Not long after I turned 18, I met a very nice older gentleman online. I have always liked a variety of looks and older men can be very hot. I especially like a well-dressed, professional, up-scale, experienced man who knows what he wants. This is exactly what I found. I had signed up for a few different hookup sites and had been talking with several guys when I got a message from one that made my jaw drop. His pictures were like Clooney, Pitt, and Neeson combined with all the sexual allure you could imagine. His profile told me that he was 55, lived a different state, traveled often, was married, a top, had years of experience, and enjoyed the company of younger guys. I immediately thought that he was a fake, as many are, but decided I'd chat with him anyway.
He told me that he would be coming to town for a week and wanted to make a new friend. I was enjoying the conversation and he seemed genuinely interested in me. I have to admit, he knew how to make me melt. After about 20 minutes of chatting, he offered a video call so we could both see each other. The flirting continued as he told me that he wanted to make sure I was real and that I seemed too perfect. While chatting, I had been staring at his picture and hoping that he looked anything like it.
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I was pleasantly surprised when I saw him on camera. He was well groomed and I could tell that the pictures were real, though professionally done. He was in a hotel room in another city.
Even though he wasn't dressed up, I could tell he wore his confidence all the time. He told me a bit about what he does and that he didn't typically visit San Antonio, but there was a business need. I honestly didn't care why he was making the trip as long as he had some free time. He talked me into doing a little strip tease for him in exchange for him showing me his cock, which looked amazing at around 8 inches, a decent girth, cut, with a perfectly shaped head. By the end of the call, we had made arrangements to meet the following Friday at his hotel.
We continued to message each other before he got to town. The conversation was only getting hotter and the anticipation was killing me. I had been fucking a friend of mine for a few weeks at that point and was honest with him about it. He was very understanding and let me know that he had a boy in the city he was currently in that he was seeing. He even went to the extent of calling me to describe in great detail what he had done with his boy a couple nights before. He had me fingering myself and stroking while he led my imagination to a very nice climax. Once I had finished, he shot his load while describing how he had passionately fucked his boy and then cum all over his ass and back.
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We were still a few days away from meeting, so he told me that I should go see my friend. He only requested and I tell him all about it the next day. Doing as I was told, the following day I got to tell him about being fucked deep in several positions before he ripped off the condom and used my throat to finish himself off. We were learning about each other's preferences and he particularly liked how enthusiastic I was about each sensation.
We came at about the same time and it was exhilarating to hear him moan while he shot. I only wished that I could have been there to receive his seed. He later told me that he would have liked to watch me getting fucked by another boy.
He was moving slow and keeping my complete attention the entire time. He left my shirt on and mostly tucked in as he kissed me again while feeling my flat, hairless chest. Speaking in very soft tones, there some small talk about how badly we wanted each other. With that, my hand gravitated to his crouch to feel his cock through his trousers.
He let me rub his bulge for a minute before he moved to sit in an arm chair that was next to a table. He had a bottle of scotch and had already poured himself a drink. He sat back in the chair and motioned for me to come over. I tried my best to seductively crawl off the bed and over to the chair. His legs were spread in relaxed fashion and I could see that his bulge was growing. I ran my hands up his thighs to meet his manhood. I slowly unbuttoned his fly and discovered that there was nothing but that thin material between me and his cock. I reached in, took hold of his shaft, and gracefully pulled him up and out. He was mostly hard at this point and he looked amazing. The only instruction he gave me in the moment was to go slow.
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I began by licking him from the base to tip along the bottom of his meat before wrapping my lips around his head. He as pretty big, so it was probably for the best that I was taking my time. He was silent as I felt him getting harder in my mouth and hands. I barely even noticed as he sipped his drink and at one point even checked his phone. We were both still clothed and I think that added to the erotic feel of us connecting. He was rock hard and I was enjoying playing with his very powerful penis. He was glistening from my saliva and the veins popping out showed that he was fully engorged. I went on for at least another few minutes before he told me to stand up.
He sat with his drink and told me to strip for him. I moved my hips in a swaying motion as I took my shirt off. As that fell to the floor, I spun around to show my ass in slacks. I backed up and started slowly grinding on his erection. His breathing was getting heavier and I knew he was enjoying himself, but he couldn't tell that my little fuckhole was twitching with anticipation.
While bent over, I worked my pants off and showed him my bubble butt for the first time. I made sure my pink boy pussy was exposed so he could see how clean and smooth I was. He instructed me to get the lube and condoms from my bag and I happily pranced across the room to retrieve them. I handed him the bottle and was told to turn around, bend over again, and hover my ass above his cock. I immediately felt his fingers on the small of my back as his thumb landed on my hole.
I was concentrating on remaining still, but couldn't help closing my eyes and moaning as he worked his thumb around and began adding lube. He liked to take his time and he made sure there was ample lubrication around and inside me before we moved on. He had me take his trousers off as he removed his shirt. Things were about to get hot and heavy. He put on a condom as I awaited instruction.
