Checkmate
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BBW 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....
IncestScott'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...
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....
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....
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....
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...
IncestWhen I arrived home, I noticed that Cassandra’s car was parked in the driveway, which was odd because she typically worked until late in the evening. It was only 2:00 in the afternoon. I sat in my car for a few minutes, unsure, before I finally made my way to the front steps of my stepmom’s house. As I peered through the living room window, I spotted my stepmother dancing by the stereo and really getting into it. The mushy, lazy sounds of Jack Johnson wafted from the speakers. She never...
Hello, 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...
IncestIt 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...
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...
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...
IncestTrue 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"...
Inspired by this post by chrisffn099 https://xhamster.com/posts/845238 My first job after school was in an office where an older guy took a wee fancy to me. Everyone knew he was gay but he was never a pushy or creepy type so, I was happy for us to go out sometimes together for the day on business or hang out with him at times on office nights out. He always asked me if I was going out with someone even though he knew I was single. Looking back, although I had no thoughts about him sexually at...
“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...
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...
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...
InterracialSharon stood out the front of the large sandstone Rose Bay home and slowly unfolded the piece of paper in her hand. She checked the number against those written on the oil stained page that had been torn hastily from a notepad and handed to her three weeks earlier. With a wave over her shoulder the taxi driver pulled away, leaving her alone to begin the second stage of her burgeoning sexual development. The Sydney sunset reflected off the stain glass windows and although expecting to hear music...
“Bugger,” Sharon tilted her laptop backwards and checked underneath, half expecting to see its innards hanging out. “Piece of shit computer.”Marcus finished chopping the onions and through teary eyes checked out the computer.“What did it do?” he asked. “Did any message pop up?”“Nothing,” she said and forlornly pressed the power button. “And yes it’s fully charged.”She mashed at the keyboard before slamming down the lid and pushing it across the kitchen bench.“Why do they always shit themselves...
Caught Crossdressing by Aunt Sharon Story by Kresha Matay "I wonder where Brad is? He knows you're coming, you'd think he'd stick around. Oh, I hope he'll turn up soon, otherwise you'll have to drive back in the dark." "Rita, don't worry about the boy so much. Brad is like every other sixteen year old boy. He's probably driving around with his friends looking for girls and forgot I was coming!" "Well, aah, I don't think so!" His mother stumbled to say. "That's something you and I...
Dorothy asked him what he found so funny. “Is that Sam Andrews?” “Why yes it is. He was convicted of embezzling from his employer and spent a couple of years behind bars. He lost his job, his house, and his wife left him. Poor thing.” Bill thought about saying something to Sam but then decided that it would be pointless. While they waited for the check, Karen and Sharon went to the gift shop to look at baubles. Even though Cory had been going to visit Mrs. Johnstone regularly since Bill...
Sharon flipped the phone onto her bed and turned to the hotel window. Two nights in Melbourne and apart from a few of her colleagues, she knew no one. Twelve stories below, the good people of the city shuffled home. Her phone beeped once more alerting her to a message from her husband Marcus.‘Go ahead’, the message read, ‘I told you to cut loose without me.’Sharon always loved playing with Marcus there, it gave her safety and security. ‘I sent you Mark’s contact details, call him,’Sharon...
Sharon got to the gym very late that night. In fact, it was closed. However being the "Queen of the Gym" had its advantages so she let herself in with her key. The owner, Steve, liked her very much and enjoyed having a world class female bodybuilder around. He thought it was good for business and most of the men at the gym loved having a "big girl" that could keep up with them and she often outclassed them. Sharon loved showing up the muscle studs and undoubtedly had the strongest legs of...
Francis threw open the door and said sternly to Daniel “it is unacceptable, you just forgot, so you are so going to get a spanking.” Daniel looked up and immediately knew what she meant. Francis, his fiancé, asked him to take her library book back whilst she was at the shop. It was the last day so now she gets a fine and had made it clear, like very clear indeed, that she would put him across her lap if he forgot. Well, he did forget as he got engrossed in a game of cards with Francis’s...
SpankingIt was a warm evening, around 7PM. Sharon Fox was watching television with the lights off. Life was depressing. She had been jobless for six months now and had to borrow money to support herself and her 15 year old son Josh. Her son was over at someone else's house. What made her more depressed was that she was now living at the time of peak oil. Deep down she knew it just wasn't going to be bad for just her and her son, but for the entire country. She knew that many people won't have...
Jorge rang the bell at eleven-thirty on the dot. Sharon let him hand her into the limo and settled back to shake as the car moved smoothly through the traffic. What was Armand up to? Nora seemed to think he had some master plan -- no doubt with some reason, although she apparently wasn't at liberty to share... Sharon had NO idea, but things had been escalating steadily since the previous weekend, so there was no telling... Nora's introduction to sex had somehow upset the equilibrium they...
It was a bit after ten p.m.; the Wench moved quietly along the north hallway headed for her Mistress' rooms. Sharon as going to have to learn -- but she wouldn't, apparently; she'd had all the time in the world to, but she bucked Master at every turn. And he liked it that way, too, apparently... The Wench shook her head. Passing Nora's rooms she picked up a set of sounds that were indistinct, but identifiable, nonetheless. Well, she was a few minutes early... The main door to the suite...
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...
Taboo"Bugger," Sharon tilted her laptop backwards and checked underneath, half expecting to see its innards hanging out. "Piece of shit computer." Marcus finished chopping the onions and through teary eyes checked out the computer. "What did it do?" he asked. "Did any message pop up?" "Nothing," she said and forlornly pressed the power button. "And yes it's fully charged." She mashed at the keyboard before slamming down the lid and pushing it across the kitchen bench. "Why do...
Previously, I had met Sharon, a gorgeous sexy blonde older married woman during my mid-twenties at a barbeque. We had chatted, flirted, and danced together.I had given her my number, and two weeks later we went for a drink. Afterwards, I had given her a lift home. She had told me to pull over before getting her back to her husband, to give me an amazing blowjob in the back seat.A week later we met again, and again got a blowjob in the back seat of my car.Over a week after that I finally got her...
Wife LoversSHARON by Leigh DeSantaFe David Hausman sat in the bathtub in a soaking stupor, clouds of dissipating suds popping softly around his knees. His mind wandered out to the bedroom where he had laid out his clothes for the evening. He was fixated on the shiny new French maid's outfit with tulle petticoats that he received at his P.O. box two weeks before. It had remained virginal for those two tremulous weeks because of scheduling conflicts. His second wife, Sharon, though...
"You know what would be a great idea, we should invite the whole family to your next birthday. It's a long time since we had a real family party, would be great to see them again, don't you think" Phil asked. "Mmm" Sharon answered, her mouth full of Phil's cock. They were in their bedroom, they were watching a porn movie together and after having played with each other for a while, Phil ordered Tits to suck him off. She was naked, her big breasts pressing against Phil's stomach as she sucked...
Christine had invited her friend for a sleep over knowing full well that I had the hots for her, just one look at her firm 40inch chest could reduce me to a wreck. Christine breasts were a nice size considering her slim frame about 36c if I recall set off with a delicate candy pink nipple that was to die for. I had an idea that Christine was trying her best to match me up with her mate Sharon and I did not plan on this. Whilst watching the video the two girls were doing there best to...
In my mid-twenties, I was a single guy. I had a few previous girlfriends and a few more one-night stands. Those girls had been of around the same age as me or younger. I had never been with anyone older than myself.One summer I went to a barbeque some of my older cousins were having at my uncle’s house. It was a sunny warm day, everyone out in the garden enjoying themselves drinking etc. There were a lot of people there I didn’t know, friends and work colleagues of my cousins.I noticed one...
Wife LoversFor years Sharon had been on the receiving end of corporal punishment.She could never settle at school and very often found herself before the Head Nun or the visiting Abbot and having her bottom spanked. Now aged 40 she felt an urge to attend the Monastery of Repentance every now again to receive a spanking by way of chastisement and to help her cope with the day to day pressure in her life.She had been told that confession and spanking were very the****utic and she believed they were,having a...
When I think back and recall all the trouble I went through to seduce and take Sharon, my neighbor Jerry’s wife, to bed, I shake my head and wonder how blind I was not to see the big picture. Not that I did not enjoy making love to Sharon. I still do, in spite of everything that happened since that first time and the whole scene, blurred in the beginning, came into focus with a bang, literally, one sunny afternoon. But I must first write about the seduction, of which I am quite proud of before...
Group SexAfter Karen joined the family, Sharon's sexual services were even more in demand than before. She really liked the young woman and Karen was only happy to use her every way she could think of.Sharon always had a submissive streak in her personality, but it was never explored in full before now. She was satisfied when someone took the decisions in her life, also of course in her sex life. When they were younger, Phil often dared her to try new things, things that she secretly dreamed of, but...
Sharon and Marcia - by: Marcia Spencer It was the third time that Mark had seen her at Sears. She was striking, just slightly taller than the average young woman, with her hair cut in a short style. She wore more makeup than he liked, but it seemed consistent with a certain air of attentiveness, maybe even of strong-mindedness that seemed her most outstanding characteristic. Obviously, her normal duties were in the lingerie department. It was his third stop at the Mesquite,...
When I pulled out of the driveway that morning, I didn't know where I was going. Sharon had so destroyed my thinking process I couldn't think straight at all. Her revenge had been totally a surprise and complete in its effectiveness. I knew that she would have done what she did only if she was planning on leaving me. I had packed my things in a hurry and when I left the house I heard her running to the front door. I didn't look back as I fired up the car and pulled out. The last thing I...
Previously, I had met Sharon, a gorgeous sexy blonde older married woman during my mid-twenties at a barbeque. We had chatted, flirted, and danced together.I had given her my number, and two weeks later we went for a drink. Afterwards, I had given her a lift home. She had told me to pull over before getting her back to her husband, to give me an amazing blowjob in the back seat.A week later we met again, and again got a blowjob in the back seat of my car.Over a week after that I finally got her...
Wife LoversWhen my wife wants something, I can sometimes find it impossible to refuse her. We'd just got back from a weekend away where we'd met some friends and swapped partners. I'd always suspected that my wife, and mother of two children, was a whole lot hornier than most women. She was kneeling on the bed wearing nothing but a smile and casually stroking my cock to hardness when she asked me the question. "Do you know Lisa from work?" I had never met Lisa but had heard all about her break up...
Exposing a very young "Sharon with Tits out"by magichands©I was very young, fresh out of high school, barely 18 when my Dad sat me down for a talk."Well, Son, it's time you got a job, get married, and settle down!""YIKES!" I thought, I had just taken off my cap and gown less that a day before, it was summertime, and I had planned on doing a bit of playing.My Dad was from the old school, once the Son was grown, it was pretty much out the door! "You can stay here for a few months, but here is...
You will recall that Sharon was screwed by my friend, at a Christmas fancy dress party in our flat. Well, Christmas had come and gone and Sharon had made a good start into becoming a slut. We spent many a night in bed talking about her sailor friend at the Christmas party. I always brought it up as we fucked. I kept telling her she was brilliant and that I was so proud of her. When we were fucking, I would bite her lip to remind her of him and play hard with her nipples. I knew this was really...
OutdoorAll sorts of thoughts were running through my head. I also, thought about her massage every day last week. After a few seconds, I said, "Certainly, I have Saturday free and will be more than happy to give your mother a special ‘birthday massage’. What about your massage? You missed yours last week." Sharon replied,” If I wake up before noon, I would love to get a massage." I said, "O. K. have a good time Friday night and I'll see you Saturday." I couldn’t believe how fast Saturday...
Matt and Jareth were skipping school to hang out at the arcade. They were seniors three weeks from graduation so they figured it wouldn’t matter. Jareth elbowed Matt. “Dude, check out the hottie on the Dr. Chomps machine!” He gestured in the woman’s direction with his chin. “Dude, you made me lose my last life!” Matt complained as his spaceship exploded. He turned to look where Jareth was pointing. “Holy shit.” She was tall, with broad hips and a big, round ass stuffed into capri-cut jeans...
TranssexualHi, people. My name is Jyoti, and I am from Goa. I am 21 years old. This is a year-old incident about exploring sex that I have written down. My college informed me to find an ex-student and interview that person’s experience about this college and how it shaped their career. Luckily my mom knew a lady who lived a floor above us in the building. I wasn’t very happy about it, thinking that lady would be of my mom’s age. The entire thing would be boring. It was a time when I was very irritated,...
LesbianHi, people. My name is Jyoti, and I am from Goa. I am 21 years old. This is a year-old incident about exploring sex that I have written down. My college informed me to find an ex-student and interview that person’s experience about this college and how it shaped their career. Luckily my mom knew a lady who lived a floor above us in the building. I wasn’t very happy about it, thinking that lady would be of my mom’s age. The entire thing would be boring. It was a time when I was very irritated,...
LesbianTo no surprise, Vance immediately nodded frequently. He shook around and even began jumping up and down a little bit also. He seemed like an energetic dog, and we just came back from wherever.Before he could even calm himself down, Sharon leaned down to my pussy with her tongue out and began fucking me. Her tongue instantly began slathering my lips with quick and frequent licks right on top of them.I felt nearly caught off guard, but so incredibly happy about this turn of events. I looked...
Threesomes“Oh, that black horse is lovely!” Sharon cried. “Can I ride him, Aunt Pearl?” Pearl glanced sideways at her niece. She had been surprised and pleased at how nubile the girl had become since she’d seen her last. There was something about nubile young girls that Aunt Pearl always found very interesting. The horse was a brawny brute, his sleek coat jet black, his main flowing and his tail silken. He eyed the girl and his dark, moist lips curled out from his big, blunt...
First let me tell you a little about myself. I am 37, long black hair to my ass, hazel eyes, 5 foot 7 inches tall and I weigh right at 135 lbs. My breasts are slappy, or so I’m told anyway, perfect aureoles that I find pleasant to look at. I have a models build and am considered beautiful by most men and quite a few ladies…giggling! I could probably have any man, or woman, I wanted if I played my cards right, but, it wasn’t a person I wanted at that stage of my life, it was a horse! This...
Sharon Stits and Nikki Summers were two mid-level executives in a large PR firm who were locked in a fierce rivalry from which only one woman would emerge victorious. Brunette, gorgeous, and in their early fourties, both women were on a collision course for the top of the corporate ladder.Sharon had a reputation for wielding her incredible sexuality as a weapon against rival women who got in her way. With her firm 36C tits and long, exquisite legs, which were always dressed in short, tight...