Credit: https://www.nifty.org/nifty/transgender/she-male/shemale-surprise Wolf
This story is a work of fiction and contains descriptions of
explicit sexual acts of boys and men discovering their
sexuality. It contains graphic scenes of sex between
consenting underage boy and adult males... If this type of
content offends you or you are under the age of 18 do not
read it.
Author's Note:
This story is the property of the author. It can be downloaded
for personal reading pleasure or sending to a friend, but if
you wish to re-post them at your own site, please contact the
author for permission.
Copyright 2017 Wolf, All rights reserved.
You may contact me at pomowolf74@yahoo.com if you like.
All flames will be ignored.
Shemale Surprise
By
Wolf
I was a shy boy, named Jacob, as a result I did have sex
until I was eighteen-years-old. Growing up as an only child of
strict southern fundamentalist parents meant that I was
severely punished when they caught me masturbating.
Shame stayed with me all of the time because I couldn't stop
playing with myself. I felt like there was something wrong
with me.
We lived in a rural area, so there were no children my
age to play with. At school I was too embarrassed to talk to
girls. Even if there was a girl that was interested in me I
didn't recognize the signals.
Hiking allowed me to get away from my parents so that
I could masturbate in the woods. Lifting dead weights
developed my upper body. I developed a 48-inch chest, 20-
inch bisects, 34-inch waist, 44-inch ass, 26-thighs, on a five-
foot 11-inch frame.
Upon graduating from high school I convinced my
parents that I wanted to go to college in another State
because I wanted to get away from my parents. I was told
that if I wanted to go to college I had to do it on my own.
They were not going to play for my college.
I applied to a University 2,000 miles from home and
was accepted. I worked hard all summer to save up as much
as possible. I had to live as cheaply as possible. I lived in a
cheap apartment in a rough neighborhood, commute by
public transportation. I found a job that would allow me to
take time off for classes.
It was a warehouse job that required stacking 52 pound
empty steel barrels after they were painting. My build was
the reason I was hired. There was another guy working with
me in the barrel house.
He was an intimidating guy when I first met him. His
name was Donald. He had a build every bit as strong as mine,
but his arms, chest and back was covered with tattoos. His
head was shaved and he sported a dark mustache with a
goatee and always looked like he had a three day beard. But
working with him I found that he was a nice guy. We
developed a pretty good friendship. He encouraged me to
stay in school.
During lunch-brakes we found that we shared the
interest in weight lifting and the outdoors. . He seemed to
be as shy as me, because we never allowed the other to see
us use the bathroom facilities. That would change after the
first academic year.
The university was on a quarter-system so after the
spring quarter there was a week break before the summer
quarter. Don invited me to go backpacking in the mountains
with him. Getting away for a few days was just what I
needed, so I accepted.
I was an experienced hiker, so I packed my backpack
for a three day outing. The weather was balmy, so tents
wouldn't be needed. I simply packed a plastic tarp to sleep
to use as a ground cloth, or make a shelter if it rained. I pack
as lightly as possible. My down sleeping bag weighs only 1.5
pounds.
Don picked me up at my apartment in an old Ford
pickup and I tossed my pack in the back with his. He was
wearing shorts, so I saw the tattoos on his legs for the first
time.
It was a four hour drive to the parking lot at the head
of the trail. We locked up the truck and saddled up for the
hike up the trail. We were in no rush, so we took our time
hiking up the trail, stopping to drink water and enjoy the
sound of birds and the sound of woodpeckers hammering
holes in trees.
It is unbelievable how loud the sound of a woodpecker
carries in the woods. It sounds like someone is chopping
down a tree with an ax.
The air is desiccated and my nostrils were dry and filled
with the smell of cider and pine trees. The trail made a lot of
switched backs and came close to a stream with cold running
water, so refilling our water bottles was no problem.
When we met other hikers coming down the trail we
exchanged pleasantries. Don knew the trail, so when he
chose to take a fork in the trail that led to another peak I
simply followed. This trail was rougher and we didn't meet
any hikers. When we reached a small valley with a small lake
he told me that we would camp there tonight after we reach
the peak.
It took another couple of hours to reach the peak. We
were well above the tree line and had a 360 view of the
forest below. There was a 50 caliber ammunition can chained
to the peak with lined book and pencil in it. We signed the
book and dated it. We sat on the rocks ate our lunch and
enjoyed the view. At that altitude it got uncomfortable cold
as soon as our bodies cooled off. We pulled out
windbreakers to keep warm.
Eventually we started back down the trail. When we
reached the small lake we went around the lake to get as far
away from the trail as possible. We simply laid our ground
clothes on a relatively flat area, and unrolled our sleeping
bags to air out and allow the down fathers to fluff up. We
stuffed our puffy jackets into our sleeping bag stuff sacks to
use as pillows.
We broke out our backpacking stoves. I went to the
stream feeding the lake to fill collapsible bottles with water.
Don and I worked well as a team. We had dehydrated food
packages and some items to make the food go farther and
add taste. We made backrests out of sticks like American
Indians made. Three legged tripod with sticks bound
together and hung over the tripod. We ate our fill because
the hike had worked up a good apatite.
When nature called we went off into the rocks far
enough to do our business so that our waist would not leach
into the lake. We were enjoying each other's company, but
Don finally said, "Jacob I have something to confess to you,
and I hope we can remain friends after I tell you."
I wondered what he could tell me that might affect our
friendship.
Don said, "I am a hermorphadite!"
I was so niece I didn't know what he was talking about.
For all I knew he was talking about an ethnic group.
He knew that I didn't understand what he was talking
about. "When I was born they listed my sex as female
because I had a vagina, and my parents named me Donna.
When I reach puberty everything changed. I changed into a
boy. I was picked on by bullies until I got into weightlifting
and martial-arts. Now everything about me in male except
for my sex organ, I don't have a penis. I have a vagina and
clitoris like a woman!"
I still didn't completely understand what he was talking
about.
Don asked, "Do you want to see?"
I was puzzled, but curious, "Sure."
Don leaned forward to pull his T-shirt over his head. I
had seen is arms and before, but now I saw the designs on his
chest and lower abdomen.
There were swirling line circling his man tits and there
was something like a crest or coat-of-arms on his ripped belly
disappearing into his hiking shorts. His back was covered in a
colorful dragon with wings spread from shoulder to shoulder.
I was mesmerized by the tattoos on his body.
The next thing he removed his boots and sock before
standing up to remove his hiking shorts and underwear. As
the underwear came down I saw the bottom of that coat-of-
arms just above his pubic hair. When he stepped out of
shorts and underwear he spread his muscular legs so that I
could see what his crotch looked like.
I was speechless there was no penis or scrotum. I
couldn't believe that he had been born that way. They must
have been cut off.
Don placed his first two fingers on either side of the
mound and pressed when it opened I saw the ridge ending in
a clitoris like a little dick, and there were another set of flabby
lips and I saw the pink opening of my first vagina along with
the opening of his urethra. He used his index finger to
stimulate the clit kind 'a like I do when I masturbate. He told
me that I could touch it if I wanted to.
I had seen pictures of naked women before, so I knew
what a pussy looked like, and his pussy looked just like the
ones in pictures. I reached out and touched the warm slimy
flesh. That ridge leading to the clit felt like stiff rubber
covered with a layer of moist slippery skin. His clit seemed to
get harder and even larger. It actually stuck out like a penis.
Don said, "Would you like to fuck me?"
"I have never fucked anyone before."
Don's face light up "You're a virgin, I have never taken
someone's cherry before!"
The idea of getting to fuck someone gave me a hard-on
right away. Don saw the bulge in my hiking shorts, and he
smiled as he reached out and stroked the front of my shorts.
I was immobile, so Dom started removing my shorts.
At least I managed to pull my own T-shirt off while Don
pulled my shorts and underwear down. I stepped out of
them with my boots and socks still on. Other than that we
were both naked. We lay on his sleeping bag.
I had no idea how to go about this, so Don started
hugging and kissing me. It was strange kissing a guy with a
mustache and goatee, particularly when he started sticking
his tongue into my mouth. While we were kissing he ran his
hand down my body and started masturbating me like I had
always done. It was so much more exciting having someone
else masturbating me. It was the same thing that my parents
had punished me for doing was so wickedly sexy and wrong
at the same time. I had a ragging boner. It felt like it was
hard enough that someone could hang from it. It felt so
much better than it did when I masturbated myself.
Don moved down my body and took my cock into his
mouth and sucked on me. If anything my cock got even
harder. The strange thing was that as much as I was enjoying
the blowjob I couldn't cum.
After Don had sucked me long enough to make his
throat raw he lifted his head and announced, "I'm going to
fuck myself on your cock the first time Jacob!"
He stood up and straddled my hips facing me. When
he squatted down he reached between his legs to take hold
of my dick and guide it to his cunt. He settled down on me
until his flesh was pressing against my pubic bone. Then he
started lifting his body up and down. He was actually fucking
himself on my dick.
I still couldn't cum, until Don pinched my nipples and
twisted them in opposite directions. At that moment I felt
like my cock exploded. I was no longer a virgin.
Don managed to maneuver his body around without
my cock pulling out of his cunt so that he was lying on top of
me, and started kissing me again. When he realized that my
cock was not going soft he rolled us over so that I was on top.
I didn't have to be told how to pump my hips up and
down. I fucked him for what seemed like a long time. By the
time I had my second orgasm we were watching each other
by moonlight. We didn't want it to end so we put his bag on
top of mine and we got into his bag together after I removed
my boots and socks.
We had the lake to ourselves all weekend. We took full
advantage of it. Don sucked me off several times, and I
sucked his pussy and tongued my cum out of his cunt. He
even rolled me over and licked and stuck his tongue into my
asshole. That even made my cock hard right after cumming
in his mouth. That evening Don had me fuck him in the
asshole as well as his pussy. I even tongue fucked his asshole
after I shot my load in his ass.
We spent so much time fucking that we had a ravenous
appetite. When we weren't fucking we were eating. It was a
good thing we brought more food than me needed because
we ate a week's ration of food in two days.
When we packed up to come out, I was so tired that I
felt like my knees were going to buckle at any moment. Don
invited me to move into his apartment. I was one happy boy.
I was getting sucked nightly and had my chose of pussy or ass
to fuck as well.
Anyone seeing Donald would never suspect that he
was anything more than one hell of a good looking man with
the body as good as any Mr. Universe. To prevent anyone
noticing the lack of a bulge in his pants he wore a jock strap
filled with a rolled of a pair of socks.
We did get teased about being gay, but I didn't care.
After school I eventually moved on, but never found
another guy like Donald.
If you enjoyed the story and have a story you want me to
write about your introduction to the world of male sexuality,
please send your outline to pomowolf74@yahoo.com