Tease: A sexy business man was charmed my pants off online and did a lot more when he was in town for work
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. 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. 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.
In the final days, his conversation had gotten very specific about what he liked and how he wanted our first meeting to go. It was thrilling to hear him explain the passion he envisioned for us. He informed me that he appreciates a boy who plays the role of a slutty son. Knowing that wouldn't be a problem, I couldn't wait for him to arrive. His hotel wasn't too far away and I wrapped up everything that I needed to do that week so that I wouldn't have any distractions. We had only discussed the first night, but I wanted my schedule to be open in the hopes that our time together goes well. After class that Friday, I went home and started getting ready. I made sure I didn't have any rogue body hair so that I could be the smooth boy that he wanted. I took a long shower and washed myself inside and out. I had picked out my clothes to match what he wanted with slacks and a nice shirt to appear as a preppy boy. It took all I had to keep my composure as I drive to the hotel and walked to his room. I carried a small gym bag that contained a change of clothes and some toys just in case he wanted to use anything. I was trying not to seem too eager, but I was so turned on that I wanted to be on my knees when he opened the door. Thankfully, he didn't make me wait very long.
It was a nice, quiet hotel and I found his room easily. There was a moment when I knocked that I feared some sort of trick to be revealed when the door opened, but I have to admit that it was a little thrilling. My fears vanished as the door opened and my dream daddy stood in front of me in business attire. He graciously invited me in and we exchanged pleasantries for only a couple minutes before he pulled me in for a kiss. He was strong, passionate, and a very good kisser. His hand was on the side of my neck as we locked lips and my hand went to run through the short salt and pepper hair on the back of his head. I instantly lost track of time. Holding our embrace, he moved me to the bed and laid me down. He pulled away so that he could watch as he unbuttoned my shirt. He began feeling my chest as soon as it was exposed. 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.
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 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 boipussy 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.
I was told to hover again and lower myself onto him so that I could take my time and accept him inside me. He lined up his covered cock as I eased myself onto him. He popped inside me as I moaned and he reminded me to go slowly. My legs were spread much wider than his and me hands were on his thighs to help hold my position. I moved about as slow as I could with all the excitement. I pushed up and dropped down taking him just a tiny bit deeper with each slow fall. My back was arched, head back, and I was moaning from the electricity building between us. It felt like he was almost too big to fit inside me and I could feel his length driving deeper and his girth pushing me open. I was surprised at how little it hurt at first, but as I lowered myself more, the pain started to increase. It wasn't going to be easy to take him deep, but I was determined to take as much of his beautiful cock as I could. He remained motionless this entire time except to sip his drink. My moaning became more labored with each time that I impaled myself on him. I had actually practiced this with a dildo suctioned to a tile floor several times, but having a real, hot, hard cock to fuck myself on was much more exhilarating. Moving slowly, the pain and pleasure swirled together resulting in an intoxicating euphoria. At long last, I fell until I was sitting on his lap. After a few seconds to allow my insides to adjust to their new guest, I began grinding on him to make sure I was feeling him as deep as he could possibly go. Another minute of this allowed me to really relax and accept his girth. The pain started to dissipate and the pleasure took over completely. He felt amazing deep in my gut. He was still hard as rock, but I was a little surprised at the lack of noise from him. He just let me continue fucking myself while he enjoyed his scotch.
By the time he told me to stop, I was fully erect myself and dripping precum onto the floor. He wasn't allowing me to go any faster, so the pleasure was slowly building. I knew if I would have continued for another minute, I probably would've shot a hot load across the room. We both stood up and he positioned me facing backwards on the chair, knees on the seat, holding my butt in the air for him. I could tell that my tight hole was still stretched open as he positioned the bottle of lube and injected me with an ample amount. I jumped a little and tightened up at the feeling of the cool gel. Seconds later his head pushed me open again and he drove into me with a steady determination. His hands grabbed my hips to pull me closer and within a few steady thrusts, he was as deep as he could go. I was moaning instantly as the pain of his penetration flared and then subsided. Each thrust took several seconds and were as consistent as if he had a metronome to keep pace. After a minute or so, his hands began exploring my body. I felt his strong fingers run up my back and cup my shoulder while his other groped my ass. This led to him running his fingers through my hair, reaching around to feel my chest, and stroking my cock just enough to see how hard I was. I had found a comfortable position with my head and arms resting on the back of the chair. My knees were spread to meet the padded arm rests, so I could just relax and let him have his fun. As the excitement built, I started gripping the chair harder and I could feel an orgasm creeping up.
He was hitting several spots inside me that forced my cock to stand at attention. The slow friction inside me was pushing me towards a very large climax. I was fighting the urge to cum as I wanted to relax and let it build even more. I wasn't touching myself because I wanted it to be purely from his fucking and for him to know that he alone caused it. I was moaning louder as the moment approached where my back arched, head went back, and I started screaming. My hands were gripping the back of the chair and I was surprised when I felt his grip on my throat. His pace never changed, but just as my orgasm reached the tipping point, his hand cut off most of the blood to my head and I exploded like a volcano. The feeling was something entirely new to me and it was one of the hottest moments I had every experienced. The combination of his cock grinding inside of me and the unexpected choking pushed me to an orgasm that felt like it lasted several minutes. He knew exactly how to extend my pleasure to an extreme that I never thought possible. He had started to moan as well and was letting out some gasped words, but I was oblivious to anything except what was going on inside me. Once my excitement was in full swing, he must have enjoyed the constrictions around his shaft, because his cock pumped out against me and he began to shoot. I was still in complete ecstasy as his grinding and my tight ass milked his cock to completion. I swear I didn't finish my orgasm until he was done shooting.
Once my orgasmic convulsions subsided, I relaxed back to my resting position. He withdrew slowly from my stretched, wet, and well-used fuck canal. He composed himself and allowed me to take my time getting up. The small talk at this point was mainly him saying how great I felt, that most boys can't take him deep, and that we were going to have to go again shortly. I contributed little to the conversation as I enjoyed my post-fuck cooldown. My eyes were closed, but I could tell that he was moving around the room. I heard his glass clink on the table and some other rustling as he picked up our clothes. My body felt stiff when I finally decided to stand. I heard the shower turn on and decided that a rinse wasn't a bad idea. For the next hour or so, there wasn't much talking. We cleaned up, dried off, had a drink, and laid on the bed watching TV. He was checking me out the entire time and I knew he liked having a naked boy in his room. I waited for him to let me know that he wanted to play again instead of jumping him as I wanted to. He had a very commanding presence that made me want to please him in any way I could.
We spent the entire weekend together. I only went home to grab more clothes so that we could go out to eat. He took very good care of me and in turn, I made sure that he was satisfied the entire time. I made his cock explode at least a dozen more times and with the help of a little blue pill, he spent hours fucking me. His techniques were a little different than I was used to, but he showed me what years of experience had taught him. I was on cloud nine for days, though I wasn't sure my hole would ever be the same. I've seen him about once a year since then with him coming to San Antonio all but the one time he flew me out to see him in another city. We text ever now and again and sometimes talk on the phone. We always enjoy our time together and try to spice it up with each visit. He is a very demanding daddy, but I manage to keep him completely satisfied when we're together. In turn, he likes to take me to nice places and buy me little gifts. My time with him always feels like a nice vacation.