Roulette - Round 01

Ashley Winters -- 21, blond, and fit - walks out of a big box office supply store clutching the paper bag that contains a completed school project for one of her last classes before her graduation from Seaside Community College. As she's about to step foot into the parking lot she sees a familiar face walking towards the dollar store next-door.

Ashley yells towards the face, "Cassie! Cassie!"

The familiar face is Cassie Henry -- 21, brunette and six months pregnant. Cassie turns to Ashley, "Ash?"

Ashley attempts to hide her surprise at Cassie's noticeable baby bump as she walks over to her, "How have you been?"

"I'm good, how are you?"

"I'm good, just getting ready to graduate."

"Cool."

"I haven't seen you around school."

Cassie fidgets, "I quit school on the account of me getting ready to be a single mom."

"Really?" Ashley attempts to look surprised.

"Yeah."

"Well... congratulations."

"Thanks." Cassie fidgets momentarily, "And congratulations on your graduation."

"Thanks."

Cassie looks back at the parking lot, "I'd like to chat but my ride is kind of in a hurry."

"Gottcha."

"Message me on Facebook sometime."

"I will."

"Talk to you later."

"Talk to you later." Ashley walks to her car.

Once Ashley is inside her vehicle she exclaims, "Oh my God!" Ashley stares at the windshield in disbelief and mutters, "Could the rumors about the Whisper Bay Inn be true?"

Later that afternoon Ashley sits at her desk looking at the Facebook page for the Whisper Bay Inn, the rundown 19th century downtown hotel, turned into boarding house. The property stood vacant for several years after its long time owner, Old Man Pemperton, died. About a year ago Pemperton's family was finally able to sell the property to a new much more vigorous (younger) owner.

Not long after closing rumors about the new owner's propensity to play sex games in the building began to circulate through town. At a kegger after midterms, a girlfriend told Ashley that Cassie played a game called Preg Roulette down at the Whisper Bay Inn.

After seeing Cassie today Ashley's curiosity about the sex games and the Whisper Bay began burning. Fanning the fires of Ashley's curiosity is the fact that the Whisper Bay Inn's Facebook page is a closed group and has very little information about what the new owner is currently using the building for. Ashley sighs then sends a request to join the group.

About an hour later a chime rings in on Ashley's laptop. Ashley maximizes Facebook to learn that she has been accepted to the Whisper Bay Inn's private group. She takes a quick survey of the page and upon seeing, "Live out any fantasy at the Devil's Arcade down at the Whisper Bay Inn" Ashley's curiosity burns with a much hotter intensity.

Ashley looks at the page in stunned disbelief, "Oh my God!" After thinking for a moment she types in the messenger to the Whisper Bay Inn, "Greetings! A friend of mine told me you play games down there. She said one of these games is called Preg Roulette. This isn't true is it?" Ashley nervously sends the message then anxiously waits for an answer.

A few seconds later a response comes back, "Preg Roulette is one of the more intense games we play here. Are you interested in playing?"

Ashley gasps, "Holy shit!"

Another message comes onto the screen, "I'll be happy to arrange a time for you to play if you'd like."

It takes three attempts for Ashley to type a response, "I don't want to play, but was really curious about how the game is played. Are there rules?"

About a minute later a response comes back, "It's really a simple game. The rules are as follows: 1. You have to understand you will have sex when you play. 2. You have to be at least 18 to play. 3. You can play it with a boyfriend/male friend or myself or Todd. 4. You cannot be on birth control. 5. You have to either be in or about to enter the most fertile part of your cycle when you play. 6. You can select anything out of the roulette closet to try on. But if you wear the clothes back into the room you have reenact whatever happened to the girl who last wore the clothes. Please remember: once you wear it back into the room you are committed. There are no second chances or mulligans"

Ashley's heart pounds as she reads the rules. She shakes her head and mumbles to herself, "I can't believe it, the rumors are true."

Ashley's curiosity quickly transforms into excitement because creampies and/or risky sex is a huge turn-on for her. The only reason why she hasn't had more unprotected sex is that she promised her mother she wouldn't even consider getting pregnant until she graduated college.

Now that Ashleys's almost done with school makes the thought of having risky sex even a bigger turn on. One night at the Yukon Bar about a month ago Ashley probably would have risked it with the cute guy she was playing pool with. However, at the last moment, her friend Jamie swooped in and got her out of the bar before the two could even exchange numbers, much less hook up.

Another message comes in from the Whisper Bay Inn, "My name is Devin. If you want to play preg roulette or anything else sometime just message me or call the number on the page."

Ashley takes a deep breath then types, "Thanks Devin! I'll keep that in mind." After sending the response, Ashley closes out Facebook and returns to her studies.

A couple months later Ashley is at her fast-food job out by the mall. It's been a tumultuous summer for her as she has received her certificate from SCC, conducted a job search, accepted a position with a medical billing firm out by the industrial park and gave notice to the burger joint.

Today Ashley's working one of her last shifts, a Sunday lunch shift. Sunday lunch shifts are usually pretty tame and today is no exception. Seeing that business demands don't justify as many employees in the store that are currently working Ashley's manager walks up to her, "Miss Senioritis, do you want to go home early?"

Ashley grins, "You don't have to ask me twice."

"Give me a lobby check and you can get out of here."

"You got it!" Ashley walks over to the broom closet and pulls out a small broom, dustpan, rag and cleaning bottle and heads to the lobby.

A couple minutes later, as she cleans a booth, Ashley glances over her shoulder and notices a middle aged guy's eyes locked squarely on her ass. This is a common occurrence when she wears the size four work pants, the work pants that are a good size too small for her. Ashley makes certain to give the guy a good show and bends over as she "thoroughly" cleans the seat.

Ashley usually wears the sixes as they are much more comfortable and easier to work in but when she's feeling frisky or wants to give Ryan or one of the other new guys in the back the bends she wears the fours. The funny thing is this is she is normally in the middle of her cycle when she does this.

As Ashley pulls the trash out of the receptacle it dawns on her that she is totally in the middle of her cycle. This, of course, is something she normally keeps close tabs on. However, with all the changes in her life Ashley had not even thought about it until just now.

As Ashley takes the trash to the dumpster she thinks about the guy in the lobby. Would he fuck her if he was given the chance? If he did, would he be responsible and use a condom? It would probably be a crapshoot she thinks as she heaves the trash bag into the dumpster. Or just maybe, it would be more like roulette.

As Ashley closes the gate to the dumpster she starts thinking about the Whisper Bay Inn downtown. She's got the whole afternoon free now; she could go talk to that guy from Facebook about roulette. She couldn't, could she? As she walks back into the store she thinks how irresponsible it would be to do that. Not unlike that night playing pool, but only this time she wouldn't have Jamie to bail her out. But it would be fun, probably too much fun not to mention way too much temptation.

As Ashley walks back to clock out Katie, the drive-through girl, breaks her train of thought, "Have fun, Ash."

Ashley turns to Katie as she clocks out, "fun?"

"You're off almost three hours early; I have a feeling you'll find something fun to do."

Ashley grins, "I might go down to the waterfront, I'll see." Regardless I'll see you Tuesday."

"See you Tuesday."

A few minutes later Ashley is on her way to the waterfront. For whatever reason, she chose Bay Street to get there, the same street the Whisper Bay Inn is on. The closer Ashley gets to the Whisper Bay Inn, the faster her heart races.

By the time the weathered three-story wood-framed structure comes into view Ashley's palms are sweating. She slows down as she drives by the 19th century structure enough to not only find an open street parking spot but be able to park her car in it.

Ashley puts her car in park and takes a long hard at the Whisper Bay Inn and thinks about all the hot sex that must take place behind those battered walls. Maybe even, all the unprotected sex that happens there.

Ashley swallows hard as she thinks about the roulette closet. All those clothes waiting for some unsuspecting girl to make a choice, a choice that could very well result in her getting knocked up. As Ashley contemplates what it would be like to make "the wrong choice" she feels heat and moisture build in her work pants.

Ashley leans over the seat and takes a second harder look at the Whisper Bay Inn. The more she looks at the building, the more she wants to actually see the roulette closet or more importantly the clothes that are in it. This is so risky. But, she just wants to see a few clothes.

Ashley begins justifying thoughts, "You could just ask to see the closet. What could that hurt?" Ashley leans back one more time looking at the old hotel. "If it gets creepy, just leave."

Ashley shuts the car off and exits the vehicle and quickly walks up to the front door of the Whisper Bay Inn. At the front door of the building Ashley takes a look over her shoulder to make certain no one sees her. Satisfied no one has she nervously rings the doorbell and fidgets as she waits. As she waits, Ashley begins rethinking her decision. Maybe this isn't the best idea, maybe she should get back in her car and just go home.

As Ashley contemplates leaving she is startled by the buzzer that unlocks the door. Ashley takes a deep breath then opens the door and timidly walks inside the building.

Inside is a small lobby, to the left are stairs leading up and down, on the right is a hallway that leads back into the first floor and in the center is a small front desk. Standing at the desk is Devin Dixon -- 34, fit, charismatic and good looking -- who greets Ashley, "Hello! How may I help you?"

Ashley timidly approaches the desk, "Yeah I was wondering if I could speak with Devin?"

Devin flashes a killer smile, "I'm Devin."

"Oh, hi. I'm Ashley I think we talked on Facebook a while back."

Devin stops to think for a moment, "Oh Yeah! You're interested in playing preg roulette."

Butterflies flutter in Ashley's stomach, "Well I didn't actually want to play. I was more curious as to what is actually in the closet."

"So you want to see the closet?"

Ashley's eyes light up, "Could I?"

"If you got I. D. you can."

"Sure." Ashley pulls her driver's license out of her purse and hands it to Devin.

Devin looks at the I.D. momentarily then hands it back to Ashley, "You're familiar with the rules right?"

"I don't want to play. I kind of want to just see the closet."

"Of course." Devein smiles, "Got an app?"

"App?"

"You know a period tracker?"

Ashley blushes, "Yeah but."

"But?"

"Like I said, I don't want to play."

"But you want to see the closet, right?"

"Yeah."

"Then I need to see the app."

Ashley pulls her cellphone out of her back pocket, "I would never in a million years show a guy this."

"Of course not." Devin grins devilishly, "That's what makes it so much fun."

Ashley opens an app on her phone and hands it to Devin and shakes her head, "Most people want to come out of the closet I want to get in one. Go figure."

"To each their own." Devin takes a look at the screen of the cellphone then hands it back to Ashley.

"No pill, shot, IUD or DUI?

Ashley giggles, "No. DUI, now that's a form of birth control I want to no part of."

"Nor does your auto insurance company. Follow me."

Devin leads Ashley down the hall to the first door on the right which is labeled, "Wardrobe." He opens the door and the two walk inside.

Ashley is astounded by the racks and racks of women's clothes that line the large room, "Wow!"

As Devin leads Ashley to the back corner of the room her heart races, her palms sweat and heat builds in her pants. She isn't even paying attention when Devin turns to her, "Ready to see?"

"See? Yeah, of course!"

Devin opens the door to the closet full of women's clothes. He points to the center section, "Anything in the middle is size four to eight which looks like should fit you."

"Cool."

Devin grins, "Take a look and see if there is anything you like."

Ashley cautiously approaches the closet and begins looking at the clothes. On the first hanger is pair of white shorts, a white tank top and yellow button down sweater. Ashley looks at it momentarily then moves to the next hanger which has a pair of faded jeans with studded chrome belt and pink pullover top.

"There is a dressing room across the hall if you see anything you want to try on."

Ashley smiles politely as moves to hanger three, "I'll keep that in mind."

On hanger three is a brown dress with a floral pattern on it. Ashley turns to Devin, "I don't see anything that's very risqué. I thought roulette was a game of risk."

"It's not so much a game or risk as it is a game of chance."

"Why do you say that?" Ashley moves to hanger four, a pair of black leggings and red t-shirt from a pizzeria.

"The whole idea about roulette is leaving your fate up to chance."

Hanger number five has a navy blue corduroy jumper with grey sweater and tights. "You think so?"

"In Russian roulette, you leave it up to chance as to what round the chamber is in."

Ashley looks at Devin oddly, "Round?"

"Round, where the bullet is."

"Oh." Ashley moves on to hanger six a red terrycloth romper short set from the 1970's.

"The only way to find out where the bullet in Russian roulette is to pull the trigger." Devin grins, "The same is true in this hybrid of the game."

Next is hanger seven a pair of black pleated stirrup pants and goofy sweater from the 1990's. Ashley looks at the sweater and chuckles, "Wanna effective form of birth control, try wearing this sweater."

"They did things differently back then."

"Thank God they're different now." Ashley moves to hanger eight a pair of blue and white four panel Dolfin Shorts and white short sleeve top with shoulder pads from the 1980's. "Oh my God!" Ashley pulls the hanger out.

"Like those?"

"I've seen these in movies."

"Apparently they were big in the day."

"One thing's for certain, these shorts aren't very big!"

Devin grins, "I could see your butt poking out of those."

Ashley blushes, "I couldn't. I mean they're ridiculous."

"Of course they are. That's another thing that makes the game so much fun."

Ashley looks at Devin oddly.

"You get to be someone else when you play. Instead of being Ashley, fast-food girl, you can be Rochelle, the fun girl from the eighties."

"I'm fun!"

"I didn't say you weren't. I'm just saying you could be Rochelle, who probably had a really fun time after wearing those shorts."

"Good for Rochelle."

"Maybe you would too."

Ashley contemplates the thought of being an eighties girl for a moment. For some reason though sends excitement though her body. Thinking better of it, she puts the hanger back on the rack, "Maybe, maybe not."

Next up on hanger nine are a pair of burgundy spandex shorts and t-shirt. Ashley smirks as the moves to the next hanger, "The trailer park called and wants their clothes back."

Devin chuckles at the trailer park comment.

Hanger ten is a pair of camo yoga pants and halter top. Hanger eleven is a pair of Christmas yoga pants and holiday sweater. "Oh my God! I was wrong, there actually is a more effective form of birth control that that last sweater."

"Again, to each their own."

Ashley shakes her head as she moves to hanger twelve a mauve bridesmaid's dress. On thirteen is a black skirt and a white button-down blouse. Ashley smirks, "Boring." Finally she moves to hanger fourteen a crushed velvet deep green dress and pulls it from the rack to have a better look at it.

"Like that one?"

"It almost looks fun."

Devin grins, "Probably not as much fun as the Dolfin shorts."

Ashley looks at Devin oddly, "Dolfin shorts?"

"The eighties shorts."

"Oh." Ashley puts the crushed velvet dress back on the rack.

"Wanna try something on?"

Ashley smiles politely, "I'm just kind of window shopping."

"Just because you try it on doesn't mean you have to take it home." Devin grins, "Unless of course you wear it back in here."

"If I do that the stakes get significantly higher."

"Yeah, but the fun gets significantly better."

"Think so do you?"

"I do." Devin reaches into the rack and pulls out the Dolfin shorts and white top.

Ashley swallows then watches nervously as Devin takes the shorts off of the hanger.

"I can tell you like them." Devin holds the shorts up against Ashley's waist.

Ashley breaths a little deeper, "They're alright."

"You know, girls did have sex in the eighties."

"I'm sure they did."

"Some of them undoubtedly were wearing shorts just like this before they did." Devin grins, "These look like they would just about fit you too."

Ashley swallows again, "Um, maybe."

"Don't you think it would be fun?"

"Fun?"

"To try them on."

The fact that Devin's exploiting the fact she kind of likes the shorts begins to arouse Ashley, "Look, I couldn't possibly wear those out here or anywhere else for that matter."

"I didn't say you had to. But if you wore them out here you would have to play." Devin puts the shorts back on the hanger.

"How do I know you didn't stack the deck on me?"

"It's kind of hard to stack the deck when I don't know what your point of view is."

"What do you mean?"

"I don't know what you fear. What turns you on. Maybe unprotected sex is a huge turn-on for you. Maybe getting pregnant is a morbid fear. I really don't know, and because of that it's hard for me to rig the game. For all I know, maybe you want to get knocked up."

"I'm only 21."

"That doesn't mean anything. There are plenty of 21-year-old girls and younger who want to have a baby. I will tell you this, more one set of clothes lead to unprotected sex and more than one set led to protected sex."

"For the record, I don't want to get pregnant."

Devin looks deep into Ashley's eyes, "Maybe the girl who wore them last didn't, maybe she did. Perhaps her desires and fears had nothing to do with the outcome. Like the pistol you don't find out where the round is until you pull the trigger."

Ashley sighs, "I just..."

"Got try them on, you don't have to wear them out here." Devin points to the other side of the room, "Or pick out something from over there and act out whatever fantasy is up in that pretty head of yours." Devin hands Ashley the hanger.

Ashley feels the lightweight silky texture of the material and finds herself becoming more aroused. She takes a hard final look at the shorts and blouse then turns to Devin, "Okay, I'll try them on but I'm not wearing them back out here. I'm... NOT playing."

"That's up to you." Devin walks over to a filing cabinet. "What's the number on the hanger?"

Ashley looks at the hanger, "Seven."