A Diamond in the Rough

"I see."

"So when do you work?

"I'm leaving soon actually."

And with that, he finished his soda and got ready to go. I was sitting eating my turkey sandwich when I noticed I was watching him when his back was turned. As he wandered the kitchen throwing away his empty can and putting a dish in the washer, my gaze followed. All I could think about were those photos. I saw him bend to through the can away and I became transfixed on his curved ass. I'd never noticed it before I saw his profile, but damn he had a great. Not large or anything like that, though it was shaped nicely. A smooth curve stood out from his otherwise slight body. He even had a slightly feminine heart shape to it when he bent down. Blood was rushing to my loins and I started to squirm. Then he bent to put a dish in the washer.

We had a rather large washer, lots of room for plates and cups. It was actually rather deep compared to others I'd seen. I think it was due to the washer being somewhat narrow, either way it resulted in my getting a show. As he bent down the waist of his pants dipped down just a bit. I noticed a lacy green band as he bent over. My heart started to race my cock jumped as I realized that the underwear he was wearing could very easily be the same boy shorts he wore on his profile. Good lord, I thought, did he wear women's panties all the time? The idea intrigued me and made me take pause for a moment. I was rock hard and he was getting ready to leave. I was a tad disappointed to have seen that knowing he was leaving, but, at least I knew I could jack off in peace when he left.

I finished my sandwich, he was out the door, and the house was mine for a couple hours. I ran upstairs and switched on my computer. I logged into the site and immediately looked up his profile. I was surprised to see however that I had a friend request. I was use to this. Normally they would be from single, older women looking for a younger guy. This however, was quite different. It was from my brother. Holy shit, I thought, he made no mention of anything when we talked, acted as though he hadn't even known I had seen his profile, and he's now sending me friend requests. The request didn't come alone however, there was a message. "There are more pics for friends ;)" it read.

I was shocked, turned on, and more importantly, curious. My heart raced as I hit the "accept" button. I couldn't believe it, my brother wanted to be "friends" on a website designed to hook up singles. This was amazing. Not only that, he wanted me to see the other photos, the ones only friends could see. These by the way, were normally much hotter, more explicit, and just generally more fun to look at then the others photos people post. After accepting his friend request I was prompted to check his page again, which I did without a thought. What I saw was amazing.

Apart from the original four photos I saw, there 8 other photos. In these, he was not trying to hide his identity at all. I suppose, because you had to be friends, he didn't mind his face being shown. In these he had full makeup on as well as a hot little plaid dress with a white button up shirt, the classic school girl look. The skirt, like the black one, barely covered his shapely ass, and the shirt, knotted like the other showed his bare mid-drift which was tan and lean. Fuck he made a hot girl.

The first photo had my brother in a pose in which he was standing, clearly showing his high heel shoes. His legs, while slim and soft, were just toned enough to emphasize his tight thighs. Pressing together, his legs were on full display. I could imagine how smooth they must feel. God, how I wanted to slide my hands up and down his smooth, firm thighs. My gaze wandered up his tight little body past his lean abdomen, up his small, pert tits, along his slender neck and up to his pretty face. He made quite a cute girl. He wore blood red lipstick making his mouth the center of attention of his beautiful face. His lower lip pinched between his teeth, he teased all his friends with this look, me included. I wanted him bad.

The second photo was the second part of a series apparently. Here he seemed to crawl toward the camera. His thin arms holding up his light frame easily. He continued to nibble on his crimson lip as his head fell slightly to his left. You could see right down his shirt. There wasn't much to see, but the small crease of cleavage excited me to no end. His white skin created a perfect little crease in the middle of his chest. I was getting harder by the minute. Just beyond his right shoulder his shapely butt jutted up just enough to be seen. He clearly planned these shots out. My brother was such a tease. All that could be seen was the plaid of his skirt, but, the two soft bumps separated by a little dip left me wanting far more.

After pouring over the image, I moved on to the third installment. Here he was rising up on his knees. Again, his crimson lips pinched between his teeth. His small hands had freed the knot now and were working on releasing the first button. The anticipation I was experiencing was incredible. How far would he go?

I moved on to the fourth, and my brother had now revealed a small hot pink bra as his shirt began to fall from his small frame. Resting just below his shoulders, his shirt was on a one way course to a heap around his legs. His head dropped in this image. I could just barely see his eyes, full of desire. What he was working up to, I had no idea, but god I wanted to continue.

In the fifth shot, he had turned now. Only a few small pink bands covered his back. He looked back into the camera for approval it seemed as his hands reached behind him. In his right the little zipper of his skirt was held tight as it was slowly dragged downward. His left hand rested peacefully on his hip. The zipper's fall stopped in the middle of his luscious ass. Pink boy shorts covered his curves and I licked my lips wondering what more was in store for me.

Hard and wanting to burst, I moved forward to the sixth image. Here he dropped forward, again letting his slight arms hold up his frame as he arch his back and made his ass the center of attention. A gorgeous heart shaped bottom covered only in his hot little boy shorts. If I only I could dive into the screen and give him a playful squeeze I thought.

I moved on quickly to the seventh shot, this one further along in a sequence it seemed. Wearing his bra and boy shorts he was sitting back on his ankles. His playful smile teasing me as I looked to his hand resting on the floor, realizing he was holding something. There wasn't enough of it in the shot to figure out entirely what it was. I skipped to the next shot to see if it was meaningful at all. Sure enough, it made my day.

In the final shot, my little brother, the one I had tried to protect in younger years, the one I tried to help get a date with a girl, was on his knees, crouching forward toward the camera, with a large dildo in his mouth. The look on his face was pure love for the act. Eyes closed, head turned just slightly to the right, with half a dildo hidden by his red lips. I would stay on this photo for minutes stroking my now rock hard cock. I tried to keep it going as long as possible, but, nature can only be held back for so long. Soon, ribbons of cum sprayed my stomach and legs. God, I thought, that was incredible. Hotter still, my brother wanted me to cum for him. He wanted this as much as I did. Today there was no doubt, I was, at the very least sending a wink. Which I did, soon after wiping away my warm cream, a message was sent to my brother letting him know he had an admirer.

The rest of the night was a blur as I could only think about the pictures I'd seen earlier. Would any more come of this or would it simply be a bit of teasing that would just end with me cumming to brother every now and then? I chatted with mom over dinner at some point, but I couldn't tell you what we talked about. Hell, I'm not even sure I said anything. All I could think about was a dildo being half buried in my brother's mouth, and how I desperately wanted that to be my dick instead.

He was working late again and wouldn't be home for at least another hour. I ended up chit chatting with mom about who knows what, and eventually went to my room. I had no intentions of going to sleep though. All I was interested in was releasing some pressure from my balls. A few times that night I fumbled around with my hard dick allowing myself to get close to orgasm, than holding back, trying to build up one big shot for my brother. Though, again, you can hold nature back for so long before it simply takes over. I blew a hefty load on my stomach and drifted off to sleep. When I woke, I realized, it was Saturday. No work for me. No need to wake up early, I could just lie around and do nothing.

It seems that in my fevered rush to jack off, I had completely forgotten I was off and was left with nothing to do. Then it came to me that unless he's working, I have to face him today. There was no getting around it. Sure, he friended me, and sure he didn't seem to mind what I was looking at. Hell, he probably liked that I was looking at it. Still though, there was a bit of anxiety mixed in still, so this would be tricky. Luckily for me, when I went downstairs he had left for work just a little before I got there. According to mom, he was working a mid-day shift, and wouldn't be back until that evening. The anxiety was gone for now.

I ate with mom, had a bit of mindless chit chat, and she informed me she would be going out with my aunts for the day, so my brother and I would have to fend for ourselves for dinner that night. I was fine with it despite a bit of anxiety creeping back into my mind. I went to take a shower as she was preparing to leave.

I stood there with warm water cascading down my frame as thoughts of what could occur that night raced through my head. Would we actually do anything? Would this be more than just playful internet teasing? I didn't know, but the thoughts were getting to me. Soon I felt that tell tale jump in my crotch. Blood was racing for the head and was not going to try and stop it. I slid my hand up and down my shaft, feeling it get stronger and harder with each stroke. Visions of my brothers soft lips engulfing my manhood made me moan. Soon my slow stroke became a fast session beating off. I wanted to fuck, and I wanted it right then and there. I even forced my hips back and forth imagining myself behind my brother burying my hard cock into heart shaped rear end I had studied.

With a strong shake, my body convulsed, and I released my seed into the drain with the water washing over me. It was incredible. I had to do something at this point. I didn't care about what may or may not happen now. I wanted something more than just jerk off material. I finished my shower, turned off the water and towel in a matter of seconds it seemed. I wandered into my room and switched on my computer from its sleep. I logged into the site intending to send my brother a message, I wasn't sure what the hell I was going to say, but I was going to say something. Before I could, I was brought to a dead stop. There was a message with an attachment. Now, this was interesting. I rarely got any kind of attachment with a message, just general info and occasionally some invitation for cyber sex.

This one was different. This was from my brother. The image was brief. It read, "I thought you'd like the pics :). Thanks for wink big brother." Well he obviously got my wink, and already visited the site that morning. Just below the message field I saw the attachment. "For_You.mov" it said. Holy shit! He made a movie, and apparently it was a movie just for me. My brain crashed at that point for a moment. I had to shake it back to life to get myself to click the attachment. I fidgeted as I watched the download bar travel from left to right. "Download Complete" was the message, and I double clicked the file immediately. My mind raced wondering what it could be. The first shot came up. It was my brother, smiling wearing his girly clothes, mouth slightly open as though he was about to speak.

The movie buffered completely and hit play. Sitting in front of his laptop, he looked so hot. The anticipation was killing me. My cock pulsed as I imagined what would happen. At first there was nothing but dialogue.

In his best feminine voice he said, "Hi big brother" with a smile splitting his beautiful face. "I'm glad you liked the pics. I knew you would love them. After I got your wink, I knew you would want something more. So here I am." With that he giggled the way a young girl does the first time she has sex. Anxiety, anticipation, desire, and willingness to submit to those desires all translated in those few short sentences. "I hope you like it" the dialogue ended.

Soon, his hands dropped below his desk, he paused for a moment looking at the camera biting his lip. His hand rose and held tightly within in it was the large dildo from the photos. He set its base on the desk in front of him. His eyes darted from the camera to the cock and back again several times, as though he was asking me if he wanted me to watch him. It was as though he anticipated my thoughts. With a sultry voice he asked, "Want to watch me suck this big brother?" "Want me to suck you?" he said with the sexiest smile I'd ever seen. He giggled, closed his eyes, and descended upon the rubber dong in front of him. He opened his mouth and slid slowly down the shaft. He stopped halfway, turned his head side to side, sucking lightly on it. He raised his head. "Are you stroking yet?" he said. He smiled again, and then lowered his head. His tongue glided down the shaft and his head rose as he made his way back up. His eyes opened on the second pass. He was quite a tease, and I loved it. Up and down he went, looking into the camera, and then as he rose for the final time, he opened his mouth and came down deep on the shaft. He dropped down slowly engulfing the cock falling as far to the base as he could handle.

My cock was engorged and about to burst. I stroked endlessly studying every movement he made. I wish my hand was his mouth, and if I got the opportunity, I was going to make that happen.

His rise and fall became faster, and he would turn his head slowly as he fell upon the length of the dildo. Soon he rose up one last time and looked at the camera. "I hope you liked that, but I hope you haven't cum yet, because I'm not through." With that he stood, revealing nothing by a pair of boy shorts barely covering his erection. His face was now out of the shot, all I could see was his right hand wandering down his tummy, getting closer and closer to his member. Outlined beautifully, it was incredible. His hand drifted over it, sliding up and down its length. His voice came again "do you like this? You like to see me play big brother?" Hell yeah I did. I was getting closer and closer to cumming. "You want more baby?" he asked. Soon he turned around bent down at the waist putting his plump little ass in my view. He slowly swayed from side to side, my eyes followed each movement. What would he do next I thought.

That's when he stood back up, and his slim hands fell to his waistband. He ever so slowly slid one side down, and then followed by the other. The tiny, incremental movements of his waistband transfixed my eyes. I was no longer stroking. This was my first time seeing his ass. All I wanted was to see was his tight little hole. He finally slid both hands down dropping the waistband of his panties just under his round buttocks. It was a gorgeous site. Plump, though narrow, it was wonderful. I couldn't see his face, but I could hear the teasing nature of his demeanor when he said, "You want more big brother?"

He leaned forward as he had before allowing me to get a good look at exactly what it would be like to be behind that naked ass. I could see his tight balls just below his plump little ass and it excited me even more. I began to stroke again as he slowly parted his legs. He arched his back and moved his hand to his ass. He smacked it twice, and the sound of flesh hitting flesh made me gasp. His hand wandered to his sweet crack and he spread his thin fingers to show me the object of my curiosity. His tight little hole was on complete display and I wanted nothing more than to bury my face in his ass and let my tongue explore him. As these thoughts flooded my mind, he brought his hand to his face to lick his fingers. Soon his hand was back at his ass, his moist fingers swirling around his asshole. I saw him gently press his fingers in as he swirled them around, and then I heard him say something so hot, I could no long control my orgasm.

As his fingers finally began to slide into his hole, he whispered just loudly enough to heard, "I wish these were your cock." And with that he moaned as I came. The stream seemed endless. It couldn't have taken more than a moment, but it seemed an eternity. It was as though I just released year's worth of repression. In reality, it was only a few hours' worth of no release. It was amazing however. I sat there, with cum trickling down my hands, some lying across my thigh, watching him. The movie only lasted a couple more minutes but it was great. His fingers slid deep into his ass as he jerked his cock with his other hand. His ass clenched as he finally came. He stood, turned, and showed his cum covered hand to the camera. "That's for you" he said. Then the video stopped.