I had my first orgasm in an unusual situation
When I was twelve, I had a mild phimosis (this means that the foreskin is too tight). The doctor prescribed treatment with a cream. I had to use it three times a day for six weeks. The doctor showed me and my Mum how to use it correctly. He said I could do it myself. I had to gently pull the foreskin back a bit and apply the cream. He said that in addition, I could pull the foreskin back when I take a bath, but not too hard.
At home, my Mum had to remind me again and again to use the cream because I had lots of other things in mind. I also used to apply too much cream because I thought this would help even more. My mother saw this, and said it would be better if she did it for me. She took the tube of cream, opened it and put a bit of it on her finger. Then she took my penis with the other hand and gently pulled the foreskin back a bit. Then she applied the cream and moved the foreskin back and forth several times. By that time, I got an erection. My mother noticed this and I was nervous because I thought she might laugh at it or something, but she just said that it's normal for a boy and I shouldn't be embarrassed about it. She did it for me the next couple of days and sometimes I couldn't help getting a hard-on but she pretended not to notice it.
When I was sitting in the bathtub a couple of days after, she said I should remember to also stretch my foreskin when bathing. I wasn't sure if I would maybe stretch it too hard and damage it so I asked my mom how I was supposed to do it. She said, well, just do it gently. She said she could show me. She sat on the edge of the bathtub and took my penis in her hand. She took the thumb and two fingers of the other hand and gently moved the foreskin back. It was almost okay by now, it even went all the way back behind the glans again. Then she cleaned the head and foreskin with a bit of soap and moved the foreskin back so it covered the glans again. Slowly my penis became erect. She noticed this and asked me if she should stop. I said no, no problem, and she continued stretching it.
I felt increasingly aroused as she moved the foreskin back and forth and I had a nice feeling in my groin that got stronger as she continued with the exercise. I had played with my dick before when I was horny, but I usually just made humping movements in my bed and enjoyed the nice feeling. I had not had a real orgasm before and I had not really thought much about it either. I felt that the feeling deep in my groin became stronger and stronger and wondered what would happen to me. I must have had a weird expression on my face, because my mom asked me if I was okay. I said, absent-mindedly, 'Yes, why?' She continued, and then I felt an incredibly sweet feeling. I could not help letting out a sigh when I felt my penis spasm and then a clear liquid with some milky bits in it came oozing out the glans. My mother mumbled 'oh my god' and closed her hand around my penis and stroked it slowly and tenderly as more cum came out and dripped into the bathwater. When it was over, my mother looked at her hand. She got some cum on her fingers. She smelled her fingers and then she looked at me, raised her eyebrows and said, 'Well, I hope you enjoyed it'. I stammered, 'Yes it feels good' and she said not too worry about it, it is normal. I said I knew that, I had learned about what semen and ejaculation are but I had not imagined that it would be such a big deal. She said that it is normal for young boys to do this whenever they feel like it.
The next week when she applied the cream and I got a hard-on again she asked me if I would like her to stroke me again so the hard-on would go away. I was surprised that she asked me but I said, 'yes that would be cool'. She took my penis in her hand and started stroking me slowly, this time moving the foreskin back and forth all the way and caressed my balls with the other hand. It felt so good! I closed my eyes for a while as she continued jacking me off and she asked if it was okay. I said 'sure Mom it's great'. I opened my eyes again and I felt so horny that I moved my hand under my Mom's t-shirt and bra and felt her tits. They were nice and firm. She said 'Hey!' but she smiled and called me a horny little SOB. She stroked me faster and finally my penis twitched and spasmed and cum spurted on her leg and on her hand. She kept milking me and her stroking with the cum on my dick made this funny sound. When I stopped cumming, she kissed the tip of my penis and cleaned me off. In the next weeks she did it three or four times for me but I also began discovering masturbation for myself. This was a great time for me.