A Secret Shared

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Sharing secrets leads two friends to exploring each other.
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~The following is just a fantasy of mine. Any name or likeness to any persons or events is coincidental and unintentional. This is a one-shot to get rid of my writer's block! If you like it, I may continue on further!~

*****

Two years ago:

Troy's Perspective:

I woke with a start. I had that same weird dream again. I kept dreaming of this blonde girl I had never seen before. I couldn't get her face out of my head. The weird part is, I couldn't even make her face out. I didn't know what she looked like, but I still couldn't get her out of my head. She was stunningly beautiful as far as I could tell. She was kind of tall, yet shorter than me. 5'9 maybe. Her long, blonde curls laid perfectly on her shoulders, and some traveled down to her back.

The only thing I wanted to do to her, was love her. I wanted to be in love with her. I wanted to make love to her. And so I did. I dreamt of fucking this goddess of a woman every night. I would sit down on the edge of the bed as she would slowly slink down onto her knees and kiss the head of my cock. She'd wrap her red lips around it and take all of it in her mouth, bobbing her head up and down. She loved the taste of it. She'd lay down on her back as I penetrated her ass. She had a cock, but I didn't care, nor pay any mind to it. She'd wrap her long, silky-smooth legs around my back and throw her arms around my neck. I'd kiss her tenderly and passionately as I continued pushing my cock in and out of her tight little ass. She'd break the kiss only to make soft moans and other lovely little sounds. We'd keep this up until she'd use her legs to roll me over, and I'd grab her hips. She loved to be bounced on my cock and she'd giggle and moan as I thrusted up into her.

But alas, a dream was a dream. I knew I'd probably never meet this girl, let alone get to do any of those things with her. I had to go relieve my morning wood, as I was supposed to hang out with my new friend Ray in a few hours. Little did I know, he would become a huge part of my life.

Present day:

I continued having this same dream over and over for two years. Ray and I were now best friends, and we were about to finish our sophomore year of college. Today, we were supposed to hang out, drink and do some regular college guy stuff. But instead, I'd share my secret with him. I was going to end up telling him my dream girl is a transsexual.

Ray's Perspective:

Today was the day. My best friend of two years, Troy, was coming over to my house. He wanted what he used to call "guy time" with me. I had been hiding something from him though. I was not a guy. Not entirely. I spent most of the time that I wasn't with Troy dressed "en femme". Today was the day I would tell him all about my secret. I didn't know why, but I wanted him to know. Something about him caught my interest two years ago.

I also had this secret fantasy. I would fully dress up in my favorite outfits or sexy lingerie. I had acquired quite the collection over the years. Some had been "borrowed" from my older sister. Some had been "borrowed" from my mother as well. All the women, and the one man who wanted to be a woman, in my family were around the same build. As cliche as it sounds, I ended up being a small, slender guy. I only stood about 5'9. I only weighed about 135 pounds soaking wet. Having naturally wide hips, a round bottom, and this naturally slight build I would often be mistaken for a girl anyway. Maybe that's why I wanted to be one so badly.

The only thing manly about me, was I kept my hair relatively short. No longer than my chin. I grew it out once, and my sister's drunk boyfriend mistook me for her and tried to, um, force himself on me. I tried to appear as manly as possible while not en femme after that. I had to keep up the illusion. Baggy clothes, boxers, the like. No one had to know I was completely shaven and smooth underneath.

My sister's boyfriend wanting to fuck me so badly did start putting this fantasy in my head. I wanted to know what it was like to actually let a guy fuck me. I wanted to try to sucking a cock. So, I tried. My sister kept a lifelike dildo in her closet, and it stayed there after she moved in with the aforementioned boyfriend. I had gotten so lucky! I took it, along with some cute pairs of heels and flats, from the box in the bottom of her closet and hid it in my own. After meeting Troy, I even began to wonder what it might be like if he fucked me...

DING-DONG!

The doorbell rang. Troy was here. I took a deep breath and put on my best "man-face" and headed downstairs to let him in.

"Hey, Ray! How's it going, man?"

"Great, I guess. You look happy. What happened, you get laid?" I hoped not. Part of me wanted him. Badly.

"Nah. Been dry for two years." The random conversation continued as we went through the motions. We watched some TV, played some video games, and drank a couple beers. After the second beer, Troy said something that would change our lives and our friendship forever.

Troy's Perspective:

"Hey, Ray. I need to tell you something. Something I've never told anyone." I started there. I didn't know where to begin. It's hard to tell another guy you have dreams about a transsexual every night, but I had to get it out.

"Oh? Really? What's that? You can tell me, dude. I mean, if we're sharing secrets and all..." He zoned out for a second. Wait. Did he have a secret too?

"Hm? Do you have a secret too? Who should go first?"

"Maybe you should. My secret is a little... different."

"Different? How? Well okay then. Here goes..." I told him. I told him about my entire dream, start to finish. I spared no detail. His face at first made this really astonished look, but the more I talked about the things I do to my dream lover, the more at ease Ray became. In fact he even seemed to be smiling.

"Don't laugh at me, okay? I'm pouring my guts out here, man."

"I'm not laughing at you, silly." Did his voice just go up an octave? "But, I guess it should really be okay for me to tell you my secret now. Well, just wait here. It will be easier for me to show you."

Show me what? I sat there confused at his sudden change in demeanor and mannerisms as he ran up the stairs. I didn't know what else to do so I sat there for what felt like the longest hour of my life. But then, it was my turn to be astonished. He- no, she came back downstairs. In the hour he was gone, Ray had transformed himself into a pretty young blonde. She wore a black dress that buttoned in the front, exposing a little bit of cleavage and her long, silky-smooth legs. She matched the dress with a pair of strappy black stiletto heels. She had to have been wearing a wig because her short, mousy blond hair and been replaced with flowing, golden locks. The light from the window in the stairwell shone brightly off of those flowing, golden curls like a halo. They were the same flowing, golden curls I saw in my dreams. Ray was my dream girl. All along, she had been right here beside me.

Rachael's Perspective:

"Sorry to keep you waiting," I said as cutely as I could, "It takes a little bit of time to get dressed. This is my secret, Troy. I may not have had any procedures done yet, but I'm a transsexual."

"Ray-"

"Rachael. It's Rachael when I'm all dolled up like this." My heels clacked on the floor as I walked over to the couch where he sat in shock. I sat down beside him, positioning myself where he had a full view of my cleavage, and my legs. I saw his eyes trace my every movement, and how they wondered across my body, taking in the view. Troy was the first person to ever see me. The real me.

"Okay. Rachael it is. That's a very pretty name, for a very pretty girl." I started to melt. I dressed in my favorite outfit, hoping to come out here with some confidence and maybe, just maybe begin to get what I wanted more than anything. But, I wasn't in control here. I looked longingly into his eyes as I scooted a little closer to him. He stared back, and as if reading my mind, he threw his arm around me. Then, it started.

I leaned up towards him, as he leaned down towards me and our lips met. An electric current traveled down my whole body as he embraced me. I let myself go, surrendering any traces of masculinity I had left. I was in the arms of a man now. A man who wanted me as much as I wanted him. I felt the man Ray had been die. All that was left in his place was Rachael. And Rachael knew what she wanted and how to do it. I broke off from the kiss long enough to whisper "Let's take this upstairs." I grabbed my lover's hand and led him up to my bedroom.

As soon as we were in my room, the door closed behind us, and we returned to making out. I let his tongue make it's way into my mouth. I let him explore and then began returning the kiss. We stood there making out like teenagers. I jumped up, and without missing a beat, Troy grabbed me and wrapped my legs around his back. He carried me over to my bed, and laid me down on my back. I sat up and began pulling his shirt over his head. I threw it on the floor and kicked off my heels. He began un-buttoning my dress and I felt it slide off. I slid off the bed in nothing but my matching white bra and panties that I had stuffed with homemade breast forms and pulled tightly to create cleavage.

I got down on my knees while he sat on the edge of the bed. "I'll try my best to make your dreams come true, Troy." I un-zipped his fly and slid his pants off. After tossing them aside, he took his boxers off. I was finally face to face with my first real cock. I had practiced what I was about to do on my dildo several times, but now, I got to taste the real deal. I kissed the head of his now erect cock. I opened my red lips and let him slide it into my waiting mouth. I controlled my gag reflex and began taking his full 7 inches into my waiting mouth. I began bobbing my head up and down, working my tongue around him. He kept moaning in pleasure as I'm sure he was saying things like "Oh, fuck", "that's so good", and "better than I dreamt".

I kept going for almost 20 minutes until he stopped me. He grabbed my shoulders and guided me up to my feet. "If you don't want to do this, you don't have to," He started. "What we're about to do, it could change you. Sucking a guy off is one thing, but I want to penetrate you. You may never be the same again. I want to fuck you, Rachael, but you have to tell me you want it."

"I want it." I responded, opening my drawer to reveal a condom and a tube of AstroGlide. A girl has to be prepared! I sat down on the bed as I opened the condom and slid it onto his throbbing cock. I coated it with AstroGlide before applying some to my own, waiting hole. I laid down on my back, and opened my legs. I signaled him to come in for the landing, which he did. He crawled on top of me, and for the first time in my life, I felt a cock poke the entrance to my ass. He slowly slid his member further into me. At first, I whimpered in a little bit of pain. He slowed down and tried to stop, but I shook my head no and told him "Please, Troy. I want this. I want you. Please, fuck me." With that, he needed no further encouragement. He pushed his cock all the way in to my ass. I cried out in a mix of pain and pleasure.

The pain began to subside as he backed out and pushed in again. I began to match his thrusts and we got into the perfect rhythm. I wrapped my legs around his back and threw my arms around the back of his neck. I leaned up to meet his passionate kiss as he continued plowing in and out of my ass. All traces of pain were gone. This was sheer pleasure. And the greatest pleasure I've ever felt! He picked up the pace, getting faster and faster with each thrust. I broke the kiss off momentarily to let out the most feminine moans and sounds I have ever made escape my cherry red lips. Ray was officially gone forever. Rachael was getting fucked, losing her virginity to her best friend. I loved cock! It was far better than I could ever imagine.

It was now time to keep his dream going. I wanted his whole dream to come true, as he was making mine. I tightened my legs around him and tried to roll him over. He was stronger than me, and still pushing in and out of my ass, but he got the idea and rolled us over. I re-positioned myself to get comfortable. He grabbed my hips and lifted me up, almost all the way off of his cock, and I slammed myself back down onto his groin. I giggled and kept moaning, enjoying riding a cock for the first time ever. I bounced up and down on his cock for what felt like forever, and I wished it was forever. I loved it more than anything in the world, except maybe him. I was so into it that I didn't even notice the door crack open. Neither of us did. Troy rolled me back over onto my back and pushed all the way inside of me. I felt something change inside me as my whole body shook with pleasure and I came. I came all over my stomach. The condom must've broken, because I felt jet after jet of warm, sticky semen fill my ass. Troy slowly pulled out of my ass with a plop and rolled over on his back laying next to me. I snuggled up next to him, my head laying on his chest.

FLASH!

My sister was standing over us, camera in hand. She had been watching us through the door! I had no idea how to react, until she started laughing.

"Haha. I knew something was going on with you, Ray-Ray, but this? This is fantastic!! I've always wanted a little sister! Looks like I got one!"

"Renee!? I didn't know you were coming over." My sister just caught me. her little brother, in makeup, wig, and a bra with my best friend's cock in my ass and that was the best I could think of? "I mean, this... This is..."

"Oh save it, girl. I saw everything. You are so at home with a cock inside you. I've never seen anything like that. This guy, he makes you feel complete, doesn't he? You look at him the same way I look at Mike. You really are my sister. Get dressed and come talk to me. Oh, sorry kid. I'm stealing your girlfriend for a minute." She added, looking at Troy. He was as dumbstruck as I was, but I got up and put on a pair of panties. I also threw my dress back on and buttoned it up as I walked to my sister's room, cum still leaking from my ass.

"Why did you take a picture?" I asked.

"Insurance! I want to make sure you're not going to back out of this."

"Back out of what?"

"Being a girl, of course! With Mom and Dad gone, it's just you and me. I'll help you as much as you need. Anything I left in this room is now yours. You'll need a new wardrobe, because we're burning all those nasty old boy clothes."

"Renee- I..."

"Rachael, please. Yeah I heard him say your name, amongst other things, while you were in there getting plowed. From now on, You are Rachael Johnson, my sister. I already texted Mike, and he's cool with you being yourself. He feels better about trying to fuck you last year now."

"You knew about that!?"

"Of course, hun. He told me. I was mad at first, but then it made sense. Look at you. You're almost cuter than me! But we'll talk more later. Take this nightgown and these panties. Go dry yourself off. And get rid of that white bra. You ain't no virgin anymore, sis."

I dried myself up and got changed into the short black and red nightgown and the matching red bra and panties Renee gave me. I fixed my wig and looked in the mirror at the girl staring back at me. It all began to sink in that I had just been changed forever. I was a girl now. I was Troy's girl now. "Okay." I said, "I'll do this. I've never been happier than when Troy was making love to me, being in love with me. Loving me. After all, I want to be a girl. His dream girl."

She smiled. "Then go back to him, girl. Stay with him for as long as you can. You may have wanted to be a girl, but that boy just made you into a woman." I did what my sister said. Troy was already asleep when I got back, so I slid into my bed next to him. I snuggled up close to him, wrapping my leg around his and laying my head on his chest. He snuggled closer and wrapped his arms around me. In this moment, I knew one thing, and one thing only.

I was exactly where I wanted to be.

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5 Comments
AnonymousAnonymousabout 8 years ago
Really enjoyed

One of the best things I've read in a long time would love if this became a series

CherieMCherieMabout 8 years ago
Love it

First story I have selected as a favourite :-)

AnonymousAnonymousabout 8 years ago
So enjoyable

I really enjoyed your tale. It might be the beginning of many chapters or maybe this was all you wish to share. Either way is good, although I sure hope you chose to continue with Rachel and Troy. Well done!

AnonymousAnonymousabout 8 years ago
more?

This could turn into a multi chapter series, maybe even a book. Really could have used more intro, but it worked out. Are you going to write more of not? I would like more, but not necessary.

Socially_IneptSocially_Ineptabout 8 years ago
Nice.

I wouldn't mind another chapter but it's not necessary.

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