Escorting on Accident

It was just past 11, and most of the other patrons had already filed out of the restaurant. Shane motioned to the waiter for the check.

"You good to get out of here?" he asked me. "Maybe go somewhere a little more active?"

"Um, yeah, of course!" I blushed, trying to hide my excitement a little. I knew it was terrible, but this had been the exact type of night I had wanted from Brett. Why should I feel bad that someone else wanted to pamper me a little?

Besides, I hadn't actually done anything with him....

Yet.

The waiter returned our check. I read the bill upside-down, and boy was I glad that I didn't have to pay.

"You ready?" Shane asked. "Did you have a coat?"

"No, I'm all set, after I use the ladies' room," I said, needing an excuse to make sure I looked good enough to go out.

"Sounds perfect. I'll bring the car around front."

Shane left to go get his car, and I made my way to the bathroom. I realized that the burning in my crotch wasn't just excitement, I did actually have to relieve the three drinks I had. I checked myself out in the mirror after, fixing my long brown hair and making sure the subtle waves my curling iron had created were staying in place.

My makeup and lipstick were touched up briefly and I was ready to roll. A small buzz in my purse reminded me that I hadn't checked my phone since Shane had arrived.

The notification itself was a stupid Apple News Spotlight, but I had a couple missed calls and texts from Brett. I paused momentarily, before turning my phone off and putting it back in my purse. Fuck him. Tonight was about me.

My best friend Jocelyn (Jo) had texted too, asking how our date night was going. Ugh. I'd text her back later.

I made my way back out front of the restaurant, and my jaw almost dropped when I looked at the car idling in a parking space on the curb. Shane rolled down the passenger window and looked over at me.

"She's a beauty, isn't she?l

Sitting in front of me was a bright orange and black McLaren P1. Now I'm not a big car person, but Brett liked the original British Top Gear, so I had seen this before a decent amount. And Christ if it wasn't the sexiest car I had ever seen in my life.

"Oh my god!" I exclaimed. "What the fuck?"

"My dad bought me this a few years back as a grad present," he nonchalantly said.

"That is another level of fuck-you money," I joked as I very carefully got into the passenger seat. If I put so much as a scratch in the leather on this, I might have committed seppuku. "I feel like I've stepped into a different wold right now."

"Well hopefully I can guide you through it," Shane laughed. "Seat belt."

He pulled out into traffic and we started heading further downtown towards Broadway. I had no idea how he could drive anywhere faster than 5 mph without freaking out.

"So where are we going?" I asked.

"I know a guy who owns one of the popular places downtown, if that's cool with you."

"Yeah that sounds great," I responded. "There's going to be a massive wait at this time of night though."

"Did you miss the part where I know the owner?" he joked.

"Right, perks of being filthy rich."

"Exactly. And for you, perks of being with someone who's filthy rich."

"Hmm, I do like the sound of that," I quipped.

The drive wasn't long but the traffic was insane (as to be expected downtown on a Friday night) so it took a while. We made our way down to Broadway, and Shane pulled into the parking garage for a hotel a little bit off the main strip.

"Hey man, same place as normal," Shane said to the valet attendant who came up to him. Shane went to shake the valet's hand, and I noticed him slip the young kid a $20.

"Of course, sir."

"Thanks man," he said and turned back to me. "We good?"

"Yeah," I answered as he both turned to walk towards Broadway. "Do you have a routine for this?" I inquired.

"Well, no way I'm leaving my baby out for street parking. It pays to have connections."

"Can you even park in the lot without staying at the hotel?"

Shane looked at me with a smirk on his face as we kept walking.

"Like I said, pays to have connections."

"Fuck I want your life," I laughed.

"Well you have it for tonight!" he responded. "Hey maybe if it goes really well I'll marry you."

"I mean hey, I wouldn't complain! You could be my sugardaddy."

"God am I really old enough to be a sugardaddy?" he joked. "I did mean to ask you about that though," he continued, nodding his head towards me.

"About what?"

"That," he repeated, nodding his head down again. "Your ring."

I froze. My engagement ring. I hadn't ever taken it off.

Quick! I needed an excuse. Think, Aria, think!

"Oh yeah, uhh, that's from my fiancee," I stammered, which was true. And in Shane's mind, I had been engaged once. "When I'm out on my own it helps to still wear it, just to discourage any unwanted approaches."

"Ahh, I see," Shane answered, I think seeming to buy my story. "You don't think I could do a good enough job beating away anyone else?"

"No no!" I quickly denied. "I'm sure you could. You're right, I don't need it anymore."

I reached down and pulled my ring off my finger, slipping it into my purse. God, what was I doing? And how had I let the night come to this? I should've stopped the charade long ago, or never started it at all.

But I had. I knew I could stop it at any point if I really wanted to. A part of me still felt like I was okay, since technically I hadn't done anything wrong. But I also knew that I 100% would not be so innocent at the end of the night. The alcohol was already working in my system, and I had been in both an adventurous and pissed-off mood. This was a dangerous combination. Try as I might (admittedly not that hard), I couldn't stop my feet from carrying me forward.

We reached the three-block strip of bars that made Nashville's downtown famous. The streets and sidewalks were absolutely packed shoulder-to-shoulder with people, tons of college-aged girls in barely-there dresses, young frat guys trying to pick them up, and a host of middle-aged trashy-looking white people in cowboy hats. The real lifeblood of the city.

I stood right next to Shane, following him as we made our way through the throng to whichever place he was going. I almost thought I was going to lose him, but as we pushed through a particularly dense patch, he wrapped his arm around my waist and pulled me tightly to his side.

I was slightly taken-aback, but felt a burning in my crotch. The fact that he was taking charge turned me on. He was protecting me, and almost establishing dominance.

We made our way to the place Shane knew. He walked straight past the block-long line up to the bouncer, gave him a big hug, and walked straight in, motioning for me to follow him. The feeling of being a VIP was getting to my head a little bit. I felt a hundred feet tall. Or maybe that was the three drinks with dinner.

Shane grabbed my hand and lead me up through the multi-leveled establishment to the rooftop. It was less of a honkytonk and more of a country-themed club, but those were just as fun. We made our way to a couch in the corner of the open rooftop area and sat down.

"Good to be alone," I said, or more accurately shouted over the deafening buzz of hundreds of people jam-packed in a small area, plus the live band blaring out some Toby Keith.

"Yeah I know! It's part of what makes it fun, but at the same time, I do wish there weren't always quite as many people though!" Shane yelled back.

"Agreed! Although I'd assume all the bars near campus in Michigan would be like this too, the school's fucking huge!"

"Yeah, they really were! I kinda miss those days!"

We were interrupted as a tall, round, Hispanic man with a shaved head and a goatee came up to Shane.

"Yo bitch, what's fucking up?" he boomed out, and he and Shane hugged. They started talking but I couldn't hear and had no idea what they were saying. I sat, smiling and looking pretty, until the man motioned to me.

"Yeah, this is Aria!" I could make out Shane saying. Taking my cue, I stood up and reached my hand out to the large man.

"It's a pleasure to meet you!" I said, trying to yell while also sounding as minimally aggressive and dominating as I could.

"Pleasure's all mine baby!" the man shot back. "How do you find ones this hot, man?" he said to Shane.

"Luck!" he joked.

"And the car!" I chimed in. "That's how he got me!" I wasn't sure if Shane cared if people knew I was his escort. No, that I was pretending to be his escort. I had to remind myself that I was only playing a role.

"You're right, that thing's fucking gorgeous!" the guy said. "Listen, I'm gonna have one of the girls bring you guys over some drinks, okay? Drink up, fucking enjoy yourselves, alright?"

"We will man!" Shane replied and they bro-hugged before the bigger man left.

"Friend of yours?" I asked.

"Sort of! He's the fucking man though!"

As the night went on, I would find that Shane had lots of "sort-of" friends.

There was a steady stream of people who approached him, appearing like they came from all walks of life. The pretty bartender who brought us over a platter stocked full with tequila shots and beers gave a wide smile to Shane and chatted with him for a bit like they were old friends. There was a twinkle in her eye that certainly seemed to tell me that they were (or had been) more than just friends too.

But I didn't press Shane. I was an engaged woman out on the town with an incredibly charming, incredibly rich, and incredibly single man who had every pretense of fucking me later. If he had boned the bartender before, who was I to judge?

A fair few people from the crowd came over to Shane too, plus the drummer from the band that was playing. I stopped even questioning how he knew all these people; I'd come to accept that Shane was the real-life Dos Equis man.

The music was loud, I was glued to Shane's hip, and the constant flow of visitors also meant a variety of drinking partners. My first drinks from earlier in the night had at least partially warn off, but I still had a buzz on, and after doing a shot and ordering a Whiteclaw (not a beer gal), I was feeling very activated.

"Come on, let's dance!" I yelled out to Shane as I slammed down my empty claw clan on the table.

Before waiting for his response, I grabbed his wrist and pulled him up with me. We pushed forward a little into the massive congregation of drunk college students jumping and dancing erratically. The band was playing "All Summer Long" now, a little better of a dancing song.

I generally got very wild and bubbly when alcohol was in my system, so I had no inhibitions about shaking my ass off to Kid Rock. I could feel Shane right behind me, one hand planted on my hip.

As some other drunk college girls dressed in basically bikini tops and short shorts (who looked not a day over 18) bumped into me, I was pushed further back into Shane, who had nowhere to go with people behind him. My butt pressed right up against his crotch, and I could feel a semi hard-on straining through his pants against me.

He couldn't see it but a wide smile was adorning my face. He was hard for me. He wanted to fuck me. I had him in my control. This entire night was in my hands, and I had taken us exactly where I wanted to go. Whether or not I'd regret that in the morning was another matter.

I wasn't about to stop now. I started shifting my hips, slowly rocking back against Shane in rhythm with the music. I leaned back, resting my upper body against his broad, strong chest, snaking one arm behind his neck. Both of his hands had shifted to my hips, steadying me as I continued to grind on him.

This night was almost perfect, just what I had pictured with Brett. And if he wanted to be missing out, then fuck him. Because somebody else would be fucking me.

Shane's hands were wandering; his right hand had worked its way up my bare side. His fingers brushed over the doves just above my ribcage that swung down to my underboob. His hand started inching forward, his fingers slithering their way beneath the narrow side of my dress and just reaching my breast.

Before he fully could grope me, I quickly swung around and brought my other arm around his neck too. I pulled Shane in tighter and craned my neck up just as his lips came to reach mine in a beautiful kiss.

The kiss was not measured or sensual. It was pure, raw lust. Shane groaned as my full lips pressed hard against his, and my pussy was on fire. My leg was between his, and his cock throbbed against my thigh.

We held the kiss for a few seconds before I pulled away and caught my breath.

"Wanna head back to my place?" Shane bent down and whispered in my ear.

"Yes!" I yelled back, trying not to beam too much.

"Sweet. Let's get out of here."

He started pushing his way back through the crowd out the way we came.

"Wait!" I called out to him, running back to the booth where we'd been to collect my purse. The tray of drinks was still nowhere near empty. I was very horny and ready for whatever the rest of the night was about to bring me, but I knew the more alcohol, the more willing I'd be, for better or worse. Plus I was only really buzzed.

I threw back another shot of tequila. Now I was drunk.

"Okay! We're ready!" I called back to Shane, stumbling in my heels a little as the tequila burned my throat and stomach on its way down.

We made our way out of the bar and back towards Shane's car. I was leaning on him, both for support (you try walking drunk in 4-inch stilettos) and just so I could feel his body. His arm was wrapped around me, his hand having slowly crept down to rest on my far ass cheek.

The valet pulled Shane's car around and opened the doors for us.

"You sure you're good to drive, sir?" the young man inquired. I had had enough to drink on my own without worrying about Shane too, but the kid had a point. The last mistake you'd want to make drunk is crashing your million dollar car.

"Ehh, I'm probably fine," he said, without much of a slur to his words. He admittedly could hold his alcohol pretty well, at least better than me (although I was a girl to be fair; most of my college sorority friends were gone after 3 or 4 so at least I had a bit of a leg up on them). "Tell you what Mark, I'll give you a Benjamin and let you drive the car if you get us back to my place."

"Um of course, sir!" the kid couldn't choke out fast enough. "Hopefully it'll be quick and my boss won't notice."

As the valet (Mark, apparently) and Shane clambered into the car, I was left flashing back to my elementary school days of losing Musical Chairs.

"Where'm I sp's'd to sit?" I stammered. Ah shit, I was slurring my words too much. I needed to sober up.

Shane patted his lap, not needing to elaborate.

"Okay, that works for me," I said, clearly enunciating each phoneme. Fuck, now did I sound like I was trying too hard to sound like I wasn't drunk? God I was getting anxious. This was why I rarely smoked weed.

I tottered up to the passenger side of the car and took a few deep breaths, calming myself down a little. I had no reason to be anxious anyway, I didn't know why I was getting in my own head.

I stooped down, a definite challenge in my heels (drunk or not) and slowly fumbled my way inside the cramped space so I was sitting on top of Shane's lap. It was not the most comfortable position I'd ever been in.

"We ready?" the valet asked, positively beaming that he'd be getting to drive the McLaren beyond just a parking garage.

"Yus sir," Shane answered.

We started moving on the short trip back to Shane's apartment. As gorgeous as the P1 was, a comfy suspension and spacious interior seating weren't its greatest assets. I was feeling every bump in the road, almost bouncing on Shane's lap.

For his part, it certainly seemed like he was enjoying the ride. As I unintentionally bounced up and down over and over on his dick, I could feel the solid rod hardening against my ass to the point that I was basically dry humping him.

His hands, which had started on my hips, had now snaked their way up my dress. Shane's fingers slid underneath the flimsy strips of fabric covering my breasts and came to a rest with my tits in hand.

A small moan emanated from my mouth, almost subconsciously, and my eyes closed in pleasure. Shane lightly squeezed and kneaded the flesh of my small boobs. The were only a B but they were perky enough to still be very fun to play with. At least, I hadn't gotten any complaints.

Shane's fingers ran over my nipples, my small pink nubs hardening against his touch. I could feel his cock surge at that to match. He grasped my nipples between his thumb and index finger in both hands and lightly pinched them, rolling them between his fingers.

I was incredibly turned on, and I loved having my boobies played with too. I hadn't even noticed that I'd started grinding my hips down against Shane's thick rod, exacerbated by the continual bumping from the car.

"Eyes stay on the road man, this car's worth more than your family," I heard Shane say. I looked over just as Mark turned his gaze away from my chest back to the road. We were putting on quite a show.

Shane had every intention of making that show better too. While his left hand kept teasing my boobs, his right hand snaked its way downward over my dress before reaching the bottom hem. He tugged on the fabric a little, helping my dress ride up.

"I'm not wearing any panties," I whispered.

"Good," Shane answered before kissing the back of my neck.

"Fuck you're naughty!" I giggled.

"That's why I pay you, to keep up with me." I had almost completely forgotten I was supposed to be an escort. This all just felt so incredibly natural.

Shane's hand kept venturing up my skirt, moving farther up my inner thigh to my snatch. My breathing was becoming more rapid, the intense burning in my sex feeling like it might just be quelled.

Alas, it was not to be right then.

"Ahem," Mark cleared his throat rather loudly. Only then did I realize the car was no longer moving, and was in fact out front of the gate for an apartment's parking garage. "Sir, I need your keycard scan."

Shane's hands reluctantly removed themselves from my body, and he dug through his pockets to get his wallet. We scanned into the garage, and Mark pulled the car in, parking in the spot that Shane indicated was reserved for him.

"Is that all sir?" Mark asked.

"Yeah man, thanks for the ride," Shane said, slipping him a $100 bill. "Hopefully the Uber back's not too much."

"Don't worry, I'll be fine," Mark said as he exited the McLaren. "Thank you sir!"

I followed the valet's lead and clambered my way out of the car, almost eating shit when I put weight on my heels again.

"Jesus!" I yelled out, but Shane was holding one of my wrists and kept me standing. He slipped out of the car as well, and we worked our way to the elevator.

"What floor do you live on?" I inquired.

"Penthouse obviously," Shane responded. "I'm not a pleb."

"I need your life," I responded.

"Hey I already told you. I'll be your sugardaddy."

"Aren't you not supposed to fall in love with the hooker?" I asked.

"Yeah but when her boobs are that adorable, it's hard not to."

I laughed both at Shane's statement, and the fact that it made me realize I hadn't ever covered my chest up again.

"Is that all I am to you? Just a pair of tits and a pretty face?"

"Nah," Shane answered, a crooked smile turning up the corners of his mouth. "You've also got a fat ass."

"Prick," I played back.

The elevator arrived, and we stepped in. Shane swiped his card again to access the penthouse and the entire contraption began whirring as it carried us up the massive building. I immediately made a move to step to Shane, but he stopped me.