Matthew/Maria

I’m Matt, now known as Maria, and this is the story of my journey of how I became a shemale, and all the quirks, and bumps in the roads. Now that my name is out of the way, I will explain a little more about myself. I’m a 15 year old male with an unusually small cock at 5 inches, and a index finger girth, along with my premature ejaculation, well how can I say this? My sex life FUCKING sucks. I have long, straight, mid-back length hair. My tiny frame is also a killer, 5’4 and 105 pound’s. As you would expect, most people tower over me, and life in general has just sucked.

Sometime last year I discovered a new type of porn, shemale, or transsexual porn. That soon led to anal play, at first just with my finger, that was until I was home alone, at least I thought, for the weekend.

I thought I’d snoop a little since the chances of getting caught were slim to none, or so I thought. My sister was sleeping over at the cheer captains house with the rest of her cheer group. My parents were in Berkeley on business for their company.

So, first up was my parents room! Overall, it was pretty fucking boring, except for the 90″ inch Toshiba in their room, Fucking assholes! I would kill for that shit. I walked over to the dresser on the left, a vintage one that was built in the 1920’s, again pretty boring, then again it was my dad’s. There was a few porn mags, however. Now to moms dresser! Granny panties, bras, ugly clothes. Nothing special, I looked around for a while, nothing special.

On to Katie’s room! Her room was a bit better, posters of pop punk bands, deathcore bands, and so on. Closet time! The buried treasure is found at last! Silk thongs, bras and buried under all of that was a purple, (probably) 8 inch dildo, a bottle of lube, and condoms, “how in the fucking hell did a 16 year old get a hold of this?” I thought to myself.

I at this time was smelling, and feeling her panties, I got a gut feeling in my stomach, I looked back on all the shemale porn I had watched, and their bras and panties. I wondered how it felt to wear women’s clothing,

I swear I must have been naked faster than a cop eats a doughnut, my tiny cock was hard, I slid a pair of pink, silk panties on. As soon as the silk slid under the head of my penis, cum started spewing out of my third eye, all over the closet mirror, floor, and her panties. I laid down on her bed, resting and regaining my composure. When I sat up, cum was everywhere.

“Fuck” I muttered

With a little trouble, I put on a bra, which in all honesty was to big. I started to taste my cum, but decided to smell it first. It didn’t really smell like anything, however, it tasted pretty salty.

I stood in front of the mirror, looking at my body in women’s clothes. I imagined myself as a woman, with tits, and a pussy, however, I still wanted a cock. How could that be plausible?

Then it hit me like a train, or getting ran over by a pile of football players. I could become a shemale! I looked down and my cock (if you want to call it that) was hard. Then I remembered the dildo, I smeared my asshole with some KY jelly as well as the dildo, I stuck two fingers in my ass to get ready for this monster, comparatively speaking to my dick.

I then stuck a third finger in, and I knew I wanted to be shemale. I put the head of the dildo up to my fuckhole and pushed a little. The head went in. I shook in utter pleasure as it went further in. I was going to cum when…

“Hey, Matt, what are you doing?” She asked with a sly smirk.

It was far to late, I blew my load, It blew all over my stomach, Katie’s bra, a little on my chin and more on her panties. I laid my head back, “FUCK! FUCK! FUCK! FUCK!” I screamed to myself.

I opened my eyes, she was sitting next to me now, I could not read her face for the life of me. It was like a mixture of concern, awkwardness, and whatever else.

“Wh-what are you doing home Katie?” I stuttered in embarrassment.

“Alissa had to go to the hospital, for alcohol poisoning or something like that, serves the stupid, stuck up cunt right, I guess” she said

“And…baby bro, stop trying to change the subject, when we both know your a kinky gay boy!” She added

“Katie!…” I paused

“….” I didn’t speak

“…”

We both looked at each other in an awkward silence, I don’t know what happened, I just couldn’t put the exact words I wanted to say together.

“It-It’s not like that…”

“Then tell me exactly what you are doing with my bra and panties, and you being soaked in your own cum with MY dildo still stuck up your ass?”

Wow the emphasis on ‘MY’ stung a little. You see, my sister and I have always been close, to the point that we can talk or tell eachother about anything. When we were children, we would play doctor or the good ol’ ‘truth or dare” until we were caught, we never did it again after that. Anyways, back on subject, I felt like telling her my new feelings would take it over the line of normal, and she would never acknowledge me again and I couldn’t have that.

“Katie, I can’t tell you…” I said.

“Matt! Your lucky I’m the one who caught you! If dad caught you like that then he would probably disown you for the rest of his life, so can you please tell me what’s going on with you?” She asked in a concerned tone.

“I’m afraid if I tell you, it will ruin our relationship, and it will never be the same…” I said

“Matty, I’d never do that, well..unless you murdered someone, wait! Did you…”

“No, I didn’t murder anyone or anything, Katie.” I interrupted her

“Oh..” she said

“So Matty, now that we got that out of the way, please tell me?” She said with her infamous puppy dog eyes that ended up getting her everything she wanted.

“Fine!” I said

“Go on..” she said with a smartass look.

It felt like I was sitting there for years, no, more like decades. In reality it was only seconds.

“I-I want to be a wo-woman…” I said disheartened, and somewhat depressed and embarrassed.

As much as I didn’t want to to see the look on her face, I did anyways. Her eye were opened widely, and had a small smile, I guess she was trying to make me feel comftorable. It was quiet, I looked back at her, she now had a full smile, not just a regular smile, but one of those, ear to ear, all teeth smiles. This time she cheered me up a little.

“Matty, I told you this wouldn’t change anything, and it hasn’t, I love you and that will never change” she said tearing up a little.

“I love you to Katie” I replied with my mood rapidly heightening.

I went in for a hug, before I got interrupted by Katie, “don’t touch me ’til you take shower Matty”

“Anyways, go take a shower, and let’s go do something!” She said

“Oh and keep the bra and panties” she said with a sly wink.

A few minutes later I jumped into the shower, resting against the wall of the shower, I thought about everything that had happened today. I let the hot water soothe my nerves and drown my worries for a while.

Getting out of the shower I heard Katie saying bye to someone, probably talking to Alissa’s mom on the phone I thought. I dried up, put on some clothes, and then went into the living room to see Katie in a tight dress, knee length, black, and leather.

“So, where do you want to go?” I asked

“Movie, or a dinner?” She said, pretty much thinking out loud.

“Both?” I recommended

“Sure, why not” she said rhetorically

We left a while later, and saw “The Apparition”.

Afterwards…

“Seriously? They call that a movie?” I asked

Katie was silent, which really wasn’t different, she was always quiet while driving (typical female driver eh? Kidding, kidding).

“That’s the worst excuse for a movie I’ve ever seen!” I bluntly scolded the movie

Katie was still silent. Now this was getting unusual, and a little weird, being that I was talking to myself.

“Katie? You okay?” I asked

I was starting to get a little worried about earlier and maybe her mind has changed about it.

“Umm, Ye-yeah, can we talk about earlier?” She asked as we pulled into a IHOP.

“Yeah, sure” I said a bit awkwardly.

We walked into the building, empty as fuck, the waitress took us to the back, and we sat, ordered our drinks and looked at eachother.

“So, what is it Katie?” I asked timidly.

“Are you sure you want to do this?” She replied

It took me a minute to reply, gathering the words, and re-playing the words throughout my mind.

“Katie, here’s my answer, yes, to be honest, I’ve never felt right as a guy, and when I started watching these videos..”

“What kind of video’s?” She interrupted

“Shemale porn” I whispered to her.

“And as I was saying, when I watch those videos, I feel like that’s where I want to be, what I want to be, it just feels right.” I said.

‘So, you want to be a cut your dick off women or what?” She asked.

“No, no, I want to keep my penis, but I want to look like a female, therefore a shemale, get it?” I asked.

“Yeah, and whatever you decide to do Matty I support you, and I’m going to help you. On one condition…” She said.

“What is it? I asked

“You need to tell mom and dad, and if you do that, even if they don’t want it, I will still help you.” She said

My jaw dropped, the one thing I didn’t want to think about doing shes going to make me do.

“I don’t know Katie…” I said

“Matt, I’m fine with you doing this, but i will only be ok if you tell mom and dad”.

“Fine, I guess I will Katie”. I said

I looked at the clock, it was 1:30 A.M ! We had been there over two hours!

“Come on let’s go” I said

Now Katie was smiling again, and seemed much happier.

“I got a surprise for you tomorrow, so get some sleep Matty” she said as we pulled into the driveway.

We walked up to the house, mom and dad were home earlier than expected also.

“Now aren’t you glad I was the one who caught you, baby bro?” She blatantly said.

“Yeah, I guess haha” I replied.

So my sister and I sat out front for a while, I had a cigarette.

“Katie, when do I tell them?” I whispered

“Not now, i’ll tell you when Matty” she replied.

We went in finally, mom and dad were on the couch watching T.V. until we came in, they had a worried look on their face. Not the kind that says ‘Do you know what time it is?!’ But more like the ‘Where were you guys? Did you have fun? What did you do type look.

“What did you guys do? Did you have a good time?” Dad asked.

I just couldn’t for the life of me, look my dad in the eyes, without him knowing the truth. I ran to the bathroom and puked, not that I had much inside of me, but whatever was, was gone now. My sister was the first to come, probably being the first to realize I ran off. She was holding me tightly.

Not a minute later, mom and dad ran in. that’s all I remember really, I basically passed out their on the floor. Someone must have carried my lithe frame to my room, because I woke up in my bed. I sat up, dry mouth, and groggy as shit. My mom walked in, I guess to check on me.

“Hey, Matt, how are you doing sweetie?” She asked

“Fucking movie theatre food” was the only excuse I could think of on the spot

“Well, Matthew, breakfast is ready and everyone else is awake” she said.

“OK!!! MOM!” I said as I threw a plastic water bottle at her, not seeing where it went.

I sat up and BLAM!! Like a bowling ball to the face, all the memories of last night hit me. I changed and went downstairs, everyone looked at me, but still I couldn’t look at dad. I ate next to Katie who kept giving me that ‘everything will be ok’ look.

After I took a shower, and dried my hair, got dressed, I went out to the backyard to smoke, soon after, Katie came out and sat down next to me, giving me a smile that said ‘I know something you don’t’.

“So, Matty, you are coming to the mall with me!” She said.

“And why Is that Katie?” I asked

“You’ll find out when we get there!”

She then skipped off back into the house to do god knows what.