Where it happened: home
My first time was pretty memorable, to say the least, and I can even say it was pretty good. I lived alone with my father in a small, 2-bedroom house, and he dated several sluts and bimbos in the small town where we lived (he was a widower as my mother died 2 years earlier). He also became a raging alcoholic, and one of the women he “dated” was about 45 y/o and they would often shack up together after spending the evening drinking.
My father would frequently bring this woman over (I’ll call her Cheryl) in the middle of the night, and because the house was so small I could hear their lovemaking. However, my dad would frequently pass out the moment he would get in the house, and I would always hear Cheryl screaming at him to wake up.
One night she was particularly beligerent, and I heard her slam the bedroom door shut and storm out of my father’s room. Then I heard my door knob turn, and I realized Cheryl was coming into my room. She then walked over and I heard her ask if I was awake, but I didn’t answer her and pretended to be asleep. I was both scared and excited! That woman then pulled down my covers, and I was wearing only my underwear at the time. Out of the corner of my eye I could see Cheryl taking off her clothes – I had never seen a naked woman before, and the sight of her large, saggy boobs, big nipples, and curly blonde bush was almost too much!
I never stirred as she plopped down on the bed next to me – and on her breath I smelled a combination of cigarettes and alcohol. She started rubbing my crotch through my underwear, and eventually got herself (and my dick) so worked up she pulled down my underwear to my ankles. I then pretended to wake up, and asked her what she was doing. “Just lay still, baby. Your father has passed out, and I need a little cock tonight,” she said.
Cheryl then swung her right leg over my hips and inserted my now-hard penis. It felt so good! She was fairly tight, but EXTREMELY wet. I didn’t know what to do, so I just laid there and let her do all the work. She rocked back and forth, up and down on my cock – her big, saggy tits swaying back and forth. I couldn’t believe it was happening! After she rode me for what seemed like forever she dismounted and put her clothes back on and left that night.
She continued seeing my father for another year of so, and frequently would come into my room at night to fuck me.