This is how I was introduced to the great pleasures of masturbation. It is a day that is imprinted on my memory and something I regard as one of the longest lasting gifts from my stepfather which I was only ever able to repay in part.
My Mum remarried when I was eight and we went to live about 150 miles away with Andy. I don't really remember my real Dad but I thought Andy was pretty cool and I'd got to know him well over the two years before Mum and him got married. He certainly wasn't the fearful stepfather type and we became firm friends and remained so until he sadly died a couple of years ago.
He had a great sense of humour and was so full of stories I would listen for hours about his exploits. He would always take time to explain things (Mum didn't and would often lose it if I couldn't grasp a new topic in homework) and seemed, especially when I was younger, to know about everything. He was in every sense the father I'd not had before.
Just before my 13th birthday after listening to some of the other guys at school talking about wanking and how great it was to cum I came home determined to give it a try. I'd had plenty of erections of course and knew that when I touched myself it felt good but I'd never cum and didn't really know what to do-even if I'd told my friends that I did.
I knew Mum and Andy were out at work for another couple of hours so I went up to my room and stripped off. I was quite excited by the idea and already had an erection. So I lay on my bed and started stroking my dick. I tried rubbing it, stroking it again then rolled over and rubbed it against the bed but whilst it felt good nothing 'big' seemed to happen. I gave up for a while and went and got myself a drink but I had made up my mind this was going to be the day so I soon went back upstairs for another try.
A few minutes later I was back on my bed stroking my rock hard erection again when suddenly there was Andy standing in my bedroom doorway. I had been so engrossed I'd not heard him come in, come upstairs or walking down to my room. 'What ARE you doing son?' he said and walked straight over and sat down on the edge of the bed.
I was frozen, dick in hand and completely dumbfounded. I knew Andy's manner and he clearly wasn't angry but was just asking a genuine question but I still couldn't answer. My dick had now shrunk and I reached over and pulled the sheet over me to cover my embarrassment and all I could get out was 'Sorry, Andy'. He bent down, picked up my clothes off the floor where I'd left them, handed them to me and said 'Come on, get these back on and I'll see you downstairs in a minute or two.'
I was convinced I was in trouble as this was Andy's normal way of doing things. I'd get a lecture-no shouting-but I'd know I'd done something wrong. I was also concerned what would happen when he told Mum because this was sure to cause her to flip. Me caught, naked, erection in hand. I thought this had to be a serious grounding at the very least.
I sheepishly went downstairs where Andy was sitting out on the porch and repeated my apology but Andy immediately told me that I had nothing to apologise for but it was him who should apologise to me. He went on to explain that wanking was perfectly normal and that everyone did it-including him-and those who claimed they didn't were either lying, deluding themselves or didn't understand the phrase! He told me that I really didn't have to be embarrassed about it although it is something normally done in private and that he should have been more thoughtful before walking into my room. Besides, he had come home early and I'd thought I was on my own.
He then said that it didn't seem that I was very experienced as my technique was not particularly good. I told him (lying as I was embarrassed about admitting I'd not actually done it properly) that I'd only tried it a few times and was still getting used to it. Andy explained that he had started wanking when he had been around the same age as me and that he had been shown how to do it by his older brother. At this point, feeling more reassured about my position I said 'Well, I don't have a brother so I'm figuring it out for myself'.
Andy was quiet for a few moments and then asked me if I wanted him to show me how. I agreed and he told me to go back to my bedroom and get comfortable. This was starting to get quite exciting and I had real butterflies in my stomach as I happily tripped back upstairs and stripped down to my briefs and lay down on my bed. Andy came in just behind me, having changed out of his work clothes, and sat down on the bed next to me. 'You'd better get started and we'll go from there he said.
I slipped my hand into my briefs and started to rub myself but couldn't get an erection again even though I was quite excited. 'I can't get a boner' I said and with that Andy leant across and started to gently rub my dick with the palm of his hand through my briefs. 'How's that?' he asked. I have to admit that this was the first time that anyone had ever touched my penis-other than when being washed as a kid-and it felt so good I was hard in seconds. Andy then told me to start wanking and so I slipped my briefs down over my hips and got going by rubbing the shaft of my dick with my fingers. 'Does that actually feel any good?' he asked and I admitted that it was OK but I think he knew I hadn't got a clue.
With that Andy came around to the other side of my bed so he could take hold of my dick with his right hand and proceeded to use his forefinger and thumb to gently rub my dick up and down, just below the glans. This felt completely different and far better than what I'd been doing and I told him straight away that it felt really good. I could feel my dick pulsating every now and then and it was very hard-probably harder than it had ever been before-and I just lay back, thoroughly relaxed. The pulsating in my dick was getting quicker and Andy obviously felt it because he slowed right down and asked me if I could feel anything different. I told him that it felt more or less as though I need a piss but he assured me that that was normal and I wasn't going to do that and to relax again.
I laid back and Andy picked up the rhythm again and the pulsating soon came back. Faster and faster until I felt that peculiar tingling starting between the legs then suddenly moving up your dick and overtaking all of your senses. I squirted a few drops of clear liquid onto my stomach and knew I'd cum at last!
After a few seconds, I suppose, Andy asked me if I was OK but I'm sure I had a smile on my face as wide as a mile because he just smiled back. 'Welcome to manhood' he said and passed me some tissues he'd brought with him.
I had several more lessons with Andy over the next few weeks and months but have to admit that whilst he encouraged me to try out the various techniques he showed me for myself I secretly always enjoyed it most when I managed to persuade him to wank me off again. I'm sure, now I've been married myself for a few years, that that was all to do with feeling secure and protected rather than having to be furtive and rushed.
Our holiday that year was particularly memorable from a sexual point of view but that will have to be a separate story.
Finally, I was able to repay the favour to a degree when Andy was ill, sometime before he died. I had spent the afternoon with him going through some business papers and he was feeling quite tired and uncomfortable. I asked if there was anything else I could do for him before I left to go home. I was surprised when, almost certainly as embarrassed as I was that afternoon when I learned for the first time the mystery of the orgasm, Andy asked me if I could 'help him out' and give him a wank. He'd not had one for months as both of his arms were weak and, sad as it seems, he couldn't grip anything. I happily agreed and will always remember the smile on his face when he lay back on his pillow afterwards as it almost certainly mirrored the one on mine that spring afternoon all those years before.