My First Anal Experience SeXStoRY

This is my first story. I have read a lot of them on here and wanted to finally add my own. I was flying home from visiting friends and I a=had a layover in Atlanta for 2 days. I was in my room and very bored so I started looking at porn on the internet. I was getting myself really excited and wanted to see if I could find anyone to hook up with. I went to craigslist since it is a free site and there are always people looking. I was browsing through the adult classifieds when I accidentally clicked M4M. I did not mean ti since I had never though about guys this way before. Before I could hit the back button the page came up and there were a few posts with the yellow image icon next to them. I let my curiosity get the best of me and I clicked on the first one. It was a guy looking for someone to blow him but it was the pic that caught my attention. It was a waist down shot (typical on craigslist) and it was about 7 inches and looked pretty thick. I just sat there wondering how that could go into a guys ass. Before I realized it my cock was really hard. I never though of it before but I started to get curious as to what it would feel like to be with another guy. I brushed off the idea and got up to get a shower. I peeled my clothes off and got into the shower. The water was warm but did nothing to lessen how horny I was from that one craigslsit post. I kept soaping up my body but kept running my hand over my cock and playing with it. I thought about it a lot while finishing up my shower. By the time I was done I decided to post an ad and see if there was any response to it. I typed up an ad and let the world know I was looking for a first time encounter with another male and that I was really nervous. I posted a pic and submitted it. WM looking to explore M4M for the first time. I am 5'11" with an athletic build, I also have trimmed body hair and am a little nervous since this is my first time. While I was waiting to hear something back from it I went downstairs and got something to eat at the restuaraunt. When I came back to my room I logged into my computer and was shocked to see around 30 emails looking to have fun. I was amazed that there were this many guys interested in hooking up. I carefully read over the emails and got hard to the pictures that were sent to me. I was slowly massaging my cock as I read through them all. I responded to a few and others I deleted either because I wasn't interested in what they said or I wasnt turned on by the email. After talking to a few guys I found one that I was interested in because he was in a hotel that mine shared a shuttle with so I could catch that over there (since I didnt have a car). We talked a little more and decided that I could come by later that night after his business meeting was over. I was excited the rest of the day and it seemed like days but it was only a few hours. I went downstairs to wait for the shuttle and when it came I felt my heart start to accelerate. I got on and sat down near the back. I told the driver where I was going and added that I was meeting some friends for drinks. We pulled up to the hotel and I nervously got out. I didn't know if I could go through with it but decided to let my cusiosity overtake me. I got onto the elevator and went up to his floor. The doors opened and I was getting more nervous/excited. I walked down the hall until I was standing outside his door. I was so nervous I could barely knock on the door. When I finally built up the courage and knocked there was a brief wait and the the door opened. I stepped inside and he was wearing the white bathrobe that the hotel supplied to its guests. My heart was beating a million miles an hour and he could tell that I was nervous. He was in his early forties and stood 6 feet tall. He had light brown hair and a little bit of chest hair sticking out of the top of his robe. He was a very handsome man. He asked me what I wanted to start with and I nervously looked down at his crotch. He smiled and said it was ok as he slowly untied the robe and let it fall away from his crotch. Hiw cock was flaccid and looked to be about 5 inches long and kinda thick. I knelled down in front of him and looked up at him. He was smiling and told me its ok to be nervous and to take as long as I needed to get comfortable. I slowly reached up and gently touched it with my hand and wrapped my finger around it. It was heavier than I was expecting it to be and I slowly moved my face in closer to it. I could feel his bl**d pumping and I closed my eyes and moved my lips to his head. The tip of his cock gently passed between my lips hs flaccid cock entered my mouth. It was incredibly warm and didnt really have a taste. It quickly became slippery in my mouth and I could feel it growing in my mouth. I was incredibly hard at this time and was masaging myself through my shorts. He saw this and grabbed both of my arms and mved them so that both of my hands were on his ass. As he grew more I was getting bolder and trying to see how much of him I could take in my mouth. He grew to about 7 inches and it was thick enough to make me worry how it was going to fit in some places. I was squeezing his ass as I started going faster and getting more excited listening to him graon and pant. I moved my hand over to his crack and gently touched his asshole with my finger. I was electrified since there were two very new firsts for me. He moaned some more and pulled his cock out of my mouth with a slurp. He dropped the rest of his robe on the floor and motioned for me to go into the bathroom with him. He turned on the water in the shower and climbed in. I quickly undressed and followed in after him. He was pretty muscular and had a light coat of body hair. He was lathering himself up wth soap and I couldnt take my eyes off his cock. He smiled and said I could continue and rinsed himself so that I wouldnt be sucking on soap. I resumed sucking his cock and rubbing a finger up and down hiw crack gently exporing. After what seemed like an eternity he stood me up and commented that I must really like doing it. I blushed a little and replied, "YES!!" he started stroking my cock and lathering me up wth soap. He turned me around and got down on his knees so he could see my as better. He slid his hand under my balls and into my crack and when he touched my asshole it made me shudder. He laughed and said soon I want it really clean down there. He rinsed me off and continued exploring. I was shocked when I felt him kiss my asscheek and then work his way over to my crack. He put his powerful hand on my back and bent me forward slightly opening myself to him a little more. Then I felt his tounge slidind up and down my crack and it was breathtaking. He gently flicked my asshole with his strong tongue and I needed more. I started moving back into his face and he stopped and said I think your ready. We got out of the shower and dried off. I walked into the main bedroom and laid on the bed waiting for him to finish getting ready. I was on my stomacj when he came in and started to slowly masage my back and legs. He spread my legs farther apart while rubbing me and then slid me on the bed so i was still face down but my knees were on the floor. I felt him spread my cheeks with his hands and his tongue slid in and out of my ass again. I was panting with desire this time. He asked me if I was ready and I begged for him to go on. I heard him opening something and realized it was a condom he was slipping onto himself. Then I felt the cool jet of lube squirt onto my ass. I could not control myself and was so excited my head was nearly spinning. He stood behind me and placed one hand on my hip and the other on his hard cock. He slowly traced it up and down my crack gently pushing on my asshole every time he passed. It was exhilirating. When the time came he told me to relax as much as I could and he was going to try to enter me. I felt him push onto my asshole and it was straining to go in. He stopped for a second and inserted a finger into my asshole and slowly worked his way up to three. It was slightly uncomfortable but it felt really good. He told me to relax again and he was going to try. As he pushed harder onto my asshole I could feel his cock slowly sink into my asshole little by little. He didnt g oall in one thrust but would back out and try again each time getting in a little farther. On his 7th or 8th try I felt the head sink all the way in and I was in heaven. I loved the way it felt in my ass and wanted more. He continued his slow pace and kept getting farther until he was about halfway in. It was still a little uncomfortable and he asked me if I wanted him to see how far he could get. All I could do was grunt in pleasure. He slowly slid all the way into me until I felt his pubic hair press againt my butt. I needed more and told him to go a little faster. He increased his pace and in a few minutes was pumping in and out of me pretty hard. I could feel our balls slap together and I reached under myself and started jerking my dick. He saw this and his free hand he moved around in front of me and joined my hand. I told him I wanted it hard and so he grabbed both my hips and thrusted hard itno me. It was a little painful at first but that pain quickly turned to pleasure. After fucking me hard lie this he pulled out and said he wanted to try a new position. I couldnt agree fast enough I ust wanted his cock back in my tight ass. He laid down on the bed and told me to get on top of him. I cimbed on top and slowly squattd over his cock. I grabbed the base and guided it to my hole and lowered myself carefully onto his cock. I sat all the way down on it and I tohught it was in my stomach. I started to grind my hips into him and he started to grunt and let out an "ohh fuck that ass is good" He started thrusting up into me and quickly increased his pace. He was holding ont my hips slamming into me while I was furiously jerking my dick. I told him that I was going to cum soon and he told me he wanted it on his chest without even slowing his pace into me. I felt my balls tense up and I started to orgasm and blow my load. I splattered on his chest and he let out a loud grunt and I felt his condom filling up with his cum. I just sat there for a minute feeling him slowy go soft in my ass. When I slid off him his cock just laid on his stomach. It was the most amazing sex I had ever experienced and I coundn't help but want it more. He told me my ass was incredible and wished I lived near him. After laing on the bed panting for a few minutes I got up and thanked him for tha amazing experience and walked out of the door back to my hotel room. I could feel the lube still dripping down my leg on the elevator and as I was going down I couldn't stop thinking how many more email were waiting me in my inbox........