I read a few similar stories, and I thought that I would share one of mine.
At about the same time I had just started puberty, I figured out how to masturbate to orgasm and ejaculate. I had rubbed myself lots of times, as all boys do, but never had an orgasm or ejaculated before I had sprouted a few hairs on either side of my penis. Well, as we all know and do, I spent every second I possibly could masturbating. It didn't matter where I was or who I was with, I would always manage to find a place to do it. I would usually try to find a bathroom, but I even managed to do it in the back of the family van one day, when I went grocery shopping with my dad and I had to sit in the back seat to hold a few things from rolling around as we drove. I found some old, unused tissues in my jacket pocket, grinned to myself, rested my head on the back of the seat in front of me and went at it.
Well the more times I did it, I realized that when I had an erection, I couldn't get my foreskin back any further than about half way down my penis head. I messed with that a bit, trying to pull it a little further, but any further than slightly past half way hurt like hell. So one day, after obsessing over it for a few days, I finally told my parents. In my house nudity wasn't really an issue. If someone was naked for whatever reason, usually after a shower, and they were seen, it was no big deal. We wouldn't go running for the nearest room or fumble with something to cover up with. Just carried on as usual. Also, at my age, there wasn't really much to hide anyway, other than the obvious signs that I had been masturbating. But I made sure there were none and any redness that usually followed a masturbation session would just be blamed on my current problem and discussion.
So when those few words that most people dread, 'Let's have a look' came up, It took no courage at all for me to do. As usual for my age, by the time I got the zipper on my pants down, I already had an erection. Which suited the situation just fine. So I showed my parents my problem, they had a close inspection, eyes only. Asked me a few questions and I explained that it only wouldn't go back when I had an erection. Although I could never actually prove it, at that age I was the only one who ever saw my penis limp, as if it was exposed for more than two seconds it was erect. So after they had seen enough, my mom made a doctors appointment for me to get checked out. Though I don't think they were really all that worried and the appointment was really more to just reassure me that all was well.
The day of the appointment came. 'Drop your drawers' the doctor said as he snapped on some rubber gloves. I nervously pulled my pants down and laid down on the table and as usual, I was already erect. The doctor gently and slowly pulled my foreskin back and asked me to tell him how far back he could get it before there was any pain. He reached the point, I yelped and he marked a few things down on his clipboard. Probably seeing this dozens of times before, he said it was just a little bit of tightness of the foreskin, nothing to worry about and my orders were to take hot baths and keep trying to pull it back.
So the first thing I did when I got home was start the water for a bath. While undressing, I realized that I was just given the best excuse to sit in a hot bath and play with myself. Better still, I didn't have to hide it or rush it. I had all the time and privacy I wanted. My parents knew exactly what I would be doing, or so they thought, and I was sure they wouldn't interrupt. Even if they did, I had the perfect excuse. Naturally I took advantage of the situation and started a long, slow masturbation session. I would bring myself as close to orgasm as I could without climax then stop and relax, pulling the foreskin back as far as I could a few times between rises. After doing this a few times, my penis became pretty red. Especially the foreskin.
So I figured it might be time to finish up and get out. But I was still going to take my time.
As I lay in the tub, with my eyes closed, slowly stroking, I heard someone walking toward the bathroom door. I thought to myself 'Nah. They can't be coming in here, they know what I'm doing.' Well just in case, I made myself look a little more uncomfortable and started to stretch the foreskin back like I was supposed to. There was a knock at the door. 'yeah?' I nervously answered. The door opened and in walked my dad. 'How are you doing, Any change yet?' Thinking that they were expecting some results, and not wanting them to know what I had really been doing, I said there had been some improvement. My dad knelt down next to the tub and asked that I bring my penis out of the water so he could have a look. 'Wow. It's really red. Does it hurt?' he asked. 'Not at all' I said. 'Well let's see how much improvement there is. Pull your foreskin back as far as you can' Keeping my penis above the water, I pulled my foreskin back as far as I could, hoping that there really had been some improvement. 'Yeah, that's a little further than before. Looks like it's working, eh?' I agreed.
'Let it go forward again then try to bring it back a bit further' I followed his instruction. 'One more time. Keep trying to get it back just a bit further than the last time' As he was finishing his latest instructions, my mom walked in and quietly asked how it was going. 'Great' my dad said, sounding pretty excited. 'Yeah. I think it really is working' I agreed. 'Can it go back a lot further? Let me see how far back it goes now' I raised up a bit more out of the water and slowly pulled my foreskin back. To my amazement, it actually had been working. I got it back slightly further than last time. 'I don't see a difference...' My mom said. 'It goes back a little bit more each time he tries. Sam, keep doing it like I said. Let go and try again, it looks like you might be able to get it back all the way soon.'
Again, I did. Only this time I had to slow it down a bit more. I was still pretty near orgasm from spending all that time masturbating. 'Again' My dad demanded. Hoping that this was the last time, again I let go and pulled back. 'Oh, I see it now. That is a bit further' My mom pointed, also excited. 'Look, it's almost near the edge of your head. Keep trying.' It really was, but I was very near orgasm at this point. 'I think I should stop for a bit.' I said, gritting my teeth. 'Why, is it starting to hurt now, Sam?' My dad asked. I took advantage of the most obvious excuse. 'A little bit.' 'Look how close you are. Don't give up, you almost got it all the way back' Like a father cheering his son to a touchdown. 'Just try a few more times, Sam' My mom asked, looking sympathetic. 'I can't' I said, looking up at her with pleading eyes. 'This is important.' She said.
My eyes back on my penis, I pulled back my foreskin again. Trying to fool them, I pulled back a little less far and with a looser grip than I had before. My eyes widened and I had to take a deep breath that time. 'Don't quit.' My dad sighed. I looked up at him and he raised his eyebrows and motioned with his hands for me to keep going. 'Almost there.' I sure was. But they had no idea. I guess my parents really didn't know I had been masturbating these past few months. Otherwise they probably would have known that given this opportunity that's what I would have been doing, and they wouldn't have come in to coach me this way. All that time I spent worrying and feeling guilty after my past sessions, like they knew, was for nothing. well it was about to be known now. I knew that if I stroked one more time I was going to squirt. 'This time try to get it past the head.' They wouldn't take no for an answer. They rarely did. So I started to pull back on my foreskin, my face tightened, eyes closed and feet clenched. Right as I felt my foreskin get to the very edge of my penis head, my legs kicked and hips thrust upward, making quite a splash. I was at the point of no return now. Orgasm.
I didn't want to, but it was way too late. My body stiffened, my eyes went wide and I held my breath as I ejaculated nearly straight up in the air. With orgasm still in control, I kept stroking lightly, as I always did, until I was sure it was all out. Then my body relaxed, I put my hands and my sides and lowered my gaze in shame of what I had just shown them. After what seemed like forever, I finally looked up to face the music. My mom was staring in shock with her hand covering her mouth and dropped jaw. My dad had taken a few steps back, and was staring the same with surprised eyes and sort of a half smirk. I was in for it now, I thought. 'Oh, dammit.' My dad said, with a light chuckle. 'You could have just asked for some privacy. I thought-at your age... Sorry, Sam' I looked up at them, extremely puzzled. 'You'd best get out of that dirty water.' Then they both walked out and down the hall, whispering and giggling. I just sat there confused.