I live a pretty simple life. Standard job, family, etc, and its all good. I'm not complaining, but I do get a little bored sometimes. What is it they say about idle minds?
A few years back, I was traveling for work and staying in a hotel in Austin, TX. After a long three days of work, I returned to the hotel on Friday night around 8:00 p.m. I was a little tipsy from the business dinner, and after three days on my own I was more than a little tired of sitting around at night. So I popped open my laptop, checked in at home, and started reading the news. Soon, however, I found myself browsing Craigslist's casual encounters section. I go there sometimes when I'm horny and bored, and I often fantasize about doing something outrageous. I also happen to have a discreet little bi side, and while I don't get into snuggling with guys, there is something mysteriously attractive about a guy's dick. As I was clicking on the posts, looking for someone who was not an obvious troll, I found one where there was a guy looking for a blowjob. His post was short and simple, he was about my age, and for some reason I responded to his post. I figured I wouldn't hear back, and it gave me a thrill just to pretend we would hook up. I mean, these guys get a million responses, right?
He responded five minutes later.
He was a tow-truck driver, done for the night and heading home. He offered to come to me, said he was safe and discreet, and that he had only done this once before. He was married, but his wife didn't like to give him head. He said he could be at the hotel in just a few minutes, and he would love a blowjob. He also said he might give me one too, but that he'd never done that before and he definitely wouldn't swallow. What he really wanted was for me to swallow.
My heart was beating a little faster now, that's for sure. As if on autopilot, I found myself responding. Yes, I said, I'm safe and discreet. Yes, I like to give head and I love to receive it. And swallowing? Maybe, but I don't know.
And with that, I gave him the room number, hit send, and then wondered what the hell I was doing.
I didn't hear anything back, and after a few minutes I decided he probably chickened out and was headed home. But about ten minutes after I hit send, I heard a quiet knock at the door.
I almost didn't let him in. This was crazy. I didn't know this guy. But the thought of giving a guy head ruled the moment, and I opened the door and let him in. His hands were in the front pocket of his hoodie, and he wore blue work pants and big black shoes. He was about 6'2", a little taller than me, and about my age. He seemed quiet and nervous, like me. We talked a little, asking each other if we did this much, are you sure you're safe, and that sort of thing. Then he said, "Well buddy, it is getting late. Its either now or never. Are we going to do this?"
I nodded my head, dropped to my knees. He approached me, and I unbuckled him and unzipped his pants. I reached into his pants and pulled out his cock, which was bigger than I expected. It was heavy, a little musty, and really thick at the top. It looked a little like a baseball bat. I could see how his wife might balk at the idea of blowing him, but at the same time it was a powerful looking tool. I grabbed it with my hands, and he moaned "That's right, suck it."
I took it into my mouth as he got hard. Salty, sweaty. I had no idea what I was doing, but at least I was enthusiastic. I took as much of it into my mouth as I could, and starting giving him the best blow job I could muster. It wasn't easy, as he was really thick at the top.
After a few minutes of me on my knees, he started to get more comfortable, and so did I. I slid my own pants down, and started jacking off. He moaned his approval. He asked if I liked sucking his dick, and I muffled a "mmn hnh" and kept going.
Suddenly, he pulled me away and said, "Fuck it!"
He pulled me up to standing, then he leaned over and he grabbed my cock (which was still in my hand) and started blowing me. I was so into blowing him, I didn't realize how horny I was. I felt the rush of an orgasm building almost immediately, and although I tried to fight it, I knew it was no use. I told him I was about to cum, hoping he would decide to swallow, but he didn't. He pulled my cock out of his mouth and jacked it as I spurted four times all over his hand.
Some of my cum fell on his shoes. I could tell he wasn't thrilled. He said, "Fuck, man, that was fast. And you came on my shoes." Then he gave me a slightly diabolical smile and said, "You'll have to make that up to me!"
He took off his shoes, and then his pants completely.