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.