and stood up, motioning for her to follow as he walked out of the room. After giving her friend one final glance, she stood up and followed, her cheeks still flushed red and her palms sweating with anxious anticipation. She could hear Scott and Haley snickering and whispering to each other as she left.

Braden led her down to the basement, where his bedroom was situated. In actuality it looked to be more of a recording studio than a bedroom with numerous guitars, amplifiers and other pieces of equipment that Jill had never even seen before. The walls were covered in posters, mostly of bands that she had never even seen before. In the corner of the room were two mattresses, one stacked atop the other with a few blankets strewn across in disarray. That set-up seemed to be typical of most college students, although Braden's room seemed to lack the usual assortment of dirty laundry that littered the floors of the typical male student's abode.

"So...these are your guitars?" Jill asked, fidgeting awkwardly as she stood in the middle of the floor.

Braden laughed.

"You don't care about my guitars," he said with a smile, walking up behind her and resting a hand on each one of her hips. "We both know why you're here."

"Oh my God!" Jill muttered with embarrassment, reaching up to cover her blushing face. "You think I'm weird don't you? Haley said that...,"

"It's okay," he said softly, the calmness of his voice settling her nerves as he brushed her hair back from her neck. "And I don't think you're weird."

Jill's body tingled with excitement as she felt him lean down and kissed her neck. She took a deep breath and sighed as his soft lips pressed into her skin eliciting a subtle moan as she closed her eyes with enjoyment. His hands moved slowly over her body, one sliding up her waist as the other drifted downwards, caressing her thigh through the short, white miniskirt.

"Can...we turn off the lights?" Jill asked quietly, feeling exposed as they stood in the middle of the room.

Braden agreed and walked over to dim the lights as Jill sat down on the bed. He then made his way back over to her, sitting down as she turned to face him. He kissed her and she immediately responded by kissing him back, leading to a make-out session that would last for the next ten minutes without pause.

Jill could feel herself becoming aroused as Braden began to slide his hand up her thigh. Lying back on the bed, she purred sensually as she felt his fingers touching the soft fabric of her little white panties, growing moist under his touch. He pressed a little harder, making her squirm as his fingers found her clit through her underwear and started to rub gently. Unlike the boys she had previously been with, Braden seemed to know exactly what he was doing; avoiding the awkward fumbling and prodding that had marred the majority of her early experiences.

Her pace quickened even further as he reached around and began to slide the panties down off her hips. She lifted her body in assistance and felt the smooth fabric sliding easily down her legs. She could now feel the air against her naked pussy and she grew even more aroused, as Braden started to remove her skirt. A few seconds later and Jill found herself completely naked from the waist down as he leaned back in to kiss her, his hand once again finding its way between her legs.

Braden uttered a quiet murmur of approval when he felt the bare skin of her freshly shaved pussy beneath his touch and gently parted her soft folds before sliding a finger inside her. Jill immediately sensed her little hole dampen from the penetration and for a moment she thought about letting him take her virginity. She quickly reconsidered however, opting to stick to her principles and maintain the sanctity of that particular orifice. She was still intent on giving him her mouth and her ass, and after all...two out of three wasn't bad.

Braden soon took his shirt and pants off before coaxing Jill to remove the last items of her clothing as well. With only a pair of underwear remaining between the two, she could feel the hardness of his dick against her leg, separated by only that meager bit of material. His intense fingering had turned Jill's tight little pussy into a sopping wet hole as he added another finger and caused her to squirm with desire under his expert hand.

"Here," he said softly as he offered his dripping wet fingers to her.

Jill opened her mouth and he pushed them inside, smiling as she closed her lips around them and tasted her juices with delight. He then reached the wet fingers back down and traced the outline of her dewy lips before sliding downwards even farther.

Jill's body froze as she felt her tiny sensitive asshole being touched for the very first time. She spread her legs, lifting one up to give Braden access to her little hole as he rubbed it carefully with soft, circular motions. She closed her eyes and purred, relishing the sensation as his wet finger caressed her pink star before gently pressing against the resistant ring. His mouth found one of her nipples and sucked gently as her asshole slowly opened around his fingertip. Jill wiggled blissfully as she experienced the odd sensation of her tight, virgin hole being pried open as Braden kissed his way down her body.

Jill had been fingered before, but she had never had a guy go down on her. Her small body tingled with excitement as his lips traveled down her stomach, leaving a trail of wet kisses, leading ever downward. Jill moaned and reached out grasp at the bulge in Braden's underwear, feeling the surprising hardness of his dick through the thin material.

"I want it in my mouth," she murmured softly, tugging at his waistband as the pair moved into a side-lying makeshift sixty nine position.

As she pulled his underwear down over her hips, he wriggled his fingertip deeper into her clutching butthole. His rigid cock sprang free, dangling enticingly in front of her face as his mouth planted teasing kisses along her hips and inner thighs. She eyed his dick with wonder as she tentatively took it in her small hand and tested his firmness with a gentle squeeze.

"Uhhh," she gasped suddenly as Braden planted his mouth over her wet little pussy.

His tongue delved down into her moist folds before he closed his lips around her tiny clit and sucked, sending a rush of pleasure down to her toes. The feeling of his warm, wet tongue urged her onwards and she lifted his dick towards her mouth. She could see a tiny glistening droplet of precum clinging to the end of his tip, and she flicked her tongue out to lap it up, touching a penis with her mouth for the very first time. She then parted her lips and took his spongy helmet in as he moaned with approval.

With her tiny asshole hugging his finger, Braden slowly pumped it back and forth, her tight little ring moving with every gentle thrust. As his mouth continued to work on her virgin pussy, Jill's lips gradually enveloped the head of his pulsing cock. She didn't really know what to do, but she found the feeling of a dick in her mouth strangely appealing. She could feel the warmth and hardness with her lips as her little pink tongue wriggled against the underside. Gradually Braden shifted his body until he was on top, straddling her face with the tip of his cock dangling into her suckling mouth as he lapped at her pussy with long, expert licks.

The new position seemed so dirty to Jill, but she also found it to be intensely arousing. Her small hands caressed the back of his thighs as she gazed up at his hairless balls and ass. Carefully, he began moving his hips, sending his dick in and out of her mouth as she purred with enjoyment. His strong hands were under her, one pulling her little cheek to the side as the other toyed with her eager asshole, sliding gradually deeper with each subtle movement.

Braden then rolled them over, bringing Jill to the top position as he dove back into her tasty pussy with enthusiastic craving. She began lightly stroking his shaft as she peppered his length with soft licks and kisses. As she reached the bottom, she moved on to his balls, exploring with her little pink tongue as he buried his deep into her wet, virgin hole. As he withdrew from her pussy, he moved upwards, pulling her ass cheeks downwards with his strong hands. His tongue flicked out and wiggled its way between her pert little cheeks as Jill froze. He was going to lick her ass! She had seen the act performed in porn movies, but she didn't think anybody actually did it in real life. She was about to stop him when she felt Braden's warm, wet tongue stab into her tiny, clenched star.

"Oh my God!" she gasped as her ass clenched reflexively at the surprising intrusion.

The feeling was indescribable. She closed her eyes and moaned, holding his pulsing cock pressed lovingly against her face. Her elated gasps urged him to continue and he covered her little pink hole with slathering licks before trying to pierce her opening with a few aggressive, wet stabs.

"Put your finger in your ass," he said, pulling back to her dripping pussy. "I want to see you finger inside your ass."

Jill swallowed and reached back with hesitation, feeling slightly inhibited at performing such a lewd act in such close proximity to Braden's watching eyes. Nevertheless she obeyed, sliding her finger down between her cheeks and feeling the left over wetness from his pleasing tongue. Sliding over her asshole, she rubbed it a few times before curling her tiny finger and pushing it inside. Braden went back to tonguing her pussy as he watched intently as she started thrusting deeper into her clutching hole. Growing bolder with every passing moment, she began finger fucking her own as she lay atop his body, once again taking his dick into her unexperienced mouth.

"I...want...," she began tentatively, her arousal growing with every plunge of her little finger. "I want...you to fuck me."

Those words, although so difficult for her to say could not have been more truthful. Jill needed his dick in her ass.

A few moments later and she was on her hands and knees as Braden knelt behind her, covering his length with lubricant in preparation. She felt so naughty, situated in the scandalous position as her heart raced with anticipation. With his dick adequately lubed, he coated a finger and resumed testing her virgin hole by sliding it deep inside her.

Jill gasped as his penetrating digit reached greater depths than before, pushing deep up to his knuckle, sliding easily with the aid of the slippery substance. She closed her eyes and moaned, resting her head against the bed and arching her back in an unintentionally seductive pose as he fucked her ass with long, slow strokes of his finger. She gasped again, this time after he added a second finger, feeling her tiny hole stretching pleasurably as he prepared her for the main course.

"Are you ready?" he asked, twisting and turning his fingers inside her before slowly withdrawing.

Jill turned her head to look back at him, her breathing coming in soft, excited pants.

"Yes."

She then closed her eyes and waited, feeling the mattress shift under her as Braden moved into position. A second later, she felt his slick cock being placed between her cheeks and sliding down over her waiting hole. He rubbed it up and down a couple times before centering on her tiny ring and gently pushing. Jill took a deep breath and tried to relax as she felt her tight little opening slowly stretching around his tip.

"Are you okay?" Braden asked, pausing with his helmet shaped head firmly entrapped within her clutching ring.

"Uh huh," she muttered, reaching back to gently play with her clit as he resumed pushing.

He shifted back and forth, barely moving at all as his shaft gradually slipped deeper into Jill's eager asshole. She moaned into the mattress and reached one hand back to feel her muscular ring stretched tightly around his cock. She touched his wet shaft softly as it slipped in and out with careful, inching strokes. Actually feeling his dick as it pulsed against her hugging hole turned her on even more as she marveled at the ability of her tiny orifice to swallow up his thick girth.

Turning her attention back to her clit, Jill worked her little fleshy button with increasing desperation as Braden's pace quickened and his strokes deepened. She closed her eyes and imagined what she must look like at that moment. On her knees with some strange guy's cock buried deep in her asshole, just like the slutty women in the porn movies. The thought made her pussy drool as he worked his thick shaft in and out with eager, mindful thrusts.

"Oh yeah," she squeaked, her body shuddering with lustful pleasure. "Fuck me. Fuck my ass."

Her words urged him on and Braden pushed deeper, filling her asshole completely as his balls pushed into her dewy little pussy lips.

"Do you like having my cock in your ass?" he asked, his voice raspy and forced as he gave her two quick thrusts that sent her tiny body quivering.

"Yes!" she exclaimed. "I love it. Please don't stop. Don't stop fucking my ass."

Jill pushed her ass back against him as the strength of his strokes increased.

"I'm going to cum inside you," Braden said, his hands gripping her hips as he continued to plunder her virgin hole.

"I don't care," she gasped in response. Do whatever you want. Just don't stop fucking my ass?"

She could hear him panting as he thrusting grew more and more erratic. Her fingers frantically attacked her clit as she felt herself approaching her ever elusive orgasm. Braden's cock plunged a few more times before he groaned and twitched, his muscles spasming with climactic intensity. Jill then felt his dick swell and pulse as her clutching tunnel was blasted by a frenzied spattering of hot cum.

The warming sensation combined with her busy fingers sent her reeling as her entire body tensed with orgasmic release. She clenched her teeth to muffle her ecstatic howling, her asshole clenching around Braden's cum-coated cock. As the savage climax subsided, Jill sighed with relief and as she felt him slowly withdrawing from the slippery embrace of her freshly fucked hole. Braden sat back and reached for his underwear as Jill collapsed into the bed, as thin trickle of warm cum dripping from her ass.

"I'm going to get some water," he said, standing up and heading for the door. "Want some?"

Jill agreed, breathing softly into her arm as remained motionless as he left the room. She lay there for a few seconds before reaching back and gingerly touching her recently abused asshole, still slick from cum and lubricant. Carefully, she eased her tiny finger inside, feeling the slimy sensation of Braden's juices coating her tight little tunnel. She purred with contentment as the events of the past hour flitted through her mind, causing her pussy to water once again.

"Yes," she thought to herself. "I think I could get used to this."

The End