I spent a few hours on the plane thinking about my exploits, and looking forward to having a little fun once the day's work conference ended and I was comfortably back in my hotel.
I had long since come to terms with the fact that my voracious appetite for sex knew no gender bounds. My first encounter had solidified that. I smiled to myself how slutted out I had been that night, my mouth clumsily stuffed with cock before eagerly offering my ass to be plowed. I shifted in the cramped airplane seat to adjust the erection that was growing, thinking about how on a night that would have been filled with mediocre video game play and cheap beer, I instead had driven home with a sore jaw and a slightly sore backside. If one thing that night had proven, it was that I liked the surprise aspect of the whole affair: Zero to cock-whore in 60 seconds flat. Such was the nature of online hookups.
Still, I had unanswered questions about that night, and how I wanted to channel this sexual energy of mine. Being the first time that I sucked cock, my attempt while genuine was as awkward as one would expect. He was gracious as I tried my hardest to get him off but was unable to. I had offered my other hole as a show of bravery. I thoroughly enjoyed the primal thrust and the swelling of his shaft when he shot his load deep in me. It was an intoxicating feeling, but I had not done it again. I certainly wasn't out of pain or fear, rather a lack of motivation.
And that's the thing about me: I always have to do things twice to make sure the first time wasn't just a fluke. While I didn't necessarily want it to be an everyday occurrence, I wanted to have my mouth and anus stretched with CONFIDENCE, not out of curiosity.
So, I had my mind made up as I sat down at my laptop after the workday and prepared the ad I was going to place. I needed at least one of two things to happen. One, I wanted to finish a guy off with my mouth. Spitting or swallowing was never a doubt, though. If you're going to suck someone off, you should go all the way. Two, I was going to get penetrated. I had played with toys in my own ass enough since that first time to know I could handle it. If I was lucky, I would come across someone who would give me two for one shopping. But as I sipped on the wine that I had grabbed on the way to the hotel, I knew I would be satisfied with either one.
The first hour or so drew no interest. The second hour, a few replies that were either too over the top to be serious, or two tepid to be interesting. I was about to log off and try to get some sleep when one came through that was interesting:
'45-year-old, married white male, closet cocksucker who wants to be told what to do. Will travel, no reciprocation if you don't want to.'
Intrigued, I replied back and told him a bit about myself. 48, Black, masculine, about 7 inches and ready for your mouth. I knew he was for real because he replied back in less than 2 minutes with a simple, "Sounds nice. Tell me where you are, and what you will have me do."
I felt a dominant streak come over me. Sure, the first time I had basically been a submissive all-holes fuckboy, but I suddenly became curious about playing the other role. I replied back:
"Be here at 10pm. You will come in, strip completely naked, get on your knees and await further instruction." He replied with a simple, "As you wish."
It was a pleasant surprise that he was so punctual. I had barely dried myself from the shower when I heard a knock on the hotel room door. He was exactly as advertised. 45 years old, with gray eyes, sandy blonde hair and a dad bod. He literally looked like an average Joe whose wife had no idea what he was doing. Joe may have been his name, maybe it wasn't. We didn't exchange names because neither one of us cared. He slipped off his shoes, jeans and shirt and knelt on the floor just as he was told without saying a word.
Dropping my shorts to expose my semi-hard dick to him I said, "Are you going to make this cum?" He nodded eagerly. I took the room chair and scooted close to him. Sitting down and spreading my legs to fully expose myself, I said, "Time to get to work."
I leaned back as he took my shaft in one hand and drew it to his mouth. Licking my head and stroking me, I quickly grew in his mouth. 'This is much better than I expected' I thought to myself as he took my balls and gently started to knead them with his fingers.