Date: Wed, 25 Feb 2009 20:36:01 -0800 (PST)
From: RE
Subject: In over my head part 4

In over my head
Part 4
Transgender/High school

Part Four

I slept in on Saturday morning, and when I finally got up I saw mom's date
from the night before on his way out. He didn't look too bad! Especially
with his clothes back on. I had breakfast and got the rare opportunity to
chat with my mother for about an hour or two. She was home for the weekend,
and agreed to drop me off at the mall in the early evening. I figured I
would go in my 'guy' clothes, then slip into a restroom and make the switch
after I got there, hoping I wouldn't see any faces from school in the
meantime. In a city this size, it wasn't too likely, if I was careful. I
told her that I was meeting friends and wouldn't need a ride home.

I headed straight to a private handicap bathroom so I would have some
privacy, and made the change over, putting my other clothes in a shopping
bag. It was 6pm and Drew worked 'til 8pm, so I had some time to kill
picking up some more female accessories. At 7:30pm my phone buzzed with a
text message, and I read:

Drew: It is dead here. No customers for the last hour.  Drew: I'm the only
one here- I have to close up shop.  Drew: Are you coming?  Me: Yeah, I am
walking over there right now.

I stopped in a ladies room to check make-up and hair, and put on some extra
perfume before heading across the parking lot to the strip mall where
Drew's electronic store was located next to a hair salon and video store.

"Hey darlin'," he smiled, as I walked in.  "Hi," I answered, "Are you
working hard?"  "It's dead here- I have already started shutting things
down. C'mon back and I'll show you around."

He gave me the grand tour, which took about five minutes, and then I sat
down in an swivel office chair while he ;locked the doors and started
closing out the cash register. He was in a uniform shirt and black dress
pants. His butt looked so good as he bent over the register.

"Are you staring at my butt?" He asked without turning around.

"No.....well, maybe...yeah," I answered, "How did you know?"

"Reflection on the computer monitor, I could see you," he answered. "You
like it?"

Embarrassed, I didn't answer.

"That chair rolls, ya know," he said, while working. "Why don't you roll it
over here....I been on my feet all day. I could use a little massage."

I pushed away from the wall, and rolled over to where he was working, and
got behind him. Reluctantly, I reached out and rubbed the lower part of his
back, which was a little above my reach.

"Oh, that's good. Go lower....lower," he said, leaning further down, as I
rubbed his butt cheeks. They were firm- a little skinny, in fact. He moaned
as I kneaded them like playdough.

His hands were almost shaking, as he wrote on the cash register tickets
with his pen. I reached forward and bit him playfully on his butt cheek.

"Ow!" he laughed, "What are you doing? You're into this, aren't you?"

I reached around and unfastened his front buttons and unzipped his
pants. He wasn't wearing a belt. Gently, I tugged them down.

"Stop," he laughed, "What if someone comes in?"

"The doors are already locked and the main lights are off," I giggled,
continuing to pull the pants lower, until I could see the top of his
crack. His skin was whiter here than the tanned look on his face and arms,
and it had some light fuzz over it. It smelled a little musky, but I could
smell the fabric softener on his boxer shorts, too..

"What are you doing?" he laughed, without turning around.

I pulled the shorts a little further, and kissed a butt cheek, then planted
my lips on it and sucked pretty hard, while reaching around for his
cock. It was rock hard. I then kissed his butt again, while pulling on his
rod. By now, he wasn't paying any attention to the cash register. He had
both hands of the counter, and was holding on tight while I pulled his legs
apart, and rolled the chair forward until he was almost straddling the two
side arms of the chair, his pants all the way to the floor.

I had never had a guys butt right in my face, and I was sure what to do,
but I had went too far to turn back now. I kissed him again, then pulled
his butt cheeks apart and kissed his hole. It was moist with some
perspiration, but it was obvious that he kept himself pretty clean. I
kissed it again, then stuck my tongue out and licked it. He yelped and
jerked, then pushed harder into my face, as I licked a little deeper, and
continued masturbating his cock.

"Oh, nobody EVER did that to me before," he moaned, spread his legs a
little further. "Owww....that is sooo hot." He started rotating his butt in
small circles as I licked and kissed it, while pumping his rod.

"You gotta stop," he laughed, pulling forward. "I can't take any more of
that...it's too...too intense!" He stepped forward and pulled up his pants
and snapped them. "Plus, we might want to do something else later, and I
wanna save my juice for that," he winked. "You're not still on it, are
you?"

"Fraid so," I lied. "It lasts a couple of days. Sorry." I wiped my mouth
off with the back of my hand, probably smearing the lipstick.

"Oh." He sounded disappointed. "Ok, well, let me get finished here and
we'll go eat something."

I wandered how long I could keep this at bay- I was going to have to come
up with a plan of some sort.

After Dinner

We at at a sports grill not too far away, and several times Drew put his
hand on my back and leg. I felt tingles every time that he did. Once, he
reached over and kissed me on the head and said, "You smell so pretty."

After dinner he asked if I wanted to drive back to the Lake. Since we
couldn't go to my house or his, the options were pretty limited. I asked if
we could go to a late movie, instead. We drove by the cinema, but the next
film didn't start for another hour, so I took a real chance and called my
house to see if my mother answered. The answering machine picked up, so I
decided to invite him to my house. I thought that we would hear my mother
if she did arrive while we were there, and we could go to the family room
in the basement. If she came in, she would just think that I had a friend
over for a video game. There weren't really any family photos to worry
about on the wall, so I thought my secret was safe.

He parked on the street, and we went in the house and down to the family
room to put on a movie with the volume down low. Once we settled on the
sofa, he pulled me close and said, "I have wanted you all day," and he
kissed me slowly. "I can't believe you did that thing with my butt while
ago..." he giggled, "you are a dirty girl."

"You do it to my," I said, snuggling up to him.

"I wish I could fuck you, babe," he said, staring in my eyes. "I want to be
inside of you so bad."

"Maybe later," I lied. "I can't do it while I'm on a period. It wouldn't be
good for either of us."

I kissed him again, then kissed his neck, and unbuttoned the top of his
uniform shirt, almost sitting in his lap.

"I got a buddy that said he screws his girlfriend in the butt, when she's
on it," he whispered into my hair. "I bet that would hurt."

"Wouldn't hurt him," I said, "But I bet it hurt her."

"He said she likes it...sometimes better than the other way," he said, and
I knew what he was suggesting.

"I don't know. Ouch," I smiled, and kissed him, sliding down between his
legs and slipping his shoes off, and rubbing his feet. I wandered if I
could pull it off- doing anal, and him not finding out that I had a dick. I
would have to leave on the girdle and keep his hands away. Plus- wow, what
if it really hurt?

I thought that maybe I better not take the chance. But then, I wanted to
feel a guy INSIDE me, inside my body. That would be so cool. I kept rubbing
his feet, and laid my head in his lap, as he stroked my hair. I slipped his
socks off, and rubbed his feet.

"Oh, that feels good," he moaned. My feet hurt from being on them all day
long."

I had never touched another guy's feet- I had only seen them at the
swimming pool or in the locker room. His feet were thin, and his toes were
long and about even lengths.

"They're really dry," I said, let me put some hand lotion on them. I
reached over to a tube of lotion next to the TV screen and smeared it on my
hands. As I rubbed his feet and pulled on each toe, he leaned back and put
his arms behind his neck.

"It don't get better than this," he smiled. "A pretty girl at my feet."

I held his foot up and kissed it lightly, smelling the leather from his
shoes, mixed with the smell of lotion and a little bit of perspiration. It
was more of a turn on for me than I thought it would be, and gently sucked
on his toes before putting his foot back down.

"Stand up and turn around, I wanna see your butt," he instructed.

I stood up, then warned him not to touch me in the front because of my
'tampon' pad. He promised that he would stay away from that area
completely.  He put his hands up my skirt, and massaged me as I bent over
slightly. It felt really good. He slid my panties down, and now it was skin
to skin- his hands just a little bit rough.

"Hand me your lotion, there," he said, and I passed the tube to him. He
squirted it on his hands and rubbed it onto my butt, then up and down my
crack.

"You like that, don't you," he said as he worked, and I felt his finger on
my hole, gently prying. He squirted more lube on his finger, and then
pushed it in slightly. "That hurt?" he asked.

"No," I said truthfully, "It feels weird, but I like it."

He slid his finger in a little deeper, as he continued to massage my butt
cheeks, and kiss them lightly. I felt him slowly going deeper and
deeper. It was uncomfortable, but it didn't hurt too bad. He slowly pulled
it out, put on a heavy coat of lube, and worked to get two fingers in. This
time it hurt a little more, but seemed looser than the first time.

"Do you still like it, babe?" he asked.

"Yeah, I think so," I answered truthfully.

"Think you could take the real thing up there? I'll be really gentle, if
you let me try," he promised.

"I don't know- how do I do it?" I asked, shaking slightly.

"Why don't you just sit down on it- I'll put a lot of lotion on my pecker
first, then you sit on it and let it slide in slowly."

"Ok," I said, wandering what I had committed to. "If it hurts too bad, you
have to stop, ok?"

"Absolutely," he purred. "That's the last thing I'd want. Now pull your
skirt the rest of the way off, and squat down over me- I will guide it up
to your hole."

I obeyed, and in a few seconds, I felt a blunt instrument pushing its way
into my body. In a moment there seemed to be a 'plop' and I felt the head
slide in. I closed my eyes, and let out a long breath, then let my weight
push onto it.

"Slow, go slow," he murmured. "Get used to the feeling. You might need to
stretch some."

"Ok," I gasped, "So far I'm ok. It just feels so huge."

"You can do it, it's not that big," he said, as I continued sliding down
the pole, feeling fireworks combined with a splitting sensation. Finally, I
reached what I thought was the bottom, and leaned back against his chest.

"Oh....I really did it!" I said, laughing, and feeling like we were
connected to each other. I wandered if it would ever come out, or if we
were stuck. It felt weird knowing that a part of Drew's body was inside of
my body.

"Stay this way a few minutes before we move," he said, "And get used to
it."

After a few minutes, I said, "I think I can do it now. Really slow." I
pushed on my tip toes, and pulled up from his cock, and it reluctantly
starting sliding out, then gently I went back down again. There were sharp
pains as I went back down, but they were endurable. He put his hands under
my butt, and helped push me up, then let me push back down.

"This is incredible," he moaned, "It is so unbelievably tight, and hot."

Just hearing his moans, made me want to service him, even if it still
really hurt, and I increased the tempo, biting my lip. For good measure, I
threw in some groans too.

"Is it good for you too, baby?" he asked.

"Oh, yeah. It's good," I grunted, not sure how honest I was being- but the
whole experience was a turn on, and it was getting a little easier.

"Bend over and touch the floor with your hands- let's try it that way," he
suggest.

He slipped out as I got onto my hands and knees, doggy style, then
re-entered with a shove.

"Spread your legs a little more and let me ride you," he said, putting his
hands on my shoulders. I was now completely at his mercy, and he was
getting really horny. I guess he figured my iniation was over, and it was
time for some serious intrusions, because he pushed in all of the way, back
out until he was almost to the head, and then back again.

"Oh man....that is sooo deep, baby!" he cried, with his ball sack slapping
me as he penetrated deeply. "I'm about ready to bust a nut......"

 He shoved one more time, the deepest thrust yet, and held it there as he
shook and spasmed. I knew he was climaxing as he tensed his entire body,
then slumped onto my back.

We laid there, breathing heavily, for several minutes. As his cock
softened, it was gradually expelled. He leaned back on his haunches, and
pulled my butt cheeks apart again, inspecting his handiwork, and touching
it with his index finger.

"Does it hurt? I hope I didn't hurt you," he almost whined, in a hoarse
voice.

"No, I'm ok," I said leaning back into his arms and sitting on my sore
butt.

"Well, I left sumptin' inside of you, babe," he whispered in my ear, but I
don't think you have to worry about gettin' pregnant."

"Hah, yeah, right," I answered, snuggling into his neck. I wandered if what
he 'left in there' was leaking out.

The door at the top of the stairs opened, shining a light down into the
family. I heard my mother's voice calling down,

"Kyle- what are you doing down there?"

Aw-oh!