I was in my 20s when I discovered the shear pleasure of a girlfriend stroking me to a climax. I had gone to an all-boys high school. By the time I started seriously messing around with girls, I was bypassing the fondling stage and going straight to hot-and-heavy sex. I never realized what I was missing until I hooked up with an old acquaintance after college.
Pam and I were fresh out of bad relationships when we started seeing each other. She didn't want to move too fast. I told her I was fine with that. We spent a lot of time talking, hanging out and just enjoying each other's company. One night, after a late dinner at her place, she finally asked if I wanted to spend the night. I was more than ready. I wondered if this might be the magic moment. As it turned out, it would be, but not in the way I expected.
In her bedroom, I stripped down to my briefs and slid into bed next to Pam. I was already getting rock hard with anticipation. As we embraced and kissed, Pam must have felt my hard penis pressing against her stomach. She reached down and touched the tip, which was sticking out the top of my briefs. I was a little embarrassed because this was our first sexual contact of any kind. Here I was with a raging hard-on poking out at her. She commented that I sure seemed ready for something. With that she slid her hand into my waistband and started gently stroking me.
I slid my hand up Pam's t-shirt and started to caress her fantastic breasts. She whispered for me to wait a minute. Then she rolled over and reached for something on her night-stand. I watched as she squirted a drop of lotion in her hand. Rolling back over, she wrapped her moist hand around my penis and began gently massaging the tip with her fingers and palm. She wasn't stroking me as much as she was squeezing and massaging just the tip. The sensation was like nothing I had ever felt. Better than sex really.
She kept squeezing the tip of my penis ever so gently in her palm. I've always been able to hold back from cumming, often stretching my lovemaking to 40 minutes or more. But at that moment I could tell it would take all my self control not to explode in Pam's soft hand. After a couple minutes I let go with a moan. Pam kept massaging me as I released several powerful ejaculations into her hand and all over her sheets. Pam was very experienced in lovemaking, it turns out, but I don't think she expected to get that kind of a reaction. I apologized for not warning her that I would cum so hard. She said it just made it that much more exciting.
Thus began a wonderful period in my life, where Pam opened me to a whole new realm of sex, mutual masturbation and other fun. In fact, the second time Pam gave me a hand-job she threw in a twist. She lay next to me with her head on my stomach and stroked me to a near climax. As she sensed me about to cum, she slid her lips over the head of my penis and took all of me into her mouth. That was my first experience with oral sex. And no mess to clean up.