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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 naïve, 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."
I just turned around and walked out. She said nothing.
Immediately a nasty feeling of power was coming over me that I had never experienced before. I felt empowered by my arrogance of not only standing and watching my naked vulnerable stepmom, but also punching her in the stomach, feeling her mature tits and tempting her with huge teenage cock.
Even though she was my stepmom, I immediately had the desire to punish my damsel in distress again right then and there. Looking back, I believe that might've been the first time I made the connection between True Detective magazine and bondage and punishment. That moment would change me forever.
Later that night at dinner, my stepmom started to stir things up and tried to start a conversation by making a comment to my dad.
Cathy got my dad involved by saying to him,
"Well honey, your son Jimmy sure got an eyeful today. Would you like to tell your dad about it Jimmy?"
Before I could answer my dad jumped in,
"Oh really Jimmy, tell me about it."
I stuttered and laughed and replied,
"Well dad, I accidentally saw Cathy getting out of the shower today."
My dad immediately challenged me, since he knew about my obsession for mature women. He said,
" Son, did you accidentally see her or did you make it a point to spy on her? We all know your reputation for liking mature women, and Cathy is a trophy."
My dad half smiled and looked at my stepmom. I knew he was not done with his questioning yet and he wanted to embarrass and mess with the both of us a little longer. I was going to put an end to his questioning right away, so I arrogantly responded,
"Well dad, I sure got a great look at Cathy's huge hanging tits and nipples. I also got a good look at her firm ass and especially her hairy red heart shaped pussy watching her dry herself off."
I didn't dare say anything to him about punching her in the stomach or how much I enjoyed the feel of his new wife's tits and teasing her with my cock. I wanted to see if she had the guts to bring it up. She said nothing.
I think both of them were stunned by my direct honesty. I then decided to embarrass my stepmom by putting her on the spot by continuing talking to my dad,
"And Dad, the most amazing part about the whole thing was Cathy purposely dropped her towel, put her hands on her hips exposing her naked body to me and just asked me if there was something I wanted to talk to her about."
Then to make it worse, I asked my stepmom, "Cathy, I was amazed that you didn't try to cover up your body. Why did you make me walk over to you, pick up your towel and hand it to? You just let me stand there and look you over from head to toe?"
I then asked her a question that really shook her up and got my dad's full attention,
"By the way Cathy, do your nipples always get that hard when you shower?"
Well, my dad looked at Cathy in amazement waiting for an answer. I'm sure he was curious what she would say about her hard nipples. It was obvious to all three of us that she was turned on by the shower incident. I was starting to get hard again waiting for her answer. I'm sure my dad was also getting turned on over the whole situation. Cathy had nothing to say.
My dad finally broke up the tension by saying,
"Well son, you're a handsome young man. Get used to it because you'll be seeing a lot of naked women in your lifetime."
I honestly wasn't quite sure if my dad was subtly giving me a free pass to check out my naked stepmom anytime I wanted. I interpreted it as a definite yes and for many years after that I took every liberty to blatantly walk in on my new stepmom to catch her in some awkward situations.
I even walked in on her once while she was masturbating and I got some nice screenshots and a short video of her screaming to climax on a big fat black dildo. I figured I could use it as leverage against her if I ever needed it.
I was always tempted to show the screenshots and video to my dad but I wasn't sure how he would react. It was also too much fun messing around with Cathy and I did not want to ruin a good thing. I did however share them with my good friends multiple times, and we all blew our loads watching Cathy bring her self to a shattering climax while stretching her mature pussy with the oversized black dildo.
I also did not understand why my stepmom didn't mention anything to my dad about me clearly punching her in the stomach and feeling her tits. I know she took my threat seriously. Even though I was a bit confused I did learn many things that night about my parents and also about myself.
I listened to my dad relentlessly punish fuck Cathy for hours later that night while I listened through my bedroom wall. For years, I had enjoyed listening to my dad fuck the hell out of my real mom, and now I was enjoying listening to him fuck my new stepmom. They were both obviously turned on by what took place between me and Cathy earlier in the day.
Listening to them through the wall that night I realized for the first time that my stepmom and dad might be into bondage and rough sex. It was pretty obvious by the sounds of her muffled screams and the sound of a leather belt slapping across her ass that they were into some kinky stuff.
I realized that I was totally turned on listening to Cathy's muffled cries and screams as my dad aggressively strapped her. One more thing I realized was that my new stepmom's tits, ass and pussy would be the gold standard for me for the rest of my life.
Now let's circle back and discuss the effect that True Detective and bondage magazines had on me and my friends.
I remember the first time I saw the cover of a True Detective magazine like it was yesterday. I was 18 years old trying to buy a Playboy in a liquor store when I noticed a copy of True Detective.
The cover pictured a mature woman, probably in her 30's or 40's, sitting in a chair with her arms pulled back and tied behind the back of the chair. Her nipples were noticeable as her tits strained against her blouse. Her ankles and knees were also tied together with rope and her skirt riding up, showing the tops of her thigh high nylons and garter belts. Her sexy legs were accentuated with an equally sexy pair of high heels. She had a gag in her mouth, and a terrified look on her face.
Her blouse had been sliced open exposing her black lace push up bra holding her large vulnerable tits. There was a small trail of blood trickling down one of her tits where it had been slightly grazed by a knife held by an evil masked man standing behind her. He obviously had intentions to do whatever he wanted with this lovely mature woman. Even though I was only 18 I was totally aroused and I immediately knew I had to see more of this.
I shared the True Detective magazines with my buddies, and we all realized we had a passion for mature damsels in distress. The mature women we picked up at the beach also inspired us with their wishes to be bound and gagged, used and abused and then eventually hard fucked.
I also suspected that my parents were also involved in bondage from the night I heard my dad punish fucking Cathy the day she flaunted herself to me after her shower. From the sounds of her muffled moans and screams I could tell she was definitely gagged while being strapped and basically molested by my dad.
Out of curiosity one day, I decided to go through their bedroom closet and dresser drawers when they were out shopping. To my surprise, I found a pot of gold.
Hidden in a box in their closet were some copies of Playboy, Hustler and copies of the nastiest editions of True Detective. There were also a couple hard core bondage magazines featuring mature women as damsels in distress.
To my pleasant surprise, I also found a couple photos of my real mom and also my new stepmom Cathy both on their knees bound and gagged. Apparently one of my dad's requirements for a wife was that they needed to be into bondage.
In the photos both my real mom and of my new stepmom were surrounded by a small group of men with rock hard cocks inches away from their pretty faces. It appeared that they were all waiting to have their cocks sucked off. I figured there had to be more.
I decided to go through the dresser drawers and made another amazing discovery. In addition to finding multiple pairs of my stepmom's regular underwear and bras there was also a separate drawer of crotchless panties and bras with holes for Cathy's nipples. I also found a variety of ropes, nipple clamps, ball gags, blindfolds, and a string of what I would later find out to be, plastic anal balls. I also found Cathy's fat, big black cock dildo that I had seen stuffed up her heart shaped pussy.
I carefully put everything back the way I had found it before my parents got home. However, I could not resist taking one copy of True Detective magazine, and a couple pictures of both my bound and gagged mothers back to my room to jack off to later that night and to share with my friends.
My curiosity had been peaked about my dad and Cathy's involvement in bondage. My next mission was to catch my stepmom and dad in the act and confirm that they were actually into bondage. I set up a plan.
I had my next door friend Tommy invite me over one night for a sleepover. That way I could sneak back over to my house and check on my parents thinking I was gone for the night. I always enjoyed staying at Tommy's house because his stepmother Gloria would always come out in her skimpy bikinis and join us boys in the hot tub.
Gloria was a stone cold Columbian milf in her mid 40's with magnificent tits, thick botox lips, and a feisty prick teasing personality. Tommy's dad Stan would never join us in the hot tub but he would sit in a lawnchair with a cocktail in his hand and listen and laugh at us horny 18 year old teenage boys trying to convince his wife to show us her tits. I always thought that was kind of weird however it was worth it to have the chance to be in the hot tub with Gloria and try to talk her out of her bikini.
On one occasion Tommy and his dad went back into the house to get some more drinks leaving Gloria alone with me in the hot tub. Gloria was getting drunk on wine so I took the opportunity to ask her to show me her tits without Stan and Tommy being around. She looked around making sure the coast was clear, pulled down her bikini top and gave me a quick peek at her magnificent tits with large, silver dollar size nipples.
I jokingly told her it would be alright if she wanted to reach up inside my swimsuit never thinking she would do it. Well I was wrong. Gloria put her tits back in her bikini top, and aggressively reached up my swimsuit and wrapped her hand around my growing throbbing cock just as Tommy and his dad slid open the patio door carrying some beers and another glass of wine for Gloria.
The jets on the hot tub were on full blast creating a camouflage layer of bubbles on the surface. Gloria did not consider stopping for even one second. She kept her hand wrapped around my stiff cock circling her thumb around the head of my cock trying to make me cum.
It didn't take long before I blew my load in the palm of her hand inside my swimsuit. Tommy and his dad were sitting right there and they had no idea what was going on under the the water. I had to bite my lip and take a sip of my beer to hide the fact that Tommy's slut milf stepmom and Stan's prick teasing wife was shamelessly jerking me off right under their noses.
I tried my best not to show any emotion as I blew my load in Gloria's hand. When I had fully unloaded, Gloria just smiled at me, let the hot tub water rinse off her hand and reached for her fresh glass of wine. I knew right then and there that Gloria and her husband were definitely kinky and may have also been in to the whole bondage kink.
After Tommy's parents went to bed that night I snuck back over to my house and noticed that one of my dad's friends Roger had his car parked in our driveway. I could tell from outside the house that the only light on inside the house was coming from my stepmom and dad's bedroom.
I quietly snuck in through the basement door as I usually did, took off my shoes and gently crept down the hallway towards the bedroom light. Since everyone assumed I was gone for the night, they had left the bedroom door wide open. As I quietly crept towards the bedroom, I could clearly hear the sound of a leather belt, smacking in the palm of someone's hand and Cathy's voice crying and weeping out loud, begging for mercy.
I could hear my stepmother pleading,
"Oh my God, please don't do this to me Roger. I promise we will not say anything to anybody about this. We will tell you where we keep our money. You can take everything you want from the house just please don't hurt me."
My dad was also pleading with Roger,
"Come on man, leave my wife alone. You don't need do this to her. I'll give you anything you want. You can use her all you want tonight, just please don't hurt her."
The masked man did not appear to show any emotion while he kept tying my stepmom to the foot of the bed with a leather belt laying at her feet.
I hid in the total darkness of the bedroom across the hallway and watched the whole scene unfold.
It appeared that my stepmom and dad had hired Roger to act out a home invasion role play. Roger was Cathy's ex husband and was more than willing to get some role play revenge on his former wife. Very kinky indeed.
My dad was bound and tied to a chair, still wearing his work suit struggling as if he was trying to get away. Roger was dressed in all black with a bank robber type stocking face mask over his head. I shifted my position anxiously waiting to watch my new prick teasing stepmon get roughed up by her nasty ex husband. I could not believe what I saw.
My stepmom was wearing her full stewardess outfit, including her cute little hat and high heels. She was standing and tied to the brass footboard at the foot of the bed. Her arms were spread wide and her wrists were tied to the top rail of the footboard. Likewise her ankles were tied to the base of the footboard with her legs spread as wide as her tight stewardess skirt would allow. She was not gagged. Roger and my dad wanted to be able to hear every one of her moans and cries for mercy.
Roger gave my stepmom's tits a hard squeeze through her blouse and groped her pussy through her skirt before he walked over to the dresser and picked up a nasty looking knife. My cock immediately started to spring to life as my dad continued to struggle. My dad was not gagged, and he was pleading with Roger to not hurt her.
Dad said, "Please don't hurt her Roger. Please, I beg you please don't hurt her. She will never be the same." Roger walked over to my father and held the knife right up to his face.
Roger replied, "Shut up you fucking pussy. Goddamn right she'll never be the same. Let's see what your new big tit stewardess wife thinks about it."
Roger walked over to my trembling stepmom and put the dull side of the cold steel knife blade up against her right cheek and slowly pulled the entire length of the blade across her cheek. He switched hands and did same thing with the knife to her left cheek as my stepmom moaned and shrieked.
I was beginning to wonder if this was still role play or the real thing because my stepmom looked terrified. I had overheard my dad mention more than once that Cathy's ex-husband was a bit of a nutcase and had been arrested a couple times for slapping her around. That made it all the more arousing not knowing what he might do with his sexy ex-wife who now defenseless and tied to the bed. Things were just getting started.
Roger walked over to the dresser and took a full swig out of a bottle of Jack Daniels whiskey, and set it back down on the dresser. He walked over and bitch slapped my dad and then once again turned his full attention on his ex wife Cathy.
He started his torment of her by putting the sharp edge of the blade under the hem of her skirt and started slicing the skirt upward bringing the knife straight up between her thighs towards her pussy.
I could see her legs tremble as he pulled the blade up between her inner thighs. He took a few steps back and set the knife back on the dresser. He took another full swig of whiskey, set it back down and slowly walked towards my new stepmom to continue to torment her.
He grabbed both sides of her wide open skirt and finished by ripping her stewardess skirt up to the waistband eventually ripping it off entirely and throwing it towards my dad to taunt him. I could clearly see my stepmom's legs shaking and trembling from fear and sexual anticipation.
My stepmom now looked like a classic damsel in distress. She was standing tied to the bed, wearing her high heels and thigh high nylons. Her uniform hat still perched on her head and her work blouse draped down covering her panties.
My recently discovered interest in bondage clearly started to kick in and I started to rub my cock through my pants. I was almost trembling with anticipation to see what my stepmom's ex husband was going to do to her next.
Roger then got down on one knee to get a closer look at Cathy's inner thighs, panties and trimmed pussy. Obviously Roger was very familiar with his ex wife's inner thighs and pussy having been married to her for years. Roger looked over at my father, and then looked up at my at his ex-wife and rhetorically asked,
"Oh my my, what do we have here?"
I could clearly see why Roger was surprised. My stepmom was wearing a pair of her orange crotchless panties that I had found in her dresser drawer. With both hands, Roger felt the smoothness of my stepmom's inner thighs before using the index finger and middle finger of his right hand to slowly spread her pussy lips apart.
My stepmother shrieked and threw her head back as if she was somewhat embarrassed by the crudeness of her crotchless panties.
My dad boldly stated,
"Roger, you fucking bastard, Leave her alone. You already had your chance to fuck her pussy for years. Her pussy is for me now and me only."
Roger continued to finger my stepmom's pussy and looked over and stared at my dad.
Roger defiantly responded, "Not anymore motherfucker. Your wife's pussy is going to meet an old friend tonight and you have a front row seat to watch."
Roger then proceeded to slowly bury his middle finger up to the knuckle in my stepmom's red haired covered pussy. She shook her head back and forth and yelped as Roger joyfully wiggled two of his short fat fingers up inside his ex wife's pussy.
Roger pulled his fingers out of her snatch, got up from his knees and walked over to my dad. Roger held his fingers up to my dad's face, so dad could clearly see that they were glistening and covered with Cathy's pussy juice. She was turned on. Roger put his finger under his own nose and took a long whiff before wiping off my stepmom's pussy juice across my dad's nostrils. Roger continued to taunt my dad with trash talk about his ex wife,
"You know what motherfucker, two things I really liked about my ex-wife was the way she squealed when I clamped her nipples to punish her, and I've always loved the smell of her pussy. I bet you also love the smell of your wife's pussy?"
Roger continued,
" Do you know what her pussy smells like to me right now motherfucker? That's the smell of an excited mature pussy that needs to be fucked more often than you're fucking her. I think I can help you with that."
Roger had another shot of whiskey from the bottle on the dresser before he returned his attention to my stepmom damsel in distress. My stewardess stepmom was about to lose the rest of her clothes and I was mesmerized and had a front row seat just like my dad.
Roger starting to pick up the knife, but then changed his mind. He approached my bound and gagged stepmother, grabbed both sides of her stewardess blouse up by her neck and violently ripped it wide-open. White pearl buttons were flying everywhere and I could hear them rolling across the hardwood bedroom floor.
I could tell my dad was still playing his role but was getting aroused and so was I. My stepmother thrashed her head from side to side and shrieked as her attacker opened up her blouse and pulled it off her shoulders.
To my delight my stepmom was wearing the orange bra with the nipple holes that matched her panties. Roger retrieved his knife and started flicking her protruding nipples with the dull side of the blade bringing them to full attention. Her nipples looked just as they did when I confronted her and abused her after her shower.
Roger laughed as he slid the blade under her bra between the cups and with one upward slice cut her bra in half. Her bra snapped back and her jiggling tits sprang free on full display.
At that point my dad was finished playing his role as the helpless husband. He easily worked his hands out of his ropes and threw them on the ground. Apparently he was upset that his new wife was sexually aroused and was enjoying her role as the victim way too much.
My dad picked up the bottle of Jack Daniels and took two serious gulps of whiskey straight from the bottle before setting it back down on the dresser. He wanted to get a buzz going before he joined Roger in tormenting Cathy.
Roger stepped aside as my dad approached my stepmother with an ominous look on his face and an obvious erection in his pants
Dad started to verbally abuse Cathy by saying,
"You fucking cunt. I think you're enjoying this way too much just as you did with our son in the shower the other day."
He looked into her eyes and told Roger to bring him the nipple clamps laying on the dresser.
One at a time, my dad pinched open the clamps and hung them on Cathy's eraser hard nipples. Roger was once again enjoying the sound of his ex wife's screams as my dad lifted her tits off her chest with the nipple clamp chain. My cock was throbbing. The more she moaned and screamed, the harder I got.
My dad pulled her nipples and tits up towards her chin and held them there until she shrieked and whimpered as tears started flowing down her cheeks. The more she cried, the harder I started rubbing my cock through my pants. It totally turned me on watching my dad's new milf wife get tormented. My dad let go of the chain and her tits bounced as they fell back to her chest.
He then he did something I never expected. My dad clenched his fist, pulled back his right arm and punched her right in the gut just as I had done to her. Apparently like father like son.
She gasped and doubled over at the waist trying to catch her breath just as she had done with me. Her blouse and bra were hanging off her shoulders as her big tits swayed and jiggled as she gasped for air. I suddenly realized I was becoming a fan, not only of bondage but also BDSM.
Roger and my dad untied her and took her over to the bed while she was still wearing her crotchless panties, nylons, high heels and her cute little stewardess hat and of course the nipple clamps. They laid her on her back and tied her arms over her head to the headboard.
My dad grabbed Cathy's high-heeled ankles and spread her legs wide so Roger could have the honor ripping off her crotchless panties as a souvenir. Roger pulled off his ski mask and threw it in the corner of the room. He wanted to the ex-wife to remember his face as he continued to torment her.
Roger used both hands, placing his fingers in the opening of her nasty orange panties and aggressively ripped them off. There's nothing quite like the sound of a woman's lace panties being ripped from her body.
He swung her panties over his head in celebration before shoving them in his pocket. Her shrieking and whimpering was getting everyone excited including me. I realized right then that I was not only a fan of bondage, but was becoming a fan of BDSM.
Roger and my dad were going to give my new stepmom a little more well deserved punishment. They flipped her over on her stomach as my dad picked up the belt off the floor.
He doubled up the belt, rubbed his hand over my stepmom's smooth ass then raised the belt over his head and slammed it down on both of her mature ass cheeks. She screamed out loud as he raised the belt up behind his head again and let her quivering ass cheeks experience the belt one more time. As tears continued to roll down her cheeks, my dad handed the belt to Roger and told him,
"Let her have it and don't hold back."
Roger was more than anxious for the opportunity to punish and abuse his ex wife. He was more than familiar with strapping Cathy's ass. Roger rubbed one hand over her his ex wife's ass remembering how soft it felt and to feel the welts that were starting to form. He bent over and kissed her ass, soaking in the familiar aroma of her ass and pussy before raising the belt up behind his head and slamming it down hard on his ex wife's ass cheeks. Once again she screamed out loud knowing that no one else was in the house. My dad told Roger to do it one more time and Roger obeyed.
At that point my stepmom was laying on her stomach with her hands tied over her head to the headboard, still wearing her nylons, high heels and her stewardess hat and nipple clamps. It was obvious she was turned on and wanted some cock.
My nasty kinky dad wanted to watch his new wife take some revenge fucking by her ex husband and Roger wanted to give it to her. My dad intended to have her suck his cock while he watched her ex husband fuck both her ass and her pussy.
My dad untied her hands from the headboard so Roger could pull her up on her knees. As Roger took his position behind her, my dad took his position sitting on the bed, leaning back against the headboard with his hard cock pointing straight out of his pants waiting for Cathy's soft botox lips.
Both Roger and my dad had agreed they were going to spit roast my new stepmother, my dad's new wife, and Roger's ex wife all in one. Cathy was up on her knees with both her mature ass and pussy up for grabs.
Roger slowly rubbed the head of his cock over his ex-wife's glistening wet pussy lips and worked his cock into her all to familiar pussy. He knew full well from experience that she had always struggled take him balls deep in her mature pussy. Tonight was no different. He was taking her balls deep and she felt every inch screaming like a true damsel in distress.
At the same time, my dad put both hands behind Cathy's head, grabbed her hair and shoved her face down on his cock. He was using her face to get his cock fully erect before pushing it in her mouth and down her throat.
Roger and my dad worked her over for what must've been a half hour with Roger alternating stuffing his cock in his ex wife's pussy and asshole. Both men were ready to blow their loads. Roger got up on his feet on the bed, grunted and growled as he dumped his load in his ex wife's ass. My dad held her head down on his cock and would not let her head up as he blew his load down her throat. She choked and gagged with my dad's jizz flowing out of the corners of her mouth
Roger wanted more. He immediately buried his face between her soft ass cheeks that were still red with welts from her earlier strapping. Roger loved the smell of mature ass, and the taste of mature pussy juices. He shoved his nose up my stepmom's ass hole and his tongue was clearly up her pussy. My stepmom gasped and moaned in total abanbonment pleasure.
Roger went after my stepmom like he hadn't eaten pussy for a month with my dad giving him encouragement all the way,
"Come on Roger, eat that red haired pussy. Make her squeal and squirt. I want to fuck the bitch after she squirts." Cathy appeared to be enjoying the dirty talk as both men continued to plunder her.
My dad stood there jerking his cock watching Roger orally destroy both her asshole and her pussy. My stepmom was flopping on the bed like a trout laying on a dock squealing, twitching, and moaning at Roger's oral assualt.
Roger decide to finish her off by flipping her over on her back, spreading her pussy lips and sucking on her swollen clit while tugging on the nipple clamp chain. All this was too much for her which caused her to explode pussy juices, almost as if she was pissing the bed.
I lost count how many screaming orgasms my horny damsel stepmom had while Roger lapped her pussy like a dog. When he was finished, he traded places with my dad. My dad pulled out his cock, still wearing his suit pants and laid down between Cathy's thighs. Roger held her ankles and spread her as wide as she could go. My dad immediately went after her in a four point push up position and hammered her relentlessly with her screaming and yelling.
Finally, in unison, my dad blew another load in my stepmom's pussy as Roger straddled her face and dumped his second load on her face covering her from her forehead to her chin. Roger then got dressed and left and I laid low until I knew my parents were fast asleep. I then returned to Tommy's house.
The next morning, Tommy wanted to hear everything about my experience with my parents. I told Tommy everything that happened from the incident with my stepmom in the shower to what happened with her and my dad and Roger. I also told him about the magazines i had found in the closet and also about the pictures of my mom and stepmom bound and gagged. Tommy was surprised, and then said,
"Jimmy, come with me to my bedrooom, I've got something I want to show you."
Tommy pulled a box out from under his bed very similar to the one I found in my parent's bedroom. He pulled out multiple copies of True Detective magazine, copies of Hustler and Penthouse. To my surprise, he also had some bondage photos of his stepmom Gloria in positions similar to the photos of my mom and stepmom. Gloria's hand job in the hot tub was starting to make more sense to me now. It appeared that our parents had something in common. Bondage and BDSM.
Tommy and I started to wonder that if all our parents were into bondage. We wondered if our other buddies had similar experiences with their parents. We called Brian and Richard to meet them at each of their houses. We figured if they had magazines and photos of their parents similar to ours they wouldn't want to risk trying to sneak them out of their house. We met at both of their houses, and our suspicions were confirmed.
As we suspected both Brian and Richard had True Detective magazines similar to what our parents had as part of their sexual stash. More importantly, they also had compromising photos of their dads tying up the moms in various positions. In addition to the copies of True Detective there were a couple of other things that all of the the photos of our moms had in common.
In addition to our dads, there was always another person involved to help assist with the bondage and to join in punishing the women with whips or leather straps, as was the case with my stepmom. But best of all there was always a third person there to take part in the sexual use and satisfaction of our moms and stepmoms.
Although their faces were never clearly shown in the photos it became obvious to all of us that it was our dads who were involved as the third person in the photos. It became very clear that our parents were involved in some type of couples swingers group involving bondage and BDSM.
I encouraged my buddies to search through their parents's dresser drawers. They all made the same discoveries that I had. Sexy, nasty underwear for our moms and stepmoms and a variety of bondage and sex toys to enhance the sexual experience.
All four of us were now well over the age of 18 and we were still obsessed with True Detective and the idea of mature women bound and gagged. We all had great sexual relationships with our girlfriends, but there was just something more erotic about the sights, sounds, the feel and the aroma of a mature woman, bound and gagged and on the edge with fear of being abused. The idea of taking it one step further to experience our mature moms was always on our minds. But how on earth could we pull that off?
We considered a couple different ideas that would allow us to anonymously subdue our moms and stepmoms, bound and gag them, rough them up and maybe even sexually abuse them.
We discussed the idea of tag teaming them with our dads, or getting involved in their bondage and BDSM group but neither of those ideas would give us the flexibility to do what we wanted to the women. We finally decided to carry out our well planned scheme on Halloween when we knew all of our dads would be out of town together on a hunting trip.
All four of us bought Halloween costumes with various scary movie characters that would make it impossible to identify who we were and also terrify the woman. We knew that my mom and Gloria next door were handing out candy together and the other two moms were doing the same thing at Richard's house.
We would all go together as a group so that we could work in pairs on each woman to subdue them, strip them, and bound and gag them. Once we had them totally under our control would then decide what type of BDSM we wanted to do to torment each other's milf moms.
We decided go after Brian and Richard's moms first and then finish up with my stepmom Cathy and Tommy's stepmom Gloria. We would make them think that the home invaders were members of their bondage and BDSM group. They would never suspect it was their own nasty sons and stepsons.
They would all be stripped, bound and gagged and blindfolded. There would be no talking among the four of us so that our voices could not be recognized. We will leave our costume masks on at all time. Our mom damsels would have no idea what hit them.
We arrived at Richards house at about 8 o'clock and waited until no other trick or treaters were around. Both moms greeted us at the door wearing their costumes and holding bowls of candy. We bullrushed the door, punched them both in the stomach knocking the air out of them keeping them from screaming.
They both dropped their bowls of candy and dropped to their knees gasping to catch their breath. The porch light was turned off and they were immediately gagged and dragged to the back of the house.
We earlier agreed that punching the women in their soft mature bellies was going to be our signature move not only because it felt great, but also because it immediately shut the women up, so they couldn't scream.
Brian and I went after his big tit mom dressed as Elvira and Tommy and Richard went after Richard's mom dressed in a very sexy, I Dream of Jeannie costume. We could already see their bellies start to bruise from our punches.
We decided to leave them in their costumes for now, so that we could focus on blindfolding, gagging and tying them up. After we had their blindfolds and gags secured we tied their wrists behind their back, and ankles and knees together to keep from kicking us. True Detective magazine would've been proud of our handiwork. These two mature milfs were not going anywhere.
Once we had the women bound, ripping off their costumes was pure joy. We rolled Elvira on her back and her costume was ripped wide-open from the front. She was wearing a black lace bra and very sheer black lace panties that clearly showed her shaved pussy lips. Brian ripped off his mom's bra. Her mature tits with large full nipples were gyrating as she struggled on the floor.
This was the first time Brian had ever seen his mother totally naked and vulnerable and he was having trouble controlling himself. Brian's mom looked great bound and gagged and blindfolded wearing only panties, thigh high nylons and high heeled shoes. Brian was having a field day with his mom tits, grabbing, squeezing, sucking, and slapping her big mature titties.
Tommy and I gave the same treatment to Richard's mom in her I Dream of Jeannie outfit. It was very easy to rip off her sheer genie style pants leaving her only wearing her green panties and genie slippers. We ripped off her blouse, and she surprised us by wearing a nice matching green bra with the nipples cut out similar to my mom's.
We had all agreed earlier than each one of us would have the pleasure of ripping off our own mom's or stepmom's panties and keeping them as a souvenir. Brian wasted no time grabbing his mom's panties at the waistband and savagely ripped them off while he continue squeezing her tits. He held her panties up to his nose before he put them in his Chucky costume pocket. He immediately buried his face and his mom's shaved pussy.
It was now Richard's turn to have some fun with his naked mom. He pulled a pocket knife out of his Freddy Krueger costume. He pulled her genie halter top away from her body and cut it in half between the cups and watched as her big tits fall off to the side into her armpits. He reached down, pulling his mom's panties away from her body and sliced them on both sides. He yanked them out from between her thighs, put them up to his nose and then stuffed them in his costume pocket. It was time to treat ourselves to the mother's asses.
We rolled both women over on their stomachs and focused our efforts on their ass cheeks. We all enjoyed gripping and squeezing and pinching their ass cheeks so hard we made both of them scream out loud. We all decided to spank them. We loved the feel of our open palms slapping each one of their ass cheeks multiple times. We all took turns on both moms until their cheeks turned red.
We agreed not to leave any marks. The sound of our hands cracking across these two big tit milf moms, was amazing. So was the sound of the screams and moans as each open palm slammed down on their ass cheeks. We continued slapping their cheeks until they both started to cry. It was a total turn on being able to make two mature women cry like naughty school girls being punished. Then came the big decision. Do we fuck them or not?
We all wanted to experience the feeling of our teen cocks buried up inside both Brian's and Richard's big tit 45 year old milf moms. However we decided against it. We didn't want to leave any jizz or DNA on their bodies. Instead we pulled them up on their knees so their pussies and assholes were right in front of our faces.
All of us were rock hard taking turns eating out both of their assholes and of course their mature pussies. It was a total turn on watching Richard and Brian eat out their own mom's holes. To finish them off we did our bowling ball move on them, which means two fingers in their pussy and our thumb up their asshole.
Once we had treated them both to multiple orgasms, we left them tied up on the living room floor. We would come back later to untie them, but now it was time to pay my stepmom Cathy and Tommy's stepmom Gloria a visit.
Gloria and my stepmom were also dressed up in Halloween costumes. Gloria was dressed up in one of my moms stewardess outfits and my stepmom was dressed up as a sexy version of the Wendy's hamburger girl with pigtails and all.
Our plan was the same as it was with the first two moms. We made sure nobody was around, bullrush the door, punch them in the stomach so they couldn't scream, turn off the lights and drag them to the back of the house to gag, bound and blindfold.
I was still upset with Cathy over the shower incident so I made it a point to give her two belly punches to shut her up. Brian and I ripped off her Wendy's costume. I ripped off her cute little blue and white panties and put them in the pocket of my Jason costume.
Tommy and Richard made quick work of Gloria's stewardess costume by ripping open her white blouse and cutting off her black lace bra. They rolled her on her stomach, unzipped her skirt and pulled it off over her feet, leaving her laying wearing her nylons, shoes and a black thong.
Tommy immediately ripped off his mom's black thong and stuck it in his Michael Myers costume pocket. We all intended to jack off later that night using each of our own mom's panties, and then hide them away for future use.
We went to work on both of their soft, white asses as we had done with the other two moms. Once again their screams and moans with each spank gave all of us raging hard cocks. We wanted to fuck the hell out of them but we all had agreed not to do so. Instead, we pulled them up on their knees and explored their assholes and pussies with our tongues just as we had done with the other two moms. We then did our bowling ball move and jerked them both to climax.
Once we were finished with all four mature women left them bound and gagged and we went back to my house to change back into our street clothes. Since all of our dads were out of town we obviously we had to go back and untie our moms. That also gave us another chance to get some screenshots of our four damsels in distress.
Tommy and I went to his house to untie Cathy and Gloria and Brian and Richard went to Brian's house to untie their moms and get some screenshots before we untied them and took off their blindfolds. Of course we had to act shocked, and totally surprised, and we did our best to comfort them.
They put on what was left of their Halloween costumes and returned to their homes. All four of us nasty boys jerked off in our damsel's panties later that at night and we all slept like a baby with the aroma of their panties under our pillows.
The next day I asked my mom what had happened the night before but she did not want to talk about it. None of the moms and stepmoms suspected that their sons and stepsons had been the ones to turn them into total mature damsels in distress. None of us were sure if any of them ever talked to their husbands about the incident, but nothing was ever said to us.
To this day, all four of us evil boys still blame our behavior on True Detective magazine for pushing us over the edge of bondage and BDSM.
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