Stepmom Gets a Deep Anal Plundering
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When I was fifteen my mother left my dad and me. It wasn’t her fault; my dad was such a hound dog. As much as my mom and I wanted to live together, she told me that she had almost no money, seeing as how my dad made her sign a pre-nuptial agreement when they got married, leaving her with little money of her own. My mom and I are still really close and we typically see each other at least once a week.Within a year my dad found the perfect kind of wife for himself: a gold digger by the name of...
InterracialBBW StepmombyFrank2002©It seems I always had this thing for bigger, full figure women. I don't know where is started but I seemed to fantasize about them all the time. My step mom was a bigger woman. My dad divorced and remarried when I was very young. He was away quite a lot with business so it was just me and Sally, that's my stepmom, at home most times. I always thought Sally was quite attractive even when I was young. As I grew older I started to notice her more. She had put on a few more...
Another hot but fictional story. I was sixteen, it was coming close to the end of the school year and one day I got sent home early from school and my dad was away on business for the week. I walked home wearing my short plaid skirt, white blouse, knee high socks and two inch heels, with no underwear. I arrived home, but before I got inside I heard some voices around back, so I decided to go check it out. As I made my way around, I noticed my stepmom, who was actually only 22, in her smallest...
Group SexAfter positive actions with my sexy stepmom, my hot sister, and Nisha, I jerked off my cock and had one of the best orgasms. I had cum in my underwear. So I went to sleep naked, leaving the dirty underwear on the floor. In excitement, I didn’t even realize I had left the door open. The next morning, I was still not fully awake when I heard the sound of the door opening. As always, my stepmom had come with a cup of coffee. I was half asleep and lying down on my back, exposing my semi-hard cock....
IncestLizzie and Madison go out (This is entirely a work of fiction.) Sunday evening. Paul answered the phone. "Hello." "Hi, Madison. Lizzie here." Paul is a crossdresser. Madison is his femme name. "Hi, Lizzie." Lizzie is also a crossdresser whose real name is Simon. Simon is Paul's best friend. Simon and Paul (as Lizzie and Madison) regularly enjoy nights out together. They were planning a night out together the following Wednesday, probably meeting up with fellow crossdressers or...
“Madison are you sleeping, honey?” Jim her father didn’t hear any response and opened the door and sauntered into her bedroom. He came to the side of the bed and gazed down at his youngest daughter, his teen ‘sleeping beauty’. Standing over her Jim released his manhood from his boxer’s and began to stroke his cock. Jim had no problem getting hard as quickly as he did. The many memories of taking his daughter right there in her bed flooded into his head. “Come on baby please wake up....
Courtney was in her mid thirties and wanted to get back into shape and her husband Gene had suggested taking yoga lessons to get her flexibility back as well as lose about 20lbs. When Courtney started taking classes she noticed how beautiful her instructor was. Pamela was in her late 20’s and was a stunning young woman. Courtney somehow always found herself directly behind her in class. There was something about how Courtney admired Pamela’s pussy as it was outlined with her leotard as she...
Scott's had recently turned 18, for his birthday his father and his stepmom decided to get his own laptop so he didn't have to share the family computer no longer. Scott resented his stepmom, he hated the way she made him address as her as Mom or Mommy. Scott's real Mom ran out on him when he was little boy, so now he lives with his father (40), stepmom (52) and two half sisters both younger.Scott was a total nerd, top of all his classed, member of the chess team, and the AV club. He had never...
Madison By Anon Allsop I sat upon a little bench and watched shadows race across the open expanse of the lawn. Deep were my thoughts as my mind filtered out and processed, what had gotten me to this exact place in my life. Glancing at my watch, I saw the dial reflect the sun as it broke through the cloud that raced overhead. I squinted at the sudden glare, angling the face so I could see the dial. Ten minutes till two. I had forty minutes until I would be forever alone. I leaned...
The RV was not very big. It was advertised as ‘Comfortable for a Family of Four’ when dad bought it. It had one standard sized bed for two in the back, hidden behind a door that folds out from the bulkhead. The other sleeping arrangement for two was a bunk that could be made by dropping the only table on the bench seats and lying the seat cushions on the flat surface. That’s where my sister and I slept when we traveled. The first few years it didn’t bother me to sleep beside Madison...
I was right in the middle of finals week at Reed College, and I wasn’t in a good mood. The spring weather was glorious for a Portland campus; the flora was intensely green and in full bloom, and girls were dressed in light summer clothing, which meant that as I drove out of the parking lot, it was hard to miss the legs, cleavage, and everything else that gets a 19-year-old guy’s hormones flowing. I was horny but pissed that I couldn’t stay. I had to drive 30 minutes back home to walk the dog....
Madison leaned on her pillow with a mischievous grin. She squeezed her husband’s cock, surprised to find it hard so soon after lovemaking. “So this talk of me with another man really does turn you on,” she said. She rolled over to fish another condom out of the bedside drawer. When she found one, she lay on her back, parted her legs, and smiled at Ryan as he climbed between them. Ryan took the condom, unwrapped it, and rolled it onto his penis. “Yes,” he answered....
Note: This story is completely fictional. Firstly, I would like to say a little about myself. My name is Paul; I am 18 and live with my dad, Joe, and my stepmom, Nicola. I am 6"2 and am fairly muscular and have a 6"3/4 circumcised penis. Right, where to start... Well, earlier I said I live with my dad and my stepmom, that isn't really the case. See, my dad works abroad a lot, last year he was at home for just three months. This meant that it was just me and my stepmom living together. She had...
IncestMadison was working for the caterer to earn money for next semester’s books. She really didn’t mind the work, with her great looks she always was assigned to the wait staff. She found it interesting to mingle with the crowd and pick up bits and pieces of the chatter. Her long blonde hair and piercing blue eyes got her the job, as well as a spot on the university cheer squad, all of which she hoped would pad her resume for when she graduated next spring and had to find a real job. She was 22,...
InterracialMy neighbor, Madison, had done me a major good deed. First, she gave me the best loving of my life. Then, she brought out the real side of my wife, Natalie. All of this effort brought rewards to Madison, too. She was getting all the sex she could handle from both me and Natalie. She was one happy young lady of twenty-three, and she showed it as much as possible in as many ways as possible that involved acts of sex and lust.Natalie still had to go to work everyday. She was a major corporate...
Group SexHello, my Dear Readers. I have been writing incest themed stories, focusing mainly on mom-son relationships, for some time now. I wanted to try something light-hearted, featuring a young & naive stepmom and her stepson, who is expecting nothing sexual from her. This is my humble attempt on the same. Happy Reading! Sidharth was both bothered and excited. He had just landed back in Mumbai, after completing his studies from a university in the UK. He was on his way home, and he was going to meet...
IncestHaving graduated from college, I started my own business in commercial design and construction utilizing the skills I had learned while working in the construction industry and my studies in architecture and engineering while in college. Seven years along, I was doing very well in business but working long hours. I had been in a few rather serious relationships but eventually, the females I was involved with realized they came second to my career.At age twenty-eight, my mother, who was now...
First TimeIntroduction: The beginning of a very dark secret (society that is) Jim leaned back in his office chair and yawned as he stretched. Then spun around and was greeted by the beautiful New York City skyline. Jim stood up from his chair and walked over to the window and looked down from his perch some 50 or so stories high. He thought to himself, out of all the city skylines in the world, New York’s just seemed to feel like home. Summer time just appeared to be the most beautiful time of...
It had been only a week since Madison had found out what it was like to be made love to by her artist neighbor. We had not been alone together since that time. Because she had just completed a case my wife, Natalie, had arrived home at a normal time each day. During the day Madison had become serious about finding a job, so she was away all day long. I had told all my neighborhood lovers that I was off the market. I didn't give them any reason, but I found that they were really understanding,...
Group SexIt was well past midnight when I got home from my last date with my now-ex Sarah. I had dropped her off at her house, having resisted the urge to tell her to go to hell and walk home. Getting dumped was bad, but having to drive her home was extra insult. As I pulled into the driveway I shook my head. This was the second time in a year I had been dumped, and for the same reason. I unlocked the door as quietly as I could, hoping to wake no one. I passed my stepsister Liz's door and then turned...
I was never much for working out. It had just never seemed like an important thing to do. It was probably because I maintained a decent physique despite the lack of training. I was 6’ tall and weighed about 170 lbs. Being a teenager with a decent build and an active metabolism I didn’t know why I would ever want to put myself through rigorous physical exercises. My stepmom, Ava, hated that I didn’t like to work out. She was a personal trainer and spent all her free time shaping and toning her...
Introduction: Ive decided not to state the ages of the young girls in this story. This is to allow the tastes of the reader to fill in the blanks with their own preferences. As I wrote this, I found myself re-editing it several times, but eventually you need to just accept that a piece is finished, and share it. This chapter has alot more speaking and less actual sex than the first to parts did, but I think it builds nicely on what has already happened, and sets the scene for part 4. enjoy....
Becky rushed to the door to answer, knowing her best friend, Madison, was supposed to be coming over. Becky had needed to rush to get cleaned up and dressed before she arrived, as she had been getting throat fucked by her daddy only 15 minutes ago. She was wearing a pleated mini-skirt that barely covered her bubble butt, a spaghetti strap top, socks, and a pair of sneakers. She never wore panties if she could get away with it, because she liked to feel the breeze blow across her cunny lips...
My step mom, Tracy and i had an odd relationship, which started when she found a bag of weed in my backpack.She looked at me and said "i have 2 options, tell your father or keep it a secret""Please dont tell dad" i begged. Instead of calling dad at work, she opened her purse and pulled out a small change purse, zipped it open and pulled out a little metal pipe!"For your punishment we are going to smoke the whole thing" she said. She would act motherly, but when dad wasnt around she didnt care...
Madison looked on in rapt attention, as she watched her best friend Becky, who had a strong dislike of panties, on her knees, with Becky’s mother, Marie kneeling beside her, in front of Richard, Becky’s father. Richard was sitting in his favorite comfy recliner, with Becky’s little hand wrapped around his cock, while she prepared to demonstrate to Madison her best techniques for getting at her father’s cream. According to Becky, every morning, one of the first things she would do was sneak...
Shortly after my eighteenth birthday, I was in my head with resentment that my dad and stepmom had kept me in all-boy schools since I was nine. They were strict about dating, my ascetic lifestyle and the health risks about intimacy. With those fears drilled into me, I barely dated, and those dates I did have were always chaste. Emotionally, I knew I was still thirteen. When a girl tried to kiss me, since I wasn’t trying, I made fearful excuses and avoided the inevitably painful death from...
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...
IncestMadison Parker stood in front of her full-length mirror, admiring herself in a new pink bikini.She had just had her seventeenth birthday, and, in September, she would begin her senior year of high school. She was dating the star of the school’s baseball team, who was away attending a camp for young men with the potential for playing professional baseball.Madison turned back and forth, studying her body. Her mother would disapprove of how much of her butt was showing. Nor would she care for the...
First TimeMadison woke up late on Saturday morning. She grabbed her phone from the nightstand and noticed it was almost 11:30. She stretched as she thought about what happened the previous night.After attending the high school football game with Dennis, they headed to their favorite parking spot to fool around. Dennis had turned out to be a good and thoughtful lover. He did his best to see to it that she was satisfied. However, Madison couldn’t help but draw a comparison between Dennis and Robert....
TeenIt was Summer and school was out, normally a time of fun and relaxation. For me, it was a time of trauma quickly followed by anger followed by resignation as my girlfriend of a year and a half dumped me. Well, shit. Not only that, the news spread like I’d won the lottery. The only good thing was that I heard right away from two friends who had been in the same boat, then dumped overboard. I had gone through elementary school, then middle school with Madison and Cindy, and we were always pretty...
It was Summer and school was out, normally a time of fun and relaxation. For me, it was a time of trauma quickly followed by anger followed by resignation as my girlfriend of a year and a half dumped me. Well, shit. Not only that, the news spread like I'd won the lottery. The only good thing was that I heard right away from two friends who had been in the same boat, then dumped overboard. I had gone through elementary school, then middle school with Madison and Cindy, and we were always pretty...
Group SexFor Madison Parker, senior year of high school was going way too fast. Thanksgiving week had arrived, and her older sister was due home from college at any minute. Maddi was excited to see her older sister, Abigail. So much had changed in her life since Abbi returned to college. She was in love with Dennis, and they had been having sex regularly, something that had been encouraged by their mother.As she lay in bed, Maddi heard noises coming from the kitchen. She remembered that her mother had...
ThreesomesMadison Parker woke up absolutely giddy on the first day of Christmas break. Not only was her older sister Abigail home from college for the holidays, but so was their sexy neighbor Robert. Maddi still felt a little guilty that she hadn’t told her boyfriend, Dennis, about all of her sexual escapades with Robert. But then again, she was pretty sure that he had learned a few things about sex too while he had been at baseball camp the previous summer.Maddi wandered into the kitchen and found her...
TabooI am Peter and my marriage had lasted over twenty years, but it had stopped being a real marriage long before. My wife had wanted a career of her own. I was fine with that. It left me time to stay at home and do my artwork. I sold enough pieces to make it worthwhile. Of course, Natalie, my wife, worked late often. She was a lawyer. Because of this I decided to ride it out and just take care of myself. I knew my wife well by now, and she could have raked me over the coals in a divorce. I just...
CheatingTrue story. My stepmom and my Dad came home one night both drunk after being at a party. Stepmom is 45 and a total milf, she has huge tit's and a biggish ass, she has the classic hour glass figure. Dad is 49 he has kept himself well over the year's, I was 15 at the time. stepmom was wearing a knee length skirt, she sat down opposite me, I caught a glimpse of thigh as she sat down, she sat there with her leg's slightly apart, I was enjoying the show, when Dad said to Mom "come on honey bed time"...
As I made my way into the house,I flipped the light on for the hallway. Kicking off my boots and hanging my jacket up,I walked to the living room to see the futon laid out. There was a little bit of light from the street light and could see Michelle laying on the futon. I figured she had watched a movie and decided to crash on the futon. I kicked off the rest of my clothes down to my boxers and laid down beside her. She flinched a little,which was nothing out of the ordinary,but she didn’t...
At 32, Madison Stevens was an experienced office manager and was being groomed for advancement with various assignments at different hotels in the chain. Her latest was a real plum, Grosvenor House, recently acquired by her company, one of London's classic hotels, on Park Lane, overlooking Hyde Park. Lots of celebrities stayed there, and, at the moment, she was pre-occupied with a "customer relations" problem, a touring R&B band which was staying for three days before moving on to...
How many of you mother fuckers remember the first time you saw Madison Ivy? When she first hit the scene, it was as if an alien species figured out how to craft the perfect woman, then sent her to Earth. Or if you are a spiritual dipshit, it looked like a real goddess was walking the Earth. My God, what a fucking body!Look, she’s still fucking hot. That body still hasn’t stopped. But time comes for all of us, and she made the unfortunate mistake of thinking that she needed to modify her face...
Twitter Porn Accounts‘Hey Maddie, you’re late,” Sheila observed, looking up from her stack of paperwork. “She’s already called to ask about you.” I glanced at the glow of the digital clock on her receptionist desk. 8:02, it displayed in nonnegotiable terms -- two unforgivable minutes overdue. I gave her a pleading gaze with my large brown eyes, knowing in my heart that she was powerless to help. “She’s in a state this morning,” Sheila warned sympathetically. “The new girl from Accounting has been in there for...
We start this week’s show with an establishing shot of a large, angular glass fronted building with the words “HUDDERSFIELD LEISURE CENTRE” standing on the front of its roof. As we pan along the front of the building, we come to rest on a slutty-looking brunette with a hefty looking blue-grey Weimaraner. It’s the last of this year’s three hosts, our perverted pornster – Renae Russell ... Her long brunette hair hanging loose, down to the shoulders of her white mini-dress – which is tight...
“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....
IncestEver 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,...
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...
When Jillian's period came a few weeks after her encounter with the boys she breathed a huge sigh of relief. So far her stepsons had not said anything to their father and she felt this was the last bullet she had to dodge. Despite taking a "morning after" pill she would not believe she was in the clear until she was sure she wasn't pregnant. She had never been so happy to have her period in her life. Her husband had asked during those weeks why she was so nervous, but she kept putting him...
As Greg Mathews watched his little girl, Madison, as she lapped up the last remnants of her ice-cream, he was sure she had no idea that the reason she thought it tasted different from usual this time was because her daddy had shot his cum into her ice-cream dish before making hers. Her daddy had been wanting to feed his little girl some of his cum directly from his cock for as long as he could remember, but he also didn’t want to traumatize his beautiful daughter. So he had decided that the...
Jim gazing at his wife from the other side of the bath tub and said, “You know there are so many things that you don’t know about my brother. Do you remember the flowery story that his daughters Kasey and Kaitlin told us of how Raymond took their virginities? Even that nice version of the story shocked not only you but me as well the first time that we heard of it. I am about to reveal to you the real story and events that you don’t know about. Do you when remember Raymond was in...
Sunday morning up before everyone else sitting with the New York Times and a cup of coffee. Such a peaceful way to start the day. I watched my wife Rachel stumble from our bedroom, naked, with the exception of her discreet sterling silver collar, and tattoo marking of my first initial "M" low on her groin. Her blonde shoulder-length hair was standing out in all directions, and her lips swollen. She looked like she'd been ”rode hard and put away wet"...I love that look, and I love that woman.She...
Group SexI don’t know how, but my housemate Aaron had recently learned about my competitive side. I have an identical twin, Madison, and he’s been goading me all week. Finally, last night, it came to a head when he said that my twin sister’s pussy tasted better than mine. “Like hell it does,” I basically said, jumped up on the counter, and pushed his head between my legs. After he told me that she orgasmed louder and more easily than mine, and the game was on. A couple of days later, I broke up with...
So I knew my stepmom would be really horny after a while. ”see you soon Jon im heading to Chicago for 3 Weeks”. Ok bye dad I hugged him and left to my room. after about half an hour my stepmom grace walked in. ”hey Jon” . I looked up and said hello. This is going to be the first time your father leaves us alone and I think this will be a good time for me and you to get to know each other. Yea I think so to. ”good well im going to order a pizza for us to eat im to lazy to cook today. Ok. All I...
It was 8 am Monday morning. Ryan had left earlier to catch a flight for a business trip that would last all week. Madison was just leaving to get to school on time. A truck, pulling a trailer with a Bobcat backhoe loaded on it, stopped in front of their house. Two guys got out of it and came to the front door. Expecting them, Kim had the door open as they approached.“Hi guys! Ready to start the project?”“Yes, Mrs. Harris. You know we have to drive that Bobcat across your lawn, into the...
TabooMy son was away working overseas for an extended period of time and his beautiful 21 year old blond hot wife was staying with my wife and I while going to college and saving their apartment money.She is a real hottie, 21 as I said, 5'5" with long sexy soft blond hair, big beautiful blue eyes, slim waist, perfect ass and nice big tits with hard perky nipples. Very hard to keep my eyes off her and ask "fatherly" as a father in law should. At the marriage I couldn't help but think how hot she...
She’s never called me daddy and those words kept playing in my head as I stood in the shower. I couldn’t help but think about how I had fucked Madison the night before and surely wasn’t going to forget the blow job she just gave me. She was so much like her mom,just the younger version. I had to get these thoughts out of my head. On my way to work I called Michelle and asked her how her day was and she said she should be awake when I got home since tomorrow was her day off. “I should be...
The thing that woke me was my phone ringing.I checked who was calling an found that it was my Mom,I did backtrack and remembered i was to go see her today.Standing there nude with my semi erect dick watching my naked step mom sleeping like a baby in the bed, who had been fucked 9 times or so in the last 18 hrs or so by me. I picked up my moms call greeting her,she was a bit mad because this was not the first call she made to me, other thing she made clear for me was it was 2 in the noon and...
Before I begin, I want to point out that the events of this story were a long time ago. I'm now firmly established in middle-age, whereas I had only just turned 18 when this happened. But as you might expect, these memories have stayed in my mind!I'll start by saying I don't hate my dad. We had a good relationship and if he was still alive I wouldn't have shared this story with anyone, even anonymously. My mom and dad had me in their early 30s, and my twin siblings in their mid 30s. However,...
My girlfriend, Tori, caught me cheating and immediately had me feeling like shit. As I already felt depleted physically too, I fell back into the pool. I was down under the water for about thirty seconds. During that time, I felt much better physically. As if I went from massive pain, to none at all in a matter of seconds. I came back up to them both glaring at me on their knees. Tori put her hand out. "I think we need to talk, Eric." We exchanged looks. Her eyebrows were down and her teeth...
TabooIt was a hot summer day in sunny Las Vegas. I was driving back to my house from a hardware store when I saw a car broke down on the side of the road. Normally, I would absolutely stop and help. If you’re able to and don’t, you’re an asshole. I especially wanted to stop when I saw the girl on the sidewalk talking on her phone. I pulled just past the car and parked, and walked towards the car. As I walked up, the girl finished her phone call in anger and stressfully looked at me and with a...
The next morning came late to Madison. She awoke to find her parents gone and a list of things to do every day while she was gone. She got her clothes on and quickly finished her chores. She believed she disserved some free time so she went to ride her horse. Madison's horse was named Shadow because he was mostly black except for a white patch on his nose. As she came to the stable she suddenly became wet. She ignored the thought and continued onward. As she came to Shadows stable she found...
July 1981, Madison, Wisconsin Wednesday morning, after a late night Tuesday driving Joey, I woke up extra early to swim. My little sister joined me and we had our usual breakfast. At 6:30am I left to pick up Bethany, and we started on our way to Madison. I’d decided to take a slightly longer route through Champaign, Illinois, to avoid having to drive through Chicago. We followed I-275 to I-74, which took us to Indianapolis, where we stopped for gas and some coffee. We continued on I-74...