Chapter 14 - Calgary Trip
My boss had asked me to head to our Calgary location to train some employees on our new software. I helped with the implementation and was getting quite knowledgeable about it. I was the one who trained everyone in my office so it made sense that I would train them too. I had to travel the day before in order to be there early the next morning which meant I would have a lot of time for fun due to the time zone difference. As the plane descended, I looked out at the city below, feeling a mix of anticipation and nerves in my stomach. Some of it was about the training session ahead but mostly, I was thinking of the fun I was planning of having with some local guys.After a smooth landing, I maneuvered through the bustling airport, getting my suitcase before jumping into a taxi. The driver was friendly, pointing out local landmarks as we drove through the city. When we arrived at the hotel, the warm scent of fresh coffee greeted me in the lobby. The check-in was quick, and soon I found myself in my room where I could collect my thoughts before training my co-workers the next day. And, by collecting my thoughts, I mean finding a hot cowboy to fuck me. I had brought condoms and lube with me, so I was ready.
I unpacked quickly and opened the local M2M personals on my computer. Before placing an ad, I browsed through the ones that were there. I found a couple interesting ones and started a conversation with them. One had no pictures but the ad mentioned he was a hung top looking for NSA, the other did not have much text but included a picture of a nice hard cock. The first one replied quickly and asked what I was looking for. I replied, “Same as you. NSA fun but bottom.”, and I included a picture of my ass. It took a few minutes for him to reply, and I thought I had lost him but then, I heard the e-mail chime. It said, “I want to tap that. Can you host?”, and it included a few pictures.
He was everything I considered a cowboy to be. The first picture was of him fully dressed outside and someone had obviously been cut-out of the picture. From what was left, it looked like it was a woman and that it would have been a picture of them as a couple. The thought that he might be with a woman and secretly meeting with men, turned me on but what turned me on the most was how rugged he looked. He wore work boots, tight jeans and a tan swede jacket. He had a baseball cap on so I could not see his hair but he had a very handsome face with a thick red moustache and face scruff. If he had been wearing a cowboy hat, it would have completed the fantasy. The other picture was of his cock. Not fully hard but uncut, surrounded by reddish/brown pubic hair. I immediately imagined what it would look like fully hard and how it was going to feel inside me.
Of course, I replied tat I could host and sent him my hotel information and room number. He said to give him about 45 minutes as he was on the other side of town. I took a shower while I waited feeling very nervous for some reason. He had only seen a picture of my ass, what if he didn’t like the rest? I only put on a pair of gym shorts and a t-shirt; No underwear. I checked my e-mail while I waited and there was a new one from him. I thought he might have cancelled but no; It was an e-mail to say he was leaving his place. It said, “Leaving right now. Can’t wait to shoot my load in you.”. The thought turned me on but that was not what I had planned. I didn’t think he would look at e-mails on the way, especially since he e-mailed before leaving so I didn’t respond.
I was more nervous than before. How should I handle that? Do I tell him I wanted us to use a condom as he arrives or do I just let things play out and when it was time to fuck, ask him to put one on? I decided to tell him later, afraid to ruin the mood right away. I took the lube and condoms out and placed them on the bedside table to be ready.
It felt like hours before he arrived but when he knocked on the door, at the clock told me it had only been about an hour. I took a deep breath and opened the door. “Wow!”, I thought to myself as I said hi. He was dressed in a similar style as the picture, only darker. The jeans were black and the jacket was green camouflage. He looked even better than his picture. He was not wearing a hat and I could see he had a buzz cut that made him look even more masculine. He reminded me of those vintage porn stars.
I invited him in, and he looked to the floor as he walked in the room. He seemed a little nervous but for me, at least we were past the worry that he might not like what he saw. I closed the door and he grabbed me and pulled me into a kiss. “He’s not wasting any time!”, I thought to myself as I gave in to the kiss. He held me close and kissed me hard, almost making me weak in the knees. He was either very horny or didn’t have a lot of time because as we continued kissing, he lifter my t-shirt and we broke the kiss so he could slip it over my head. He threw the t-shirt on the floor and then slid both hands down the back of my shorts. “Hmmmmmm!”, he said, finding I was not wearing anything else. I felt very vulnerable having only one item of clothing and he was still fully dressed but that was about to get worse. He started to rub his finger on my hole and moaned again, then push down my shorts; when they went past my ass, they fell to my feel.
“Get on the bed!”, he ordered, and I did as I was told. I laid back in the bed as he started to take off his clothes; essentially stripping for me. Not like a real stripper, in fact, he seemed a little shy getting undressed in front of me. He started with the jacket, then sat down to take off his boots. Then he stood-up, removed his shirt, pants and underwear. I watched as he approached me but instead of laying down with me, he gave me another order, “Turn around!”, he said and I realized he was eager to fuck. I got on all four on the bed with my ass towards him. He grabbed my ankles and made me back-up to the edge of the bed in doggie position. Then, got on his knees, buried his face in my ass and started rimming me. His tongue was magic and he was as passionate at kissing my hole as he was kissing my mouth. I thought to myself, “The woman that was cut-out of the picture must be a happy one.”. Wow, he was good. He slurped my ass, digging his tongue into my hole making me moan like a bitch in heat.
"Like that?" he asked between licks, running his tongue along my ass crack. My body shivered all over, knowing what was coming soon so I replied, “Yes! Feels so good!”. When he was ready, he stood up and grabbed the lube off the nightstand and applied some on his cock and my hole. He pushed one, then two fingers in me before placing his cock head against my hole. When he applied pressure and his cock started to push in, I said, “Put on a condom!”, and he replied, “It’s OK. I’m just teasing you.”. So I decided to let him continue. He would run his cock along my crack and his cock head would catch on my hole. Then, he would push his cock slightly into me and return to sliding along my crack.
At some point, he aimed his cock at my hole and started to fuck with the head barely going in. He said, “Don’t worry. I’m not going to fuck you like this. I just want to tease your sexy ass.”, and that gave me the confidence to let him continue. He kept pushing his cock against my hole and he was very gentle. He went back and forth in a fucking motion and I was so turned on by what he was doing, I barely noticed more and more of his cock was going in each time. When I realized more than half of his cock was in me, I said, “Not bare!”. He withdrew and said “No, no.”, and continued with just the head.
The same thing happened again. I shouldn’t have let him, but I did. He slowly pushed more and more of his cock into me each time only that time, I let him get further, much further. He moaned when he pressed his body against mine with his entire cock in my ass. I moaned too because it felt so good to have him in me but I was fighting my desire to let him fuck me bare. “That’s not teasing.”, I said and he replied, “I know.”, as he pulled out slightly. Instead of withdrawing from my ass, he pushed back in in slow motion. I let him do that a couple more times but then I realized, we were actually fucking bare. My sensible side took over and I said, “Condom!”, in a more stern voice.
He listened that time. He took a condom from the side table, rolled it on his cock and used some lube to get it ready. "Aarrrgghhhh!" I grunted, as I felt his cock go all the way in me in one rough push. He might have been gentle trying to get me to let him fuck me raw but since I had insisted on a condom, he was different. I buried my face in the pillows and let him start fucking me hard and in long strokes. "Ooohh yeah!" he moaned softly, holding my hips with his strong hands as he fucked, making himself at home in my ass. My own cock was rock-hard between my spread legs, leaking pre-cum as he kept thrusting into me. I let him fuck me deeper and harder as he drove himself in and out of me with increasing speed. He was making me take him all with every stroke. He would occasionally slap my ass as he continued fucking. Some of those slaps were as hard as his thrusts and my hole started to hurt. I felt my untouched cock start to lose its erection. After about 15 minutes of rough fucking, started to squeeze my hole to make him finish faster. I heard him moan about how he could feel my ass muscles contact and spasm around him and thought for sure he would cum inside me, or inside the condom at any minute. Instead, he simply yanked himself from my hole and physically flipped me over on the edge and of the bed. Then, he rammed himself back in balls-deep and resumed fucking missionary.
Lying on my back, I stared at him as he fucked me. Maybe it was the fact that he was so hot or maybe it was the new position but, it felt better. I laid back with my legs spread, as he shoved his hard cock in and out of my ass. He was also staring at me and neither of us stopped gazing at each other as he fucked me in that position for another 30 minutes or so. I enjoyed the fact that he seemed to be really into me and I noticed my cock was getting hard again. It was bobbing over my belly as I surrendered myself to the hot cowboy and let him fuck me as hard and deep as he wanted. He spat on my hole, adding more natural lube to keep me slick then, started fucking faster and harder pushing my legs back as far as they would go. It gave him even deeper access. “Oh,god!”, I groaned, stroking my hard cock, knowing it wouldn't
take long before I came. I wanted to get fucked, and fucked I was. I couldn’t hold it anymore. My orgasm rose from my prostate, through my whole body and down to my cock. I yelled, “Aaaaaarrrrrghhhh!”, as I shot a big load on my stomach. Some of it reached my beard but he was not done.
He leaned over me, his big defined chest looking very good. I reached up to pinch his nipple. He liked that and it made him to go fuck even harder. "Yeah, fuck! Pinch them!”, he ordered, as I started manipulating both his nipples. He groaned louder as his eyes rolled up into his head and he stated pounding me harder than anyone one had before. The fuck thrusts started to become painful again and I wondered if I had bitten off more than I could chew. I released his nipples, hoping he would slow down but insisted, he continued. I licked my fingers and went back to his nipples, pinching and twisting them in circles, adding some hole squeezing to get him to cum.
"Awww, fuck!”, he suddenly said closing his eyes, "I'm cumming!" he announced, never stopping his thrusts as he continued hammering straight through me with our bodies making loud slapping sounds. "Arrrghhhh!" he grunted as his cock thickened and swelled in my ass. He was a loud shooter and continued to yell “Arrrggghhh! Arrrggghhh! Arrrggghhh!”, each time he deposited more cum inside the condom.
When he was done, he buried himself, collapsed on top of me and stopped moving, allowing his cock to deflate inside me. He pulled out of me after a few minutes and flopped down on the bed beside me. "You are exhausting.", he complimented, saying “That’s some ass you got there.”. He pulled off the condom and I could see the tip containing a lot of cum as he left the bed and added, “Too bad I was wearing this.”, as he threw it in the garbage can. Then, he went to the bathroom and I heard the sink running. I looked at the clock and realized I had just taken the longest fuck of my life so I touched and fingered my hole. It felt a little sensitive but not too bad for tow hours of fucking.
He came out of the bathroom and caught me with a finger in my ass. “Ha! Didn’t get enough.”, and I pulled my hand away. “Just checking.”, I said as I sat on eh edge of the bed. I enjoyed looking at the hot guy who had just been in me a few of minutes prior. When he was done, he simply walked towards the door, said,” See ya!”, and I barely had the chance to say, “Bye.”, before he left.
I stood-up to go get cleaned up and glanced at the condom in the garbage can. It looked like there was a lot of cum in it, so I retrieved it. I thought to myself, "Enough cock for one night.", that’s when I heard my email chime.
