When I was a teen, I lived next to a family that made my perverted and young mind running wild with thought on both the daughters and their mother. Both daughters were slim, had perfect body and were really nice to me (one was younger than me, the other a little older)... But I was more into their mother.
She was into her 40's, blonde with generous curves and a sexy voice. She used to sunbathe topless in her garden and I used to peek at her from the windows of my own room. It was pretty safe to do that since there was a little hole that I could spy on without me getting caught. Of course I masturbated a lot to her and had my first voluntary ejaculation to her.
One day I got sick, to the point I couldn't go to school and had to stay at home. My mother was experiencing severe panic attack at the time and didn't want to leave me home alone because I could barely stand. So she asked our friendly neighborhood mother to take a look at me a couple of times per day, to make sure I was ok.
Of course my mind was again running wild with dirty thought about me having my first sexual experience with her, so (despite I was really feeling like shit) I couldn't wait for her to visit me.
That day she came to me two times. The first was pretty ordinary... She asked me to take the temperature and made sure I was drinking and taking some medicine to keep the temperature at bay.
Second time was just after launch... She felt my forehead with her lips for a few seconds and was really caring. I, of course, was hard as a rock under my blanket and could easily peek under her shirt as she did that... I had zero experience. But the sight of them alone was enough for me to lose control... The nipples in particular (I saw them always from afar before) were puffy in some way and I dreamed about sucking on them.
She chuckled as she retracted and asked me if I liked what I was seeing but I couldn't reply, I was honestly speechless and unable to even nod. After a few more seconds she said that she was aware of me spying on her while she was sunbathing. At that point I tried to justify that, saying I was sorry and all that. She just smiled, grabbed my hand gently and said that I should do that with girls my age.
I remained silent, so she added that, since I was Ill and curious, I could satisfy my curiosity with her, so she pulled my hand, making me feeling her ample breasts. Unable to hold it anymore I just did that, using both hand and, after a while, getting under her shirts. I remember I could feel my heart on my throat and I was feeling her nipples getting harder under my inexperienced hands.
Without adding anything, she got under the blanket and started to stroke me, gently, getting my boiling teen cock out of my pants, literally giving me an handjob.
As everyone reading this might imagine, I lasted like 10 seconds I think... Before creaming all over her hand. It was my first time I ever touched and was touched my a member of the opposite sex. And boy, it felt amazing.
She didn't mention anything, nor said anything and we both acted since then like nothing really happened... for anyone wondering we moved like a few months after that and she disappeared in Latin America with his husband a couple years later, rumors said they accumulated a few debts with the wrong people.
True story, for the most part.