First Gay Experience with Older Man

One day feeling rather curious I decided to jump on a popular chat room service and see what was out there. For a while now I had been curious about what it would be like being with another man but never acted on it. So I went looked for the M4M chats. Needless to say there were quite a few so into order to narrow them down, I looked for rooms that pertained to the area where I live. Finally I found a couple. All the rooms had a ton of people in them and conversations were running like water from a faucet. So I decided to sit back and just read what others were writing. A lot of it got me hot and started to turn me on so I figured that I'd give it a try and talk to someone. Like I said, I've never tried this or anything close to it before (with another man).

I started talking to this older gentleman. He was really nice and didn't seem like one of these people who just wanted to meet me and fuck me. He wanted to get to know me and reassure me that I didn't have to rush into anything (if I chose to do something) and I could relax. We hit it off and he asked if we could chat through IM rather than the board. I figured he was really nice to me so why not? He started to tell me about his fantasies. Mostly he wanted to try bare backing cause he had never tried it. He also told me about a couple of his experiences (which wasn't many). That was another good sign for me because I would be worried about catching something. Sounds silly I know but for someone new at this, these are the things going through my head.

Finally he asked me my age and if I had any fantasies. Out of curiosity I had looked online at Bi-Sexual and Gay pics and videos so I had an idea of what it would be like. There was one fantasy that stuck in my head vividly so I explained it to him...

"I'm by myself in a hotel/motel room. I get undressed to go take a shower because I know someone is meeting me there in a short amount of time and I wanted to be clean for him. While in the shower I soap up my body and begin to massage my cock. The dirty thoughts in my head of what I was going to do started to turn me one and my cock started to grow and get harder and harder. Once I was fully clean I begin to stroke my cock with one hand and massage my asshole with the other. Knowing that fucking may be on tonight's menu and soaped up my fingers and began to insert one finger at a time into my ass. Thinking about the upcoming task was making me so hot and the fingers up my ass made me stroke faster and faster. Finally I came back to grips and got out of the shower. I put the towel around my waste and lay down on the bed. I had a blindfold and I put it on. The person I was meeting arrived and closed the door behind him. I could hear him walk across the room and into the bathroom. I heard the shower start and the curtain close. I knew he was getting ready for me. In a few minutes the shower stopped and I heard the curtain again. He got out and walked over to the bed and climbed on top of it.

I felt a tug on my towel and soon enough I was laying there naked with my raging hard-on pointing right at him. He opened my legs wide and I could feel his breath on the head of my cock. I could feel his tongue teasing the head, then licking down the shaft and drawing circles around my balls. In one swoop he took my entire 6.5" cock in his mouth and furiously went up and down on it. I have never been so hard. He used one hand just below his mouth to aid in the stroking motion and the other hand to massage my full balls. After about 10 minutes he takes his mouth off of my cock and slides up to my nipples. He gives them a little lick and a nibble. Finally his mouth meets mine and we engage in a deep kiss. Our tongues battled wildly. I can feel his hard cock grinding on mine. He broke our kiss and positioned me so that I was slightly sitting up. He straddles me on his knees and walked up close enough so that his hard cock barely touched my lips. I could taste his precum. I open my mouth and he began to fuck my face ferociously. Both my hands are squeezing his ample ass cheeks and forcing him back and forth into me. I can feel his balls slapping my chin from the hard fucking motion.

He's grunting and groaning and he says that he wants to fuck me. He takes his cock out of my mouth and again he repositions me onto my back. He kneels between my legs and slowly eases himself down on top of me. I can feel his hand guiding his hard cock towards my virgin ass. Once he gets there he slowly pushes his soft head in. It hurts for the moment but once his head passes through the pain starts to disappear. He slowly pushes all of his manhood deep into my ass. I can feel my ass squeeze around his thick shaft. He begins to slowly slide his cock in and out of me. I can feel the sensations I've never felt before. I wrap my legs around his ass pulling him into me, forcing him as deep as he can go. After I did this he must have felt completely turned on because he wildly kissed me again. His speed began to pick up as he was fucking me. Besides the sound of our kissing you could hear his flesh smacking against mine. His cock felt so good inside me and his balls hitting my ass was an added bonus. Finally breaking our kiss, he said he was going to cum and that he wanted to cum inside me. With my approval he fucked faster and faster until I felt stream after stream of his warm cum spill into my ass".

After I finished telling him my fantasy he told me that he had been stroking his cock and that he came all over himself. I felt pretty flattered. He told me that he had to go but that he wanted to chat with me again the next day. So I agreed and we signed off.

The following day we chatted for what seemed to be all day long. We teased each other and told each other what we would do to each other if we were to ever meet. He even used pieces of my fantasy to tease me. We did this for almost a week straight (getting to know each other and tease each other). I also had found out some interesting facts. First that he was married and had children and secondly that he was a teacher at the college I was going to.

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The next day I must had been really horny because when he came online to chat I told him that I wanted to meet him that day in his school office so we could fool around and possibly fuck. We had never seen each other so this was going to be difficult so he told me where his office was on the campus and what he was wearing so I'd know it was him. I had packed a gym bag earlier in the morning with a blanket, baby oil, towels and condoms figuring that if he agreed to meet that I would be ready for anything. So later that evening I went to the school and walked into the building where his office was. I was really nervous, with this being my first time trying anything like this. I went up the stairs and when I got to the top there was a lobby in front of me and there he was, sitting on a chair talking with another faculty member. He looked up and saw me and called me over. He was around 6'2", 220 lbs, salt & pepper hair, green eyes and had a mustache. It looked like he had finished talking. When I got close he said out loud but not too loud, "Let's go into my office and talk about that paper". Once we got to his office he opened the door and let me in the closed and locked the door behind us.

Butterflies were in my stomach but he broke the ice and said Hi to me first and began chatting with me about how intense I seemed online that day and that he was surprised. Then he asked me to undo my pants. I un-tucked my shirt and undid my pants and pulled them along with my underwear down to the floor. He motion for me to come closer. I walked over to him and he reached out and grabbed my cock. I have never had another man's hand on my cock before and it felt good. We propped me up on top of his desk and he removed my shoes, socks, pants and underwear. I was completely nude from the waste down. My cock was starting to stir and he could tell. He went right for it and put it right into his mouth. As soon as the moistness of his tongue and mouth touched my cock I became instantly hard. I could tell he loved it cause he was tenting in his own pants and increasing the speed of his mouth over my cock. The sensations were so good that I had to lie back on the desk and grab his head with both hands and face fuck him. This went on for a few minutes 'til I stopped him and sat him in his chair. Once in his chair I climbed off the desk and undid his pants and pulled out his cock and full balls. I wrapped my hand around his 7.5" thick cock. Before I even gave it a stroke he said he was going to cum. I guess the anticipation was enough to get him off. I began to stroke him and sure enough he came all over my hand. I reached in my bag and grabbed the towel and wiped my hand.

I turned back to him then straddled him in his chair. I sat right in his lap (feeling his softening cock under my ass) and began to passionately kiss him. Our tongues met and it was electric. I could feel him getting hard again. That brought a smile to me face. So I got off of him and had him stand up in front of me. I pulled his pants down to reveal a thong that he was wearing. He had told me that he wore it just for me. I pulled that down and turned him around. His cock was now rock hard again and staring me in the face. Building up the nerve I stuck my tongue out and began to flick it. I tasted the remnants of cum on it and it tasted good. I teased his head and began to tongue his shaft. Kiss his shaft and eventually lick his swelling balls. Knowing that he was really wanting it, I put his cock into my mouth. I just did what felt natural and I began to slide back and forth on it and I could feel every vein with my lips and tongue. I massaged his balls with one hand and stroked my cock with the other. He was getting weak in the knees so I pulled his cock out of my mouth and turned him around and bent him over his own desk. I took my hard cock and placed it in between his ass cheeks and began to grind into him. I could hear him moaning under me. I squeezed his cheeks together with me hands and I fucked in and out of his cheeks. I let my cock slide out and slip underneath his balls touching his own cock. He reached down and began to stroke both our cocks at the same time. What a feeling this was. Just as it was getting to the point where we both wanted more, we heard someone trying to open the door. So we raced to put our clothes on as fast as we could and decided to try it another time.

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