Itroduction: A Player

Sometimes you live your life sure of how things are. When you are kid they tell you all kinds of stories about how you get what is coming to you, or those stories where someone if made to be the person that you were mean to or overlooked. As you get older, you realize how much of that is bullshit.

Right?

Well, My name was James. Not Jim, not Jimmy, not Jamie, James. My mother always called me her little Jamie and doted on me and crap and I could not wait to throw that yoke off. I had grown up with no father, as the man that fathered me left when I was 3. I have no memories of the bastard and want none. I was an only son and I was my mother’s whole life. She hovered over me and I never wanted for anything. She always told me what a wonderful boy I was. Somewhere in my life I took it to heart, that I did no wrong. In high school, I never talked about my sexual conquests with the other guys my age. This was because I was actually having sex. The drill team colonel rode my cock every Wednesday afternoon, one of the cheerleaders sucked a load from me on Thursdays, and I fucked Ms. Herron in her car on Tuesdays. There were, of course the indiscretions between those regular moments, but all of the women and girls told me how wonderful I was.

I was pretty sure that I was just that good. My mom and all these ladies agreed, so how could it not be true?

I never really wondered why Ms Herron vanished between my Junior and Senior year. I broke up with the cheerleader Senior year by telling her she really would be better with bigger tits, and the Drill team colonel I got rid of at the end of the year by letting her know I thought her ass was getting a little too fat. I had a scholarship out of state and the last thing I wanted was tearful calls to know if I was fucking other people, because I planned on doing a lot of it.

And I did. I passes a few harder courses not because of fucking the professor, because I had most men for my courses in business management, but their wives enjoyed having my eager and willing cock enough to help me out where they could. 

I have to say that graduating college at 22 with an MBA and a cock that had been dipped in most of the good wells around town, life was good for me. Because I have done so much so fast, I always had help from a girl who thought I was going to fall in love with her to get through two college degrees as fast as possible, business’s were throwing offers at me and I was lapping up the parties and schmoozing. I did more fucking when talking to the Southern California companies, but I had to go with the best opportunity and that was NYC, of course.

Within a year, I was climbing the ladder and into more than a few pairs of panties. Never anyone that worked under me, but if you are negotiating with your cock deep in your opposition as she moans, you are in the power position.

And that is how I rolled, as they on the streets. I was happy, unfettered and absolutely sure of how wonderful I was and that my life was laid out on golden paved streets until I died.

Chapter One: A meeting.

So when I got the invitation to my five year high school reunion, well I felt bad first because I hadn’t talked to my mom in a couple of weeks. I tried to call her at least once a week, but I had to call her going to a meeting, or a date, or getting my pants back on. Still she had to be happy to hear from her only son, right? Anyway, I got the invitation and decided that while I would love going to show them all how I really was better than they were, I just did not have the time to meet with people that did nothing for me in my life.

You see, we all do things like this. We get so wrapped in our own lives we don’t think about how our decisions radiate out and affect so many others.  I know that now, but getting to why will take us a while, so just stay with me here, okay?  Great!

So there I am in New York City, in a power tie being a power player, dating models, fucking them silly and leaving as soon as they nod off to sleep. I was happy.

And, I was oblivious. I really had been all my life, but I am getting ahead of myself again. I never thought a bit about the reunion until the night it happened. 

Way back home along the western Gulf Coast that night, a meeting was taking place. It was not a meeting I would have given a rat’s ass about and knowing it was taking place, I would have laughed about it. My mother lived in the same little teeny house I grew up in, I figured she was happy there, why disturb her? Three cars had pulled one after the other into her drive way. Doors opened and women got out. One stopped and moved to her rear door.

In New York City I came home as midnight approached, smelling of the awful perfume my female competition preferred and her pussy.

Four women, one holding the hand of a small boy stood on my mother’s porch and rang her doorbell. My mother answered the door and looked over each of the woman then stepped aside and let them all into her home later than she had ever received guests. She closed the door behind herself. As my mother met her grandson for the first time, my phone rang with one of my regular fuck buddies outside my building in nothing but a fur coat and a raging case of hornies, I was good for another round and wondered how she would like the taste of Kaityn’s pussy on my cock. I called the doorman to let her up. My mother talked to another mother and her just High school graduated daughter. Kaitlyn seemed to want to taste my cock more than she ever had before and it made me smile, my bet was she was at least bi and had no idea.  Maybe I could help her out. In my mother’s living room, they all listened to the last woman, scarred and disfigured and sick from bad plastic surgeries. All of the women were crying now, the five year old was fast asleep on his mother’s lap. I was falling asleep in Kaitlyn’s breath slow and even across my skin. A good cum does that for you.

My dreams were never really too vivid for me and I very rarely remembered them. This night was different. I saw a group of woman with red eyes gathered around a pot and my mother, a Deveraux by birth, putting strange items into a big pot. A photograph went into the pot and the women all said something. A clip of hair, the something repeated. The ritual went on and in my dream I could see a purple glow start from the pot. Then the dream changed, as dreams do, to the outlines of a man and a woman in bed. The man was restless, as if he was having a bad dream. The woman’s head rested on his stomach and the satin sheets, good ones like I had, shot up over his loins as if his cock had erupted into an erection. He groaned and shifted and she tightened her hold on his waist in her sleep. I was having a dream about a man having an erection in his sleep?  I was looking around for the scene to change when the man’s body, save for the outline was engulfed in a dull pulsing purple light. Well, this seemed a little interesting to my dreaming mind, more so that a bunch of women chanting around a chili pot. The outline pf man began to change, his body lines seemed to be flowing, his body shortening, his square shoulders narrowing, his hips flaring, his waist growing narrower. I wondered what the hell kind of dream I was having and why? I looked over his outline again and I got a laugh. In his light thrashing on the bed the satin sheet had gotten pulled up and the outline of his erect penis under them was gone. So much for his sexual potentancy. The purple light faded from the man’s body and I felt a little aroused and mostly amused. Thank God that some things can only happen in dreams, I wanted to stay in the dream to find out what the woman would do when she woke up and found herself in bed with another woman then rather than the man she had fallen asleep on. The trouble was something was tugging me to wakefulness.

 An Interlude

That something was my bladder and I had to pee so bad it hurt. I slipped out from under Kaitlyn carefully. Here in my own apartment, I didn’t need a light to move around, I would need one to pee, or I could sit down. Since the place was pitch black in the wee hours of the morning, I decided to sit. I nakedly padded my way into the bathroom and took a seat on the commode. It took my sleepy mind a minute to recall what I was to do. When I started to pee I almost cried out because the warm flow went all over my thighs. I chalked it up to going to bed after some great fucking, and fumbled in the dark for some toilet paper to clean up with. I wiped up my thighs and then up along my crotch. I yawned hugely as I wiped inside the soft folds and jumped, completing the wipe with a bit more caution. I padded my way back to bed and crawled back into bed beside Kaitlyn. She smelled really nice.  I wondered why I had never noticed and her hair looked lovely but it felt… damaged like she over treated it. It was funny to me the things women would do to attract us men. My stroking her hair made her turn back over and lay her head on my lower abdomen and then laid her arm up at an angle with her hand resting on and around the full mound there.

It was a nice feeling and I fell asleep hearing a soft moan from Kaitlyn.

Chapter Two: A Shock

I drifted out of sleep feeling as if I had been asleep for days, knowing it was just an after affect of a really good fuck session. I stretched languidly. I had the most delicious feeling between my legs. Kaitlyn was giving me head again. Now she was tasting her own pussy, she had to be lesbian. I did not even bother to open my eyes as I moaned and spread my legs more. I had no idea what she was doing down there but the feeling was like an electric charge from between my legs. I didn’t know how she was doing it but she was making it feel as if her tongue was right under the skin. It felt so good and I wanted her to keep it up until I exploded in orgasm. I felt as if my skin was a live and there was a growing pressure deep in my belly from the fluttering warm sensation inside me brought on by her tongue. It was making me gasp and writhe, wanting to both pull away before it killed me and to press closer for more. I could hear her moans from an open mouth. I thrashed my head as her tongue moved over a spot and it seemed to set all my nerves singing with loud pleasure, and almost as if I could feel each taste bud on her tongue. The air was so different from the warmth of her crouched between my spread thighs as it passed over my nipples which seems almost like just exposed nerves on their own. I cupped my hands under my breasts and ground down on her tongue as the sensation got to be too much and I began to shudder in spasms of orgasmic bliss. I have never cum like this and her tongue dragging over the swollen lips between my legs was making mini-little orgasms through me. It felt like I would never stop cumming. I had never had an orgasm go on for so long nor feel so intense. My hands were kneading breasts in moaning ecstasy, when I heard Kaitlyn’s voice in a husky whisper over me. “I can’t believe he brought someone else to bed but I am so glad.” I felt her drag her self up between my legs and the feel of our pubic mounds rubbing together sent me into another wave of pleasure. “Still can’t believe I let that bag of shit fuck me when he changes his credit cards, but it sure is nice to have someone as sexy as you to wake up to.” It dawned on me that the bag of shit with the credit cards in question was me! This bitch was stealing from me, she was the one using my freaking credit cards! My eyes snapped open as I intended to tell her to get the fuck out of my apartment. My words were cut off by the soft way she drug her smallish breasts over my nipples and it made me moan. “Are you in love with James, ‘cause you need to come out of here with me if you are sexy.” A hand cupped around the soft full curve on the right side of my chest and a sudden new more alarming dawning crept over me. She was cupping MY breast, my hanger, my jug, my TIT. “I’ve always had a thing for girls with nice big breasts, but it isn’t cool to admit that with the girls around here.  Liberated dykes can’t be honest.” She was rubbing her MONS VENUS to MINE! I suddenly felt a rush of panic. My name was James and I was a man with a thick cock that the women could not get enough of !  Well, except for Kaitlyn, she, apparently, was a lesbian that had been living off my credit cards for over a year and who found fucking me a disgusting act but better to hold my cock than a gun. She tilted her head as a hand slid between our bodies. “You first time, honey?”  I felt her fingers rubbing my pussy and the sensation of her rubbing across the lips of MY pussy was more than I could have ever imagined. I had spent my life getting a woman wet so I could cram my dick into her and now I was feeling just how good it was to just be touched, a warming and deeply pleasurable without rushing headlong to the “big O”. 

“Yesssss.” I found myself answer completely honestly as I angled to feel more of her hand only to be made to moan when she slipped her finger into the canal of my vagina. My vagina, that was going to be hard to accept but right now, it just felt good, and quite different than I had expected it to. As a man, I always had a concept of how my cock felt going into a woman’s pussy. Now I will provide that this was just a single finger, but most of the sensation I felt was at the finger sliding into me, right at and around the opening of my pussy. As her digit pushed deeper there was just a slight feeling of pressure, of fullness, and it was a nice feeling to have.

“It don’t make you dyke yet, honey, but trust me, it is better than men.” She murmured to me as I ground to feel more of her finger and stopped when the delicious, slight, and nice feeling of pressure turned into a sharp pain. Kaitlyn pushed her finger to that point again and I sucked in air through my teeth as my body moved off her finger hurriedly. “Christ!  A virgin! What is James doing with a virgin in his bed?!?”

Chapter Three: A Confessing

“Kait,” my voice was strange to me and yet not, just like the changes to my body.  “I am James.” She looked at me with wide eyes, then they narrowed and really studied my face. 

“This ain’t possible” She said through clenched teeth.  “You are his sister or something but you are not James.” She had a point there; I was not James, at least not anymore. I got out of the bed and paced around the place trying to think, as I was in a real shit storm now.  All of my ID all my credit cards, it was all for a man that, by the weighty bounce brought on by my pacing around, I was not anymore.

“I don’t know what the fuck is going on here, I have to be having a really bad dream, but I am James.” Then it occurred to me that I was asking for understanding from… “You were fucking stealing from me you whore!” I was livid all over again. I started to get madder as she started laughing. “What the fuck is so funny?!?!?!!!”

“You lived your life thinking you were god’s gift to women James,” She started getting dressed. “Using women like fuck toys and then tossing them aside, baby.  Now you are a woman. Look me up when you are ready to be jump of the GW bridge and we’ll talk girlfriend.”a