The Look

Story Info
A chance meeting on the road turns into a wild night.
6.5k words
4.37
50.5k
14
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I walked through the doorway to the hotel bar and began scanning the crowd. I was curious to see how the local talent was shaping up tonight. My left hand began to itch, specifically my left ring finger, so I idly scratched the pale band at the base as I let my gaze slide across the room.

I took a couple of steps into the darkened bar, glanced at the rectangular shaped bar in the middle of the main room, the stopped and stared. What immediately sprang to mind was the lyrics from the Jimmy Buffett song, "There she sat at the corner of the bar/As I broke another string on my old guitar/Someone call a cab/Lady won't you pay my tab?"

She was a short redhead, five-foot-nothing, wearing a little more makeup than I tended to prefer, but she had the kind of rack I've always liked and a body that carried it well. There was one other thing she had that really caught my attention. She had what I've always referred to as The Look.

The Look isn't something that you can necessarily describe in specific words. The Look certainly involves looking good, but there's that indefinable something she just has to have. For starters, women with The Look tend to be a little bit older. Young hotties can look good, but they haven't had enough time to develop the proper attitude that always accompanies The Look.

Women with The Look Know Who They Are, and Like It.

Women with The Look are Confident and Know Exactly What They Want, and Won't Settle for Less.

Women with The Look Aren't Necessarily Shopping Around, but When They Find It, They Make Sure They Get It.

Most guys don't truly understand what The Look is all about. From my experience, women with The Look tend to intimidate men who instinctively head the other direction. The biggest part of The Look is the fact that you'd better bring your A-Game. Even the hint that you might even have the possibility of a B-Game is enough to have women with The Look leaving tire tracks on your torso as they head down the road, not even looking in the rearview mirror at your mangled body.

What they really don't get is the fact that women with The Look are worth all the effort required. You can have all the young hotties -- they're a dime a dozen. You manage to get yourself a woman with The Look and you have something that will leave you gasping and breathless. They're so above the rest of the females in the fray that looking for anything less means you're cheating yourself of an experience you'll never forget.

That's a lot of words trying to quantify something that's basically undefinable. But like the Supreme Court justice said in a ruling, you know it when you see it.

She had it. Oh, yeah, she had The Look, in spades. I felt my pulse pick up, and a stirring in my gut, and a little bit lower as well. The Look always gets me going. And this time, it got me going toward the corner of the bar, even if I didn't have an old guitar as an icebreaker.

I had taken two steps, and then started cursing myself for my hesitation as I'd walked into the room. A tall guy with a goatee sidled up next to her as she was finishing off her beer. It was obvious he was getting ready to buy her next drink.

But then she did something curious. She turned toward him, and you could tell she was saying him no thanks. He persisted, said something that he obviously thought was clever, and then waited confidently for a response from her.

She looked at him, shook her head at him again, and when he looked confused at her response, she said a short phrase of some kind. With that, his eyebrows went up and he scuttled off as quickly as he could. You could almost smell the scorched flesh from whatever she'd told him. Whoa.

I smiled and walked toward her. I figured, what the hell, what did I have to lose? As I approached her, I said, "You look like you're ready for another one. My treat."

She looked up, and instead of the blank stare she gave the other guy, the redhead smiled at me. "It all depends," she said. "Are you a lying sack of shit?"

How the hell do you answer that? "I do my very best not to be." I paused then added, "Miller Lite, right?"

The redhead nodded. I smiled at her, and she smiled back. "Hi, I'm Steve."

"I'm Anna." I sat down on the seat to her right, and gave the bartender the order for two beers. "You sure you're not one of those guys who's a lying sack of shit?"

"Pretty sure. Been having problems with that type lately, huh?"

The beers showed up, and I handed her one of the bottles. As she took it from me, she glanced at my left ring finger and saw the pale band. Her eyes widened just a bit. That's when I looked at her left hand. There it was -- that same pale band. Interesting.

She smiled. "Matter of fact I have. You see that guy that just came up to me?" I nodded. "He used a really tired, standard pickup line. I asked him how limber he was. That stopped him cold. Then I told him to go fuck himself."

"At least you got rid of him quickly," I said. "Any suggestions for me?"

She gave me a smile. "Yeah. Let's move to one of those open booths."

"Sounds good to me." We picked up our beers and strolled over to a corner and sat down. "At the risk of sounding lame, I haven't seen you here before. I sure would have remembered that."

She gave a little chuckle. "I'm from out of town. Work sent me here for to take some classes. If I want to get promoted, or get a raise, you have to take these two and three day seminars. They're kinda boring, but it's nice to get away every once in a while. Gives me a chance to relax, or even party a little bit."

"Well, I have to warn you, I'm actually a professional bullshit artist, so be warned."

"Nice." She took a sip of beer. "I can tell. At least you're an honest bullshit artist. That last guy looked like a real weasel."

"Let's just say I approve of your judgment. I'll do my best to live up to it," I said, laughing. Then I took my own slug of beer. I asked her what she did, and she began telling me about her job, throwing in stories about crazy customers and the like.

I loved watching her as she talked. She had a pleasant voice, and a wry way of saying things. Being in a corner booth had its pluses. We weren't sitting across from each other -- instead we were side-to-side, and since I'm rather hard of hearing, I had to slide over a bit, and lean over to hear what she was saying. I tried to concentrate on looking her in the eye, but it was hard since she was wearing a top that was slightly unbuttoned and showed some cleavage. Nice cleavage, too.

I responded with my own work-type stories, and the whack jobs I'd run into on the road over the years. I got her laughing, and she had her own stories. Playing "Can You Top This" with her was fun. Almost as much fun as another variant of the game would be.

The bar was kind of quiet, a little bit dead, but like usual, they had the music playing too loud. Fine with me -- another excuse to get a little closer to hear what she was saying. I had to get up to get our refills, since apparently they'd sent the waitress home. I have to admit I was checking her out pretty good, and after a couple of brews, not only I was getting a little bit interested, it was showing. I think she caught me looking down her shirt a couple of times, but didn't say anything. On the contrary, I caught her checking me out the second time I got up to get refills on the beer.

When I came back with the beer that last time, I handed it to her, and I swear a little spark of electricity hit both our hands. Love cheap carpets in bars. She let out a little "whoa." The smart-ass line was uttered before I could even think about it. "We definitely made a connection there. Must be fate"

"Don't get ahead of yourself, big boy," she said. But she patted my hand when she said it. Voluntary contact. And it felt pretty damned good. Another of those little ice-breakers. Very nice. And then I noticed we were sitting even closer together, almost touching.

We continued talking, but the stories were getting a little more personal. I asked her what kind of music she liked, etc. etc. etc. As we were finishing our third beer, the dreaded Call Of Nature hit. Dammit, right when things were starting to click.

I headed back to the john, and even though there weren't many people in the bar, there was a line. It took me a good three minutes to get to the urinal so I could piss and get out of there. I made a beeline for the corner booth. There were two empty bottles on the table, but no sign of her. I figured she had to pee as well, so I headed to the bar to get two more beers.

When I got there, the bartender said, "Your ladyfriend there paid off the tab."

"She left?" He nodded. "Shit. Shit, shit shit."

The barkeep smiled. "Relax. She left you a note." He smirked. "Have a good night, buddy."

Asshole. "Thanks." I turned and started walking away. Damned if I was going to let that schmuck see me rip open the envelope like a kid with a birthday card hoping for money inside. I walked to where the light was better and slipped it open. The note read:

I'm feeling adventurous.

And better yet, there was a hotel door-key card included. Room 469. A broad grin creased my face. 469? Oh, yeah -- and I liked the symbolism. I headed to the elevators as quickly as I could.

I stepped off the elevator on the fourth floor and took a right like the sign on the wall said. It looked like room 469 was all the way at the end of the hall. When I got there, I took the card out of the folder and started to slip it into the slot. At that point I paused and rubbed my naked left ring finger. I felt myself shiver with anticipation, and plunged the card in and pulled it out rapidly. The green light went on, and I opened the door and stepped into the hotel room.

She was standing next to the queen-sized bed, with two more buttons open on her blouse showing off even more of those lovely D-cup tits as she slipped off her shoes. She smiled and licked her lips as her face began to flush. "Didn't take you long to get here."

"Let's just say that in sales you have to make your move when the time is right. And the time couldn't be any righter. Strike when the iron is hot, and all that." I closed the door walked toward her.

"Iron, hunh? We'll see." As I reached her, I placed my hand on her lower back and pulled her to me as I leaned down to kiss her. Our lips met for a moment, then her lips parted and the kiss progressed rapidly. My hand slipped down to her ass and I pulled her closer. She responded by pressing even closer and then suddenly stopped and chuckled.

"Iron is a VERY good word," she said as her right hand slid down to touch the tenting crotch of my pants. She rubbed my gently. "I like iron. A lot."

I shivered, then let out an involuntary groan as she slipped out of my arms and took a couple of steps back. She started to unbutton her blouse, and I reached out and grabbed her hands. "That's my job."

"Then get to work while I do my job." As I unbuttoned the next two buttons, she began to return the favor and started working on my shirt. I pulled her shirttail out of her pants, and slid my fingers into the front of her bra and stroked her rock hard right nipple. It was her turn to shiver.

I slipped my hand out of her bra, and slid my shirt off, then slid off her blouse. I rubbed and caressed her back, then bent down to nibble at the nape of her neck. She jumped and let out a squeal. I stopped nuzzling her neck and slid down to kiss between her breasts. The three fasteners on her bra unsnapped easily.

I straightened up and gently grasped the straps to guide it off of her body to reveal those sexy tits. She had the classic redhead complexion, including the dusting of freckles across her chest that only made her hotter. I again pulled her to me and resumed kissing her deeply. Our bare chests met, and the heat came off of both of us in virtual waves.

I slipped off my shoes, then fell to my knees and began to lick and suck her nipples. "Oh, yes," she whispered under her breath as I worked from her right side to her left and back again. The nipples stood out like pebbles from her heavy tits, and I drank in the sight of them each time I changed sides.

I raised my hands and squeezed her tits together and began sucking on both nipples at the same time. This time when she said "Yes" it wasn't under her breath. She put her hands behind my head to pull me closer as I continued to give her beautiful nipples the attention they deserved.

When I pulled back, I unsnapped her pants, and slid the zipper down. The aroma of her arousal was unmistakable, and it only inflamed me further. She pulled at my arms, asking me wordlessly to stand up.

I complied and she reached down and worked on undoing my belt. She bit her lower lip in concentration, and her tits swayed gently as she completed the task. Unsnap went my pants, zzzzip went the zipper, and slid her right hand into my underwear to grab my now rock-hard dick.

"Oh, I knew it would be nice and big," she said, looking me in the eye. "Just what I need." She began sliding my pants and underwear down as she fell to her knees. I'm no fool. I stepped back and out of my pants, and as I did, my dick almost slapped her in the face. She grasped it and smiled. "You could put an eye out with that big thing. I have a better idea."

She leaned forward and slid my dick into her mouth. She bobbed her head once or twice, then pulled it out and gave it a lick, swirling her tongue around the tip and the glans. The feeling was indescribable. "Mmmm, nice," she said sotto voce and again began sliding it in and out of her warm, moist mouth.

I wanted to throw my head back and close my eyes to concentrate on the sensations, but I couldn't tear my gaze away from this sexy woman attacking my dick oh so firmly and oh so gently at the same time. She knew the right rhythm, the right pace, the right method, to put me on the edge almost immediately. It was clear she knew what she was doing, and that she enjoyed doing it.

"You like watching me suck your dick, don't you," she said saucily as she tilted her head back to look me in the eye. "You like having me on my knees in front of you, don't you? You like the thought of standing over me while I do this don't you?"

All I could do was nod. "I like doing it. Your dick is perfect for sucking. Do you want me to put it back in my mouth?"

"God, yes," I gasped.

"I will when I'm good and ready." She stuck her tongue out. "I have something else in mind. Oh, my. These are nice balls." She began licking my ball sac, gently sucking on one then the other before raising back up and running her tongue along the underside of my shaft all the way to the head. My knees began trembling. It was almost more than I could handle.

It was then that she stood up. "I've been doing all the work so far. Now it's time for you to do something." She reached out and took my hand and slid it into her panties. They were absolutely soaked with her juices. I took my index finger and slid it up and down along her pussy, grazing the clit one, two, three times. She gasped when I pulled my hand away. That's when I slid her pants and panties down in one motion, exposing her slickness. When they were past her thighs, I dropped down to my knees to make it easier for her to step out of her clothes. She disentangled and stepped forward, giving me a good look at her snatch.

It was a beauty, no other way to describe it. She'd trimmed her pubic hair to a minimum -- not a landing strip or anything like that, just trimmed the hair back to give easier access to what really mattered. The lips were obviously swollen with desire and gave off a clean, musky scent that ratcheted up my desire another notch. This was a pussy I not only wanted, but that I HAD to have. And I knew was going to get my wish.

It doesn't get any better than that, right? Guess again. I looked at her. "You're right. You have done all the work so far. It's time for me to take care of you." I grasped her by the waist and gently pushed down, forcing her to flex her knees. That opened up her thighs and I leaned forward with my tongue extended and began to work on her box.

I licked up and down along her pussy lips, briefly making contact with her clit at the top of the stroke before moving back down. After doing this three or four times, her pussy really began to flow. I tasted the juices of her desire. Tart, musky, sexy. Just right. Yeah, just right.

When I tilted my head back further, I put myself at the proper angle to slide my tongue into her tunnel. That's when she let out a long, drawn out "Ohhhhh...." and grabbed the back of my head, pushing me deeper into the Y formed by her legs. I grabbed her ass, and tried to slide my tongue even deeper. About three thrusts like this was about all she could handle. She stepped back, breathing heavily. I like what that did for her tits as she tried to get her wits back.

She took another step back, and bumped into the queen sized bed. "It's time to find out how much this mattress squeaks." She licked her lips slowly. "This is a pretty nice hotel. I'd bet you'd have to be fucking me pretty hard to make the bed squeak."

If possible, my dick got even stiffer as she spoke. She walked to the far side of the bed and peeled back the covers, and then lay down on the mattress. I walked over to the side of the bed, and she grasped my rock-hard prick and slid it into her mouth and began sucking on it again. That stopped me in my tracks as I felt myself begin to approach a climax. "Oh no you don't," she said. "My pussy needs to be filled."

"And I'm going to fill it, don't you worry." I crawled onto the bed. "Slide up a little bit and open those beautiful thighs for me." I rose to my knees and placed myself into position to enter her. Her pussy was sopping wet, the lips pink and engorged with blood. I reached out with my right hand and slid my fingers along her labia, teasing the swollen lips then caressing her clit. "Are you ready for me? I want you to tell me what you want."

She let out a small moan. "I want your dick inside me. My pussy needs it. I need it. Fuck me with that big dick now."

I had to fight myself, but I managed to maintain control. Placing the head of my cock at her opening, I began to slide myself inside ever so slowly. The feeling was indescribable. Her cunt was tight and warm, and wrapped itself around my shaft like velvet. Wet velvet, of course, but this was the sensation that has caused men to do desperate things to experience the ecstacy of taking a beautiful woman. Wars had been fought over less. And this was certainly not less by any stretch of the imagination. This was more, almost more than I could handle.

The first thrust was slow and measured. She gave out a little gasp and hitched her hips forward in an effort to drive me deeper into her tunnel. "You like my dick, don't you? You like being fucked by it, don't you?"

"Oh yessss," she hissed. "Dammit, fuck me deep!"

Ah, to hell with self control, I thought. I sank my cock in all the way to the hilt, and she let out another gasp, then began to push back with her hips. I tried to keep a measured pace as I kept driving it in, feeling it strike bottom again and again. But this bottom was a soft, welcoming place, one that kept drawing me in like a magnet. We bucked and thrashed on the bed like a man and woman possessed, driving and searching for the destination.

I kept lifting her up as I sought to go as deep as I possibly could, looking for the exact right spot in her pussy to drive her over the edge. Then I found that magic place. She began to moan, giving a little cry, then her body began to shake as her tunnel began to clench and spasm, squeezing my dick like it had never been squeezed before. Suddenly, another cry from her, and I felt a flood of moistness surround me. It was at that point that I gave out a cry of my own and began to fill her with my own juices.

12