1. Captain Cougar


    Date: 1/30/2016, Categories: Fantasy, Anal, Blowjob, Male / Older Female, Author: Slipknot21, Rating: 91.9, Source: sexstories.com

    When I was a teenager, my friends always found it strange how I never had a girlfriend. I mean, I’m not an ugly lad, I wasn’t back then and I’m not now, I was always and still am considered to be above average, I’m 6’0 ft tall, I’m in shape, with blue eyes, and brown hair, a born and bred rocker, jeans and a band t-shirt all the way, usually Iron Maiden. I’m nice and will do anything for anyone that I care about. My problem was not that I couldn’t find a girlfriend; it’s that I didn’t want one. My interests landed squarely in the lap of older women, I found girls my age attractive, but I was mainly turned on by milfs, more importantly, cougars. It didn’t help that most of my friends had hot mums, and at 15 I was embarrassed by it. It all started when my mum used to have a friend called Diane, I was 13 at the time, and she always used to take my breath away. It didn’t help she liked to dress a little slutty and with her body that was impossible to ignore. She was a fitness freak, always toned, with paleish skin short blonde hair, large breasts and a firm tight looking arse. She was the one I masturbated through puberty to. She left the area when I was 15 and we lost contact with her. When I turned 16 (16 being the legal age to have sex in England) I decided to get a girlfriend my age, because at this point, my friends thought I was either gay or something else, so I began to date a girl called Lauren, long brown hair, dark brown eyes with a naturally tanned, slim body, with ...
    lovely breasts and a gorgeous small yet firm arse. I was attracted to her, and when I lost my virginity to her, the sex was amazing; I just couldn’t help but be more attracted to older women. My first sexual encounter with an older woman came from my oldest friend Tim’s mother Debby, she had known me all her life, seen me almost every day for 17 years and I was practically a son to her. At the time she was 38, with black hair, blue eyes, pale skin and a body to die for, half way between chubby and slender, with wide hips, a gorgeous round arse, and breasts that were still firm, and a good handful. She always wore long hippy style tie dye dresses, wore out of fashion flip flop shoes, and long sleeve cardigans. One day while at Tim’s, I had accidently seen her in the shower, I got a huge erection, it was my holy grail. I decided that day would be the day I gave it a shot. Later on while she washed dishes, I purposely spilt a glass of orange onto the table, made to look accidental obviously. “Will, you clumsy idiot, come and get a cloth and clean that up” Debby had said with her usual playful banter. I walked over to her, an erection raging in my pants, this was my big chance, I leant in from behind, making sure she felt my cock, I knew she had, her face went red. I reached round, took the cloth in my hand, pushing my hips as much as I dare into her without my friend noticing. She had become flushed, the seed of the idea was planted in her mind, she would be thinking of that all ...
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