A had a fling with my friend’s mom when I graduated from HS

In HS, my best friend and I were on the varsity soccer team. We were together all the time. I often stayed at his house, he stayed at mine, we rode to school together, etc. His mom and dad divorced, at some point, and his mom kept the house. The father was a wealthy lawyer, so these people had a ton of money.

His mom looked like the typical wealthy man's wife. She did yoga and Pilates, didn't have a job (thanks to alimony), spend her time at beauty salons, and did I mention she had some big tits and ass!

She was that sexy mom at the soccer games, with jeans so tight her ass looked like they were going to bust out. She tended to baby me, like as if she was treating me like a surrogate mother, but I always felt something "off" about it. She would compliment me (I was very lean, with 8 pack abs back then) on my physique all the time, and make jokes like "Boy, if I was 18 again! I'd be all over you!" She'd also fish for compliments from me, asking if I liked her outfit, asked if I thought she was putting on weight, etc

Well, to speed up the story a bit, she'd pay me to mow their lawn and yes, I'd be shirtless. Bc her son spend time some weekends at his dad's, I'd mow the grass. I use to see her just staring at me and I'd wonder "does she have the hots for me?"

No lie, I'd jerk off to her like crazy. Something about her motherly body got me off better than any girl in school.

One day, after mowing their grass, I was all sweaty and had crap all over me. She comes out in a bikini (they had a pool) and tells me I could shower if I wanted in her shower. So she leads me to the shower and kind of stands there for a minute. I was already shirtless, so I didn't understand. I begin to remove my pants, and am now in my tight fitting boxer shorts. She looks down and stares at my obvious huge boner bulging. Her eyes fixated like she's studying the shape, then she walks out. She's now in the adjacent room. I took a peak, bc I was horny out of my mind, and she was on all fours, huge ass up in a bikini, looking for something she dropped (I think it was an ear ring). I start rubbing my bulge, I was horny beyond reason, but then she turns and sees me and I panic! I go back into the bathroom and she comes in. She sees I'm so embarrassed and starts to tell me it's natural.

I knew things were weird when she asked "do you think I'm attractive?" I answered honestly, and even said I thought she was prettier than the girls at school. She almost seemed aroused by this. She asked if I had a girlfriend, and I said no and that I have trouble dating. She then asked if she could see "it". I said "yes ma'am". I nervously pulled out my penis. I'm a lean guy, I have a long skinny penis, with a curve around the center. Giving it almost a "hump back" look to it. Her eyes got big. She looked like a starving person about to binge it.

"OMG, Dillon! You're HUGE! Much too big for girls your age!" She told me. She was totally Bs'ing me, saying that it might be a problem and said she wanted to check it to make sure it was normal. I, obviously, allowed her to. She starts to run her fingers up and down my penis, rubbing it gently. I couldn't help it, my penis kept jumping and twitching as she'd do it. She asked if it felt good? I answered yes ma'am. She asked if I had trouble having sex with girls, and I admitted I never had sex, only BJ's and mentioned how my ex was afraid of my size (true story). She joked and said this was a "woman's penis" and I needed a real woman for a big penis. She starts to stroke my penis like a pro. I mean I wasn't even that good at stroking it (and, in those days, I jacked off 4 times a day!). She did had one hand at the base of my penis, and the other on the head. She would make her hands meet in the middle, then separate them. She started to go faster and faster stroking my long dick, until she was going at a speed like she was getting electrocuted. It was so good, my leg started to shake like crazy. I just remember hearing her say over and over "come on, baby, it's ok! Cum! Cum!" I remember almost passing out as I came the hardest I've ever cummed all over her big boobs. She laughed it off and stood up and kissed me on the cheek.

I don't know why, but it turned me on when she said "your dick is cute! You're HUGE, don't get me wrong! But it's cute!" I didn't know what to say, my friend's mom just jerked me off. All I remember is her saying "you coming to the pool?" Acting like it was natural.

That wasn't the last time we had a sexual experience. Yes, we eventually fucked.