Roulette - Round 01

Devin opens a drawer on the cabinet and pulls out a large envelope. He opens it and pulls out a lavender satin bikini panties/bra set, envelope and photo. He walks back over to Ashley and hands them to her. "Hopefully these will fit."

Ashley looks at the photo and sees a blond teenage girl, with big eighties-style hair dressed in the shorts and top. "Who's the girl?"

"The former owner of the shorts and top, Rochelle. What size shoe do you wear?"

"Six."

Devin rummages through a plastic bag and finds a pair of sandals. "These look like they should fit." Devin hands the sandals to Ashley. "Across the room is a dressing room where you can get changed. There are brushes, moose and anything else you may need for your hair. I'm sure you can find a how-to video on Youtube on how to do your hair like Rochelle's."

"Okay."

"I'll be in the office next door, so if you want to play come in wearing them or you can try on something else if you want."

Ashley doesn't say anything and exits the room and walks across the hall to the dressing room. Once safely inside she closes and locks the door and leans against it almost panting, "Oh my God!" She takes a deep breath, "I can't believe I'm even thinking about doing this. Oh God!"

Ashley takes a couple of seconds to regain her composure then takes stock of the very girl-friendly room which has a seat in front of a table filled with beauty products. Behind the table is a large mirror with light bar. Ashley flips on a switch and the lights turn on. "Nice!"

Ashley hangs the shorts and top on the hanger on the wall then places her purse, and the panties, bra sandals, photo and envelope that Devin gave her on the table. She then takes off her work polo and work pants, folds both and places them on the table. She pulls down her red silk bikini panties that have a wet spot in the crotch, folds them and places them on the table.

Ashley grabs the lavender panties, steps into them and pulls them up her legs and over her hips and butt. She then takes a look at the matching bra, "I could probably make that work." Ashley makes a couple adjustments to the back clasping bra, then takes hers off and puts the lavender one on. "How about that? It almost fits"

Ashley reaches over and pulls the shorts off of the hanger then steps into them. She pulls them up; it quickly becomes apparent to her as she pulls them up over her butt and hips that the shorts are even shorter and tighter than she anticipated.

Next is the top, Ashley grabs it and pulls it off of the hanger and puts it on then pulls her hair out of it. The first thing Ashley notices about the top is it barely covers her navel much less offer any coverage for her butt or waist.

She then turns sideways and looks at herself in the full length mirror mounted on the wall. She giggles, "My butt really does pop out of these shorts!" She grins as she turns again, "They are nice and tight and super comfy, who would have thought?" Ashley turns and takes a look at her other side. "I can see how Rochelle got laid wearing these."

Ashley takes a seat at the table, picks up a brush and runs it through her hair a couple times. She grabs her cellphone, opens Youtube and does a search for how to do her hair eighties style. After about twenty-five minutes of trial and error Ashley gets her hair to look almost like the girl in the picture: eighties big and parted down the middle.

Ashley then opens the envelope, inside are a set of white plastic earrings and set of white plastic beads for a necklace. After the earrings and necklace are on she puts the sandals then stands up and looks at herself in the full-sized mirror.

Ashley is blown away by her look. She smiles, "I totally look like an eighties girl! A hot and horny eighties girl." Ashley turns to see herself sideways. "It's like I'm someone totally different. The shorts, the shoulder pads and the hair." She chuckles, "Most definitely the hair!"

As she looks at herself in the mirror a charge runs through her body, she bites her lip as she contemplates what she wants to do. She mouths to herself in the mirror, "You cannot do this Ashley." She sighs and rationalizes, "There's always the chance Rochelle used a condom or he pulled out."

"He's actually kind of cute. You could always get the morning-after pill." The more she rationalizes playing the more turned on she becomes. The thought of risking getting pregnant is just too much for her. "Oh God!" Ashley picks up her cellphone and purse and exits the room.

Ashley walks the short distance to the Manager's Office. As she walks she can feel a second pair of panties beginning to get wet.

Devin greets Ashley as she walks into the office, "Well look at you!"

Ashley grins nervously, "What do you think?"

"I think you look hot. Turned on?"

"Um, a little." Ashley bits her lip.

"Let's up the excitement level for you." Devin gets up and leads Ashley to the room next-door to a small makeshift TV studio.

Ashley looks at the room, her eyes get huge, "What are we going to do here?"

Devin grins, "We are going to play Preg Roulette!" Devin walks into the small control booth and flips on a couple of switches and the lights turn on.

"Okay."

Devin walks back out in the room. "Pretend you are on a game show and are about to find out your fate."

"Alright."

"It'll be fun." Devin points to the "X" on the floor near Ashley, "Step on your mark."

Ashley steps on the "X", "Like this?"

"That works!" Devin then picks up a microphone and talks into in a showbiz way,

"Good day everyone! and welcome to everyone's favorite show, Preg Roulette where one very special girl is going to have the time of her life. Today that girl is Ashley. Say hello Ashley."

Ashley timidly responds, "Hi."

"Ashley is 21 years old, single and is gainfully employed at a local fast-food establishment here in town. Most importantly, Ashley is not on any form of birth control and is smack dab between periods. Isn't that right Ashley?"

Her hormones racing, Ashley blushes, "Yes it is."

"So Ashley, tell us about the outfit you picked out. It's a very interesting selection."

"It's, um, Rochelle's."

"Well it looks very retro."

"Yes, they're from the eighties. You're not taping this, are you?"

Devin smiles, "Don't be silly! Can you turn for us, so we can get a good look at you?"

"I guess." Ashley slowly turns around for Devin. As she does, she feels Devin's eyes glued on her ass which she finds very erotic.

"Very good!" You look very sexy!"

"Thank you."

"Are you ready to fuck?"

Ashley feels a knot in her stomach as her pussy gets wetter. She nods her head, "Yeah, sure."

"Let's find out if you get to use a condom or go bareback." Devin hands Ashley an envelope.

Ashley looks at the envelope oddly, "What's in here?"

Devin smiles, "Your fate. Go ahead and open it."

Ashley nervously opens the envelope.

"What's inside?"

Ashley looks inside the envelope then smiles, "A condom!"

"How about that? No creampie for Ashley!"

Ashley takes a deep breath and smiles again, "No."

"Go ahead and read the slip inside."

Ashley pulls a slip that's inside the envelope and reads from it, "Name? Rochelle. Age at encounter? Twenty-one. Was alcohol involved? Yes. Were you in a relationship with your partner? No. Was it a one night stand? Yes. Where did you meet your partner? At an outdoor concert, Labor Day Weekend. Where did you have sex? In the back of his car. Did you ever see your partner again? No."

"You ready to reenact the scene?"

Much more relaxed Ashley grins ear to ear, "Ready able and willing."

"Let's go!" Ashley places the condom in her purse then follows Devin out of the studio.

A couple of minutes later Ashley finds herself in the Whisper Bay Inn's basement bar as a concert from the eighties plays on the big screen TV near the dance floor. As the music blares on the sound system Devin walks over with two beers poured in red solo cups. He hands one to Ashley.

"Thank you." Ashley then takes a sip from the cup.

"You're welcome." Devin motions to the dance floor, "Granted it's not an outdoor concert venue, but it'll have to do."

"I like it. You've got a great sound system down here."

"The last owner actually used to have bands down here when this was a functioning bar."

"Cool!"

Ashley and Devin pretend to be concert goers for the next few minutes as the music and video play in the bar. When the encore for the abbreviated concert finishes Devin is standing right behind Ashley with his arms wrapped around her. "I can give you a ride home if you want."

"I don't know what my friends would say." Ashley playfully responds.

"Tell them you met a really nice guy."

"I don't know."

"Tell them we live really close to one another."

"I don't know if they'll go for it."

"It'll be fun."

"Since you said it'll be fun, then I guess it's okay."

Devin walks Ashley through the Whisper Bay Inn's kitchen down a dark hall and up a set of concrete stairs that lead into a large garage. The two walk past Devin's late model BMW to the large early 80's Oldsmobile sedan that is parked on the other side of the BMW.

Devin opens the back passenger door and smiles, "Your chariot awaits!"

Ashley giggles, "An eighties car? You thought of everything." She then proceeds to get in the back seat follow shortly by Devin.

Once inside Ashley puts her hands down on the pillow-top seats, "Comfy."

"Only the best for my eighties girl." Devin closes the door behind himself.

"Do you think Rochelle got fucked on pillow seats?"

"I don't know, but I have a feeling Ashley is."

"Oh really?"

"Really."

Devin leans in and kisses Ashley. Ashley kisses back hard, instantly pushes her tongue against Devin's. Devin's hand finds its way to Ashley's leg as the sound of their kisses echo inside the car.

Ashley and Devin's tongues twirl as Devin's hand slowly moves up Ashley's leg. Devin pants between kisses, "You taste good."

"Yeah?"

"Yeah."

As the two kiss Ashley opens her legs slightly and Devin's fingers move onto her inner thigh and move in circular motions about halfway between her knee and torso. As Devin's lips move from Ashley's to her neck, Ashley pants, "So do you think Rochelle was a slut looking to get laid at that concert?"

Devin breaths into Ashley's ear, "What do you want her to be?"

Ashley, "A... total slut."

"Yeah?" Devin licks Ashley's ear.

"Yeah a total slut who wore tight little shorts in the hopes some strange guy would get in them."

Devin breaths heavily into Ashley's ear, "Then that's who she was then."

"Oh!" Ashley moans softly as Devin's tongue ever so gently brushes against her earlobe. She closes her eyes as his fingers move up her inner thigh only an inch or so away from Ashley's blue and white shorts.

Devin's mouth moves down from her earlobe and begins to kiss and lick Ashley's neck followed in short order by his fingers moving from her leg onto the crotch of her shorts. Ashley closes her eyes as she feels Devin's fingers move up and down on the taunt nylon. She moans softly, "Oh!" as she bucks up slightly to meet Devin's fingers.

A few seconds later Devin's mouth is back up at Ashley's ear. After licking it a couple times he whispers softly, "I can really feel your heat and wetness through your shorts."

Ashley pants back, "I can really feel your fingers on them."

"Like that?" Devin breaths deep into Ashley's ear.

"Yeah."

"I'm glad."

"I'm so fucking turned out."

"You brought the condom, right?"

"Yeah."

"Where is it?"

Ashley fumbles with her purse, unzips it and pulls out the condom and hands it to Devin. "Here"

Devin takes the condom and kisses Ashley on the lips deep, long and wet. As the two kiss Devin undoes his jeans. With the two lip locked Devin pulls down his jeans/boxers and out pops his erect eight inch cock.

Devin finally breaks the kiss so he can rip open the condom wrapper and pull the condom out. With Ashley watching Devin carefully places the condom on his purple head and carefully unrolls it down his thick hard shaft.

Once his cock is properly sheathed Devin grabs the waistband of Ashley's shorts. He then proceeds to tug on them. The front of Ashley's nylon shorts and satin panties stretch. Ashley lifts her butt up and the back of her shorts and panties slide under her ass. Devin pulls them down to her ankles then pulls Ashley's knees wide apart.

Devin slides between Ashley's legs and guides the tip of his condom covered cocked to her slit. He nudges it against Ashley and her swollen pussy lips part and the tip of his cock presses against them. Devin then finds the right angle and pushes...

"Oh!" Ashley moans out as she feels her tight pussy stretch to accommodate Devin's thick hard cock.

Devin pants back, "Fuck! You're tight!"

Gasping Ashley pants back, "It's been a while."

Devin begins moving his cock inside Ashley's tight fertile pussy. "I REALLY like it."

"Me too." Ashley answers as she begins to buck under Devin.

"You're so fucking wet too."

"That's because I'm totally ovulating."

Devin pushes deeper and deeper inside Ashley, "It feels unreal."

"Just make certain that condom stays on."

"I can always take it off."

"Don't you dare! I played and won fare and square. Oh!"

"Think you won?"

Ashley bucks up to meet Devin's thrusts "Yeah, and I'm collecting my pize."

"Prize?"

"Yeah!" Ashley swallows, "I wanna get fucked without worrying about getting pregnant."

"Your wish is my command!" Devin pumps Ashley's pussy faster.

"Oh God!" Ashley bucks up harder under Devin.

As the two fuck Devin reaches under Ashley's top and pull her breasts out of her bra. He then proceeds to cup her breasts with his hands.

"Oh! Oh!" Ashley moans as she bucks under Devin.

Devin pumps Ashley's fertile pussy deeper as his fingers play with her nipples.

"Oh, God!" Ashley bucks harder under Devin meeting each of his thrusts, his cock so deep in her pussy now.

Devin moves his head so his mouth is near Ashley's ear. He grunts, "You feel so fucking good."

Ashley closes her eyes as Devin's balls, his cum filled balls, slap against her ass. As she bucks under him she realizes that her fertile slippery pussy is craving one thing: sperm. "Oh!" She moans out.

Devin pumps her pussy faster, the springs on the car begin to squeak ever so softly in rhythm to Devin's thrusts and Ashley's bucks. Devin grunts, "Oh yeah!"

Ashley rolls her head back and forth as thoughts race through her mind. Thoughts about having him take the condom off. "Oh, God!" She gasps. As she thinks about a having a bare penis inside her. If only he didn't have the condom on, she could feel him pump his hot thick load of cum into her. "Oh God!" She moans again.

Devin pants back, "Oh!"

Ashley's white and blue shorts down at her ankles, her white top half pulled up and her hair now a mess. The little 80's girl really is a slut. "Oh God!" Ashley moans out louder. Devin pumps her even faster. Ashley pants, she wants the condom off. She wants to do it.

Devin moans, "Oh yeah!"

Ashley pants in Devin's ear, "Take the... Oh, God!" Before she can say anything else Ashley feels her pussy contract around Devin's cock and cum hard. "OH!!!" Ashley moans as she cums.

Devin frantically rams Ashley's pussy. Feeling her tight pussy is more than he can handle. He loses his rhythm, his body tenses then moans out, "Oh fuck! Oh fuck!" Devin thrust one last time deep inside Ashley's vagina. He buries his head in the seat next her and moans again, "Fuck!"

As Devin cums in the condom, Ashley cums a second time and moans, "OH!"

Movement in the car ceases as the two clutch each other intensely. Then finally after nearly twenty seconds Ashley pants, "Holy shit!" as she attempts to catch her breath.

Devin pulls his head from out of the seat and pants, "Like that did you?"

"Yeah, that was unreal!"

"It told you it was a fun game."

Ashley smiles, "Maybe too much fun." Ashley looks down to her waist, "Is the condom still on?"

Devin carefully pulls his cock out of Ashley's pussy, "Yeah."

"That's good."

Devin rolls to the side, "If you like that, there are still thirteen other outfits."

"As fun as it was, I really don't need to get too carried away."

"If you change your mind let me know." Devin pulls the condom off.

"You'll be the first to know." Ashley looks up at the clock on the dashboard. "Is that clock right?"

"It should be."

"I've got to go." Ashley begins to pull up her shorts and straighten her top.

A few minutes later, changed back in her work clothes, Devin walks Ashley to the front door. "You were a lot of fun. If you ever want to play roulette again or anything else send me a message on Facebook."

Ashley smiles, "Maybe I will."

"Have a great day."

"You too."

Ashley walks out the front door then down the sidewalk towards her car as she does she chuckles quietly to herself, "I guess Katie was right, I did have fun."