Taking it to new heights

I met Tim from online in a m4m chat room. He traveled for his work often, he was 36 years old at the time, married, with three kids. His wife had no idea that he enjoyed topping college age bottoms while on his trips. He shared a fantasy with me about fucking a guy on the balcony of his hotel room in the open air. The intimate details he shared aroused me and I told him if he was ever in the area to contact me. I only had a picture of him from the neck down fully nude. He was smooth all over and expected his bottoms to be the same. Anal had to be bareback only, no kissing, just fucking. He didn't enjoy small talking either just sex and leave. Tim was all business.

I didn't chat with Tim for many weeks after he shared his fantasy until late one night he called me from a pay phone. He was going to be in a city near me about an hour and half away. Tim asked if I was interested in hooking up two nights away. I had recently started seeing a nice girl, Amy. We had been friends for a while and it had become physical. Amy said she wanted to keep her options open and I agreed. Amy knew that I was bisexual and I enjoyed getting fucked in my ass. I told Tim I could make it happen.

Later that evening Amy came over. We hung out watched a movie and took things in the bedroom. I was fucking Amy sideways on my bed. I was giving her my seven inch extra thick meat stick from behind. Amy liked to talk during the sex. I told her about Tim and what we had planned. Amy got aroused from my sexual misadventures. I grabbed her big saggy breasts. She had sexy tanlines from sunning in her skimpy yellow bikini. Amy could tan easily. She looked back at me wide eyed and smiled. I had given details of how it felt having an older man's cock in my ass. She reached back and grabbed my ass. "You are going to have a stranger's cock in this tight firm ass?" I liked it when she got excited and thus spurred me on to fuck her even harder. While I did try to get Amy to let me fuck her in the ass, she playfully denied me. I knew it was just a matter of time. When I told her the night I would be driving down to meet Tim in his hotel room, Amy asked if she could drive me down. We could get a room at a much cheaper hotel and take in the sights. I hesitated for a moment, but thought having company on the ride would be a good thing.

Amy and I drove down and checked into a seedy motel on the south side of town that afternoon. I wasn't eating anything that day and cleansed myself before we had left. I was only drinking water. I had shaved my body and Amy shaved my balls and cock area for me in the shower. It was such a rush having her use a razor on me. While I offered to shave Amy down there she preferred to keep herself neatly trimmed instead. We didn't have sex since the night I told her about Tim. I wanted to cum big if Tim would let me. Amy drove me over, having her talk about Tim and I was over stimulating. I normally processed it all in my head. With Amy, she made me even more nervous. I really didn't like her saying how easily it would be for him to throw me over the balcony since he was very muscular compared to me being lean and muscular. I never thought negatively about any of my hookups and began to rethink Amy tagging along. I stayed very quiet telling Amy, I was too nervous to talk to her. As we pulled up I was shaking so badly, Amy had kept talking and bad thoughts were inside my head. I actually thought about not getting out of the car. Then I thought the many time I had been stood up and I didn't like how it felt. Even though I had never met Tim, I didn't want to be that guy.

Amy kissed me and said she would wait for me in the parking lot. She had hoped to see me and Tim fucking on the balcony in the setting sun. I left and went to the front desk and gave Tim's fake full name. A young attractive woman looked at me suspicuously as I stood there shaking and sweating. It was a nice hotel, so I wore tan dress pants, my best brown shoes with no socks or underwear, and a nice light blue button shirt that matched my blue eyes. The woman called the room and gave Tim my name. She smiled and hung up the phone. I was given the floor and room number. I let out a heavy breath after pushing the number ten button. I leaned back looking at my reflection in the polished metal doors of the elevator as it went up slowly. The doors opened and I walked down the hallway to door. I took another deep breath to calm my nerves and knocked softly on the door. I rubbed my sweaty palms on my pants. No one answered I knocked again and still no answer. I began to think that even Tim had second thoughts about meeting me. He had seen fully clothed and nude pictures of me. He seemed to approve of me from telling me how picky he was. I knocked a third time and even leaned up against the door to hear if there was anyone moving around. I waited a couple minutes longer thinking he was in the bathroom. Just then the door behind me and across from the door I had been knocking on opened. There stood a fit muscular man, just an inch or two shorter than me wearing just a towel. He was bald, blue eyes, and smiling at me. I smiled back but still hadn't registered what was going on. He introduced himself as Tim and reached out his hand. Tim had a strong firm handshake that shook my whole body. He pulled me into he room. As he shut his door he told me I could remove my clothes. The lights were turned off and only the fading sun lit the room. It was a spacious room, a small kitchen area, a big bed, a table with two chairs, and the sliding glass door to the balcony was open as the curtains blew inward from the cool evening breeze. I removed my clothes, I was super excited and still nervous as Tim watched me undress. He liked I had no underwear on. His towel fell down and showed of his long slender cock. My thick cock looked much huskier than his but I liked how streamline his looked. We both were naked and Tim moved into touch me. He ran his hands over my body. I liked how easily he got my nipples erect. Tim let me touch him. His muscles were so sexy and his body made me jealous. I told Tim, he was the sexiest man I had ever seen. He laughed and thanked me. We moved out to the balcony and I admit, fear started to take me.

I stepped out and felt the cool air touch my naked body. Tim moved up behind me. He pressed his cock up against me from behind and reached around me groping me. I leaned back into him feeling his breath on me. I reached back and rubbed his toned hips. He made me feel so weak in the knees. Then I recalled how Tim didn't like to waste time. I turned around and went down on Tim. Tim looked surprised but didn't stop me. He was already rock hard and his cock slipped past my lips and easily down in my throat. I gurgled and bobbed into him. Tim placed his hands onto my head and looked down at me. I gave his cock a good layer of saliva. Tim complimented at how good I was. I kept going relaxing my throat and looking up at him. I would of kept going but Tim pulled back and said he was ready. I stood up wiping the saliva and precum from the corners of my mouth.

Tim gently turned me around. I spread my legs apart as he slowly fingered me. Tim didn't go all the way in with his fingers which felt amazing. My cock bounded up as more blood filled into it. Tim actually took it slow propping me. He told me my ass felt nice and tight and complimented me on my nice firm bubble butt. I was relishing how sweet he was compared to how business like he was online. Fingers were removed and Tim pushed his cock easily up into my ass. I moaned softly. His cock felt so amazing. I told him how great he felt. Not only was he hung, super fit, but so sexy. I held onto the railing as he slowly went in an out of my ass. Tim was breathing heavy and slow as was I and moaning. Tim shocked me being very vocal! He told me how good my ass felt and what a nice body I had. I felt my cheeks go flush in the cool air. I told him I couldn't wait to receive his seeds in me and cooed for him. Tim told me he liked the way I talked. As superficial as it might sound, I felt a deep connection to Tim even with his cock deep inside me. Tim asked if I wanted to try something more daring. In the heat of our passion, I agreed with a seductive moan. He pulled out, I let out a groan from the emptiness he left in me. He asked me to sit over the railing with my legs. I began to shake as climbed over with one leg, the bar now riding in the crack of my ass. The metal railing felt cool. I gripped the raining hard as I put my other leg over facing Tim. I looked at him shaking nervously. My bare feet slid under the railing as far as the could, my heels were hanging over oblivion. Tim looked at me and shook his head and helped me back over. I was grateful and hugged him thanking him. Tim thanked me at how willing I was. I breathed a sigh of relief and showed my gratefulness by going down on Tim. I gave him another coat of my saliva. The taste of my ass wasn't as bad, probably because Tim was extremely sexy to me! Tim had to stop me, telling me I was about to make him cum. I didn't mind if he would have. Tim had another idea. He stood me up and told me if I didn't want to do anything to let him know. I agreed and he turned me around. Tim slid his slender rod up into me. I moaned telling him how I had missed his cock in my ass. Tim pumped me a few times. Then he slipped his arms up under my own. My arms were straight up. He clasped his hands together behind my neck forcing me to bend over a little. Then Tim asked if I would be willing to put my legs up over the railing while he held me. I grunted from the awkward position. Then in a massive feat of strength, Tim picked me up as I hoisted my legs over the railing. My upper legs now rested on the railing. Tim's cock had slipped out as I pressed back towards Tim. Tim was breathing hard and unable to get his hard cock back into me. Tim released his grip behind my neck and I let out a terrified shriek. Tim could sense my panic, and told me that he had to let me go and when he did to grab the railing. It must of been quite a sight, two naked guys trying to fuck over a railing with one scared shitless nineteen year old and this much sexier man on a balcony. Tim released, I grabbed the railing and leaned back almost falling backwards! I was able to somewhat stabilize my balance as I swayed. Tim had me stick my ass back towards him. He pulled me back a little and reinserted his meat back into me. The feeling of Tim inside my poop shoot was reassuring. He moved his arms up under mine and clasped them behind my neck. He didn't try to push my arms up so I was able to grip railing. While a difficult position, he leaned me forward over the railing and fucked me faster now. I was forced to look down ten stories as my whole body was shaking. How my cock stayed hard and bounced up and down violently, I would never know. My grip was wearing out and I begged Tim to stop. I was worried what he might think but he pulled me back over. I was so weak in my legs I could barely stand. I was breathing to a point of hyperventilation. It was too extreme for me. I began to think what else could I do for Tim. Tim looked a bit fatigued himself. He too was breathing hard and in a blank stare asked if we could just fuck like we had been doing. I nodded and with shaking legs bent over and took Tim. He went at me like a jack rabbit. Tim rammed into me and let out a war cry as he shot his loads into me. Like a good bottom. When he pulled out, I crashed down onto the concrete and sucked Tim until he was satisfied. Tim asked me to leave. The look he had given was now cold as ice. I dressed quickly and hobbled down the hallway to the elevator. As I rode down his cum was oozing down my left legs. I am sure everyone who walked behind me as I left the hotel saw the dark stains in my pants. I walked out into the parking lot. Amy flashed her lights at me. I walked and she drove to meet me halfway. We returned to our seedy hotel where she washed me as I could barely stand. Amy took liberty sticking her short finger into my newly formed gape. It didn't arouse me in such a fatigued state...

Tim did reach out to me and thanked me for meeting him. I apologized for failing him and told him my ass would always be his if he wanted to claim it. Like with most guys I had met, we chatted online a few more times before he closed his account and I never heard or saw him again. I replayed the scenarios with Tim in my mind and wished it had gone smoother. Still, I really did enjoy getting used for a cum dump!! I liked how cheap he made me feel after the fact.