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.