Do you remember the days of AOL chat rooms? Well those of you who remember I bet there were some great conversations and hook ups after those chats.
That is where this story begins a M4M chat room. There was lots of general chat going on in the room when I got an IM simply saying. What's Up?? That was no different than the same message coming many times in the past and one that I used to try and start a conversation. Not much here how about you? It simply said it has been a long day and now I am ready to try and relax. My response was very similar something like, yea me too.
Him what did you do today Me was out chasing tuna for five or six hours and only saw a few whales and no tuna. It was a little rough so I feel beat up. Him how far out were you and what kind of boat Me about 30 miles in a Grady Him I know what it can be like out there Me really??
Him yea I have a 47 foot sail boat that I take every winter to North Carolina ( he is from Maine) Me I guess you really know what it can be like out there. I am aching all over this was my subtle way to explore any interest from him. Him wouldn't it be great to have someone just give you a massage Me you can say that again. Him I am in southern maine, where are you? Me (now I am thinking this could be the opening) about 15 minutes from the state line.
Him can you tell me a little about you G and X stuff if you want Me well I am early 50's 5'9" 171 lbs, 6.5 cut and thick Him VERY NICE Me your turn Him 5'11" 165 lbs 6, cut and average plus a little older than you Pause where neither of us typed anything for a minute or so Him so… would like a massage? Me it is kind of late and I still have not showered from the fishing trip. Him that is OK my wife is out of town so you could take your shower here then I can give you a massage.
Me I hesitated a little then agreed to go to his house my wife was also out of town visiting her mom on RI. I arrived at his house and it must have been 4500 square feet right on the ocean (I found out later he is a doctor and has had this home for over 25 years) He showed me around the first floor and out on his deck overlooking the water.
At this point he offered me a drink so I accepted and asked for a diet of some kind. He brought it out there and we had some idle chat as we drank our sodas. He then finally said, are you ready to take your shower.
Now that we have chatted live for over 30 minutes I was feeling comfortable and looking forward to the massage. As we entered the kitchen from the deck I noticed a gay porn video playing on a TV over the fireplace. I stopped and was watching when he came over and stood along side of me and said like it?
I nodded in approval, he took my empty can then came back and stood near me again. As we were watching a hot guy give his buddy a blow job he, ever so gently started to rub my back.
I felt myself begin to totally relax then his hand slid down and began rubbing my butt. I let my butt "fall into" his hand.
He said ready to take your shower? I said Yep! He lead me upstairs and showed me around beginning with the spare bedrooms, extra bathrooms then his bedroom (which had a different gay porn video playing) and then into his bathroom. He turned the shower on and said lets go.
I got undressed and got into the hot shower, boy did it feel good. I was just standing under the shower with my eyes closed enjoying it when I felt him behind me. He began rubbing my back, adding soap and working down to my butt. As he was washing my but he slid his fingers between my cheeks then gently began to slide his finger inside me. Believe me when I tell you it felt great!! He got close to me, wrapped his arms around me to wash my chest, stomach and yes my rock hard cock.
His hands were all over my chest, nipples and cock when I felt him reposition himself and he slid his cock into my butt, whew. He pumped me a few times then pulled out. We finished the shower, dried off then headed to his bedroom. We climbed onto his bed and he began at my feet with the massage he promised me. I had positioned myself so I could see the TV and the gay porn video.
I was on my stomach and he worked up my legs to my butt and again his fingers were in and out of my hot and waiting butt. He finished my back then rolled me over to see my rock hard cock which he ignored. Instead he began to play with my nipples and then began to suck and gently bite them, this was so hot.
He worked his tongue down my chest to by belly button where he spent several minutes sucking and poking it with his tongue. Finally the moment of truth he started to play with my cock, first with his fingers then he started to lick the head and slit. In one quick and unexpected movement he took my whole cock in his mouth and just held it there without moving. I looked to the left and his cock was within reach so I started to massage it.
I wanted to suck it now so I tugged on the inside of his leg and he knew exactly what I wanted.
He moved over and we were in the perfect 69 position and both sucking on each others hot cocks. I put my hands on his butt and was squeezing it as he pumped his cock in and out of my mouth. He rolled off me, reached to the bedside table and pulled out a condom which he slid on his cock. He rolled me to my side, cuddled behind me and gently slid into my waiting butt.
He then pulled out and some how I ended up on my hands and knees where he began to pump me doggie style, slowly at first then the pace picked up.
He pulled out and did not think he came, well he didn't. He had me get on the edge of the bed on my back where he put my legs on his shoulders so he could enter me again. This time as he pumped me he was jerking me off I could not hold off any more and shot a load all over my stomach. He continued to pump me then his pace quickened he pulled out and ripped off the condom and jerked a load on my chest.
We were both out of breathe and began to use our cum to finish my massage. He asked me if I wanted to clean up and take another shower. I did but this time he did not join me instead he had a couple of drinks waiting in his bedroom. We sat on a small couch watching the gay porn. It was silent for a while then he placed his hand on my thigh and asked me if I enjoyed myself. I bet you can guess the answer I said why yes We watched a little more of the movie when he asked me if I wanted to spend the night.
I looked at the time, nearly 10PM, and I said let me give my wife a call. I went downstairs and out on the deck naked (it was very private and no one could see me). I spoke with her and she told me her mom was doing good and that she would be home tomorrow night.
He was in the kitchen still naked watching the same video when I told him that I would spend the night. I asked which room would be mine for the night hoping he would say I would sleep with him.
His answer was like I hoped his bed with him. Everything was shut off when we climbed into bed. He cuddled near me and reached down and grabbed onto my cock. He was simply holding it as we fell asleep. At some point during the night I woke up to him rubbing my cock.
I did not move as if I was still asleep and he stopped. I felt him move but I stayed still until I felt him getting close again and I shifted to "get comfortable" but really was moving my butt in position for him. I guessed right, he slid into me and began to pound me again so I "woke up" reached around and put my hand on him.
This time he kept pumping until he came inside me and my hope was that he had on a condom and he did. Morning came, we got up and went to the kitchen where we had coffee and talked about how great last night was. There was one more thing I needed to do and that was to thank him.
He was putting the coffee cups in the dishwasher as I walked over to him, stood behind him and wrapped my arms around him. After just holding him for 20 seconds or so I slid one hand down to grab his cock which now was semi-hard.
I turned him around and got on my knees and gave him a great blow job. When I started to feel him cumming I stopped sucking and jerked him off so he could shoot on my face.
This all happened about 8 years ago and we still meet in either his office or on his sail boat for some great sex every month or so. We have not been able to spend another night together as our wives have not been out of town on the same night again.