In the summer of 1984 with my high school sweetheart.
Back in high school I dated a lovely blonde I'll call K. She was so very beautiful at 16, I was a year and a half older than she was. She was in the pleasantly plump category, as I preferred, nicely proportioned thru her bottom and very firm B cup breasts. She was determined to remain a virgin thru high school and I respected that, though she was very adept at getting me hot and bothered anytime we could be alone.
To say I was frustrated was an understatement. At least until the summer after I graduated. Until this point the little sexual attention I got was some half hearted squeezes through my jeans. Jeans that were always stained where the precum leaked through the denim, but actually pooled into little puddles from time to time.
But early this summer day I was sleeping in, my parents were away and I was home alone. The back door was unlocked in the summer because the city meter maid would come in unannounced....a story for another day. K stopped on her way to work at a local country club, and came into my room, sat on the bed and woke me with a kiss. I kind of expected her to and just coincidentally slept nude the night before, covered only in a sheet. As I hoped, within a few minutes of kissing, she noticed the tent forming under the sheet and, for the first time, actually wrapped her fingers around my penis under the sheet. She pulled back from a kiss long enough to ask me 'What do I do now?' I placed my hand over hers and showed her how to move her hand and where to concentrate the pressure. I let her continue on her own and she asked how she would know whether she was doing ok. My breathing soon told her she was doing very well. It didn't take too long until I was at the edge. Her nervous virgin curiosity was really turning me on. Seeing her looking from my face to the sheet wrapped penis in her hand drove me on. I softly panted 'I'm going to look like I'm in pain, I promise you I won't be. When I do, slow down to about half the speed you're stroking me know.' She whispered 'Ok.'
That was when she first made me cum. I bucked my hips and pressed into her neck as it washed over me. She pumped me almost too slow, but it stretched my orgasm on and on. The feeling of the sheet over the sensitive head was a new feeling for me and overwhelmed what I had ever felt before and it left me completely spent and I nearly passed out.
As my erection subsided in her hand, she whispered in my ear that she was going to be late for work and she'd come see me when she got out later on. She kissed my forehead and got off the bed. The last thing I saw of her as she left was her staring into the palm of her hand still wet and sticky from the semen that leaked through the sheets. That was the vision I remembered so vividly as I thought about her after I awoke a while later and touched myself through the sheet as she had done. It was good, but oh so much better by her hand.