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Chelsie's Dilemma - Part 1

A night of frustration leads to more frustration...
May 5 th , 2011

The end of the semester is fast approaching and I couldn’t be any more excited. Not only will I be done with class, but summer time will be upon us and that means I’ll get to work on my glorious tan, lounge around doing nothing…and…that fucking thing called work…

It’s not entirely bad though. It’s a steady job I’ve held for the past two years and I’ve been fortunate to work for a very lenient boss who let me take some time off near the end of the semester to ‘focus’ on my studies. Really, I just wanted fuck around and then maybe get some studying done. I’ve lost count the number of times my hand has been in my cunt.

Speaking of which…

Maybe I’ll get lucky and find some poor bastard that’ll find interest in me and give me what I want – more like what I need… am I really admitting this right now? Maybe that one guy who has been frequenting the café lately will fill my current void… That’s if I can quit being a rambling idiot long enough to seem like I know what the fuck I’m talking about every time I open my mouth…

Okay, okay, I’ll do something productive other than just rambling away like I am right now.


He had been watching her from afar, taking in her beauty, as he casually sat back in his seat and began sipping on the tea he had ordered with his lunch. He wasn’t sure if she had ever noticed him while she always hustled around the small café, but occasionally he would catch her eye, even for a brief second, before she quickly diverted her attention elsewhere.

He knew she saw him looking at her, trying to express his interest in the beautiful waitress, but how many other guys had tried to catch her attention the same way? Some of the guys – and even other women – made it painfully obvious they had an interest in her. Others had even used the same approach as his, but would he stand out from the rest? Surely she’s immune to the attention by now.

Chelsie’s shift began sooner than planned because her lovely co-worker, Bethany Sharp, couldn’t make it into work. Something about studying for finals since it’s her senior year in high school. She chuckled to herself as the memories from her own high school days came flooding back and how stressed she had thought she was at the time. That stress level was nothing compared to what she was feeling now. Sometimes she wished she could go back and do it all again, but she quickly pushed those thoughts to the side before clocking in.

The café wasn’t terribly busy but there were still enough people in there to keep her from getting her own studies done. It wasn’t exactly frustrating – more like annoying – because she had her own finals to prepare for. Passing her finals meant freedom for the summer, and what single girl wouldn’t love that?

Chelsie began doing her job, ‘striving’ to keep each customer happy. She enjoyed what she did, but she only saw this job as being temporary until the right one came along, even though she had been there for awhile – not that she wouldn’t put any effort into the job, but she didn’t have any plans to make a career out of it.

Oh shit…there he is…

Her stomach dropped when she saw Him walk in the café. He usually comes in once or twice a week and, usually, he’s alone. She finds him very attractive but he hasn’t really spoken to her except for the one time she waited on him. She won’t serve him anymore because she became a rambling idiot in his presence.

“Really, Chelsie?” Shelby, another co-worker, asked after Chelsie asked her to take his table.

“Yes, baby doll. You know I can’t function around him…” she trailed off as she quickly looked away from him as he looked towards her, pretty much catching her looking his way.

“You’re so cute,” Shelby said before strutting off towards his table.

One of these days I’ll have the courage to approach him and actually be coherent when talking to him. Hmmm, I do wonder why he comes in so often.

Chelsie stayed just out of his sight while he ordered. There was something about him that made her freeze up, but she couldn’t quite figure it out. None of the girls were like that around him, and that was the most frustrating part about it all. She was supposed to be the confident one of the bunch, the one without any problems when it came to the opposite sex, but yet here she was completely losing it with a guy she could’ve had in her bed several times by now.

She watched him, as discretely as possible, through the duration of his lunch, while trying to get her own work done. She went through each of her tables, making sure everyone was taken care of, as she tried to ignore his presence that seemed to be growing stronger and stronger in the back of her mind. She could’ve sworn she could feel his gaze on her body as she moved from table to table, either gathering up the used dishes or taking care of a customer’ needs.

A devilish grin slowly crept over her face after she found a very safe vantage point to simply stare at him. She followed his eyes as he scanned the area, perhaps looking for her? That, she wasn’t too sure of, but she knew how she’d react if he happened to notice where she was and where she was looking. The grin turned to excitement – well, maybe it was closer to nervousness…maybe both – as she realized she could possibly play with his head and, just maybe, open up the door for something more than this little game of whatever-the-fuck-you-want-to-call-it. Taking a deep breath, she stepped out into the open, staring directly at him, before catching his eye and giving him a coy smile.


She looked away before she could see his reaction. Luckily for her, table 3 had already packed up and left, leaving her with a decent tip that made her feel better about the way things may go from there on out.

Maybe this will cause something to happen in my favor…

She began clearing the table, placing the dishes inside the bin, before ‘accidently’ dropping a fork to the floor. The naughty grin came over her face, again, before she slowly bent at the waist to retrieve the fork. She could feel his piercing gaze as she slowly stood back up, purposely making sure her ass was pointing in his direction. She could feel her panties dampening as she walked to the back area with dishes in tow, not returning to the front until after he had left.

Shelby slowly sauntered towards Chelsie, the smile growing bigger and bigger as they approached each other.

“Oh, so his name is Shane,” Shelby said, wrapping her arms around Chelsie’s lower back, pulling them together in a tight embrace. Chelsie wrapped her arms around her friend’s neck, imitating two lovers’ coming together. Yet nothing ever happened between the two of them.

“Oh? How do you know that?” asked Chelsie, her interesting spiking.

“I read it on his credit card. Assuming it wasn’t stolen or anything,” Shelby laughed out, slowly letting her friend go before taking a step back.

“Ha, who knows…”


“Maybe I should just nut up and talk to her…” Shane blurted out, randomly, as he and his friend Derek sat waiting for the green light.

“Huh?” Derek shot back, looking oddly over at his best friend. “Talk to who?”

Green light.

“I don’t know what her name is. I see her a couple times a week, but I can never seem to grab her attention long enough to string enough words together to make some sort of an impression.”

“Where do you see her at?”

“She works in one of those little restaurants down on 3 rd street. I can’t remember the name of the damn place…” He tried to think hard for the name of the small café, but to no avail.

Ponderosa? Or the Outlaw?”

“I think it was Ponderosa…I can’t quite remember…”

“Oh okay. Both have some pretty hot chicks working there. I really don’t blame you for not remembering where you had lunch at today,” Derek laughed out before looking over at his friend. “Hot I presume?”

“Really, dude? Would we even be having this conversation had she not been at least serviceable?” Shane shot back, taking his eyes off the road for a few seconds.

“Ha, well I’ve seen you try to pick up worse when you drink. That’s why I asked. Dude! Pay attention!” He yelled, causing Shane to quickly go back to the road, but not without a friendly hit to the arm.

“We don’t talk about those nights. Apparently alcohol makes my decisions for me, and we’ve all seen how some of those life choices have panned out…”

“Yeah, not so well, my friend…but really, if she’s hot, like you say, then you should go for it. Fuck it, what you got to lose?”

Shane simply shrugged his shoulders while they drove down the road. She seemed to cloud his mind more often than he was comfortable with. He’s had his fair share of infatuations with certain women before, but this was almost at a completely different level. He could still picture the way she moved while he would discretely watch her in the café – her hips swaying from side to side, giving off a distinguishable elegance that only she possessed. He could hear her laughter coming from behind the counter and had often wondered what could’ve made her laugh like that.

As the days and weeks passed by, the more she seemed to fill his thoughts. He couldn’t do his simple daily tasks without some sort of reminder of the blonde beauty that began to haunt his dreams at night. And it was usually subtle reminders that seemed to catch his attention and totally throw a wrench in whatever he was trying to accomplish.

Yet he still was not able to approach her to strike up some sort of conversation. Either she would completely avoid his area of the café, or she wouldn’t linger in any one area for too long. It was almost as if she were a little nervous to be in his presence, but why? With her looks she could take home any guy she wanted, so there was really no need to continue her antics. Unless it was her game of cat and mouse. And, in that case, he was ready to do whatever it took to land the pretty girl…or even bed her…


“Hurry the fuck up, bitch!” Shelby yelled through the bathroom door, clutching her purse, feeling rather impatient, as she waited on Chelsie to finish getting ready.

“Suck it, whore! I’ll be out in a few minutes…” she yelled back as she finished applying the last of her mascara.

“I can’t suck anything until your slow ass gets out of the fucking bathroom.”

Chelsie silently laughed to herself, knowing that, more than likely, Shelby was going to be sucking someone’s cock tonight. Letting that girl out in the wild usually ended like that if she wasn’t carefully watched, but Chelsie wasn’t exactly concerned about looking after her friend like that. If she wanted to have her fun, who was she to stop her? Besides, she was in a little mood for some lovin’ herself.

“Why does that not surprise me?” She asked, shaking her head, before giving herself one last inspection in the mirror, admiring the way she looked. Even she was impressed with the way she was able to make a simple outfit look good. Tonight’s gonna be a good night…

She opened the door to see Shelby standing there in one of her more…slutty dresses. It didn’t really surprise her to see her friend dressed that way, but it pretty much confirmed her intentions for the night. Chelsie looked her friend up and down before shaking her head and walking down the hallway towards her room to retrieve a pair of shoes.

Shrugging her shoulders, watching Chelsie walk down the hallway, “you know how much I love the dick.”

“Touché…” Chelsie couldn’t believe they were even discussing that at the moment. “Where do you want to go, anyways?”

“I don’t know. We’ll figure it out as we go…”


Figure it out as we go…yeah, great fucking call, Shelby!

Chelsie was fuming, pissed, and ready to kill her friend. Her idea of ‘figuring it out as we go’ happened to consist of wandering off with the first attractive guy that showed her any attention. She stared in disbelief as Shelby and this random guy disappeared behind a closed door. She knew she wouldn’t be seeing Shelby again that night, so she figured she may as well have her own fun since she was ditched like that.

She found an empty seat at the bar, quickly taking it before anyone else had the opportunity to sit down there. She knew she shouldn’t really be pissed at Shelby for ditching her, but they had planned to have a night out together. She didn’t think her friend would be gone just like that, leaving her to fend for herself in the sea of testosterone that was the club they happened to be in.

She began scanning the faces of the strangers that surrounded her, looking for any sign of someone, anyone that she may know. It’s not that she was uneasy sitting by herself, it’s just that she was already bored. Boredom would lead to drinking. Drinking would lead to excessive drinking. And excessive drinking would lead to leaving with some guy she didn’t know AT ALL, and she wasn’t exactly game for that. She could call her ex boyfriend, but that would mean conceding defeat to the game they currently had going.

After the break up, her and her ex would occasionally meet up for meaningless sex, to more or less keep their numbers down. But the more sex they had, the more her feelings for him came back. She knew she couldn’t allow it to keep going if they weren’t going to get back together. That would just be too painful and she really wasn’t the type of girl to sit in self pity.

“I bet you can’t go more than a month without calling me for sex again. In fact, I know you can’t do it.”

The subtle dare that was certain to make her fold within a couple weeks. But he underestimated her will power. She knew she could do it; he was just a temporary bridge until she found someone else. This was three months ago.

She decided to finally order a drink and see if that might help her relax. She received her drink before beginning to consume it, sitting all by herself…


No, that can’t be…can it? Why is…no, that can’t be…

Curiosity rising, he pried himself from the chair he was sitting in before going to the bar. He happened to see her looking around and, when she looked his way, he was floored to see her sitting by herself. But he wasn’t for certain if that was her or not. When she looked his way again, he recognized her eyes – oh those eyes – before it hit him exactly who she was.

“I’m trying to make sense as to why a girl as pretty as yourself is sitting at the bar, of this place, all by yourself…” he said, trying his best to shake the nerves that had somehow risen from the time he left his chair, to when he finally spoke to her outside of the café.

She froze. The voice was all too familiar, but it couldn’t possibly be Him, could it? She quickly glanced in the mirror behind the bar and was relieved to know it was Shane. What were the chances of them meeting up in this place?

Turning her head to look at him, “you remember Shelby, right? You know, the girl who waited on you this morning?” She shifted in her chair to get a better look at him.

“Yeah, of course…” he replied, raising his eyebrow as more of her body was presented to his gaze.

“Well, that fucking whore decided to leave with some guy and leave me here,” she said, obviously fuming over what happened with her friend.

“So that makes her a…whore…?” he asked, still a little confused as to why she didn’t have any other friends around to accompany her.

“Dude, you have no idea what she’s like. The dirtier and rougher the debauchery, the more she’s gonna love it…hell, she even took part in a foursome – and she was the only girl involved!”

“Wow…what a whore…” He shook his head, feeling a little grossed out by her promiscuous behavior. He really wasn’t into the slutty type of girls, just the kind he knew wouldn’t just give it up to him without making him work for it.

“Um, to say the least…” Now she was just pissed off. She downed the rest of her drink before slamming the empty glass on the counter, alerting everyone within a five foot radius of her and Shane.

“I need a Miller Lite and whatever she’s drinking,” Shane said to the bartender.

“Oh, I’ll just have a Cosmo…” she looked over at Shane as he paid for the drinks and took his beer. She watched the way he brought the bottle to his lips to let the cold beer flow into his mouth and down his throat. She became more and more attracted to him as she continued to simply watch him.

“Come sit with me. I’ll keep you company since your friend didn’t want to,” he said to her, followed by a smile that made her heart skip a beat.

“I don’t see any harm in that.” She returned the smile before following him back to where he was sitting.

“So why do you always avoid me when I come into the café?” He questioned her as they took a seat at an empty table.

“Can you keep a secret?” She looked at him with a mocking stern face.

“Sure can,” he replied, returning the same look.

“Well, you see, I’m attracted to losers…” she trailed off, trying to gauge his reaction before she continued, “I had a feeling you fit that persona, so I kept my distance.” She tried to keep a straight face, but lost it when he started shaking his head and laughing.

“I knew it! Damn, why didn’t I make myself not look so loserish?!” He laughed as he caught her eye and held the gaze.

“That was cheesy, I know,” she continued to laugh, holding the eye contact.

“Nah, it was cute,” he winked, causing her face to turn red.

“No, but really, I didn’t come around you because I didn’t know what to say and didn’t wanna sound like an idiot…”

“Oh,” he laughed, “I don’t think I would’ve fared much better.” He continued smiling at her.

“So far so good, right?” She began feeling somewhat nervous, not sure if she would be able to hold up her end of the conversation.

“Maybe. Just as long as you don’t fall apart on me,” he joked before playfully tickling her leg just above her knee, causing her to jump and laugh before playfully hitting him back.

“Jerk,” she joked back.

“So…tell me a bit about yourself.”

You want to know about…me?

She began delving into her personal life for the guy she’s had a lot of intrigue in. She told him everything: from past relationships to her favorite color, her celebrity crush to her childhood home, all the pets she ever had to her college major. She went on and on, feeling more comfortable around Shane while he took in everything she had to say. He was rather easy to talk to and that further cemented her attraction towards him.

“You know, in the midst of your story telling,” he interrupted her, “you never did tell me what your name is…”

“I thought you already knew it! I figured you would’ve over heard one of the girls say my name or something…”

“Either I missed it when someone said your name, or I didn’t know who they were talking about…” He knew her name is Chelsie, but he didn’t want her to think he was only paying attention to just her and freak her out.

“Oh, well my name is Chelsie,” she said with a smile, “your name is Shane, right?”

“How did you know that?” He raised his eyebrow in slight confusion, know that he didn’t tell anyone there what his name is.

“Shelby…she’s also a bit of a stalker. She happened to see it on your credit card and told me after you left…”

“Ah, yeah, that would make sense. It’s not like my name is on the card or anything,” he laughed, giving her a reassuring smile in which she happily returned.

Things were really clicking between the two. He easily made her laugh with his sense of humor and correctly timed tickles to either her legs or sides. The more they talked and played, the closer they got to one another. Before long, he ended up with his arm around her, leaning back in his chair, as she leaned into him. He felt confident in the situation and hoped he may have correctly played his cards to get her home and through to morning...hopefully even longer. But…he wasn’t exactly ready to make the attempt to fuck her. He wanted to wait things out and see if there’s something more than a physical attraction between them.

Chelsie was all but ready to take him home and let him have his way with her. Their playfulness had caused quite the mess in her southern regions and she definitely needed that to be taken care of one way or another. Now, was he going to take care of it, or was she going to have to do it herself?


May 8 th , 2011

Sorry I haven’t been around in a couple days to write to you. I have been busy with work, school and fantasies. School has been whooping my ass lately. The damn finals are quickly approaching and I’ve been trying to cram as much studying in as I possibly can. FML…why did I decide to go to college? It’s caused nothing but stress and taken time away from doing what I really want: lounge by the pool, work on my tan and maybe let some fool fuck me…okay, I don’t think that would ever happen. But I know if I really wanted to, any of the guys who have looked my way could’ve already been inside me. I’m not gonna stoop to Shelby’s level, no matter how horny I get. That’s why I play with myself ALL THE TIME. Hmm, but after what happened tonight…

Her thoughts drifted towards the night she spent with Shane. Even though he left almost an hour ago, she could still feel him, taste him, as she began to lie back. She softly closed her eyes as her hands began caressing her body. She could still feel him upon her, the way his hands moved over her breasts and down her belly. His teasing sensations were still upon her thighs and even down to her ankles.

A soft moan escaped her lips as she began teasing the rock hard nubs that jutted out from her heaving breasts. Her nimble fingers slowly encircled each nipple, sending a rippling effect from her breasts down to her moistening, tingling pussy. She gave her nipples a tug at the same time, causing her to jerk and writhe while her moans increased. She wanted his mouth to be on her nipples, to be licking, biting and sucking on them just the way she liked.

Her right hand trailed down her stomach, leaving her left at her breast, before reaching her aching, protruding clit. She slowly circled her aching love button while continuing to play with her nipple. The sensation and connection was almost too much for her to bear, but she continued her self inflicting teasing upon her own body. Her moans rose in pitch and tempo, making her realize just how quickly she might cum from the subtle touching.

“Oohhh, fuck…” she moaned out when she allowed her finger to apply more pressure to her clit.

She began rubbing harder and faster on her clit while simultaneously pinching and pulling on her nipple with more force. She felt the familiar tightening in her stomach, her breathing becoming more labored, as if being on the verge of an orgasm, before pulling her hand away from her pussy to linger close to the edge of bliss. She wasn’t ready to cum yet, but still was marveling in the feeling of knowing how quick she will cum when she graciously lets herself fall over that edge. But the real question: how hard was she going to cum?

Her finger dipped into her wet pussy, easily slipping past the open pedals of her box, before sliding it over her spot. Her mouth formed an ‘O’ as her soft finger continuously grazed the rough patch at the top of her walls. She knew it wasn’t going to last long as she applied more pressure to the wonderful spot, her other hand going to manipulate her aching, throbbing clit. She suddenly added a second finger, rubbing and fucking herself harder and faster, images of Shane on top of her pounding away at her tight, little pussy.

Her moans turned to screams, her breathing became more intense, and her fingers were as busy as ever, when finally the end was near. She felt the orgasm was just within reach when her phone went off, completely breaking her concentration and sending her orgasm back into the depths of her ready and soaked pussy. She angrily grabbed her phone before reading the text.

Holy shit…I’ve never been fucked by that many guys at once.

“What. The. FUCK?!” she screamed out, pissed and beyond frustrated that her slutty friend completely ruined what she was doing all because of a fucking gang bang. She tossed her phone on the floor before angrily rolling over and falling asleep. She didn’t even cum.


May 9 th , 2011

Shelby is a whore. A FUCKING whore! A whore, whore, whore, whore… She completely fucked up my thoughts of Shane. He didn’t fuck me, so I resorted to fingering myself to get off before going to sleep. But no. That fucking bitch had to tell me all about her fucking gang bang and how sore she was going to be afterwards. I. Do. Not. Fucking. Care!

Whatever, I’m gonna call Shane and either sweet talk him, or bribe him into fucking me.

Talk to you later. And hopefully with some good news.


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