Chapter 1

The idea of bunking with a roommate just seemed immature to Dan. As a forty-year-old man with a family, Dan believed he was far too old and past the point in his life when he should even consider living with some stranger. He had scoffed when his wife proposed the idea to him.

“A roommate? Jesus, Sarah, I’m forty years old,” he said, half laughing. “I’m not in college anymore.”

Like most American families, the economic downturn hit the Williams hard. The engineering firm that Dan was employed at for the last ten years went under, leaving the father of two unemployed. Luckily, Sarah was able to hold onto her job as a hospital administrator to keep food on the table.

Dan had been unable to find another job in his field or at the same pay rate in their hometown of Middleton, Illinois. Other companies in town seemed to have had a hiring freeze as Dan never heard back from anywhere he had submitted his resume to. In desperation, he’d just worked whatever odd jobs he could find to help keep his family afloat.

After two years without steady employment, Dan finally received a call from a firm out of Chicago. While the pay was much less than he was previously making, a regular influx of cash would help the Williams family get their lives back on track.

“Dan, we’ve gone over the numbers how many times? We’ll be able to save a lot more money if you split the costs with someone else.”

“I know, I know. I just don’t want to live with some random person, Sarah. At this stage in my life, I just want to be with you and the kids.”

Sarah made her way across the room and sat down on Dan’s lap, circling her arms around his neck.

“I know, baby, but think of it this way. The more money you save by having a roommate, the faster the kids and I will be able to join you in Chicago.”

Dan sighed. “You’re right. It’s going to be hard enough just being away from you and the kids, but if this gets us back together faster then so be it.”

A half smile spread onto Sarah’s face. “It’s going to be hard on all of us, but this is the best scenario in terms of our finances.” The smile on her face grew wider and she locked eyes with Dan. “And it’s not like this is forever. Once we’ve saved enough money and I can find a job in Chicago, the kids and I will be right there with you in a place of our own.”

Begrudgingly Dan faked a small smile so Sarah would feel that her efforts to comfort him were working. In an effort to put an end to his pity party, Dan joked, “I guess this move might put a damper on our sex life.” He feigned a thrust into her butt with his hips for a punchline.

The smile on Sarah’s face grew wider as she quickly shifted gears from comforting to flirty. She shifted her hips on Dan’s crotch and playfully said, “Oh, I don’t know about that. Between Skype and sexting, I’m sure we’ll be able to find a way to satisfy each other.” Her grin grew even wider, while naughty thoughts filled her head. Her fingers playfully danced along the skin of Dan’s neck. “Who knows, it might be nice to get away from the kids and come visit you in Chicago.”

Sarah and Dan spent the next week looking online exhaustively at places for Dan to live in Chicago. Due to the location of Dan’s new job and their budget, housing rentals were quickly eliminated from the equation. Many of the ideal locations close to Dan’s work were occupied, so the couple had to expand their search to apartment buildings in different parts of the city. After a few days, they booked several appointments to view different units in person.

Sarah took a few days off work and had her parents stay with the kids so she could accompany Dan on his hunt for an apartment. They drove up to Chicago on Friday with the plan to spend the weekend making their appointments and looking for other rental opportunities.

Over the course of the weekend, both Dan and Sarah began to become dismayed at the rental prospects in the city. Their short list of apartments grew increasingly shorter with each appointment.

The first apartment they visited would have had Dan sharing a unit with an older gentleman who was clearly a hoarder. The common area was used as a storage space for the packaging and garbage that this man had accumulated over the years. Even the room that would have been Dan’s was filled with a mountain of items that would need to be relocated before anything else could be moved in.

While the rest of the appointments were attractively advertised online, they were anything but in person. Either the state of the apartment was in disrepair or the quality of the roommate did not meet Dan’s expectations. After checking out all of the rentals on their list, Dan and Sarah had met several high-functioning drug users as well as some that were not so high functioning. They encountered a few cat ladies and even a man that presented Dan with a roommate agreement that he wanted to be signed which outlined how Dan was to conduct himself while in the apartment. The agreement tried to regulate when Dan would be allowed to use their shared Internet and for what purposes. It even went as far as requesting that Dan book when Sarah was to visit ahead of time to obtain the roommate’s approval.

The only appointment that had been acceptable to Dan would see him rooming with a female college senior. Sarah quickly shot down that option.

After visiting every apartment on their list, the couple returned to their hotel room dismayed. With his eyes closed, Dan slowly massaged his temples while sitting on the edge of the bed. “I don’t think I’m going to have a place to stay before I start work next week.”

“We’ll find something,” Sarah said and she moved behind her husband and wrapped her arms around his chest. “This city is huge, and there has to be somewhere that isn’t completely terrible.” She planted a reassuring kiss on Dan’s shoulder, letting her head rest there.

Dan stopped massaging his temples and brought his hand up to slowly stroke Sarah’s hair. “I just can’t believe every apartment we checked out was a bust.” He shook his head. “We had a list of promising spots, a few were even close to work and none of them panned out.”

Moving from her place behind Dan, Sarah got off the bed and stood in front of her husband with her hands on her hips. “We’re not gonna let this get us down. There is a perfect spot for you ... for us, here in Chicago. We just need to find it.” She shot Dan a genuinely warm smile that reminded him just how much he loved her. Even though she was strikingly beautiful, her caring and compassionate personality was what he loved most.

The smile quickly faded from Sarah’s face only to be replaced with a look of determination as she marched across the room to her purse. She wasn’t about to let her husband be homeless in a new city, and she certainly wasn’t going to let them sit around and mope in their hotel room. As a hospital administrator, Sarah was used to solving problems all day long. Whether the hospital was running low on a certain item or had a staffing issue, Sarah was always able to find a solution.

She quickly unzipped her purse and reached in, searching for her smartphone. While making her way back over to the bed, she began navigating the internet looking for newly posted rentals in the area. Dan watched her as she crossed in front of him, Sarah not taking her eyes off the phone as she moved onto the bed in a sitting position against the headboard. He admired her determination and quickly located his cell phone to follow suit.

After a half hour of unsuccessfully searching for a new listing that would be different from their other appointments, Sarah was almost ready to call it quits. I can’t give up. We need to find a place for Dan to live. What other websites should I check?

The answer quickly dawned on her. Before this pivotal decision, their searches were restricted to rental listing sites for Chicago and the websites of individual apartment complexes. Sarah then remembered the name of a website she had never visited, but had heard about on the news and from her co-workers at the hospital.

It was a website that she would eventually wish she had never remembered.

She quickly typed ‘craigslist.com’ into her phone’s browser and navigated to the page for Chicago rentals. Scrolling through the listings, Sarah quickly realized that there were a ton of apartments available for rent that she had never even stumbled across in her past searches. Maybe this is it!

A recent listing near the top of the page caught her eye. “Clean spacious two bedroom, quiet roommate”

She clicked the link and was brought to a page that had several pictures with a current time stamp on them. The pictures showed off a reasonably clean apartment that appeared to have a good amount of space. The bathroom, common area, kitchen and Dan’s prospective bedroom were all showcased and appeared much better kept than what the couple had already experienced throughout the weekend.

Staring intently at the screen, Sarah read over the description of the unit. Location, check. Price, check. Male roommate, check!

Before asking her husband his thoughts, she quickly sent the poster an email stating her interest and desire to see the unit in person. After the weekend they’d had, she wasn’t about to let this apartment go to someone else.

After clicking the send button, Sarah excitedly looked over at her husband. “I think I found you a place!”

Across town, a computer monitor flickered on, accompanied by a short beep notifying its absent user of a new pop-up notification. The sudden light from the screen illuminated an otherwise dark room, exposing an unkempt mess. Piles of dirty clothes littered the floor amongst dishes caked with what was once food. Every surface in the room, from the computer desk to the nightstand, was occupied by trash or other forgotten items under a thick layer of dust.

A shape on the bed stirred in response to the sudden intrusion of light. Slowly, the shape of a man sat up and kicked his legs off the side of the bed. The light from the computer exposed a body that matched the room’s level of upkeep. A t-shirt which was originally white, now a pale beige, was dotted with stains from an unaccounted number of days’ worth of food and was littered with small holes. The fabric of the t-shirt was fighting to contain the protruding belly that hung over an equally neglected pair of boxers.

The man got up from the bed and expertly navigated the maze of dirty laundry and dishes scattered on the floor. As he plopped himself down in the computer chair, he ran his stocky fingers through his wiry hair. He used the mouse to click on the notification, which revealed a new email in his inbox. Licking the remains of the night’s takeout dinner from his lips, he began reading the new message.

Hello there... Soon the man’s fingers were racing across the Cheeto-encrusted keyboard. The speed at which he typed amounted to the most physical exercise he had experienced in weeks. The email was from a woman named Sarah asking about his craigslist apartment posting on behalf of her husband. She wanted to come and see the unit as soon as possible. I’ll show her my unit all right.

Satisfied with his reply that the couple could view the apartment anytime the following day, he signed the email ‘Lester Marshall’ and pressed send.

The rush of corresponding with a female stranger over the Internet awakened Lester’s dick. He greedily clicked the Mozilla Firefox icon and began browsing his bookmarked porn sites.

Excited by the prospect of finding an actual apartment to rent, the Williams left the hotel early to have breakfast and then make their way to the apartment building. At the same time, Lester was doing his best to make himself and the apartment presentable to his potential roommate.

At a quarter past 10 am, Sarah and Dan pulled their Dodge Journey into the parking lot of the Cityfront Tower apartment building. Sarah leaned over and grasped her husband’s hand. “This place looks great, babe! Can you see yourself living here?”

“Yeah, I guess,” Dan replied, looking through the windshield at the tower in front of him. The tower might have been an exaggeration. The apartment building in front of them was only twelve stories tall and looked similar to the half dozen other apartment buildings they had visited this weekend. It definitely wasn’t Trump Tower, but it wasn’t a shithole either. “I just hope the actual apartment is better than the others you dragged me to.”

Sarah feigned an annoyed expression. “I almost can’t wait to be rid of you.” She flashed Dan a quick smile. “Come on, it’s almost 10:30. Let’s go check this place out.”

They exited their vehicle and made their way through the parking lot toward a narrow pathway that led up to the lobby. As they opened the glass lobby door, Sarah retrieved her cell phone from her purse and quickly located the email from the previous night. Satisfied that she remembered the correct room number, she pressed #609 on the intercom.

After a few rings, a gruff voice emanated from the intercom’s speaker. “Hello?”

“Hi, this is Sarah Williams. We exchanged a few emails last night about renting out a room.” Without a reply, a buzzer went off followed by the click of the lobby door allowing them entry. As they rode the elevator up to the sixth floor, Dan began thinking about the brief exchange over the intercom. “So what do we really know about this guy?”

“Nothing really, I guess,” Sarah said, while watching the ascending numbers on the elevator’s screen. “What I do know is that you start work next week and need a place to live. This building is in a prime location and the pictures online made it seem worth our time. Plus, the rent fits in our budget.”

When the elevator doors opened, Dan moved to step out but Sarah gently grabbed his arm. Looking back at her, Sarah raised both her hands to cup his face and stepped closer to look into his eyes.” I love you.”

“I love you too, babe,” he said as he leaned in and kissed her.

After a few moments of holding up the elevator for their tender embrace, the couple made their way down the hallway to apartment #609 and knocked on the door.

Peering through the peephole, Lester took in the beauty of Sarah Williams for the first of many times. While the peephole only exhibited her angelic face, it was enough to cause Lester to adjust the rising bulge forming in his pants. Wanting to get a look at the rest of this woman’s body, he quickly opened the door.

When the door swung open, the Williams were greeted by a short, overweight man a few years older than Dan. Despite his unattractive features, it was clear he was trying to make an effort to look respectable. His wiry hair was being kept down with some kind of product, and he was sporting a blue dress shirt a few sizes too big, tucked into a pair of black slacks. Lester’s outward appearance helped set the couple’s minds at ease. While he was nothing special to look at, he at least seemed like a somewhat well-put-together individual. The potential roommates that they’d met over the previous few days had done little to impress them.

Dressing well upon first meeting a roommate was a tactic Lester had adopted over time. Portraying an upstanding member of society was Lester’s strategy to gain a bit of trust with potential roommates. No one wants to live with a stranger, let alone one who’s a dirtbag. The respectable appearance was just one strand of the web he was weaving to ensnare the couple.

While the couple’s first impression of Lester was being cemented in their minds, he quickly looked over the body of Sarah Williams. While his eyes danced up her body, he groaned internally. Yessss...

The woman standing in front of him was the picture of perfection. It took all of Lester’s mental fortitude not to emit that groan out loud. Her calf-length jean khakis hugged her slender thighs and shapely hips. A loose black blouse hung off her shoulders but did little to conceal the outline of the firm breasts hidden beneath. While he fantasized about what her body would look like without clothes on, Lester extended his hand. I’ll know soon enough. “Hi, I’m Lester.”

“Sarah,” she reached forward and shook his hand, noting some slight perspiration in his palm. “And this is my husband, Dan.”

Making physical contact with Sarah’s creamy vanilla skin caused Lester’s dick to swell even harder. While shaking her hand, Lester briefly broke eye contact to admire the slight jiggling effect their handshake was having on her chest.

From his past experiences as a lecherous roommate, Lester knew not to give Sarah too much attention. If he did, she may come to see him as his last roommate did – creepy. He released her hand and shifted his gaze to Dan, shaking his hand next. “So, you’re the one looking for a place then?”

“That I am,” Dan responded.

“Please come in and take a look around.” Lester stepped aside and motioned for the couple to make their way into his lair. The couple walked through the entryway and into the living room of the apartment. They took a brief moment to look around at the state of their new surroundings. A moment was all Lester needed to take advantage of the couple’s backs being turned to him as he admired the curvaceous behind of Mrs. Williams. Her perfectly round ass stared back at him as he licked his lips. Even though the material of the khakis was stretched to contain her excellent butt, Lester didn’t notice any underwear lines. She must be wearing a thong ... or going without. That naughty girl.

Sarah was relieved to see that the pictures posted online matched the apartment’s appearance. Everything appeared to be neat and tidy. The minimal furniture of the living room was neatly arranged around the TV without any dirty dishes or clothes strewn about. She was impressed that there was actually a centerpiece on the coffee table, as well as photos and candles neatly decorating the walls and shelves. This is much nicer than the last few places we looked at.

Dan gave Sarah a relieved glance. His apprehension about visiting this apartment from craigslist was slowly disappearing.

What the Williams couple didn’t know was that the tidiness and immaculate styling of the apartment were due to Lester’s last roommate. She had taken it upon herself to decorate and make the place more comfortable while she lived there. In her eagerness to move out and get away from Lester, she left many possessions behind.

“Feel free to take a look around and talk to each other. I’ll be here if you have any questions.” Lester forced the words out. He knew he had to seem outgoing and normal to make the Williams comfortable with him. He pointed across the living room to another doorway.

“Over there is the kitchen. It has fairly new appliances.” Motioning to the other side of the living room, Lester pointed Dan and Sarah in the direction of a hallway. “Down there on the left is the bathroom. The first door on the right would be your room and the one at the end of the hall is mine.”

After the brief exchange with Lester, the couple started checking out the apartment’s other rooms. Each room they visited was just as spotless as the living room. Even the fridge and medicine cabinet were neatly organized.

Standing in what could be his future bedroom, Dan was very happy with the size of it. “What do you think?” Sarah asked with a tentative smile.

“I think this place is the best one we’ve seen all weekend. It’s pretty tidy. I won’t feel like I’m slumming it here,” Dan walked over and opened the closet doors. Both doors opened to reveal a closet devoid of any clothing but with plenty of hangers and hooks for most of Dan’s wardrobe. “And this room isn’t half bad. It sure doesn’t beat our room at home, but it will do for now.”

“What do you think about Lester?” Sarah asked.

“He doesn’t seem like a bad guy. Definitely better than some of the other candidates we’ve met. I think he might be a little weird, but at least he keeps the place clean. What do you think?

“He seems nice.” Sarah thought back to meeting Lester a few minutes ago and the way he subtly looked her over. Just because he checked you out doesn’t mean he is a bad guy. He is a man, after all.

Sarah glanced at the full-length mirror on the wall, admiring her reflection. And I’m not too hard on the eyes. Can I really blame the guy?

“And yeah, the place is well kept.” She shrugged. “Not as well kept as our house, but I’m sure living with him will be bearable.”

Dan nodded and continued looking around the room.

“So ... what should we do? Do you want to take it or look around at some other places?” asked Sarah.

Dan turned to look at his beautiful wife. Her lovely green eyes showed nothing but love for him. Part of him still didn’t want to commit to renting any place because it would mean leaving her. He sighed. “Well, work starts next week and I’m still going to need some time to move some of my things in. I’m not sure we have time to look at other places. Besides, this is just temporary so I don’t need to live in the lap of luxury.”

He strode over to her and took her hands in his. “Let’s go talk to Lester.”

Two days later, Sarah and Dan returned to CityPlace towers with the Dodge Journey full of items for the apartment. After a few trips up the elevator, their vehicle was empty and the couple began unboxing things and setting up Dan’s new room.

Dan spent half an hour assembling an IKEA desk, while Sarah arranged pictures of their family around the room.

Having exchanged phone numbers when the Williams signed the lease, Lester sent Dan a text message apologizing for not being able to help him move because he had to work. In reality, Lester had taken the day off work and was watching the couple move Dan in through the peephole in his bedroom wall. Lester admired Sarah’s womanly form as she bent over to grab picture frames from the bottom of a box.

The clothing Lester wore when he first met his new prize was scattered on his floor. He was now wearing nothing but his unwashed, yellow-tinged t-shirt as he gaped through the hole at his new roommate’s wife. He rested his body weight against the wall using his left arm and was slowly stroking himself while Sarah moved around the other room in her sweatpants and hoodie. Ahh, fuck, she is just a few feet from me!

Lester furiously jerked himself off as he memorized every inch of Sarah’s body. Whenever she would talk to her husband he pictured her talking to him and his dick. He wanted nothing more than to walk into the other room and grab her by the ponytail and force her onto the bed. As she finished hanging the last picture, Sarah said “It’s getting really hot in here”.

With the two of them in one small enclosed room moving things around, the temperature was beginning to rise. Lester watched in amazement as Sarah began unzipping her hoodie. He began stroking faster as she tossed it aside to reveal a small tank top that showed off the tops of her juicy breasts. Lester grinned, his eyes glued to the naked flesh of her chest.

His eyes felt like they were bulging out of his head when she crouched to retrieve bed sheets from another box. As she sorted through the sheets, the angle of her chest gave Lester an unobstructed view down the top of her tank top. He furiously pumped his dick in his hand as Sarah’s breasts jiggled to match the movement of her arms. Fuck yeah, baby.

“Are we almost done, Dan? I just need to put these sheets on your bed,” Sarah stood up while opening a folded-up bed sheet.

“Yeah, the desk is all built and it looks like everything is set up,” Dan said, looking around the room. He neglected to notice the small peephole in the wall which was allowing a pervert to ogle his wife’s assets. “Once you’re done with the bed we can head back to the house and let your parents go home.”

Dan rose to his feet. “I’m just going to use the bathroom before we leave.”

“Ok, I’ll be done in two seconds and then we can hit the road.” Sarah leaned over to tuck the bed sheet into the far side of Dan’s double bed.

As Sarah bent over and forcibly began tucking in the sheet, Lester’s hungry eyes ran up her body, trying to decide what to focus on as he was getting close to finishing. Not a single bit of extra fat was on her.

Lester’s breathing became rapid as he continued shifting his eyes across her body. He wanted to cum looking at her angelic face, but his attention was diverted to the movement of her heaving, beautiful breasts as she tucked in the sheet. His eyes trailed down to her flat stomach and onto her fantastic ass, which was on display for him. I wish you didn’t have those clothes on.

With the bed completely tucked in, Sarah sneakily made her way across the room to her purse and reached for an envelope from it. Lester watched as she took the envelope and stuck it in one of Dan’s dresser drawers. What are you up to?

While Lester was still pondering what could be in the envelope, she picked up her hoodie and stepped in front of the mirror, looking herself over. To Sarah, she was looking at her reflection, but she was unaware that the mirror was almost in line with the peephole. From Lester’s side of the wall, it looked like Sarah was standing there just for him.

Having her this close and looking right at him sent Lester over the edge. He continued to pump his dick as he ejaculated onto a well-stained spot on the wall “Argghhh!”

Lester was so caught up in pleasuring himself that he didn’t care if he got caught peeping.

Lucky for Lester, Dan chose that exact moment to flush the toilet, drowning out the sounds of the older man’s ecstasy.

Dan exited the bathroom and made his way back over to his wife. Wrapping his arms around her from behind he looked at her through the mirror. “God, you’re beautiful. I’m really going to hate living here without you.”

She turned to face him while giving Lester a close-up view of her ass.

“It’s only for a little while,” she smiled with her eyes becoming watery. “And I will definitely be coming to visit you as often as I can.”

Lester’s ears perked up at those words. I look forward to it.

After a brief embrace, Sarah visited the washroom and the couple departed the apartment to head back to their family.

Waiting a few minutes to make sure they were gone, Lester left his den of iniquity and quietly entered Dan’s room. He made his way over to the dresser and retrieved the envelope Sarah had discreetly hidden. The words ‘For your eyes only’ were written on it.

He opened it and a shit-eating grin spread across his lips. Why Sarah, you shouldn’t have.

The envelope contained a love letter from Sarah to Dan. It expressed how much she would miss him and that he would always be in her thoughts. The note also described how much she loved him and would miss feeling his body next to hers. To keep Dan from missing her too much she included several boudoir pictures of herself to keep him occupied on lonely nights. For my pleasure now.

Lester took the photos out of the envelope and looked them over. Sarah was posing for the camera in several states of undress. These intimate pictures were meant for only her husband’s eyes, but now a deceptive stranger was looking at the most private parts of the young mother. As he shuffled through the photos, Lester felt his dick get hard again.

Without taking his eyes off the supple breasts of Mrs. Williams, Lester made his way back to his room.

Dan moved in a few days later and started his new job. He talked to Sarah and his kids every night on the phone and sent them plenty of text messages throughout the day. Aside from the occasional small talk, Lester and Dan rarely interacted. The only time that Dan would see Lester out of his room was when he would use the washroom or to heat up his dinner.

Over the course of their few interactions, Dan began to see Lester as a little odd and much different than how he portrayed himself during their first meeting. He didn’t mind Lester’s odd behavior, though, because it meant he was free to enjoy the apartment to himself.

Sitting down on the couch in the living room, Dan dialed his home number for his nightly phone call.

“Hey baby, how are you doing?” Sarah asked excitedly into the phone.

“I’m good, hun.” Dan was beaming. He always loved to hear his wife’s voice. “Work was good today, just the same old workload. I did try a new Chinese restaurant for lunch that I think you would like. Whenever you come to visit we’ll go out to dinner there.”

“Speaking of...” Sarah looked around to see whether her kids were within earshot. “I think I’ll be able to come to visit next weekend. My mom invited the kids for a sleepover Friday night. I’m sure she wouldn’t mind taking them for an extra day or two.”

“That sounds like a dream come true, babe.” Dan was ecstatic. Even though he had only been gone for a few weeks, he desperately missed the touch of his wife. “I can’t wait to get you up here. I have some non-PG things planned.”

“Oooh, I like the sound of that. I hope you have a whole itinerary planned out, Mr. Chicago.” Sarah twirled the phone cord on her finger, fantasizing about the upcoming weekend with her husband.