Sex Diaries Stepsister
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October is breast cancer awareness month. With that noble cause in mind I invite you to come along on this whimsical journey during which you will learn how two very lucky guys discover the true magic only Princess Diaries backpacks can possess. The Princess Backpack Diaries By: Simonne Danielle [email protected] © 2010 All Rights Reserved "Now here's a story that ought to put every guy's sense of masculinity to the ultimate test," anchor woman Alycia...
It was a bright sunny day when my Stepmother said we should go for a bike ride like we used to do when we were younger."Really?" I groaned unhappily, because I always hated those bike rides."No it'll be great!" said Hailey eagerly, before looking at me and smiling."Then that settles it!" my stepmother said happily "You guys go get ready, and i'll get your father to load the bikes on the car!"And so quickly Hailey skipped off to her room, where's I trudged off to mine, really not enthusiastic at...
When I was still a k** my father divorced my mother and married another woman called Veronica, she was a beautiful tall woman with long brown hair and clearly loved my father a lot.She also had a daughter from her first marriage called Hailey who looked a lot like her, and was about a year or so older than me, but as we grew up Hailey began to run wild, and eventually they shipped her off to boarding school, and except for holidays, I hardly ever saw her.Then when she turned 18 she finally...
As we sat in the kitchen eating breakfast on that bright summer morning, my stepmother said eagerly "Hey, why don't we all go to the beach today?""Yes!" exclaimed my stepsister eagerly "We haven't been for ages, and I want to work on my tan, before I go off to university!""Yes, why not!" agreed my father, and so as everyone else was eager to go, I said yes as well, and then we headed off to our rooms to get ready.Half an hour later we were in my fathers car heading for the beach, and because it...
The last few weeks have been very interesting. I can't stop thinking about my stepmother. The urges have been unbearable at times. My stepmother and I have not had sex in a few weeks. I constantly jerk off in her panties. I just dream of sucking her nipples. I loved when I fucked her. Her breasts were so firm and didn't even move. My stepmother is a natural size 38D. She’s so experienced and her pussy was just the best thing I ever felt. It really did feel like I was fucking velvet. I just...
TabooSaturday was my big game, the season was over but our team had got to the cup final, and now our little town was going to play in one of the biggest football games we had ever played in, and I was one the key midfielders they were going to rely on.So, Friday night I eat well, had a light run down the park and back, and then got an early night so I would be fresh for the game the next day.However, the next morning I didn't count on my hot brunette stepsister, slipping into my room early to wake...
My father recently married my stepmother. She’s a very sexy looking woman. She tells everybody she's a dancer, but she’s really a stripper. I think that’s where my father found her. She’s my father’s third wife. My father is always getting married. He’s a player and loves to have a sweet piece of ass on his arm. My mother left him years ago, because he couldn't keep his zipper up. He cheated on her with his secretary. My mother had a nervous breakdown and was unable to take care of me. I live...
TabooStepsisterBy Sonya EsperantoStory:FIRST WEEK - Monday Later AfternoonJames was out by the backyard. He was smoking a cigarette, oblivious to the fact that he was being watched!! His backyard faced a cliff, that overlooked the Gulf of Mexico. He lived in a big mansion, on the top of a hill, somewhere off the coast of Miami, Florida. He quickly threw away the cigarette, since he believed his parents would be home any moment!! James ...
Defiled Little Stepsister "You really need to get your act together," Tiffany told herolder stepsister, Kelly. "The people you're hanging out with arenothing more than a****ls, disgusting street thugs. Why are youdoing this to yourself? Don't you want to attend college, meet anice man, settle down and have a family like I'm going to do?"Tiffany continued as she unpacked her clothes from the suitcase. Kelly stared back at her beautiful, younger stepsister withcontempt, but said nothing. ...
Carmelita eyed Mark’s stiff cock with lust. She knew the devilish glint in her dark eyes told him better than words that his new Stepmother was more eat-hungry now than fuck-hungry. She was standing before him, naked from the waist down, baiting him with her cunt, while her wet pink tongue licked still another invitation across her plush red lips. Suddenly her heart was pounding faster when a wicked little smile creased his lips. Without waiting another second, she dropped to her knees...
After having fucked my beautiful stepsister I really didn't know what to say or do for the rest of the day, it was amazing, and I did enjoy it, mainly because she had a beautiful tanned slim body, and her pussy was so wet and warm when it rode my cock, but she was still my stepsister and now I was really confused.Then eventually it was time for dinner, and my stepmother had made a big family meal to celebrate my stepsister coming home, and so I took my seat at the table beside my stepmother and...
I looked up to see Ariel standing in the doorway of my room. Her blonde hair was dropping wet and fell over her shoulders. She had nothing but a green towel wrapped around her. It's been almost two weeks since the night Ariel and I had sex. She had come into my room in the middle of the night during a fierce thunderstorm. Since that night Ariel and I had many wild trysts. Every chance we had we went at it. At times it was difficult with our parents in the house but the taboo and risk of...
It was just a few days before the summer was over and I would be going to college for my first year, and Hailey my stepsister, would be going away to her college as well.Now, my college was just the basic local school for further education, but Hailey was going to a really big posh place in the country, because her real father had gone there, and he was willing to pay for her to go there too, and this also meant she would need a new school uniform."Come on then, young lady!" I heard my...
My Stepmother and stepsister had both just sucked me off until I came in my stepmothers mouth, this was the first time I had done that with my stepmother, and as I lay on my bed staring at her, she sat watching us, as my stepsister Hailey finished sucking my cock back to life, and now I was fully hard again, she stripped off naked and climbed onto the bed.Standing over me, my stepsister with her slim hot naked tanned body, little perky tits and smooth bald pussy grinned down at me, before she...
"Come on see!" cried my stepmother eagerly."See what?" I asked as I walked towards her stood by the backdoor."See what your father has brought me for my birthday!" she replied back grinning excitedly.So I stepped out of the backdoor with her, and there on our back deck was a large grey plastic bathtub."It's a jacuzzi!" exclaimed my stepmother excitedly "I've always wanted one! And now I have!""Great!" I replied less enthusiastic."Oh don't be like, you'll enjoy it when you get in!" my stepmother...
Introduction: Okay I went and rewrote Chapter 9 since I got bad reviews on the previous one. No more parents will be involved, as well as no pregnancies so quit asking for it. Let me know what you think. Read on and enjoy. If youre new to this series, please read the previous chapters first. After Tim walked in on a threeway, lesbian sexfest, mom suddenly had second thoughts, but the younger girls werent done yet, and Tim wanted a little more action too. But his stepsister and her friend may be...
The summer holiday's were about to finish and it was time for my stepsister Hailey to head off to her big posh college, while I stayed at home to go to the local one, but it wasn't just going to be a simple goodbye see you in the holidays with my stepsister, no, she wanted us to travel with her to her new school.So, on the last but one day, before I was a due to start at my college, I climbed into the car with my stepmother ready to drive her the hour or so into the countryside, where her new...
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...
During these weeks I saw less and less of Ryan. He'd show up from time to time to run another ad or to spend the night with me, but it wasn't like it used to be. I was tied up a lot of the time in our bed; usually dressed in lingerie and sometimes simply naked. He'd bind my arms over my head on the bed and do cocaine from different parts of my body. Then he'd lift my legs, exposing my cunt and fuck me. Often after he was done using me he'd leave. I stopped asking where he was going...
I was enjoying a lazy Monday morning in bed, it was the middle of the summer, collage didn't start for another few weeks, and I didn't have a care in the world!Until I realised this happy warm feeling I was experiencing wasn't just my good summer feeling, but something else, something physical in a area lower down on my body, and as I opened my eyes to see what was causing it, I saw to my surprise my slim brunette stepsister lying between my open legs, gripping my morning boner in her soft warm...
Jenna watched her mom leave the room, not noticing how her mom was acting. She quickly sat up, looking at her stepbrother's fat member hanging there. "That means this is all ours now Anna," she exclaimed, wrapping her tiny hand around Tim's shaft. Tim watched his stepmom leave, wondering why she had just suddenly got up and left. It seemed to him that she must be having second thoughts about what she was doing now. Kelly walked back to her room, knowing she should have told Tim to...
Friday evening I didn't have any plans as I made arrangements with Jessica on Thursday to go to a club Saturday night. I relaxed and rested the whole of Friday. My stepsister was first home at about 4 30 from varsity, our mom literally walked in 2 minutes later and a few mins after that our dad. We all greeted each other and then our dad asked Amy and I what our plans for the evening were? I answered first saying that I'm home tonight relaxing as I'm going clubbing tomorrow night. Amy answered...
--- Stepsister Sleepsexing Surprise (MF, inc, nc, oral, impreg?, reluc, safe, viol) by Krosis of the Collective --- I opened my apartment door and let my sister in. As she shuffled past I noticed a bruise under one eye. I didn't ask. She had called me out of the blue a few hours before to ask if she could stay with me for a while, and now I was pretty sure I knew why. Regina (I call her Reg) was a big woman -- not fat, but tall and proportionate -- an Amazon with an hourglass...
After spending a wonderful Thursday by Claire I stayed home the friday with my mom and dad helping prepare Christmas day lunch. Friday went by rather quickly and before I knew it was 9pm and I was already laying in bed chatting to my girlfriend Jessica. I fell asleep while we messaging as I was pretty dead. Waking up Christmas morning I got up and went to wish my family a merry Christmas. We all slowly got up and then had a light breakfast, so the big lunch wouldn't be ruined. After breakfast...
I was 21 when I met Jo – Josephine actually, but she preferred Jo. She was all of 18 and a very spunky girl. She was Fran’s daughter. Fran – my father’s wife. I hadn’t seen her before although Fran and Dad were married for more than four years. Maybe because I was at university and hadn’t come home in a while. But this summer, I saw her. She was a tiny brunette who was interested in astronomy. What I didn’t know was that she was untouched and I discovered about my virgin stepsister soon. We had...
IncestIvana arrived as usual and on time to clean Mrs. K’s house. Mrs. K opened the door with her normal smile but saw that Ivana was looking rather more cross than usual. When Ivana walked into the hallway, and Mrs. K had closed the door, she turned and asked, "Is everything okay, Ivana?”Mrs. K was wearing a floral sleeveless dress with a hem a few inches above her knees. She wasn’t plump but wasn’t slim either, and Ivana thought that she looked lovely in her dress. Ivana was wearing a...
SpankingThere I was laying on my bed, remembering having shared the first dance at prom with my beautiful, gorgeous, blonde stepsister. She was a super brain all her life, won scholarships and excelled at everything she focused on. She was also a stunning demure fox! I would have done and still will do anything for her. This is a brief story of how I was imprinted into love for my stepsister, Shelley. Ever since she walked in on me by accident, into my bedroom, and saw me sitting on my bed with my...
Taboo------------ Aaron Sanders was shocked when he heard that his father had remarried. His mother had died when he was young, and it had always just been him and his dad. When he was going to college at Pitt, his father told him during his senior year that he was dating a woman, but getting married only three months into their relationship was a huge shock. Heather was a woman who had been divorced a long time and he guessed they just fell into a mindset of hurrying up because they were both...
Jenna slowly walked into the room, looking at her mom laid out on the bed, Kelly's lingerie messed up a little, but still on and covering her. Jenna walked in front of them, looking down at her mom's still gaping pussy, Tim's cum clearly visible yet. She looked over at Tim, his limp dick laying in front of him, as he laid on his side, the remnants of the condom still on his dick. Jenna shook her head slowly, "no wonder why you wanted me to leave, and you let him shoot inside of...
Introduction: This is my first attempt at posting a story, and this is one that really happened between me and my little stepsister. It takes a while to get going, but bear with me. I would love to hear your critiques, criticisms, and suggestions, but please remember that this is my first try. I have more of this story waiting to be posted, and believe me, it gets fun and exciting, but first I want to see what kind of reaction Part 1 gets. A summer with my Stepsister Mary, Part 1 This is a...
Christine and Jack had been trying to up one another for weeks now, each turn becoming more depraved and twisted. Christine knew she had to do something to finally end the war between them.She had concocted a plan with several of her girlfriends to put Jack in his place, force him to admit defeat so they could move on with their lives.It all began the night before, where Christine had sat down with Jack and spoke about all that had happened and asked to call a truce between them. Their parents...
TabooA while after watching my stepsister play with her cunt in her bed, I found myself chatting to her one afternoon while we were home alone. Our parents were out at a show and her and I were having a drink together. Our conversation soon went sexual for some reason and we both felt rather comfortable with each other to talk about our sexual experiences. She soon asked me if I have any fetishes and I replied yes and asked if she had any. She to said she does and asked if I could tell her mine...
Aaron Sanders was shocked when he heard that his father had remarried. His mother had died when he was young, and it had always just been him and his dad. When he was going to college at Pitt, his father told him during his senior year that he was dating a woman, but getting married only three months into their relationship was a huge shock. Heather was a woman who had been divorced a long time and he guessed they just fell into a mindset of hurrying up because they were both in their forties....
Aaron Sanders was shocked when he heard that his father had remarried. His mother had died when he was young, and it had always just been him and his dad. When he was going to college at Pitt, his father told him during his senior year that he was dating a woman, but getting married only three months into their relationship was a huge shock. Heather was a woman who had been divorced a long time and he guessed they just fell into a mindset of hurrying up because they were both in their forties....
The morning after our first sexual encounter, Lisa went to visit her friend Hailey, who lived in the next town over. She stayed the night, hence we hadn’t talked very much apart from a goodbye when she left. Trying not to alert any of our family members, she tried to act normal. I could tell she didn’t know how to behave around me though. She seemed afraid to look me in the eye, but had a shy smile on her face anyways. It was starting to get dark when she returned, going straight to...
Hi, i'm mark . A normal teen boy with the usual teen interests. I'm about 1,8m tall, weigh about 75kg, blue eyes, dark brown hair. I'm no superman, but keep myself in decent shape.I have a stepsister, Lisa who is 18. She is tall, slim, with long light brown hair, and beautiful C cup breasts and a nice round butt. I always sneak a peek at her whenever i can get a look at her body. But never actually thought about having sex with her, until tonight that is.We were very close, and had quickly...
Aaron Sanders was shocked when he heard that his father had remarried. His mother had died when he was young, and it had always just been him and his dad. When he was going to college at Pitt, his father told him during his senior year that he was dating a woman, but getting married only three months into their relationship was a huge shock. Heather was a woman who had been divorced a long time and he guessed they just fell into a mindset of hurrying up because they were both in their forties....
IncestTim is your typical 17 year old high school boy. He plays football, basketball, and runs track. He stands 6'1" with dark brown hair and hazel eyes, weighing about 180 lbs. He lives with his dad as well as his stepmom and stepsister. His dad had married his stepmom, Kelly, about 6 years ago, after Tim's mom had left them when Tim was 7. He gets along with them alright, fighting with his stepsister, Jenna, every once in a while, like any normal siblings.Jenna is 14, standing about 5'4", with long...
The vulnerability of my stepmother aroused me first, a primitive biological urge harkening back to the plains of the Great Rift Valley when our ancestors slept in trees and sowed their seed whenever and with whomever they could in the survival of the fittest or, in my case, the most voyeuristically surreptitious. Add the sibling rivalry of a brother with his stepsister and color it with the twisted desire of i****t, one of the biggest taboos of our culture, a taboo so tempting that it is...
Aaron Sanders was shocked when he heard that his father had remarried. His mother had died when he was young, and it had always just been him and his dad. When he was going to college at Pitt, his father told him during his senior year that he was dating a woman, but getting married only three months into their relationship was a huge shock. Heather was a woman who had been divorced a long time and he guessed they just fell into a mindset of hurrying up because they were both in their forties....
Sorry a little late writing a another chapter about my ex girlfriends cock teasing stepsister ( Cheryl) and how we ended up fucking. Now on to the story. Well as you probably know if you read my first post on her that Cheryl had been teasing me for sometime and we ended up finally fucking. Well Cheryl and myself have been fucking for a good 6 months up to this point and it was the best 6 months a guy could ask for. Cheryl would be waiting for me to get home from work at times and we would...
A note to readers - keep in mind that I never had a plan for these diaries. I'm only sharing them with the world because I can now handle the reflection that comes with reading them. As a result, they don't fit into chapter form all that well and at certain spots things skip ahead if I wasn't writing much at that time or had little to say in my entries. I have tried to find logical breaks to fit into a chapter format for this medium. Hopefully it is working for you and you are able...
Mom walks through the front door to a house that is more like a small cottage like she has lived here forever. We are greeted by a girl, she looks like she is the same age as me but that is where the similarities end, she has long wavy naturally blonde hair, bright blue eyes, tanned skin that looks natural and not like it has been sprayed on and a body that any girl would kill for, she is tall and skinny with long legs, a flat stomach, a cute round face with a large smile and what look like D...
I am home on leave after basic training, AIT, Airborne, Air Assault, and Pathfinder schools, and getting ready to ship out to my first duty assignment overseas. I had been back home for about two or three days at this point, and she (Stepsister) got into a big fight with her current boyfriend/whatever he was and needed to get some of her stuff out his place to take to her new apartment Mom and Dad helped her rent for her Senior year at college so she did not have to stay at the dorm. I of...
Valarie, or Val as I called her, had been my stepsister since I was ten and she was thirteen. We got along like most siblings, playing together when the mood dictated and staying out of each other’s way when need be.Things started to change around the time she turned eighteen, though. Most of the guys in my school had no problem telling me how hot my stepsister was, which I’d tried to avoid thinking about, despite the fact I had noticed the great changes to her body over the years. Val always...
Taboo“Kevin. Are you there?” my mom asked, sobbing still somewhat evident. “Yeah. I’m just surprised by the news. I’ll be home as soon as possible.” I hung up the phone, and looked at the clock. It read 10:23. “So what was that about?” Amanda asked. “It was my mom. Alyssa ran away.” Amanda went into complete shock. “You…you sure?” “Would I be lying about something like this?” “No one that’s sane would lie about something like this.” “Listen. I don’t want to leave you here, but I have to...
This is a true story that happened between my stepsister Mary and I. My name is Bobby, and I was 15 and she was 13 when all of this happened. I had just had to move in with my dad at the end of the school year to a small town about an hour away from where I had been living with my mom because she was going to be working on the other side of the country for the summer. I was pretty pissed off with the whole situation because I wasn’t going to be able to see any of my friends all summer, I...
I got up and showered to ready myself for another day of relaxation. As I got out of the shower and toweled myself dry, I glanced out the bathroom window overlooking the back deck and saw that I was not alone. My stepsister, Christine, was walking through the back yard, onto the deck. She was staying with us for a couple of weeks until she could move into her new apartment. She was wearing running shorts, a white t-shirt, sunglasses, and a baseball-style cap. Seemed she was coming back from a...
A true story about a friend’s stepsisterA true story about something that happened to me when I was a kid – it never left me and girls being stripped or stripping in front of others, particularly when they don’t really want to, still colours lots of my stories today. The summer of 1973 I turned . Up until the July of that year I’d never seen a girl naked in real life. I’d kissed a few girls’ of my own age and managed to touch a few boobs but nothing more than that. One of the boys in our gang,...
by Vanessa Evans Part 02 I was convinced that I was having a wet dream but woke up to find Eva sucking my shrinking cock. “I hope that you don’t mind Luke, but you were all hard and I couldn’t resist sucking you and you gave me your sperm in my mouth again. Why were you hard when you were asleep?” “It’s called a ‘Morning Woody’ Eva. I have no idea why but lots of men wake up with a hard-on. Maybe it’s the men dreaming about you being in bed with them.” “Do men really dream about girls,...
Chapter 1: Intro When my Mother passed away 6 years ago after a prolonged struggle with cancer, my Dad was crushed by the loss. I didn't think he would ever get over it. Eventually however, he did, and he ended up marrying a wonderful lady who lived in his condo in Miami Beach. My Dad was 62 at the time, and Eloise was 60. I credit her with saving his life. In addition to a new step-mother, I also gained two step-sisters and their families, who I met for the first time at the wedding. The...
It had been nearly two years since I'd left, going straight into the service out of high school. It felt good to be home again, though it was still going to feel different even then. For one, dad had died the year I had graduated. That alone had made my leaving all the harder on mom, but she at least had a sister she was very close to, who had seen her through much of that difficult time. Though she lived an hour away from where we did, mom never failed to at least travel to see her once a...
Diary Entry: September 2008 What the hell is going on here? Ryan and I both slept in and when we woke up I wasn't exactly sure what to do or say. All he said was, "crazy night, last night." I don't really understand everything that happened. I feel terrible that it did and yet, I don't feel like I did anything wrong. It's not like I wanted this to happen. I was just doing what he told me. I feel dirty. I can still feel Tom's cock inside me, still feel his cum. I don't want...
The Dogging Diaries Diary Entry: July, 2009 "Guys, guys, guys! Settle down. This girl will open her legs for the whole room. As long as you're treating her well and keeping her as the center of attention, she's yours to do with as you please. Just make sure you don't treat her too well." The room laughed. "You can fuck her, cum on her, cum in her, slap her, spank her, she's fucking hot and she will go all night if you can." I could hear Ryan getting the crowd of guys...
Third in a series of reader questions with Alexandra Moore, author of The Dogging Diaries: Q. You seem to have quite a fashion sense when you were dressing to play. You were pretty detailed with what you wore for the events mentioned. Surely there must have been more about your thoughts on sexy fashion. Your fashion ideas may be valuable to other t-girls. Can you share your recommendations on what worked (clothes, makeup, shoes) for you? A. Great question. How much time do you...
Since Christine had first began this little game of 'tit-for-tat' between her and stepbrother Jack, starting with her forcing herself on him in order to make him fuck her.Then in return, Jack got his revenge when he forced Christine to be his little slut and do as he wanted; fully complying to his every demand.Christine returned home after high school with one of her best friends, Sara. She was pretty; long slender legs with hips that shook with every stride she walked and large breasts.Jack...
TabooThe Dogging Diaries Diary Entry: July, 2009 "Guys, guys, guys! Settle down. Now listen. This girl will open her legs for the whole room, so you're all getting laid tonight. As long as you're treating her well and keeping her as the center of attention, she's all yours to do with as you please. Just make sure you don't treat her too well." The room laughed. "You can fuck her, cum on her, cum in her, slap her, spank her, she's fucking hot and she will go all night if you...
Part 2 of a series of questions and answers with Alexandra Moore, author of The Dogging Diaries. These questions cover parts 3 and 4 of the diaries. Again, thanks to Matt for putting the questions together. Away we go ... 1. You obviously had some deep struggles. How close did you come in 2007 to giving the dream of being a girl? How were you able to get past the stress and doubt? Do you have any recommendations for those who might be in that situation now? The answer lies...