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First time & lots of fun

Posted by: Author: Age: 40 Posted on: 3 comments
3 likes 1218 views Category: Masturbation Male-Male Tags: in his mouth

I never thought I would be sharing this with anyone in the world but it feels OK to do it here.


I was a bit old for jacking with buds at 18 but on this weekend it happened & it felt perfectly fine plus amazingly high on the sexual turn on scale. I was very shy around girls & still a virgin until one year later.

I was allowed to take one friend only to our cottage for a weekend. No other family members would be there all weekend. I invited Jake to come with me. We'd planned to meet up with any girls we could find on the public beach not too far from our cottage.

The weekend was a washout with never ending rain keeping us inside most of the time. The first night we watched movies then fell asleep listening to the rain on the roof.

The next morning I was up first. I woke with my usual rock hard erection that would usually not go until I jacked off. I think my sexual needs have always been above average as well as the amount & time I spend jacking off.

I slept nude so I made my way to the front of the cottage with my erection bobbing back & forth like it was hung by a invisible string from above. What I was hoping for was to be caught by Jake, naked with my erection. I always had a secret desire to jack off with anyone who would watch or join me, male or female & until then it had never happened.

I waited for a few minutes then I made a bit of noise hoping to wake up Jake & get his attention. My erection was still at full mast when I finally heard steps coming down the hall. I stood looking out the window with my profile at a good view point for Jake. As soon as he saw me he laughed & made some remark about how the neighbors may see me through the window. Because he didn't sound alarmed I made like it was normal for me to walk around naked at the cottage.

I walked to the kitchen & asked Jake if he wanted coffee. Then I went back to where he was now sitting in the great room & sat down across from him. My cock slapped back against my stomach leaning off to one side. Jake looked down at my cock & remarked that I looked very comfortable. I told him it was how we spent much of our time at the cottage. He paused a few moments then asked if we did the same outside to which I replied "yes but not when there is company" then I told him he was not company so it was OK then laughed.

We drank our coffee & talked about girls. As soon as we were done Jake asked to use the shower. He came back after drying off his hair with a towel wearing nothing else. He walked out & said he should wait to air dry totally before getting dressed but I knew he just wanted to walk around naked like me & I was up for that. My erection was half gone now but my cock was still full & hanging at half mast. I'm circumcised so even with a semi erection my cock's head is exposed & it looks like it's hard. I could feel the excitement in my cock. It was so different for me to ignore the urge to jack off when I felt like that. I could not remember a time when I was naked, erect, excited to the max & did not jack off. I had to endure the sexual pulsing in my cock & it actually felt good. There was this slight throbbing that you get when you are have been erect for a while & first start jacking off even though I was not touching myself.

Now the talk was small & we had nothing to say. We were both thinking about our cocks. I wanted to jack off so bad & I wanted to do it either with Jake or with him watching me but I was too afraid to ask. All I could think of was how I could make it happen so I had to think of something quick. Jake was now sporting an almost fully erect cock too so I knew he was feeling just like me.

I started to talk about girls again. We talked about a girl we both had known for years that had grown into a beautiful woman. We talked about Tara & her great body. Soon we both had rock hard cocks & I was squirming. I had to do something before I exploded! I knew just what to say. I said "OK, how many times have you thought about Tara while jacking off?" I followed up before Jake had time to answer with "I've done it so many times I can't count them" then waited for his reply. Jake was truthful & said he too thought about her quite a bit. "I wish I had some pictures of her nude right now" I said. "My cock needs a good jacking & I don't have any mags up here to use."

I thought that was a good intro to tell him I wanted to jack off right there & then. Jake replied with "what do you use up here, you know to jack off to?" I had to do it. As I told him I had nothing I took my foreskin with just 2 fingers & gently began to slide it up & down. My breathing got chattered & I felt a chill even though I was warm. "Sorry" I said. "I can't go too long without doing it so I'll just give it a few then stop." "No, it's OK" said Jake. "I need to do it too. There's nothing wrong with doing it here, after all we both have the same thing. You know, cocks I mean."

As Jake pledged his case he also began to stroke his own foreskin slowly up & down. "Yah you're right" I said. "It's normal & we need to do it or we'll cum in our sleep." What a poor excuse that was but it was all I had.

I told Jake I'd be right back then I walked away with my hard swaying cock returning with a bottle of lotion from the bathroom. It was an oily lotion that I'd used before & it worked very nicely for long jacking sessions.

I squirted a big shot in my hand & handed it to Jake. I coated my cock then started to draw full long strokes from top to bottom. "Ahhhh, that feels to much better like this" I said. Seconds later Jake was also sliding up & down with slippery strokes. "Oh Yah, this is great stuff" said Jake. "Oh for sure" I said, & you can last a long long time too.

Jake & I sat across from each other jacking our cocks & talking about how we did it & how we learned to do it, how often we did it, how many times we'd done it in one day before & so many other jacking related things. It felt dirty & raw & I loved it! I told Jake we should see how long we could go for before we came. We made a bet of who could last the longest while only stopping for a short bit. We said we could not stop for more than 60 seconds tops & we had to start again after that or loose. It was nothing more than a way to jack off longer but it was so much fun.

We jacked for what felt like an hour stopping & starting so many times. After a while I gave in first & told Jake I had to cum. He told me to go ahead & go first. I was just short of shooting for the last few minutes already so when he said cum I went right for it giving my cock full long strokes. The sloshing sound of my hand sliding over the rim of my cocks head was loud. Within about 30 seconds my orgasm came on fast & hard. I have an unusual & involuntary convulsion like movement that hits me when I cum. Every muscle in my body tightens up & my head curls forward almost like I'm doing crunches. Then my cum shoots hard & many times I end up with a wet cum covered face as my body jerks & my head bobs up & down slightly. I learned to keep my mouth closed even though sometimes I don't on purpose.

After my massive & wonderful orgasm was over I looked at Jake who told me he had never seen anybody cum before. (Later that weekend I found out he was not a jacking virgin). I then watched Jake blast his load of cum. He shot only an inch or 2 but I had no idea anybody could produce that much cum in one orgasm. He gushed twice what I did & it was thick & white. After he came we laughed & rinsed off in the shower. We never dressed, the rain never stopped & soon we were talking sex again. We made another bet to see how many times we could jack off that day. The bet was we would start again one hour after we came. Then one hour after the next time we'd do it again. We stayed naked & did what we said we'd do. We went 7 times in all before we said no more! It was after dinner time & we'd not eaten much that day. We ate a huge dinner of nothing more than burgers & dogs.

The next day we started the same way again. My cock was feeling raw but I was still horny. Jacking with Jake felt so sexually pleasing. By the end of that day we had jacked only 3 times but they were pretty long ones. After that I felt like I never wanted to jack off again. That lasted until I was home ready for bed. I jacked out a nice one while reliving the weekend in my mind.

Jake & I never jacked again & I don't know why. We never even spoke about it.

It was sure a huge thrill when we did though. I'm not sure why we enjoyed it so much. Since then I've never done it with a friend. Many women, no guys.

On 2 occasions I did it in the shower rooms while on business. Once I know I was being watched & it was a thrill. There was only one other younger guy in the showers across from me. No shower doors & I jacked with my back to him watching his reflection in the shinny white tiles. He watched the entire thing & he had an erection he was only too willing to show off as I got out of the shower.

It was fun telling my secret.



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