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Anything Goes
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Straight Male / 50
My confession is this. My wife is not aware of how many times I have masturbated with other guys.
My first time was with 3 of the neighbor boys when I was just about 12 years old. We had a game called chicken where one guy would do something and the others had to follow suit or chicken out. This one time one of the guys started undressing. We all followed suit and soon we were all naked and looking at one another’s boners. While we were naked we got to talking about sex and how we liked to rub ourselves and how great it felt. We did this about two or three times a week since my parents weren’t home during the day. One day later that summer I was alone and naked in my room and was humping my cock on my mattress which was my favorite way of getting the feelings me and guys had talked about. I kept going and then the feelings got amazing and the next thing I knew I was squirting white stuff out of my cock! I thought I had broken something but found I couldn’t stop doing it since it felt so good.
I told my buddies and they didn’t believe me. So I told them to follow me home and we played a some more chicken. Now we are all naked and they are sitting on the bed staring at my cock as I humped the side of the mattress. I told them her it comes, and shot out a huge couple of spurts as they sat amazed. That was cool they said. Now it was my turn to watch them doing the same thing. I was older than them by about a year and I guess they weren’t of the age where they shot cum.
My second time I jacked off with a guy was a few years later. I was about 15 I think. A friend of my brother who was a couple years younger than me, came home with me after going swimming. When went into the house and he saw a plate of cookies on the counter and asked if he could have one. I was horny at time and told him he could if he came into my room stripped naked and then he had to walk out into my kitchen and get the cookie. He laughed and said OK! He took everything off and walked out there and grabbed a cookie. He came back into my bedroom and stood there smiling, naked with a little boner sticking out. I undressed too now and while he sat there eating the cookie he was staring at my growing cock. He said, wow yours is big! I said thanks. I started talking to him about jacking off and he hadn’t heard about it. I told him I would show him but first he had to do something for me. He said what? I don’t know why I said it but I told him he had to put his mouth around my cock for a little bit. He smiled and said, only if you do it too! I said OK. He got down on his knees in front of me and put his mouth around my cock. He couldn’t get it all in but he tried. It felt amazing. He then stood up and said it was my turn. I got down in front of him and for the first time in my life I put a penis in my mouth. I was surprised how hard and smooth it felt. I went up and down on it for little while like he had on mine and then stood up. I asked him if he would like to watch me cum. He wasn’t sure what I meant but I had him sit on my bed and then I started humping my mattress while he watched. He was shocked when he saw me shooting several spurts of cum.
My third time was with my nephew later that summer. He actually brought up the subject about jacking off together. We went into my house a few days later and undressed in my room. He was almost my age and our cocks were about the same size too. We ended up doing oral on each other for while. Longer than my first time that is for sure. We ended up with one of us humping the others ass crack until we came, then changed places, he rubbed on me and I felt his hot cum on my ass crack.
My fourth time was many years later when I was in my late 20’s. I was working as a security guard at construction site of new homes. I was working 5 to 10 pm. It was a dull job that had me sitting in my car listening to radio or reading. One evening about 7 or so a guy in pick up drove up and asked if he could look at some of the homes. I said sure and he headed off. About 15 minutes later he drives back and parks next to my car just a little to front of me. He started asking me questions about things in general and we chatted freely for awhile. He somehow got the subject on sex and porn movies and jacking off. We shared out personally experiences and really got into what we liked sexually. As we were talking I could see that his right arm was going up and down in a steady motion. I knew he was as horny as I was then. It was about 80 degrees that evening and I had my shirt unbuttoned down to the last two buttons before he even showed up. So I slowly undid them and then discretely undid my belt and zipper and slid my uniform pants down. I wasn’t wearing underwear so they came off easily. So here I am now basically nude stroking my cock while talking about sex with a guy in a truck next to me. He decided he needed to get out of car while we talking and that’s when I noticed he had his right hand down inside his pants and stroking away. I told him as he walked up that he should just pull it out, it would be more comfortable that way. He smiled but didn’t do it. I told him, hey I have mine out! That is when he walked closer and looked in. From where he stood you could see my naked body from head to ankles. I was stroking away too. He said, oh and you’ve got a big one too! (just shy of 7 and thick) That is when he finally turned sideways by my window and pulled his cock out. It had to be about 5 inches or so. He gave it a few more strokes and dribbled out about 4 spurts of cum. I leaned my seat back while he watched and I shot about 5 spurts onto my chest. He left right after that.
My fifth time was in the showers at the YMCA. The guy across from me was staring at me while I was showering. It got me a little heated up and my cock got to about a semi. I rubbed it with soap to see what he would do. He turned away and then about 30 seconds later he turned facing me with a huge cock that he was stroking. I followed his lead and now were both stroking for each other until we came.
My sixth time was also at the Y. I went into the steam room to relax for a while. I was in there alone and was rubbing myself just so if anyone came in I would larger than when I am really soft. An old skinny guy came in and sat next to me. He sat there for a few seconds and leaned right over in front of me and just stared at my limp cock. I told him if you want to look at it, here! I pulled it from between my legs so it sat on my pubes. That is when he reached over and started stroking me. I grabbed his very small cock 4 ½ by the look and started stroking him. I don’t think I lasted 30 seconds and I shot a load all over my legs. I freaked out and left the steam room after that.
My last time was in the same steam room at the Y. I saw the same guy who was stroking along with me in the showers before. He finished his shower and walked away towards the locker room. I decided to get in the steam room again and who should be in there but the shower guy. I said hi and sat down near him. He reached over immediately and started stroking me. I looked down at his cock and saw that it was already hard so I grabbed his and started stroking along with the rhythm he was doing on mine. The steam in the room was getting thin and the room has a glass door so I told him to hang on while I gave us more steam for privacy. I hit the button and rooms started to fill up with steam again. As I walked back to sit down the guy grabbed my cock and then pulled it into his mouth. He knew what he was doing I can tell you that! I came almost immediately and shot at least 5 or 6 huge spurts into his mouth with he swallowed. He got up and left the room immediately. I hit the showers shortly after that.
Those are my secret confessions.
My first time was with 3 of the neighbor boys when I was just about 12 years old. We had a game called chicken where one guy would do something and the others had to follow suit or chicken out. This one time one of the guys started undressing. We all followed suit and soon we were all naked and looking at one another’s boners. While we were naked we got to talking about sex and how we liked to rub ourselves and how great it felt. We did this about two or three times a week since my parents weren’t home during the day. One day later that summer I was alone and naked in my room and was humping my cock on my mattress which was my favorite way of getting the feelings me and guys had talked about. I kept going and then the feelings got amazing and the next thing I knew I was squirting white stuff out of my cock! I thought I had broken something but found I couldn’t stop doing it since it felt so good.
I told my buddies and they didn’t believe me. So I told them to follow me home and we played a some more chicken. Now we are all naked and they are sitting on the bed staring at my cock as I humped the side of the mattress. I told them her it comes, and shot out a huge couple of spurts as they sat amazed. That was cool they said. Now it was my turn to watch them doing the same thing. I was older than them by about a year and I guess they weren’t of the age where they shot cum.
My second time I jacked off with a guy was a few years later. I was about 15 I think. A friend of my brother who was a couple years younger than me, came home with me after going swimming. When went into the house and he saw a plate of cookies on the counter and asked if he could have one. I was horny at time and told him he could if he came into my room stripped naked and then he had to walk out into my kitchen and get the cookie. He laughed and said OK! He took everything off and walked out there and grabbed a cookie. He came back into my bedroom and stood there smiling, naked with a little boner sticking out. I undressed too now and while he sat there eating the cookie he was staring at my growing cock. He said, wow yours is big! I said thanks. I started talking to him about jacking off and he hadn’t heard about it. I told him I would show him but first he had to do something for me. He said what? I don’t know why I said it but I told him he had to put his mouth around my cock for a little bit. He smiled and said, only if you do it too! I said OK. He got down on his knees in front of me and put his mouth around my cock. He couldn’t get it all in but he tried. It felt amazing. He then stood up and said it was my turn. I got down in front of him and for the first time in my life I put a penis in my mouth. I was surprised how hard and smooth it felt. I went up and down on it for little while like he had on mine and then stood up. I asked him if he would like to watch me cum. He wasn’t sure what I meant but I had him sit on my bed and then I started humping my mattress while he watched. He was shocked when he saw me shooting several spurts of cum.
My third time was with my nephew later that summer. He actually brought up the subject about jacking off together. We went into my house a few days later and undressed in my room. He was almost my age and our cocks were about the same size too. We ended up doing oral on each other for while. Longer than my first time that is for sure. We ended up with one of us humping the others ass crack until we came, then changed places, he rubbed on me and I felt his hot cum on my ass crack.
My fourth time was many years later when I was in my late 20’s. I was working as a security guard at construction site of new homes. I was working 5 to 10 pm. It was a dull job that had me sitting in my car listening to radio or reading. One evening about 7 or so a guy in pick up drove up and asked if he could look at some of the homes. I said sure and he headed off. About 15 minutes later he drives back and parks next to my car just a little to front of me. He started asking me questions about things in general and we chatted freely for awhile. He somehow got the subject on sex and porn movies and jacking off. We shared out personally experiences and really got into what we liked sexually. As we were talking I could see that his right arm was going up and down in a steady motion. I knew he was as horny as I was then. It was about 80 degrees that evening and I had my shirt unbuttoned down to the last two buttons before he even showed up. So I slowly undid them and then discretely undid my belt and zipper and slid my uniform pants down. I wasn’t wearing underwear so they came off easily. So here I am now basically nude stroking my cock while talking about sex with a guy in a truck next to me. He decided he needed to get out of car while we talking and that’s when I noticed he had his right hand down inside his pants and stroking away. I told him as he walked up that he should just pull it out, it would be more comfortable that way. He smiled but didn’t do it. I told him, hey I have mine out! That is when he walked closer and looked in. From where he stood you could see my naked body from head to ankles. I was stroking away too. He said, oh and you’ve got a big one too! (just shy of 7 and thick) That is when he finally turned sideways by my window and pulled his cock out. It had to be about 5 inches or so. He gave it a few more strokes and dribbled out about 4 spurts of cum. I leaned my seat back while he watched and I shot about 5 spurts onto my chest. He left right after that.
My fifth time was in the showers at the YMCA. The guy across from me was staring at me while I was showering. It got me a little heated up and my cock got to about a semi. I rubbed it with soap to see what he would do. He turned away and then about 30 seconds later he turned facing me with a huge cock that he was stroking. I followed his lead and now were both stroking for each other until we came.
My sixth time was also at the Y. I went into the steam room to relax for a while. I was in there alone and was rubbing myself just so if anyone came in I would larger than when I am really soft. An old skinny guy came in and sat next to me. He sat there for a few seconds and leaned right over in front of me and just stared at my limp cock. I told him if you want to look at it, here! I pulled it from between my legs so it sat on my pubes. That is when he reached over and started stroking me. I grabbed his very small cock 4 ½ by the look and started stroking him. I don’t think I lasted 30 seconds and I shot a load all over my legs. I freaked out and left the steam room after that.
My last time was in the same steam room at the Y. I saw the same guy who was stroking along with me in the showers before. He finished his shower and walked away towards the locker room. I decided to get in the steam room again and who should be in there but the shower guy. I said hi and sat down near him. He reached over immediately and started stroking me. I looked down at his cock and saw that it was already hard so I grabbed his and started stroking along with the rhythm he was doing on mine. The steam in the room was getting thin and the room has a glass door so I told him to hang on while I gave us more steam for privacy. I hit the button and rooms started to fill up with steam again. As I walked back to sit down the guy grabbed my cock and then pulled it into his mouth. He knew what he was doing I can tell you that! I came almost immediately and shot at least 5 or 6 huge spurts into his mouth with he swallowed. He got up and left the room immediately. I hit the showers shortly after that.
Those are my secret confessions.
