My Naked Roommate
Marley Quinn
My Naked Roommate
by Marley Quinn
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Table of Contents
Table of Contents
One Special Condition
The First Hour
Playtime on the Sofa
A Man’s Perspective
A Girl Likes It
Dear Diary
Riley Needs
Pushiness and Candor
Magic Fingers
Roberto
Oopsie
Spoilsport
Enchanting
Overwhelmed
Natural Instinct
Time to Order
Lover Not a Fighter
Yours Forever
Lucky Bastard
For a Moment There
Two Jobs
Time for Your Dessert
What an Amazing Couple
Nobody Wants Romance
Chicago Eats
Hearing Bells
Gas Company
Talk First
California Sunshine
Touching Grass
The Perfect Man
A Box of Chocolates
Master at the Art
Professor
Save it for the Camera
Confetti Falling
Spanking Session
Make it Rain
Head Over Heels
Two Tiny Hands
The Big Finale
My Prince
Public P
Marry Me
Green Dreams
Rabbit and Wolf
Dogs in the Neighborhood
The Sweetest Dish
Little Bridge
The Best Thing
Too Clueless
A Turn for the Worse
Family Reunion
Goodnight, Mother
Strange Dreams
Lily
The 19th Hole
Planet Skye
Bitter and Sweet Together
2-for-1 Special
In Your Dreams
Cock of the Walk
Black
In the Doghouse
Another Level of Trouble
Digger
Washington Park
Crack House
The Castle
Everybody Goes Home
True Spirit
Sweet Dessert
Underground Life
Passion and Pain
Outlaw
Manifestation
One Special Condition
“Sorry, man,” said Bill. “I hate to leave you in the lurch like this, but I’m sure you’ll be okay. And be sure to come visit me out in California!”
Wesley sighed. He was happy for Bill and his new job, but losing his roommate stung. How was he going to be able to afford rent, now?
Wesley was already working ungodly hours as a food delivery driver, and life in Chicago was expensive. If he couldn’t find a new roommate, he was toast.
The next day, Wesley placed an online ad that read: “Roommate wanted. One bedroom available for rent in beautiful downtown loft. Full amenities. Easy access to public transportation” along with his phone number and email address.
He got a few responses the first day, but one was clearly from a crazy person and the rest seemed disinterested when he told him how much they’d have to pay every month, including utilities.
Hey, it was a tight market, and prices were just going up. Wesley just prayed that he’d find someone who could afford to move into his apartment. Otherwise, he might just have to go live with his parents.
The next day, he got a call in response to the ad.
To his surprise, it was a woman on the other end, and she didn’t seem perturbed in the slightest when she found out that she might be sharing the apartment with a guy. In fact, she sounded a little eager about it.
She introduced herself as Skye and said that she was a freelance writer who mostly worked from home.
It sounded almost too good to be true, but Wesley wasn’t going to look a gift horse in the mouth. He set up a meet at the apartment for the next afternoon at three o’clock.
Right on time, the doorbell rang, and Wesley rushed over to answer the door. When he opened it, his jaw nearly hit the floor. The woman standing outside was a stunning brunette with long, waist-length hair and a petite figure.
“Hi there. Are you Wesley? I’m Skye,” the woman said, and Wesley was so dumbfounded he nearly failed to accept her handshake.
“Y-yes, that’s me. Come on in! Come on in,” said Wesley.
He then proceeded to give her the tour, still marveling that such an attractive young woman was even considering moving in with him and becoming his roommate.
“Well, I must say, this is a nice place you have here,” said Skye. “And I really like the location! So close to restaurants and clubs and all the other stuff that living downtown offers.”
“Um, yeah, it’s p-p-pretty great,” stammered Wesley.
“I’m definitely interested,” said Skye. “But if I do move in here, there’s one special condition.”
“Um... what’s that?” said Wesley, feeling his cheeks burning with a fiery heat.
“I know it’s a bit unusual,” said Skye. “But I absolutely refuse to wear any clothes when I’m at home. I just find them so constricting, you know?”
Wesley gulped.
“I just love the feeling of being naked and in my own skin,” said Skye. “That won’t be a problem for you, will it, Wesley?”
“N-n-no,” said Wesley.
“And just so we’re clear,” said Skye. “Me being naked isn’t an invitation to any kind of... you know, physical intimacy between us. Some of my former roommates got the wrong idea, so I just want to make sure you’re in agreement.”
“Um, sure, yeah, yeah, cool,” said Wesley, using one hand to scratch the back of his neck, which had become incredibly itchy for some unknown reason.
Skye laughed. “Like, it’s okay if you want to look. Obviously! But no touching, okay?”
“Y-yeah, sure, sure,” said Wesley.
“Okay, so I guess you don’t mind me being naked around your place,” said Skye. “I mean, I can always put on some clothes whenever company comes by or anything. But the rest of the time, I’ll be naked. Are you sure you’re cool with that?”
“Y-yeah, sure, sure, definitely,” said Wesley.
“Awesome!” said Skye. “So, where do I sign?”
In the kitchen, as Skye signed her name on all the dotted lines, Wesley watched her, picturing in his mind what she would look like without her clothes on. I mean, she was incredibly gorgeous already. What would it be like when she was naked?
Would he be getting erections constantly? And what would he do about it? Was he going to turn into some kind of chronic masturbator? Or would he eventually get used to seeing her naked and it would become an ordinary, everyday thing?
Wesley didn’t know. All he did know was that his cock was so hard that it threatened to push straight through his boxers and rip open his jeans.
“Okay, that should do it,” said Skye. “So, I’ll see you tomorrow around nine? A couple of my friends will be helping me move in.”
“S-s-sounds great,” said Wesley. “I’ll probably be working then, but I’ll see you around lunch, I guess.”
“Oh my,” said Skye. “I completely forgot to ask you what you do for work. How rude of me!”
Wesley blushed. “Oh, it’s okay. I’m just a food delivery driver. You know, for the apps.”
“Well, everyone has to eat!” said Skye, favoring him with a smile.
“Y-y-yes they do,” said Wesley.
“Well?” said Skye, looking at him with one hand on her slim hip.
“Uh?” said Wesley.
“The key, silly. I’m your roommate, now,” said Skye.
Wesley blushed. “Oh, right. Sorry.”
He then dug around in the kitchen drawer until he found Bill’s old key and then handed it over. Skye slipped the key into the pocket of her pants and gave him a flirty wink that got his heart racing.
Whew, dear god. She hadn’t even moved in yet, and already he was getting excited.
Wesley stood there like a statue as Skye made her way to the front door and then exited the apartment.
After she was gone, Wesley did a fist pump. He couldn’t wait to see what tomorrow would bring.
The First Hour
As a cold rain fell over the city, the orders for food delivery skyrocketed as they always did. Wesley had to hustle to make his delivery times, and even then, he was still late on a few orders. Luckily, though, none of the customers gave him less than a five-star rating.
With his scooter sounding as tired and worn out as he was, Wesley finally managed to close out the apps and then make his way home.
He was so tired that he completely forgot that Skye was moving in today, and so it took him a moment to realize why there was a large U-haul truck outside his apartment.
The front door was unlocked, so Wesley walked into his apartment to the sound of a group of people talking in the kitchen. As he stepped inside, they all turned and looked at him.
“Hey, there he is!” said Skye. “Hey, Wesley, I want you to meet a few of my people. This is Jim, Letitia, and Zayne.”
“Hey,” said Wesley, setting his helmet down on the kitchen counter.
“Guys, this is Wesley,” said Skye. “The man who was gracious enough to agree to let me become his roommate.”
“Uh oh,” chuckled one of the men.
“You’re a good man, Wes,” said the other man with a laugh.
“Oh, don’t listen to them,” said Skye. “Anyway, we’re all about wrapped up here, right guys? So, I’ll see you at seven. Pizza’s on me for helping me move.”
Wesley watched as Skye and her friends chatted for a few minutes more before she shepherded them to the front door and out of the apartment.
Skye then walked over to the living room window and watched as the U-Haul carefully eased out of its parking spot and then zoomed off down the street.
Skye turned and faced Wesley, a huge grin on her face. “Well, you know what time it is!”
Wesley gulped. “Yeah, um, yeah. Time for you to take off your clothes, right?”
“You got it!” said Skye, smiling. “Just don’t forget our agreement, all right?”
“Y-yeah, y-yeah, I remember,” said Wesley.
“Good,” said Skye.
Wesley felt his breathing quicken as he took a seat on the couch, not quite having the courage to watch her undress.
Looking over, he saw Skye standing there, completely naked. Her breasts were small but perky. She had a tiny waist and long, toned legs. She was a vision of loveliness, and Wesley felt his prick stiffening in his jeans.
“Wow,” said Wesley.
“What’s that?” said Skye, turning to face him.
“Uh, nothing,” said Wesley. His eyes dropped to the floor, unable to maintain eye contact with her. “Just saying. You look amazing.”
Skye giggled. “Thank you, but I think it’s you who looks amazing. I mean, those muscles in your arms are pretty hot,” she added with a wink. “You must get quite the workout, delivering food all day.”
“R-r-really?” said Wesley. “I mean, yeah, I guess I do.”
“You really ought to consider taking your shirt off. I think you’d feel more comfortable,” said Skye, tipping him a wink.
But before Wesley could say anything in response, she strutted off to her bedroom, giving him a perfect view of her gorgeous backside.
As soon as she was out of sight, he ran to his bedroom and closed the door behind him.
His cock was so hard that he struggled to pull down his boxers, but at long last, he managed to free his penis from its sweaty prison.
As images of the naked Skye danced in his head, he used his right hand to begin furiously stroking his shaft. It felt so good, and it only took a minute or two before he felt his balls tightening up, ready to release their pent-up load.
Just then, he heard Skye knock on the door.
“Uh, hey, Wesley?” said Skye. “Can I come in for a quick second?”
“Uh, wh-what is it?” said Wesley, his voice strained and desperate.
“I was wondering if you had a pen I could borrow. I seemed to have misplaced mine, and I just wanted to jot down some...” said Skye, her voice trailing off when she caught sight of him standing there, one hand on his engorged cock.
“S-s-s-sorry!” exclaimed Wesley, his face going beet red with embarrassment.
Skye giggled. “Don’t be sorry. I came in here hoping to catch you doing this,” she said.
“W-w-what?” said Wesley.
“Let’s just call it a test,” said Skye, giving him a saucy wink. “And you passed.”
“Oh,” said Wesley.
“Be careful not to get any cum on that rug!” called out Skye as she turned and left his room. “It looks pretty nice.”
After Skye was gone, Wesley stood there for a long minute, utterly confused about what had just happened. But the pressure in his balls soon jolted him out of his reverie.
It only took about ten seconds before a hot load of jizz sprayed from the end of his cock, which Wesley used an old sock to absorb.
When he was done, he sat down on his bed, still dazed by all that had transpired. Skye had only been living in his apartment for an hour, and already things were getting crazy.
What in the world was going to happen in the future?
Playtime on the Sofa
Over the next few days, Wesley went to work, gulped down some food, masturbated, and then went to sleep, pretty much in that order.
It didn’t take long for his cock to become red and sore, but the sight of Skye walking around naked in the apartment never failed to arouse him.
With his finances now in better shape, Wesley began working fewer hours. That gave him more opportunities to peep through the crack of his bedroom door to watch Skye as she moved around the apartment.
Sometimes, he’d see her pass by the window, utterly oblivious to the risk of someone on the street seeing her.
Other times, especially when she was in the kitchen, it felt like she was doing a lot of unnecessary bending over so that he’d get a good look at her backside.
Even when Skye was in her room, working, she never closed the door, and so he’d get a jolt of electricity running down his spine whenever he passed by on the way to the bathroom or the kitchen.
But she never seemed to mind his constant ogling. Wesley marveled at the fact that she always seemed so blase about the fact that he was always sporting a raging boner in her presence.
Skye cooked a meal for the two of them on a few occasions, which was all right, as sitting down at the table gave Wesley a modicum of relief with his bulging crotch safely out of sight.
It was when she invited him into the living room to watch a movie that really tortured him. Skye would lounge lengthwise on the sofa, stretching and moving her legs, a sight so distracting that he couldn’t pay any attention to what was on the screen.
One night, after she insisted on him joining her for a viewing of one of her favorite 90s rom-coms, Wesley looked over and was shocked to see that Skye was playing with herself.
When she saw him looking at her, she gave him a wink and went right on touching herself.
Wesley nearly came right there in his pants as he watched Skye let out a soft moan as her fingers stroked and fondled her clit. Skye then let in a sharp gasp as she thrust two of her fingers straight into her slit.
For several agonizingly long minutes, Wesley stared with his mouth hanging wide open as Skye brought herself to orgasm. As her abdomen muscles began convulsing, her eyes briefly rolled back in her head, her breath hard and ragged.
A moment later, she seemed to have recovered. Looking over at him, Skye smiled and then dipped one finger into her sopping wet pussy before bringing it to her lips, making loud slurping noises as she sucked it dry.
That was all it took for Wesley’s cock to spasm in sympathetic lust, filling his boxers with yet another stinging hot load of cum.
To the sounds of Skye’s laughter, Wesley got up and fled to the bathroom, where he spent the next several minutes trying to clean himself up. If something didn’t change soon, he was truly going to lose his mind.
A Man’s Perspective
The next morning, Wesley was just about to head out of the apartment on his way to work when his phone rang. It was his mother, informing him that she’d be in Chicago for a few hours thanks to an unexpected layover.
Wesley was more than happy to meet her at the airport, but she insisted on swinging by his apartment, saying she wanted to “check in on her boy.”
Gulping nervously, Wesley turned around and walked over to Skye’s door. “Um, hey, Skye, can I come in for a minute?”
“Sure!” said Skye. “What’s up?”
Wesley forced himself to stare at a spot on the back wall in order not to lose his train of thought. “Um, my mother just called. She’s going to come visit here tomorrow around two.”
“Oh, how delightful!” said Skye, clapping her hands. “But are you telling me this because you want me to meet your mother? Or because you want to give me a heads-up to put on some clothes?”
Wesley blushed. “Both, actually. I mean, my mom is pretty conservative, so I figured maybe you could put on a robe or something. You know, just to be polite.”
“Oh, Wes!” said Skye. “Of course! No worries at all. I’ve met plenty of parents before. I’ll be good. And besides, I’m planning to go out for some drinks with my friends tomorrow afternoon. Can’t go to the bar naked, at least not in the state of Illinois!”
“Oh, g-g-great,” said Wesley.
“Hey, Wesley, while you’re here, can I get your opinion on something?” said Skye.
“Um, sure. What?” said Wesley, gulping nervously.
“Come closer,” said Skye. “I need your opinion on something I’m writing. I could really use a man’s perspective.”
Cautiously, Wesley made his way over to Skye’s desk until he was standing right next to her. Skye reached up and took his hand, extending it until it was nearly touching the screen.
At first, he couldn’t make out the words, but then he realized that he was reading some kind of erotica story about a girl who was fantasizing about having sex with her roommate.
“What do you think?” said Skye. “Pretty hot, right?”
Wesley nodded, his throat as dry as sawdust.
“Here’s the problem, though,” said Skye. “I can’t seem to decide whether the guy in this story is supposed to be sweet and gentle, or if he should be rough and forceful. Which do you prefer?”
“Um, well, I think, um, I think I like, uh... both equally,” said Wesley, his voice cracking slightly.
“Really?” said Skye. “Hmm. So tell me. Should her roommate just throw her down on the sofa and fuck her hard and fast? Or should he cuddle with her in bed until she’s all hot and bothered?”
Wesley swallowed hard. “Um, I, I think, um, I don’t know. Maybe he should do both?”
Skye grinned. “Interesting. I tell you what, Wesley. I’ll just leave it to you to decide. Whatever you like best is what I’ll write.”
Wesley shook his head. “Um, what do you m-mean?”
Skye giggled, leaning forward so that her tits were grazing the back of his arm. “Come on, Wesley. Don’t you know that girls like it when the guy takes the initiative? It’s so much hotter that way.”
Wesley’s face went beet red, and he yanked his arm out of Skye’s grasp before turning and fleeing her room.
With the sound of her laughter ringing in his ears, he ran out of the apartment and hopped on his scooter, only regaining his composure several blocks later.
A Girl Likes It
The next morning, Wesley did his best to tidy up his room, even though he knew that his efforts would never pass muster in his mother’s eyes.
Still, though, he didn’t want her to walk in and find a bunch of his old socks lying around, crusty with dried jizz.
The morning rush passed by uneventfully, and then he locked up his scooter and took the shuttle bus out to O’Hare. His mother’s plane was only 10 minutes late, so he thankfully didn’t have to wait too long before seeing her burst out of the arrivals door.
After the obligatory tight motherly hug and sloppy wet kisses on each of his cheeks, Wesley slung her carry-on bag over his shoulder, and the two of them headed for the exit.
“So, Mom, I think I told you that Bill got a job in California, right?” said Wesley.
“Yeah, one of those tech firms or something,” said his mother.
“Right, right. Well, listen, I have a new roommate now,” said Wesley. “Her name is Skye.”
“Oh, really? A female roommate? Very interesting,” said his mother. “What is she, some old divorced lady or something?”
“Um, no,” said Wesley. “Actually, she’s a couple of years younger than me.”
“Hmm. And what does this female person do for a living?” said Wesley’s mother. “Chicago’s an expensive city to live in.”
“Actually, she’s a writer,” said Wesley, feeling his face flush warm as he remembered the story that she had been writing.
“Oh, a writer, eh? Like a novelist?” said Wesley’s mother.
“Um, more of a short story writer, I think,” said Wesley.
“Well, have I read anything that she’s written?” said Wesley’s mother.
“Um, no, I don’t think so,” said Wesley, gulping hard.
Thankfully, on the shuttle bus ride into town, the conversation turned to tales about his father learning how to golf and how much his mother looked forward to meeting members of her online book club when she arrived in Florida later today.
When they arrived at his apartment, Wesley walked up to the door and knocked a couple of times. “Skye? Are you home? We’re coming in now, me and my MOTHER.”
Wesley’s mother gave him a quizzical look but said nothing as she followed him inside. Wesley breathed a sigh of relief when he looked around and didn’t see Skye.
He then invited his mother into the kitchen for a cup of tea, grateful that Skye’s bedroom door was closed as they passed by.
A few minutes later, Wesley looked over and saw Skye walk in. She wasn’t naked, but she was wearing high heels and a skin-tight dress that was so short that the hem barely covered her crotch.
“Oh, you must be Wesley’s mother,” said Skye, extending her hand. “He’s told me SO much about you.”
“Oh, he has, has he?” said Wesley’s mother, a suspicious look on her face as she took in the sight of the younger woman. “And you must be his roommate, Skye.”
“That’s me!” said Skye, all smiles. “Forgive me for not staying long, but I’m just off to meet some friends. But it was really nice to meet you.”
“Yes, um, lovely to meet you, too,” said Wesley’s mother.
“Enjoy your stay in Chicago!” said Skye. “Um, hey, Wesley, could I talk to you for a quick second in the living room?”
“Um, s-s-sure,” said Wesley. “Be right back.”
“Don’t mind me,” said his mother. “I’ll just be in here, cooling my heels.”
Nervously, Wesley followed Skye into the living room. “What?” he hissed.
“What’s with you?” said Skye with a laugh. “Your mother seems nice. I can see where you got your good looks.”
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