A Diamond in the Rough

A few years ago my life was turned upside down by the worst scenario I could imagine. My father died of a heart attack at 46. That's right 46. It was a shock to everyone. He was in good shape, ate well for the most part, and aside from a little extra weight, was a fit, healthy man as far as we knew. That little idea was shattered of course when he passed suddenly one night.

Now, it was just my mom, my brother and I trying to cope. Times were hard. We had some money from his life insurance, but it was just enough to make it so we weren't totally struggling. At the same time though, college seemed like a foolish dream without me working my ass off for most of my senior year.

I worked six days a week to get enough to cover what I had to pay out of pocket despite the huge loan I had to take out. That being said, I did it. I got into college, and had some money to spend, not much, but enough to eat. Mom was proud that I was able to work around my financial problems and keep up decent grades. I wasn't the valedictorian by any means, but I did well.

The world however doesn't give out any "hard worker" awards and an animation degree didn't have the lucrative income I was hoping. Not straight out of school anyway. So there I was, 24 with a degree and a massive debt to prove it, living back at home with my mom and little brother. Not the best situation I could've hoped for. For the time being though, I had no other choice. I did manage to get back with the company I worked with as a teenager and even got a manager position. It was the most I had ever made and I was just pleased to make my first loan payment. Again, not the best situation, but it could have been worse I suppose.

My brother, for an example, was out of high school now, and had been working in retail for the last year. No aspirations for college apparently. He didn't have quite the same drive in the face of adversity that I did. If something seemed too hard, he would look for an easier avenue. To an extent, I actually envied his "why take the path of misery" attitude. I mean, he'd worked long enough that he had some money saved up, nothing that would get him an apartment, but something saved nonetheless. Plus, he had no debt. In fact, the more I think about it, the more it seems he may have been the smarter brother.

Overall he was a good kid. He use to get picked on a lot and I think it may have hurt his confidence quite a bit. I tried to look after him as best I could, but, being 5 years older than him, there were only so many instances where I was actually around to watch his back. He was one of those smaller kids. You know, the type of kid that's skinnier than the other guys, not athletic at all, an easy target for the alpha males. I know high school was rough on him. He never had a girlfriend and wasn't the most out going. Oddly, he had lots of girls for friends. He actually seemed rather popular amongst them, but never got any dates. I always thought that was odd. I figured once I moved back in, since he was older, we could hang out a bit. Maybe I could help him get a date or two under his belt. The big brother in me I guess. I suppose I wanted to "protect" him again in a sense. Bring a little bit of normalcy back into my life while I figured out what the hell I was going to do about my bills.

So there we were, all the kids at home, with a doting mother making us dinner. It wasn't great, but it was better than nothing. So one night we're all eating dinner, mom, as usual, whipped up some chicken dish, rambling on about our days. After dinner, mom straightened up real quick and told us she had to get to bed early because she had to leave early for work. I took the time to try and catch up with my brother. We all ate together pretty often, though we didn't have a ton of time to do the whole brother thing with us both working a lot.

So we start off with the basic chit chat. I asked how things had been with me off at school, that sort of thing.

"I've been pretty good for the most part. Mom actually started seeing someone for a little while."

"Wow, I assume that didn't go so well" I responded.

"Well enough I guess. I just don't think mom's ever really gotten over losing dad."

"Yeah, it was a shock to everyone. I don't think she's ever really going to be able to deal with that. So how have you been?"

"Pretty good. Managed to graduate, and I have a job, so things are better than they could be."

"Yeah man, I'm glad you got yourself working after school so quickly. It's easy to finish school and just get stuck doing nothing."

"Well, I'm not lazy, I would rather just make things relatively easy on myself" he said with a laugh.

"I'm starting to think that's the best way to go. I got the debt looming over my head and I'm in no better situation than you are. Shit, you're probably better off actually."

He chuckled and got up to clean his plate.

"So, have you found yourself a girlfriend?" I asked.

"Uh, no actually. I haven't bothered to look I suppose."

"Well, I'm sure you'll find someone." I got that answer I thought. At least he didn't seem too broken up over it. I guess there just wasn't much aspiration in it for him.

With that I got up to clean my plate and we had a bit more idle chit chat before leaving the kitchen. We sat in the living room for a bit watching TV, laughing and joking around, but the looming responsibilities of the following day started to fill our heads with thoughts of obligation and we shuffled upstairs to our respective rooms. I however had no intentions of going to sleep. It had been a couple months since I had a girlfriend and my prospects for getting laid weren't the best, so I switched on my computer and searched the net mindlessly rubbing my dick until I could find something satisfactory.

I was never one for the mundane porn. I always liked more off the wall stuff. Porn for me was like a drug. I found thing I liked, jacked to it incessantly, then got bored of it and had to find something more. From soft-core to hardcore, girl-girl to girl-girl-guy, midgets, gay, shemales and all sorts of fetishes in between. Short of illegal stuff, I had basically seen it all. I would rub my flaccid dick until something was kinky enough to rouse me. It was sort of like a treasure hunt in a way. I would poke through dozens of thumbnails seeing what the internet had to offer. I would always find something, but the severe lack of physical contact was taking its toll. I opted for the personal ads eventually.

Now I had never actually gone through with any of casual encounter stuff before, but I was getting desperate and the pics were quite useful from time to time. Just knowing that it was a real person on the other side made it a bit more fun for me. Eventually this too would become old hat. I didn't often do more than some erotic chat with most of these people, but girls became mundane, and my need for something more took over. I decided to take a shot at looking up the transgender/CD profiles. This was brand new ground for me. I had jacked it to trannies before, but this was different. This was the possibility of actually fucking a chick with a dick. The thought was incredible, and kept my attention for a while. There were also a surprising number of profiles to look over too.

On one fateful night, that would rock my world for a third time in a few short years, I came across one profile that stood out like a sore thumb. It took a while to figure it out though. The "woman" in the photo was slender, pretty feminine overall, easily passable and hot enough to get me hard. There were four photos. In the first, she was wearing a short black skirt, ending just under the ass from what I could tell, with a black undershirt covered by a green button up shirt knotted over her stomach. Her eyes had a black bar over them, which kind of obscured the rest of her face, but he body was looking really good.

The second photo was similar. This one was from a different angle though. What an angle it was. She had her back to the camera, bent over slightly with her hands resting on what looked like a counter top. She looked back over her shoulder seductively, though her face was obscured a little again by a black strip over her eyes. Her body, yet again, was the star of the show. Her skirt was short enough that in her position it came up just enough to give a peek at her ass. I could see two little mounds peering out from under her black skirt. Round and full, her ass was quite a sight. Covered only in a pair of green boy shorts that hugged her beautifully, her ass was the hottest thing I'd seen amongst the Transgender/CD profiles. I was steadily stroking my cock at this point wishing I could see more. This girl knew how to tease.

The third photo was hotter than the one before. She was now sitting on the edge of the countertop. Her back arched pushing her tiny chest up. Her boobs, as tissue filled as they may have been, were prominent here. Her arms fell behind her, bracing herself and assisting the position of her boobs. Again, she knew damn well how to tease. Perky, her tits were up for display. That's when my eyes traveled down her trim body to see where that wonderful skirt of hers rested. A rush of blood to my dick, and a faster stroke followed as I saw her slender legs slightly parted. Soft, long, and just curvy enough to earn a place amongst any leg fetish gallery, they were a delight to imagine clenched around my body. That however, wasn't what I wanted to see. I wanted to see just how large the bump in her boy shorts was. You can imagine the anticipation as my eyes travelled back up those soft thighs and lingered on the little bump jutting out from the green boy shorts. It wasn't too big, but certainly not too small. I could see the outline of her dick leaning toward her right and stopping just before reaching the waist of her panties. Oh for a just glimpse of that stiff head, I would've given anything at that moment. I was getting close and I knew I had to move on to the next photo lest my seed be spilt before the finale.

I click the arrow and my mouth drops. Not only because the shot was hotter than the rest, but because of her face. This one was larger than the others and the bars that were used to disguise the eyes were uniform for all the photos as far as I could tell. This being a larger photo, more of the face could be seen. Here came the revelation. While I still couldn't see the eyes, I saw enough of the face to recognize someone. This hot chick with a surprise so beautiful I was about to blow my load all over my key board was my little brother. As fucked up as it sounds, I kept rubbing my cock, and when the realization hit, I came harder than I had before.

Now you may be asking, what was so hot about the photo? Well that's the thing, this photo was no hotter than the second, but his face sent it over the edge. This was just kinky enough to send me into a full body contraction so strong that I can barely remember a time in which I had ever been this satisfied.

I sat for a moment, a bit of sweat building up above my brow, pondering what had just happened. I had just found out my brother likes to cross-dress, makes one hell of a hot woman, and I had jerked off and cum to his photos knowing damn well it was him. Further, I came immediately after realizing it was him. This was by far the furthest into a taboo territory I had gone to satisfy my own physical desires. I scanned the thumbnails of the photos for a few moments before I looked at the rest of the profile.

"Hot young CD looking for older man to treat me like the whore I am" the headline read. God damn, I thought. My brother wants to get fucked by an older man, and here I am jacking it to him. Oddly, where most would probably freak out and leave that website never to return again, I hung around and poured over the sparse sections of info on him. My only moment of hesitation came when I found my cursor hovering over the "Send a Message" button. What the fuck was I doing I thought. I can't just send a message to him telling him how hot he was and how he produced the best orgasm of my life knowing damn well the photo on my profile would accompany the message. Hell, just visiting his page would result in him getting a message that I looked at his page. How was I supposed to know it was him the whole time? All he would know is that I liked the Transgender/CD , or, at the very least, that I was curious. Reason triumphed, and I opted to leave well enough alone and get offline then.

That night I had a hard time going to sleep. I couldn't tell if it was just because I was shocked to find out that that hot chick was my brother, or if it was the fact that I came that hard. I eventually fell asleep, but images of my brother in that outfit plagued my dreams all night long. Needless to say, I didn't sleep well. The next day, groggy from a troubled night's sleep, and an early start, I staggered down the steps to see my mom as she hurried out the door. A quick "bye honey" and a closing door seemed to be all I registered that morning.

I wandered into the kitchen and mindlessly reached for some cereal and a bowl. Lazily shoveling cereal into my mouth images of my brother ran through my head. Christ, I thought, today is going to be as bad as last night. He hadn't gotten up yet, so at least I wouldn't have to face him. He had a closing shift, so I would have time to try and clear my head before I had to leave. That didn't work out very well however. Every silly, menial task that morning was on auto pilot as I would get hard following a flash of the pictures from his profile. After grabbing my belt and rushing around to find my keys I was off to work.

That day was a blur. Nothing meaningful happened at work. Middle management has that effect over time. I was just going through the motions really. I couldn't get my brother out of my mind. Then it struck me. Since he was working late, would he check his profile? Would he see that I was looking at his? Would he be intrigued? Would he send me a message? Sure these thoughts ran through my head the night before, but some sleep, a bit of food and a few cups of coffee seemed to make me consider the severity of the situation a bit more. This could get bad I thought, or really good. It's hard to say, but I did spend my last hour entertaining the thought that my brother would be as intrigued as I was.

After logging off my computer I practically raced to my car. I was dead set on checking my profile when I got home. As I pulled in the drive way, I noticed no one else was there. My brother was already gone, and mom either hadn't gotten home, or had gone out. Sure enough, when I got in the door, there was a note from mom saying she went out with some of the other ladies from work for drinks. Normally, the thought of losing out on a free homemade dinner was a bit of a downer, but not today. Today it was a lucky break. I ran up to my room and turned on my computer. I logged into the site and checked for messages. No messages unfortunately, but there were a few winks. I had never felt as anxious as I scrolled through the list. You see, when you send a wink to someone, you are letting them know you're interested. You get a little smiley of a face winking accompanied by the photo of the person sending it as well as a link to their profile. Most of them were natural women, older as usual, with two from the transgender/CD crowd. None were from my brother of course.

What was I thinking? Of course he wouldn't send me a wink. He knew damn well it was me by looking at my profile. There's no way he would express some interest in his own brother. With a bit of disappointment, I searched the profiles as though it was an obligation. There's a little tab at the top called "Recently Viewed". As I looked over profiles, more as a routine than with any kind interest, I would hold my cursor over the "Recently Viewed" tab considering whether or not I should leer at the hot chick my brother could turn himself into. Finally, the need for kink was simply too strong to deny. I clicked the tab and immediately scanned the drop down for his photo. There it was that black skirt, that green, knotted, shirt. It was him in all his feminine sensuality. Again, I scanned his photo, studying the last two rubbing my swelling member the entire time. After leering over the fourth of the bunch, I came again. Just as hard as the night before, my muscles contracted, and I shot a big stream. I swear if it was teaspoon it was a gallon. This time I spent more time considering sending a message or a wink. Of course, he hadn't done either to me, so why should I make things more difficult. I logged off the site, went downstairs and made myself a sandwich. The time rolled around to 9:30 and neither my mother nor my brother had gotten home yet. With nothing else to do, and an early morning the following day, I just walked up stairs and tried to get to sleep.

Again, dreams would plague my sleep. Every now and I then, I woke up during the night. I wasn't sure but I could've sworn someone was turning lights on and off. I assumed my brother had another late shift the following day so he was up. Eventually I got back to sleep. I was up around 7 and could hear my mother rustling around. I didn't have time to eat today I had a meeting to get to. Mom and I met at the door, both of us giving sleepy goodbyes as we stumbled out to our cars.

At the meeting my mind wandered as it often did at these things. These things are little more than pep rallies. They were more than a bunch of suits patting each other on the back for 2% increases here and there. So, I thought about my brother and started to get hard. Fuck it, I thought, I'm getting out of here. I excused myself, no one seemed to care, and set off to the bathroom. The whole way there images raced through my head. My dick was getting hard and difficult to hide in the light fabric of my suit pants. Luckily, most of employees were in the meeting, so there weren't too many chances to embarrass myself. I got into one of the stalls, slid my hard dick out of my pants and stroked myself imagining my brother in one of his outfits. I've never been all that imaginative, but, I came. I only had a few concrete images to work with, so my limited imagination didn't have much to work from. It was just enough though. I finished up, and sulked back to my dreary meeting. After that ended, I left for the day. There wasn't much to do anyway. Most of us, after meetings, left anyway, so it was no surprise to see a bunch of suits sauntering out of the building a couple hours early after a meeting.

Driving home I realized I would see my brother face to face for the first time since I discovered his profile. I wondered if he would say anything. He was a shy sort, or at least, I thought he was. Technically speaking, it was conceivable that I had no clue it was him in the photos, so he may not say anything at all. My mind was at ease for now, though the anxiety came back when pulled into the driveway and his car was still there. I tried not to show any anxiety, I'm a confident guy I thought. I could play this off.

I walked in the door, took a look around, and realized the coast was clear. This was silly. I was acting like a teenage with a crush. I shook my head and walked into the kitchen thrilled that a cold sandwich was probably all I had to look forward to. Sitting at the table however was my brother. Realizing that I was pretty much silent, I decided to break the tension.

"Hey, what's up man?"

"Nothing much. What are you doing here so early?" He asked.

"Oh, there was a meeting today. There wasn't much to do afterward, so I just came back here. It's one of the few joys of a salary job. Sucks though when you work overtime and you know you aren't getting paid for it. That's the trade off for days like this I guess."