Jill Goes to College

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.