This is a story from a few years back. Turning 40 really caused me to reflect inward; on the outside I am a very vanilla, clean shaven conservative guy, 6ft tall, 220 lbs, with grey hair. I don’t stand out in the crowd, I am pretty much quiet, until I get to know you, but I realized my sex life was a lot like my outward image, steady, reliable, and predicable. In the world of commerce, that’s good—in the bedroom it’s frankly a bit boring.

As I begun my inward reflection, I allowed my self to start browsing various types of porn I wouldn’t have touched in my younger years. It was gradual, I moved from traditional styles of straight porn, to scenes that focused on threesomes, to mixes that included bisexual men, to finally gay sex. During the trip of self-discovery, I began to find out what turned me on and what I realized I was missing. I slowly began to desperately hunger for some sort of spice in the bedroom. To be fair, I am overwhelmingly attracted to women, I couldn’t even imagine having a romantic relationship with a man, but I began to realize that I could very well have sex with one.

Over the course of months, I met a couple whom pushed my boundaries (which I wrote about), but after they moved, like my porn habits, I began to fantasize about genuine male and male contact. Just like I met Dan and Debbie through craigslist, so I put out another ad looking for such an encounter. In this ad I asked for a specific type of encounter where I would be in control. I wasn’t into pain or humiliation, just open exploration from a heteroflexible point of view.

After I posted my detailed ad, I was flooded with a number of people who couldn’t read, just sent me dick pictures, and sent a three word reply; all of which I firmly said that I wouldn’t respond to in the original ad. In the ad I was clear about what turned me on and the type of scenario I was interested in. Eventually, Eric responded with a paragraph describing himself and recommending a couple of things he would like to try. Eric described himself as slightly younger, 34 also very vanilla looking guy without facial hair, slighter build and a bit shorter at 5 ft 9 in and weighing 175 lbs. He also made it clear that he ultimately identified as a bottom and was solely interested in making me orgasm.

Over the course of several weeks, Eric and I exchanged multiple emails, forwarded various clips that depicted what we were into, and finally agreed to meet at a local Starbucks near a hotel where I had rented a room. At the right time and place, Eric walked up to my table in the Starbucks and introduced himself to me. We both agreed to wear blue short sleeve shirts and cargo shorts so that we would recognize each other. Shaking hands he sat down while we both sized each other up over a cup of coffee surrounded by people going about their daily lives while the both of us were playing various porn clips in our heads of what was about to happen next.

After about 10 minutes of casual conversation, I was sold, and offered ostensible reason to the outside observer why we were leaving and why we would be headed over to the nearby hotel. I could tell by the way he walked and talked that the excitement was building in him, just like my cock was beginning to feel. By the time we crossed the hotel lobby and entered the elevator, my cock was beginning to drool precum and I was forced to reposition it several times. As we walked closer to the door all the time maintaining some sort of aloof conversation, I could tell he was caught up in it too; Eric began to mix up words and stumble over his sentences.

At the door, with no one in the hallway, I paused and looked him in the eye and said, “Are you ready for this?, Once we go in the room, I am not holding back you understand?”. Eric swallowed deeply, paused and looked me back in the eye and said he was ready. I took out my card, opened the door, and Eric when in first, I followed quickly behind him, locking the bolt and then turned to him pulling him into my personal space.

Firmly but slowly I pulled his face to mine and we began to suck face. I pushed his mouth open with my tongue and explored his mouth with mine. Quickly Eric returned the passion and we did this for a couple of minutes, all the while clenching each others asses and rubbing our cocks against each other while through our shorts. Finally I broke off and told him in a firm voice to get naked. Eric didn’t miss a beat, both of us quickly undressed and kicked off our flip flops. Standing there naked, I once again, pulled him in while we squeezed our naked bodies against each other and again started kissing.

Finally after a short while, I told Eric to get on his knees, he complied and found himself level with my cock, I didn’t need to tell him what to do next, because we both talked about this for some time. Eric began to rub his face into my crotch, using his tongue to taste my precum and at the same time use both of his hands to grasp my ass cheeks pulling my cock closer. In response, I reached down and lightly but firmly curled my fingers through his hair; looking down at him and told him to open his mouth.

In one smooth motion, Eric opened his mouth, slid my cock deep down his throat and pulled my ass with his hands. I replied in kind by pulling his head into my crotch and holding his head in place. His tongue and mouth began to work around my shaft as we both found a rhythm that worked for us. His right hand dropped away and I could feel the motion of him starting to furiously beat off his own cock while swallowing mine. We did this for maybe five or six minutes until I realized I wouldn’t be able to hold back any more.

Letting Eric know that I was about to cum, he moaned and started letting ropes of cum erupt over my feet as he pulled in my cock even deeper into his mouth. At the moment I came, a few minutes later, it was such a gratifying feeling to have the two of us focused on this one event, him swallowing everything I could give him and me making sure he didn’t pull away. I suddenly felt myself release down his throat, feeling his tongue milk my cock, his hands pulling my ass even tighter, me pulling his head to my crotch even tighter, knowing my cum was rolling down his throat. We stayed locked like that for another minute or so as my cock began to deflate.

I would love to say we did more that encounter, but the truth is that was all we agreed to that day. We quickly got cleaned up, dressed, and went about out day. We did meet up several more times, but that will be in later stories if anyone is interested in.