This is my first attempt at posting one of my stories. Please be kind. I've never let anyone read any of these before, so I'd love it if you sent me an email at email@example.com and let me know what you think. This first chapter is mostly lead-up, though I have many more chapters already written. Thanks for reading - Verytas
The first thing I need you to know is that I think I love you, too. But I also need you to understand how much that thought terrifies me. The only thing love has ever gotten me was hurt, and I swore to myself that I would never let myself get hurt again. I promised myself I’d never fall in love, then I would never again have to feel that sort of pain. Then you came along and... Fuck! Why do you have to be so wonderful, so fucking perfect? Why can’t I get you out of my mind? Why can’t I force myself to just forget you, like I’ve forgotten countless others over the years? What makes you so different? The only thing I can think of is that I’m falling in love with you. I can’t help it. I’ve tried everything to stop it from happening. It’s always been easy, before you. When things seemed to be getting serious, I could always find some reason that it wouldn’t work. There was always something I could pick-out about him, something wrong, something to hate. Then you came along and... Fuck! I made a promise to myself, never to let this happen again.
I had a shrink once tell me that our feelings are simply there, that we have no control over them and therefore, we should never regret them. I thought she was full of shit. But now, I’m starting to wonder if she was right. She also told me that it would make me feel better if I opened-up and talked about my feelings. I told myself that was a bunch of shit too, even though I knew she was right. There are things I’ve never told anyone. Things I’ve been ashamed of for years. Things I’ve tried to forget, and even though I was sometimes able to fool myself into believing that I had, I never could. And for some reason, the more I’ve gotten to know you, the more I’ve been thinking about my past. Memories that have been buried-away in the deepest, darkest, dustiest parts of my mind for over twenty years are resurfacing. Oh sure, they’ve popped up here and there over the years, however it’s never been too much of a problem to shove them back down and lock them up. But then you came along. At fist, I thought that you just reminded me of someone I used to know. Someone I thought I loved. Someone I thought loved me. But the more I think about it, the more I’m realizing that you aren’t anything like him. Well, that’s not entirely true. I can’t deny the similarities, even if it is easier to focus on the differences. And the biggest difference is that I actually can tell that you care about me. When you told me you were falling in love with me, I believed you, I honestly and truly believed you. When he first said that to me, while a part of me so desperately wanted to believe him, that in a way I did, I still had my doubts. At the time, I chalked it up to my horribly low self-esteem. I didn’t love myself, so, I reasoned, how could anyone else love me. Not too much has changed in all these years. Right now, I’d have a much easier time telling you that I love you, than I would telling the same to myself. Although all these years later, I do know that I’m not completely worthless. It might be uncomfortable to tell myself, ‘I love you.” But I usually don’t have much of a problem saying, “Hey, I really do like you.” I’m working on it, and one day I’ll be there.
This letter is actually a part of my healing process. That shrink also told me that I should write about my past, even if I never showed it to anyone. Again, I thought she was full of shit. Yet here I am, pen in hand and two paragraphs on the page. Whether or not I’ll ever give this to you, well, time will tell. I’m not even sure what all I should put down here. I mean, memories are flooding back to me by the minute, hell, by the second. Things I haven’t thought about in years, hell, in decades. I’m not sure if my mind has ever been this chaotic. There’s only ever been one point in my life when I wondered if I was headed for a nervous-breakdown. I’m feeling that way again. The difference between then and now is that now, it’s happening at the beginning of the relationship. Then it was as the relationship was ending. In fact that was at that point when I realized that I was not completely worthless, and decided not to kill myself.
Now don’t get me wrong, I’m not feeling suicidal. Even back then, I had thoughts, but I don’t think I ever could have done myself in. I considered lots of different things. I was in a bad situation and I knew I needed to get out, away from him, but it took me years to realize that. Three years, actually, and another nine months before I got out. I did a lot of things in that time, and not all of it was bad. It was a classic roller-coaster ride. There were both high and low points. And at first, there were more highs than lows, at least that’s how I remember it.
I remember the first time I saw him, like it was yesterday (although the older I get, the more I feel like I can remember yesteryear much more easily than yesterday). He was, well, he was tall dark and handsome, even if he leaned more toward the more the rougher side of handsome. He was also, in my eyes anyway, grown-up already.
Ok, with that line, I suppose I have to get to the real truth. When I sat down to write this, that was the one rule I made to myself. Be complete honesty. After all, if I decide not to give this to you, then there’s no harm done. But if I’m not honest with myself, then I know I never can be with you, or anyone for that matter. Maybe I will burn this when I’m done with it. Maybe I won’t. I’ll decide that when I’m finished. In the meantime, well, now I realize I’m, stalling. Like I said, there are things I’m not proud of. The first of which, is saying that I was thirteen when it all started. He was four years older, and at that age, there was a much more pronounced difference between us. I still saw myself as a little boy and I saw him as a man. His name was Sam. And he was, well, shit, I don’t even want to put it down on paper, it sounds so bad, but I’m being honest here... He was my step-brother. I know I told you about growing-up with my mom and step-father, and I also know I’ve never mentioned having a step-brother. I’ve never told anyone about Sam, not in a long, long time. And even when I did mention him, it was only a quick, shallow comment.
His father and my mother had been married almost a year, when it started. In that time, I developed quite a crush on Sam. He barely seemed to notice me. He visited every-other weekend and spent a couple weeks at our house during the summer. I saw him as everything I wasn’t. He was big, strong, smart and funny and confident. I was the epitome of a ninety-eight-pound-weakling. I always felt different, awkward, and it was rare that others found the same things amusing that I did. By the time I first met Sam, I already knew I was gay. I’d figured that out a few years before. But knowing something and accepting something are two completely different beasts. The only time I seemed to feel completely comfortable with myself was when I was alone with my thoughts, in bed at night. You know that I’m more of a night-owl, than a morning-person, and I have been for as far back as I can remember. I used to spend hours laying in my bed and thinking. And while I thought, I played with my dick. When I was real young I just played with it. I didn’t know anything about cum or climax. It just felt good to touch myself down there. That all changed soon after I turned ten. One night, I didn’t stop when everything started to feel all tingly, and even though I was terrified I was going to piss myself, I kept my fingers moving and... I’d never felt anything so incredible. I don’t remember how many times I got myself off that first night, I just kept at it until my dick was sore and I was so tired I couldn’t stay awake any longer. The next morning, I realized I’d rubbed my dick raw and that night, I discovered (necessity is the mother of invention) how to use spit and lotion for lubrication, as I rubbed my sore little dick. I was still too young to actually shoot cum, sometimes I produced a small amount of clear drool. By the end of the year, however, the clear drool had turned cloudy, and soon after, it would pump out in big globs. And by the time I really started shooting cum, I also discovered that thinking about sexy things made it feel even better. And quite soon after that, I realized (not surprisingly) that thinking about sexy things involving other guys was better than thinking about girls. I tried, once in a while, when the guilt was, for whatever reason, really bad, to think about girls when I jacked-off. But even then, when it came right down to it and I just couldn’t push myself over the edge, I’d think about another boy and shoot.
I know I’m kind of wandering here, I started that paragraph with every intention of getting into what happened between Sam and I, and ended it jacking-off. There are just so many things running through my mind right now, it’s hard to focus on any one. I guess the point I’m trying to make up there, is that I started fantasizing about Sam a year before anything ever happened. So by that first time, I’d already imagined, many, many times... Well, it wasn’t the same as what I imagined. Although, there were times... Shit!
Another thought just popped-up, something I think I should mention, before I really get started. I do remember masturbating and fantasizing about both being forced to do things to other guys, and forcing other guys to do things to me. And even then, I had a rationale for my nasty fantasies. Classic gay-repression. You remember what it was like, back when we were kids. You heard the names thrown around by the other guys, ‘Faggot,’ ‘Queer,’ ‘Cocksucker,’ and do you remember the way those words were used. I knew that’s what I was, but it isn’t who I wanted to be. Only at night, alone with my thoughts, could I be who I really was. To be truly exciting, to get myself off hard, I had to believe my fantasy could be true. And I had a hard time imagining that most of the guys I fantasized about would ever be attracted to me (that whole low self-esteem thing again). So, I remember some of my earliest fantasies, after hearing in history class about how back in the day Slaves were forced to do anything, “...and I mean anything they were told to do.” Now don’t get me wrong, I’m not one of those kind of people, I was a confused boy who fantasized about having a slave to suck his dick. I also fantasized about myself being the slave, and being forced to suck my master’s dick. Not all my fantasies were like this. I could believably imagine myself and some fantasy partners cuddling and kissing, making love, as opposed to fucking. But there were certain guys, most of them bigger and stronger than me, men rather than boys, who I could only believe would want to use me, after all I certainly didn’t have anything to offer them, other than a couple hot, wet holes. Just like there were other guys, usually smaller and weaker, who I’d imagine forcing myself on. Sam was big and strong and so (in my eyes anyway) manly, that I’d imagined him raping me dozens of times before it ever happened.
There, I said it. Sam raped me. But, I think it really was what I wanted. I’ve wrestled with that idea for over twenty years, giving it way more thought than I’d like to pretend. While I often do wish my first time had been different, there are other times when I wouldn’t have had it any other way. And the older I get, the more I can see the relationship from Sam’s point of view. Even though I saw him as grown-up back then, I now realize that he was still almost as much of a boy as I was. I’ve often thought about what I’d do if out roles were reversed, I was the older and he was younger, and I caught him doing what I was doing...
Ok, I know, I have to get to the story. So here goes. And if you actually do end-up reading this, know that this is the hardest thing I’ve done in ages. I know I could never actually speak the words to tell you this, but maybe after writing it all down, and assuming you do read it, maybe I’ll be able to talk about it. But, please don’t expect too much, at least not at first. It’s going to take me a while to assimilate the fact that another human-being knows these things about me. It is a big-deal for me to put this much trust into someone. Ok, now on with my tale...
It was a Friday morning late in the Fall I feigned illness so that I could stay home from school. I knew that Sam was going to be visiting that weekend and I figured I could spend all day Friday jacking-off and hopefully wear myself out, so maybe I wouldn’t be popping little boners the whole time he was around. I went into my parent’s room so that I could sneak a peek at some of my step-father’s porn-mags, which I’d found hidden in his sock-drawer. Though most of the magazines he had showed only big-breasted women, there were a couple that had naked guys along with the girls. Those were the ones I liked the best, as I could stare at the guy’s tight, muscular bodies and their big, hard cocks while I jacked-off. So while I was searching through my parent’s dresser, I opened the drawer where my mother kept her ‘unmentionables’. And for some reason, looking at all the sheer, lacy undergarments made my already-fairly-stiff little dick become hard as steel. I really didn’t think about what I was doing, as I pulled a pair of panties from the drawer (they were pink with a bit of white lace around the hems) and felt how soft they were in my hands. Then a thought crossed my mind. The silky softness felt great against my fingers, I had to wonder how the satiny fabric would feel on the hot skin of my stiff little prick.
Well, it felt incredible. And before long, I’d stripped-off my shorts and t-shirt and had put on my mother’s panties, as well as a pair of her nylons and one of her bras. I don’t know what had gotten into me. Ok, so my hormones were going wild and it seemed anything at all could make me horny. I could make my little hard-on twitch inside the silky underwear and it felt almost as great as it did when I stroked myself. I was a bit small for her clothes. They hung off my body somehow, though quite baggy. It wasn’t even noon yet, and I knew that my parents wouldn’t be home till well after five o’clock, so I figured I had several uninterrupted hours alone in the house to play. After choosing a short skirt from the closet, and a sheer blouse, I found a pair of high-heels to complete my outfit. I stared at myself in the mirror and became even more turned-on than I think I ever had been. Other than my short-hair, the beginnings of an Adam’s-apple in my throat, and the obvious bulge tenting in the front of the skirt, I could almost imagine myself as a girl.
Now, before I go on, I have to say that while I had wondered what it might be like to be a girl, it was almost always when I was fantasizing, wondering what it would feel like to be fucked by a man. Like I said, I had some bizarre fantasies as a kid. I wondered what it would feel like for a girl to have a guy between her spread legs, his big cock inside her, humping and pumping and... But that was just my thirteen-year-old mind trying to figure-out the ways of the world. Even though I sort-of liked the way I looked, and I know I loved the way I felt, wearing women’s clothing, I honestly never really imagined myself as a girl.
But the boy in me sure as hell was turned on my the image in the mirror. I could almost imagine trying to seduce the image, the girl I saw in the mirror. My dick was as hard as it ever had been. It felt so incredible throbbing against the sheer material of the panties I wore. And after a moment or two, I had to close my eyes and think about my math teacher, a mean, old, ugly hag, who’s image never failed to soften my little erection a bit. By squeezing the right muscles and taking active control of my breathing, I was able to stop the tingling that had started deep in my belly. And, well, I also thought about how I’d clean-up the mess, if I spurted inside my mother’s panties, so that she wouldn’t ever figure-out what I’d done. No longer able to stare at myself in the mirror, I went downstairs, almost tripping on the steps in the pair of high-heels I was wearing. After I made sure that all the curtains were closed and no one could see into the house, I decided to fix myself lunch.
It was strange. I mean, there really is no way to move around in a skirt and heels without feeling a bit feminine. I sat with my legs crossed and sipped my milk with my pinky-finger extended. I took little girlish bites of my PB&J sandwich and chewed each one carefully. My hands moved with an over-exaggerated flourish and I giggled while moving and shaking my head, pretending I had lots of long hair to toss around. After I finished eating, I wandered around the house, trying to get used to walking in heels and feeling the soft garments slide against my skin as I moved. I was also trying to keep myself from touching my dick for as long as I could. I still had at least four hours before anyone would be home, and I didn’t want to wear myself out too soon. But it was becoming more difficult by the minute, knowing that I probably had three or four good orgasms in me, I’d have to pop the first load at some point. Still, I also knew that I was more excited than I could ever remember, and when I did get myself off, it was going to be more intense than any time before. I knew that the longer I wait before making myself come would make it even that much more intense. And I also knew that once I’d shot my wad, I was sure to fall into that guilty-funk I always did, when I made myself shoot a big load (though I knew I’d get over it quickly, I still didn’t like laying there with semen dripping down my body, lying to myself, swearing over and over that I was going to start fantasizing about girls instead of guys).
My dick never got soft, as I walked from room to room, feeling more and more like a girl as I did. Like I said, I never wanted to be a girl. But being dressed like one, wandering around the house in a skirt and heels, well, it really turned me on. Every time I saw my image in a mirror, or reflected in the blank tv screen, I felt a throb between my legs. It didn’t take me long to realize that it was easier to walk in the high-heels on the kitchen’s smooth linoleum than on the carpet covering the floor in the rest of the house. However, there wasn’t a whole lot of space in the kitchen, so I got bored quickly. Then it hit me. The only part of the house where I hadn’t meandered was the basement, with its open, smooth concrete floor. The wood stairs leading to the basement were easier to get down than the carpeted stairs leading to the second-floor of the house. And when I heard the echoing click-click-click as I walked across the floor, well, I had to think about my hag of a math-teacher for a minute, to keep everything under control.
It was a full, open basement, with lots of boxes and furniture and stuff stored along the walls. With all my mom’s stuff and all my step-father’s stuff moved into the one house, there wasn’t enough room upstairs for everything, so the rest was in the basement. I was getting better at walking like a girl, as I moved around the big, open room.
When I first saw the box, with my mother’s name on it in black magic-marker and underneath written, “Old clothes,” I felt my stomach flip and had to squeeze tight between my hips to stop myself from getting too excited. I tore the box open and just stood back looking at my find and trying to keep my body under control. I decided that considering my discovery, I should go back up to my parent’s room and take-off the skirt and blouse I was wearing, then come back down to the basement, and pick a new outfit from the box. I knew that when I finally did get myself to come, I’d surely spray my load from here to Kansas, and everything near-by would be coated in spunk. I couldn’t get cum all over the clothes I was wearing without having to clean them, so mom wouldn’t find-out. With these clothes, however, it didn’t matter, she’d probably even forgotten they were down there.
That decision paid-off in a few different ways. Firstly, these clothes fit my mother before she’d put on a little weight. The outfit I’d taken from her drawers and closet was rather baggy on me, but everything in the box seemed to fit me perfectly (well, except that I had nothing to fill the cups of the bras). The first thing I grabbed was a skimpy, little pair of red panties and slid them. There was barely enough material to them to cover my balls and hard dick. The bra I picked was black, and it took me a while to figure-out how to clip it. I dug a bit deeper into the box and pulled-out something that was made of sheer, almost-see-through, ivory satin, that felt so incredible against my fingers, it only took me seconds to step into the slip and pull it up over my body. I’d never felt anything like it. I decided to not think about my math-teacher and see what happened.
I found a pair of thigh-high nylons that had a few runs in them, but it didn’t matter to me. In fact, I put another runner in one of them with the nail of my big toe, as I realized you couldn’t put them on like a pair of tube-socks. In another box I found some old shoes, purses and (I couldn’t believe I’d forgotten about them) three old wigs my mother used to wear. Within minutes, I was going back upstairs wearing the panties and bra (the cups of which I’d stuffed with two silk scarves I found), the thigh-highs and the slip, as well as a pair of heels (with about another inch of heel than the other pair I’d been wearing), a long blond wig on my head and a pair of white gloves on my hands. And for some reason I grabbed an old black purse, which I tucked under my arm.
The first place I went was to the first-floor half-bath/laundry-room which was the only room on the main-floor with a full-length mirror. Other than the obvious bulge between my bony hips and the slighter bulge below my chin, I could have passed for a girl. I liked the way the high-heels made my legs look. The my calf and thigh muscles were forced to flex a bit, and I turned to see that my butt was more shapely with the heels on my feet. I shook my head and felt the long hair on my shoulders and upper-back. I walked back and forth, as best as I could in the small space, staring at myself in the mirror and finally, allowing myself to touch my hard dick, although only on the outside of the slip and panties I wore. I was so horny I knew that if I really wanted to, I could make myself pop within half a minute. But that wasn’t what I wanted.
It was a little after one o’clock. I figured I had at least four hours left before anyone got home. So if I played-around for three hours, that would give me an hour to clean-up and make sure I left no evidence of what I’d been up-to. I was a bit shocked to see the wet-spot form through the panties and slip I wore, more surprised that I hadn’t started leaking pre-cum earlier. Watching the spot grow, the red from the panties becoming even more visible through the sheer satin slip, made me even hotter. I pressed my hips forward a bit so I could get at my balls a bit better and rubbed them, occasionally stroking one hand up the shaft of my dick, forcing more clear pre-cum from the tip of the head. Before long, my dickhead popped out of the panties and within a few seconds the sheer fabric of the slip had been saturated. I my little dick-head was almost as red as the pair of my mother’s panties I wore.
I went for as long as I could without touching my dick. But when I finally did, it took a minute or so before I exploded. It was the best orgasm I’d ever had. My legs got so shaky that I couldn’t keep my balance in the high-heels, so I had to support against the washing-machine. I watched myself come in the mirror, the wetness spreading all over the slip and panties I wore, soaking through the sheer fabric, wet and gooey.
It took a while for me to get my breath back and I decided to go up to my bedroom for the second-round. The high-heels were hurting my feet and, while I thought about taking them off, I remembered hearing girls always talking about how badly their shoes hurt, so I figured I’d suffer too. My legs were still feeling a bit unsteady, and I took my time going through the kitchen, knowing that the carpeting in the next room was more difficult to manage in heels.
I’d taken three careful steps over the carpet when I heard a voice and nearly shit myself.