Michael's Destiny Ch. 01

I peeked out at the blinds of my bedroom as my parent's car sped off into the morning light. Supposedly, they were going to some kind of camp for married couples looking to fix broken bonds out in the middle of Wyoming. Fucking Wyoming? I can't say I've really thought much about it until now... it is the least populous state. But soon my thoughts turned to what I was really happy about. For most teenage boys getting ready to leave for their freshman year of college, this would be a time for parties, girls, weed, underage drinking, and lots of sex, but as I looked at the large, 9-inch, flesh-colored dildo sitting on a pile of feminine clothes, I mused to myself how simply inaccurate those stereotypes would be for my week alone.

Removing the dildo from the suitcase it was tucked into and setting it on the desk next to my computer, I began to pull out all of my girls clothes one by one. Should I go cute? Sexy? I could never make the decision. After all, both looked good on me and both were far more comfortable to me than any of my boring old guys clothes. After standing there, surveying my options of panties, bras, skirts and shorts, and shirts, I finally decided to go with a bit of a blend of cute and sexy. Removing my clothes, my penis, barely 5 inches when rock solid, popped out of my boxers. I was semi-hard at maybe 3 inches, and I began to stroke it.

My hands felt so nice and soft... but I stopped myself deciding to save everything for once I was all dolled up. I chose a nice sexy pair of panties, blue satin Victoria's Secret ones, and my black, lacy, garter belt. Once those were on, I chose a cute pair of black thigh high stockings with little bows on them. Then, I slipped on a simple pleated skirt from my high school uniform, plain navy blue, and a white crop top (and white A cup bra underneath to simulate breasts) to show off my very flat stomach and very un-manly curves. Finally rounding things off with a navy school zipper hoodie, which I left unzipped, of course, I went off to do my makeup.

As I approached my desk to do my makeup in the webcam, I nearly grabbed my dildo and fucked myself right there. Lately, I had been getting better at making crossdressing more than just sexual for myself. However, I had decided that no such precautions would need to be taken this week as I was a free man, if man is a term that could be applied to me anymore, and I could be as horny or casual as I wanted. Tonight I wanted to be horny. However, I removed my smooth hand from the large latex cock, and forced myself to pay attention to the makeup. A little light foundation, blush, and eye liner. Then, I even set to using nail polish. As the nail polish dried, I decided to take a few pictures for my followers on tumblr. Taking the dildo with me for a few very seductive pictures (those always got the most reblogs and favorites) I went to my sister's room. There was nothing wrong with my room, despite it being a guys room, but my followers preferred the hot pink walls covered in the teenage memorabilia my college junior sister never took with her.

I took selfie after selfie, some without my favorite dildo, some with it in my hand, and even some with my licking it while staring seductively into the camera. That pose always drove my followers crazy. I decided my nail polish was dry and I could finally move on to more physical things, so I grabbed a bottle of lube I knew my sister kept in her bedside drawer and made the dildo slippery and wet. Taking a few pictures of me comparing my pitifully small cock next to the comparatively monstrous dildo (even now, I was only 4 inches) before I began, I looked and watched as my blog came alive with traffic. Smiling to myself as I applied lube to my ass I thought Wait till you see this...

Setting up my phone camera against the wall, and making sure the angle was right, I kneeled in front of the camera, and waved to anyone who might watch this later. I stroked the dildo and lifted my navy skirt to show off the bulge that the blue satin panties are garter were struggling to hold back. I could see that a little pre-cum was starting to get absorbed into the satin, and I smiled, knowing my followers would see that too. Finally removing my panties to show off my cock, which I stroked a few times, I moved the dildo behind me and, spreading my legs so viewers could get a good look, began to sit down on the massive latex cock. It hurt at first, and took a few tries to get it in, but once it slipped into my ass, it only took a few more insertions to get it balls deep inside.

I sat on it for awhile, stroking my cock, licking the pre-cum off the tip before going at it full steam, no touching my cock, simply going for an assgasm, and man was it fantastic when it arrived. Feeling the orgasm rise up made me feel weak as always, but as the dildo rubbed its realistic ridges against my prostate, I shot out a load like I had never shot before. It even reached my phone camera a few feet away, creating the perfect final shot. Ending the video and licking my cum from my phone, I wondered what I would do next. Sure, I could try another outfit, but I wouldn't be making another video for a bit after a cum shot like that. No, chance were that I was done with that for the day. At most, I'll be able to dribble out a little more in the evening for desert.

Returning to my room, I changed into some cotton hipster panties with hot pink polka dots and a long white t-shirt. I looked at my watch, it was barely 3pm. Damn! Well, maybe I could do another video. But what to do in the meantime? I was just descending the stairs to get some food when the doorbell rang. I froze, but calmed myself. Deciding to ignore what was probably the UPS guy, I sat on the couch and turned on the Tv to watch something funny. That was when I heard the lock slide out of place. Turning just in time to se what fate awaited me, I saw my sister and her newest boyfriend, and made the mistake of trying to bolt up the simple spiral staircase for my room.

"Who the hell is- Alex, get her!" While normally I would have been proud that my own sister didn't recognize me, I was more terrified of the star of the local college track team chasing me down. I didn't even make it half way to the second floor.

"Who the hell are- wait..." As he whipped me to face him, he saw the bulge in my panties. "Amy! Honey!"

"What?" she said, her voice rising in volume as she got closer. "Bring her down here, so I can see this little squatter piece of shit."

"That's just it hun," he dragged me all the way back down. "She is a he!" He raised my shirt, showing off the small, but noticeable, bulge in my panties.

Amy put her hand to her face. "God damn it Michael."

"Michael?" Alex said incredulously. "Isn't that your younger brother?" I simply hung my head in shame. "Hot damn. He's actually pretty cute."

"Don't get any ideas, Alex. What the hell are you doing, Michael? I thought we agreed it was best for you to wait until college before you pull any more stunts like this!"

"Well... I was but... Mom and Dad being gone and my followers-"

"Your followers?" she sighed. "You do realize your life revolves around more than how many people reblog your gay little dick, right?"

"Well yeah but..."

"Don't give me that! Why I outta-" I started to sniffle. I couldn't help it, I was scared as all hell. "Ok, stop that. You'll ruin your makeup. Alex, go lock up the house and I'll help Michael.

"Yes hun." He replied, as Amy guided me upstairs to her room. A part of me thought that this was the worst thing that could happen to me, ever. But then, another part reminded me that I might make the best of Amy and Alex's visit just yet.