Date: Thu, 11 Sep 2008 15:52:13 -0700 (PDT)
From: Tommy Woodland <soxandundyguy4@yahoo.com>
Subject: i love to show off - 4

i love to show off - 4
Tommy Woodland
soxandundyguy4@yahoo.com

Fall is my favorite time of year because I get to go back to school. I know
most boys hate it, but I love it. Not because I love the classes, but
because I love showing off in front of the other boys and my teachers.

Dad had bought me new uniform clothes for school, and for some reason he
bought them like three sizes too big. I guess so I would grow into
them. Like they would last that long. He told me I had to wear a belt with
my trousers to keep them up, so the morning of the first day of school I
put one on. Then as soon as I left the house, I took it off and dropped it
down a sewer drain.

So as I am walking to school, I could feel my pants sliding down. I took
two more steps and they slid down to my ankles, exposing my new blue and
white underpants. I left my trousers down long enough for people driving
past to see, then pulled them up again. After a few more steps, I let them
drop again, and once more waited a couple of minutes before pulling them
back up.

It was exciting having my underpants exposed like that as I walked down the
street, especially seeing all the men driving to work who got to
see. Finally I pulled my pants up and held them up as I walked. But then I
could feel my shoes, which dad had also bought too big because he said my
feet were still growing, coming off as I walked. My heels kept popping out
of the shoes, and sometimes my foot would be half-way out before I caught
it. Then I felt my socked feet come all the way out of my shoes. I took a
few steps on the concrete sidewalk in my socks before I realized, then I
went back to put my shoes back on. That happened several more times as I
walked to school.

When I went to homeroom and sat down, I realized that most of the other
boys had grown over the summer, but I was still pretty small. Now most of
the other boys in my class were a lot bigger then me. I could hear a few of
them snickering at my oversized-clothes. When we stood up for the pledge of
allegiance, one of the boys yanked my pants down to my ankles. The boys
around me all laughed until the teacher glared at them. I just stood
through the pledge in my underwear, pulling my trousers up as I sat back
down.

The bell rang for first period, and we all headed to our first class. The
hallway was crowded, and I could feel boys stepping on my shoes, popping
the heels off. Then as I walked I felt my feet come out of my shoes. I
looked down, but the halls were so crowded my shoes got kicked away and I
couldn't find them. I had to walk to first period in just my socks.

By the time I sat down in my desk for first period, I had a boner tenting
my pants. I lifted myself up off my seat enough to pull my pants down. They
were so baggy they slid down very easily. So then I could sit through class
rubbing my hard-on through my underpants. A couple of boys nearby noticed
and snickered. I didn't cum yet, though.

At the end of the day they called the entire school for an assembly - a
sort of a welcome back to school thing. So all us boys went to the
gymnasium where we had to pile onto the bleachers while the principal stood
on the gym floor talking to us. There were so many of us that we were all
crammed together; none of us could even sit down it was so tight.

We were all standing crowded together on the bleachers when I realized my
pants were coming down again. But I couldn't move my arms to grab them, so
after a few minutes, my trousers slid to my ankles. Then some boys who were
rough-housing jostled the crowd, and I got pushed. When that happened, my
feet came right out of my pants, and I had no idea where they went. I
couldn't see or feel them. I was now standing in the crowd of boys in my
shirt, underpants and socks.

Naturally I got a boner that tented my undies. We were all so tight that my
hard-on was pressing up against the rear end of the boy standing in front
of me. I could also feel that the boy standing behind me had an erection,
and it was pressed up against my butt. I tried to see who was behind me,
but I couldn't really move.

Every time the crowd of boys was jostled, I would get pushed harder against
the boy in front of me. My dick rubbing up against him felt great, and I
was getting more and more excited. The boy didn't seem to notice, I guess
from all the movement around him.

Then I could feel the hands of the boy behind me on my briefs. I realized
that his arms were pinned to his sides, but he was able to reach far enough
in front of him to pull my underpants. He began to slowly tug on them, and
I could feel my undies sliding down. Soon my boner popped free of the
elastic, and my dick was rubbing directly against the trousers of the boy
in front of me. It felt great, and I was getting even more excited!

The boy behind me began to thrust his hips forward, grinding his crotch
into my naked butt. That made me push forward, and the friction of my dick
against the pants of the boy in front felt awesome. We did that for several
minutes, both of us grinding our cocks, his against my rear end, and mine
against the boy standing in front of me.

Since I had been edging all day but had not cum, I could feel all my
pent-up jizz building up. With the boy still rubbing against my butt, I
thrust my dick forward and the first stream of cum shot out. It shot so
far, it landed all over the shirt of the boy in front of me. I kept
grinding my hips as the rest of my load shot out, spurting cum all over the
boy's pants. By the time I had ejaculated every drop of jizz, the boy in
front of me was a wet, sticky mess. I could feel the boy behind me quickly
yank my undies back up.

The assembly ended and the boys began to disperse. I was able to sneak down
under the bleachers where I found my pants. Luckily the boy in front of me
didn't see who was behind him, because all of the other boys began to laugh
at the cum all over the back of his shirt and pants. I also got a glimpse
of the boy who was behind me; he was a new boy I had never met.

I managed to find my trousers and get them back on. Before I left school I
checked the lost and found, and my shoes were actually there. So I put them
back on and headed home.

On the way home the new boy who had been behind me came up and introduced
himself to me. It turned out his name was Shawn and he had moved in just a
couple of doors down from me. He had been following me on the way to school
that morning, but I had not noticed him.

As we walked home and were talking, my oversized shoes kept falling off my
feet. Finally I stopped, took them off, and put them in my backpack. Shawn
giggled and said that looked comfortable as his shoes were hurting his
feet. I watched as he sat down, untied his shoes, pulled them off, then
tossed them into his backpack as well. The two of us continued on in our
school dress socks, enjoying the feeling of the concrete through the nylon
material.

A few minutes later my baggy pants fell down again, and Shawn giggled once
more, saying that he liked my undies. I blushed but thanked him, liking the
attention. He invited me to put my hand inside his trouser pocket, and when
I did, I realized that he had cut the pocket out. I was feeling his
underwear! He giggled and said he cut the pockets out of all his pants so
he could play with himself all day. I had a feeling we would become good
friends.

When my pants fell down again, Shawn laughed as said it would be fun to
walk home in just our underwear. I agreed, so we both undressed right there
on the sidewalk, stuffing our uniforms into our backpacks. We walked the
rest of the way home in our socks and underpants. Occasionally a car full
of boys would see us and honk or yell "fags" out the window.

I walked Shawn to the front porch of his house. He said he would invited me
in sometime, but couldn't now because his big brother would be home. Then
Shawn suggested that we swap underwear and wear each other's to school
sometime. I agreed, and we both dropped our underpants. We were both
standing totally naked on his front porch.

Before I could get his undies on, Shawn reached out and grabbed a hold of
my dick, making it throb in his hand. So I took hold of his, which was
twitching in my hand. We pumped each other's cocks for a couple of minutes,
then suddenly we both exploded, shooting cum all over his porch. Little did
we know that his big bro was watching through the window.

We shot our loads, and I pulled on Shawn's briefs and ran home in just the
underwear. I knew I had a new friend.

Soon my favorite holiday would be here, Halloween. Last year I had had a
great time when my Uncle Frank took me trick-or-treating. I dressed as a
ghost with a sheet over me. The only thing I wore under the sheet was a
pair of white socks and a pair of Halloween undies with pictures of bats on
them. Anytime we went to a door where another boy or an older man answered,
Uncle Frank would life up my ghost costume so they could get a peek of me
in my underwear.

This year dad said I was too old for trick-or-treating, but Uncle Frank
promised to take me to a Halloween costume party. One Friday after school
my uncle picked me up to take me shopping for a costume. We went early
while there were still plenty available.

Uncle Frank was helping me find costumes and try them on in the store. I
didn't bother going into the dressing room; I just undressed to my
underwear and socks in the store and walked around like that shopping so
that I could just try on a costume as I found one I liked. Uncle Frank was
friends with the owner of the costume store, so he didn't mind.

I tried on all kinds of costumes, including a fireman, a policeman, and a
superhero. I liked that one because it was skin-tight and almost like
wearing nothing but my underwear and socks. I also liked the toga because
it would show off my undies when I moved around. But I couldn't decide, and
then Uncle Frank said he thought of the perfect idea.

He talked to his friend, and the found a couple of things and brought them
to me. Uncle Frank told me to leave my white socks on, but he pulled my
underpants off right there in the store. He gave me a pair of tightie
whities to wear instead, then he put a button-up pink shirt on me. He told
me I could go to the party as Tom Cruise in Risky Business. I didn't know
what he meant, but Uncle Frank and his friend liked it, and they told me I
could wear just my underwear all night, so I was happy!

I was disappointed I still had to wait a few weeks for the Halloween party,
but to make me feel better, Uncle Frank so I could wear the outfit for the
rest of the night. We left the store, and my uncle had my other clothes in
a bag so that my dad wouldn't get mad later.

Uncle Frank and I walked down the street so that we could something to
eat. It was fun walking around like that in just my underwear, even though
the shirt was long enough it covered most of my briefs. Whenever we walked
past guys, I would lift my shirt up so they could see my tightie whities.

My uncle didn't notice when I started to pull down my underpants as we
walked. The briefs slid down, then fell to my ankles, and I walked out of
them. Now I was walking half naked which felt great! I had a boner, and
when an older man walked past us, I would lift up the shirt to he could see
my hard-on.

We got to the restaurant and took a seat in a booth. I unbuttoned some of
the bottom buttons of the shirt. From above the table it looked like my
shirt was buttoned up, but underneath it was undone, clearly showing that I
was naked beneath the shirt, except for my socks.

The waiter walked up and saw my exposed boner, smiled at me, and told my
uncle that we could eat for free. After we placed our order and he left, I
noticed a dad at another table sitting with his son. But the dad was paying
more attention to me than his own son!

Uncle Frank asked me about school, and I told him what happened in the
assembly. As we talked, I reached under the table to I could play with my
boner. After a bit I told uncle Frank that the shirt was uncomfortable and
asked if I could take it off. He said yes, thinking I still had underpants
on. So I unbuttoned the shirt the rest of the way and let it drop to the
floor. I now sat naked except for socks in the restaurant. It was very
exciting and I couldn't stop masturbating! Anytime a man walked in he
looked, and I smiled at them as I jacked off. The man at the other table
was also playing with himself as he watched me.

After a bit I noticed the dad talking to his own son, and then the boy
turning to look at me naked and playing with myself. The boy and his dad
talked for a minute, then his son laughed at began to take his clothes
off. He kicked off his sneaks, pulled off his jeans, then took off his
shirt, dropping everything on the floor. He was wearing a cute pair of
Wall-E Robot briefs like I had just bought recently.

Finally it was time to leave, and I had been playing with myself and edging
the whole time, so I was very excited and dripping pre-cum. Uncle Frank got
up and I got up too, still naked, to follow him out. Suddenly I stopped
right in front of the table where the dad and his son sat, and without
touching me boner, I started to cum! Uncle Frank, the dad, and the waiter
all watched as I stood naked in the restaurant, shooting my jizz all over
the floor. I couldn't stop it, and it felt so good! I looked at the man's
son, still sitting in his underpants, and as he watched me his body
twitched a wet spot began to spread across the front of his undies.

After I had shot my load, Uncle Frank led me out, saying it was a good
thing he still had my other clothes. I was sorry I had to wait for the
costume party, as I knew I would have fun with Uncle Frank.