This happened when I was 19 years old in the summer after graduating high school.
I went over a friends house to see if he wanted to play softball that afternoon. His step mother said he was out and wouldn't be back for several hours. She could tell I was overheated from riding my bike in the sun, and she invited me in for a cold drink.
Jack's step mother was a common topic of conversation for our group of guys, as she was 31, much younger than his father, and really good looking. On that day she had on some tight shorts and a small top with the ends knotted, so her flat stomach was showing. She looked hot and she smiled at me when I noticed.
She got a lemonaide for me and we sat at the table where she had a bunch of magazines laid out. Right on top was a Fredricks of Hollywood catalog. Any male growing up at that time will immediately recognize that name. Hot stuff.
She saw me looking at it, and asked if I liked the pictures. I was really embarassed, but I looked right into her eyes and said I loved them. It was clear that she was in a racey mood and she told me that Jack always fishes the old ones out of the trash and hides them in the top shelf of his closet. She asked what I thought he did with them.
I looked away from her. I had never been around a girl that bold, and now that a grown woman was talking to me like that I was too embarassed to answer. I thought I was pretty hot stuff at the time, but now that I look back on it, I was just an inexperienced kid. She put her hand on mine and squeezed it. Then she asked me to look at her.
'He plays with himself-jacks off-doesn't he?'
'I guess so.' I answered.
'Do you jack off?'
'So do I. Women don't call it that, but we do it. Especially if we don't get what we want from our husbands, like me.'
Then she slipped her free hand off the table and put it between her legs. Squeezing my hand, she closed her eyes and started rubbing herself. I was amazed, and my cock got so hard so quickly that I wanted to reach down and straighten it out. I squirmed a little in my chair, but it didn't help.
'Go on, reach down and touch yourself' she said.
I used my free hand to unbutton my pants and position my cock so it pointed straight up with the purple tip showing itself above my waist band. She moved her chair so it faced mine and asked me to face her. There I sat with the head of my cock in full view of her. That was a first for me and although I was nervous, my cock remained huge.
'Let's get a little more comfortable,' she said. She untied her top and pulled it off, then off came her bra. 'Lose your shirt,' she said. I complied.
'Pull down your shorts so I can see everything,' she said. I did.
Then she unbuttoned her shorts and pulled them off, so she sat there in her tight panties. There was a definite wet spot between her legs. I could smell her and my cock ached from being so hard. I looked down and a little clear liquid had already oozed out of the hole and run down my shaft. 'You're ready, aren't you?' she asked. I nodded. 'Don't touch yourself, just watch. Try to hold it in.
Then she slipped one hand into her panties and rubbed herself in slow grinding motions. With her other hand she played with her nipples, rubbing them and piching them. Once in a while she opened her eyes to look at my cock, and then she closed them and whispered 'Fuck, fuck, feels good, wet, hot, fuck....' After a few minutes she asked if I liked what she was doing. All I could do was nod yes.
She moved her chair closer, sat on the very edge, and put my knee against her pussy. 'Move your knee up and down and make me come!' I did it and in a moment she was panting, 'FUCK, FUCK, FUCK !!!' Then she tightened up and slammed her legs together against mine. She trembled for a long time, jerking a few times to get the last contractions.
She opened her eyes and looked at my cock. I had squirted all over my leg and onto her tits without even touching myself, but I was still hard. She scooped up my cum and wrapped her hand around my shaft, rubbing the liquid onto me. I felt myself getting really hard again.
I remember her saying 'Squirt baby! One more time for me! Squirt for me!' It took a while, in fact she had to get some oil and put it onto me because she rubbed me dry, but after a long time I felt my second climax building.
As she stroked me, her other hand was rubbing her pussy. Then I came again. Not as much juice as the first time, but the feelings were more intense because she was jacking me off. As she coaxed all the cum out of me she made herself climax again.
After she came, she put my cock in her mouth and gently sucked on me for a long time. Eventually I got hard again, but I wasn't able to squirt. She kissed me for a while and then led me into the shower. While we were there she had me put my finger up her anus while I put another finger inside her cunt and wiggled it gently. I did that for her until all the hot water ran out, at least twenty minutes.
We dressed and she asked me never to tell anyone about what we'd done. If I kept my promise, we'd be able to do this again. I never told anyone about that day until now.
After that day, she gave me many more lessons. It was as good as it gets for a horny 19 year old!