One of my high school friends mom is super hot. At 5'4", 110lbs, tits just a little big for her frame, large areolas with thick nipples and fit. In public she dresses conservative but when home, WOW. Usually braless with a slightly snug shirt and low cut short shorts. At 15 I am almost 6 foot, ripped and play football. Her husband is 5'7", a vary average business type person and traveled a lot. We lived next door to each other and I was always over there days and nights. One time I was there all day and spent the night. That day, she was showing off a little more than usual. We went to bed around 10:30, my friend was out like a light, an earthquake would not wake him. It was 12:30, I could not sleep with an erection while thinking about his mom and did not want to wank off with my friend in the next bed. I quietly walk the the bathroom and looked over the rail down into the living room. I saw his mom laying on the couch, one foot on the floor and the other over the back of the couch with her hand rubbing under her pants. I was mesmerized watching her. She started moving her hips up and down and quietly moaning. This became a little louder and movement was faster and harder. After a few minutes of watching her, her whole body became stiff with her legs straight out, her head moved back and she began to shake while still rubbing under her pants. This went on for about two minutes before she went limp. She laid there very still, just breathing very hard. I went back to my room and noticed my pj's and willie were very wet and sticky. That was the first time a saw a women masturbate to orgasm. The second time is pretty much the same during the day. That night, my friend was dead to the world and I could not sleep. I was thinking about watching his mom rubbing herself, and my cock was very hard. I got up to see if she was on the couch again, she wasn't. I heard a noise coming from her bedroom. I want over to see what the noise was. The door was open about half way and I saw her on the bed on her knees facing the head board. I didn't know what was happening at the time but it turned me on. She was slowing moving something in and out of her body. I took my cock out started rubbing while watching her. I shot my load in about three seconds but stayed to watch her. My cock became hard again. She started breathing very hard and fell onto the bed grinding her hips on the bed. She stopped moving and laid there very still breathing hard. I quickly went back to my room. She looked at me differently after that night. She must have realized I saw her when she cleaned up the mess I left on the floor at her door.
I was sixteen and had a really hot girlfriend and her Mom sometimes dressed in a button down shirt which was usually unbuttoned but tucked into a pair of bluejean shorts that were cut short. She never wore panties or a bra and I got a regular view of her small tits and hairy pussy. I jerked to her as much as I did to my gf and occasionally still do. They were both delicious and I wanted to bag them both.
I guess this counts. Technically, my mom had a friend that rented out the apartment upstairs. I became friends with her two kids. Anyway, I was a teenager and she was a sexy Latina in her mid to late 30s. Very sexy. Always wore heels that drove me crazy. I would masturbate thinking about her. She used to leave her heels outside in front of her door. One day I got brave while she was downstairs talking to my mom and I went up the stairs to take a sniff of her heels. Well, she ended up walking out my door and looked up & saw me smelling her shoes. She asked what I was doing and I told her that I smelled something and wanted to know if it was coming from her shoes. She ended up squeezing my balls through my jeans and told me that she would tell my mom what I had done if I ever did it again. One day I went up to see if her kids were home to play. She said they were with their father. I couldn't help, but notice she was wearing these high heel mules. I was staring at her feet in the shoes when she grabbed my balls again and said "remember what i told you about telling your mother ". Except this time I got hard and she noticed. She moved her hand from my balls to my cock. I was hard and she called me a little pervert. She didn't take away her hand and next thing I know I shot a load within seconds. This time she said don't tell your mother. She moved out a couple of months later. I don't know how many times I masturbated thinking about having sex with her. Now I'm like, well, I was a teenager. Probably not above board, but whatever. Definitely fueled lots of stroke sessions and in a way, my first time cumming with someone else.
