Roulette - Round 02

Ashley nods, "Yes." The more Devin talks about Ashley's potential situation the more turned on she gets.

"So Ashley, tell us about the last time you played Preg Roulette."

Ashley answers timidly, "Last time I was an eighties girl."

"That's right! You picked out a pair of Dolfin shorts and top with shoulder pads."

"Yes."

"And what happened the last time you played?"

"I ended up having protected sex."

Devin grins smartly, "Would you say you got your brains fucked out?"

Ashley blushes, "You... could say that."

"So what are you hoping for this time?"

"Pretty much the same thing."

"So you want to have sex with a condom?"

"Yes."

"We will find out whether you get sex with a condom or get that ill-timed creampie very shortly. But first tell us about the outfit you selected this time for Preg Roulette."

Ashley grins slyly, "Well I'm a sweep."

"A sweep?"

"Yes, a girl who sweeps at a resort."

"I see. Well it looks like your sweep uniform fits you quite well."

Ashley blushes, "Yes it does."

"Let's take a good look at it."

"Sure." Ashley slowly turns around for Devin. As she does a charge goes through her.

"Very nice. It's almost like your uniform is glued on you."

Ashley grins sheepishly, "It's funny, it kind of feels like it is."

"How about that! Evan grins, "Ready to find out your fate?"

"About as ready as I'll ever be."

"Let's find out if you will have sex with a condom or if you get the dreaded ill-timed creampie." Devin holds up an envelope, "Inside is your fate." Devin walks over and hands Ashley the envelope.

"Here we go." Ashley opens the envelope then takes a look at the card inside.

"What does it say?"

Ashley reads from the card, "It says, learn your fate by opening the box."

"It appears we have Roulette clue box."

Ashley looks at Devin oddly, "Clue box?"

Devin points to the box sitting on the stool near Ashley, "Go ahead and open it."

Ashley walks over and pulls the top off of the box.

"Tell us what's inside."

"It looks like a pair of pants."

Devin smiles sheepishly, "really?"

"Yes." Ashley pulls the pants out, then her eyes get huge and her jaw drops, "Oh fuck! Oh fuck!"

"What? What is it?" Devin smirks.

"They're..." Ashley holds her hand to her mouth in disbelief, "maternity pants!"

"Tough break kiddo! But that's roulette."

In a near state of shock, Ashley's heart pounds and she breaths deep.

Devin then hands Ashley a second envelope, "Why don't you go ahead and tell us all the gory details."

Ashley's hand trembles as she opens a second envelope up and pulls a sheet of paper out of it and begins reading from it. "Sweep uniform data sheet. Name: Mita. Age at sexual encounter: eighteen. Sexual encounter with: guy in TV room at blue dorm. Were you in relationship with partner: no. Did encounter result in relationship: no. Was a condom and/or birth control used: no. Result of sexual encounter: full..." Ashley swallows, "ejaculation inside vagina which resulted in pregnancy."

After a pause Devin interjects, "There should be a brief synopsis at the bottom."

"My name is Mita and I worked at a resort the summer after I graduated from high school as a sweep. One day I was working a split so I had a couple hours to kill. So I decided to hang out in the TV room of the blue dorm. I got there at lunch so the room was filled with people so I took a seat on one of the couches near the big screen TV. As lunch was getting closer to be over over more and more people were hanging out in the TV room. It was about that time when this cute guy from the front desk sat next to me."

Ashley clears her throat and continues, "Just as soon as they arrived, the people left but the cute guy from the front desk had his hand down by mine. Before I knew it we were holding hands. After a while he leaned in and asked me if I wanted to go up to his room. I agreed and before I knew it we were having sex. I told him I wasn't on the pill, but that only seemed to make him fuck me more enthusiastically."

Ashley swallows hard, "The dorm room was hot and steamy, the sex was even more hot and steamy and nine months later I was a single mom."

Devin walks over to Ashley and hands her name tag, "Ready to play?"

Ashley responds meekly, "I guess."

"I'll meet you in the lobby in two minutes."

Ashley attaches the name tag to the bib of her overalls then looks up at Devin, "Okay."

Ashley exits the studio and walks the short distance to the lobby and nervously waits for Devin. About a minute later Devin walks out into the lobby with a small broom and dustpan with a long handle on it. He then hands them to Ashley.

"What are these for?"

Devin smiles, "If you're a sweep, you have to have the tools of your trade."

"Okay."

"I need you to sweep the bar downstairs first, then the first, second and third floors and then finally all of the sidewalks and driveways outside."

Ashley looks at Devin oddly, "Since when did roulette involve cleaning your building?"

Devin grins slyly, "This is all part of the game."

"Uh-huh."

"Then after your shift is done you can go to room nine to hang out." Devin hands Ashley a key. "This will get you in and out of the building."

Ashley takes the key, "If you ask me, it looks like someone's getting free ride out of this."

"Trust me, you'll get a ride." Devin grins again, "And it will be fun."

"Fun for you, maybe."

"I'll see you in about an hour."

Ashley proceeds down the stairs to the basement bar as she does she starts thinking about what she should do. Hooking up with Devin right now would be so risky but would be so fun.

After reaching the basement Ashley turns on the lights and begins sweeping. The more she sweeps, the more she thinks, she thinks about the risks and how hot the sex would be. The prudent thing to do would be to bail on him, but for some odd reason she feels obligated to see this through.

For the better part of an hour Ashley sweeps the building, trying to keep her mind on the task instead of what she is about to do after her task.

She then ventures out of the building into the hot mid-morning July sun. As she begins sweeping the front sidewalk she can feel eyes on her she turns to see a middle aged guy who is sitting at the red light on the corner look away at the last second.

Ashley turns back and leans over slightly to sweep up a cigarette butt off of the sidewalk. As she does she giggles thinking about guy sitting at the red light. He's looking at a butt too and it's not a Marlboro Light! She bends over a little further giving him a good view. After a couple of seconds she pulls back up, making certain he gets a good look at her tight yellow shorts that are on the verge of riding up her ass.

The light finally turns green and the car pulls away. Ashley feels a wave of excitement flow through her as she thinks about eyeing her, probably wishing he could get into her tight shorts. Ashley giggles again as she thinks about who is going to get in them and about how she is about to become a cum dump.

Ashley bites her lip then walks towards the front door of the Whisper Bay Inn and into the building.

A couple minutes later she finds herself sitting in the room nine, the room that has the big screen TV that's playing the Hangover. She takes a seat on one of the black couches near the front of the room.

About five minutes later Devin walks in and takes a seat next to Ashley. He smiles at her but says nothing. Ashley plays along, smiles then turns back to the movie.

About five minutes later Devin chimes in, "Why did they have to wreck a beautiful car like that? Couldn't they have found a Toyota Camry or a Nissan?"

Ashley turns to Devin and shrugs her shoulders and smiles, "I would have gladly let them use mine if they offered a trade."

Devin smiles back as Ashley turns back to the movie as he does he places his hand near her leg which Ashley first ignores. A couple minutes later Devin's hand moves up against her tan skin and Ashley's heart races as she feels fingers on her leg. At first they move in little circles near her knee. After a few seconds Ashley moves her hand down and holds Devin's.

The two innocently hold hands for the next ten minutes until Devin leans in asks softly, "Do you want to go back to my room?"

Ashley's heart pounds and her chest heaves, "Right now?"

"Yes."

Ashley exhales, "Okay."

Devin gets up then leads Ashley for down the hall. As they work the short distance down the hall to room thirteen Ashley's hormones rage. Her nipples are rock hard and she can feel her pussy getting wetter with each step.

Devin unlocks and opens the door to room thirteen and the two walk in. Inside is a room configured like a dorm room. Each side of the room has a twin bed and a desk. Upon seeing the beds and hearing the door close Ashley swallows hard knowing that she is now past the point of no return.

Devin walks up to Ashley as she pants. He leans in and kisses her deeply on her lips: Ashley kisses back. As their tongues swirl Ashley feels Devin's hand move down the back of her overalls on to her butt.

The two soon fall into one of the beds and the sound of deep wet kisses echo in room thirteen. Devin's hand then moves to the crotch of Ashley's shorts and beings to rub, softly at first. But soon the fingers move faster and push harder.

Ashley pulls Devin's tongue deeper and deeper into her mouth as his fingers grind against the crotch of her yellow short overalls. Ashley bucks against Devin's fingers, but it is not quite enough. Devin's fingers are so close but Ashley wants more. She bucks against his fingers haplessly and his fingers do a dance that teases her to no end.

Ashley bucks harder against Devin's fingers. The tight short overalls that showed her hips so well and rode up her ass to the point where a middle aged man wanted to fuck her are now becoming a total hindrance. Ashley pants into Devin's mouth as she undoes the right suspender loop. Devin's fingers then move faster and press harder against the taunt cotton. Ashley feels her short overalls and Pac Man panties pushed firmly against her pussy.

As her tongue is pulled into Devin's mouth she pulls hard against the left suspender loop, but it jams. She pants into Devin's mouth, "Uh!" After two more tries she finally manages to get the loop of its hook and the bib falls down.

Devin proceeds to pull on the bib and the front of the shorts stretch. Ashley lifts her butt up and the entire garment slips down her thighs, knees, shins, ankles and off.

Ashley pants then arches a second time and pulls her Pac Man panties down her hips and grins smartly, "Ghost me!"

Devin grins, "You're about to get ghosted all right!" He then grabs the panties and pulls them down the rest of the way. After her panties are free from her Ashley pulls her top up and off. Devin follows suit and pulls his polo up and off.

The two begin to kiss again as they do Devin undoes his pants. In one fell swoop he manages to get his pants and boxer briefs down and off. Out pops his eight inch rock hard cock. Ashley reaches down and wraps her hand around it. She gasps as she feels Devin's girth again.

Devin grins then proceeds to push Ashley further up the bed then spreads her legs and slowly slides between them.

Ashley's heart pounds as she feels Devin's bare cock rub against her inner thigh. The realization that she's about to get fucked bareback mid-cycle hits her. Ashley pants, "Oh God!"

Devin doesn't give Ashley and chance to back out as he guides his purple head to her slit, parts her pussy lips then finds the right angle and pushes inside her. "Oh!" Ashley gasps as she feels Devin's big bare cock slip inside her unprotected pussy.

Devin begins to move in then out, in then out inside of Ashley. Ashley pants as her slippery pussy accommodates Devin's thick shaft. In and out she feels Devin's cock pumps her tight hole.

Ashley begins bucking under Devin meeting each of his thrusts. She closes her eyes as feels his cock, no his bare cock penetrate her pussy. "Oh! Oh!" Ashley pants softly feeling the sensation of a hard thick cock slide in and out of her.

Devin thrusts a little faster, the sounds of Ashley having sex now echoes in the room.

Ashley pants a little louder, "Oh! Oh!" Her pussy feels so good; it always does when she's fucks when she's ovulating. But this time is different. This time there is a bare cock inside of it! "Oh God!"

Devin pants back, "How's our little sweep doing?"

Ashley opens her eyes and grins, "She's doing really fucking good!"

"Yeah?"

"Yeah!"

"Good! I saw you sweeping earlier and you looked totally hot."

"Oh Yeah?"

"Yeah."

Ashley pants, "There's something I should tell you."

"What's that?"

"I'm not on the pill."

"Really?"

"Really."

Devin pumps a little faster.

"Oh!" Ashley moans out. "Oh fuck!"

Devin pushes his bare cock deeper and deeper into Ashley's fertile pussy.

Ashley swallows, "Oh God!"

Devin the grabs Ashley's legs then pulls them up and back tilting Ashley's vagina at the optimal angle for penetration.

Ashley gasps, "Oh fuck!"

Devin thrusts using all of his weight to drive deep into Ashley.

Ashley pulls her legs back further and she can now feel Devin's cock ramming her cervix, getting it ready for his load. This thought, sends Ashley over the edge, she gasps, "Oh God!" She clinches, then cums hard, "OH!" Her pussy clamps hard on Devin's bare cock.

Devin pumps furiously using all of his weight to drive deep and hard into Ashley's orgasming pussy. Devin's cock makes slurping sounds as it relentlessly pumps Ashley's wet tight pussy.

"OH!" Ashley moans out loudly as her pussy clutches Devin's bare shaft that is now pumping her even faster. In and out she feel's Devin's thick hard shaft pump her pussy as his cum filled balls slap against her ass.

Devin pants, "Feels good bare, doesn't it?"

"Yes!"

Devin continues pumping.

Ashley blurts out, "you have..."

"Have to?" Devin pumps faster.

"You know!"

Devin uses all of his weight to drive deeper and deeper into Ashley.

"Oh!" Ashley moans out. "You, you have to pull out!"

Devin pumps even faster.

"OH! OH!" Ashley cums a second time her fertile vagina clamps tightly around Devin's bare penis. Intense waves of pleasure overtake Ashley as she cums hard.

Devin pumps furiously into Ashley's unprotected pussy grunting as the bed thumps. As the sounds of Ashley getting pregnant echo in the room Devin begins to lose his rhythm. His body tightens and gasps, "Oh God!"

Ashley bucks up to meet Devin's bare penis as he thrusts on final time deep inside Ashley's fertile vagina and holds it inside her.

"OH!!" Devin moans out.

The next thing Ashley feels is the warm wet sensation of hot thick cum squirting right against her cervix. "Oh fuck!" She pants as the sensation sends her into a third even more intense orgasm. Ashley then raises her hips up so she can get every bit of Devin's seed inside her. Her vagina sucks the sperm deep into her.

Ashley wraps her arms around Devin as he pumps her fertile vagina full of sperm.

Then a few seconds later Devin finally finishes and Ashley pants, "Oh my God!"

Devin catches his breath, "Enjoy yourself?"

Ashley grins ear to ear, "You could say that."

Devin chuckles as he pulls his cock out of Ashley and rolls over, "Good."

Ashley takes a deep breath then reaches down and slips a finger inside her freshly fucked pussy and pushes deep inside where she feels cum deep inside her. She turns to Devin, "You naughty, naughty boy."

Devin begins to get dressed as Ashley pulls cum out of her pussy with her fingers. "Yes, but you are a naughty, naughty girl."

Ashley giggles as cum ozzes out of her slit, "Maybe."

Later that morning, dressed in her t-shirt and shorts, Ashley walks into her apartment carrying a bag from Walgreens when she is greeted by Jamie. "Hey there."

Ashley nonchalantly replies, "How was the Bay View last night?"

Jamie shrugs her shoulders, "Uneventful."

"So I didn't miss anything?"

"Not a thing."

"You were up early."

Ashley grins, "I got motivated this morning and decided to run some errands."

"Well, I decided to sleep in."

"Sleep good did you?"

"Yeah, I did."

Ashley grins as she walks out of the room and down the hallway, "I bet."