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First Time Masturbating a Friend

Posted by: Age: 23 Posted on: 14 comments
20 likes 56 views Category: Masturbation Male-Male Tags: Male-Male, Masturbation Male-Male, masturbation, jerking, cum

This is a true story of my first experience masturbating with my friend from college.


So my friend Derek and I had been friends throughout college. He's tall, blond hair, and thin (but still toned). We graduated and lived about 2 hours from each other. We still texted each other, and planned to get together for a week every summer. In college we never really talked about sex or masturbation until one day he made some off hand comment about the myth of getting hairy palms from masturbating. I was a little turned on about the fact that he basically admitted he jerked off (I mean, I figured he did, but there's something erotic about a guy actually saying he does). So of course I responded that if that was true, than I'd have about the hairiest hands alive. I wanted him to know that I masturbated too, and I could tell he was intrigued.  So fast forward to the summer after we graduated. I was over at his house visiting. His room was down in the basement, which meant it was extra private. We hung out and did lots of fun stuff, but then nighttime came. As we were down in his room, we started undressing for bed. He said that he only slept in his underwear, and I said I did too. So off came the pants and everything else. Since he didn't have an air mattress (or at least he said he didn't...hehe) we would share his bed. Well of course I was starting to bone up thinking of sleeping next to him in our underwear.  I quickly got under the sheets so he wouldn't see my obviously almost-fully-erect penis. He got under the sheets too. We talked a bit about random stuff and then he turned the light out. I could tell we were both just laying there thinking about each other, but I was too chicken to initiate. We oh so subtly took turns scooting ourselves closer to each other, making it seem like we were just readjusting ourselves. Of course we knew what each other was doing, and looking back it seems silly that we were trying to be coy. But, I kept on thinking, what if I am misreading his cues and go to jerk off and he freaks out? Well turns out he was much braver than me.  Soon I started to hear the tell tail signs of a hand going under a waistband and some rhythmic moving. I could feel him start to move next to me. So, without further prompting, I slid my hand into my underwear and started stroking my hard cock. After about a minute of listening to each other jerk off, he asked me if I was jerking off. I said I was, and asked him if he was too. He said yes and then asked if I wanted to do it together. I took no time in saying yes I wanted to jerk off with him. So he turned on the light and pulled the bed sheets back. It was the first time I saw his cock (either flaccid or erect). We both took a couple seconds just looking at each other's boners. Then we proceeded to return to jerking our dicks. Then, the best thing happened. Suddenly his hand was on my thigh, and sensing his thoughts, I stopped stroking and sure enough his hand moved to my dick. Spurred by the invitation, I then grabbed his hard shaft and we started masturbating each other. Listening to him grunt and sigh as we both pleasured each other sent me over the edge. Thankfully it did for him too. Within only a few minutes we both were panting and said we were about to cum. We picked up the pace and suddenly there was rope afer rope of hot cum spurting from his dick. He was so turned on, he shot past his head, and one cumshot actually hit my cheek. At the same time, I'm grunting and ropes of cum fly out of my dick. I also shot past my head. I'll never forget the feeling of his hard dick pumping and spewing all that hot cum.  We both just lay there in post-cum ecstasy almost unable to move. We eventually both cleaned ourselves up and **tried** to get some sleep. That only lasted for an hour or so. I woke up again, and wouldn't you know, I was hard as a rock again. I kept on thinking about what we just shared. The weird thing was, I feel like I could sense that Derek wasn't asleep either. So I wanted to test to see if he was still as horny as I was. So I turned so my front was facing him (his back was to me, so we were in good spooning position). I ever so slightly moved myself closer to him so my arm touched his back. Sure enough, he sensed this and scooted his ass towards me. I moved again and made sure this time he could feel my erection against him. Once again he moved slightly so his ass was pressed against my boner. Wtih some courage, I let my arm slip around front and rest on his stomach. When he didn't move or try to pull away, I got bolder and slid my hand down to the front of his underwear. And wouldn't you know, he was hard as a rock too. I started rubbing his boner over his underwear, and then I slowly let me hand slip underneath so I could feel his warm hard shaft again. He let out an audible sigh, which turned me on even more. As I moved my hand down further to fondle his balls, he brought his hand around and started touching me. We kept on stroking each other until once again we blew our loads, this time in our underwear. Needless to say, we didn't get much sleep that night. Hope you enjoyed this true story. I have many more tales to tell of me and my friend's explorations and fun. :)

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