That First Step free porn video

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Main Characters:

Jean, Female, 43
- Stepmother of Jason
- 5’7, 140lbs, beige skin, dark-mahagony hair over her shoulders
Jason, Male, 17
- Stepson of Jean
- 5’10, 150lbs, beige skin, wavy/lightly-curly blonde hair to his neck

Women know lust, too, you know. I don’t know why so many people, especially men, seem to think that we only think about sex as a passing interest, coming and going without another thought. It was never so for me. From my earliest days of puberty, I was constantly horny and explored a lot of things over those early years, some great, some not so much, but sex was always an integral part of my thoughts and how I interacted with the world.

And men hold no solo grip on perversion, on taboo thoughts, on desires which can only be spoken of carefully and with those you trust. Some are simple ones. Enjoying the vulnerable sensation of being bound and blindfolded. Or wearing a skirt with no panties and showing anyone, of any age, what was between one’s thighs.

Some of us have more complicated desires, more forbidden fantasies. Some of those fantasies become real, and with those lucky enough to be the ones we choose to participate, there are witnesses out there capable of assuring anyone that, yes, some of us women are turned on by that, whatever secret taboo act that is.

For me, it started when I was in my early twenties. I was passive about my interest in teenage boys, even though the age difference left a little more grey area than it does for me now at forty-three. Passive, in that I imagined and fantasized and used the memories of boys and young men I saw or met to fuel a fire when my fingers danced between my thighs. I used my toys and pretended some handsome high school boy was sliding inside me. Those weren’t my only perversions, but they were my favorites.

I married once in my thirties to a man who was a terrible match. Not personality-wise, but sexually. He was creatively sterile and vanilla in his pleasures. Sex with him was okay, sometimes great, but he held no interest in trying new things. When I’d shared a fantasy with him once, about a young man of maybe sixteen, he shut me down and shamed me for thinking of anyone but him. The marriage was dissolved within weeks. I needed more taboo stimulation than missionary sex followed by a blow job.

Other than my first husband, no one had ever shared my secret, the one where I was passionately attracted to high school-aged boys. That fire has burned all my life, and a dark part of me knew that, if I ever found myself in the perfect moment to act on it, I would do so with little hesitation.

I regularly masturbated to porn featuring teen actors, even gay twink scenes. Those, especially, featured young looking boys, often waxed and looking younger down below. I imagined it was me spreading my legs for those boys and being filled with their hard penises until I orgasmed myself silly.

I married my second and current husband, Todd, a little over a year ago, and though I would never admit it to anyone, part of why I did so was because he had a teenage son.

Oh, I liked Todd well enough, but always in my thoughts about him were those taboo ones about his son, Jason.

I’d known Todd for several years, ever since Jason was nine or ten. We were friends, both of us moving in and out of other relationships and eventually dating. I moved in with Todd and his son a few months before the marriage, and I never missed a voyeuristic chance to admire and fantasize about Jason. Often, when Todd was inside me, I closed my eyes and imagined his son was the one pounding me. Honestly, after almost a year, I’m not sure I could climax with Todd any other way.

But Jason was special in another way: I’d seen his penis and testicles a few years earlier, when he was fourteen or so, and that only added fuel to my fire for him, growing stronger over the years as I craved more of what I’d seen that day.

We’d been walking together, the three of us and a handful of other friends, along a sidewalk downtown, heading for dinner after catching a baseball game that afternoon.

I’d barely turned my head at an odd sound to feel something swipe by me, fast and hard, sending me spinning off towards the buildings. I heard screaming, banging my knee hard. I looked up to see a car careening down the sidewalk, immediately slamming into one sign and then another, finally stopping fully when it crunched against the corner of a brick laundromat.

As the radiator hissed and people check on the driver, I saw most of my friends rising to their feet. None of us were seriously hurt, but I lost my sense of priority and reason when I saw Jason.

I found out later that the car had swept a little closer to him, catching his shorts on something and tearing them from his body, ripping his briefs, and sending him spinning. He had scratches and scrapes, nothing broken, but none of that even when through my head when I realized the rip in his underwear had left his groin completely exposed.

Jason was only fourteen, but his penis was rather nice and thick, perhaps six inches already if it had been hard. It bounced and swung as he tried to steady himself on his feet, dazed and not aware of his nakedness.

Oh, but I was.

Tufts of dark fur rose over his shaft, more around it, sparser covering on his young sack. I nearly creamed myself, unable to look away, unable to even consider thinking about checking on the others. For as long as he was uncovered, I think I was stuck.

Until he looked at me and saw where I was looking. Jason cast down and immediately understood his nakedness, covering his groin from my eyes and snapping me from my spell.

I tugged off my jacket and went to him. He was shaking lightly. I said words, he did the same, but all I remember was how badly I wanted Jason’s cock right then. Wrapping the jacket around his waist, I tried to peek into the rip and past the boy’s covering hands, but I was denied one last look at such a sexy presentation.

The jacket tied snug and he thanked me.

After we’d been patched up and checked over, we decided we all needed a drink and headed to a bar instead. No matter what we talked about that night, my thoughts were peppered with fantasies about young Jason.

He was a bit younger than those I usually sought, but I didn’t much care. His cock looked like that I might see on an older boy, and that was all that really mattered. I probably orgasmed to that moment more times over the next few years than all my other fantasies combined.

When Todd and I began to date, the arousal of that sight only grew stronger. I saw Jason more often than before, the boy then about sixteen. He was polite but a little aloof, wearing his blonde hair down over his neck in long, sweeping, carefree curls. Average height, I think, a little shorter than his father’s five-eleven, but with a stocky build, muscular in his shoulders and waist, a rising star in the high school wrestling circuit. Seeing Jason wrestling on the mat with other fit teen boys, wearing tight outfits which showed strong and handsome bottoms, only made me seek out more gay twink videos and pretend it was Jason pounding a feminine-looking teen boy.

After moving in with them, I sought out chances to let my voyeuristic side explore my forbidden thoughts about Jason. I sniffed his underwear regularly, sweaty and musky and wonderful. I snooped his browsing history and was not surprised to find a lot of porn sites being visited. Many of them, to my intense thrill, were MILF videos.

I tried to catch him in the shower, or to let him catch me there, but it never seemed to work out. He was in his underwear a time or two, but only briefly. Still, it was incredibly arousing to live in a house with such a beautiful teen boy.

Since his father often traveled for work, I had opportunities to do things like listen outside his bedroom at night. I was rewarded a few times, usually first hearing low-volume moans of whatever porn video he was watching, and then, sometimes, a few lovely grunts as Jason ejaculated. I almost opened the door several times to watch and offer him the real thing, but I held off for obvious reasons.

But I knew, the longer we lived in the same house, the more opportunities I had to be directly aware of his sexuality, the harder it would be for me to not turn that knob and take a taboo chance of a lifetime.

Jason turned seventeen a few months after Todd and I married. With Todd gone most weekends after our honeymoon, I decided to see if I could push things. We had a pool with a lot of privacy, so I started sunbathing topless on Saturdays.

The first couple of times, Todd never seemed to notice. Or if he did, the teen didn’t take advantage. The third time I was topless by the pool, I pretended to sleep, letting my head roll to one side and making light snoring noises. Todd came out slowly, not looking at me for a moment, then sat down and stared at his phone. It didn’t take long to realize he was using his cell to take pictures of me. Since I wore dark shades, I could see what he was doing while I continued to feign sleep. He sat there a good ten minutes, taking one shot after another, before he rose and disappeared.

I had no doubt he was masturbating and followed him very quietly, listening outside his door. Disappointment followed when I never heard his grunts, but I had enough success that day to encourage me to push things again.

My fourth attempt, I went to his room and knocked on his door, “Jason, it’s nice out, you want to come out and swim and get some sun with me?” It wasn’t unusual for me to invite him to do things with me, even if many of those were for at least somewhat innocent reasons.

“Uhmmm ... yeah ... okay, Momma Jean,” he called through the door.

I walked out to the deck and removed my top, sitting on the edge of the pool and letting my legs hang into the water. I’d specifically chosen the bikini bottoms that day, knowing what effect they should have on Jason. It was just a string in the back, and the front only a small, sheer white triangle that barely covered my cunt. I tended to let my pubes grow full, and the bikini bottoms left tufts of my fur sticking out around the material.

Jason joined me, wearing only a pair of dark trunks. He didn’t look at me for a long time, sliding into the pool and slowly swimming around. I decided to offer him a show, of sorts. My breasts already visible, I lay back on the decking, letting my head rest on a towel, spreading my thighs a few inches so that Jason would have a nice view in between.

I couldn’t see whether he was looking, but I had no doubt he was. I heard the water slosh a while, then it became silent. I was creaming myself just knowing what Jason could see of me. Very slowly, I rolled my head until I could just see over my body. It was not a surprise to see the boy on the other side of the pool, still in the water, his eyes staring right between my legs.

He noticed that I had looked up and tore his eyes away, diving under the water and disappearing.

When he surfaced, I made a show of removing the rest of my bikini, pausing, and then sliding into the water and swimming towards him. Jason’s eyes had darted between my naked body and everywhere else until I was mostly submerged.

“Sorry,” I told him, “I decided I don’t much like tan lines, do you?”

He shook his head, “Nah ... not really...”

“Does it make you uncomfortable? That I’m naked?”

Another shake. “Nah...”

“You can get naked, if you want. I won’t tell your father...”

I don’t know if Jason knew right then what was happening, but I certainly did. I was pushing my fantasy forward, taking a chance that my stepson wanted me, too.

“Uh ... I dunno ... Like ... Dad would kill me and all, cause, you know...”

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Sissy Stepmother

Sissy Stepmother A Pantyboy Profile INTRODUCTION Cheryl here. You remember me. The 20-year-old pantyboy extraordinaire. Every man's naughty, secret, wet dream. Raconteur without equal. In "Service" and "Test Driven," I told you about Amy and Judy, two of my lovely roommates, fellow pantyboys and like me, covergirls for "Panty Boy," the only publication worth buying, besides some of those Spermco comic books about us "special boygirls" and the "Sunday New York Times." And Panty...

1 year ago
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Spanking My Sexy Stepdaughter

Sara was wearing her high school cheerleader uniform, and it was impossible for me to look away. Sara turned 18 years old last month, and her body emphasized her age and her current status: barely legal. Three weeks ago, I legally married Sara's mother, Kelly, and I moved into the house that she and her daughter shared. While I was attracted to Kelly, I couldn't avoid looking at her beautiful 18-year-old daughter. Sara had brunette hair, dark green eyes, and slightly tan...

1 year ago
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Conquer and Suck Seed Part 1 Steph

In the darkness of an empty office floor, there were only two audible noises... "Yes... fuck yeah... yes..." A woman's voice echoed between the empty cubicles, illuminated only by the light coming through the windows from the city skyline. Jay pounded into her, his thick veiny cock made slick by her pussy, ever growing wetter the harder and faster he thrust, the slaps of his thighs into her ass cheeks loud as a clap in anyone's ear. Her magnificent tits bounced above the neckline of her red...

Office Sex
3 years ago
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The Sneaky Stepson

Foreword – This story though of a familiar genre was inspired by a letter to Dear Abby that contained the line My husbands son – Ill call him Duncan – came to visit The Sneaky Stepson By rutger5 (An original story- copyright 2012) Dont misunderstand me honey, Im not dismissing your concerns but I believe youre overreacting a little is all&hellip, Overreacting? I dont think so Paul. If it was the shoe on the other foot you wouldnt feel the same Im sure Tara Ferguson replied to her husband....

2 years ago
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Breastfeeding My Stepson

Hello.. I want to tell you about how i started to breastfeed my stepson and start to have new lovely bond with him till now. Before let me introduce myself. Myself riya and i am my husband’s second wife. His first wife was actually my elder sister who had meet with an accident and expired so later on my family made me marry my sister’s husband only. He has teenage child shreyas who was now also my son. Days passed on and i gave birth to a baby boy. My relationship with my step son was not good....

Incest
3 years ago
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Stepping Out With Steph

Chapter 1 Blair and Stephanie grew up in a household with a divorced mom, who was fairly conservative in her beliefs, being the sister of a minister. Blair was only 16 when his older sister caught him staring at her and her friends, and responded to this "lewdness" with an atypical sisterly gesture- she teased him by flashing him her breasts. No doubt their mother would have disapproved of this action, but she never learned of it. In any case, Blair's reaction affected Stephanie for years...

1 year ago
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Spanking My Sexy Stepdaughter

I was reading the comics section of the newspaper when my stepdaughter, Sara Vorrez, walked into the kitchen. Sara was wearing her high school cheerleader uniform, and it was impossible for me to look away. Sara turned 18 years old last month, and her body emphasized her age and her current status: barely legal. Three weeks ago, I legally married Sara's mother, Kelly, and I moved into the house that she and her daughter shared. While I was attracted to Kelly, I couldn't avoid looking at her...

Taboo
3 years ago
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Naughty Stepdaughter

I met my wife Karen at work one day, and a few weeks after our first date, i met Stacey her daughter.Now Stacey was a young teenage girl, and did look just like a younger version of her mother, she was petite, blonde and very friendly, and when I proposed to her mother she was more than happy to have me as her new stepdad.So we moved into a house together as one small happy family, and I got to watch Stacey over the next few years, turn into a beautiful young woman.Now one evening the football...

1 year ago
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Webcam Model Becomes My Hot Stepdaughter

Hello ISS readers. This is a father sharing his experience of a live video sex chat session with a bold, playful, and seductive webcam model of Delhi Sex Chat website. The truly helped in exploring my pervert desires over my 20-year-old stepdaughter. Moreover, the open-minded webcam model was exceedingly erotic. A few days ago, one afternoon, my stepdaughter came home from college. I had taken a day off from work and was watching TV in the living room. I waited for my stepdaughter to come out...

4 years ago
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My Stepdaughter

   My name is Terry and I'm thirty-three years old. Not exactly in my prime anymore, but I lift weights for at least an hour every day so I've got a pretty good body. I'm told I look something like Jean- Claude whatsisface, the martial arts star, though I'm not quite as muscular nor as handsome. Still, I'm in fine shape for my age and I feel even better. I have more energy now that when I was sixteen. Three years ago I married a woman who had a daughter by a previous marriage....

1 year ago
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Bonding With My Stepson

John, a straight forty-year-old, takes his eighteen-year-old gay stepson's virginity. To please his wife and bond with his stepson, John asks Aaron if he wants to learn some mechanics with him. As they have a nice moment together, John discovers something he had never felt before, a need hidden deep inside him. He's going to breed the young gay boy. New message from Sandra — Don’t forget what we talked about! Go talk to Aaron. Luv you. I read the text message from my wife and put...

Gay
3 years ago
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Uncontrollable Cock 8211 Part 1 My Sexy Stepmom

Hi everyone, my name is Pratyush, and I am from Nepal. I have been a regular reader of ISS (especially after meeting my sexy stepmom) for more than 7-8 years now. When I first came here, I was a virgin, and now, I do not even know how many girls I have slept with. Finally, I realized why not post my stories here in ISS, the same ISS that has taught me so many things. Before starting, I would like to thank every writer here in ISS who has shared their stories and helped people relieve their...

Incest
2 years ago
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Stripping Steph

Steph was late from work and rushed though a simple game night was all we'd planned. Ted and Ursula were already here and had a libido loosening three drink head start. I suspected that my hints about what kind of games I had in mind were correctly understood. Both of them wore loose fitting orange shorts that were tailored around their butts, her's were neon! Despite her bountiful bust, Ursula wore a braless, thin and fragile, yellow, button down top. It was an interesting cross between a...

3 years ago
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My New Stepdaughter

I met Helen at the park one day, we were both out walking our dogs and just bumped into each other, and the instant i saw that mature 30 something blonde woman in her summer dress and sandals, i knew i was going to be with her forever.As it turned out she was just a couple of years out of a divorce, and after some friendly chatting, she agreed to go on a date with me and the rest was history, we fell in love, moved in together a few months later, and now a year on we we're preparing to get...

3 years ago
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My Wicked Stepmother

It's was my last summer before I was supposed to start college. I had the house to myself most the time and had been wasting my summer playing video games. My dad was always gone on business trips, and my stepmother was usually out shopping, or at the gym where my dad met her.On the Saturday afternoon in question, my stepmother had just gotten home from whatever or 'whoever' she was doing, and my dad was out of town on 'business' again. I didn't really care how screwed up my dad and...

Taboo
4 years ago
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Young Stepmother

Young Stepmother Chapter 1 By Mark Dayette Looking back on it now I had an easy life when my parents were still alive, I was their only son, their special boy Nathan, they called me Nate. I had a childhood like any normal boy, I wasn't exactly one of the cool kids, I wished, but I never felt like I was a loser. My family lived in Philadelphia, PA. For many years Dad took me to the Flyers games. As a teenager I had a few dates but I wasn't too successful with the ladies. I hate to...

2 years ago
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Bonding With My Stepson

 ... New message from Sandra — Don’t forget what we talked about! Go talk to Aaron. Luv you....I read the text message from my wife and put back the phone in my pocket. Aaron was her son. After living with his father for a few years when he was a teenager, he came back to his mom’s at the beginning of the summer, as we were living closer to his college.I never had children with my first wife, so kids were not my specialty. Well, he was eighteen, so not really a kid anymore, but still, we barely...

Gay Male
3 years ago
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Vacation with my stepson

Hi Y’allMany people have commented on my last story of an amazing random cock I sucked while on vacation. The main private comments I received were wondering if my stepson tried anything with me while I was in Utah and he was joining us from 29 Palms where he is stationed. I’ve been reluctant to say anything but have to admit we did have a little fun. The first time something happened during the trip we were sitting in a cabin we had rented outside of Capitol Reef National Park. I was in the...

3 years ago
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Husband Told Me I Could Have Sex With My Stepson

I’ve been married to my husband nearly three years now, I’m 28 and he is 45, I was probably the cause of his marriage break up with being his secretary. He has a son and daughter 17 and 15 from his first marriage, which we often see, and I get along fine with.Four months back my husband suffered a stroke; he was paralysed from the waist down and needs a lot of help all the time. Jake my stepson came and stopped with us to help look after his father. Jake is used to having girls stop over at his...

2 years ago
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Watching my stepsister

Watching my I was 17 at the time and was dating a lovely girl name Cassi. My stepsister was 19 just out of school and was dating a guy name Marc. Our parents went away for the weekend on a with two of their friends leaving the thursday afternoon, leaving my sister and I alone at home till the Sunday. The Thursday evening my sister and I while having dinner discussed what our plans where for the weekend. She was going to be out with her boyfriend as well as at home and I told her that I would...

3 years ago
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Blackmailing My Stepmom

“I’m in love with my stepmom. I don’t live with my Dad, but I stay with him and her two weeks a month. I swear, those two weeks are constant masturbation for me. She’s 18 years older than me, I’m 18. But, for some reason I always wanted to fuck her. I’ve known her all my life. She stays home and takes care of my half baby sister, while my Dad goes to work. I’m always sneaking around trying to catch her bending over or something. Taking a shower. Lying out in the sun with a bikini on....

Incest
4 years ago
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THE STEPMOM

Ever since I learned what masturbation was, my stepmom Pammy became my #1 jerk off subject. After every weekend I spent with my dad and stepmom I would come home and my dick would be so sore from jerking it off all weekend. I was in high school when I really started to notice Pammy; she was 37 at the time. I don't know if she would qualify as hot to most k**s in my school, but she drove me wild. Pammy is average height with a slender body. Tits were 34B, I knew from always looking at her bras,...

3 years ago
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Caught by My Stepmom

I thought my stepmom was hot, but I never expected this!I was watching porn in my bedroom one day and wanking off when my stepmom came in and caught me! I tried to hide my cock, but it was too late.“What are you doing, Joey? Are you watching porn?”“Yep. You caught me. So what? I’m not hurting anyone.”My stepmom is about thirty-five, has long blonde hair, big boobs, and I’ve often thought she’d be a nice fuck. But to have her catch me with my cock in my hand was not what I’d envisioned ever...

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