Looking back over my 71 years of life, one thing has become very apparent to me. I have always had a passion for mature women starting at a very early age.
Growing up in an upscale, affluent southern California beach community in the 60's we were provided with almost more exposure to women than we could handle.
Most days during summer I would hang out at the beach with my 18 year old buddies trying to pick up 18 year old teenage girls for any sexual adventure we could get. I would say we were pretty typical 18 year old horny teenage boys.
Most of the time we would hang out with teenage girls our own age. It was interesting to see how their bodies would develop from one year to the next especially their tits. Every year it also seemed that their bikini's got skimpier as they got older and hornier and became more comfortable with their bodies.
By the time we became 18 year old high school seniors we were screwing a select group of young women, including most of the cheerleaders. As our reputation grew, we even started screwing some of the cheerleaders from other high schools.
We paid particular attention to the girls from Catholic schools that seemed to have an insatiable craving for cock. They were anxious to share their developing teenage bodies with us, and we were more than glad to take advantage of their generosity. 18-year-old teenage pussy was not only an obsession, it became a lifestyle for my buddies and I.
However occasionally we would step out of our comfort zone with teenage girls and shamelessly try to pick up some older college girls. If we were really feeling bold, we would approach single women in their 30's, 40's and 50's who were at the beach by themselves.
We had a certain amount of success with older mature women who were totally flattered and turned on being picked up by 18 year old guys with flat bellies and hard cocks. In today's world, they would be known as cougars or milfs. They were definitely old enough to be our moms and we fucked our share of them.
We would pick them up by making some very direct, sexually suggestive comments to weed out the women that were potential targets from the ones that wanted nothing to do with us. We discovered that a lot of these mature women wanted to fulfill their sexual fantasy of being fucked by teen boys with stiff hard cocks to remind them of their sexual youth.
There were also some women that were no longer getting enough cock at home either because their husbands were no longer interested in them or they couldn't get an erection anymore. We gave these mature women all the hard teenage erections they could handle plus some.
We also found out that some of these mature ladies liked to role play being a damsel in distress. They wanted to be forcibly stripped, tied to a chair, bound and gagged, roughed up a little bit, tied to their bed and then eventually hard fucked as they were acting out their sexual fantasies. Seducing these milfs is where I believe I developed a love for True Detective magazine and the damsels in distress sexual kink.
As I got older progressing through school my interest in girls and women continued. I became particularly interested in my mature skirt wearing high school teachers and college professors. They became very easy targets to get an up skirt shot of their mature legs, thighs, and panties.
I also found it to be very easy to maneuver these unsuspecting and somewhat naΓ―ve, mature women into position, so I could clearly look down their blouses and pretty much see what color bra they were wearing that particular day. I eventually shared my technique with my buddies and as a result we became good friends.
When I was an 18 year old senior in high school, I had an event take place that definitely fueled my erotic interest in mature women. I clearly remember innocently walking in on my new stepmom Cathy one day when she was stepping out of the shower. My dad had just remarried and she had recently moved into our house with my dad and I.
Cathy was in her mid 40's and was truly a hot milf. My buddies were totally jealous that I was going to be living in the same house with this very busty red haired mature stewardess that was every young man's sexual fantasy. I had been with a number of girls my age, and with a couple older women that we had picked up at the beach, but Cathy took the whole concept of a milf to a new level. It was even more erotic that she was my new stepmother.
As she stepped out of the shower I froze and just stood there unseen for minutes mesmerized enjoying watching her dry the glistening shower water off her mature body. She had no idea I was standing there and I had no intention of leaving as I watched her big tits hang and sway as she leaned over to dry her tan thighs and legs. She finished drying by rubbing the towel between her legs to dry off her red bush that appeared to be immaculately trimmed in the shape of a heart.
When she finally looked up and saw me, she was caught by surprise. I was casually leaning against the bathroom doorway with my arms crossed shamelessly looking over her mature body from her toes to her head, and everything in between.
I thought she was going to go crazy and start screaming at me for being a pervert or even worse by telling my dad that I was creeping on her. Instead, she dropped her towel, put her hands on her hips, making no attempt to cover up.
She casually looked at me and said, "Well Jimmy, I hope you're enjoying the view. Is there something you needed to talk to me about?"
I was totally tongue tied but I finally stuttered out, "Yes, but we can talk about it later."
I turned around and started to walk away to get out of this awkward situation with my mature naked stepmom but it seemed as if she did not want me to leave. She immediately stopped me, "Wait Jimmy. Come back over here and pick up my towel for me young man."
It immediately hit me that my 40 year old, big tit, sexy stewardess stepmom was messing with me. It seemed as if she was trying to embarrass me with her intimidating mature milf body by keeping me there and engaging me in conversation. I was more than willing to play her game.
I slowly, and arrogantly walked towards her now realizing what she was up to and I was totally into it. I mean after all, how many times in my life was I going get a chance to fuck around with my naked stepmom standing in front of me taunting me with no one else around. I definitely intended to take advantage of the moment.
So many nasty ideas were running through my mind with my naked mature stepmom standing in front of me apparently challenging me to do something.
I considered grabbing her, giving her a deep tongue kiss and aggressively squeezing her tits. I thought about approaching her, putting my hand around her throat, grab her heart shaped pussy and finger bang her while her pussy was still wet from her shower? Should I grab her and drag her into the bedroom and violate her mature pussy on her own marital bed? It would've been so easy to overpower her and do anything I wanted to with my new prick teasing stepmom.
I eventually decided to slowly approach her and pick up her towel as she requested. I slowly bent down on one knee and took my time staring at her soft underbelly, her red haired bush, and her tanned firm thighs. I picked up the towel and handed it to her catching her off guard by shoving it into her stomach, almost as if I was punching her in the gut.
Looking back I'm not really sure why I sunk my fist into Cathy's soft belly. Could it have been the result of pent up anger towards my new stepmom? Was I jealous that my dad got to fuck this gorgeous woman every night and all I could do was listen to them from my bedroom? Was I upset because she was obviously playing this cruel teasing game of exhibitionism with her new teenage stepson?
I'm still not sure what the answer was but I know I loved the feeling of her soft belly as it absorbed the blow of my fist. It felt so good that I just kept my closed fist up against her belly as she gasped and doubled over at the waist trying to collect her breath.
It felt so good and erotic that I wanted to give her another punch and really punish her but instead I focused on the feeling of her large, mature tits, draped over my forearm. She was trying so hard to regain her breath that she didn't realize she was letting her 18 year old stepson feel up her 45 year old milf tits as if she was one of my 18 year old girlfriends.
I took a couple steps back and admired her hanging, swinging tits as she slowly regained her breath. As she stood straight up, I noticed something else that I didn't expect. Her nipples were rock hard like number two pencil erasers pointing straight down to the floor from her massive hanging tits.
I could clearly see the beginning of an outline of my fist already starting to show on her stomach. A feeling of sexual power and satisfaction came over me knowing I had just aroused my new stepmom by watching her shower and roughing her up.
It was obvious to both of us that she liked it. It was also obvious to both of us that I had a full blown erection straining to get out of my pants. Cathy just stared at my hard cock somewhat fearful, yet curious, of what I might do next.
I was pretty sure my dad had made Cathy aware of my sexual conquests, not only with multiple high school cheerleading squads, but also with a couple of my mature, married teachers and professors. I was also sure that my dad had made her aware of my reputation for being hung like a horse.
I could tell she was staring at my cock with curiosity wondering how much bigger I was than my dad. Being a 45-year-old stewardess I'm sure she had experienced a lot of cock in her life but I'm sure she'd never seen anything like the anaconda that was hanging between my legs and growing in my pants. I was so tempted to show her.
I felt quite proud and aroused wondering if she would dare tell my dad and show her bruised belly to him. Quite honestly the idea of my dad knowing I had roughed up his new wife while getting to feel her mature milkers, kind of turned me on.
When she regained her breath, I gave her a nasty stare and said to her,
"I think I know what you're doing here. You are trying to tempt me or maybe you are trying to seduce me? Is that what you're doing here Cathy? Are you trying to seduce me, or do you want me to take you into your bedroom and fuck you with the biggest cock you have ever had?"
I was young, bold and brazen, and I was ready to add my new step mom's pussy to my list of mature sexual conquests. There was something about this woman that made me want to punish her with cock.
I must've struck a nerve because she became awkwardly quiet and started to blush with her mature brown nipples now standing at full attention. She was obviously turned on by the whole situation.
I decided to take two steps towards her to intimidate her, and to see how she would react. She recoiled, took a step back and covered up her huge tits and her mature pussy with her towel. I pointed a finger at her, grabbed my crotch and said,
"Don't fuck with me again Cathy or next time it might be my cock up inside your belly instead of my fist."