I had been introduced to 'Karen' by her brother and sister-in-law when she visited our city from out of town and she seemed quite nice. She was rather tall, same height as me (5' 9'), had a pretty face and seemed quite shapely (big hips, thin waist, and nicely rounded breasts.)
Our first visit was rather chaste, just getting to know each other. She was from a religious Jewish family and I too was traditionally observant. I had decided that though I had masturbated for years, and was now in my late twenties, I would wait for my wedding night to have actual sexual intercourse. (The Bill Clinton definition, any other sexual activity short of vaginal intercourse was not really 'sex'.) The 'only' indication of her interest in sex (boy, was I slow) was when she explored my small apartment and discovered my stash of Playboy magazines next to the bed and began thumbing through them with interest. I should probably have said or done something then, made my move, but I had very little experience with women and was rather shy about initiating anything with her at this point.
Once she returned home, however, we talked on the phone every night and our conversations got hotter and hotter and we began talking about sexual activities that we might have together, until we were eagerly anticipating her next visit to our fair city some weeks later.
This time she stayed with a friend not far from my place (very proper and respectable) and I was invited to join them for lunch. We were in the living room while 'Gail' was in the kitchen preparing the meal and we could hardly keep our hands off each other. We french kissed, my very first time, and even felt up each other a bit. I don't know how I did as a kisser, but it sure turned me on. After lunch, which couldn't end soon enough, we decided to go for a walk and, of course, ended up at my place where we picked up where we had left off at Gail's.
I made it known that my body was hers to explore and Karen was also open to exploration, though she said she hoped I wouldn't be disappointed. I soon saw what she meant when I unbuttoned her blouse and undid her bra to see that much of the curvature of her chest came off with the padded bra. Her breasts were actually rather unusually shaped, her left one quite tiny and the right one somewhat bigger. But they felt great. She was now down to her pantyhose and refused to take those off explaining that she was having her period and needed to leave them on this time.
She had been busy herself while I was undressing her and had stripped me naked and was exploring my penis which was not particularly large but had grown hard and erect from our explorations. We ended up on the floor and she asked me to play with her breasts and help her get off that way. I was happy to do so and rubbed and squeezed them until she came. The sound of her heavy breathing and sighing made me even harder.
Then she returned the favor and stroked my cock for me. It was the first time I had a woman touch me, though I was very experienced touching myself. I adjusted her hand so that she would do it with the right speed and the right pressure. I usually take a while to come and so she had to work at it a bit, but ultimately I came all over my belly. Wow, an amazing experience! Why had I waited so long to do this with a woman? Unfortunately, she had to leave that night and so it was again some time before we got together and tried it again, but by then we had a wide range of experiences which I'll save for the next time.