Anal

A Night with a Craigslist tranny

I hadn’t been with a girl for a while and obviously not having had sex either, I started looking to the internet. I searched for porn to watch and masturbate, and then not heeding my own warning that it could have deadly consequences, I thought about maybe trying to hook up with someone off Craigslist.

Prior Planning Prevents Pregnancy

Sex-Ed. How boring. Got to admit it was fun putting the condom on the banana and joking later with my friends. The dry lecture on how the sperm fertilizes the egg. How I wish sometimes that the class was Sex Training instead of Sex Education. Would be a lot more fun, don’t you think?

Wanderers – Part One

Part One
Chapter 1: A History
Chapter 2: Our Mission
Chapter 3: Hope
Chapter 4: Initiation
A Message From The Writer:
This is the first part of my first writing series, so let me know in comments and in ratings what you think, and maybe what you’d like to see from it in the future. As this is a first part, it is very background-heavy, so if you want to read it purely for sexual content it begins in Chapter 4. The sexual content will be more frequent and diverse in future parts.
***
Chapter 1: A History
Captain’s Log #131,
I am writing this in the hope that someone out there will find it. We don’t know how long we’ve been travelling. The last we’ve known it was the year 2525, when we, like so many others, were forced to leave our home on Earth in order to survive.
This is the story of our race, from the years 2050 – present. This may seem exhausting to read for very little gain, but to whoever may read this, I feel it is important to include in order for you to fully understand my story. However, if you so wish to hear the main part of my story, without the background to it, you are welcome to skip this log.
As far as we know, we only know for sure that more human species live out there, and as such I am writing in my native language, and I go on to use terms, measurements and concepts of time as far as we understand it to be, so I hope it can somehow relate to your understanding of it, whoever comes across these Logs.
Over the past few hundred years, the human race had gradually outgrown their planet, nearly exhausting all it’s natural resources. But they survived, evolved and adapted to the changes in climate and environment. They learned to artificially create the things they needed to survive; food, water, oxygen; and mostly now lived underground, as the planet became uninhabitable on the surface with soaring temperatures and hostile weather. It was a difficult, and long transition, but it was a necessary one.
But even through all they’ve been through, it soon became clear it would not be enough. Their planet was dying as increased pressure from the humans yet still continued to use what was left of it’s resources, and would soon not be able to sustain the vastness of their species.
Though the humans have always been a clever race, and had seen this coming for hundreds of years, since the early studies of global warming, a study which evolved with time, and luckily enabled them to predict the eventual eruption of the Yellowstone Super-volcano in 2202. In anticipation of such a catastrophic, and potentially apocalyptic event, the species took the temporary measure to move underground, as mentioned above, but more importantly began to develop a more permanent solution.
During the late 21st Century, the countries that once separated our species decided to coalesce in a global space program, now that we finally had the technology to pursue a space exploration program, in order to try and find out if we are alone in the universe. But after numerous failed missions, it was deemed unsuccessful and the program was sidelined.
In light of the events at Yellowstone, those people now driven underground began to resurrect the long-since dead program on a much wider scale. A scale that would enable in more recent history, our planet’s entire population to venture out into space on separate courses, in order to try to find new, habitable planets, or at least any resource they can salvage from others, for the sake of the survival of our species.
The Human Race had become no more than mere scavengers, scattered across the galaxy and beyond, who’s only remaining purpose became survival.
***
Chapter 2: Our Mission
Captain’s Log #142,
I am writing this in the hope that someone out there will find it. We don’t know how long we’ve been travelling. The last we’ve known it was the year 2525, when we, like so many others, were forced to leave our home on Earth in order to survive.
This is the story of how we ourselves came to be out here. Again, I must say this may seem exhausting to read for very little gain, but to whoever may read this, I feel it is important to include in order for you to fully understand my story. However, if you so wish to hear the main part of my story, without the background to it, you are welcome to skip this log.
In a previous log I told the story of how our species developed a space program in order to escape our decaying planet, and enable our entire population to venture out into deep space. This was not entirely true. There was never going to be enough resources to get everyone off the planet, so the people in charge at the time decided that some of us weren’t worth the trouble to save.
It was a sad truth, but what they thought was a necessary one. Those people included the elderly, the disabled, the mentally challenged and criminals, who were to be left behind. As I say it was harsh, but as was the time we lived in. Us humans became something we shouldn’t have, and it became survival of the fittest.
I would like now to tell a more personal story, about me and my partner. Well, more of a professional partner. We were unfortunately due to be in the group that would be left behind. We were convicted criminals, though using the term convicted lightly. In the later years of our planet, the justice system fell lower and lower on the list of priorities for the people in charge. It practically rivalled the legal system of the medieval times, where if you were accused you were pretty much guilty.
My name is Zara, I am 20 years old, or at least I was when we left, as I say we have lost all concept of time since our journey began. I was incriminated on a petty theft charge, and though there was no doubt of my guilt, I still feel I needed to do it.
I was 19, and lived in a poor family. Though we were all poor at the time, we were in amongst the worst of them, each wondering if and when our next meal would come. I was forced to look after my younger siblings, of 12 and 5, too young to fend for themselves, as our mother had recently passed, and had not seen our father for some time.
One night I snuck into one of the nearby facilities where the food was artificially created, and stole a few samples to try and feed my family, who I had left with our good friends. I came in late, as to try and avoid any security if possible, but did not account for the security guard who left his tablet behind, who caught as I tried to make my way out. I was convicted without so much as a trial.
I feel some of you who read this may need me to describe my looks, in order for you to visualise the story I will tell, and as such I will. For those of you who wish to leave what I look like up to your imagination, then you can so choose to skip to the next paragraph of my log. I am 5’11, which is fairly short given the time period we come from. I am slim, but with a fairly curvy physique at 34c breasts, and shoulder-length sort of spunky-like styled blonde hair and green eyes.
My partner’s name is Evans, he was 28 years old at the time we began our journey, but as mentioned we can’t be sure anymore. He was a convicted rapist, but the less we say about his past the better, he’s not generally fond of sharing it anyway.
But one thing to note is I committed a crime out of necessity, whereas he did it out of greed, I can only assume. Again he too though was convicted without trial, and I’m not even sure he did it myself, he gas refused to talk about that part of his life ever since I’ve known him.
Again, I feel some of you who read this may need me to describe his looks, in order for you to visualise the story I will tell, and as such I will. For those of you who wish to leave what he looks like up to your imagination, then you can so choose to skip to the next paragraph of my log. He is 6’4, with a large, muscular build, and short flat-top spiked-out jet black hair and deep brown eyes.
Now you might be wondering how our paths crossed, if I were only a criminal of petty theft, and he a convicted rapist. Well the are a couple of reasons, and as above I said the justice system fell lower and lower on the list of priorities for the people in charge, and as far as they were concerned once you were convicted as a criminal, you were pretty much dead anyway, as they had already planned to leave us behind on this planet.
The other reason was that at a time where any kind of resources on the planet were low, petty theft was far more severe an offence than one would think, and as such I found myself in this situation. Still, the circumstances of my partner and I meeting wasn’t pleasant. Being an attractive young woman in a prison filled with criminals of all natures is a recipe for disaster, as I was all too soon about to find out.
***
Chapter 3: Hope
Captain’s Log #143,
I am writing this in the hope that someone out there will find it. We don’t know how long we’ve been travelling. The last we’ve known it was the year 2525, when we, like so many others, were forced to leave our home on Earth in order to survive.
I would now like to tell you about my time in prison. Even though this is a sensitive subject for me, as it was a really tough experience, I feel it is necessary to tell in order to understand how I now find myself here.
As I’ve mentioned, I found myself, an attractive young woman, in a prison dominated by men, most of whom looked like they could snap me in half if they so wanted, which luckily they didn’t, though saying that it might have been better than what they did put me through.
It was a low security prison, as no one thought to dedicate any resources towards people who were destined for death anyway, and what little security they had there didn’t much care for what went on inside regardless. Men and women of all classes of criminal, sharing the courtyard, showers and even cells, we were all but abandoned, forgotten by the world. It really felt like hell on Earth.
They started to notice me as soon as I entered for the first time, as if they were predators, singling out the weakest in the pack. As I was dragged through the prison barely still on my feet, past all the cells I could see them all, just staring at me, as if they were analysing every inch of me. All of a sudden, I was thrown into the cell, right at the end of the corridor.
I picked my head up off the cold stone floor, and tried to analyse my surroundings. But it was too dark to make anything out. All I could see where two sets of bunk beds on the other side of the room, and a bucket in the corner, what I assumed to be the toilet. Then, I saw movement in the opposite corner of the room. A small shadow. I heard something come from it.
“W-wh-wh… Who’s there?”, a timid voice originating from the shadow, now clearly a person, female. I felt I had to reply, the girl clearly scared, and from what I’d seen and heard in my little time here, she had good reason to be.
“It’s okay,” I replied, “I’m not going to hurt you. I’m new here.”
She began to crawl out from behind the beds. She was shaking, clearly traumatised, but by what?
“What’s your name?”, I asked, maybe hoping by building a friendship it would make my days in here more bearable.
“Aurora”, she replied, now clearly visible in the dim light. She was quite cute, if I do say, even if I don’t swing that way. Petite, maybe 5’7, very skinny, and clearly lacking the food and nutrition she would need, a theme that appeared to be fairly commonplace from what I’d seen among the ‘weaker-looking’ of the inmates.
She had beautiful long auburn hair and bright blue eyes, and nice pert breast and ass despite her skinny nature, all traits I’m sure didn’t help her situation amongst the other prisoners in here. “What’s your’s?”, she added, me almost forgetting where we were, admiring her beauty.
“I’m Zara”, I replied, offering a handshake, which she tentatively agreed to, followed by a period of awkward silence, which seemed to last an eternity.
“So, what are you in for?”, I asked in a hope of breaking the silence.
She stayed silent for a little while longer, before finally muttering, “I stole some food, from the breeding lab”. Alas, we had something in common. After that we continued conversing for what seemed like hours, about food, our families, and wherever the conversation led. I even got her to smile, she said it was the first time she had done so in years. Before I knew it, I had hope, from what for a long time seemed like a hopeless situation. Maybe from the friendship we had formed, I could survive whatever horrors lied on store for me in this miserable place.
But I had forgotten about all of that as I bonded with my new-found friend, a light in a sea of darkness. But it wasn’t all smooth sailing, as I was very soon about to find out. Aurora and I had reached a point in our conversation where we started to talk about the other inmates. It was not a pleasant one, as she began to reveal some of the awful truths that I had feared about this place. Some of the awful things that went on between the prisoners, with the stronger of which taking advantage of the weaker, driving many to commit suicide, some in the most brutal of ways, which I won’t get into, just to escape the horrors.
Even what Aurora herself had been through, things which would haunt anyone for life, but she still had a deep, strong will to survive, and power through, even though each and every day it became harder for her. But maybe now that I’m here, I could help ease some of her pain, help her get through the remainder of her sentence.
“We can get through it together”, I exclaimed to her, “It’s a brutal, and garsh reality we find ourselves in, but we can get through it, we won’t be in here forever”, I said promisingly. Truth be told I had no idea how long I’d be here, if I’d even ever get out as I was convicted without a trial, and as such not given a formal sentence. Aurora though certainly wouldn’t. She told me she’d already served much of her sentence, and would be out in just a few weeks.
I must say I was a bit disappointed when she broke the news. Glad for her of course, but sad that I would only have her here with me for a short time, having to serve the rest of my sentence like she had served almost the entirety of hers. I told her we could meet up when we both get to the outside, but it was clear she had her doubts. Doubts that I was strong enough to survive the horrors this place would present to me, doubts that I too, unfortunately shared.
***
Chapter 4: Initiation
Captain’s Log #146,
I am writing this in the hope that someone out there will find it. We don’t know how long we’ve been travelling. The last we’ve known it was the year 2525, when we, like so many others, were forced to leave our home on Earth in order to survive.
It’s been a while since my last entry. I would now like to tell you more about my time in prison, continuing from where I left off with my new found friend, Aurora. Like I have said in a previous entry, even though this is a sensitive subject for me, as it was a really tough experience, I feel it is necessary to tell in order to understand how I now find myself here. This is where my story becomes, all too brutally, real.
Things were starting to look up, albeit minutely. I still had to go through time spent in close proximity with the other inmates, namely yard time, at meals and in the showers. And sure enough, just a the thought of these started to creep through my mind, the guards came down the corridor, as if to warn me for the dangers that would surely lie ahead.
“Yard time!”, they exclaimed in deep, menacing voices.
Aurora got hold of my arm, in obvious fear of what was to come. We were amongst the last to leave the illusionary safety of our cold, dark, damp jail cell. We were led by the guards down through the corridor I went through earlier, and a couple of turns later we were outside. I had not realised it until we left, but it was noticeably fresher, now we were temporarily out of the dingy prison. But that’s not what shocked me the most.
I immediately noticed how secure it was, not like I had imagined it to be, or what Aurora had described. It was fairly calm amongst the inmates, no violence or hateful nature between them, and there were more than enough guards there to disperse any potential trouble, should it arise. But as soon as I began to wonder why Aurora, who was still clutching to me closely, seemed so keen to avoid this; she leaned it to me and whispered in my ear.
“This isn’t the bad part. It’s what’s to follow that scares me”.
I could tell by the tone of her voice that this is where it would take a turn for the worse. The pleasant break of fresh air in the Courtyard all too quickly came to an end, with the guards calling out two words that to this day still haunt me.
“Shower Time”.
We’d all heard stories about what goes on in prison showers, even from the outside, but nothing I had heard could prepare me for what was about to happen. What’s more, is I knew it as soon as I saw the courtyard split into to types of people. Those that had a menacing smile on their faces, notably the stronger looking of those, and those that seemed to tremble in fear, some even fighting to try and avoid going, but the guards were clearly having none of it.
It must have been the longest walk of my life, even though it was literally just down the hall from the courtyard, and suddenly, all my fears had been realised. We entered the shower room, it was unisex, and unguarded. It was a very long, divided into separate but opens sections of shower areas. Sounds could be heard from the back, almost inaudible, but clearly sounds of pain. This was it, and there was no avoiding the inevitable.
Aurora and I, still staying close, moved slowly past the shower areas, trying not to look at anyone the wrong way for fear of what might happen. But it was clear what was happening in some of these areas, brutal and nonconsensual, men and women alike; and with this it became clear that we would inevitably suffer the same fate as these poor people.
We found an empty area a few in, but as soon as we got there, we realised we were followed. All of a sudden, Aurora and I were forcefully separated to opposite sides of the shower area. Two strong hands gripped my arms and held me in place, and it soon became clear I was not going anywhere from this. The next thing I knew, my clothes were being taken off, carefully though, as I assume not to alert the guards that anything had occurred.
Slowly, my top was being removed up my torso, over my tits and eventually over my head. Next came my trousers, as I felt them gently being curved away from my ass, and down my smooth, long legs, down to my feet. where I was slowly lifted out of them. It was a weird feeling as they were being removed, because it almost felt kind the way they were caressed off my body, but in reality it was just so they weren’t going to be caught. But for a moment, it almost felt like how my boyfriend used to do it, in a romantic way, before he passed.
Unfortunately, underwear was not standard issue uniform for prisoners, so I soon found myself there, being held in place, completely naked and exposed. What’s worse, is it soon became apparent that the guy holding me in place was not the only one there. In fact there were four of them surrounding us, I assumed two for each of us. I realised this when a third hand, along with the two holding me in place, started rubbing my inner thigh, making its way down my smooth, silky leg and back up, further than where it had started, and I squirmed, trying my best to free myself from this almighty grasp.
“Don’t!” cried a voice that had become familiar to me, it was Aurora. “Don’t struggle, it will only make things worse for yourself. Trust me, I’ve been here, I’ve tried it all. No one will come, no one will help, no one cares. You will only end up getting hurt more than you need to. The best thing to do is just take whatever comes, because it’s going to happen whether you want it to or not. I’m sorry, but it’s for your own good.” I heard clear pounding noises follow Aurora’s speech, followed by noises of pain, clearly foreshadowing what was about to happen to me.
So I listened to her, as it was clear from her tone of voice she had experienced what would happen if I heed her warning. So I let it be, and tried to think about other things, to zone out while it was going on, but it was hard to ignore. The huge hand that had been caressing me had now reached my loins, and started moving itself between the lips of my pussy, rubbing hard, back and forth.
“Look at this, Cole. She’s soaking down here.” Came from a deep voice. Having not realised it myself from trying to zone out, I could now myself feel that juices from my pussy had started to flow. It’s not that I was getting turned on by this by any means, it’s just it had been a long time since anyone had touched me so, down there, not since my boyfriend who had long since passed, and my body was reacting to the stimulation.
“I think she’s ready for us”, came the other voice, the one of the man holding me in place, who I now only knew as Cole. I was not, though. I don’t think I ever could have been, and I certainly didn’t want to be, but that choice was taken away from in this situation.
“Not yet,” the first man said, “Let me just make sure she can accommodate us”. Before I even got the chance to think about what he meant by this, he had forcefully shoved one of his fingers straight up into my pussy, followed by another, and another, and before I knew it, he had the whole top half of his hand inside me. He then clenched his fingers together, which became a short relief to the depth he was going in, but an instant feeling of pain as it stretched my pussy hole outwards.
I had never been stretched like this so violently before, I had only ever had my own fingers in there, and even then only one or two at a time, or my boyfriends penis which wasn’t particularly lengthy or girthy. I could then feel his big hand, now in the shape of a fist, slowly moving further into my stretching, hurting hole, until I could feel my lips close slightly, clutching around his wrist, which was significantly smaller around than the rest of his hand, as his fist had inserted wholly into me. It hung there for a while, and gyrated a little, but surprising not a whole lot more, until I eventually heard him speak again.
“She’s a little tight, but I’m sure she’ll be able to accommodate us if we make it”. I didn’t like the sound of that, especially the way he said ‘us’. I’d had only ever been with one person like that, and now all at once it looked like that number was about to treble. The man beneath me then thrust his hand out from inside me in one swift motion. It was temporary relief until I felt something poking me on the back of my leg. It became clear it was Cole’s penis, as he raised it up and began to rub it between my legs, brushing it up against my pussy and clit, back and forth, which gave me my first impression of the sheer size of it.
‘It must have been 9 inches’, was my first guess, I thought to myself, ‘and feels like twice the girth of my boyfriend’s’. As it turns out even then, I was underestimating, and bigger still was the other man’s as it came into view, as he slid on the ground beneath me, between my legs, as if waiting for me. All of a sudden, the rubbing between my legs was taken away, as a firmer grip was put onto my arms, it felt almost bone-crushing, and I was forcefully being lowered to sit on the lower torso of the other guy.
Cole lowered with me, and was now kneeling behind me as I sat on the other guys stomach, and I was bent forward by Cole, to display my two clean shaven holes to the guys, eagerly awaiting. I then felt a prod, first at the entrance to my pussy, and then up to the one at my ass. Then together, they both started pushing against me, not wanting to go in at first and was just pushing my whole body further up. But Cole’s grip on me prevented me from moving any further up, until finally, the one at my pussy found it’s way in, and was immediately up 4 inches inside.
This was soon followed by the one at my ass, which was far less lubricated with no juices to cover that area of mine, and was far tighter, which lead to me letting out a short, sharp scream, which was quickly covered my the man beneath putting his hand in my mouth. Incidentally it was the one that had previously been inside my pussy, so as this was going on I could taste all the juicy residue that was left over, that was once from my own pussy.
For a little while they just hung there, 3 or 4 inches in either hole. But before I could wonder what was going on, as if by clockwork, both of the long, thick cocks slowly slid further and further inside me, until they both came to a sudden stop, when I felt both the mens hips pressed up against mine. The gentleness of this however, is not to make light of how much it had hurt me the further it went up, me carefully trying not to bite down on the man’s hand, in case like Aurora had suggested I would be punished, nor was it an indication of how the remainder of this would go down.
I looked up for the first time during this, as I had been curiously watching what was going on behind me, to find Aurora’s face, staring back at me, right up close to me. I looked behind her to see that she had the exact same situation I had going on, with two men thrust as far inside her as they could. As soon as I had come to terms with my surroundings however, the four men all at once pulled back, and I naively thought it was all over, a hope quickly shattered as they all thrust back in, as quickly and as deeply as they could, the pain from which causing Aurora and I to scream harshly, through the hands that occupied our mouths.
As the brutal thrust came in once more, it felt like all of my insides were being moved further up my body. Again, and again they thrust, getting faster and faster, and with each came another short, sharp scream from Aurora and I, before the four men settled into a steady rhythm of deep, quick thrusts, pounding away at our insides, clearly hitting something at the end of our tunnels, making it all the more painful each time.
But we weren’t doing this in silence either, in fact what we heard possibly made it even worse. The guys there would throw in the occasional comment, like “Take it you bitch”, or “Yeah you like that, don’t you? You little slut!” It was really demoralising. But even with all the pain that came from the constant, rhythmic pounding, I had a warm feeling coming from my loins, and filling my body. Was I actually enjoying this? Surely not, I thought, it must just be from the stimulation of being touched down there, and being fucked.
But the warm feeling was growing, and even started to take over, as I could feel myself starting to move along with the thrusts, and even starting to thrust myself back against them. I even started to hurt a little less, as it seemed my holes had expanded to accommodate their cocks’ vast size, and was starting to self-lubricate as the juices from my pussy started to flow out of it, onto their cocks as they pulled out and pushed back in. I looked over and could see Aurora doing the same, moving back and forth against her guys.
Although the initial pain had more or less subsided, I could tell this would still leave physical and emotional pain on me in the future. I looked up once more and saw, to my surprise, Aurora had her eyes closed, mouth open, and was now moving back and forth faster and harder, getting into the rhythm more and more. I could tell she was on the verge of a climax, as she started to moan lightly, not the same moans as before with the initial pain, but moans of pleasure.
Just the sight of what was happening opposite me was enough to get me going into another gear, as I too began thrusting back and forth, harder and faster. I could here Aurora, now screaming at the top of her lungs, still with the pussy juice-covered hand in her mouth, as she froze, and moved into an explosive climax. I could see the juices flowing from her, leaving small puddles on the floor.
The thought of her climaxing so immensely was enough to send me over the edge, as I too stopped thrusting and froze there, juices pumping through my innards, flowing out of me onto the guys’ cocks that continued to pump in and penetrate me. I screamed, and grabbed hold of the guy below me’s free hand, and clenched it, as I too began to climax.
I thrust backwards one last time so I was pressed against the two guys’s hips so that their cocks where all the way inside me, pressed up against my cervix, as I too exploded into a mind-blowing orgasm, that seemed to last forever, as the guys continued to thrust brutally into me, not seeming to care that I had cum. But they themselves were not done.
I had never felt such a rush, even being used by these two guys with oversized members so violently. The thought of not being in control of anything that was going on, I must admit, quite excited me, though I certainly didn’t want to admit it at the time, not even to Aurora, who in hindsight probably would have felt the same way at the time. But this was not the time for reflection, and even though I was spent from my exhilarating, exhausting orgasm, the guts had not finished yet, and I got the feeling I would be there till they were done.
They continued to pound me as hard and fast as they could, not seeming to show any kind of fatigue, which was amazing to me really, so too did the guys opposite me, doing the same thing to sweet Aurora. It lasted for a while longer, until it began to hurt again from the constant friction, losing lubrication by the thrust until finally, one of them was ready. The guy below me, presumably because he hadn’t had to use as much energy as he was lying down, and with easier thrusts with the lubrication from my pussy juices, was the one to cum first.
He pulled out, I assume as to not risk impregnating me, and slid over to be in front of me, and with a couple more big strokes, his huge cock twitched, and sprayed his hot, sticky cum over my face, and into my open mouth, even some in my hair, as there was so much of it. With the last of it being squeezed out like the last of the toothpaste, he wiped his cock on my sticky face, got up and walked away. As soon as he did, it appeared to be Aurora’s turn to receive the same treatment I did, as I watched him spurt his juices over her gorgeous face.
So we remained there for some time more, in an incredible display of stamina and control, being held in place forcefully while we were mercilessly pounded in our tight assholes, staring into each others eyes as we watched the other rock back and forth from the sheer force of it. It lasted until our asses were numb, where without much warning, both guys remarkably, simultaneously squirted inside us, filling our assholes with hot cum.
Once they were done, they left us there on the cold shower floor, and we fell flat on our fronts as they let us go from their grasps, and walked away with menacing laughter. We could barely move, assholes and faces full of their vast quantities of hot, sticky essence, the showers turned on and sprayed us with cold water, emphasising our dejected state of mind, knowing that this was just the first of many encounters of this nature to come, in my long stay here.

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Journal of an Agent: Chapter1-Rachael Leigh Cook

Journal of an Agent: Chapter1-Rachael Leigh CookI did not write this story it was written by Carnage JacksonJournal of an Agent-Chapter1: Rachael Leigh Cook
Following the death of my father, I became the inheritor of his business as a Hollywood agent. I hadn’t known too much of my father, because he left my mother and I when I was 3 to pursue his dreams in L.A. and Hollywood. Having not received a birthday card or even a call in over ten years, I wasn’t exactly excited about the idea of inheriting a business. I had just graduated college with a degree in English and was looking forward to finding a job as either a columnist or a teacher or something to that effect.
My mother died right after I graduated high school, so I had been on my own for a while. I wasn’t planning on attending my father’s funeral, until his most loyal employee, a woman named Rebecca Carr called me at home to tell me about the inheritance. Rebecca had been with my father since he moved to L.A., and though they were intimate with each other early on she told me, passion soon gave way to a deeper friendship and she helped his business grow. It was upon her insistence that I chose to attend. My father’s funeral was a bit of a scene in Hollywood, as he had spent over 20 years there building a small empire. Young and old, famous and fleeting celebrities were in attendance. People guessed right away who I was, as anyone who knew my father as well as knew me said I was almost an exact image, albeit a little skinnier. I was about 6’1 and weighed about 170 to 180 pounds. I didn’t work out religiously but I was in good shape. The most striking feature I had been told were my eyes. Apparently I had inherited from my father this icy cold stare that burned through my dark blue eyes into people. Combined with my dark brown hair, I had been told by more than one ex-girlfriend that I could look very menacing sometimes when I got even slightly angry.
Following the services, I met with the executor of my father’s estate, a Mr. Blake, as well as a Ms. Carr to discuss the future of the agency.
“Your father had quite a successful business here Mr. Simonds,” said Mr. Blake. “Over 30 employees, a fine stable of award winning actors, actresses and musicians, as well as close to a hundred unknowns. Keeping retainers with virtually all of them was a brilliant move by your father, as the agency is now worth an estimated $50 million dollars. Being his only heir, you stand to inherit it, as well as his home and personal finances.”
I was shocked. I knew he had done fairly well (my mother never said much about him and his success) but I had no idea HOW well. Blake continued:
“You can do what you wish with the business Mr. Simonds, but before you act I suggest you speak with Ms. Carr first before deciding one way or the other,” Blake said.
Ms. Carr finally spoke. She was a woman in her late 50s, still in good shape for the most part. Her hair had gone gray but not in a witchy sort of way. It seemed to fit her perfectly, as though she had aged, you could tell that she must have been very attractive in her younger years. Her brownish-green eyes danced with this natural exuberance and I couldn’t help but think that she would have made a good model.
“Dean, your father loved you despite his lack of showing it. I know you didn’t know him, nor do you know the slightest thing about Hollywood or being an agent, but I think that you probably have the natural charisma your father had. You really should consider running his business. That was your father’s last wish, that you help it grow,” she said, smiling ever so slightly when she finished. She came across as a good natured grandmother, which was probably the effect she was going for. Her last part angered me a little, trying to play the pity card.
“Look, I know that he wanted me to run things, but I don’t have the slightest clue. Even with you here to help me, I would still be lost, not to mention be light years behind in learning how to schmooze this town,” I said.
“I only wish I could stay to help you. Like your father, I put my heart and soul into here but now I have to cash out. There are too many memories, too much pain. Besides, I’m an old woman. I want to enjoy my late years,” replied Rebecca.
“Well, that’s just great. Now I have NO ONE to help me, even if I DID decide to stay!” I said, throwing my hands in the air in exasperation.
“No, no, no, that’s not true. Ever since your father became sick, I knew I would be retiring. I’ve been training a replacement though, and I’m sure that she will be able to help you just as well as I could,” said Rebecca.
We discussed and debated for over two hours, but in the end (and much to my chagrin) I agreed to stay and try to run the company for an interim period of six months, just to see how things went. That would give me time to tie up loose ends and sell clients to other agencies if need be. I went home to my father’s house that night, laying in bed thinking about all that I had brought upon myself. I concluded that I was at a good cross road and that because of the safety net of money left to me, I could afford to take a risk like this. Hey, I thought as I drifted off to sleep, maybe I’ll get laid somewhere along the way.
I went into work on Monday feeling optimistic about things, as well as a little apprehensive. I went into my father’s office and sat down in his chair to try and sort out files and such. I hadn’t been sitting for 5 minutes when a knock came on the door.
“Come in,” I said as I straightened up in my chair and tried to look my most professional.
The door opened and in walked a beautiful young woman, wearing a knee length maroon skirt and a white blouse. Her hair was a rich black and her skin was of an olive complexion. She had bright green eyes that were perfectly positioned on her face. Her nose was small as were her lips, which was a shade that matched the colour of her dress. Her chest wasn’t enormous, but certainly tested the limits of the fabric of her blouse. She walked with a kind of step that exuded confidence in her, but also showed she couldn’t be fucked with. I liked her already.
“Hi. My name is Julie Carr and I’m here to help you sort through those files on your desk,” she said. She spoke with an unmistakable California accent, one that showed she had lived in California her whole life. My mind immediately made the connection when she said her name.
“Carr? Are you related to Rebecca Carr who used to work here?” I asked, already knowing the answer.
“Yes. She is my mother. But like you, I never knew my father. Mom has been training me to help you for two months now and I think I will be able to help you figure things out. You ARE Dean Simonds aren’t you?” she smiled at me.
“Yes, that’s me. How did your mother know that I was going to be running things two months ago? I just met her two DAYS ago.” I asked.
“I asked the same thing. All she said was that if she knew your father at all, convincing you to stay would be no sweat,” she replied, sitting herself in one of the two guest chairs of the office.
Her mother’s assumption about me made me a little ticked, and I guess it showed because Julie sort of got this defensive look on her face that showed she knew I was upset.
“Look, all that is over and done with. Your here for six months, so let’s try to make the most of it,” she said, extending her petite right hand out for me to shake.
I shook her hand and calmed down a little bit. Bygones are bygones I thought. For the next three hours, we poured over the files. I got to like Julie’s personality right away, but she seemed to exude this self defence sort of attitude that crushed any attempt at a sexual manoeuvre. For lunch, Julie had one of the interns pick us up some sandwiches from the delicatessen down the street. After we finished eating, Julie stood to go.
“Well, we made some good progress today. Hopefully we can get this far all the time,” she said.
“Where are you going? It’s only 1:30? Was my father THAT lax in letting people leave?” I asked.
She laughed. “No, it’s just you have a client coming in at 2:00 and I thought you might want some time to clean up the office. Oh yeah, and to get that piece of lettuce out from your teeth,” she said laughing good naturedly as she walked out.
I walked over to the mirror and brushed my teeth, and then proceeded to clean myself up. I had just finished straitening up the files we had been going through when there was a knock on the door.
“Dean, this is Racheal Leigh Cook. She’s your two o’ clock,” said Julie, opening the door and ushering in the client. As soon as Racheal had walked in, Julie closed the door behind her.
Rachael was wearing a dark green sweater and a black silk dress. Combined, the outfit went a long way to hiding the curves that she had to have underneath. Even though I wasn’t from Hollywood, I certainly knew who she was. Even in person, she exuded this sort of shy radiance…like a delicate flower who was afraid to blossom. Her hair was pulled back behind her ears and she looked almost elfish. Despite wearing 5 inch lift shoes, she still barely would have come up to my chest. I rose to greet her.
“Ahh, Ms. Cook. How are you? I’m Dean Simonds. Would you care for something to drink?” I said.
“A glass of water if you don’t mind. I’m sorry to hear about your father. He was a terrific man. In fact, that’s sort of why I am here today.” she said.
I walked over to the mini bar and poured her a glass of water, fixing myself a scotch over ice.
“What do you mean?” I asked, handing her drink to her. She did indeed only come up to my chest. Raising her head, her deep, soulful brown eyes looked me in my eyes.
“Well, I was planning on coming over to your firm as long ago as last year, now that I finally got all the legal paper work done with my ex agent. I had to reschedule my appointment after your father’s passing. But with you running things now, I can still check to see if it is true.” she said, taking a sip of her water.
“See if what is true?” I asked a little puzzled.
Her eyes sparkled for a brief moment. Rachael laughed lightly, a very feathery kind of laugh that helped with her pixyish image. She again looked into my eyes, but this time with a growing sense of lust.
“Your father was known as a great guy for his clients it’s true. But he was even more well known by his female clients as being…well…endowed,” she said, stepping closer to me.
Her forwardness surprised me. Everything I had read about her or seen her in, she always seemed very passive and shy. But apparently sexually, she knew exactly what she wanted.
“…and with you I can see if the old saying ‘Like father, like son’ is correct,” she said, placing her hands on my belt.
My mind raced. Here I was on my first day of running a business and I was already being seduced like a common gigolo. Should I go with it or stop this now and keep from building a reputation?
My question was answered when I felt the belt come off and my pants fall to the floor. Rachael stood on her tip toes and leaned into me, forcing me back against the mini-bar. Her mouth met mine and her tongue slid into my mouth like a stealth snake. I responded in kind by meeting her tongue halfway. I lifted her up off of me and carried her over to the couch against the far wall of my office. I laid on top her, holding myself up with my arms. We kissed each other passionately and I slowly slid my hand up her side to her just big enough breasts and began to play with her right breast through the material of her sweater. I could feel her moan into my mouth, an obvious sign she was enjoying it. Our kiss finally broke, and she sat up. Reaching down, she lifted her sweater over her head, revealing a pair of grapefruit sized breasts straining and heaving against a black push up bra. She reached around her back and unclasped the bra, flinging it aside. Her breasts were bigger than I had guessed, with dark brown, quarter sized nipples in the centre of each. I stuck my hands out and squeezed them gently, massaging them around in my hands. Rachael groaned softly, throwing her head back in pleasure. Her dark brown, shoulder length hair fell upon her bare shoulders as she looked at me again with those eyes. I gazed upon her face, relishing her simple yet elegant face. Rachael began unbuttoning my shirt one button at a time, very methodically. I lifted myself up with my elbows and she slid the shirt off of me. As I said earlier, I try to stay in shape, focusing mainly on getting some tone in my arms and having a flat stomach. At this point, I was now left in only my boxers, something Rachael quickly set to remove. Using the same gentleness she had used before on my shirt and pants, she slowly slid my boxers off over my cock, allowing it to spring up and then land with a very audible thump on my stomach. Somewhere in the back of my mind I wondered if anyone heard us.
Rachael licked her lips and slowly began jacking my cock with her right hand, as I continued to play with her tits. God they were soft and felt so great.
“I guess all my girlfriends were right, having a big cock DOES run in the family,” she said with a devilish smile.
I guess I’m modest, because I never have measured how big I am. Previous girlfriends had said I was big, but again I didn’t know.
“God, you must be at least 9 inches long!” Rachael gasped, inadvertently answering my question. “And you’re as thick as my wrist! I’ve got to feel this beast in me before I let you go,” she said, smiling.
“But first, a little snack!”
Lowering her head down so that her hair fell in front of her face, her lips touched the head of my very erect prick very lightly. Snaking her tongue out, I felt her twist it around in my pisshole. Pulling her mouth off for just a split second, the cool air hitting where her warm lips had been was a thrill. But it was short lived, as in one swift move attempted to deep throat me. She got about half of my cock down her throat before it hit the back of her throat. She lifted her mouth off again and began licking me up and down, starting from the head and going all the way down to my balls, sucking on each one in that gentle manner she had been using. By this time, I was really enjoying myself, but things had to pick up. I placed my hand atop her head and forced her back down on my cock. Grabbing a handful of her hair, I pulled her mouth up and down my cock. She got the idea very quick and began bobbing up and down rapidly. I laid my head back on the arm of the couch and relaxed, letting out a sigh. She continued like this for what must have been 10 minutes, rotating between licking my cock slowly and bobbing up and down fast. Finally I said in a husky voice “I’m about to come.”
Pulling her head off completely, she grabbed my cock with her hand and stood me up. With me standing and my cock still in her hand, she got to her knees and began jerking me rapidly. I grunted loudly as my cock exploded, spraying her chin and lips and even landing a dollop or two in her hair. With my cum dripping off of her chin and onto her cute little breasts, she proceeded to lick my cock of any cum and wiped the cum from her lips, only to rub it into her chest and onto her tits. Out of breath, I sat back down on the couch. Rachael stood up before me and wriggled out of her dress, letting it fall to the floor. To my surprise, she wasn’t wearing any panties. Her snatch was a lighter brown than her hair, but was still a close match. She was shaved in a bikini line but nowhere else, which left a wispy “V” shape over her mound. Her pussy hair wasn’t very thick and I could see that her cunt was fully aroused, her dark brown outer lips glistening from her female wetness. She lowered her legs over my still erect cock and slowly let it push into her. My god she was tight, but not a virgin which really didn’t surprise me.
Finally I felt her settle on top of me, my cock buried to the hilt in her warm pussy. Rachael gave a moan of pure satisfaction and then lay her head on my shoulder. Using the couch as a lift, she proceeded to slowly move herself up and down my cock. I could feel her pussy craving more as it tried to grip me every time she slid on and off of my cock.
Wanting to match her pace because I knew I wouldn’t last long inside her (I hadn’t had sex in a while), I began thrusting my hips up every time she would pull off, making sure that no matter how high up she lifted herself, the tip of my prick was still in her. I reached down to her beautiful snatch and began stroking her clit furiously at a much faster pace than what we were going at. The combined sensation was too much for her, as she cried out in orgasm and I felt her juices spill onto my hand and legs. Feeling myself on the brink, I warned her that I was about to come. Lifting her head off my shoulder and still struggling to catch her breath after her orgasm.
“Cum…in my…ass,” she gasped.
I had never had a girl ask to be fucked up the ass, but hey, this was L.A. I pulled out of her and tried to lubricate my cock with her juice and my precum. Rachael had already leaned over the couch arm and was thrusting her ass up in the air. Walking up behind her, I bent down to lick her asshole just to soften things up a little. Placing my cock at her tight little hole, I gently pressed my head into her. I could hear her grimace at first and bite down on her lower lip until I got the head past, and then she sort of sighed in relief. I worked the shaft into her and before I even realized, I had all but a few inches in her.
Because I was the one setting the tempo and since I knew I was close to orgasm, I built up a quickening pace of thrusts into her ass, pushing harder every time. Rachael gasped and moaned, loving every minute of it. I reached my hand down and began playing with her clit again, shoving three fingers in and out of her tight, wet pussy. I felt that familiar sensation in my balls again, and thrust into her hard one last time, shooting my hot load right up her ass. She must have felt it in her because she cried out in a loud pleasure scream that I knew SOMEONE must have heard.
We were both out of breath, and when I felt my dick softening, I pulled out of her. We lay on the couch for a few minutes, kissing and touching each other, until Rachael said she had to go.
We both got dressed and I walked her to the door.
“I have total confidence in your skills Mr. Simonds. I hope you will accept me as a client,” Rachael said, kissing me on the cheek.
“Well, after that convincing argument, I would be a fool not to,” I replied, smiling.
I watched her go and then shut the door to my office. Sitting back in my
chair with my hands behind my head, I breathed a sigh of relief.
“I think things will go just fine out here,” I said to myself.

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