Old Friends, New Roommates

***Author's Note: I have been writing for years but this is my first upload to Literotica. In general, I tend to be EXTREMELY wordy and my stories therefore extremely long (hundreds of pages). This is a first attempt at something much shorter. I hope you enjoy.***

"The rules are simple." Sherri was rearranging pillows and blankets on the floor around her. "You can do anything you want to get yourself off, you just aren't allowed to intentionally distract or impede the other contestants from getting themselves off. First to cum, wins."

Tim and Kara sat and glanced at each other with cocked eyes. Sure, they were all friends and did happen to be all nude... but were they really going to do this?

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The three had known each other for almost as long as they could remember. Kara's parents lived on the street before she was born. Tim's parents moved in next door to Kara when he was just a baby. Sherri moved in across the street the summer before Pre-K started.

They were best friends from an early age. It helped that their parents were all progressive and encouraging of their mixed-gender friendships and, even through puberty, did not stop them from their constant contact with one another. If one went, so did two more. All activities were done in 3, all activities were coed. The trio had remained drama free their entire youth. Literally none. The worst thing that ever happened was Sherri getting her period while the three of them were out playing. Tim noticed the spotting in her shorts, said it was gross, and she ran home upset. Tim, after telling his mom the situation at home, received a thoughtful explanation of what had happened and, without prompting, wrote Sherri a note apologizing for his reaction and hoping it would not stop them from hanging out.

Over the course of their youth they had seen each other nude plenty of times. When they were little they took baths together. As they got older they often changed in the same room after using Kara's family pool. As their bodies changed they watched each other develop with curiosity but not the self-consciousness or shame that was so often associated with puberty. Kara was the first to grow pubic hair. Sherri was the first to develop breasts. Tim was (obviously) the first to have an erection. They saw each other, they even innocently touched each other, nothing more than that.

And yet there they were, more than 15 years later, 30-somethings living together as roommates for the first time in their lives, naked and being challenged to cum.

Kara was an artist. After dropping out of college she had lived a bohemian lifestyle, working commission projects and as a contract bartender to earn enough money to fund her next adventure. To date she had traveled to 43 countries and visited every continent.

Tim had jumped from job to job since graduating with a masters in computer science. Programmer. Network Admin. Back to school for an MBA. National Strategic Director of Business Relations. He had been very well paid and loathed 80% of the days he was at work. So, he sold his house, quit his job, ended a long-term relationship that he and his girlfriend both agreed just wasn't a permanent fit and moved in with Kara.

Sherri had been an English teacher but had quit soon after getting married. She lived a relatively glamorous life; big house, fancy dress, black-tie fundraisers and social parties. As it turned out she was unable to have children. As it turned out that her husband could, and did, with a long-term mistress he had been hiding from her. The divorce was quick, she left with her car and a large settlement and, when hearing that there was a third room to be occupied in Kara's apartment, jumped on the opportunity to be with her friends again and "start over."

It was as if the last decade and a half never occurred as living together became the most natural thing they could have done and, for Tim and Sherri, living a "simpler" life turned out just to be what they needed.

"You make it sound like you thought I lived like a third world peasant," Kara laughed when Sherri commented on how nice the apartment was. "I may not be rich, but I still have certain standards."

It had only been a couple of hours since they had finished moving Sherri into the apartment and all of them were in the bathroom. Tim was in the shower, Kara was on the toilet peeing, Sherri was standing at the sink, nude, having just finished showering and was going through her post-shower moisturizing and skin-care routine.

"I've seen your Instagram pics, K. It isn't like you have a problem with third world living."

"All I hear is 'blah, blah, blah'," Kara responded as she wiped and got off the toilet.

The two smiled at each other and Kara began to get undressed, slapping the curtain of the shower.

"Timmy, get your tiny little wiener out of the shower. I need to get clean."

All three were nude by the time the water shut off and Tim pulled the curtain back, gesturing for a towel and responding to Kara.

"Considering your last Tweet lamented on how you haven't been laid in almost 7 months, you probably shouldn't insult the only available cock in your life."

"Available, but unwanted, Honey. Now move so I can get in."

Tim smacked her ass right as she pulled the curtain shut.

Right back to normal.

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It was only a couple of weeks later that they found themselves in the living room, drunk and nude with Sherri suggesting the masturbation competition. Looking back, it could have been a weekend or it could have been a Tuesday, with all 3 of them basically living non-corporate lives the concept of calendars became temporarily unimportant.

It had started at dinner. All of them had been talking, joking and flirting with one another and the drinks had been pouring liberally. The first to start to disrobe was Kara, who exclaimed that she was hot and matter-of-a-factly took her shirt off as they all stood around in the kitchen. She rarely wore a bra in the house.

By all accounts, Kara had physically aged the best of their group. Maybe it was due to her non-"standard" lifestyle and self-reported lack of stress. Maybe it was due to genetics. Whatever it was, her body had barely changed since they were 18. 5'7", 122lbs. Perky, high-chested B-cup breasts. She was long and lean like a ballerina. Her curly, surly light-brown hair would hang in between her shoulder blades if she let it down though she normally had it up in some fashion. She rarely wore makeup and insisted on having at least some pubic hair though almost always kept the silky tan patch neatly groomed. Her nipples were small, pink and got puffy when she was aroused. Her inner labia protruded ever so slightly from her outer lips and she had delightful dimples as a dominant visual over her consensus best feature, her curvy, round bubble butt.

By the time they got to the living room, already buzzed and knee-deep in updated conversation of sexual preferences, kinks and turn-ons, the only articles of clothing left on the three of them were Tim's low-cut running socks and Sherri's lycra satin hipster thong.

"Oh, my God," Sherri exclaimed as she threw herself on top of Kara, knocking both of them onto the couch, "how the hell are your tits still so amazing when I just have these bags of sand?!" She was feeling her friend up in exaggerated fashion, fondling her breasts like a softcore late-night cable flick.

Sherri had always been significantly more curvy than Kara... or Tim for that matter. Not to say that Tim was curvy, but weight had never been one of his personal hangups. Unlike Kara, to whom it came naturally, Sherri had to work for her body. In her past life that meant regular gym, yoga, sauna and massage. In her new life she would just have to figure things out. She was only 5'1" though filled out nicely at 135lbs. Her breasts had always been large, even starting in middle school, and though diet, exercise and age had made them a bit smaller and a little less full, she still could easily fill out a D-cup bra. Her waist was narrow, her stomach soft and inviting, her hips were somewhat wide and maternal. She pretty much never had pubic hair and claimed, after years of having it waxed, she doubted it would ever grow in even if she wanted it to. Her labia were pronounced (affectionately referred to as her "butterfly wings") and her areola and nipples were each appropriately sized to suit her breasts. Her hair was dark, her lips were full, she was the "goddess of the group."

"Your tits are fantastic and you know it," Kara giggled in response as she tried to fend off her new roomies ticklish advances. "Tim, tell her!"

Both of the girls' faces flew to their nude friend, who stood in the doorway, a drink in his hand, a grin on his face, not a care in the world.

He had been a decent high school swimmer back in the day, not good enough to win championships, but good enough to win most of his meet-to-meet races. His body, though a little fuller with age, still showed signs of his gym-class-hero glory days. 6'2" tall, 205lbs, lean and strong. His shoulders were wide, his hips were narrow, his dick was a pleasurable seven-and-a-half inches hard when he became aroused. His hair had once been a light brown but now betrayed his years and was prematurely greying around the temples. Though, true to sexist norms, what would be shunned on most women was lauded as wise and distinguished on him.

"Ladies, ladies, ladies," he sighed as we walked over to the couch with them, plopping himself on the edge next to their bodies and wrapping an arm around the shoulders of Sherri. "You are both fantastic. Beautiful, sexy, perfect tits and all."

The girls laughed as Kara's request had all been an obvious joke. Though both, secretly, appreciated the fact that Tim had never even jokingly disparaged them, even his sarcastic responses were always positive.

The conversation continued along the same path it had been and more specifics had been demanded at each step of the way. By the time Tim's socks finally came off, the topic was, very specifically, orgasms.

"Wait," Sherri said to Kara in a voice of non-belief, "you're saying you haven't cum in 7 months? I don't think that's healthy or, at least in my case, even possible."

"No, I didn't say I hadn't cum. I said I haven't gotten laid. And what do you mean it's not possible? Of course it's possible."

"Nope, not for me." To the minor shock of her friends, Sherri spread her legs open and brazenly spread her butterfly wings for her audience, pointing out her clit. "My love button gets so hot it's like an addict who needs another hit. Plus, nobody knows how to please me like me. I can get myself off so quick there is no need to not."

"Oh, give me a break," Tim chimed in, "everybody knows just what to do to get themselves off. You're no more special than anyone else."

Sherri slammed her legs shut and pointed directly at the only male in the room, fire in her eyes.

"Challenge!"

"What?!" Kara was the one to respond.

"I challenge both of you! I bet I can make myself cum before either one of you."

"Please," Kara retorted with a roll of her eyes. "How would we even know if you came? You could fake it and just say it happened."

The concept of how ludicrous the challenge had been to begin with wasn't even brought up.

"Oh, Honey," Sherri replied condescendingly to her audience, "have we been apart that long? Have all of our late night conversations been forgotten? I'm a squirter. That's how you'll know. For Tim, it will be obvious. And, for you, well, I will even go so far as to let you just tell us when it has happened. I trust that you'll be honest since I know I will be finishing first anyhow."

Tim, who had always let the girls take the lead when it came to their sex talks, decided to see if she was serious.

"Okay, I'll bite, whiskey-dick and all. I think you're full of shit. Any other rules?"

Sherri had already gotten up to get a blanket and some pillows.

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They were arranged in a triangle, all facing one another. Tim and Sherri were both leaned up against the couch. Sherri had set up a little lounge area for herself, her legs splayed open wide, her fingers and hands at the ready. Tim was next to her, in a somewhat similar position to Sherri, cheating and attempting to get himself hard, nervous that the booze and his age would betray his attempt. Having moved the coffee table, Kara was on her knees at her friend's feet, a pillow between her legs, pressed tightly up against her pussy. True to her historical form, one would never have known how competitive she was from the look of her, she was as calm as could be.

"Let's do this," Sherri announced. "Go."

Though it was a race they each started slowly, taking cues from one another as to methodology and for their own stimulating arousal. Kara rocked back and forth on the pillow and caressed her breasts. Sherri used a couple of spit-slick fingers to rub her clit while her opposite digits rimmed little circles around her asshole. Tim just took it all in, no longer worried if he was going to get hard, immediately turned-on by the actions around him.

Sherri was the first to moan. Whether she was truly a squirter or not, her opened legs displayed just how wet she got when her clit was stimulated, her entire pussy lips slick with her own fluid and dripping to her puckered sphincter below.

Kara's nipples were puffy and inflamed, little hats on her flushed breasts. She had closed her eyes and her breathing was rhythmic to the thrusts of her hips into the pillow.

Tim had stopped even attempting to finish. He lazily stroked his erection, more entranced by the visuals in front of him, wanting to make sure he took it all in, confident he could use the images to finish himself off later.

It was a few minutes in, more than five but less than 10, when it became obvious that Kara was climaxing. Her areola were no longer puffy, rather hard and tight, her nipples mimicking pencil erasers on the ends of her tits.

Sherri attempted to speed up her movements in response, driving two fingers into her dripping cunt to complement the two working her button and knew that she would orgasm soon, but it would be too late.

Tim was simply mad at himself. His dick was hard, his balls were full. His hindsight and decades of experience with getting himself off told him that if he had just put some effort into things he most likely would have finished minutes ago. Watching the girls was so hot and he knew the memory, while good, just wouldn't be the same later that evening. He considered finishing anyway when Kara collapsed onto the floor in between him and Sherri, tiny shivers of pleasure still emanating from her body.

"Goddamn it," Sherri grumbled in frustration as she gave up and let her body go limp, arms to her sides. "I was right there."

"Good game, good game, good game," Kara mumbled. Her friends smiled, appreciating the use of the inside joke they had used with one another for years, recalling the days of youth sports and friendly competition.

The pillow she had been grinding against had a milky wet spot on it and, if she had faked her orgasm, she was extremely convincing in doing so.

Tim scooted his butt down on the floor and lay himself down next to Kara, his erection pointing directly at his bellybutton. Sherri squirmed on the floor behind Kara for a moment before getting up, stepping over each of them and laying down on the opposite side of Tim, draping one of her legs over his thigh.

"Uhg," she moaned, "I suppose I only have myself to blame for this."

"What's that," Tim asked.

"Just that I am now all worked up and frustrated."

"I hear ya, girl," Kara croaked from the floor, obviously starting to come to her senses.

"What are you talking about?" Sherri was incredulous. "You won! How can you possibly be frustrated?!"

Kara slowly sat up, facing her friends. "Welcome to my world, the cross I bear. I need to have multiple orgasms." She opened her legs wide, displaying herself garishly. She was completely soaked, her lips puffy, her clit engorged and presenting itself, desperate for attention. "The good news is that they tend to come faster after the first one. Even if it isn't till a little while later. The bad news is that if I don't have at least 2 or 3, I am absolutely miserable."

"Faster?! You just beat me and I thought I was the record holder!"

"Try the pillow, man. I was skeptical it could be better than the ol' fingers myself but I am a total convert now."

There was a moment of calm as everyone still seemed to be processing what had happened.

"You know, this is what I miss most," Kara said, breaking both the silence and the stillness of the room, reaching out and taking Tim's erection in her hands, "the feeling of a man." One small hand wrapped around his engorged cock as the fingertips of her opposite hand traced themselves around its bulbous, swollen head, a tickle of pre-cum present. "I love how warm it is. How hard yet how soft it can be. How you can feel its pulse, like it has its own life."

"Oh, my God, fuck this!" Sherri popped up from her position with a look of hurried panic on her face. "Where is that pillow? I can't just sit here while you are talking about stuff like that." She grabbed the pillow Kara had used, flipped it over, and knelt over it, replicating what she had watched her friend do, working it up against her throbbing sex.

Kara ignored her and continued her focus on Tim's dick, lazily stroking and squeezing it, not for any particular reason other than how she liked the way it felt.

Tim said nothing, he laid quietly and still, taking in the visual of one roommate riding a pillow and the the delightful sensation of the soft feminine hand on his cock.

"You're right," Sherri panted after a few minutes, "this is nice. I haven't done this since I was a kid."

"Told ya'," Kara responded absentmindedly.

"Yeah, but I need a bit more. I like my ass played with, the angle is strange on this."

Tim and Kara watched for a moment before Kara gave him a look of confirmation that she was going to move, and set herself up behind Sherri.

"Lean forward," she instructed, gently pushing Sherri's torso down towards Tim. Though he could only see her apply a generous amount of spit to her fingers and then move her hand behind her, he could tell that Kara was playing with Sherri's ass. Sherri's response confirmed it.

"Oh, God," she moaned gutterally, her voice an octave below what it would have been normally. Her cheek was on Tim's thigh and, had he been flaccid, is dick would have been directly in front of her face. As it was, when she moved, her forehead would periodically drag itself up and down the length of his shaft.

It was driving him crazy.

Whether it was through ESP or the obvious motion his hips were making as he tried to guide his dick toward more constant contact, Sherri sensed his frustration and took him into her hands.

"This is probably my fault, isn't it," referring to his erection in between her own labored breaths and with no intent on getting an answer. "She is right, you do get to missing them. I've never said this before, but you have a really nice cock."

Tim remained wordless.

Sherri's breathing began to intensify and it appeared that she was coming close to an orgasm when Kerri pulled the pillow from in between her legs.

"What are you doing?" Sherri whined. "I was so close!"

"Enough of the bullshit," Kara responded, "let's make this count."

Tim watched as Kara laid on her back and scooted her head back between Sherri's legs. Though he again could not visually confirm what was happening, his suspicions were confirmed when Sherri gasped and moaned. Her response was enough to make his dick twitch in her hand, something she obviously noticed. Looking into Tim's eyes, she whispered.