Sassy Cassy
- 1 year ago
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Ever since I had found copies of Penthouse Letters in my older brother's room I had been curious. There were stories of men with other men there and while at first I was a bit shocked that a publication like this would have letters about gay or bi men, soon I began to realize that on one level or another they were more interesting. Perhaps it was the fact that society seemed so down on men being with men, but whatever it was I searched out those stories. I even found myself thinking of being...
Yet, eventually that wasn't enough for me. I craved Mike's cock in my mouth, I craved his cum gliding down my throat.So, after swallowing his load one Sunday I casually said, "You know if you ever need to deposit a load any other time just let me know.""Good to know," he nodded, as he returned his attention to the game.I figured he was just happy with the weekly blow jobs, but a few days later he texted me: Come to my garage. I need help with an oil change.I laughed at his sly wording in case...
The building was a made of cinder block that had been painted several times, though not anytime recently. All of the layers of paint were worn and blistered and it would be possible for some individual with nothing better to do to count the layers. The last painting was two-tone with light blue on the bottom and then at the height of five feet the paint was white. There was an aluminum storefront window facing the residential street that had been installed during some iteration before this one....
I'm married, "straight," and your typical suburban family guy. So is my neighbor buddy. The bonus with this neighbor, he has a big cock and is now feeding it to me regularly.Jeff, my neighbor down the street, is in his mid fifties, just a couple of years older than me, has a lovely wife and two k**s in high school. Both my k**s are in college and my wife is back at work as a lawyer after being a home mom for 20+ years. I'd known Jeff for years, with the families often doing BBQs together, going...
Even though my new roommate was straight, he never had any problem with me being gay. In fact, from the start I think he was intrigued by it. More and more he was hanging out with my gay friends and acting totally comfortable among them, unlike many other straights guys I've known. Brian was a freshman and was assigned as my roommate after my old one dropped out of school. So he was impressionable, as he found himself spending time with me and my buddies, an older crowd.One night I came back to...
I always dreaded my office's annual work trip. A whole ten days dedicated to trainings and lectures with the other members of management. A small upside was that it meant a week away from the hassles of my k**s and wife. My wife and I got married right out of college and had k**s immediately. Now we were in our mid-thirties and it was nice to get away every once in awhile. I would never cheat on her but I felt there was no harm in hitting the strip clubs with a couple of the other guys and...
For many years, the thought had crossed my mind about being gay. I had thought about it whilst playing with myself but could never get the courage up to try it. That added to the fact that I just didn’t find most men attractive. Very occasionally I would see a guy and think, maybe?I had dressed up in lingerie for a long time and had only once put some makeup on. The fear of being caught was just too much. I had also tried swallowing, but I hadn’t liked it and thought that I never would. For...
Gay MaleWhat the hell am I doing? A couple hours ago I was just going out for a drink and now I am driving in my car following a guy to his house. I am a married man, 57 years old and as straight as they come. My hands are sweating, I can feel my heart pounding and I am as scared and nervous as I have ever been. It is like the first time I felt up my date when I was 16 years old in high school. Excited, yet scared to death.I have been married for 30 years to a gorgeous woman and we have a great sex...
Cassia III By: Ryker Several months later, the changes to my body were progressing. When I looked in the mirror I saw more female than male, and my emotions were a mess. No one looking at me would ever think I was a man without looking between my legs, especially with the "all natural" D-cup breasts hanging from my chest. Now it was confirmed my balls and cock have shrunk, just a little bit. I cried myself to sleep the first few nights after I realized it, and Cassia even comforted...
Cassia IV By: Ryker As time went by, I'm not sure how long, but it was several more months, the changes to my body were slowing down. My breasts were a large D-cup or maybe a small DD, and my penis and testicles only shrunk a little more. It was still hard to accept it. Miss Cassia said her treatment was nearly complete, and I was nearing the final stages. Unfortunately, I was still settling into my new emotions, and it was still very hard to handle. I cried often, sometimes for...
Cassia II By: Ryker ___ When I woke up the next day, the first thing I noticed was that the pain still burned in my ass. I looked around and saw that Cassia was gone, but the lights on the metal ring around were out, and a handwritten note was sitting on the floor beside me. It read, "You are late. I will forgive you this one time since I don't need you this morning, but from now on you will wake by 7 am to start your duties. Go downstairs and get ready just like yesterday -...
(Outside The Tiber Hideout) John's Horse Laid Dead beneath his Arrow-Ridden Body, but Still He Clung to Life, His Belief in the Creed in the Assassins Brotherhood Unbroken and Unbeaten, He Crawled through the streets, bloodstained Robes and Stab wounds all red and bleeding red. He Finally Collapsed in front of the Tiber Bridge. (Inside the Tiber Hideout) John Awoke to A Sweet singing, he tried getting up, but he felt several Stitches Pull and the Pain Causes him to groan and pass out. John had...
I mean, I never imagined I would ACTUALLY suck a cock.Although I would be lying if I said the idea hadn't become a growing curiosity fantasy over the past few months leading up to the 'incident'.I mean, I was, and still am, happily married, although our once wild sex life had dwindled to once, maybe twice a month, sex. And not the wild in public, or marathon sex sessions of our younger days, either... usually missionary, with maybe thirty seconds of head if I was lucky.I'm not defending what...
It was Scott's birthday and I had surprises in mind for him. Last night my husband and I had arrived at this luxurious desert spa near Miami and I had a whole day of treats planned for him today. First we'd have a special caviar breakfast and take a quick swim, and then, for later in the afternoon, I had arranged for a masseur to come up to the room. I had requested a specific special masseur, and not another or a masseuse, because that masseur, I hoped, was going to be a big part of the very...
Cassia V By: Ryker Two weeks later, I could tell Miss Cassia was getting ready for something to happen. Part of me was concerned, and I wanted to ask her, but when I broached the subject, she told me not to worry about it. She was already annoyed with me from when I previously begged her to let me cum. When I grew more concerned, I asked again. "Damn it, Marisa! Do you only think about yourself!?" she yelled at me. She started using my name more often instead of "sissy" except...
Cassia I By: Ryker "Aww, don't feel too bad, sweetheart. Most men don't realize what I have hidden in my panties until it is too late for them." "MMPPHH!" I screamed into my gag as I struggled against the cuffs binding my legs and arms. She ignored me and continued. "Still, I overpowered you quite easily. You really are a pathetic wimp, and now you are going to pay the consequences for that." So let me tell you how this is going to work. By day, you will be my live-in maid...
"I said," there was a look in his eyes that terrified me as he spoke – my father had the same look when he was angry – "if you leave like this, then the next time won't be as..." I'd shut the door and started the engine and couldn't make out exactly what he said, but I think he said "gentle." The next time won't be gentle because he's pissed at me? Fuck him, there's not going to be a next time, and out of anger on my part, I flipped him off as I backed out and drove away. Then I noticed my...
Looking back over the last few months, I never would have imagined myself in this position. I have a steady girlfriend I have been seeing since college. I have a good paying job in spite of the recession we have all been dealing with over the last year. And I consider myself better than average when it comes to my social life. While I've dated quite a few women over the years, I've pretty much been going steady with Sandy since we both graduated from Duke a few years ago.Sandy is a...
I am a happy married man. I know a lot of gay sex stories start out like that but I really was in a happy marriage. My wife and I had be together for 6 years and we have two great k**s. I have never had thoughts of sex with men. Physically I am an average 34 year old middle class white collar guy. I have a thin build and I'm about 5'11." I have never been in a fight in my life and I have not been exposed to a lot of riffraff. I guess hindsight is 20/20, I can see where I could have avoided one...
I love cock.I love everything about it.The variety of shapes. The upward curve that often makes me gag even on a smaller cock. The downward curve that slides into my mouth so smoothly.The variety of lengths. Most cocks are five inches, give or take. Yet some are smaller... a four-inch cock is easy to suck without effort. A ten-inch snake is a massive task.The variety of thicknesses. Some are almost pencil thin and feel like sucking a blood-warm milkshake through a straw, while others are so...
Hi to all the fan of ISS..I have been reading these stories ever since I started using internet. I would appreciate it if the ladies send their comments at Though I have been reading these stories for over 9 years now..I am writing a story for the first time. Firstly about myself….I am Rahul Mittal, 25 year unmarried guy with unusual sexual appetite..I masturbate twice or thrice everyday sometimes even 5-6 times especially on Sundays…I am 5’6” weatish complexion, slim built…I belong to a well...
IncestI'm a curious cocksucker and I dream about sucking dick way more than I ever actually do it. I'm divorced (from a women) in my mid forties with a good job and two k**s in college. That's why I'm deeply hidden in the closet and very skittish about letting the cocksucker in me out. But the longer I go between sessions and the more big dicks I goon over on the internet, the hornier I get till I'm ready to do anything for my next taste of cock, and of course cum.It had been several months since I'd...
I was very frustrated and horny as hell as I boarded the car train in Sanford, Florida heading to Charlotte, North Carolina. My car was on board as I was going to be staying in Charlotte for at least three months. The Company I worked for was sending me to our Charlotte branch to oversee the start up of a new computer system that I had help develop over the past year.My frustration stemmed from the fact that my wife was not going and would probably be fucking our good friend Charlie's brains...
I was very frustrated and horny as hell as I boarded the car train in Sanford, Florida heading to Charlotte, North Carolina. My car was on board as I was going to be staying in Charlotte for at least three months. The Company I worked for was sending me to our Charlotte branch to oversee the start up of a new computer system that I had help develop over the past year.My frustration stemmed from the fact that my wife was not going and would probably be fucking our good friend Charlie's brains...
"That was unfucking believable" Jake exclaimed as I finally let his deflated cock slip out of my mouth. He tapped his phone screen and set it on my desk. Then he scanned the floor, looking for his shorts. "How long have you been sucking cock?"I smiled and snorted "Dude, seriously, you're my first. I had fantasized many times but your cock was the first to enter my mouth." "Leave your shorts off." I ordered and surprised myself by adding "I think I might want to suck you again.""No dude. I'm...
Sometimes finding what you thought you wanted turns into a whole lot more. I had finally found a masculine dominant man in the area who needed regular service. I was happy. We would email, or text, and set up times that would fit each others schedules (he is married, i have a gf). We would meet, he'd stick his cock in my throat and call me names until he shot his sticky load on my face and sent me on my way. It was great. It got better.I got a text sunday afternoon. "Go to my house.""When...
I was a 52-year-old happily married father when my world turned upside down in an instant. My wife and I had been planning a vacation for several months with my 17-year-old daughter. We were going to spend 16 days with her parents in the Bahamas, fishing, skiing and hanging on the beach. We were leaving on Friday evening returning 2 weeks later, on Sunday. It was going to be the longest vacation I had ever taken. I am a National Sales Manager for a large company and was never willing to take...
Cassi and I had anal sex once before when we first started dating. But after the first time we didn't really do it or chat much about it for a while. Then the night after movies we chatted a lot about it and eventually with a bit of help from my stepsister we managed to have some alone time together at my parents house.Cassi and I rather quickly made our way to the bedroom where we undress each other. Once naked I laid her down on her back and made my way to between her legs. I started muffing...
The next morning I woke up totally refreshed. I lay there for a few minutes reflecting on the events of the last few days and thought to myself just how lucky I was to have had this opportunity. Finally my full bladder pushed me out of bed. After relieving myself, I went out to the kitchen and made some coffee. When it was ready, I went and sat where I could look out the window at the lake. The quiet morning view was wonderful. Soon I heard sounds behind me and as I looked up my dear sister...
Laying in bed Monday evening home alone I texted with my girlfriend Jessica chatting to her as well as messaging my ex girlfriend Cassi confirming that she would still be sleeping over tomorrow night. Cassi replied back most definitely baby I'm looking forward to seeing you and spending the night together.I was too excited to fuck her sexy body again and soon while laying in bed a fell asleep.Waking up the next morning just before 8 I got up and made myself breakfast and while eating I message...
It was a Thursday night and still being single and a bit lonely, not getting as much sex as I was use to having a girlfriend, I decided to message Cassi to see if she would be keen to meet up for the day. She was indeed keep and as we chatted she said she would meet by my house just after 9 tomorrow morning. She seemed rather excited and we continued messaging each other for a while before saying goodnight. I almost immediately fell asleep after my last message to Cassi. Waking up Friday...
I was home one Saturday morning when I got a call from an old high school friend that I had seen only once in the last ten years. Chris asked if I was still collecting comic books since he was going to sell some of the better books in his collection. I told him I was, but hadn’t done much collecting in a while, and money was kind of tight for the wife and me. Chris told me to come over to his parents place (he was just in town for the weekend) and take a look at the books. Maybe we could work...
My family consist of my father,my mom,my sister and myself aman.My father is 51 and my mother is 38.My age is 20.My massi name is meenakshi and she is 30.I was very normal guy until I get a chance to fuck my mother.My mind got corrupted and I started fantasizing around woman around me. Slowly I dived into world of incest taboo porn especially massi and her sister son.First I watched son and mom porn but I got a chance to fuck her now I want my massi.It simply blew my mind I started imagining...
Several years ago, I worked for the same company as a guy called Tony. His nickname was 'Tony D' and occasionally I would be invited to his house, either to watch a game or for a party. Tony was a classic Italian man with dark olive skin, black hair and big, wide shoulders. He had a hairy chest and a stocky build.Tony was married with older k**s. I had been married for nineteen years with one c***d.One day I got a text from him on my cell phone: 'missed you last night'. I thought, that was...
The building had obviously been repurposed several times in its life, and every time it was done it appears to have been done on the cheap. It looks like there might have been no plan to start with and every stage was an afterthought (Hey, why don't we...). The building might have started as a mechanic's garage. It had a flat roof so it was some kind of commercial building. It was on the edge of residential property that was older and, not dilapidated, but well worn. It was at the end of the...
I don't think I am that unusual. That is, not that unusual before my accidental encounter with a high school acquaintance turned my life upside down. I am married, fit guy, in my mid-thirties. At just a tad under five foot eight and 155 pounds, I have a slight build. I am a naturally hairless and smooth guy. I always considered myself straight but have also always been attracted to men. I have a normal sex life with my wife. I don't see other women outside of my marriage. In fact, I only rarely...
Hi ISS readers!!! Though i have been reading stories on this site for close to a decade, this is the first time trying to post my own experience. Bear with me and request to provide me with feedback to improve so that i can keep sharing my experiences in an interesting manner!!.. Little brief about me, For the purpose of reference – call me Sathish !!!.. I am 32 yrs old and work in an IT MNC domiciled in Chennai. I Love Sex and hardly i remember a day where i have spent with watching something...
After spending a majority of the morning sucking off one of my closest friends, I spent a few quiet moments sitting on my bed, back in my own hotel room, trying to comprehend what happened. I nervously twisted my wedding ring around my finger, anxiously thinking about the pictures I had allowed Brad to take of me. What was he going to do with them? What if one of them found its way back to my wife?All the sensations I had just experienced came flooding back to me. The warmth of Brad's stiff...
I was long overdue for a vacation and since I wasn't seeing anyone I thought I'd take one alone, rather than with a friend or a group. And I didn't want to do what I'd done before, go to a gay resort where everything is so gay! gay! gay! An unattached dude at one of those places deals with too much shit. I just wanted to relax and I wasn't looking for a meat market, so I thought I'd go spend a week at a Caribbean resort I'd heard about. This was one of those pleasure-focused places where...
I have always considered myself heterosexual, although I have been bi-curious for many years I have never had a sexual experience with a man until last summer.To help ends meet we have taken in foreign students over the last few years. The money is good and the students are usually no trouble as they are out studying during the day and either go out or stay in their rooms at night. Last summer we had a beautiful 30-year Old Italian woman called Carla come to stay for three months. She was...
I've always thought of myself as straight. I've never had the opportunity to ever be with another man. Sometimes you hear about situations when guys hang out as k**s and while they're drinking or getting high, they give each other blow jobs or jerk each other off.That never happened to me, ever. I've never thought about being with a guy. I've always had my share of women and I've always thought of myself as a guy that enjoys pussy. Never once have I ever thought about a dick.I love women and...
This began simple enough but turned into a total fucked up mess with me in the middle and center of attention. Having been married a long time it's easy to become very definitive in your lifestyle. For years my wife would always bug me about tasting my own cum or dining on a cream pie. Weather she blew me and fed it to me or eat her out after I came in her pussy didn't make any difference to her, she just wanted to see me eat my cum. With a very emphatic "SORRY I don't go there" statement I...
I looked at the leader of the group and he was smiling a knowing smile. They had me and I was powerless to fight. I thought I had done enough to get out of this situation, but it did not seem so. As I glanced down, I noticed the leader had a sizable hard-on trapped inside his tight black jeans.He walked over to number 2, took the camera and ordered me, "stand up."Then he told number 2, "Take of you pants and assume the bottom position, knees up and ass out on the edge of the bed."The leader...
This is from the times when I had just turned 18 and had shifted my base to Delhi i. e mona massi”s place for my studies. mona massi was a very sexy lady around 39-40 years old. One whom i had been dreaming of fucking ever since i started jerking.actually she became my dream girl when i accidently saw her nude bathing in our village bathroom.and ever since that day i have failed to spot some body sexier than hers.she was a perfect figure thin waist like pamela anderson with beautiful sexy...
IncestBefore being married, I was living in a house with two artist students. My then girlfriend lived in her own house share. Ours was a very large house with spare rooms we’d use for studio space, open areas for communal get togethers and all in all we were a happy group of three young guys, committing to our creative lives and generally having a good time. We decided after some time that one of the smaller, unused rooms may as well be used for another flatmate to reduce our expenditure. The word...
Over the next week, Cassy found herself with questions, anticipating another round of Daddy and Mommy’s education. She stood in front of the full-length mirror in her bedroom trying different clothes, stripping slowly, looking at her body from all angles while she played with what Mommy told her was her clit, which was short for clitoris, that little nub of skin at the top of her pussy. She quickly realized amazing feelings came from there as she rubbed it. Over the week, she had closed...
Note : this story is completely fictional! This is from the times when I had just turned 18 and had shifted my base to Delhi i.e Mona massi's place for my studies.Mona massi was a very sexy lady around 39-40 years old.A perfect indian milf ,one whom i had been dreaming of fucking ever since i started jerking.Actually she became my dream girl when i accidently saw her nude bathing in our village bathroom.And ever since that day i have failed to spot some body sexier than hers.She was a perfect...
IncestI could hear them. Their moaning. It had been going on for about two hours now. How can people even bang for that long?I rub my forehead and shake my head at the painful ringing in my ears. Like studying wasn't hard enough anyway, now I had to put up with my roommate and his girlfriend banging."Oh, Nate!" Amy screams.Ugh.Nate is my roommate. We're pretty close, which is why I try and let these little moments slide... but recently it seems like they have been happening a lot more. He's your...
"You're Kalliste's friend aren't you?" Caroline asked Kit Cameron. It was Tuesday night at the Northwestern University Women's Co-op and people were busy everywhere. "Do you know any stories?" Kit was taking her turn at the loom and glanced at Kalliste Periakes over her glasses. Kit was like Kalliste, a woman of indeterminate age with dark hair and a slight olive cast to her skin. Her thin face showed a few lines, and at times her dark eyes seemed deep and unfathomable. "We've known...
"Hey, do you want some help?" I looked up and saw a large man towering over me. "Excuse me?" I asked him. "Well, I could spot you if you wanted to do more than just free weights," the man offered. I looked up at the guy. He looked huge! Especially with me sitting on the bench. The guy easily stood over six feet tall. Maybe six feet four inches, a couple of inches taller than me. And he was easily larger than me. But not by a lot. I may be only 18, but I've been lifting weights for the past two...
I was playing some basketball down at the gym the other day with a bunch of my buddies. We had a great game, strenuous, but fun. Afterword, instead of hitting the showers, Cody and I just stayed in our gym trunks and t-shirts and I went out for a couple of beers. Cody's a great guy. A 31 year old divorced stock broker, 6'4" tall and chiseled out of granite. We'd been work out buddies on occasion and the one time I'd actually seen him with his shirt off, I thought he looked like a fuckin'...
Oh God, I could feel his thick cock beginning to press against me. He had greased me with K-Y lotion all over my asshole and his cock, and now I was on my hands and knees about to receive him.His cock head slid against my ass cheeks, seeking that warm, special spot. He moved it upwards until it caught the my crack, and a slight gasp left my parted lips as I felt it pushing. I arched my back as his strong, calloused hands found a better grip on my hips, and my calves raised off of the bed, my...
Cockatoo Part 4 Return From Bangkok It was late afternoon by the time my flight left Bangkok and dusk began to fall about halfway back to Koh Samui. Lights from the fishing boats in the Gulf of Thailand began to glitter like tiny jewels in the gathering darkness. I could make out the dark shape of Koh Tao, and I shivered at the memory of what had happened down there only a few weeks ago. How close I had come to death in the cold, dark water, and how, given a second chance at life, I was...
Cockatoo Part 4Return From BangkokIt was late afternoon by the time my flight left Bangkok and dusk beganto fall about halfway back to Koh Samui. Lights from the fishing boatsin the Gulf of Thailand began to glitter like tiny jewels in thegathering darkness. I could make out the dark shape of Koh Tao, and Ishivered at the memory of what had happened down there only a few weeksago. How close I had come to death in the cold, dark water, and how,given a second chance at life, I was determined to...
Cockatoo Part 19 I live for feedback [email protected] We finished dinner in the restaurant, then walked upstairs to the flat and sat out on the terrace, drinking and talking about what our next steps should be in the plan to launch the new club. We threw around ideas for possible names, some better than others, and we provisionally settled on Cockatoo Cabaret as a tie in with the bar. I also mentioned that when I had googled Koh Samui Blue, I discovered there were barely...
There's nothing worse than two divorced guys sitting around watching television on a Saturday night. Lamar lost everything when his wife took everything he owned. All he had left after he got home from work that day was the car and the clothes he had on his back. I wasn't much better off. The only difference seemed to be in the bills that were left behind. In this department, I was the ultimate loser. Still I managed to get a tiny apartment behind an old house on the outskirts of town. When I...
Note : This story is completely fictional! Second sex with massi After the first encounter I had with massi we became a pair and had the best sex of our lives during that period .And the best sex invariably would come on the Saturday night.and the first sex and the second sex could not have been on seperate days.Who could have waited? Not me ,neither massi. Coincidently it was a Saturday .After the great facial i gave to massi in the first encounter i garnered energy after 2 hours to get up and...
IncestCockatoo Part 6 I live for feedback [email protected] We stayed wrapped together until we began to fall asleep. Alex eventually turned over and I spooned up to her back, she pushed back into me, turned her head around and we kissed good night. As I drifted off to sleep I heard her say softly, "Chan rak kun, James, I love you." The day dawned as most do in Koh Samui with bright sunshine. Alex was up very early making a lot of noise as she got ready for our day ahead. We had...