From Across the Bar

Dennis could see her from across the crowded room. People shuffling through the middle of the club passing through his line of sight, but he kept his eyes on her. She had shorter hair, about shoulder length as black as night. It contrasted heavily with her pale skin that seemed to reflect every color the club's LEDs projectors. She was thin with very small boobs and her shorts sat just below her exposed bellybutton. She sat alone at the bar, staring forward. Dennis was never one to approach girls on his own, but after his recent breakup he knew that he had to put himself out there once again.

Dennis walked across the room and stood next to her. Looking straight towards the hundreds of illuminated bottles behind the bartender Dennis spoke up. "I saw you from across the room..."

"Did you, now?" The woman responded with disinterest.

Dennis knew he didn't have the best moves, but he knew he had to try something, she was just too good looking to let get away. "Yeah, I thought 'there is a girl who needs to get hit on tonight' so here I am." Humour was his only way of making an impression.

"Listen dude, you're not going to sleep with me tonight." She responded with a bit of ice in her voice.

"Tonight? So, you're saying it will happen some other time? I'm cool with that. What are you drinking? I'm buying." Replied Dennis with a smirk.

Finally, she turned to face Dennis, and he did the same. She looked young, perhaps mid 20s Dennis thought. Her eyes were a hazel green, and they were scanning him up and down.

"I'll take a white Russian." She finally said, this time with some emotion in her voice.

"I think I have a little Russian in me, and well, as for the white." Dennis gestured to point out his body.

The woman let out a small giggle and looked down to hide her grin. "You're funny, I will give you that."

Dennis responded. "Well, I'm not smart cool hot or hung so I needed to pick up the slack somewhere."

The bartender came up to Dennis and asked what he wanted to drink.

"I'll have a jack and coke, and the lady will have a white Russian." Said Dennis to the Bartender

The bartender gave a look with his eyes that Dennis couldn't quite decipher and left to get the two their drinks.

"So, are you from the city?" Dennis asked.

"No, just moved here actually. This club is about the only place I have found so far. Been here every night." Said the woman with a bit of self-pity in her voice.

"Oh well allow me to welcome you to town. I would offer my tour services but unfortunately those are pretty expensive for someone who can't buy their own drinks." Dennis said with a smirk.

She shot back. "I can buy my own drinks; I just don't know why I would when I could get them from horny guys all night."

"Touché" Responded Dennis

Just then the bartender returned with their drinks.

"I propose a toast! To... new beginnings?" Dennis said raising his glass slightly.

The two clinked their glasses together and took a sip.

"What's yours?" The woman asked.

"What's my what?" Dennis asked in turn.

"Your new beginning, you gave it a plural." She spoke.

"Oh... Yeah. I uh... I just got out of a long relationship. Was too good in bed." Dennis proclaimed with a faux pride.

"Well, I could see why that would be an issue for some." She said once again trying to hide a grin. "Listen, I don't think you actually want to sleep with me. In fact, I am sure you don't want to sleep with me." She said to Dennis in a somewhat dejected tone.

"Okay, I will make you a deal, alright? We sleep together, and then I will tell you afterwards if I wanted to now or not. That way we both win! You get confirmation one way or the other, and I get to have sex tonight. Deal?" Dennis thought he might have gone overboard with that one but kept his hopes up.

The woman thought for a moment, once again looking Dennis up and down. "You know what... fine. But when I am proven right, you need to buy me drinks for the rest of the week."

"I wouldn't have it any other way." Dennis responded coolly.

"My apartment is actually above this place; we can go there. Let's finish our drinks and we can head up to prove you wrong." She said to Dennis.

After drinks the two sat in her apartment. The landlord clearly furnished it, but it was very nice. Dennis guessed that her rent was a few thousand a month, and he wondered how she paid for it.

"You know... we never actually exchanged names." Stated Dennis from the couch as she mixed another drink at the kitchen counter.

"Lizzy, you?" she said.

"Dennis, like Dennis Quaid, minus the cocaine." Answered Dennis.

Lizzy walked over to the couch with her drink in hand and sat down next to Dennis.

"Nothing for me?" Said Dennis feigning disappointment

"Nope, I am not letting alcohol's judgement get in the way of my drinks. I am intent on winning this." Lizzy said before taking a sip of her own drink.

"So why do you think I won't want to sleep with you." Asked Dennis.

"How about we find out." Lizzy said as she put down her drink. She leaned in to kiss him.

Her lips were soft, and her tongue moved fluidly around his. Her breath smelled like alcohol and cherries. Dennis put his hand on her back and moved it down slowly towards her ass as they made out.

Dennis pulled back for a moment. "You know, this isn't helping your case."

"Oh, I beg to differ." Lizzy said before pressing her face against his once again.

After a few minutes of making out and feeling each other's bodies the two made their way to Lizzy's bedroom. She had white sheets on a queen size bed in the center of the room. The window covered the entire wall off to the right when they walked in and it overlooked much of the downtown area.

"Lie down on the bed and get your clothes off. I will be right back." Lizzy said forcefully before walking into the closet to the left of the bed.

Dennis stripped down and laid down on the bed. His throbbing erection pointing straight to the ceiling. He couldn't believe that she thought he wouldn't have sex with her. He was ready to fuck until the sun came up.

Lizzy came out of the closet wearing a set of red lingerie. Her lacy bra was hardly filled out but was still very enticing, and her hips were fairly narrow. Her legs, long and pale. Her belly just as pale but firm. She walked to the foot of the bed and faced Dennis.

"So... why did you think I wouldn't want to have sex with you?" Dennis asked in earnest.

"This." Lizzy pulled her panties all the way to her feet and as she rose back up, she shimmied her legs and hips.

From between her legs untucked a penis thick and long pointing straight towards Dennis on the bed.

Dennis couldn't believe his eyes. It was like one out of a porno. The skinny woman in front of him had a cock significantly bigger than his own. Dennis looked up and down Lizzy's body, hoping that maybe she was playing a prank on him, and it was actually just a realistic dildo but there was nothing holding it on.

Lizzy looked at Dennis now sitting up on the bed dumbfounded. "So, you still want to sleep with me?" She said with a smirk.

Dennis's mind went blank. He still couldn't believe what he was seeing. As the question swirled around his head, he tried to form words, but nothing came to mind. He could only stare at the monster pointing at him from a few feet away.

"I will take that as a no. Good, I am getting thirsty." Lizzy said as she turned away.

Once Lizzy turned Dennis came back to earth and able to form just one word. "Ye- yes."

Lizzy turned around in shock. "Did this guy just say yes?" She thought. Lizzy couldn't believe that Dennis wasn't instantly turned away by her penis.

"Yes... I do... I mean I think I do. A hole's a hole of course, and I can't exactly afford too many drinks." Dennis said once again staring at Lizzy's monster. He guessed it was eight, maybe nine inches long, and about six inches around.

Lizzy was not counting on him still being up for it and had to think quickly. "Oh... well, who said you would be the one doing the fucking?" Lizzy said with confidence she had him now.

Dennis shot his head back and looked her in the eyes. "Well... I... I have never... and it wouldn't fit... so that's hardly fair." Dennis was able to stammer out.

"A deal is a deal; you don't want to have sex with me and that is how I have sex. So, I guess I will be drinking a lot this week" Lizzy said smiling mischievously. She knew she had him.

"Fine. But we will go at my pace." Dennis said with a sudden burst of confidence. He couldn't risk losing this bet.

Lizzy's jaw dropped as the two traded places of who was more shocked.

Dennis couldn't believe the words that had just come out of this mouth. He had never even put a finger up his own ass, let alone an eight inch penis.

"And you're sure you want to do this?" said Lizzy genuinely. "I am distinctly asking for your consent here."

Dennis looked at Lizzy up and down. She was quite striking, ignoring her large penis. "Well, I have heard pegging feels good and this isn't too far off." Thought Dennis.

"I want to do this." Said Dennis out loud, finally.

"Alright." Lizzy smirked. "Get down on your knees."

Slowly, Dennis stood up from the bed and lowered himself, so he was face level with Lizzy's penis. He grabbed it with his right hand.

Dennis felt a flutter in his torso the second he touched Lizzy's warm shaft. Though his inhibitions screamed at him a part of it felt right. Dennis left his hand idle on the shaft, feeling her heartbeat pulse quickly through the erection. He moved his mouth to the head and licked the tip of the cock, finally engulfing the head as best he could.

Dennis's jaw stretched wide, almost painfully as to prevent his teeth digging into the enormous organ. He began to taste a slight pleasant saltiness as the precum began to extrude from the tip.

Lizzy, growing somewhat impatient lightly pushed Dennis's head further down her member until she heard him gag, which caused him to recoil backwards.

"Give me a break, I've never done this before!" Pleaded Dennis through watery eyes.

"It seems like you're not even doing it now. Listen, if you want to stop, I won't be upset." Replied Lizzy, a clear sense of frustration in her tone. "But you'd have lost the bet."

Without a word, Dennis put the penis back in his mouth, this time pushing it further into the back. After a few strokes in and out he seemed to relax a bit and the motion was no longer difficult. Though, when he tried to push it into his throat, he was met with way too much resistance.

Dennis pulled his throat back and began stroking the cock quickly with his hand, using his spit as lubrication. Lizzy shot her head back and let out a sharp groan. From his own experience on the receiving end, Dennis knew how effective this tactic was. He wished he could be receiving it now.

After a few cycles between his mouth and his hand Lizzy put her hand on his head and pushed him as far as he could go. Though she was disappointed when Dennis's throat didn't give way to her thick rod. When Dennis pulled his head back to get some air, she looked down at him. "Well, I suppose I can't knock you for not going deeper, you just can't."

"Yeah, that's what happens when someone has never done this before." Said Dennis a little frustratedly.

"Well, I won't put you through any more of this." Replied Lizzy.

Dennis looked up excitedly. "Oh, so I win!"

Lizzy gave a little chuckle. "Win? Oh, honey. You still have a lot more to do. Now get on your back."

The light left from Dennis's eyes. He knew that this was coming, but he half expected to have gotten out on some kind of technicality by now, or he had at least hoped. Without a word he got onto the bed and laid down on his back. To his surprise his own penis was still erect and pointing straight upward.

Lizzy took notice immediately. "Seems you enjoyed yourself more than you're letting on."

Dennis couldn't believe what he was seeing. Was he really enjoying this? Was his subconscious not in line with his conscious?

While Dennis pondered his own sexuality, Lizzy went around the bed to her night table and pulled out a small bottle of lube. She put some onto her cock and began to spread it around while walking back to Dennis waiting on the edge of the bed. "Okay, legs up, and just try to relax. This can feel really good if you let it." She said, almost comfortingly.

Dennis put his legs up and closed his eyes. He could feel Lizzy's finger explore his hole adding some lube. Then he could feel the tip of her cock pressing in. Dennis did his best to relax and, in that moment, he felt it slip in.

Every nerve in Dennis's body fired. Most screaming that something was wrong, but a few telling him that this was exhilarating. As Lizzy slowly pushed deeper Dennis scrunched his face as he could feel himself quickly filling up. As Lizzy pulled back Dennis felt an all too familiar feeling that he'd have rather not thought of in that moment. Dennis finally opened his eyes to look at Lizzy. He really did think she was quite beautiful. She had a thin but well defined face. Her dark hair reached her shoulders and framed her face well. His eyes went down her arms and he noticed her arms were long and thin with thin but dark hair. Her hands holding his legs up were slender. Besides the monster between her legs, Lizzy was the definition of Dennis's perfect woman.

After a while of slow thrusts Lizzy began to go a little bit faster and quite a bit deeper. The first deep thrust coaxed a moan from Dennis. A mix of pain and pleasure evident in the tone.

Lizzy slowed and stopped to grab the lube once again, this time applying it to Dennis's own rock hard cock. The sensation of her deft hand twisting around his head, and the large cock inside of him was mind-blowing. Dennis threw his head back and let out a long groan of pure pleasure.

Lizzy took this as an invitation and began to thrust even deeper and faster. Dennis could no longer contain his moans with every thrust. Every muscle in his body had gone limp, his body seemingly melting into the bed as Lizzy continued to pump aggressively into him.

After what seemed like a millennium to Dennis he felt a familiar feeling in his groin, yet somehow deeper. Dennis realized he was about to orgasm, but he couldn't come up with the words. "I- I'm g-" was all he could stammer out.

Lizzy continued to thrust and stroke at the same pace. "Yeah? Yeah, you're gonna cum for me? I want you to cum for me, I want you to cum all over."

As Lizzy continued her dominant encouragement Dennis felt seemingly every nerve in his body fire. Most of his muscles suddenly tensed and finally he reached his peak. His orgasm was powerful, and Dennis began to see stars. He could feel the cum all the way through his dick and then when it landed on him. Through the pleasure he could feel a warm burst land on his torso, face, and arms.

As he came down from his ecstasy Dennis noticed the room seeming to spin around him. Every feeling from before was now intensified tenfold and he once again couldn't help but moan repeatedly from the pounding he was receiving.

Shortly after his own orgasm, Lizzy began to breath very heavily and speed up her thrusts. Dennis felt too weak to respond in any way, his mind couldn't even come up with any words. He could feel the cock inside of him expand even further.

With a few more deep thrusts Lizzy finally began to unleash inside of Dennis. He could feel every spurt fill him more as she pushed as deep as she could get. Lizzy stayed mostly silent though.

When her orgasm was over her grip on Dennis's legs loosened and she slowly pulled her now softening cock from inside of him. Lizzy slumped forward onto the bed and slid next to Dennis. She began to lick his cum off of his chest and neck.

The two were spent, and they laid wordlessly for a few minutes, breathing heavily.

Finally, Dennis turned his head to look at Lizzy. "Okay. Now, I won."