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.
My friend's parents got the big D after we graduated. The Dad was a big horn dog and hit the dating scene. The mom was heavy but lost weight and got a job with the same company as I. She and a group of women went to a bar for drinks after work, and she invited me since my apartment was only a hundred yards behind. The group of women was very flirty and insinuated sexual remarks throughout the evening. When it was time to leave, the friends mom asked if I wanted a ride. I replied, "No thanks, I'll walk. It's close." All of the ladies cracked up laughing. As I was walking back it hit me that I just turned down a chance to have a cougar fuck my brains out. To this day, 30 years later, I give her a hug when I see her, and think how stupid I was when I was 22 years old.
It wasn't a friend's mom but a friend of my mom. She was staying with us for a few days when I was fourteen. She was quite attractive, in a milf-y way and I thought about her when I masturbated at night. One afternoon I came home and thought I had the house to myself. In such situations I would take advantage of the opportunity to masturbate in other parts of the house besides my bedroom. I stripped off my clothes and went into the living room. It was only then that I saw that my mother's friend was sunbathing nude on the patio. I hid behind the sheer curtains beside the sliding glass door to the patio and spied on her naked body. She was in her late thirties then, with dark hair and a fit figure for that age lying face down on a chaise longue. From my vantage I had an excellent view of her shapely ass. I stood there in our living room, nude and masturbating, spying on my mom's friend. How awkward would it have been to be discovered in that position? To have someone walk in on my voyeuristic masturbation? Lucky for me, no one interrupted my solo sex spying. She rolled over on the chaise longue, and I had a look at her breasts and her pussy. I recognized from the magazines I jacked off to that she had trimmed back her pubic hair from around her labia, which were clearly visible to my horny young gaze. She wore sunglasses and I assumed her eyes were closed, and as I became more addled with masturbatory lust, I became less careful to hide behind the curtain as I stroked myself. I prolonged my pleasure for as long as I could, but it became too much and I came; I barely remembered to catch my semen in my free hand and avoid making a mess on the carpet! I went back to my room and lay on my bed, spent and aware that I had a memory to revisit during many masturbation sessions to come. I thought that my perverted little whacking session had been unobserved, but mom's friend informed me otherwise. The next morning, as she was about to leave, she took me aside and said she had seen what I was doing the day before. "I think it's hot that I made you horny enough to do that," she said. "In fact, I fingered myself last night thinking of you jacking off to me." I almost fainted from all the blood rushing to my groin. Before I could say anything, she had left. She'd barely driven away before I was nude and masturbating in my room. Those few words have been living in my erotic imagination for going on five decades. And I never got a chance to thank her.
When I was a teenager, I masturbated to anything with a pulse. So yes. I masturbated to my friend's mom often. She was not very pretty. But I masturbated to any woman I knew back then. Also, it was my best friend's mom. I was at their house all the time. Slept over all the time. Since we were best friends, we showered together often. So, it was not rare for his mom to see us naked and it definitely was not rare that we'd have erections when we were nude. That definitely fueled my need to rub one out to her. I never told my friend I was thinking of his mom when we did it. Truth be told, I've always masturbated to my mom far more than anyone else's. For one thing, I saw her naked all the time. So, that just made it easy. But also, I dunno, I've always liked masturbating to my mom.
More my buddies much older sister…. She was more of a mom figure when we were young and when I stayed the night she would help with bath time and ensure all the sensitive bits got a good soaping up. her wet t-shirt nighty left little to the imagination by the time we were getting the towel treatment. she put the “treat” in towel treatment as well. So later on in growing up she was definitely thought of when I had a job in hand.
I'm with you. I was far more turned on by my friends' sisters than their mothers. One of them had a sister who was super athletic. Just a couple years older than us. She wore soccer shorts around the house all the time and I picked some very deliberate places to sit in their living room when she watched TV lying back on the floor with her knees up so that I could see her underwear and sometimes just the edge of her crotch through the shorts' legs. I rubbed out so many orgasms to her white underwear and silky smooth legs when I'd get home from their house. Later, as I got more bold about masturbating outside of my own home, I would rub one out in the basement bathroom of my other friends' house to his twin sister who shared a room with my friend. So lots of bras and underwear to be seen lying around. My sister was never attractive. I always wondered how my friends could handle having such hot sisters when we were that age, just starting out masturbating and the horniest we've ever been towards any female more or less within our age range?!?!?
