When I was 27 I was single and was meeting women via personal ads. I met a really nice woman named Helen and we hit it off right away. We connected on a number of interests and our life philosophy was similar, but we were also really different. But we started dating and became good friends. Our dates progressed to intense make out sessions, and man could she kiss. We talked about our past relationships, and she let me know that she had been verbally/sexually abused when she was young, and had trouble letting herself be intimate with men. This was ok with me, I liked her and hoped that as our trust deepened so would our intimate contact. But boy did I go home with aching erections in need of attention!
One night she was over and we ended up making out on my bed. Somehow we progressed to taking our shirts off, and I thought the time had finally come to consummate what we had been building up to. But after some more kissing, she started to gently cry. I held her tightly and whispered that it was ok, that we should wait until she was really ready. She thanked me and we snuggled on the bed until she calmed down.
And then she really surprised me. She started caressing my chest, and slowly worked her hand down to my jeans button. She looked at me and said, 'You've been so sweet and patient, that I want to do something for you.' And with that, she unzipped my fly and reached into my boxer shorts! My god, I almost came instantly! 'Are you sure about this?' I asked, praying that the answer was yes. Her answer was to pull down my pants and yank them off.
She then proceeded to gently stroke and caress my straining hard on. She cradled my balls in her left hand, while quickening her pace with her right hand. She could sense that I was close, and as I got to the edge, she stopped stroking and just gently squeezed my shaft in a slow, rhythmic pulse. This kept me right on the edge for a second, and then I let out a low moan as wave after wave of cum shot out onto my chest. She milked my penis until I was totally spent.
Soon after this we broke up before we could go further in the relationship, both knowing that we weren't right for each other. Funny thing was, shortly after that we got back together and started a 'friends with benefits' relationship, which led to some of the best sex of my life! With the pressure of a relationship gone, she really opened up to me, and I was a big part of her sexual healing process. Our families are now good friends, and I look back on our days together with great fondness.