Date: Wed, 15 Apr 2009 13:31:47 -0700 (PDT)
From: RE
Subject: In Over My Head Part 12

In Over My Head
Part 12
transgender/high school


An awkward silence fell between Joel and I, and finally he said, "I think
we need to get somewhere and talk. I have something I haven't ever told
anyone that I want you to know."

I figured it was the thing that Drew had told me about- Joel giving the
blow job to Danny and then Danny's brother, which I just learned was him! I
didn't say anything, since Joel needed to tell me himself if he wanted.

"I might have some secrets to share with you, too," I said, thinking that I
would finally let someone in on my secret world of Kyle versus Kylie. He
was suspecting something, anyway.

"Can I come over tonight?" he asked. "Oh, wait....I have to work tonight."

"It doesn't matter, you can come late after work. I stay up late, and my
mom's gone overnight again so I'm home alone."

It was hard to concentrate for the rest of the day, but when the bell
finally rang and I headed out, Justin caught up with me.

"Hey, what's happenin'?" he said, giving me a pinch on the shoulder. "Want
ta see my new truck?"

"Sure," I said, glad for the diversion. "Would you take me for a ride?"

"That's what I was hopin ta do," he said with a grin. I wandered if he was
implying something.

It wasn't an actual new truck, but it was new for him and he was very proud
of it. I almost had to jump to get inside it, and the mufflers roared when
he started it.

"You in a hurry?" he asked.

"No, I have all evening. My mom's gone, and I don't have any homework to
do."

"I'll show you where I live, then," he said, roaring out of the parking
lot.

It felt good to head out of the city and into a more rural area. The
scenary was great, and I liked the wind blowing on my face. Justin looked
hot, too- he had his cap on backwards, tight Levi's and his cowboy
boots. His hands were so big as they clutched the gear shifter. We pulled
into a farm with a large older home and several barns and sheds scattered
around. There was another guy that looked a little older than Justin
standing near a tractor, working on the engine.

"Who's that?" I asked.

"Oh, that's my brother, Jacob. He's on leave from the service- he's been
overseas."

As we got closer, I noticed how good he looked- really good! A lot like
Justin, but a little older with short blond hair and tanned skin. He was
wearing a muscle shirt and some camo pants and black work boots that were
laced about half way up.

"Let me show you the barn," he said, jumping out, and helping me
down. Jacob glanced up, then went back to work, while we headed out to a
large, red barn.

Justin showed me some of the horses and cattle, and let me sit on an old
tractor, then led me up a ladder to a barn loft about half full of bales of
hay. The hay and straw smelled fresh and clean. He sat down on a stack and
said, "Come here," and took my hand.

He spread his legs and pulled me closer- he was sitting on the bales of hay
and I was standing in front of him.

"You are so pretty, Kylie," he said, pulling me closer, and putting his
lips to my cheek. I felt his hot breath, and then he took my chin in his
hands and planted a wet kiss on my mouth. It was slippery, and slimy, and
it felt good. I hadn't been kissed for a while, and I parted my lips to let
his tongue explore my mouth.

"Mmmm, you taste so good," he panted into my neck. "I wish you'd let me do
what you let Drew do.......I know you won't fuck- he told me that. And
that's ok, some girls want to wait. But you let him do it in your
butt.....I wish I could do that...."

I remembered the size of Justin's cock and shuddered. I was able to get
used to Drew's six incher, but I don't think I could handle anything
bigger. Drew continued licking and kissing my neck, and massaging my
butt. It felt really good.

"I don't know, Justin," I said, holding onto the back of his head, "You're
really big, and I don't have any lube."

He pulled back and said, "I brought some, just in case. This stuff is
supposed to be really good." He pulled a tube out of his pocket. "Just let
me try- if it won't fit, I'll pull it back out of you. I don't want you
bleedin' or nothin' like that."

He kissed me again, and reached up my skirt and put his hands on my
panties, slowing pulling them down. I let him continue.

"Here," I said, unbuckling his pants and tugging on his zipper. "Lean back,
and let me put some lube on you. I don't know if I can do it, but I'll
try. You have to promise to stop if I tell you too."

"I promise," he whimpered, like a little boy. "I want you so bad...."

I pulled his pants down, then his shorts, and his dick flopped out. It was
even bigger than I remembered. I leaned over, and put the head in my
mouth. It was already dripping pre-cum. It tasted really good. He moaned,
while I licked it like a lollipop, and buried my nose in his ball
sack. After a few minutes, I squeezed a large amount of lube onto his pole,
and on the head.

I turned around, standing, and backed into him until I could feel his cock
head on my hole, then let out a long sigh as I tried to squeeze it in. At
first, it just wouldn't go, but I wriggled around until I felt a plop and
felt my hole open up to try and swallow the monster.

"Hold it there, a minute," I gasped. "Maybe it will stretch some." I moved
my butt in small circles, and felt him slide a little further as I went. He
let out a grunt as it buried deeper and deeper. It was really
uncomfortable, but I was surprised that it was actually going in. I could
feel it hit something inside of me that gave me a jolt, and then I pushed
until my butt was touching the inside of his thighs. It was in. It was
actually in. I felt like a....a shish kabob that had been speared- or a pig
on a spit. For a second the thought of a marshmallow on a stick came to my
mind. I realized that perspiration was dripping down my face, and I was out
of breath. It hurt with a dull throb.

"Damn, it really is in there!" he gasped, sitting up on his elbows, and
then straightening up further.

I waited a few minutes, then though I was ready to start pulling off. It
was so tight, at first, that I pulled him up with me, but then it loosened
and began to slip out. About half way I stopped, and pushed back down. I
could smell a scent coming up, and didn't know if it was him or me. It
hurt, but not as much as I was afraid it would. It just felt so....huge!

"Can you get on all fours, and let me do it doggy style?" Justin grunted.

I pulled off of him, and dropped to the floor, feeling very empty in my
newly stretched hole. He pushed off of the hay and knelt behind me, then
gently pushed it in until it had reached the end. I was seeing stars and
breathing in short gasps when I heard a deep male voice on the ladder:

"Little brother, what have you got goin' on here?!"

I was in way over my head, now.