Roulette Round 02

Ashley Winters - 22, blond, and fit - lays on top of her bed wearing a t-shirt and pair of silk pink bikini panties on a hot and non air-conditioned Saturday morning. In a half-conscious state she rolls onto her belly on the cooler side of the mattress; the side that's against the wall.

As Ashley lays next to the wall noises emanating from her roommate's bedroom bring her into a more conscious state. As she lays there she shakes her head, "What in the hell Jamie? What the fuck are you doing making your bed this early on a Saturday?" Ashley glances over at her clock radio and sighs, "It's eight AM!" Ashley sighs as she lays with her face in a pillow, but the noises persist. After a few more seconds Ashley angrily exclaims, "What the fuck!"

Finally, Ashley puts her ear to the wall and listens. What she hears sends shockwaves through her body. She swallows hard as she pulls her head from the wall, "Oh my God!"

Ashley takes a deep breath then puts her ear back to the wall and listens a second time to confirm her suspicions. She hears her roommate, Jamie, panting, "Oh! Oh! Oh!" It's clear and apparent to Ashley, or anyone else for that matter, that Jamie is having sex.

Now fully awake, Ashley pulls back from the wall and exclaims, "Jamie! You little slut! You said you were going to the Bay View to have a nightcap with Lisa!" She rolls her eyes, "You obviously went back to the Yukon to hook up with the guy at the bar instead."

After a moment Ashley giggles, "I wanna listen!"

Ashley puts her ear back to the wall and hears Jamie pant, "Oh fuck! Oh fuck!" in unison to the guy's grunts and bed thumps. Listening to her roommate's naughty and intimate moment with a guy she picked up at a dive bar instantly gets Ashley's pussy wet.

Ashley listens and thoughts of what it would have been like for her to hook up with the guy at the end of the bar instead of Jamie fill her head. Ashley's heart races and the flood gates to her pussy are now wide open. The more Ashley listens, the wetter her pussy gets. Her hand quickly slips inside her snug pink panties and finds her clit. Ashley pants softly as she rubs her clit with her ear firmly against the wall, listening to Jamie fuck.

As Ashley is about the let a finger slip inside her slippery pussy the noises from next-door stop. She gasps, "What?" Ashley listens intently trying to figure out why the sex stopped.

After a few seconds, she hears Jamie ask, "It's still on, right?"

The guy answers back, "Yeah."

"Make certain it's on really good. This is NOT a good time for it to come off or break."

"Don't worry it's on good."

"It won't be good if I get knocked up."

Knowing that she and Jamie's periods are synched Ashley gasps, "Oh my God! She's totally fertile!" She then giggles like a schoolgirl, "I hope it breaks!"

Jamie is heard panting on the other side of the wall again, "Oh fuck! Oh fuck!"

Ashley rubs her clit faster, biting her lip then panting quietly to herself, "Common, break it! Break it!" As the bed thumping from next-door gets faster and the panting gets louder Ashley's fingers press harder.

Jamie begins moaning, "Oh yes! That feels so fucking good!"

"Oh yeah!" The guy grunts back as the bed thumps.

Ashley pants back softly, "Give her a creampie!" Ashley's fingers move faster on her clit, "Make her pay for being such a slut."

Jamie moans, "Oh! Oh!"

Ashley pants, "She needs one."

The guy can be heard moaning out, "Oh Fuck! Oh fuck!"

"Do it!" Ashley pants as a finger slips inside her pussy.

Jamie gasps, "Yes!"

The guy moans, "OH!" As the bed thumps one final time.

For several seconds there's silence. Then finally Jamie is heard, "Is it still on?"

"Yes."

"Good!"

Ashley shakes her head, "Damn it! No creampie."

Frustrated she didn't cum Ashley gets off of the bed and walks over to the bottom drawer of her dresser. She rummages through the drawer and finds her squirting dildo only to see that it is out of fake cum.

Ashley shakes her head, "Really?" She could use water but it's not nearly as fun. The fake cum even leaves white stains in the crotch of her panties just like the real stuff does.

Still horny, Ashley reaches back inside her panties and inserts her index finger inside her pussy. She pushes it in deep, rubs for a couple of seconds then pulls it back out. She then pulls her fingers out of her pussy/panties and presses her finger and thumb together then slowly pulls them apart. As she does her juices create a string between them, the same consistency as egg whites. Ashley has the telltale signs of a girl who's ovulating.

Not that she'd be fucking Barry, her most recent boyfriend, this weekend if they were still together. After playing preg roulette down at the Whisper Bay Inn with Devin last summer, Ashley made it a point to not fuck when she's ovulating. It's simply too easy to get carried away.

But listening to Jamie fuck and knowing that Jamie fucked while she's ovulating has gotten Ashley's juices flowing, just like the night at the Whisper Bay Inn. The night Devin got her to play that kinky game and fucked her in the backseat of the car parked in his garage.

Ashley swallows then pants hard as she contemplates contacting Devin. In her current state that would be SO bad. But, it might feel SO good, just like last time.

Ashley stands in her room conflicted, wanting to call or text Devin, but knowing she shouldn't. There is only one to settle this. She'll pull the first coin out of her purse. If it's an odd year she'll him a text, if it's an even year she'll just use the dildo.

Ashley grabs her purse reaches inside and pulls out a quarter. "Here goes nothing!" She anxiously looks at the year: 2015. Seeing the odd year gets Ashley's pussy even wetter. Ashley takes a deep breath and mumbles to herself, "He's probably not up or busy. Besides, that was over a year ago, he probably won't even remember me."

Ashley walks back to her bed and pulls her phone off of the nightstand and finds the Whisper Bay Inn's Facebook page. On it is the phone number, the number Devin said she could call or text any time.

Ashley takes a deep breath and types in her phone, "Hi! This is Ashley, we played roulette last summer. I just thought I'd say hello." She then anxiously sends the message.

Ashley then hops back on her bed and starts thinking about how she got to be the 80's girl when she played preg roulette with Devin. She thinks about how short her blue and white nylon shorts were, about how it felt to wear the goofy white top with shoulder pads and how she looked with big hair.

When she thinks about what was like to be under lights in her tight shorts about find out if she was going to get an ill-timed creampie her hands move back inside her panties. She rubs her clit thinking about how nervous she was when she opened the envelope. She rubs her clit when she thinks about how she was both relieved and yet disappointed when she saw the condom in the envelope.

Then she thinks about what it would have been like to be in the back seat of the car, with her shorts and panties pulled down to her ankles with her legs spread wide apart with Devin fucking her bareback. It would have been so fucking hot to have been the slutty eighties girl having Devin promise to pull out, but not. Being the eighties girl who got a creampie surprise at the worst possible time.

"Oh!" Ashley pants as she fingers herself.

Ashley slides a finger inside her pussy gasping thinking about what the 80's girl could have said. Maybe something like Jamie said. Maybe, "This is NOT the time to cum inside me." Ashley moves her finger deeper inside her as she whispers quietly in worried way, "You have to pull out!"

Getting closer to orgasm Ashely hears a text ring into her cellphone. She stops fingering herself then nervously pulls her phone off of the nightstand. When she sees the text her heart pounds: it's from Devin.

Ashley anxiously opens the text, "Hi Ashley! How have you been?"

Ashely types back, "Good, you?"

Another response comes back, "I'm good I was wondering when you were going to come back and play roulette."

Ashley's heart races knowing how hot the sex was when she played last time. She nervously replies back, "lol I thought you had forgotten all about that."

Ashley takes a few seconds to contemplate her response, then the phone rings it's Devin! Ashley takes a deep breath then answers, "Hey there."

"Hey! How have you been?"

Hearing Devin's voice again makes Ashley's heart beat faster, "I've been good."

"So, didn't you like playing Roulette?"

"It was alright."

"Just alright?"

Ashley smiles, "Okay, it was kind of hot."

"Then you should play again."

"Think so, do you?"

"Yeah I do. There are some new clothes in the closet."

Ashley's intrigued, "Really?"

"Yeah. I'm sure they would look really good on you."

"I don't know about that."

"Why don't you come on down?"

"When?"

"Right now."

Ashley's heart races faster, "I don't know, I'm kind of busy this morning."

"Are you busy or ovulating?"

Ashley blushes, "Devin!"

"You are, aren't you?"

Ashley lies, "No."

"If you are, you can come own and play roulette."

Ashley is flustered, "I'm not, so I guess we can't play."

"Well I'm going to be here all morning if you are looking to play roulette or any other sexy game."

"Well, I'll keep that in consideration."

"Good, I hope you take me up on it."

"I'll think about it."

"Just ring the doorbell and I'll buzz you in."

"Alright, bye."

The call ends and Ashley contemplates her options for a moment. She knows she shouldn't go see Devin because it will probably lead to sex, maybe even unprotected sex. But this fact just turns her on more. What's more, the last time she went down there she had some of the hottest sex she's ever had.

Ashley takes a deep breath then walks over to her dresser and pulls out a pair of shorts, t-shirt and bra. She gets dressed, grabs her keys, cellphone and purse and heads out the door.

Ten minutes later Ashley walks up to the front door of the Whisper Bay Inn. She rings the doorbell and a few seconds later the buzzer sounds, the door unlocks and walks inside the weathered three story wood-framed structure.

Once inside the small lobby she is greeting by Devin Dixon - 34, handsome, dressed in shorts and polo - "Well hello, stranger."

Ashley smiles, "Hi."

"You look as good as ever."

"Thank you."

"In the mood for a little roulette?"

Excitement flows through Ashley's body, "I guess that depends on what's in the closet?"

Devin smiles, "There's one good way to find out and that's to take a look. Common!"

Devin leads Ashley back down the hall to the first door on right that is labeled, "Wardrobe." He unlocks the door and the two enter the large room that is filled with racks and racks of women's clothes.

The two walk back to the closet in the corner of the room. As they do, Ashley's heart races, her palms sweat and she feels moisture building between her legs as she knows the last time she saw this closet, she ended up having hot, intense sex.

Devin opens the closet door then turns to Ashley, "It looks like size four to eight should still fit you."

Ashley smiles nervously, "It should."

"Take a look and see if there is anything you want to try on."

Ashley grins slyly, "I don't know about that."

Ashley then begins looking at the clothes in the closet. The first two hangers are holdovers from last year the pair of white shorts with a white tank top and yellow button down sweater and the pair of faded jeans with studded chrome belt and pink pullover top.

Ashley moves to hanger three which is a brown polyester fast-food uniform from the eighties. "Where do you find such hideous stuff?"

Devin chuckles, "The internet."

"That figures." Ashley moves to hanger four and five two more holdovers from last year a pair of black leggings and red t-shirt from a pizzeria and blue corduroy jumper with grey sweater and tights. On hanger six a red cheer leader uniform. Ashley smirks, "Does the cheer uniform come with a bitchy attitude?"

"The bitchy attitude is optional."

Hanger seven the black pleated stirrup pants and goofy sweater from the 1990's which Ashley quickly passes by. On hanger eight is an overall yellow short set with short sleeve white top. Ashley pulls the hanger out, "What's this?"

"That would be a sweep uniform."

Ashley looks at Devin, "Sweep uniform?" She then looks back at overalls, "What's a sweep uniform?"

"A sweep works at resort and sweeps the grounds and public areas."

"Interesting." Ashley pulls the shorts apart, "There's not much to them."

Devin grins, "That's probably why they lead to sex."

"Imagine that."

"Your legs and butt would look good in it though."

Ashley grins as she puts the hanger back on the rack, "Maybe."

Hanger nine is the pair of burgundy spandex shorts and t-shirt. Ashley smirks as the moves to the next hanger, "I see the trailer park still hasn't collected their clothes."

"White trash girls need to have sex too."

"I guess." Hanger ten is a white denim mini shirt and floral button down shirt. Ashley pulls it out, "This almost works."

"Think so?"

Ashley grins, "Maybe." She takes a second harder look at them then puts them back on the rack. Hanger eleven is a pair of Christmas yoga pants and holiday sweater. "I see a pattern here, the more hideous the outfit, the longer it stays in the closet."

"Those pants could have led to the best sex ever."

Ashley looks at Devin, "No they didn't"

"If you say so."

"I know so." Ashley shakes her head as she moves to hanger twelve a white lacey short set and top. Ashley takes a look at the hanger for a moment then shakes her head, "Nah."

Finally Ashley moves to hanger fourteen the crushed velvet deep green dress. "This still isn't bad." Ashley pulls the dress out.

"Which one is it going to be?"

Ashley rolls her eyes then turns to Devin, "Who said I was going to play?"

"Your eyes."

Ashley feels moisture building between her legs. "I don't know about that."

"What are the finalists?"

Ashley pulls the crushed velvet dress out, the mini skirt with floral top and the yellow short overalls off of the rack. "All of these could be fun."

"Of course."

Ashley then pulls out the stirrup pants, "Retro was fun last time."

Devin grins, "Yes it was."

"I like the crushed velvet, but it really isn't a summer outfit." Ashley then places the miniskirt and the short overalls side by side and looks at them both. "The mini skirt is summery and fun." Ashley then puts the stirrup pants back in the closet, "The pants aren't very summer either."

"The overalls are totally summer"

"Yeah I guess."

"You could try them both them both on."

Ashley turns to Devin, "I didn't say I was going to play."

"I know you want to."

Ashley smiles slyly, "Maybe, maybe not."

"I know I have shoes for the overalls, let me see if I have any for the miniskirt. What hangers are they?"

"Eight and ten."

Devin walks over to one of the filing cabinets near the closet, opens a drawer and begins rummaging through it. He pulls out two large envelopes then walks over to the second, larger closet, "Will a size five shoe work?"

"Probably."

Devin pulls out a pair of Sketcher shoes then walks back over to Ashley.

"The Sketchers could probably work for the both the overalls and the miniskirt." Devin hands the envelopes and shoes to Ashley. "You know the rules."

"I think I remember." Ashley smiles smartly.

"You can try on either, but if you wear them back out here, you are committed. You have to act out what happened to the last girl who wore them."

"That is if, I decide to wear them out here."

"You will."

Ashley grins, "We'll see."

Ashley then walks out of the room and to the dressing room that's across the hall. After turning on the lights in the girl friendly room she closes and locks the door then walks up to the table containing beauty aids.

As she hangs the hangers on the hook on the wall, Ashley begins thinking about what happened after she left this room last year as she does her chest heaves. She then pulls her top up and off, then unbuttons her shorts and let's then drop to the floor.

After folding her top and shorts Ashley grabs the miniskirt and steps into and pulls it up. As she zips it up she notices the skirt is about a size too big for her. Ashley shakes her head, "it figures." Ashley then takes the floral blouse off of its hanger and puts it on.

Now dressed in the skirt and top, Ashley takes a look at herself in the full length side mirror and is unimpressed with the way the clothes fit on her. She smirks, "Good God! I look like I'm going to a middle school dance."

Ashley then opens the corresponding envelope that matches the miniskirt and pulls out a pair of white satin bikini panties and matching back clasping bra. She shakes her head, "Boring."

Next Ashley opens the envelope for the overalls. She pulls out a pair of pink cotton bikini panties that have Pac Man on them and a phrase above it stating, "Ghost me." Ashley giggles, "Cute!" She then pulls out yellow front clasping bra. Ashley then looks at the overalls, "Maybe they could be fun."

Ashley takes off the floral top and mini skirt and puts them back on the hanger. She then pulls her panties down and off and places them on the table and grabs the Pac Man panties and steps into them. She then pulls them up over her hips and butt and they snugly grip her body.

Ashley picks up the bra but quickly realizes that it won't fit her so she grabs the top and puts it on. After she pulls her blond hair out of it and grabs the overalls as she does she notices the size four tag inside of them and feels a rush come over her. She then giggles, "I wonder if they'll be as tight as my old work pants."

Ashley then steps into the short overalls and pulls them up and pants when she feels how tight they are. Next she attaches both of the suspender loops to the bib pocket which keeps the shorts tight on her butt.

She then looks at herself in the full length mirror. She covers her mouth as she sees how her butt pokes out of the yellow shorts that are clinging to her tight body. "Wow!" Ashley bites her lip, then smirks, "I look like a total sex pot in these." Ashley giggles, "Maybe even a cum dump."

Ashley then takes a seat at the table and begins braiding her hair into one long braid then does her makeup. After she's done she stands up and takes another look at herself in the full length mirror, "I wonder if the sweep used a condom." Ashley bites her lip, "There's one good way to find out."

With that, Ashley walks out of the room wearing the tight yellow short overalls and white top.

A couple seconds later Ashley walks into Devin's office. He smiles, "Well look at you!"

Ashley grins then slaps her thighs, "Who would have thought they would look like this on me?"

"They look good! Real good!" Devin gets up, "Let's go play!"

Devin leads Ashley to the video room next door then turns to you, "You know where the mark is." Devin then walks into the small control booth.

"Yes I do." Ashley steps on the "X" that's on the floor made out of masking tape. As Devin turns on the studio lights Ashley becomes more and more turned on.

Once the lights are on Devin walks into the studio holding a microphone. He then begins speaking into the microphone as if he was a game show host, "Good evening everybody! Tonight we are back with everyone's favorite game of chance, Preg Roulette! Tonight's female participant is Ashley. Ashley is a twenty-two year-old recent graduate of Seaside Community College and repeat participant in Preg Roulette. Ashley, say hello."

Ashley smiles, "Hello."

"As always, Ashley isn't on the pill, shot, diaphragm, etcetera! What's more Ashley is smack dab in the middle of her cycle." Devin grins, "Which would make getting a creampie a very risky proposition for her." Devin turns to Ashley, "Isn't that right?"