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Me and Jack

Category: Gay Male
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I had been to the bookstore many times and had a lot of fun going there. I knew I would continue to go there but since I had moved to Jackson it was less frequent. I also knew that I was wanting a little bit more out of this side of my life. I wanted to try to meet someone to hook up with occasionally. I wasn’t quite sure how to do this, but I knew if there was a way, it would have to be on the Internet. I started searching the Internet and looking for ways to meet men.

I found a couple of dating sites specifically geared towards gays and or alternative lifestyles. I created my free accounts and started browsing through the listings. After a few weeks I still had no interested people. That’s when I stumbled upon Yahoo chat.

I’d heard of Yahoo chat of course, but had never tried it. I found a reference to a Yahoo chat room for gay men. I decided to try it and downloaded Yahoo chat. After installing it and choosing a screen name I immediately logged into the gay chat room. I chatted in the general gay chat room for little while with no luck. Then I realized that you could create your own room. I found a listing of private rooms and started looking. I found a room entitled ” Mississppi gay men”. I entered, and realized there were several hundred people chatting in this room. Jackpot!

I sat back and watched the chat progress for a period of time before I tried typing anything in the room. I was still very nervous even though I knew no one knew who I was. I started out by saying hello to everyone. I had never been in chat before and I wasn’t sure what I should say. As I watched the chat scroll by I noticed that some people would just type in a city name. I realized that this was to see if there was anyone in the room from that area. I decided to go ahead and type Jackson.

At first no one answered. I waited about 10 minutes, typed Jackson again, and waited again. After about the third time with no one answering I was getting frustrated. I decided to just let the chat program run and listen in on the conversations. I did this for several days before I felt comfortable enough to join the actual chat. But once I did join the chat I realized that most of the people in the room were very nice. They all accepted me as a member of the room and included me in all the conversations. I was really beginning to enjoy myself.

After several weeks I realized that I could fill out a profile and even attach pictured if I wanted to. I filled out the personal profile but did not feel comfortable posting a picture. I started to browse through the profiles of everyone in the room. I found several people whose profile sparked my interest. I decided to try to chat them up. The first couple I tried to chat with never responded when I sent my IM. But eventually I did get a response from one person. We chatted for about 20 minutes and added each other to our buddy list.

After a few weeks of running into my friend in the chat room on a daily basis I decided to be bold and ask him if he ever met someone from the chat room. He said that he had never done that but had wanted to on a couple of occasions. I knew from reading his profile that he was pretty much a top and that fit in with what I was looking for. I decided to be even bolder and asked him straight up if he would consider meeting me. He said he thought he would but we lived so far apart. He knew I lived in the Jackson area and he told me that he lived near Oxford. It was a couple hour drive between the two.

I told not to worry about the distance because I often traveled to the northern part of the state. When I traveled up their I would usually stay overnight in a hotel. If he really wanted to meet with me the next time I went up north I would make sure I got a hotel room near his town. He agreed and asked when the next time I would be up in his area would be. I told him I could make the arrangements for a trip in as little as a week or for whenever he was available.

We decided that I would get a hotel room in Batesville in two weeks. I immediately booked a room and let him know what hotel I would be at. He recognized the hotel and he told me that we could meet at the Burger King which was right next door. That way we would be meeting in a public place and if either one of us felt uncomfortable we could call it off at that point. I agreed with that plan and was really excited about meeting him.

Over the next two weeks we chatted almost daily and always ended our chat talking about how much we could not wait to get together. I was constantly in the state of arousal just thinking about having a man in a hotel room all to myself. I spent those two weeks getting what I felt I needed to take with me. I purchased an enema bag, a box of condoms and a bottle of lube.

On the day we were supposed to meet I left early and drove to Batesville. I arrived in Batesville at about 12:30 PM. I got a quick lunch and checked into the hotel at 1:15 PM. As soon as I got to the room I went into the bathroom and started to prepare. I gave myself a very thorough enema and took a shower. Jack was set to arrive at about 3:30 PM. By 2:30 PM I was sitting on the hotel bed in my shorts and a tee shirt watching TV. It seemed that every 5 minutes I would look at the clock and thought time was moving awfully slow.

At 3:25 PM I left my room and walked downstairs. I left the building and crossed the parking lot towards the Burger King. When I walked in there was only one person at a table. It was a rather nice looking man about my age. I looked at him and he gave a small smile. I walked over and asked if his name was Jack and he said you must be Ken. I told him that yes my name was Ken and it was nice to finally meet him face to face. I sat down opposite him at the table. We talked for a couple of minutes and he finally asked if we were going to go up to my room. I said sure so we got up and walked out the door. He followed me across the parking lot and into the hotel. As we crossed through the lobby it felt like everyone in the hotel was watching us. I was nervous and excited both at the same time again.

When we got to the room he followed me in. As soon as the door closed Jack reached over placed his hand behind my neck and pulled me close for a kiss. I had never even thought about kissing a man. He really didn’t give me a choice and before I even realized it his tongue was in my mouth and mine was in his. I could not believe that I was standing in a hotel room kissing a man. I was shocked but not repulsed. I could feel the stubble on his face rubbing against mine. It was different than kissing my wife and I can honestly say it was very erotic too. I was enjoying it and it was also turning me on greatly.

We broke the kiss and he apologized for being so forward. I told him that was OK because I was so nervous and sort of liked the fact that he was taking charge. He said OK and then preceded to tell me to get undressed. As I pulled my shirt off over my head I saw him doing the same thing across the room. By the time I was down to just underwear he was already completely nude watching me finish getting undressed. I was nervous but my cock was already as hard as rock. As I pulled my underwear down he gave a quiet wolf whistle. I know I must’ve blushed as red as a valentine heart.

Once I was naked he told me to get on the bed. I did as he told me and he climbed on next to me. He leaned in and kissed me once more and as he did that he reached down and took hold of my cock. I moaned into his mouth I reached down and took his in my hand as well. We laid on the bed kissing and stroking each other’s cocks for several minutes. The longer we kissed the more bold I became. I was stroking his cock one hand and running my other hand up and down his chest.

We broke the kiss off and he immediately repositioned himself so his cock was at my head level. I didn’t need to be told what he wanted. After all it was what I wanted to. I reached out and took his cock in my hand and pointed it towards my face. I leaned down and stuck out my tongue and ran it across the head of his cock. As I did this he moaned. I could taste the slight saltyness of his precum. I licked up and down his cock allowing my saliva to make it nice and wet and slippery. After a few minutes of this I raised my head over his cock and in one swift motion took his entire cock into my mouth. When his cock it the back of my throat I just kept going. I allowed his cock head to enter my throat so that I could take the entire thing in my mouth. He moaned loudly and put his hand on the back of my head. He applied a slight pressure forcing me to keep his cock lodged in my throat.

After a few seconds he released his grip on the back of my head and I happily started to bob up and down on his cock. I had almost forgotten what I was really there for and was trying in earnest to get him to shoot his load in my mouth. I would raise my head completely off his cock and then engulfed his entire cock in one stroke allowing his head to plunge deep into my throat. It felt great to finally be sucking a cock without a wall in between me and the owner. I was finally free to suck as hard and deep as I felt I wanted to.

As I was sucking Jacks cock I was caressing his balls with one hand.He had lightly hairy balls. I prefer shaved but his were nice size and not real hairy. I released his cock from my mouth and lowered my head to his balls. I licked his balls and let my spit cover them. As I licked Jacks balls, I was still stroking his cock with on hand. My other hand was slowly stroking my own cock. I was close to cumming all over my hand but I did not want to cum yet. I released my own cock from my grip and tried to will myself to calm down.

I licked back up the shaft of Jack’s cock and slowly used my tongue to swirl around head of his cock. As I continued to stroke his cock in my hand I leaned back and looked at it. His cock was gorgeous. His cock was about 7 1/2 to 8 inches long and my fingers didn’t quite touch when I put my hand around it. The head was slightly larger than the shaft and it was a deep red color. Again I leaned in close and this time I started by licking the tip of his cock and slowly circling my tongue around the head. As my tongue circled around the head I lowered my head taking his cock into my mouth at as slow a pace as I could go.

As I slowly engulfed Jacks cock in my mouth, he was moaning the entire time. It felt so good to have a cock sliding through my lips into my hot wet mouth. I couldn’t remember a time when I had ever been this turned on. I really enjoyed sucking jacks cock but what I really wanted was to feel it sliding in and out of my ass. I bobbed my head up and down for a few more minutes and then decided to take charge. I released his cock from my mouth, looked him in the eyes, and told him it was time for him to fuck my ass.

Jack looked down and smiled, gave a small chuckle, and said he couldn’t wait to feel my tight ass wrapped around his cock. I got out of the bed and walked over to my duffel bag and pulled out a box of condoms and a bottle of lube. I tossed the condoms to jack and he laughed and said ‘how many times do you plan for me to fuck you?’I laughed back and said as many times as you can.

I watched as jack opened the box of condoms pulled one out and opened it. He placed the condom on head of his cock and rolled down the shaft. The entire time he was watching me and I could almost feel my cock get harder. I climbed back onto the bed and handed him the bottle of lube. He asked me what position I preferred. I told him the only time I had been fucked I was standing up bent over with a man behind me. I told him that whenever position he wanted was fine with me.

Jack told me to get on my hands and knees on the bed. As I moved to get on my hands and knees I watched him pour lube over his condom covered cock. I felt the bed shift as he moved behind me and then I felt the cold liquid being poured across my ass. Jack used a finger to rub lube into my ass. I felt him insert a finger and I moaned. He moved the finger around and in and out several times before he pulled it out. It was only a second later that he shoved two fingers in my ass. It felt good to have his fingers in my ass and I knew he could tell I was excited.

He asked me if I was ready and I moaned yes. Jack removed his fingers from my ass and I felt the bed shift again as he moved closer. I felt his cock rub against my ass hole and I instinctively pushed back. He moved his cock as if he was teasing me. He could tell I wanted his cock in my ass but he wasn’t ready to do that yet. He continued to tease me by rubbing his cock up and down the crack of my ass. Every couple swipes he would rub the head of his cock against my hole. I was going out of my mind. All I could think about was having that cock in my ass.

Jack told me to tell them what I wanted. I looked over my shoulder and look square in his eyes and told him to put his cock in my ass and fuck me. Jack needed no further encouragement. I felt the head of his cock on my ass again and this time he didn’t move when I pushed back. I felt the head of his cock opening my ass. Jack didn’t move, but let me push back driving is cock further into my ass. I didn’t stop pushing until I felt my ass bottom out on his cock. Never had I been this full. I could feel the head of his cock deeper in my ass than any other cock had ever been.

When Jacks cock was fully in me he reached down and grabbed my hips and kept me from moving. He stayed still allowing his cock to be fully in me without moving for several minutes. He was moaning telling me how hot and tight my ass was. I looked back at jack and his head was tilted back and his eyes were closed in extasy. I too was in extasy.

After couple of minutes jack started to move slowly in and out of my ass. He started with short strokes just moving an inch or two. It felt so good to finally have a cock in my ass without a wall between me and it’s owner. Jack was free to pound me as hard as he wanted with no obstructions to get in the way. Jacks cock was rubbing up against my prostate and my cock was leaking a constant supply of precum. Jacks strokes began to get longer and after about 10 minutes he was almost pulling the entire cock out before plunging all the way back in. Being fucked never felt this good before.

As jack pounded his cock in my ass I was moaning and begging him to fuck me longer and harder. Jack began pulling his cock all the way out and plunging in all the way back in in one stroke over and over. Each time he pulled out my ass made a popping noise and each time he plunged back in my excitement grew and grew. I begged him to keep fucking me as hard as he could. Jack started pounding me harder and harder. The room was filled with the sound of jack pounding me our skin smacking against each other and both of us moaning.

Jack continued pounding me for about 15 minutes before he told me he was going to cum. I told him I wanted him to come on my face. Jack pulled out and as he removed the condom I turned as fast as possible and lay on my back. Jack leaned over me and stroked his cock and within seconds his cum was shooting all over my face and in my mouth. As jack shot his load all over my face I was stroking my own cock and before he was finished cumming I was shooting my load all over my chest. I couldn’t believe how much cum he shot all over me. It was hot and wet and I could feel it running all over my face through my hair and down my neck.

Jacks cum was all over my face and in my mouth and tasted wonderful. I couldn’t wait for the next time he could shoot so that I could take it directly in my mouth. When jack was finished cumming he used the end of his cock to rub his cum all over my face. He pressed the end of his cock on my lips and I immediately opened my mouth. He pushed his cock past my lips into my mouth and I could taste his cum all over the head of his cock. I used my tongue to clean his cock and swallowed as much of his cum as I could. I couldn’t get enough.

After a minute or two of me sucking his cock he pulled his cock from my mouth and collapsed next to me. I continued to rub my cum and his cum into my skin. I could never remember cumming this much and it felt so good to have a huge amount of cum all over me. We were both exhausted and breathing heavy and I thought we were going to both pass out. After a few minutes of laying there relaxing, and still rubbing cumming to my skin, Jack sat up and said that he had to leave soon. I told him I understood and thanked him for the wonderful fuck. Jack said he looked forward to doing it again sometime soon.

As jack and I got dressed I kept staring at his crotch. I couldn’t believe that I had just sucked and been fucked by this man. Jack noticed me staring and smiled as he chuckled. When we were both fully dressed we walked towards the door. At the door jack turned around kissed me and pushed me to my knees. I did not resist.

Jack opened his zipper and pulled out his semi hard cock. I immediately engulfed his cock in my mouth and started bobbing up and down on it. I had only been sucking for about 2 minutes when he pulled his cock out of my mouth shoved it back in his pants opened the door and as he walked out said ‘you can finish that next time we meet’. As the door closed I immediately began to plan for my next trip.

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