College Days

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Three friends plan a vacation.
3.8k words
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The cabin had been built in the 1950's by a wealthy Boston couple that wanted an excuse to escape the city life without having to leave their beloved Massachusetts. Every summer they would drive their children across the state to visit with nature in the "wild lands" of Western Massachusetts for a few weeks. Massachusetts was their home and they wanted to stay there even in vacation.

The cabin was sold by the couple's children in the 80s when the upkeep became too much and it was bought by a moderately successful investment broker in New York City who couldn't afford to join his colleagues in the Hamptons. He tried to pretend that his cabin in MA made him edgy and adventurous, but it was a poor cover for his failures. During the decade that he owned it his visits only increased as his potential for promotion and drive slowly decreased. He sold it shortly after he lost his job. He was able to get a less stressful job in Texas and ended up settling down with a fairly pretty wife and decently bright kids who, despite a few rough patches, turned out all right.

A struggling, reclusive, but talented writer bought it from him for quite the bargain, but he only lived there for a few years until he realized that being the "reclusive writer" was no longer the image that he wanted to maintain. He moved to Jersey due to its proximity to New York City and cheaper rents, and while he was able to publish a few short stories and a novel that sold decently; he was never able to put aside his desires to be a writer in order to fulfill his talent and write.

He sold it to a couple who wanted to raise their children away from the city and suburbs, but hard times forced them out of the wilderness and into the home of her parents in 1998. This caused an understandable friction in their marriage. She accused him of not working hard enough and he accused her of not being supportive of his struggles. Her parents thought he was a nice boy who couldn't handle the pressures of work and marriage.

He eventually was able to right the ship, and they moved to a small house in the suburbs 15 months later. Their marriage never recovered from those hard times and they divorced in early 2000. They would both privately admit that they had not tried hard enough to save the marriage during those difficult years.

The house struggled in the early 2000's, but was bought in 2004 by lesbian couple who had grown tired of the Texas heat. At first, they had lived there full time, but eventually moved to North Hampton in order to be closer to their work. One taught at Smith while the other owned an erotic boutique that catered to the more adventurous students and housewives in the area. A commute of any sort is Hell during a Massachusetts winter; especially if you are Texan.

That is how the cabin fell into the hands of Cat. Her Aunt, being the young entrepreneur in North Hampton, offered it to her during any long weekends or vacations. Cat had failed to utilize the cabin during her first two years at college, but junior year, on a whim, she invited two of her friends along for spring break. Jackson and Amanda were two of her apartment mates who were not planning on leaving campus for break and they were more than willing to spend a week in the middle of nowhere with her. The details were worked out easily enough and all that remained was to pack.

"It can get pretty chilly up there at night, but my Aunt says that it is generally pretty warm during the day," Cat reminded them as they headed to their rooms to pack.

Jackson and Amanda nodded before heading off to their rooms. Jackson tossed a few clothes into a bag and got ready for bed. He had underwear, layers, jeans, and would bring a jacket or two, so he felt he was fine. He normally didn't stress too much about packing.

It was only eleven and he wasn't quite sure how to entertain himself for the rest of the night. He didn't feel up to reading, and porn, while it would do in a pinch, really didn't hold his interest at this moment. He could hear Amanda talking on the phone in her room. Their rooms shared a paper thin wall and he could often hear her putting around in there.

When they first moved in, Jackson assumed he would be able to listen in on her having sex with her boyfriend on a regular basis, an exciting prospect, but while he did occasionally hear moans and bed squeaks coming from the other side of the wall; it was not nearly as much as he had hoped. Amanda had always been more reserved when it came to sex. Jackson assumed that they were usually very quiet or strategically waited to have sex when no one else, or at least he, was out.

Jackson sat down at his desk that was shoved against the shared wall, turned on his computer, and stared at the ceiling while he waited for the computer to load. The ceiling was made up of those fragile tiles that are so common in office buildings and cheap apartments. On a boredom fueled whim, Jackson climbed up on his desk and pushed up a ceiling tile to explore what lay hidden above his head.

He pushed up the tile and shoved his head through the opening and he was immediately met by the stale musky air. There were a few old pipes, some spider webs, and little else. He thought about thumping the floor of the upstairs apartment to see if he could get them to think it was a ghost, but decided to avoid a puerile and unexciting activity. He was getting ready to give up and look at porn for the evening when he saw a sliver of light coming from Amanda's room. He looked closer and saw he was looking directly into Amanda's room.

She was walking around the room while talking on the phone and packing. She was still wearing her corduroy pants, but she had taken off her shirt and was wearing only her black bra. Jackson's eyes widened in surprise and he knew that he should look away, but the whole experience was too exciting for him to quit.

She was trying to fold a shirt while the phone was tucked between her ear and shoulder. "But R," she said—talking to her boyfriend Roland who had already gone home to New Hampshire—"You already said that there wouldn't be time for me to go visit you anyway, so I don't see why you're so upset about this." Jackson watched her tanned back as she continued to struggle with her multi-tasking. "It sounds like you're just pissed because now I have something to do while you're gone," she hissed into the phone. Jackson briefly ducked away from his voyeuristic activities to turn off the lights in his room; hoping that it would keep him from being seen.

"That would certainly kill a friendship," he thought.

When he returned to his perch Amanda was sitting on her bed facing Jackson's room. She looked a little flushed and Jackson assumed that whatever Roland was saying was making her less and less pleased. While he was gone she had taken her hair out of the pony tail and her straight brown hair hung around her neck and shoulders. Her round cheeks were slightly flushed and she closed her eyes as she brought her shoulders back to crack her back. Her breasts, which Jackson assumed to be a C cup, strained against her bra; Jackson slowly slipped a hand to his crotch. He loved her tanned, toned skin and her big brown eyes. He had often wondered, if things had gone differently, if he and Amanda would have made a good couple.

Amanda leaned back on the bed and spoke into the phone, "R, I have a better idea." She her right hand down to her pants and unbuttoned them; "why don't I tell you what I'm wearing," she whispered as she unzipped her pants, showing Jackson a glimpse of her black underwear. "I don't care where you," she whispered again as she ran her fingers along her stomach, "you don't have to say a word." She was now lying fully on her back with her eyes half closed and her fingers slowly running along the length of her torso when she stopped and bolted upright, "phone sex is not weird," she hissed into the phone. "All I know is that you are gone for a week and I'm horny. I don't care if you're at your mom's house; I know you've masturbated there before." She listened to the phone with a flushed face and the heavy breathing of anger.

"Fine," she said, "I'll call you before I leave tomorrow. Cat said cell reception is pretty bad." She paused and quickly rolled her eyes before saying "no, I'm not mad. Irritated, but not mad." She stood up and walked to her laundry hamper at the other end of the room; "Yeah, I love you too. Night, honey," she said as she shimmied out of her jeans.

Jackson quietly undid his jeans and reached down to grab his cock as he stared at Amanda's ass; highlighted by the tight black panties. He slowly pulled his cock out as she shrugged off her bra, and he had to fight back a moan at the site of her tan back that was now unmarred by the thin black strap of the bra. He held his breath silently begging her to turn around, but she did something better: she stepped out of her underwear. The sight of her ass caused a hitch in Jackson's breath and a bolt of pleasure to his cock. Her ass was fantastic, firm, yet large; made all the more alluring by the paleness of her tan lines contrasting with her dark legs. She bent down to pick up her panties with only a minimal bending of the knees, and thrusting her ass out towards Jackson.

Jackson closed his eyes overcome by the vision of his cock disappearing between her cheeks, her pussy gripping his cock, her whimpers of pleasure. When he opened his eyes she was walking across the room toward the shelves by her door and he took her profile in. Her breasts softly bounced with each step, her small brown nipples leading the charge. Jackson tried desperately to see all of her. Her ass as she walked, her toned legs, the glimpse of her shaven mons pubis. She caught a glimpse of herself on the mirror hanging from the door and slightly changed course until she was standing in front of it.

She and Jackson both studied her figure in the mirror. The angle was poor and the lighting was bad, but Jackson strained to see her slit in the mirror. Jackson licked his palm and continued to slowly masturbate and Amanda lifted her left breast and rubbed below it where the bra had left its mark. She moved her hand down to her pussy and gave her vulva a gentle rub, seemingly to determine if she needed to shave again.

She turned to walk to her bed when a low moan drifted through the apartment; Jackson jumped at the unexpected sound, but Amanda smiled and kept walking. Cat was a vocal masturbator; a fact that Amanda had come to terms with and even, at times, been aroused by. Jackson, still enamored with Amanda's naked form, suddenly wished he could also spy into Cat's room at this particular moment. He quickly bent down and bent over his desk to open the second drawer where he kept his lube and popped back up to his secret spot in the ceiling. Amanda was doing some last minute organizing before bed and he returned right as she was crawling onto her bed giving him a nice view of her ass and pussy before she gave a little roll and ended up naked, in bed, and on her side.

Jackson stifled another moan as he slowly poured the lube onto his cock to sear the image of Amanda's pussy, framed beautifully by her strong thighs, into his mind

Amanda was horny. She had wanted to have phone sex with Roland, but was shot down by her boyfriend's prudish ways; and now her roommate was fingering herself while making only the most minimal of efforts to hide her enjoyment. It seemed that arousal was just being forced her way. She rolled onto her back, closed her eyes and began to run her fingers down her stomach and along her thighs. She let out a soft sigh as another moan from Cat floated across the halls.

Jackson watched as if enchanted by the unwitting seductress that lay before him. Amanda's pussy had long thick lips that looked as if they had been created separately from the rest of body and then molded on by a master craftsman. Her inner lips made their presence known with a gentle persistence that hinted at an endearing delicacy, and kept her vulva from uniting.

Jackson cupped the head of his penis and slowly twisted and rolled his hand over it as Amanda gently drifted her fingers from her inner thigh to her pussy. She gently spread her lips with her ring and pointer fingers while her middle finger slowly wandered up towards her clit, stopping just short of the prize. Her finger slowly detoured around her clit, moving in slow circles around it. The signs of her arousal, which had been present before, now rushed forward to take center stage. Her cheeks flushed red; her nipples hardened as they ached for a caress or a twist, and a thin tear of fluid escaped her pussy and began to flee towards her hidden hole, but was caught by her roving finger. She slowly inserted her finger inside her pussy; letting out a soft, short gasp as she entered herself.

Her digit only remained for a few seconds, and she pulled out and brought her now wet finger back up and hovered over her clit, while her left hand caressed its way up her stomach and gentle brushed her dark, hard nipple.

Cat's moans still played in the back ground, but Jackson could barely hear them through the pounding of his own arousal. His hands were caressing and kneading his balls—his cock couldn't take much more without cumming—but time seemed to have stopped; the world holding its breath and waiting for Amanda's finger to come down for that first contact with her clit. Her breasts heaved with each pant, her legs demurely spread and quivering in anticipation at what they knew was about to come, her eyes closed as she erotically teased herself, and sweat formed on her forehead. Jackson realized that he was holding his breath, but he couldn't release it. Every ion of his being was waiting for her to continue. Every single aspect of him needed her to continue. Every part of him wanted her.

Then, as if on some secret cue, her finger dropped and time started again. A soft "oh, God" rolled from her lips, her hips bucked, her hips bucked up to meet her fingers, her knees dipped together, her shoulders arched, and her head rolled back, while her fingers froze—one on her nipple and one on her clit. Slowly her fingers began moving again; softly spinning her clit and her nipple in near unison.

Jackson's cock ached from the strength of his arousal and he brought his left hand down to bring his the extra attention it craved. His well lubed right hand ran down his shaft, under his balls, and a lithe finger gently caressed his ass hole. His body gave a shudder and his knees almost gave out, bringing his face down against the cool, faux-wood paneling of his wall. He forced himself to release his cock and raised himself so he could continue to watch Amanda. He quickly added more lube cock, lifted it up, and pushed his hips forward so he was rubbing himself against the chilled wall.

Amanda had shifted slightly so her head was in her pillow, but he could still hear her soft moans of "Oh, God. Oh, God." Her finger still moving in slow but hard circles over her clit, but now she was flicking her nipple back forth with her finger. Her eyes were clamped shut, and her legs were quivering. Jackson's hips were thrusting against the wall—his last ounce of concentration was used to keep himself under control.

Their reverie of bliss was broken by Cat's orgasmic wail of "Oh, I'm cumming." Amanda's eyes shot open and then rolled back in pleasure. Jackson's cock started pulsing as it prepared for orgasm, and waves of pleasure emanated from his cock throughout his body. Amanda's legs lifted up off the mattress and she pulled them close to her body; her mouth was opened and making almost inaudible groans and pants. Cat's orgasmic cries of "Oh, fuck me, fuck, oh fuck, fffuuuuuuck me," goaded them onto their own release. Amanda coiled herself like a loaded spring, with her legs to her chest, showing off her glistening pussy and bare ass hole before orgasm gripped her, and her legs slammed down onto the bed; her hips bucked wildly, biting her lip not to scream out.

Jackson's orgasm felt like it turned his cock into a fire hose. His knee's buckled and held onto the top of the wall with one hand and his cock with the other as his cum shot against the wall and blasted back onto his stomach, chest, face, and a myriad of other different directions. After he caught his breath, he peaked back over the wall. Amanda was still lying in her bed with her legs spread wide; giving him a clear view of her engorged pussy. Her hands were lying on her chest, a small smile on her face as she caught her breathe. Jackson smiled down at her as he caught his breathe and climbed down from his desk.

His legs were still weak and he part sat-part fell into his desk chair, wincing as his sensitive cock head rubbed against the rough material of that composed the seat of the chair. He almost fell asleep right there in his chair, but he forced himself to get up. He grabbed his towel off of his door and headed to the bathroom.

Cat had tossed on one of her sexy teddies to go to the bathroom. She hadn't expected anyone else to be up and she didn't feel that just having had an orgasm was any reason to stop feeling sexy. She loved walking around the dark apartment after she masturbated. She loved how the cool are would rush up against her bared and soaked pussy, and how her Teddy showed nothing, but hinted at everything. The exhibitionism of it thrilled her; wandering around her apartment while reeking of sex and almost nude would almost make her want to do it again.

She exited the bathroom; planning on going out to the enclosed porch for a bit before bed. It was poorly ventilated and cold, but there was something wonderful about sitting in the cold night air after a sweaty orgasm. She began to softly hum to herself, reveling in her post orgasmic rush, when she almost ran right into Jackson. "Oh, shit," she let out. "Damn, Jackson, you scared the shit out of me."

Jackson gave an apologetic smile and said "sorry about that," not wanting to admit she had scared him too. He backed up to let her pass and stood in the faint beam of light from a street lamp outside. He watched her as she passed. Her long auburn hair was in a messy bun and her face was still a bit flushed. Her purple teddy clung to her body and he could make out the faint outlines of her nipples pressed against the fabric. The shimmery material hugged her stomach and waist; he allowed himself a slight smile when he couldn't make out any interruption in that fabric that would suggest there were panties lying beneath.

Cat glanced at Jackson as she walked by and let her eyes linger until they briefly widened with surprise. She gave Jackson an enigmatic smile and quickly walked back to her room. She closed the door behind her and let the teddy roll of her shoulders, and stood naked in the moonlight thinking of Jackson. His sweaty hair had been plastered to his face, his cheeks were flushed, and he had cum his chest. It had to be cum. He had made a halfhearted attempt to wipe it off, but it had invisibly held his chest hair down. It had to be cum. He had been masturbating to her. Her orgasm had set him off. She crawled into bed allowing the sheets to rub her nipples and sensitive lips. She lay on her stomach and slipped a finger into her pussy. "Oh, dirty boy; you dirty, dirty boy," she softly moaned to herself. Arousal was burning in her pussy and desire in her chest. She slipped two fingers into her pussy and let out a breathy sigh of pleasure. She pulled her fingers up to her lips and licked her arousal, loving the way she tasted.

She grabbed a pillow and pulled it down between her thighs and rubbed her wanton clit against its fabric; her lips spread wide as her hips begun bucking the pillow in barely contained circles. A flurry of images flashed through her mind as she fucked her bedding: a hard cock belonging to a faceless stranger taking her from behind, Jackson masturbating to her moans, the wet pussy of a former lover—all of them lasting for just a second before another flash of pleasure caused her mind to go blank.

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