Road Stories: Bueller

Road Stories is set in the same neighborhood as "The Consultant" and "Neighbors", but the stories will be standalone so don't feel like you can't jump right in!

All sex-having people in the story are over 18 years old.

Sales is a tough business. You pour so much energy into every deal, and sometimes they just don't happen for reasons outside your control.

I'd been working this one new customer in Chicago for months, and we were finally about to wrap up negotiations for a three-year deal plus a lucrative implementation contract. What could go wrong?

The final meetings went well and everything was on schedule, until around 3:30pm when the CIO's executive assistant came into the meeting room to let us know that he had left after hearing that his daughter had been in an accident. He expected to be gone the rest of the week.

Of course I felt bad for the guy and conveyed my best wishes for his daughter's speedy recovery. But our fiscal quarter ended that Thursday and not being able to sign this deal was going to blow my bonus. I was not a happy camper.

I took an Uber from their offices in The Loop back up to the hotel on Michigan Avenue where I was staying. My flight out of O'Hare was not until 2pm the next afternoon, since I had planned on keeping the customer out late for dinner and drinks. I tried to get an earlier flight out, but the 6am flight they offered me sounded horrible and I was going to have to pay for the hotel anyway.

So I canceled the dinner reservations, took a nap, and then headed down to the lobby bar. It appeared to be one of the few weeks of the year when nothing much was going on at McCormick Place or any of the other convention centers in Chicago. The bar was pretty dead, which I decided was probably fine as I was in a lousy mood.

I had a pretty good burger at the bar, talking with the bored bartender enough to hopefully keep him from watering down my drinks. He was a nice enough guy but seemed to recognize that I wasn't interested in much small talk -- the sign of a great bartender.

When he looked past me and his jaw dropped, I couldn't help but turn around. She swept into the bar like she owned the joint, despite only being about five feet tall. Short leather skirt, leather bustier, topped with a floor length semi-sheer cardigan that would have dragged the ground if not for her four-inch heels.

I nodded to the bartender that her drinks were on me. She sat down a few stools away, but when he delivered her martini and nodded my way, she moved to the stool next to me.

"Thanks, cowboy!"

We chatted over our drinks for a few minutes, flirting but not too outrageously. She noticed me noticing her large wedding ring and put her hand on top of mine on the bar. "Don't worry, hubby is tied up this evening."

"So what's your name, cowboy?" she finally asked as we finished our drinks.

Being in Chicago and only a few blocks from the Art Institute of Chicago, I couldn't help myself. "Abe. Abe Froman."

She looked confused for a moment before it dawned on her. "So you're the Sausage King of Chicago! That's a tough title to live up to. My friends call me 'Shauna'. So, Abe, I've got a bottle of Scotch in my room that is almost old enough to legally drink itself. Would you like a little taste?"

"Okay, Jean, lead the way," I replied, getting a laugh and an elbow in my side.

She swiped her key, and I held the door open for her. When I turned around, she pulled my head down for a deep kiss. Then I looked past her and saw the naked guy tied up in a chair in the corner, ball gag firmly in place.

"Nope." I spun on my heel and headed for the door.

"C'mon, Abe! I told you he was tied up for the evening. He likes to watch, and he doesn't get untied until you leave." She shrugged her cardigan off and unzipped her skirt, letting it fall to the floor. It was obvious even in the dim light that she was freshly waxed. "You're not going to leave me hanging, are you?"

It wasn't that I had never had sex with an audience. Alli and I had gone to some pretty crazy parties with some of the other grad students in our day, and we had no compunctions about getting busy with other people in the room. But this was clearly different.

Then my new friend reached behind her back and undid the clasps of her bustier and suddenly she was naked except for her heels, her perky little tits begging for action. "C'mon, cowboy. Don't you want to see if you can break me?"

Fuck it. I took a step towards her and picked her up. She got the hint and wrapped her legs around my waist, my erection rubbing against her most private place through my jeans while we kissed. She tasted like vodka and fire.

"Let me taste you, lover!"

I lowered her, and she made short work of my pants while I unbuttoned my shirt. She looked back at her husband and then turned me a little before she bent over and took my cock in her mouth. Giving him the best possible view, I guess.

Her mouth and her tongue were quite enough to make me forget that her cuck of a husband was tied up in the corner. I didn't understand the game they were playing, but I didn't mind being used, as long as it was by her, and her alone.

And she was good. This clearly wasn't her first rodeo. She bobbed her head up and down for a bit, then stopped to slowly lick me from balls to tip -- all designed to keep me on edge but not push me over.

I made the mistake of glancing over at her hubby a couple of times, and the hungry look on his face was obvious despite his gag. And to be honest, it was a little unnerving. Enough so that I started losing my interest in an otherwise damn fine blowjob.

It must have been obvious that my attention was flagging, as Shauna gave me one last lick and rose to lie back on the bed. "Come on, Abe! Let's see how you got the title of Sausage King!"

I mounted her, my back mercifully to the man in the corner. I sank my length into her and felt her pussy squeezing around me. "That's it, baby! Fuck your little slut!"

She didn't have to tell me twice. I pulled back and slammed down into her, her husband forgotten. A couple more hard thrusts and then I started sawing in and out of her, shoving my cock into her so hard I was sure we would both have bruises the next day.

"Fuck, cowboy! unh I'm so close! unh Keep pounding me! unh Oh fuck! unh I'm cumming!"

She felt fantastic but with the weirdness (and the drinks I'd had) I wasn't close to my own climax yet. After her breathing slowed a little, I flipped her over (she was tiny!) and turned her around to face her man.

"No, baby, he likes to see my pussy getting ravaged!"

"Well tonight he's going to watch your face as I make you cum a few more times."

She tried to shift around, but I held her hips and speared her deep and she shuddered and lowered her face to the bed. I went slow and steady and HARD, like one of those crazy fucking machines in the videos. Relentless.

I also stopped ignoring her lesser half and looked his way while I systematically destroyed his wife's cunt. Look, it's not like I didn't know my Alli was probably with someone else at that moment -- this was different. Wasn't it? He ignored me and focused all his attention on her.

I could feel Shauna tightening up again, so I reached down and grabbed a handful of her hair and pulled back, raising her head so that she was staring into her husband's eyes.

"You love this dick, don't you, slut?"

"Unh unh yes! God yes! Keep fucking me, stud!"

"You like this cock fucking you so deep? Hitting all those places no one else can?"

"Fuck yes! Keep smashing me, cowboy!"

I was finally getting close. I let her head drop back down to the bed and gave her butt a couple of hard slaps before grabbing her hips again and railing her even harder. I was ignoring her husband now, paying more attention to her tight little ass jiggling every time I pounded my cock into her.

"I'm getting close, baby!"

"Cum inside me, Abe! Gimme that cum!"

I didn't want to disappoint her, so I did just that, finally letting go and filling her with all the jizz I'd been building up all night. It felt like every bit of liquid in my body was flowing through me and into her. It felt fucking amazing.

I pulled out and collapsed on the bed, her husband forgotten. She turned and laid down next to me, kissing me in an act of intimacy that maybe felt a little out of place, but it was really, really nice.

"God, baby, that was so good. Think you're going to be able to go another round in a few minutes?"

I was thinking that with a little help, it would be less than a few. Then I spotted the purple bottle of lube on the end table.

"Shauna, honey, what about...?"

She saw what I was looking at and took a deep breath. "No, baby, my husband wants me to save that for him."

I gave a little disgusted snort. "Is this all for him? Did he put you up to this?" Her silence and her inability to look me in the eyes gave me my answer. "What do YOU want, sweetheart?"

She sighed and we both seemed to forget that he was five feet away. "He thought it would spice thing up in the bedroom. I guess I thought things were spicy enough. But I'm happy fucking other guys if they're as nice as you."

"And when they're not?"

"Some of them have been... rough. Not in a good way." My opinion of her husband dropped even further.

"Sweetie, what would you like to do? It's just me and you here. I can leave -- "

"No!"

"... or we can fuck some more."

She looked past me at her husband and then back at the bottle of lube and then at me. "Abe Froman, Sausage King of Chicago, would you fuck my tiny tight little asshole? Please? I spent an hour cleaning myself out -- for him -- before I ran into you. I'm all yours."

I heard shifting and groaning from the man in the corner, but I didn't give a single fuck. "Shauna, there is nothing in this world that I would rather do."

I flipped over her to grab the bottle and she rolled over on her side to face her red-faced husband. I tried to warm the lube up a little, but she still jumped when I ran a well-lubed middle finger around her pucker.

"Slow. Please." Well of course. I ran my finger into her, slowly but firmly. She was clearly a veteran of anal sex and knew exactly how to relax and how to push and that one finger quickly became two.

"I'm ready, cowboy. Let's ride!" I lubed myself up good and my cock replaced my fingers, meeting no more resistance than my digits had. She felt so good and so tight and so right. I took it slow, savoring every inch of her, as she seemed to do with me.

She twisted her head around so that we could kiss, and her fingers flew across her sex. I wasn't going to last as long this time, but it was okay. I could feel it as she crammed three fingers into her pussy and tightened around me as she came again. I was not far behind her, pumping into her while she was still shaking. Fuck, she felt good!

After we both stilled, she gave me one final kiss then turned her back to her husband, running her finger through my spend that was leaking out of both her ass and her pussy. She looked over her shoulder and I could see in the mirror that she stared at her husband as she licked her fingers cleaned.

It was clear that we were done. I quickly got dressed and she walked me to the door, pulling me down for a final kiss and a whisper in my ear. "Thanks, cowboy. Hubby and I have got some things to talk about. Thanks for being a nice man. And a great fuck."

I headed back to my room, tired and looking forward to my flight home and another story to tell Alli. She was going to love this one!