7 comments/ 28520 views/ 19 favorites Michael's Destiny Ch. 01 By: CrossdressingDestiny 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. Michael's Destiny Ch. 02 By the time Ashley and I were upstairs, my sniffling had stopped, though I was no less distressed. Ashley obviously already knew... hell she was the one who saved my ass from my homophobic parents when they almost caught me last time. But still... Destiny is a private side of me! Only I know her- really know her anyway- my followers just see a cute sissy boy slut, but Destiny is more than that. She's my alter ego! I was snapped out of my revelry when we reached my sisters room and she sat me down on her bed, while she stood facing me. "I can't blame you, Michael." "Blame... me?" "For all this. I would be such a hypocrite if I criticized you for wanting to be sexy and showing off. I'm only a junior in college, and I've already seen and enjoyed more dick than I could count on all of my, your, and Alex's fingers and toes." Damn, that's a lot of dick. "So... I guess what I'm trying to say is sorry, Michael. For reacting the way I did. It's just seeing you like this... brought back some bad memories." "Yeah." We paused in awkward silence. I could hear the breeze flying through the room, and felt it easily slip its cold whispers through my panties and onto my cock. I glanced around the room, looking for something, anything to say until Ashley moved over to me and flopped over on the bed. "So uh... I never asked you when I found out. You have a name?" "Yeah. Michael. I'm your brother?" "No no no." She rolled over, and put her arms under her D-cup breasts and her feet in the air. "The person in front of me can't be my brother, she's too feminine. My video game loving, mostly straight acting, brother is nothing like that!" She winked. "So. Do you have a name?" I turned around, and sat crossed legged on the bed, facing Ashley. I guess that wind had cause my dick to shrink even more, because even with my legs stretched apart like this you could barely notice my bulge. Moment of truth... "Destiny." "Destiny huh? I had a friend named Destiny... But that's not important." Ashley pulled out her iPhone to check the time. "Wow! It's not even 4pm! I'll tell you what, Destiny, why don't you and I do a little one on one fashion show while Alex makes dinner?" "R-really? You wanna do that?" "Of course! I've gotta see the kind of clothes you like, and see what my competition will be like once we're both off to college again!" She giggled this mildly obnoxious and very feminine giggle. I decided I kind of liked it, but even with my voice already a high tenor or alto I wasn't going to try it. Yet. "Well... ok," I sighed. "Perfect! I assume all your clothes are hidden somewhere in your room, and not in mine?" I nodded. "Hey Alex honey?" "Yeah?" He responded from across the house. "Bring my suitcase up to Michael's room! Whoever this cutie is has a few things to shoe me!" I blushed in embarrassment. In an act that took seconds for Alex the super athletic track star but would have taken me days, Ashley's bursting-at-the-seams suitcase was finally upstairs. She opened up her suitcase and began rifling through things, while I reached into a few drawers hidden carefully under my bed and did the same. "Hm... Destiny, you got anything kind of day to day? Like... what would you wear to go shopping or around campus?" I panicked again. I had never been dressed up outside of my room. Sure, having lots of followers and making a few bucks here and there with cam shows was one thing, but I always wear lots of makeup and try to keep the camera out of my face for a reason! Ashley noticed I was distressed again, and leaned in to whisper to me. "Listen, Michael, Destiny, whichever you prefer. I get it, this isn't easy. But I'm here for you, so please, don't be afraid to push your boundaries!" I swallowed hard. "Ok sis... Well I do have one pair of skinny jeans that fit, and a plain white t-shirt and nude bra to go with it. I bought it on a whim, but my followers weren't huge fans of it." "Fuck your followers. Today is all about you! Show me!" As she said this, she stripped off her shirt, letting her D-cups bounce. If only I wasn't gay. And her brother... And then, she even unstrapped her bra, and dropped her yoga pants and panties in one fell swoop. I was stunned. "What?" she asked, as I stared. "Sorry... I've never seen a girl naked before, in real life anyway." She smiled innocently, and bent over to access something from her suitcase. She came back with a few things, and began to step into a black g-string thong made of nylon, a pair of tight fitting hotpants, and a white crop top, no bra. "Well, let's see what you've got girlfriend!" I took a deep breath, and dropped my panties, letting my tiny, shriveled cock unfurl from its mostly tucked position. "It's ok, Destiny! Every girl's got her assets, and dick just isn't yours! Though your legs are stunning and," she paused looking down at her large breasts, "I hear flat chests are "in" again." I nodded nervously, and took off the plain white t-shirt I had been wearing and strapped together an A-cup nude bra, and put on a slightly nicer shirt that had R2-D2 on the front. Then, I picked up a simple pair of white, cotton briefs, and stepped into them and the skinny jeans. I looked up at the two people in the mirror, mildly surprised. Ashley has always been taller, even without heels, at 5'10" and me at 5'5". But here in front of my floor length mirror, the difference was stark! All of her clothes were much sluttier than mine, but somehow the revealing nature of her's couldn't compare to the innocence of mine. I had no bulge to speak of, thanks to how tightly the jeans held my crotch, and my chest was one of a sexy, yet reserved young girl. "Wow..." I said. "Wow indeed Sis!" Ashley replied. We looked each other up and down. "Ok... you ready for the next outfit?" "Yeah!" All my nervousness was gone. "What is it?" "I wanna see your sexiest night wear! Mostly because you had me on this outfit, and I need a gimme round!" "Oh, you're on Ash!" I think by the time dinner was burnt and pizza ordered and arrived, I think Ashley and I had gone through almost everything I own, and barely made a dent in her collection. I got to see her in everything from her sexiest victoria's secret nightie, to her own collection for schoolgirl stuff for when she and Alex roleplay, a few fancy evening dresses, and so on. We also got to really test our makeup skills, sitting around doing each other's makeup for most every different outfit. The whole time, we were giggling like girls so hard that we even ignored the smoke detector beep when Alex burnt the fish he was trying to pan fry. "Ok, Alex just texted me that the pizza is here... he never could cook anyway. But I want to see one last outfit. Bikini time? I figure after dinner we could even hop out to the pool in our backyard and-" "I don't own one." "You don't own a bikini?" "Or any swimsuit. I didn't have the balls to grab one when I went shopping before." She stared at me, shocked. "And yet you own no less than 3 garter belts with matching panties, stockings, and nighties?" "W-well..." "It's ok. Tomorrow, you and I are going to go shopping together, with you all dressed up so you can actually try on things in the store and stop hoping that it's the right size." "Wait wait wait. No way! I'll get recognized!" "Oh please, I didn't recognize you at first, and I knew your secret! Plus, I'll make Alex punch anyone who tries to mess with you. His arms don't look nearly as strong as they are." Suddenly, I was thinking of what being dressed in public would be like. What if I accidentally used my male voice! What if I got an erection? Oh god... I'm getting an erection right now! Please please please don't see it Ash! But of course, sitting there in my see-through white nightie, my raging, 5 inch erection was on full display as a bit of precum stained the white satin panties that said bride on the front. Ashley just shook her head and smiled. "My my. An entire afternoon spent as a girl with your hot sister, and going out in public is what puts little Richard at full attention? It's ok." "You're not bothered?" She didn't respond with words, she just gave me a look that said "Really? I did tell you how many dicks I've sucked, right?". She turned around and rifled through her suitcase some more, finally pulling out a massive 11 inch, hot pink vibrator and a canister of lube. "I'll leave you two alone while I make sure Alex doesn't eat all the pizza. Come on down when you're done, but take your time. I couldn't help but notice that you don't own a vibrator or anything longer than 9 inches... be careful but take as long as you need. See you downstairs sis!" She stood up, and her breasts bounced again, pushing against her red and black baby doll, and then closed the door behind her. Then, that wind from before returned, only this time it was warm, like natures hand job. But wind alone couldn't get me off, so I lowered my panties and got on my knees to lube up. As I reached my hand back to stick a few fingers in first, it almost seemed like my ass was sucking in whatever I put back there. With little to no effort, I got all five fingers inside, and that was without lube. So, once lube was applied to my asshole and the vibrator, I turned it on a low setting, and began to sit down on it. It felt heavenly! I didn't even want to take it out of my ass at first, I just wanted to sit on it all day while my erection raged on so hard that they popped out of one of the leg holes of the panties. Eventually, I got an up and down motion going, even did a few pull it all the way out and then push it in all the way to the hilt. After a while of just loving the feeling, I looked down at my watch. 6:30pm. I've been fucking myself for 30 minutes? I never go that long! I finally decided it was time, and so I turned the vibrator up to full power and started ramming it in and out of my tight ass while I sat on my knees and one elbow. It didn't take long, but when I came I actually came so hard that my jizz, which only few hours prior I had been sure was mostly dried up for the day, shot across the wood floor of my bedroom like a horse in the Kentucky derby! After a few more pitiful spurts, each growing smaller but no less amazing feeling as I slowed the pace of the vibrator, I removed the vibrator from my ass and set it on my nightstand, just letting a few more dribbles of cum escape my cock and drip onto my white stockings. Normally I'd have freaked out about the mess, but with no parents around and my sister and her hot boyfriend to protect me I wasn't worried. I used my fingers to clean up most of the cum, but didn't take the time to really savor it like I normally would. Finally, I decided to change back into the day-to-day look from before so that I at least looked like I hadn't just fucked myself for 30 consecutive minutes. Once I was re-dressed, I went downstairs and grabbed a slice of sausage pizza, musing to myself how it was kinda funny that they ordered sausage pizza after everything that had just happened. "Hey sis! Have fun up there?" Ashley said, not quite stopping herself from laughing at her own comment. "Uh, yeah. Yeah it felt pretty good." "Told you." Finally, Alex spoke up. "Ok, so I get the brother/sister, sister/sister thing but can we like, watch a movie or some shit? I'm tired of being such a third wheel." "That's not gonna change with a movie," Ashley said. "Yeah, but make it scary and I can at least pretend." "Oh, you're so brave, Alex." Well, now I'm the third wheel. After we got done watching one of the Saw films, it was time to hit the hay. "Sleep well Destiny. We're gonna go on a shopping spree tomorrow!" I smiled, and nodded sleepily. Even though it was barely 9, I was dog tired. Probably has something to do with that vibrator... I stripped down to my panties, and took of my bra, but left the shirt on and decided this would serve as pajamas well enough. In the next room, I could hear Alex's muffled moans as Ashley sucked him off, and later her muffled moans as his undoubtedly large cock entered and exited her vagina over and over again. I found myself hoping that I would find a boyfriend at college so I could do exactly what Ashley was doing right now, but I fell asleep before I could think about it too much.