Kylie's 1st Fantasy Connection

Kylie Murdock - 20, tall and slender with sandy blond hair - anxiously walks up to the front entrance of the Whisper Bay Inn and rings the doorbell. As she waits for an answer she fidgets. After about twenty seconds Kylie mumbles under her breath anxiously, "Common."

The Whisper Bay's reputation for being host to crazy sex parties, wild hookups and kinky sex games fuel Kylie's anxiety. Adding even more fuel to the fire is the fact that if things go as Kylie hopes her visit will result in not one but two wild hookups that she will be the main participant in.

Finally, the buzzing sound of the door being unlocked remotely is heard and Kylie lets out a sigh of relief, "Finally!" Kylie opens the door and walks inside the weathered wood-framed structure.

Awaiting Kylie in the cramped lobby of the 19th-century building is Missy Martin - 27, blond and curvy - who stands behind the small front desk. Missy smiles as she greets Kylie, "You must be Kylie."

"Yeah," Kylie answers back as she walks to the front desk.

"I'm Missy."

"It's nice to finally meet you," Kylie answers back relieved.

Missy takes a hard look at Kylie then smiles, "I think we nailed the sizes."

"Really?"

"Yeah, let's get started. I have the clothes in the other room."

Missy motions for Kylie to follow her back down the first-floor hallway and Kylie follows her to a door that's labeled "Wardrobe." Missy unlocks the door and the two walk inside.

When Kylie walks inside she is amazed at the racks and racks of women's clothes the large room houses, "Wow!"

Missy walks over to a couple of hangers on the front rack and hands them to Kylie.

"Are you a thong girl?"

Kylie looks at Missy uneasily, "Not really."

"For these encounters, you'll be."

Kylie responds less than enthusiastically, "Okay."

Missy walks to a cabinet that's against the near wall. "Don't worry, it'll be worth it."

"I hope so."

"Pick your poison, silk, nylon or cotton."

"Um, cotton, I guess."

Missy pulls two nondescript cotton thongs out of new packaging, one navy blue the other pink. She then walks back over to Kylie and hands her the undergarments.

"The shoes you have on should work with both outfits. Across the hallway is a changing room where you can try everything on and see how they fit and how sexy and slutty they make you feel."

"Cool."

"Try on the shorts first then the yoga pants. If the yoga pants fit, wear them into the office next door. I really wanna see how they look on you." Missy grins, "If they fit like I think they will, I have a surprise for you."

Kylie looks at Missy anxiously, "Okay."

Kylie takes the clothes and heads out of the room to the dressing room across the hall. After she closes the door she takes a look around the girl-friendly room and shakes her head, "This place is fucking insane!"

Kylie giggles as she walks over to the table that has a wealth of beauty products on it, "With a little luck this is gonna be insanely fun."

Kylie gets undressed then puts on the pink thong. She then pulls the royal blue shorts and Mauve t-shirt from the first hanger.

Kylie carefully steps into the shorts and pulls them up. As the cotton/spandex blend fabric of the shorts stretches over her slender butt it becomes very apparent the shorts are very short and ultra-tight.

Kylie grins as she pulls hard the shorts to get the button secured, "These are tight as fuck!"

After zipping the shorts up, Kylie grabs the mauve-colored T-shirt and pulls it over her head and on. After pulling her hair out of the garment she straightens it and walks in front of the full-length mirror on the wall.

As she turns sideways Kylie giggles, "These are going to totally ride up." Kylie turns to look at her other side, "These are totally slutty." Kylie giggles, "And I like it!"

Satisfied that the shorts and t-shirt will serve their purpose, Kylie takes them off. Next up is the second hanger which has pair of yoga pants that have an olive green camo pattern on them and a light gray/greenish halter top.

Kylie Steps into the yoga pants and pulls them up. The pants cling to every square inch of Kylie's legs, thighs, hips, navel, butt and crotch. After putting on the top that barely meets the waistband of the yoga pants Kylie walks back to the full-length mirror.

Kylie takes a long hard look at herself in the mirror and smirks, "Yeah, this is different." Kylie shakes her head, "form-fitting camo is not something I would pick out." Kylie shrugs her shoulders, "Hopefully it works."

Kylie puts on her shoes then heads out of the dressing room to the manager's office next door.

Upon entering the room Missy greets her, "You go camo girl!"

Kylie blushes, "This is definitely a different look for me."

"Well, I'm jealous! Those pants look really good on you."

Kylie shrugs her shoulders, "Thanks."

"I wish I could fit in them like you." Missy points to the chair facing the desk, "Have a seat."

Kylie takes a seat in the chair.

"How do you feel?"

"Want me to be honest?"

"Of course"

"Excited, nervous and... and kind of turned on."

"Good! You're gonna have a LOT of fun."

"I hope so. Because, I um, have never done anything like this."

"That's what will make it so intense for you."

Kylie looks at Missy eagerly, "Really?"

"Yes. So how much do you know about Josh and what he wants to do."

"He told me he likes the idea of sleeping with me soon after I've slept with another guy. I guess he's into the slutty girl with low self-esteem thing."

Missy grins, "As you know from the website, we specialize in helping people act out fantasies and reenact past experiences."

"Right."

"Ryan wants to reenact a scene from his past."

"What scene does he want to act out?

"When Josh was going to Seaside College, his roommate hooked up with a girl named Renee when the two were working on a school project. As fate would have it, the walls of the student slum Josh was living in had paper-thin walls and he was able to clearly hear all the intimate details of Renee's sexual encounter with his roommate."

"Okay."

"After the romp, the roommate quickly discovered that Renee was very clingy and a bit of a headcase. So, he quit answering her texts and phone calls. This of course made Renee more clingy and got her to freak out to the point where she showed up at Josh's door a couple of nights later."

"Was there a scene?"

"No."

Kylie looks at Missy inquisitively, "What happened?"

"When Renee showed up the roommate wasn't home. Renee was persuasive enough to talk Ryan into letting her in."

Kylie chuckles, "Must have been the camo pants."

"According to Josh, she was wearing a pair of them just like you are now. She wore the blue shorts the night she fucked the roommate. I guess he searched the internet looking for exact matches for both outfits."

Kylie's eyes get big, "Wow!"

"After an emotional breakdown, Renee and Josh ended up in an intense make-out session."

"Did he fuck her?"

"No, Josh came to his senses and sent her on her way before things escalated beyond kissing and heavy petting. As he found out later, It's probably just as well that he did." Missy grins, "Renee ended up getting knocked up by a guy at a party a couple of months later."

"Oh my."

"So, what he wants to do is reenact the scene again. That's where you come in."

"Yeah?"

"Yes, you get to be Renee."

Kylie feels a wave of excitement flow through her, "Okay."

"Only this time, Josh wants to make certain that he fucks Renee."

"Yeah?"

"Bareback just like his roommate did."

Kylie's heart races, "Okay."

"Is that something, you feel comfortable with?"

"Um, yeah, ah... I'm not on the pill so, I just need to figure out the timing is all."

"Remember, you have to fuck the roommate bareback too."

Taken aback, Kylie fidgets nervously, "Of course."

"When will the timing be right?"

Kylie pulls out her cellphone and studies an app for a couple of seconds, "Next weekend looks, safe... I mean good."

"Then next weekend it is."

Kylie puts her cellphone away, "Okay."

"That is if you think you could be needy and insecure. Like Renee was."

Kylie nervously nods her head, "I think I could figure that out."

"Good." Missy grins, "In fact, if you can whip up some tears that'd be great too. You need to be totally clingy with no self-confidence."

"If that's what he wants, that's what he'll get."

Missy smiles, "You'll love this."

Kylie looks at Missy oddly as Missy opens a desk drawer and pulls out a photograph, eyeglasses, hairbrush, envelope and hand mirror. Missy then walks over and hands Kylie the hand mirror then places the other items on the desk.

Missy begins brushing Kylie's hair with the hand brush. After a few seconds, Missy succeeds in brushing back Kylie's hair. She then tells Kylie, "Put the glasses on."

"Okay." Kylie puts on the fake eyeglasses whose frames have a teal tint to them.

Missy then hands Kylie the photograph. Kylie's eyes get big when she looks at the photo, "Who's this? Oh my God! She's wearing the same pants and shirt I am!"

Missy grins, "That's Renee and as fate would have it, Josh found a photo of her in green camo yoga pants."

Kyle gasps, "Oh my!"

"You look just like here. Particularly if you had shorter hair."

"That's, that's crazy!"

Missy lets go of Kylie's hair, "I have a feeling you're going to have a lot of fun being a clingy and insecure girl." She grins smartly, "A clingy and insecure girl who sleeps with guys way too easy."

Kylie grins, "clingy, insecure and...reckless!"

"Precisely!"

Missy motions for Kylie to follow her, "Let's go upstairs."

"Okay." Kylie puts down the hand mirror and photo and follows Missy out of the office still wearing the glasses.

A couple of minutes later Kylie finds herself on the second floor of the building. She then follows Missy into room number two which is decorated like a female college student's bedroom.

"This should be a good hookup room."

Kylie gazes around the room then nods her head, "Yeah."

Missy jumps on the queen-sized bed and grins mischievously, "The bed is nice and bouncy."

Kylie giggles as Missy bounces, "Cool!"

"I've got to show you this. It'll blow your mind."

Missy gets out of the bed and walks Kylie out into the hallway and into room number three, next door. She then points to the window on the left wall in front of a couple of chairs, "Take a look through the window."

Kylie walks up to the window and her jaw drops as looks through it. She then turns to Missy, "Holy shit! That's the room we were just in!"

Missy smiles, "That's right! This is an observation room."

"I thought that was a weird place to put a mirror!" Kylie turns to Missy, "Who would you be observing?"

Missy smiles then walks up and opens the vents under and adjacent to the window, "You can see, hear and smell anything that's happening in the other room."

Kylie breaths heavily, "Oh my God!"

"What that means is, while you are getting busy in the bed in number two, Josh will be sitting here in number three a mere 18 inches from you, watching, listening and taking in all of the sights, sounds and scents of you getting drilled relentlessly."

Kylie's heart begins to race, "Oh my God!"

Missy smiles ear to ear, "Does that get you all fired up?"

Kylie looks into the window in a state of near shock and nods her head, "Yeah."

"Good. Do you have someone picked out for the first encounter?"

Kylie grins slyly, "Yeah, I've been talking to this guy online, he's a total player."

"Oh yeah?"

"Oh yeah! He's such a candidate for this."

"Playing a player is like bull shitting a bull shitter, it's a very hard endeavor to pull off."

"That may be, but he's gonna get what he wants in the end." Kylie grins slyly, "He's gonna get inside those tight blue shorts, so I like my chances."

Missy grins, "I can tell you're going to have fun. Let's go back downstairs so you can read Josh's letter and we can work out the logistics."

"Okay."

Missy and Kylie head back towards the office.

Two Fridays later Kylie pulls her mother's Korean car into a parking spot at Waterfront Park in downtown Seaside. After parking the car she turns it off and pulls her cellphone out of her purse.

On Kylie's phone is a text message from Missy which reads, "Josh should be sitting in the lobby when you come in with the Roommate." Remember, don't say anything to him. We don't want you to blow his cover. Good luck and have fun!"

The "Roommate" Missy is talking about is actually Ryan, the guy Kylie's been talking to online. If things go as planned, Kylie plans on taking him back to the Whisper Bay Inn to fuck bareback while Josh watches from the observation room next door.

Kylie nervously types back to Missy, "Thanks! TTYL."

After sending the text Kylie opens up her period app and takes one last hard look at it. Seeing that Sunday, the day she is supposed to hook up with Josh is the last "safe" day before she hits her fertile time gets Kylie highly agitated.

Kylie sits in the car contemplating what she's about to do. She knows what she's doing is reckless and filled with risks, including but not limited to pregnancy, but this really turns her on.

In fact, everything from the short tight shorts, goody yoga pants, underwear she wouldn't normally wear, to the fake eyeglasses and freshly cut hair (exactly like Renee's), to having Josh watch her have sex, to knowing that she's going to be super nervous about getting her next period are fueling the furnace right beneath the taunt blue fabric between Kylie's legs.

As Kylie's chest heaves inside her mauve top she puts her phone in her purse and pulls out the photo of Renee, Missy gave her. She pulls down the visor and looks in the vanity mirror then back at the photograph several times. The more Kylie looks at both, the fewer differences she can conceive between herself and Renee. This just makes more heat builds inside Kylie's tight blue shorts.

Next Kylie pulls out the fake glasses Missy gave her and puts them on. She compares herself again to the photo and gasps, "Oh my God! I'm gonna do this! I'm gonna be a vulnerable little slut!"

Kylie takes a deep breath, replaces the visor and sticks the photograph in the glove compartment and smirks, "Here we go!"

Kylie exits the car and begins walking towards the waterfront. As she walks she giggles, "Yep, the shorts are riding up, totally on schedule."

A couple of minutes later Kylie is walking near the waterfront when she hears a guy yell out, "Renee?" She continues walking when the guy yells again, "Renee?"

Suddenly, Kylie looks towards the sound of the voice and sees Ryan Henderson - 22, blond with a moderate build.

Kylie smiles, "Ryan?"

Ryan smiles back, "Yes!"

"Hi!" Kylie responds walks up to Ryan.

"You look different than your pic from online."

Kylie attempts to sound worried, "I cut my hair, I hope it's okay. I kind of wanted a fresh look for you."

"Yeah, it looks great."

"I was really hoping you'd like it.

"I do." Josh's eyes move down to Kylie's shorts, "In fact, you look great in general."

Kylie answers apprehensively, "Do I?"

"Yes."

Kylie smiles, "I'm so glad you think so."

"So what did you want to do?"

"I don't know, wanna take a walk down the boardwalk?"

"Sure."

"Common!" Ryan leads Kylie up the sidewalk towards the boardwalk.

About an hour later Kylie and Ryan sit on the grass talking in a secluded part of the park. As they talk not only is it evident a player is getting played, but the line between fact, fiction and fantasy becomes blurred.

"I'd really like to be in a relationship again, but I'm really leery of risking getting hurt."

"You're a really pretty girl, I'm sure you will be soon. Besides, Dennis was an idiot to cheat on you."

"You think so?"

"Yes. What's more, not every guy out there cheats."

Kylie sighs, "God, I hope not."

Ryan smiles, "You'll see that I'm right."

"I mean I really tried to make him happy and look hot for him."

"You've got a lot to offer and you look hot."

Kylie shakes her head, "I even let him cum in me!"

It takes a couple of seconds for Ryan to find a response, "Well he didn't deserve it."

Kylie looks into Ryan's eyes, "You're a real sweet guy."

"I do have my sour moments."

Kylie laughs and taps Ryan's knee, "You're funny."

"Unfortunately, that's about the only thing most girls like about me."

"I think that's a gross exaggeration"

"I wish."

Kylie smiles, "Well I think you are funny, handsome and very understanding."

Ryan smiles back halfheartedly, "Thanks."

"In fact, you're handsome enough for me to invite you back to my place if you wanna hang out some more. It's just down Bay Street."

"I'd like that."

Kylie smiles seductively at Ryan, "Common."

Kylie and Ryan get up and off of the grass and walk off.

Five minutes later the couple is walking up to the front entrance of the Whisper Bay Inn. Ryan looks at Kylie oddly, "What are we doing here?"

"I'm staying here until I can get a place on campus next semester."

"I didn't know this was a functioning hotel."

Kylie enters a code into the lock, "It's not." The door unlocks, "I needed a place to stay and know a friend of the owner."

"Oh."

"So I'm just kind of passing through." Kylie opens the door.

Ryan grabs the door from Kylie, "Gottcha."

Kylie walks into the lobby and Ryan follows her. Sitting in one of the chairs in the lobby is Josh Bray - 29, black hair and medium build. Kylie makes eye contact with him and feels an intense bolt of excitement hit her as she and Ryan head towards the stairs.

As Kylie leads Ryan up the stairs, she can feel Josh's eyes locked in on her ass as if they were burning right through her tight blue fabric to get inside them. With each step Kylie's heart pounds faster, her breath becomes deeper and the thong that's clinging to her pussy becomes a sponge sucking up moisture and heat.

A few seconds later Kylie and Josh walk into room number two. As Kylie closes the door and secures the deadbolt Ryan looks around, "This is a cozy room."

Ryan takes a seat on the edge of the bed as Kylie hangs her purse on a hook in the closet, "It serves its purpose."

"Oh yeah?"

"Yeah."

"What exactly are your purposes?"

"Shelter, a place to sleep and study."

"Oh."

"You sound disappointed."

"Why would I be disappointed?"

Kylie grins slyly, "Because you're a guy."

"Yeah, so?"

"A guy's mind is always in the gutter."

"Says who?"

"Says me."

Ryan smiles slyly, "The only thing I know about the gutter is that it is no place to be alone in."

Kylie raises her eyebrows, "Oh really?"

"Really."

"The gutter is a much more friendly and more fun place to be when you have someone cute to roll around in it with."

Kylie puts her hand on her waist and shifts her weight to one side, "Well, I'm sure you have some cute beer-drinking buddy that you can roll around in it with."

"I'm not into guys, thank you very much."

Kylie shifts her weight back to the other side, "Then what are you into?"

"Girls!"

"Oh, really?"

"Yeah!"

"Well, maybe I'm into girls too."

Ryan raises his eyebrows, "Oh really?"

"Really."

"If you like girls, you certainly aren't the butch type."

"How do you know?" Kylie runs her fingers through her hair, "I do have the hair for it."

"Your hair is short..." Ryan chuckles, "But your hair is cute, not to mention those shorts are not anything butch."

Kylie shifts her hips again, "Why do you say that?"

Josh grins, "Because they are glued on to you."

"No, they aren't!" Kylie pouts, then plays with Josh by pointing to the button of her shorts, "There's this little button here that keeps them all together."

"It's keeping them together, alright."