My First Encounter with a Straight Dude

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This story just happened a few months ago in late February 2009. I was away on business in Kansas City. It was snowing outside that evening and I was done with business for the day so I had dinner and decided to check out who was on line. I logged into one of my favorite chat rooms, where I have had my most success with finding a mate for the evening, but it was looking kinda slow. I had chatted with a few locals but they had all decided to stay in for the night to stay warm and dry. I was just about to call it a night myself when this guy pops up a chat window and says 'Hey there'.

I don't normally respond to people who have no profile but I thought 'What the hell, I am stuck in the room so Why not?'. I responded with Hello and we chatted for about 20 minutes pretty much about the weather and how we both wished it was a little bit dryer. My curiosity finally got the better of me and asked him how come he has no profile. He replied that he is not out at all and was new to that site. We chatted for a while longer and I finally asked what brought him to chat with me. He replied that he has been having dreams about being with a man but has never been with one.

He said he was married, enjoys sex with his wife, but feels something is missing and wants to find out what it is. I asked him what he thought he wanted to do with a man. He replied that his dreams have all been about a man taking control over him and he ends up being the bottom. He also said that scares him as he doesn't want to be looked at as a non masculine man. I quickly told him being top or bottom isn't what makes you masculine or not and to get that thought out of his head.

I could tell he was very nervous by his words so I tried not to be a pig and get him into bed though I wanted to very badly. LOL I asked him again what attracted him to me and he replied that he was getting turned on by the pictures he saw and profile he read about me. I asked if he had done anything to prepare himself for taking a cock up his ass and he replied 'Oh Gawd No, I would never do that by myself'. So I asked what did he want from me tonight and he said he didn't really know. Well I told him that I don't connect with guys I haven't seen or know anything about. He replied with his stats of, '6'2", bln/blu, 195lbs, white smooth swimmer's body, and 29 years old. I replied back with mine but he already knew that but I also told him that I was old enough to be his father. He replied that age was not important to him at this time and asked if he could come over. I told him I still haven't seen any pictures of him. He said he didn't have any but would make me a deal. We could meet somewhere public and if I didn't like what I saw we could just say thanks and go our separate ways. I was going to say no as I have tried this before and they rarely turned out good but I thought to myself I am not doing anything else this evening so told him ok and gave him the address to the hotel and time to meet.


We had decided to meet in the bar for a drink and I of course got there early so I see if I could pick him out when he comes in. The bar was quite busy that night and there were a lot of young people hanging out laughing, drinking and having a good time. I ordered myself a drink and was about done with it when I decided that he probably wasn't going to show up.
Just as I had finished paying the bartender and was about to get up and walk out I noticed this guy standing near the bar entrance looking at me. He matched the body description to a "T" so I motioned him over to the bar. He quickly said he was very sorry for being late but when he got to the hotel he kinda froze up in the car. He finally got the nerve to get out and come into the hotel but had decided he was going to come in and politely pass on the evening as he didn't think he could go through with it. But once he got to the entrance of the bar, he saw me through the mirror and then was afraid I wouldn't like him and he froze up again. That is where I noticed him and motioned him over to the bar. I told him that just because we decided to meet didn't mean we had to go through with everything.

He seemed to calm down just a bit so I called the bartender over and we ordered drinks. We must have just sat there and chatted about nothing for about 3 hours as it was no close to 11pm and I had an early morning meeting but wasn't too concerned about that at the moment. I was enjoying our chat and he, though he wasn't drop dead handsome, was a nice looking young man. I wanted to reach over and rub my hand along his leg under the bar but I had to remember that this guy hasn't done anything like this before. After about another 30 minutes and about 3 more drinks he asked if it would be ok if we continued our conversation in my room. I said sure and we headed off chatting as we went.

Once we got to my room I noticed that scared look had come back into his face and I said don't worry we can just continue to chat if you like. He said OK and I opened the door and we went inside. No sooner had I closed the door that he asked if it would be OK if we hugged and I said sure. He walked slowly up to me and shyly put his arms around my body and slowly pulled me close to him. I slowly moved my arms until I was holding him tightly but I could feel his crotch bulging and it appeared the man was gifted down there. I wasn't sure what to do next but I remembered he stated that in his dreams a man took control over him so I slowly moved my hand up his back caressing it as I did until I came to the back of his neck. He had started to tremble a little so I took the back of his neck and moved his head until we were face to face.

He had closed his eyes so I moved in and placed my lips onto his and he slowly opened his mouth. I dove my tongue into his mouth and he let out a soft moan and tried to return the favor as his arms tried to pull me even closer to him. He was trembling even more now so I moved us over to the sofa and sat him down next to me. He opened his eyes and said thank you that was very nice and I really enjoyed it. Without thinking I reached down and placed my hand on his now ever so present bulge and he jumped a little but quickly put his hand over mind so I wouldn't remove it. I went back down into his mouth and pushed him back on the sofa as I started moving my hand up and down his shaft only to hear more bits of moaning from his lips. I reached back with my other hand and turned off one of the lights to make it a bit more darker and then, with our lips still locked, pushed him down on his back on the sofa.

He didn't resist that time so I moved my free hand down to his belt and unbuckled it and then unbuttoned his jeans and he cock tried to jump out of his underwear and I quickly placed a firm grip on it and he let out a small yelp. About this time he has finally gotten up enough nerve to unbutton my shirt and was rubbing his hands through my hairy chest. I reached to pull his pants off and he said wait a minute. He didn't want it to be one sided and moved down and undid my pants and felt my throbbing cock through my own underwear. I told him things didn't have to happen at the same time and to not worry about it. He said ok and then reached into my shorts and pulled my cock out with one tug. Well I thought I would shoot my load right then as his grip was firm and warm. I went back to my business and pulled his pants and shorts off and then pulled the rest of my cloths off. He laid there with a big smile on his face so I told him lets go into the bedroom where we will have more room. He jumped up quickly and followed me into the bedroom where I just grabbed him and pushed him down onto the bed. Before he could say anything I got down on my knees and quickly took his shaft all the way to the back of my throat and he let out a gasp and I thought at that moment he was going to blow his load. I let up for a moment and then slowly started working my tongue over his quivering purple head and then would swallow his cock until I would almost choke.

He would moan and make little comments like 'OMG, I have never felt anything like this before' and that would just make me want to pump his cock with my mouth even more. Well I kept my mouth over his cock for what seemed like twenty minutes and his moans seem to grow louder with each bit of pressure I would use. I finally came up for air and all of the sudden he shot his load all over my chest. He popped up with surprise and started telling me how sorry he was but when the cool air hit his extremely warm cock he couldn't stand it and just lost it. Hey I said no problem dude I am just glad you enjoyed it and then laid down on the bed next to him. He laid back down much more relaxed now and again started rubbing his hand through my chest hair that is now covered with cum getting it on his fingers and spreading it around.

I was ok with him getting off and was ready for when he decided he had had enough and would want to leave. But that didn't happen as he leaned up and started kissing me and at the same time his hand drifted down my body until it rested on my now jumping cock. He paused for a moment and then while still trying to get his tongue down my throat started caressing my cock slowly He was new so wasn't quite sure what to do so I moved my hand down on top of his and assisted in showing him how to move and touch. It didn't take him long to get the hang of it and he even started moving down my body with his lips kissing and nipping as he went. When he got down to my crotch area he seemed to pause for a moment and then opened his lips and slowly slid them over my purple head and down to my balls. Well I was about to lose it myself and he seemed to sense it and started moving up and down faster and tighter with each move. I just couldn't seem to hold on any longer and let out a very loud moan and all of the sudden it was there. I was cumming in his mouth and he was gagging but didn't come up for air.

It seemed like I had just let go of the biggest load in quite some time but he held tight until I finally quit pulsating. When he finally came off my cock I told him I was sorry but it happened so quickly I just lost my mind. He replied back with that wasn't all I lost and then gave me an evil grin. He climbed back up to where I was on the bed and we just laid there for a while. He finally spoke up and asked how long was I in town and I replied back just a couple of days. He came back with so was he and I said I thought you lived here? He said that question never came up but he was also on a business trip. We both laughed at it and then he said do you think it would be OK if I spent the night? Well I rarely spend the night with one of my tricks but he was a special case and this meant the potential of my cracking his ass for the first time. Damn that was a very hot thought and I quickly told him sure that wouldn't be a problem.

He jumped out of the bed and put on his clothes and said I will be right back as I have to get some cloths out of the car. While he was gone I cleaned up and when he came back he went into the bathroom to clean up. When he came back he jumped back into the bed, leaned over and kissed me again, and said thank you for taking it slow with me and I have had a really good time. And with that he said could we go to sleep as I have a big meeting in the morning and I replied so did I and I turned off the lights. We both got under the covers and he snuggled up next to me so I put my arms around him and started caressing his back. He whispered softly how good that felt and within a few minutes he was fast asleep. Well my cock was starting to jump to attention again but I knew I also had an early day but I couldn't help remember that I haven't had a touch of that ass yet. So, I slowly moved my hands down his back slowly massaging as I went until I hit the mound. And what a mound it was, so well defined as I moved my fingers across each cheek and losing them in between and resting at the entrance. One little push against the tight pucker responded with a twitch but I knew I had to quit as I didn't want to scare him to death by just jumping on his ass and taking it. I slowly caressed his back with my hands again and he rolled over and placed his head on my chest.

I was about out myself so I gave up and closed my eyes. The next thing I know I am hearing this guy telling me to get up man. I opened my eyes to see him almost dressed telling me he is almost late for his meeting. I looked over at the clock and said oh shit what happened to the wake up call. Needless to say it never happened and I jumped out of bed and ran for the shower. Just as I was about to step into the shower I thought wait I need to at least tell this guy goodbye and perhaps we can connect later. But right at that moment I heard the hotel door open and close quickly and I knew I had lost my chance. I thought ok perhaps he will be online tonight and I can check with him then. I went back into the shower, got dressed as quickly as I could and headed out the door to my meeting. I couldn't help thinking about the night before and what could have happened didn't but had to quit thinking about it as I was now late and my cock was trying to wake up again.

I get to where I am going, jump out of the car, and run into the building looking for my meeting room. I find the room and can hear voices already and know I am now officially late. I opened the door as quietly as I could keeping my head down as to not draw attention to the back of the room. There are about 50 people in the room so I quickly give the room a look over to find an open seat. I find only one and quietly head straight for it. I sit down quickly and let out a small sigh of relief when the guy next to me leans over and says glad you could make it. I look over and it is the same guy I just spent the night with. We both smiled and tried to get back to the meeting topics. We decided at lunch that we would get together for dinner later.
Watch for the next episode of the night of dinner and if anything happened later.......