Old Playboys

Warning: Mom and Son, Voyeurism.

Note: this story is based in reality up to the actual identity of the playmate which is fictional but the idea turned me on so much with conflicted feelings that I wanted to write this.

I didn't have many friends growing up. I actually really only had one and even that didn't last so long looking back. After the events which occurred, I was a fool and told my father to which his response was that I was never to see or communicate with my friend, Landon, outside of school ever again. I was 18 at the time I think, I remember because it was before I was 19, and fully discovered masturbation and all of the details involved with it. I grew up very sheltered and Catholic, private grade school and highschool. Mass every day but Saturday, praying and admitting to sins was a big deal.

My boyhood friend Landon lived with his mother, a short busty brunette and his father, a tall but not too bright auto mechanic. I grew up much more well off than they did but I was well bred enough to not humiliate them of this fact. I didn't see what I would gain either way so I took in their lifestyle with as little judgment as I could. Landon's father had a large tract of land on which there was a huge red barn, a small farm house, two garages, a home-made swamp, tire swings, tree houses, and about 20 acres of undeveloped land. The whole property was definitely out in "the country," which always intrigued me. I lived in a mansion basically, with my older sisters, mom and dad.

Dad was a very successful business owner, and mom was a homemaker and used to be a baker. I was the youngest of 4 children, all of my siblings were girls and they never did include me in anything fun, always teased me or locked me in the basement with spiderwebs. Looking back, I was starved for fun, anything, especially with another boy my age. I never had a tree house, pets, or lived on a dirt road. The way Landon lived seemed fun and vintage, sort of like how a town is without a McDonalds, Starbucks or Walmart in it. The kind of place you could still find a telephone booth or dirty magazines on the top rack of the news stand.

I liked Landon because he was very good at drawing. He was a quiet withdrawn kid like me, but I think he was special needs or at least had a speech problem. Either way I liked him because he didn't judge me and we hung out at recess together drawing bulldozers, earth movers and backhoes. When I was younger my dad pushed me to be a draftsman, before the days of AutoCad and other 3d imaging software. He said I had great promise and took my hobby and sucked all the fun out of it. I once showed him a drawing a bulldozer I had made with a ballpoint pen. I was really proud of it because it was accurate down to the rivets and bolts on the treads, every detail was accounted for. My dad was frustrated and told me to design it and label the dimensions, length, width, weight, etc. Simply a drawing didn't mean diddly squat, it had to be practical. I was crushed honestly.

Landon never used a ruler but his lines were clean and straight. I always had to have my ruler with me, I couldn't stand a crooked line on my art work. Landon was shorter than me, had dark brown hair which perpetually hung over his eyes. He had a strange habit of licking his palm and then flattening out the hair on his forehead. I'm guessing he didn't have a comb, the poor bastard. He kept his head down most of the time but he had a lot of freckles on his face and a slight limp. When he got excited there was a stutter, to which I was patient and waited for him to calm down and speak clearly. He told me his dad beat him when he stuttered, and his mom comforted him but both were frightened of the old man. He was heavy-handed with both of them, but was pleasant as punch when company was around.

When my friend gave me the grand tour of the farm and all the buildings he mumbled about his father's collection of vintage cars in the concrete basement of the barn. I didn't think he was into the cars but his dad loved that stuff so I think Landon also coveted the cars. Landon's dad was the kind of guy that would stop at every rummage sale and buy a blender just to scavenge one part for a project he never got around to finishing. You know the type. I really don't know shit about cars but the collection in there looked like it was bought fresh off the car lot in the 1970's and then magically transported to the basement. Red cars with huge tail fins and thick white leather seats, old school muscle cars with bold racing stripes, that sort of thing. There were some motorcycles and farm equipment too. Tons of odds and ends, junk of all sort made out of metal. My dad was a blue collar guy, he fixed our toilets and painted our white picket fence but he didn't collect junk like Landon's dad Donald did.

There was lots of junk honestly, shit that his dad tinkered with but then put back in it's place, copper pipes stacked up in the dust, repair manuals eaten by mice, old overalls with holes and grease stains hanging on a peg board rack. Upstairs in the barn proper were some old pinball machines. They were raunchy things with naked women riding Harley's on the cases and knobs. KISS the band, Medieval ladies wearing scraps of leather as bikinis, that was the level of class. Headbands and dark brown beer bottles were on a shelf high above near the ceiling. Next to the door that led outside there was a cracked red leather chair, couch and footstool. In the corner of the room was a big black safe that looked like it had never been opened. Gun magazines were stacked by the chairs, the room smelled of old cigarettes. Nothing had ever been cleaned. On the wall was a big framed picture of a stack of hundred dollar bills. That's the kind of thing Donald was excited about. The kind of guy that died wearing his highschool ring and still told about that amazing football catch he made 30 some years ago. A simple man with simple tastes.

In the main part of the barn were tons and tons of boxes of tools, broken washing machines, porcelain dolls, old lamps, old Hoover vacuums and on the upper level about a dozen milk crates full of old Playboys and Hustlers. In my house there wasn't anything close to this, the closest thing to smut was looking up the word Vagina in our Encyclopedia of Britannica; a pencil sketch of the vulva, very anatomical and scientific like, nothing to fantasize about. I never saw porn till Landon showed me his dad's collection in the barn that day!

At the time I felt pity for his dad, who probably spent a good deal of time in the barn, masturbating instead of screwing his wife. His wife's name was Eve. I didn't know much about her bbut she looked hot enough. She was about 5-2, brown eyes and brown hair that she had always dyed dark reddish purple. It always looked wet like she got out of the shower. Her right nostril had a stud in it and she had several tattoos, roses and angels. She was an old lady, a biker's wife back when Donald was younger and they were traveling a lot. Either way, Donald had vintage porn mags still in the plastic, others were stacked like a tower of pancakes on the floor, open to the elements, dust and spiderwebs had accumulated. Landon said I could look at any of them but don't rip the pages or make his dad suspicious. Looking back at it, he had to know his son would enter the barn and find that shit.

Maybe it was his passive aggressive way of doing sex education.I was a visiting friend of his son and I doubt he'd spank me like my father did for looking at hardcore magazines but all the same I respected Landon's wishes and said I would be gentle with the magazines. My friend grabbed a stack of magazines and went down the wooden stairs to sit in the red leather chair. I had an idea what he was doing but he made it clear I should stay up here and he would be down there, we were together in the barn experiencing the same erotic feelings and urges but not within seeing or hearing distance. Bro code shit. Looking back on it, he probably assumed I'd jack off up there and then wander down to him after he had stroked one out too, we'd go play with his chemistry set in the basement or something. He later showed me his father's pistol he kept in the nightstand in their bedroom.

It sounds ridiculous but I had never masturbated before. Hell, I didn't know there was such a thing; I grew up in such a sheltered home life. Two years later when I was 18 I finally jacked off sitting on my bathroom floor at home, buck naked, my back to the door in case someone tried to get in. I had heard touching my dick would feel good and it sure did and I kept doing it and then when I came I was really scared because I didn't know what semen was. I thought I broke my dick or something, seriously. It is a hard to remember everything, but I jacked off but didn't finish or didn't know there was an end...I would stroke it a bunch and it felt good and then I would just stop. I didn't know there was an "ending" to it all. At my private catholic school bathrooms there wasn't any graffiti, I'm telling you I was naive like Bambi in the woods.

When I reached for a magazine there was some massively-titted blonde on the cover, a finger in her mouth and long curly blonde hair cascading down her shoulders, perfectly drawing attention to her huge torpedo-shaped boobs. My heart was pounding as I gently opened the front cover, mesmerized at the smut before me.

Do you remember the old Playboys and Hustlers, 1960's, 70's, that era? Torpedo boobs were in style, pointy white bras, full bushes, and articles and interviews mixed in between the models and playmate photo spreads. Folded pages you could pull out and see Miss March or February spreading their legs or sucking on a thick cock, immensely enjoying themselves.

I remember reading about Huge Hefner and his smoking jacket, how he invented his "style," and the Marlboro smoking ads interlaced in the mags. My dick really was hard but at the time I was flipping through the magazine, amazed that women would display themselves so explicitly. The Hustlers were hardcore, they made the Playboy magazines look lame. Hustler girls spread their pussies with their fingers, were doing blowjobs and had ropes of cum on their boobs, perfectly formed asses, round full juicy boobs... you couldn't ask for better tits!

I removed my red flannel button down shirt and placed it under my bare ass as I pulled down my pants and sat on the wooden floor, getting ready for a good wanking session.

When I saw the lady on the cover I knew that this was the real deal, the kind of shit the kids were always talking about, a real deal Playboy magazine. I don't know if I can convey it but the idea of having a Playboy magazine in your possession as a young man was pretty much like having a solid gold bar. You wouldn't dare share it with your buddies because you knew someone would tattle and it would get taken away, shredded or burned. Parents wouldn't simply thrown in the trash, you'd be digging through rotten banana peels and soiled tissues like a rabid raccoon to find that motherfucker, wipe it clean and hide it in your room as best you could like a prisoner hiding a homemade shiv.

I put down the magazine I was flipping through, feeling like blondes were my thing, not ebony ladies or brunettes, but young curvy blondes with big round boobs. I felt like this was my thing, something I liked, I was unique. The next magazine I picked up in my 16 year old hands had my type of lady on the cover, she was pale skinned, medium height, thick curly blonde hair past her shoulders, and was wearing a type of night gown that was nearly see through. She had very respectable tits, sort of small but round with hard dark nipples. She was on her knees, hands on her thighs, slightly spreading her legs.

You could clearly see she had a very hairy pubic region, but trimmed into a wide landing strip. I remember committing to the act that I would touch myself and get excited like the older boys in the locker room talked about, stroking their penises to hardcore pornography and here I was doing the same thing, feeling like a man now. I have a decent sized penis, about 6 inches long, and I had girth, nearly as thick as my wrist. Again in my innocence, I didn't know if I was big or small but judging by the other men in the magazines pleasing these harlots I was average, if not a little bigger which of course felt good to my ego.

Opening to the first page my heart stopped for a second. It was my mother! I knew it was from about 25 years previous, but it was her! The first page had her leaning against a barn door in some coveralls, one strap off her shoulder and a large side boob was clearly seen, the dark nipple rock hard. I couldn't believe this, it couldn't be her or could it? I knew my mom Kathleen was born in the 1950's so this 1980's Playboy could be her, the time frame was possible. Kathleen now was a thick blonde with grey roots, thick thighs and strong forearms. MILF wasn't really how I would describe her, she was a bit too blue collar, too matter of a fact woman. In the past she said she was a baker and later met my father and became a stay at home mom. Where did she find time to pose for pornography? Maybe like the other sluts to pay for college like those stupid little interviews said?

To further solidify the fact it was my mother, she wore two gold chains. One had a small cross on it and the other a diamond. My mom told me years ago my father couldn't afford the ring, only the stone so he had it made into a necklace. The cross came down to the tops of her breasts, a gift from her very religious grandmother who I had never met. The diamond chain hung deep between her breasts, almost parallel to her nipples. My left hand was wrapped around my hard cock and my left was turning the page to see what else she would expose to the camera. Her dark round areolas were perfectly centered on her boobs, almost like an anatomical chart in a textbook about reproduction. The nipples were darker, small but firm stubs. I wondered what nipples tasted like.

The second page was a fold out, in this scene she was sitting on a milking stool, top fully off and her huge round boobs on full display. Her legs were spread wide apart, one hand on each knee as if there was significant heat venting from her vagina. Those breasts were amazing, so round and full, a full F cup. I was rubbing my dick quickly now, my hips moving slightly forward imagining fucking a pussy. In and out, slowly, in and out. I dropped the magazine to have my other hand cup my balls, teasing them making my dick super hard. I could feel the heartbeat pulse in my dick, the blood pumping hard. I let out a low groan and picked the magazine up again.

The third page almost made me ejaculate, there she was sucking on a very large penis. The man was on one side of a horse stall, his dick through a hole and his head visible over the top. My mom was on her knees in the straw, fully nude, taking it in her mouth, a tight fit too! Her long blonde hair was behind her neck, and her eyes were closed, intently pleasing the stranger. I couldn't see her vagina but from the side I saw the heft of her boobs hanging just slightly, large dark areolas and standing nipples. I imagined her pussy to be like the woman on the cover of the magazine, a wide thick dark landing strip of hair, some wetness around her inner labia lips.

Ready to take that thick rod inside of her, easily sliding in and out, slowly, in and out. The sight of my conservative catholic mom sucking on a huge cock, not my fathers, made me angry that I was so aroused at it but also super horny because she was hot as balls and I was straight so this would turn any dude on! How could I not be excited by this big titted slut on her knees, nude in a barn blowing big dong? Had they shot other scenes together? Had he put his penis inside of her vagina? Did he finish inside? Did she swallow his seed? My cock was getting red from all the vigorous stroking and I needed to release.

Page 4 had her bent over the milking stood, grabbing the seat with both hands and the man off to the left had his penis in his hand, firmly grasped and ready to stick it inside her wet box. Her ass was pointed straight at the camera and with her cheeks spread just a bit I saw her dark slit, the vagina and her asshole. Both were covered in a tangled mat of hair, darker than her blonde hair but not super dark either. The man had one leg on the stool and it provided a good angle of this cock and balls, dressed with dark pubic hair but trimmed a bit. His neck and face were red, excited at the prospect of sticking his penis inside her. His face was very average, with a mustache and beard, sort of a sailor type with faded tattoos on his forearms, some barbed wire on his left hand which was on my mom's butt to steady himself and on his right a dark raven on the back of his hand. Besides the ink he could pass for any generic pornstar guy from the 1980's.

The next several pages were torn out! Son of a bitch I wanted to see my mom take his hefty rod in her snatch! I examined the binding and counted at least 4 pages that were gone. Flipping quickly through the last pages it was just ads and a virgina slims ad with a tall but rail thin brunette. She was fully clothed, not like the whores inside the magazine, my mom excluded of course. It suddenly dawned on me that Donald had to have seen these pages and torn them out. Maybe he was blackmailing my mother? I tried to remember if they had ever met. My father had shook Donald's hand when I first started coming to the farm, he introduced himself while mom and me stayed in the Ford Bronco.

I imagined the pages folded up inside his wallet or in bible on the bedroom nightstand, a perverse way to own my mother. Did the mustache man fuck my mother? Of course he had to, this was a porno mag that's what they did. I was hovering close to cumming. How many times did he shoot his cum thinking of my mom taking that cock? Probably a lot of times if he had taken to ripping out the pages. I continued stroking my penis, imagining a very taboo scenario of Donald fucking my mom's tight pussy, ramming himself over and over inside of her. In my mind she was in some pain, struggling to take his thickness and rapid pace but also enjoying it, building towards an orgasm.

I fantasied about how she came to be in the magazine. 21 year old Kathleen Bartowski had done the scene just to make 500 dollars, to pay for textbooks. If she was lucky there would be some money left over to buy matching promise rings for her and her boyfriend, Tony. They were in love and waiting for marriage before fully giving themselves to each other, it would be so special! He was such a good-hearted catholic loving man. It was supposed to be a calendar girl shoot, no men and no bottomless nudity. Kathleen was okay letting the world's men see her hooters, but not below the belt.

That was special, for Tony and only for Tony. She was told to "shut up and smile" so she did, undressing for the camera and the several men behind the tripod, a tall dark-skinned one smoking and the other seated on a chair, his pants around his ankles, stroking his large member. That was the director, the man who promised it would be a girl-girl photoshoot, some bikinis and boobs, nothing that she would be uncomfortable with. And now here she was giving away her V card to this hairy garlic-smelling brute who was pounding on her virgin pussy. It was very sore already, she wished he would finish so she could go home and shower. Church was tomorrow and she would see her boyfriend again, Kathleen loved him so much.

He would never ever know about this. She had used a fake name with the director, called herself Cathie Cummings. Obviously he knew it was fake but the sleazy director only wanted to be the first to see her take it on camera, this young and well-gifted busty blonde. She was so uptight, he knew she was a closet slut, sucking off her boyfriend one day and then kneeling and praying for forgiveness the next. After Harry was done with her he would take what every man owns, that pussy. It was already broke in real good and would still be wet, he would just slide up from behind as she was in the shower and give her a nice bonus. The director was stroking his large penis, hand up to the glans head and then slamming it down to his balls, feeling them jiggle. Harry sure was fucking this bitch good, she took it with only a few whimpers. Those huge tits needed to be shared with the world. So selfish of her to think she "belonged" to her boyfriend. Right now this whore belonged to him, he owned that pussy and she would do as she was told.