Alex messaged me mentioning he was going to Calgary to visit some family in the next couple weeks. I was contemplating flying out there myself for a conference. I let Alex know and asked if he wanted to meet up at the hotel where the conference was being held.

He agreed but didn't know when he'd be able to get away from the family. I replied that it was fine and I'd leave a key at the front desk for him so he could pop in whenever since I knew I wouldn't have a lot of access to my phone during the conference.

I barely got any work done over the next couple weeks. My days were filled with intrusive thoughts about seeing Alex again. I hadn't seen him since our bathroom encounter and was eager to spend more than a few minutes with him.

I knew he was looking forward to it: he kept writing out his fantasies about me in /erotica. His stories made it clear he thought he was hot shit; he thought he could make me cum in seconds. I challenged him: if you can make me cum within five minutes, you can fuck my tight asshole.

Alex was always eager for anal but his enormous girth made me more than a bit hesitant. I figured the wager was safe bet. So did he.

I flew to Calgary, and spent my first day there in black heels, white blouse, black skirt, and blazer trying to take in the information I ostensibly paid to learn. It was nearly impossible when my pussy was aching for Alex.

When the day was done, I went upstairs to my room but was disappointed to find Alex wasn't there yet. I checked my phone, but no messages from him. I grabbed a shower and got ready to go back down to the bar where some colleagues invited me to join them for drinks.

It was an upscale bar, so I put on a lacy black dress with a cut-out along my lower back. I wore a red bra and thong and tossed my heels back on.

Drinks with the colleagues was fun enough. One of the men in our group kept hinting that I should join him in his room. He was handsome and I was flattered, but knew I had something better coming along.

I arrived at my room tipsy - my pussy pulsing. I was ready to see Master Boss again. I opened the door to find the room still empty.

I was tired after a long day and several overpriced drinks. I grabbed a shower; tossed on some boy shorts and a t shirt and flopped down face-first the king sized bed.

Soon after, I was dreaming about being in an office: someone's corner office. Must be one of the partners at the firm. I'd given him a draft factum for a case we were working on. He wasn't happy with my work. He told me to put my hands on his desk and bend over. He unbuckled his pants, pulled his belt off, and roughly lifted my skirt. I wasn't wearing any panties crack. the belt came down across my bare ass.

I told him I could redraft the factum. "That's not what I want" - Alex's voice.

He sat down in a chair behind me and pulled me down on top of him. I could feel his massive dick was hard. Part of me was outraged at his audacity, but I started grinding my ass against his dick anyway. It felt incredible. I kept grinding and moaning.

In a state between wakefulness and sleep, I kept grinding - vaguely realizing that someone was actually rubbing my pussy over my boy-shorts. I felt the hand retreat. It was quickly replaced by something much bigger. I felt Alex' dick press against my backside. I eagerly raised my hips. He pulled off the boy-shorts and slid his dick along my wet pussy: rubbing my clit with every thrust. I was working my hips to match his thrusts. After a couple minutes, I thought I was going to burst, but Alex changed Rythm and started trying to maneuver his giant dick inside of me. I felt the head of it push against my pussy. I was so horny, but still needed him to go slowly. Thankfully he alternated between easing into my pussy and rubbing his dick along my lips and clit.

Each cycle, he pushed into me a little further until he was finally all the way in. He quickened his pace but within a minute he slowed to a stop. He was trying to keep from blowing his load so quickly. I looked back mischievously and pushed back into him. Taking in every inch, and increasing the speed as I went until he came. A loud moan escaped him as he filled me up.

A moment later, he slapped my ass hard. Master Boss wasn't pleased with my antics.