Road Stories: The Customer

Road Stories is set in the same world 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.

After months spent away from home working with my biggest Chicago customer, we finally signed the contracts -- and I made a ton on commissions. But that was really just phase one. Phase two was planning and implementation, and that was going to take a couple of months at least.

You'd think that the sales guy would be done after getting the contract signed, but you'd think wrong. If anything didn't go well, it was my ass on the line (and my bucks). So I was with the project manager and the implementation lead every step of the way.

Our customer face-off was the AVP of Application Support, Amanda Harper. She was fucking brilliant. She was also hot, and no older than her mid-30s, which of course gave rise to rumors that she slept her way into her position. If a 35-year-old guy was in that position, they would just assume he was, well, brilliant. People suck.

She dressed in severe suits with her light brown hair pulled back, usually wearing glasses that I'm pretty sure she didn't need. I tried to make it clear that I respected her for her, and that may have gone a long way to getting the deal.

We were finally ready to go live on a Saturday night in November. It was starting to get cold (Chicago, right?) and I was ready to do this and get home to Alli and Zoey for Thanksgiving before I froze to death.

The data center was out in Schaumburg, and the PM and Amanda decided that we should all stay out at the Marriott nearby "in case anything went wrong". It's software, people! Being onsite was not going to be necessary! But their nervousness ruled the day.

Thankfully, we absolutely kicked ass on the cut-over. Of course there were a couple of minor hiccups, but they were quickly resolved. The support team planned to hang out in the hotel conference room that we had rented for a couple more hours just in case, the table a mass of laptops, monitors, power bricks, and empty Funyuns bags and coffee cups.

I offered to buy drinks at the bar for anyone that wasn't sticking around (and I sent one of the guys out to the store to pick up a couple of six packs for the team in the conference room to enjoy later). The PM, Brad, took me up on the offer, along with Terry, who was the solution architect for the whole deal.

We tried to talk Amanda into joining us and we thought we had her. Then she looked at the three of us and gave us a little smile. "I'll tell you what, fellas. I'm going to go back to my room and get out of this suit and call my husband. If you're still here when I come back down, I'll take that drink."

I was finishing my second Goose Island IPA when Terry nudged me. Amanda had walked into the lobby bar and spotted us. I was a little disappointed to see that she was wearing a tan trench coat, figuring she'd decided to drive home.

It was the first time I'd seen her with her hair down, and she'd reapplied her makeup. She looked even hotter than usual. Her high heels clacked on the tile floor as she walked over to join us, motioning us to gather around her.

"Gentlemen, I have a proposition for you. Had this gone south, I would likely be out of a job. As it is, I'm likely in line to be the next CIO. So my husband had a suggestion for a suitable bonus for you."

She looked around to see that no one was watching and then flipped open her coat, closing it again just a quickly. But not before we caught a glimpse of an emerald green lace teddy and lots (and I mean LOTS) of bare skin.

"If you're interested, and if you can be discreet, I've got a fifth of Four Roses Small Batch in my room. And I'll be there. And I won't be wearing this coat. What do you think?"

I'm sure my tongue rolled out of my mouth and onto the floor like a cartoon Big Bad Wolf. All I could really do was nod. A lot. Brad was recently divorced and looked like he had just seen heaven. Terry looked to be the hold out.

"Amanda, you are incredible, but my wife and I are celebrating our 25th anniversary in a couple of weeks and I don't fool around on her. Sadly, I'll have to decline your most delicious offer."

"Tell you what, Terry. Do you think your wife would mind if you drank my whisky and filmed the shenanigans I'm about to get into with these two? My husband's going to want to see it anyway."

He must have decided that his better half was going to be okay with it, because he drained his glass of wine and grinned at Amanda. "Let's go!"

The four of us were alone in the elevator, so I didn't waste any time. I pulled her to me by her lapels and kissed her hard. Brad put his arms around her from behind, kissing her neck while cupping her breasts under her coat. Terry's nerves got to him, and he dropped his phone.

At the elevator ding, we off-boarded and walked down the hall, Amanda in the lead with her coat open, bold as brass. She opened the door to the executive suite and her coat hit the floor before the door closed behind us.

"Boys, if you really want a drink, the bottle is next to the TV. But I'm going to be in the bedroom wearing nothing but these heels in about 10 seconds. Choose wisely."

Brad did look at the bottle for a split second, which meant I made it into the bedroom before he did. But only barely. Amanda was lying back on the bed, her hair spread out on the pillow and her bare legs spread out on the bed. True to her word, her black Louboutins were the only thing she was wearing except for a huge rock of a wedding ring.

"I'm your cum-dumpster tonight, gentlemen. Terry, I want you to record everything. My husband will want to see every debauched thing these guys do to me. Now get your damn clothes off!"

I was already mostly there, but Brad was speed-stripping as well. I kneed my way up the bed and gave Amanda another kiss before presenting my hard cock to her, making sure I didn't kneel on her hair. She kissed the tip and then gasped as Brad knelt between her legs and drove his tongue inside her.

I pushed forward and she took half of me into her mouth. I held her head up, as her hands were busy trying to pull Brad's head into her pussy. I held her steady and sawed in and out of her as her tongue did wonderful things to my cock. She was always beautiful, but with her hair wild and her moaning around my cock as Brad got her close, she was stunning. A fucking goddess.

I could tell by her eyes that she was about to cum, so I pulled out, letting her concentrate on Brad's fingers and mouth. I got a grateful smile before she tensed and shook and groaned through an intense orgasm. I kissed her through it, her arm wrapped around my neck.

"Jeezus, guys! I thought I was offering myself to you, not the other way around!" She rolled over onto her hands and knees. "Come and get me, boys. I want you both to cum inside me."

Brad moved in front of her, his long but thin dick waving in front of her face. "Ooh, I'll bet I can swallow this whole thing, Brad!" She took him in until she gagged a little, then I saw the concentration on her face as she tried to swallow. I don't know if I helped or harmed that effort by suddenly jamming my cock inside her until my balls slapped her clit.

She bucked forward and Brad's cock disappeared. Mine did too, deep inside one of the tightest pussies I'd ever felt. Damn, she was perfect. And her husband was a lucky sumbitch.

Brad and I found an alternating rhythm that got Amanda sawing back and forth between us, taking a dick down her throat and then one deep into her cunt. Sweat glistened on her back as we worked her over, streamers of saliva stretching from her chin to the bed below.

I saw the look on Brad's face and motioned Terry over with his phone in time to catch him pull back and cover Amanda's face with jizz. She took a couple of shots before capturing his cock again with her mouth, sucking the rest out of him until he collapsed onto the bed.

I reached down and grabbed a handful of her hair, damp with sweat, and pulled her head back, forcing her back into an arch as I pounded into her. Terry got directly in front of her, capturing her beautiful, ravaged face on video as she came. She collapsed onto the bed and my cock popped out mid-spurt, but I didn't mind stroking myself through the rest of my orgasm, covering her upturned ass with cum.

She looked back at me, a wild grin on her face. "Fuck yeah! More!" I was happy to oblige, and I hoped Brad could keep up.

I motioned him to lie down on the bed. Amanda pounced on him, sliding her pussy over his recovering cock. She looked up at Terry, who was still valiantly trying to capture everything on video, despite his obvious erection. "Purse. Bathroom counter. Lube." Then she leaned down to kiss Brad.

Terry handed me the phone and disappeared, coming back a couple of minutes later sans pants, and with a plastic bottle of clear magic. I traded him for the phone. I poured a goodly amount of lube onto a couple of fingers as Amanda raised up and then impaled herself onto Brad's mostly recovered member.

Her asshole was tight was fuck as I slid my well-lubed middle finger inside her. She clearly had experience as there was little hesitation before I had my hand pressed firmly against her butt.

I pulled out and added a second finger as she rode Brad, meeting a little more resistance, but she pushed back a little and I buried both fingers inside of her, stroking in and out in opposition to Brad.

"God! Shit! Fuck me, Scott! Give me your dick!"

She might have been a little incoherent, but I had no question about what she wanted. I arranged myself behind her between Brad's legs and lubed up my raging erection. She stopped her bucking when she felt my cock sliding down her crack.

I wrapped an arm around her and she reached a hand back to guide me into her. "Easy, baby. That's it. Fuck! Goddamn shit!" It was an effort not to laugh at the stream of profanities and inanities that escaped her as I started pumping into her ass.

Terry moved around so that he could catch the double-pumping action on camera as Brad found an opposing rhythm and we ensured that our customer was never empty. He reached up and twisted her nipples and she shrieked and tightened up around me so hard that I thought she would break my dick off.

I lost track of how many times she came, and I could tell by the strain on Brad's face that he was close. I knew I sure was. So, I hesitated on my stroke a half beat so that we were both slamming into her at the same time, filling her completely with dick. I gripped her ass, slick with sweat, and fucked her as hard as I could manage.

"Shiiiiiitt! Fuck me goddamn it I'm cumming!!" She was the most vocal woman I'd ever met and I hoped that the hotel management would wait until we were done before they banged on the door to complain. I could feel Brad start to fill her pussy and I backed off a little until he finished. He wilted pretty quickly after that and I slammed back into Amanda to fill the void.

Brad was stuck under us but I wasn't going to stop. I slam-fucked her ass over and over while Brad mauled her breasts and Terry caught every bit of action with one hand while he slowly jerked himself off with the other.

I was getting close and after Amanda rolled through another climax of her own, she started begging me for cum. "Come on, baby! Fill up my butt! Give me that jizz! I want to watch it dripping out of my little asshole!"

That did it. I exploded into her backside, making sure to deposit every drop inside her. Terry caught every twitch in 4K. That was a good thing because I came so hard I almost blacked out.

I pulled out and collapsed onto the bed and Amanda rolled over between me and Brad onto her back. Terry started to put her phone down but she stopped him.

"Wait! You've got to get this!" She spread her legs into a lotus position between us, the soles of her feet together. Jizz was slowly oozing out of her pussy, mixing with the same dribbling out of her asshole.

She squeezed a couple of times, both her pussy and her brownie winking at Terry. Then she reached down and scooped up a fingerful of cream and held it over her mouth until it dripped onto her tongue, before sucking her finger clean.

Terry dropped the phone and ran for the bathroom, too embarrassed to cum in front of us from just watching. I didn't even give him a hard time about it later.

Amanda relaxed back on the bed, turning to kiss Brad and then me. I'm pretty sure she was up for more, but Brad was clearly spent and I didn't want to embarrass him. Okay, I was pretty tapped out too, to be honest. But she didn't look too disappointed.

"Thank you, gentlemen. I'm not exaggerating when I tell you what a career boost this is for me. I won't forget what a great job you did for us. And I hope you won't forget tonight." The last was said with a big grin.

Terry came back in, dressed again, looking dazed. He handed Amanda her phone and she pulled him down to kiss his cheek, rubbing her lipstick off with her thumb. "Are you going to tell your wife about this?"

"Oh, yeah. But not until we're in bed together. 'Night!"

He slipped out into the hall while Brad got dressed. He looked just as dazed as Terry. Amanda got up and gave him a naked hug before he following Terry towards the elevator, leaving me alone with her.

I poured us each a drink. "So you're going to send me a copy of the video, right?"

She looked at me, serious again. "Scott, you know that's a complete career ender for me if anyone was to see it. That's why I used my phone and disabled cloud storage. I'm afraid this is just for me and James."

She took a sip of bourbon, clearly thinking. "But you know, you could bring your wife up next time. Maybe stay the weekend. James and I would love to meet her. And maybe we could all watch the video together."

I touched my glass to hers. "That sounds like a capital idea, Manda!"

I called Alli when I got back to my room. "Hey, babe! How would you like to come up with me after Thanksgiving and do some Christmas shopping on Michigan Avenue? And fuck my customer?" The squeal of delight nearly deafened me.

"I take it that's a 'yes', sweetheart?"