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Chelsie's Dilemma - Part 2

Does Shane give in after a series of guilt trips?
What the fuck was I thinking last night?

Shane was upset with himself for the way he ended his night. In his inebriated stupor, he decided not to have sex with Chelsie in fear of things moving too quickly with her. But after several trips down memory lane, he began kicking himself for not doing it.

“Are you fucking stupid?” Derek asked after he was informed that he didn’t sleep with her.

“Shut up, man. I already feel like a dumbass as it is,” Shane replied, looking away as he shook his head.

“She was DTF – down to fuck – and you passed it up, why?”

“Because I didn’t want to press the issue and make things awkward between us. I should’ve just done it because she’s been guilt tripping me all fucking day.”

“We’ll chalk this one up to a very poor life decision if you don’t fuck her ASAP!”

“Yeah, yeah, yeah, don’t worry…I’ll get this shit taken care of.”

Shane and Chelsie were sitting at their table drinking and chatting for some time before she became bold and decided to invite him over to her place for another drink.

“I’m not really a fan of a smokey bar,” she said after asking him over.

“Yeah, same here. I’d prefer to be elsewhere,” he said with a smile before getting up and taking her hand. “Do you just want me to follow you?”

“How else would you know where to go to get to my house?” She answered him sarcastically as they walked towards the parking lot.

“Okay, smartass, I’ll just follow you then,” he laughed before playfully swatting her ass, causing her to jump and let out a tiny scream from the unexpected slap.

“Better to be a smartass than a dumbass!” She sang, making sure to jump out of the way as his hand came back for another slap to her ass. He missed.

“You’re gonna get it!” He laughed as he began chasing her towards her car. He caught up to her just as reached the door. Grabbing her sides, he began tickling her before she spun around in his arms and faced him, her face a couple inches from his. They stopped and looked each other in the eyes, her in his embrace, before he slowly leaned in and placed his lips against hers.

She was slightly stunned, unsure of what exactly to do, before kissing him back. Her arms went to his neck, wrapping around him, locking her fingers, as the kiss grew deeper and more sensual. They kissed like it was something they’ve done before, like only two lovers would know how. The kiss made her lose sense of her surroundings. She forgot they were by her car until someone let out a whistle that distracted both of them.

“Wow…” she whispered after they broke the kiss.

“Damn,” was his subtle reply before leaning in to kiss her again.

“My house…” she reluctantly pulled away before getting into her car.

He quickly ran to his car before following hers to her house. He didn’t want to stay long because he knew he’d end up fucking her and that wasn’t his intentions for the night. He decided to be the nice guy for once, to see if this approach might land a relationship, but would he actually be able to leave the situation if she were begging for it?

No, no, no, it’s not gonna happen. I’m gonna have one drink with her then leave. That’s it…

And that’s exactly what he did. Not even the passionate kiss was enough to deter him from the barriers he set for himself that night. He wanted to be there with her, to be inside her, but he also didn’t want to rush things. He didn’t want her to be another notch on his belt-of-fame – as his friends so kindly referred to it as – but rather someone who could potentially be girlfriend material. He didn’t want to risk fucking everything up for a night of alcohol-induced sex.

Even in the midst of his pleading with her, she didn’t relent. She knew what she wanted and she was more than determined to get it, even if that meant completely throwing herself at him.

“Babe, let’s not do this just yet…” he tried to reason with her, but she was still persistent.

“You know you want me, you know you need me…” she hissed in his ear before trapping his ear lobe in the warm, wet space of her mouth, before gently biting down and then pulling away.

Chills swept through his body as his cock became achingly hard in his pants. There was no denying he wanted her. All anyone had to do was look at the painfully obvious evidence that presented itself in his pants. The denim of his jeans began to feel like a tightly enclosed prison for his cock, threatening to cause severe claustrophobia if he didn’t release it right away. But that would mean giving her an opening to completely destroy the defenses that were beginning to crumble as it was.

“Not gonna lie, I do, but I don’t think we should do this just yet,” he replied before meeting her eyes.

“Mmmm, how did the nice guy make it to my bed then? Usually he kisses me goodnight at the doorway and then goes on home. That’s a call I usually don’t answer the second time,” she bluffed, hoping it would cause Shane to break and give her what they both wanted.

“Well then,” he stood up, “that’s a chance I’m just gonna have to take,” he finished up with a kiss to her lips. “Goodnight, Chelsie.” And out of her room and house he went, painful erection in tow.


Chelsie woke up still feeling somewhat bitter and pissed about what happened the night before. She didn’t get to have sex and didn’t get to finish masturbating because her friend rudely interrupted her session with a text describing the kind of night that involved a gang bang. She tried playing that morning but, for some reason, it just wasn’t working out. She kept digging her fingers as deep as she could inside her pussy but, still, nothing.

“Fuck this,” she said before getting up and getting ready for work.

Work. What a fucking joke that was. She was in a pissy mood all day and it didn’t help matters, at all, when Shelby walked in. Her friend had a slight limp and seemed a bit uncomfortable, but she still sported a happy, satisfied smile. You know, like she had been fucked the night before. Chelsie wanted nothing more than to just punch her right in her man pleaser.

Chelsie had no interest in talking to Shelby. She knew the conversation would be based around their respective nights and she had no desire to hear about the raunchy debauchery that her slutty friend took part in. She knew Shelby would ask her if she got some and that wasn’t a question she wanting to deal with – at all.

All three of her failed attempts of getting off were really starting to get to her. The aching need deep in her loins was beginning to annoy – no, more like really piss her off – her as the day progressed. She couldn’t think of anything but Shane bending her over the counter and fucking her hard from behind while the customers came and went throughout the day. She wanted so badly to run off to the bathroom and see if she could possibly settle her flaming need, but she knew she wouldn’t be able to keep quiet, so she finally decided to suck it up and deal with it until she got home.

I hope you’re working today, – her phone read after she finished clearing one of her tables.

Why yes, yes I am, – she replied before going back to her work.

See ya in a bit.

Hmm, that’s a bit strange…


Hopefully I don’t fuck this up.

Shane carefully laid the flowers on the kitchen table with a note before laying down on the bed. He kicked off his shoes, stretched out and waited. He wasn’t really sure what he was waiting for, but he knew the patience would pay off – well, hopefully. He didn’t know what her reaction would be to finding him sprawled out on her bed when she arrived home from work, but that was a chance he was more than willing to take. Was she going to yell at him and make him leave her house? Or would she jump his bones like so many of the texts from that day had inclined? All he knew: there’s only one way to find out.


Confusion began to set in as she noticed the flowers sitting on top of her kitchen table. She slowly moved towards the table before noticing a note had been placed under the stems of the flowers. A warm smile spread across her face as she read what the note said.

I’m sure you’re slightly surprised to see flowers sitting on your table, but it was the least I could do after what happened last night. I shouldn’t have left you like that, given our current state, but I felt like things didn’t need to move that fast. I like you a lot and, depending on how you feel about me, I’d love to be with you. Give it some thought. In the meantime, there’s a surprise waiting for you on your bed.

Chelsie dropped the note before running to her room. She opened the door and found Shane asleep on her bed.

“No. Fucking. Way…” she said, waking him from his sleep.

“Oh…hey…” he replied with a sleepy smile as she walked to her bed.

“How long have you been here?”

“Like an hour, I think.” He sat up before giving her a kiss.

“Oh okay. Where’s your car?” She asked, realizing that she didn’t see his car out front when she pulled up.

“It’s down the street. I didn’t want you to know I was here until you found the flowers and note.”

“I saw them as soon as I walked in,” she said with a smile before returning the kiss.

He pulled her tighter to him, wrapping his arms around her back, as the kiss grew deeper and more sensual. His hands began rubbing her back, causing her breathing to deepen. She pressed herself tighter against him before breaking the kiss.

“I’ve been thinking about this all day,” she cooed before kissing him again.

“Thinking about what?”

“This…” she moved her hand down to his cock that was very quickly inflating. “I’ve been wanting this since last night.”

“Hmmm, no wonder you kept throwing those racy texts at me earlier. But, if you want it, take it…” he looked into her eyes, trying his best to portray the huge amount of lust he was feeling at the moment.


She began to undo his pants to free his cock. She never really got a good look at it the night before since he was so quick to leave, so she was definitely adamant in her efforts to actually make this happen this time. Her needs were evident throughout the day – just take a look at her panties – and she was willing to do whatever it took to make sure her needs were thoroughly taken care of. Even if that meant forcing him to fuck her.

She slowly stroked his cock as he moved to kiss her neck, eliciting small moans as he bit down on her soft flesh, causing her to squeeze his cock tighter and tighter with every stroke. His hands went to her breasts, cupping and squeezing them, before pushing her shirt up and out of the way. She let go of his cock before quickly removing her shirt, giving him complete access to her lace-covered breasts.

He expertly reached behind her and un-hooked her bra with one hand, his other hand busy with the button on her pants. All actions seized as her pert breasts were finally upon his gaze. He couldn’t quite believe he was finally staring at her naked chest, something he’d been visualizing for the past few weeks, but the reality in front of him was rather difficult to deny. His hands began roaming her breasts, giving him the concrete evidence that this was actually happening, before his mental lapse of what to do next could take over and make the whole situation awkward – and that definitely was not in his plans for the day.

He slowly – and carefully – took a nipple in his mouth and began rolling it with his tongue before gently biting down and sucking on it.

“Oh, fuck, baby,” she gasped as he switched to the other nipple. “That feels so fucking good…”

He shot her a quick grin before sucking a little harder on her nipples that were hard as a rock, making her moans increase in volume.


He discontinued the suction of her nipples before kissing down her toned stomach. He could feel her breaths shortening, her stomach flexing, as he got closer and closer to the line of her waist. He smiled to himself with every kiss, knowing she was becoming pretty anxious for him to touch her in one way or another. He thought about teasing her, but what exactly would that accomplish? He wasn’t sure if she was the kind of girl to take kindly to subtle teasing, or if she relished in it. He could risk everything and find out, but why? He needed her just as bad as she needed him, so why torture himself in the process?

He fumbled with the snap on her pants – probably out of nervousness, if anything – before getting them open and off her ass, exposing the soaked barrier that separated him from pure bliss. His prize was beneath the flimsy piece of material that was already beyond soaked from the series of events that had already taken place. He hungrily licked his lips before slowly, teasingly peeling away the frail fabric, completely exposing her labia to his gazing eyes and allowing the cool air of the room to sweep across her wet, open lips. She sighed as she felt the contrasting differences from the sudden exposure her pussy had received.

He ran his finger up and down her wet lips before coming to rest on her protruding clit. He slowly began circling her hard button, applying more pressure as she started squirming below him. She hadn’t been touched by anyone but herself in over and three months and the new sensation wasn’t something she was used to. It felt much better having him play with her clit than it was for her to do it herself. She quickly felt an orgasm build before it released with a fury, causing his jaw to hit the bed as he realized what had happened.

“Damn, that was quick…” he said, looking at the rush of liquid that came from her pussy.

“I haven’t been touched by another man since the ex,” she replied, breathing deeply between words as she began to come down from her orgasmic high.

“Ah, that makes sense,” he shrugged before lowering his mouth over her pussy and pushing his tongue inside her, tasting her leaking juices before he began to eat her little pussy.

“Oohhhhh, fuckkkk!” she screamed out as her hands shot to his head, gripping his hair as she pulled him tighter to her dripping cunt.

He tongued her for all he was worth, making sure he used every bit of his tongue that he could while she continued to moan and buck her hips against his face. He wriggled his tongue inside her tight pussy as best he could, he hands going to her ass to pull her box closer to his open mouth.

The more his tongue worked her pussy, the tighter her grip on his head became. Her writhing became more violent, her moans turned to screams, as another orgasm threatened to consume her once again. He could feel it approaching, which only sped up his efforts to make sure she got off a second time. He began sucking on her lips while his right hand went to her boobs to manipulate her hard nipples. In just a matter of moments and she came all over his face while he made the attempt to take in whatever she had to offer to his open, eager mouth.

“Ahhhhhhh!” she screamed, her orgasm hitting her full force. “Fuck!”

He kept at her pussy, making her scream more and more, before she finally pushed him away. Her screams softened to moans as her she regained control of her own breathing, her orgasm still going on and on.

“Holy shit…” she fell limp, legs still wide open, before she felt Shane lie on top of her. He kissed her lips, letting her taste herself, as he slid his full length deep inside her tight, wet pussy. “Oh, fuckkkkkkkk.”

“Damn, girl…” he whispered in her ear as he slowly slid in and out, going as deep as he possibly could.


“You’re fucking tighhhtttt…” he moaned into her ear as he began thrusting harder and faster.

“Oh, fuck…I’m tight for you. Ohhhhhhh…”

He didn’t say a word. He slammed as deep as he could, eliciting scream after scream as he fucked her hard. Every thrust grew with intensity, with passion, as the two really began getting into it. She met him thrust for thrust, doing her best to look him in the eye while he took her hard and deep. There was no way she was going to ever get used to what he was doing to her. His cock continued to pound away at her deepest depths.

He could feel every muscle tighten around his hard cock as he sawed in and out of her tight canal. Every ridge and smooth area became more vivid and enhanced the tighter she squeezed him. He could sense an orgasm was approaching – her moans and breathing was kind of an indicator – so he really ramped up his efforts. He began plowing into her hard, giving her every inch of his throbbing cock, willing the girl beneath him to cum all over him.

“Oh my…I’m gonna cum! Fuckkkk, I’m cummingggggg!” she screamed out as the force of her orgasm crashed through her body, almost forcing his cock from her tight cunt.

“Oh fuck…” he slowed down a bit, doing his best to prolong the inevitable from happening.

“You are gonna cum inside me. You know this, right?”

“Is that so?”

“Mmhmm, I’m gonna get all of your cum deep inside my tight, little pussy…”

“Fuckkkkk…” he lost it.

He lifted her legs up as high as her body would physically allow before fucking her as hard as he could. She wanted his cum. Who was he to argue with her over that?

Wait a second. The first time should be a little longer than this. I’ll cum inside you, but not just yet…

“What are you doing?” she asked as he pulled out of her pussy.

“Hands and knees,” he ordered while waiting for her to comply.


It was her favorite position. She loved to feel a cock deep inside her while she was being taken from behind. She didn’t know just how deep a cock could go until her ex fucked her like that for the first time. The position definitely was a guaranteed way to make her flood his cock.

He moved in behind her before working his cock back inside her, stretching her open as he thrust deep and hard. They began moving together, her hips coming back as he thrust forward. They seemed to have some sort of chemistry in bed and Shane took this as hope of things to come. If they were already this compatible, how would everything else be?

With his left hand on her left hip and his right hand tangling itself with her hair, he began roughly pounding her pussy from behind, both of them moaning out from the onslaught of cock she was receiving. Thrust after thrust of his cock slamming away inside her, her moans ringing out, the slapping of their skin coming together was almost too much for him. He didn’t exactly care though. He knew where his cum was going to be deposited. It was just up to him to make that happen whenever he so chose to.

He loved the way her pussy gripped him as he fucked her hard. Every contour of her pussy came to life as she moaned out. She came over and over again before he decided she finally had enough. It wasn’t until she began begging for his cum when he decided she could finally have it.

“Please fill me up, Shane. I need to feel your hot seed deep inside my pussy. Don’t you want to see your cum leaking from my well fucked hole?”

Yep. That was all the coaxing he needed. A few thrusts later and he were dumping the contents of his sack deep inside the wanton pussy in front of him, grunting and jerking along the way. Her pussy continued to squeeze the life out of his cock, milking the cum from his spent sack, before he pulled out. His cock was super sensitive and couldn’t take much more.

“Fuck, that was amazing…” she sighed as he collapsed next to her.

“Yeah, no joke…”

He pulled her to him and they began to cuddle. He wrapped his arms tightly around her, kissed her forehead, before closing his eyes. Together, they both drifted off to sleep, tightly entwined in a web of arms and legs that bared no clothing whatsoever.


May 10 th , 2011

Holy shit, that was fucking amazing. Shane just left, but I can still feel his cum oozing from my pussy. I haven’t been fucked like this in God knows when. We slept for about an hour or so before waking up and going at it again. I rode his cock, he fucked me from behind again and even fucked me up against the wall. I’m thoroughly exhausted and satisfied. I’m more than happy that he was here to surprise me the way he did.

But now what? I wasn’t expecting Derek to randomly drop by. God, he always does this shit to me! It’s like he knows that some other guy is making his way into my life and he just happens to drop by my work in an attempt to sabotage EVERYTHING. It wouldn’t be so bad, but he keeps telling me he loves me, how we need to be back together, how we’re perfect for one another.

See, I’m not even sure if they even know each other.

Whatever. He just wants to fuck me again before going on his merry little way. At least that’s what I think he wants. I don’t know, he seemed pretty sincere this time. I just hope it’s not one of his little games. I really don’t think I can handle another round of that.

This sucks. I don’t know what to do about Shane and Derek. I still have some feelings for Derek, but I’m really starting to like Shane now. Ugh! I’ll just have to sleep on it and go from there.

We’ll talk later.
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