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Chelsie's Dilemma - Part 3

"Derek pays Chelsie a visit, almost ruining her date with Shane..."

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Chelsie happily walked into work the next morning feeling like nothing could bring her down from the high she was feeling after the day before.

Not even looking at Shelby could make her mad. After all, she finally got some.

Everyone seemed to notice that something was different about her. She was glowing, smiling bigger and she just seemed more vibrant. She had an extra bounce to her step and was acting more upbeat.

“Damn girl, what happened to you?” Shelby asked as Chelsie made her way behind the counter.

“Nothing, I’m just in a good mood,” she replied, flashing another big, bright smile.

“Hmm, if I didn’t know any better, I’d say you got some dick last night…”

“Maybe I did, maybe I didn’t,” Chelsie winked before heading for the food to be served at table six.

“Whoa, wait, did you?” Shelby yelled out after her friend as she made her way back to the front of the café to deliver the food.

“What do you think?”

“No way!”

“Yep.”

“Oh, that explains why Derek was here yesterday.”

“Wait, what? No! That’s not who I fucked last night,” Chelsie whispered to Shelby.

“Then who was it?”

She grabbed Shelby by the arm before pulling her into a secluded place so they wouldn’t be over heard by anyone – especially some of the customers that were a little nosey from Shelby’s loud mouth.

“Shane,” she said before giving Shelby that knowing look.

“Shane…?”

“Are you that dense? Shane! The Shane that’s in here all the time.”

“Ohhh!! Nice! How was it?!” Her neck turning a slight shade of red.

“Fan-fucking-tastic. I haven’t been fucked like that in a long time…” Chelsie trailed off as she began thinking about what happened, her panties beginning to slightly dampen.

“I might have to find out for myself…”

“Don’t you even fucking think about it. I mean it, Shelbs. Don’t do it,” she warned her friend even though she could still see the wheels turning in that slutty head of hers.

“Okay, okay, I won’t do it. And only for you, baby.”

“Good.”

***

May 12 th , 2011

Shane and I have a date tonight. He’s planning on taking me out to The Olive Garden. I’m so excited! I haven’t been there in so long. I don’t know, maybe we’ll go out for some drinks later. Or we can possibly drink there. Who knows? Hmm, I wonder if he’ll take me to a movie as well…?

Anyways, I’m definitely looking forward to this night! I can’t wait to know what exactly happens.

I’ll be back later with the details.

***

Chelsie laid out three of her favorite dresses on her bed before trying to decide which one to wear. The first was a simple white sun dress that hugged her breasts and stomach before freely flowing around her waist and thighs. The second was the always dangerous and sexy little black dress. She was highly considering this one just to gauge the reaction of Shane and everyone else at dinner. The third was a strapless blue dress that hugged every curve her body had to offer, ending mid thigh.

Hmm, decisions, decisions. They suck and I hate them.

She picked up the white sun dress before holding it against her body, closely inspecting herself in her full length mirror.

I like this one, but I’m not too sure it’s exactly…appropriate for the setting we’re gonna be in. Well, then again, yeah it is. But I don’t have enough of a tan to pull this one off.

She carefully laid the dress back on the bed before picking up the black dress. She held it close to her naked body, admiring the way the dress would look on her. She knew this dress would get her anything she wanted that night: whether it is drinks, sex, or whatever. But would it be too sexy for where they’re going?

Fuck…I love this dress though…

She picked up the strapless dress next.

Form-fitting dress that’s only going to show off the curves my body has to show off. Hmm, but is it really necessary for tonight?

She laid the dress back in its original place on the bed before making her decision. Going on a whim, she decided to go with the white dress. Mostly because it allowed her freedom from the waist down. Who knows? Maybe she had a little something extra planned while they were out and about…

She slipped into the white dress before inspecting herself in the mirror. She ran her hands over her stomach and down her ass and thighs before doing a subtle twirl to see how much of the fabric would flow with her. She felt beautiful and enchanted at that moment, admiring the way she looked, the white dress hugging her upper body, the flowing fabric caressing her smooth thighs. She thought she felt the subtle hint of moisture building in her panties until a knock came on her door.

***

Shane began making the final preparations for the night. He already had the reservations for the restaurant made, so all he really had to do was get everything ready for afterwards. Derek was going to be gone for the night so he figured he’d bring her back to his place and let her see his living arrangements since he’s already seen hers.

He sat the bottle of wine on the counter before heading to the bathroom to shower and get ready for the night. He told Chelsie to be ready by 7 and he fully planned on sticking to that. After all, the reservations were for 7:45.

But I’m sure I’m gonna be waiting on her to get ready. I’ll be waiting on a woman… sheesh.

He showered, shaved and then got dressed in a simple polo shirt with a nice pair of dark jeans. After doing some final inspections, he decided to make one final stop before going to pick up Chelsie.

***

6:27 P.M.

Chelsie had just finished checking herself out when a knock came to the door.

He told me to be ready by 7pm… what the hell?

She got up to answer the door, fully expecting to see Shane standing there with flowers in hand – or something along those lines – but for some reason, her expectations and reality didn’t want to line up at that moment.

“What are you doing here?” she asked, staring blankly into the face of her ex, Derek.

“What? I can’t stop by and say hi?” he asked with a smug look on his face.

“No, it’s just that I wasn’t expecting you…” she shot back, trying to discretely look him over without getting caught.

“I should’ve called first. May I come in?”

I do have some time to kill…why not?

“Yeah, sure.”

She opened the door for him before walking back to her room, sensing his eyes penetrating the thin fabric of her dress to stare directly at her ass.

“What are you all dressed up for?” he asked, following her into her room.

“I have a date…” she reluctantly answered.

“Ohhh, I see,” he began before moving closer to her, “is it…romantic?”

“Eh, could be. What’s it to ya?”

She shrugged her shoulders before stepping away and towards the mirror to finish her make-up. She pulled her up into a loose ponytail before reaching for her eye liner.

“Maybe you should call off that date,” he stepped closer, trying to catch her eye in the mirror, “and stay in tonight, with me, here…”

He moved closer until his hips where against her ass.

Chelsie tensed up.

“It’ll be like old times,” he put one hand on her waist, pulling her tighter against the bulge in his pants, lewdly grinding his hard-on into her, “you know, when we spent all those nights in here, doing all those dirty things you love to do.”

His other hand began gently grazing the bare skin of her neck before lowering his mouth to her soft flesh.

“No, Derek, we can’t…fuckkkk,” she felt him against her ass and his lips on her neck, sending chills down her spine at the memory of how he used to feel against her, “be doing this. He’ll be here soon. Mmmmm,” she softly moaned out, catching herself subtly grinding against him. “I like him…”

He ran his hands over her taught stomach, up to her breasts, as he dug his cock deeper into the swell of her ass.

“I know you want this. I can feel the way your body is reacting to me.”

And he was right. Her pussy was beginning to ache for a cock – for his cock – but she wasn’t going to admit it. She made the attempt to remove his hands from her breasts, but for some reason, her hands couldn’t move that high. The way he was tweaking her sensitive nipples through her dress was driving her crazy, sending waves of pleasure directly to her hot core. His gentle kissing and biting on her neck all but caused her to melt in his arms.

“This isn’t right, Derek. We can’t…ohhhhh…” she moaned out, quickly losing control.

“Then why are you moaning like a bitch in heat?” his hand going down to her pussy, “I feel how hot you are through all of this fabric. I know that little cunt of yours wants me, no, needs me,” he hissed in her ear before rubbing over the fabric of where her clit would be.

“Oh fuckkkk!” she moaned out as his fingers made contact with her hard clit, almost sending her over the edge.

“Tell me what you want, what you need…” he hissed once again, applying more pressure to her clit.

“Shit! Fuck…I need you. I need you inside me. I need you to fuck me…” she said, totally surprising herself.

Deciding it was too late and that the line had already been crossed, she bent over, pulled her dress over her waist, revealing her soaked panties to him.

Derek quickly freed his throbbing cock before hooking her panties with a finger and guiding his hard member into the familiar confines of her tight, wet pussy. He gripped her hips before thrusting in and out of her pussy, building speed and intensity with each blow.

Her moans grew louder and louder the harder and faster he fucked her. He could feel her walls tighten up, her breathing becoming labored, just before a quick orgasm crashed through her. He wasn’t exactly concerned about her getting off as much as he was planning to dump his load inside her before taking off. He didn’t plan on sticking around all night, considering he actually had his own plans that wouldn’t involve sex.

He continued driving away at her tight pussy, using her for his complete pleasure. He could tell she was cumming but the thought never really registered with him because he simply didn’t care. Yeah, he wanted her back and all – mainly because she’s a really great fuck – but he wasn’t about to jump through all the fucking hoopla to win her over. If she wanted him back, she’d simply take him back. And up to this point, he wasn’t sure if that would be possible. But the burning question: who the fuck was she going on a date with?

“Fuck, fuck, fuck, fuck…ohhhh, fuckkkkk!” she screamed out as another orgasm hit her.

He buried his cock as deep as he possibly could before going back to pounding her tight cunt. He was close to cumming, but decided to let her enjoy her own. After all, it was happening, so why should he rob her of some pleasure for his selfish acts?

“You’re still fucking tight as ever…I’m about to fill this cunt full of cum…” he moaned out, looking up at the ceiling, as he was about to fall over the edge of complete bliss.

“Yessss!”

He slammed deep once more before unloading a massive load of cum as far in as he could possibly drive it. The intensity from the built up load in his sack just about knocked him out as it raced down his shaft and into the deepest part of her pussy. He groaned out just as loud as she did, almost collapsing on her from his orgasm. He took a moment to catch his breath before sliding out of her and doing up his pants.

“Finish getting ready, you don’t need to be late for your date,” he said as he pulled the dress back down before leaving her house.

Dazed and confused, she stumbled to her bed before collapsing on it, finally realizing what just happened. She sat up and buried her face in her hands, guilt beginning to consume her as she thought about Shane and what he’d think about her if he found out that she fucked her ex while getting ready for a date with him. She looked over at the clock.

6:49 P.M.

Oh, fuck! He came inside me!

She ran to the bathroom with a new pair of panties, quickly trying to get Derek’s cum out of her before Shane showed up. She figured she could finish up her make-up in the car, so getting rid of the evidence before it was too late was number one on her priority list for the time being. She didn’t need things to already be fucked up between the two of them. After all, like she told Derek, she likes him. Why fuck that up right away?

Okay, girl, pull yourself together. He’ll be here soon.

***

7:05 P.M.

Shane was close to her house when he received a text from Chelsie.

Ready.

Good, he thought to himself as he pulled into the driveway. He got out of his car before going inside her house to find her sitting on her bed looking like she was in deep thought.

“Hey,” he said, propping himself against frame of the doorway.

“Oh, shit! You scared me,” she said, her hand going to her chest to cover her heart.

“Oh, sorry, babe,” he chuckled before sitting down next to her and putting his arm around her shoulders. He pulled her to him before kissing the top of her head. She quickly buried her face in his chest, not letting him see the guilt that was trying to show through.

“It’s okay. Let’s go eat, I’m starving.”

“Me too.” He got up before taking her hand, lacing his fingers with hers, and walking out to his car. She kind of seemed distant, but maybe she was just tired from work?

The drive to The Olive Garden was quiet to say the least. He was beginning to feel a bit concerned by this because she usually was the one talking. He tried to make small talk with her, but her answers were short and she kept avoiding his eyes. Most of her attention happened to be focused out the window or anywhere but Shane.

“Babe, what’s wrong?” he asked as he tried to take her hand.

“Nothing,” she shot back, closing herself off some more, “I’m fine.”

“You don’t seem fine,” he said before tickling her thigh just above the knee.

She screamed and jumped before grabbing his hand, laughing at the way he surprised her.

“Babe! Stop that!” She grabbed his hand and held on to it. It’ll be okay, it was just a stupid mistake. Calm down and get over it, enjoy yourself.

That’s when she began to open up and actually participate in the conversation without acting like her dog was run over. She was more playful, more vibrant, the further away she got from the memory of what happened with Derek. She figured she could suppress that image and forget about it for the time being. But if she was actually going to be with Shane, she had to eventually tell him about it. She just didn’t know when or how to do it.

***

Dinner went well. The food was great and, with more and more alcohol being consumed, the more playful the two were. Throughout dinner, Chelsie kept rubbing her bare foot over the crotch of Shane’s jeans, especially while he was trying to order. As the night progressed, the more bold and daring she became with her little game.

She could feel everything against her foot and that made her want it that much more. Fuck everything else for the night – she just wanted him to fuck her. She didn’t care if he had anything else planned; she was going to get what she wanted. She was going to make sure he took her back to wherever they were going to end the night.

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She wanted to be there, with him, and have him fuck her like he did a couple days prior.

He couldn’t pay the bill fast enough. He wanted it just as bad as she did. After all, she was the one teasing him like that. He planned to make her pay for what she had done.

***

Shane slid the key into the lock and quickly turned it, opening the door to his apartment. He pushed the door open and waited for Chelsie to enter before stepping in behind her and closing the door. She pushed him against the door before locking her lips tightly to his, running her hands through his hair. She wanted him bad – no,...

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