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The Second Time Surprise

Posted by: Age: 56 now Posted on: 3 comments
7 likes 6826 views Category: Masturbation Male-Male Tags: mutual, masturbation, sleepover
Side by Side just didn't work.

After the summer there was no excuse to sleep out in Ross' yard so a couple of sleepovers were arranged. His second floor room was at the end of a hallway that started at his parents bedroom (remember the light he kept watching during out first jacking episode?) and took you past a half bathroom. As you walked through the door of his room, to the right was a wall with a small closet and to the left was his single-sized bed. Walking around the end of the bed was the window that faced my house and then there was room to walk past a dresser and it all ended at his bedside lamp and radio adorned night table. He kept his room nice and clean. Some of his art work was framed around the walls of the room and there was a bikini clad girl poster on the back of the door into the room. Because this was planned in advance, which made me hard thinking about it most of the day, I only jacked myself once hoping to have a bigger cum show later. We ate supper then killed the night watching movies. It was very late when his folks turned in for the night. He went into the tiny closet, fuddled around a bit, and came out with a magazine. My cock went stiff as soon I saw the Playboy on the magazine cover because I knew what that magazine was all about. Tipping the mag just over the bed Dolly Read and her tits flopped out onto the covers on the mattress. No more mysteries about tits and I felt the familiar sensation of the first precum kiss the fabric of my briefs. He asked if it made me hard and I told the truth. Then he asked if I wanted to do what we did in the tent. My only hesitation was that the window shade was wide open and the lights were on in his room. My parents bedroom faced his window and the view was only partially covered by a tree we had in the front yard. The shade roll squealed as it was pulled closed. We both dropped our shorts and when I was about to take off my tank top he stopped me cautioning that someone might walk in. He told me to leave my tank on and pull my dick and balls over the top of the elastic band of the briefs. [I was wondering who else he had done this kinda stuff with because I know his folks wouldnt let his girlfriends up there] I was assured that his parents door opening would give us enough warning to quickly pull up our briefs. We were sitting next to each other on the side of the bed with our backs to the door. He reached back for the magazine and was trying to figure out where to put Dolly so she could watch but be safely out of my line of fire. [My cumshot fireworks a few months back must've got his attention] That mag was part of his dads stash and I think he hijacked it just for that night. Dolly was put on the wooden flooring near the end of the bed out of the "stick page" zone. He was asking me what I thought about my first sight of tits and I just looked down at the glistening trail of precum that had run down the bottom side of the shaft and into the folds of my wadded up nut sack. The touch of his hand on my pulsing, aching dick again resulted in a full-body jolt. I reached over and started on him. Well, he hadn't practiced much, if at all, since August. It was all wrong. Our forearms were colliding and the anti rhythm of his technique wasn't getting me anywhere. I stayed hard and kept dripping every time his hand went forward to the head. Then it made a sticky clicking sound when he pulled back down. We both just stopped. It was obvious that we would have to do this one at a time. He said that he'd better go first. I'm the one that wouldn't lose interest after cumming. He pulled my tank so the front was around the back of my neck, told me to put a pillow or two to support my head, and to lay back. Damn, what a turn on to be half naked with all of your sex stuff exposed. To this day I masturbate this same way when time allows. As I leaned back I looked at my erect nipples, flexed stomach muscles, and finally to the hard, shiny, pulsing head and shaft of my cock. The masturbation train wreck started again but, being much more turned on and comfortable, I started to feel the deep tingle and pressure building up in my member. I was near the end of the line and quite by accident part his leg brushed under my calf and I instantly shuddered, spasmed, and gushed forth pearly ropes and puddles of cum. WOW! That's one thing you can't do, surprise yourself near orgasm when you masturbate. I was in an orgasmic daze for a little while afterward. The pillows were moved over and with my dick still weakly pulsing I started to tame his monster. He had incredible staying power [that could have explained the revolving door of different dates but so could that award winning cock of his] I got hard again just watching his abs ebb and flow with my handiwork. It was incredible knowing I was in control of that body and his next orgasm. His balls pulled up so close to his shaft that the briefs band snapped up to cover half of him. I just pulled them away to expose his entire length and continued. Again with only a grunt, yellowish white gobs of semen made the short trip to near his navel. I knew there would be no extra innings for my still hard cock so I started to ready my sleeping bag for the night on the floor. He was still on his back and his dick was fading. I got up and walked past and saw Dolly still watching us. I looked at Dolly, committed her beautiful face, tits, and body to memory, then folded her delicately back into the magazine and returned her to the closet.

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