My first time with a boy.
{A true story}
must be 18 and over to read this story.
This is my story.
Well I was 12 at the time I had my first encounter with another boy my age. My name is Jackson, He was my best friend; his name is Conner
and has dark brown hair and a firm body, 5 foot 1 inch, he’s 12 as well. I have blonde hair and blue eyes and just have a little baby fat
left on me. I’m 5 foot 2 inches. We are both circumcised and have a purple scar around our shafts. We had the same doctor
circumcise us as our parents were friends and saw that we would get the same circumcision operation. High and tight.
Any way one day we were at the swimming pool and chilled out there for a few hours and enjoyed ourselves with other
boy’s from our school. It was summer time so we could hang out all day as our parents worked long hours and they
let us do anything we wanted as long as we phoned them from time to time. Any way we had just entered the locker room
to take a shower before heading back home. We have seen each other naked and knew what we had down there but
today we saw a boy with a strange looking penis.
“Hey Conner look at that boy’s wiener he’s got skin covering the end of his penis.” I quoted. “It’s called a foreskin Jackson,
we all had one but ours was cut off when we were babies.” Conner explained. “Oh I see, I wonder why he didn’t get his
chopped off.” I replied. “I don’t know but all the boys in our gym class have a circumcised penis like ours so maybe
his parents didn’t want his foreskin cut off.” Conner grinned.
We continued to wash off the chlorine and used the soap to make us smell a little better. The 11 year old boy was
showering next to us and our eyes popped out when the boy pulled his foreskin back exposing his purple bell end
and washed it with some soap. I popped a wood and so did Conner… That has never happened to me before, getting
a boner watching another boy wash himself but today seeing this boy do things to his penis was so exciting that I
had to turn around and quickly feel my wiener and rub it for a while.
Conner and I didn’t experiment sexually at first, yes we touched each other’s wieners like show me yours and I’ll show you mine
thing but never jacked off until today. Jackson you got a wood dude.” Conner giggled. “You have one too.” I said.
“Does this happen to you all the time.” I asked my best friend. “Yeah and it bones up when I at least expect it.”
Conner laughed. The other boy left us and walked out of the locker room leaving us alone in the shower room.
“Um Conner do you want to sleep over night with me tonight.” I asked.
“Sure bro, you know I like coming over to your house.” Conner smiled. “Ok but tonight I want to try some stuff
and I don’t know if you want to do it with me.” I gasped. “What kind of stuff Jackson.” Conner asked. “Well
my older brother told me about masturbating and what comes out of our wieners when we play with them.”
I quoted. Our sex Ed class would be starting when we returned to school and we didn’t get the birds and
the bees talk from our parents so we didn’t know about jerking off and other things like that until my
older brother decided that his younger brother should learn all about our wieners and how to play
with them.
“Masturbating, I heard about that at scouts but no one would tell us about this masturbating thing.”
Conner moaned. “Ok so tonight I want to show you what my brother showed me as it is fun to jerk off
and you get this tickle feeling coming out of your dick and when I first did it I saw this clear goo
come out of my pee hole.” I replied. Conner’s eyes lit up and he had a boner sticking out that it
bobbed up and down with each heartbeat.
“Ok Jackson but we better not get caught or I will never forgive you.” Conner gulped. That night
we returned to my room as our parents were going out and my brother would be in his room
with his friend that night. He’s 15 and would be sitting for us but I knew he would be smoking
and watching porn with his pal. He never came into my room unless he knocked first so I
knew he would not disturb us while we had our sex play that night.
We played on the X-box for an hour before Conner got restless. “Um Jackson are we going to
do what you asked at the pool.” Conner said. “Um sure if you want to.” I remarked. ‘Ok then
what do we do first.” he asked me. “Get undressed and lie on the bed and wait for me as I need
to get something out of my secret box.’ I giggled. Conner was naked lying on my bed with a boner
sticking straight out. I was boned up too and could not wait to jerk off with my best friend.
“Conner my brother said to use this stuff as it makes our wieners slippery when we play with our
wieners so cover it all over your dick.” I giggled. I grabbed a towel and placed it on my bed and
then used the lube and made sure that I had covered my dick with this slippery stuff.
“Now what Jackson.” Conner asked. “Close your fingers around your wiener like this and then move your
hand down and up until you cum.” I said. “Cum, you mean the sticky stuff.” Conner grinned.
I started to stroke my shaft as my brother showed me and watched Conner stroking his shaft.
“Wow this feels awesome dude, your wiener looks so hard now.” Conner quoted. “It is but
wait till you cum and then see how hard it gets.” I replied. We continued to jerk off and our
speed got faster and faster. ‘Let me do it for you Conner, you will feel even better if I did it
to you.” I said. “Um is this gay to jerk each other off.” Conner questioned. “No way dude,
my brother has done this with all his friends and they all have girlfriends now.” I remarked.
Conner stopped stroking his wiener and let me continue to give him relief. His body jumped
when I touched his cut cock for the first time and soon was cooing as I stroked his tool.
“Oh god this sure does feel strange, no one but myself has touched my wiener except
for the doctor but he was not stroking it like you are.” Conner panted. I quickened my
pace and moved my slick fingers up and down over my best friend’s cock until he started to jerk
his butt up and down until he told me he was going to pee.
“Stop Jackson or I will pee on the bed.” Conner moaned. “You won’t Conner, you will get the
tickle feeling and then squirt your goo.” I mumbled. Faster and faster I stroked his wiener until
Conner yelled that his cock was on fire and let loose a small squirt of cum out of his wiener.
“Oh fuck what was that.” Conner gasped squirming on the bed. ‘You cummed dude, you
had what my brother calls an orgasm.” I grinned.
Conner looked at his red throbbing cock and saw a bead of cum leave his pee hole. “Look my
wiener leaked some shit out of it.” Conner panted. “Yeah wait till you really start squirting stuff
like my brother does as it shoots over his head.” I laughed. Conner was now relaxed and saw that
my wiener was stiff and waiting for relief. “Um do you want me to jerk you off now?” He asked me.
I nodded my head and laid down on the bed, my butt was on top of the towel so that we didn’t
make a mess on the bed spread.
“Get ready Jackson.” He told me and started to lube my wiener. It felt cold at first but when Conner
started to jerk his fingers down and up on my shaft I started to moan as the heat of his fingers
covered my shaft. ‘That’s it Conner, go faster dude, make me cum, oh shit this feels awesome.”
I groaned as I started to fuck his hand feeling my shaft slide in and out of his lubed fingers.
Conner was watching me twist and turn as I got closer to Cumming; he had a smile on his face
knowing what was going to happen to me.
“This is weird but it feels great to feel another boy’s dick.’ Conner moaned as his fingers continued
to stroke my saddle shaped glans. My scar was turning a little red where my foreskin used to be as
Conner continued to jerk me off. My butt was rocking up and down until I felt my small balls tighten
until I let out a gasp of air when my pee slit opened and squirted a small amount of cum over
Conner’s fingers.
“Gee you squirted a lot more than me.’ Conner groaned. “Well I’m 4 months older than you but you
will be squirting lots more when you get older.” I explained to him. We went to my bathroom and cleaned
up all our mess and then returned to my bed. “That was the best thing I have ever done with my wiener
Jackson. Do you know any more stuff we can do together.” he asked me. “Yes but you have to promise
not to say a word to my brother or anyone else for that matter.” I muttered.
Conner nodded his head and in seconds he had another boner sticking out from between his legs.
“Um you know when we watched that boy wash himself at the swimming pool I got a feeling down
my dick that I never felt before, now I want that feeling again.” Conner gulped. “Ok take a look at
this.” I said pointing to a stick book filled with naked men and women that was given to me by my brother.
We flipped over the pages and Conner’s eyes lit up seeing his first look at a woman’s virgina.
Then we found pictures of men fucking and sucking each other’s dicks. ‘Is that for real?” Conner
mumbled as he slowly stroked his boyhood. “Yeah my brother said he has done this with Ryan
last year and told me it hurts a little bit but he told me to use this stuff to make it slippery to
shove your dick up a boy’s hole.” I replied. Conner’s eyes shut tight for a few seconds and then
opened them before he asked if I wanted to do what those men were doing to each other.
‘If you want to Conner, I have never done it before, just heard what my brother did to his friends.”
I quoted. “Ok then let’s do it before I chicken out.” Conner replied. I grabbed the lube and started to
finger his butt hole like my brother Wesley told me and soon I had two fingers up my best friends butt hole.
Conner was moaning and groaning as I entered his hole and said he feels like he wants to take a dump.
‘You’re doing fine Conner, do you want me to try using my wiener now.” I moaned. Conner whimpered
for a second and then nodded his head. I moved a pillow under his groin and slowly aimed my circumcised
head towards his hole. I had lubed my cock and it was throbbing as I slowly pushed into Conner’s butt hole.
“When I say push your butt hole like you are about to take a dump and then I will be able to enter you.”
I said. Conner let out a grunt as I passed his sphincter rings and waited until Conner relaxed his butt muscles.
‘I in Conner, how does it feel.” I asked him. “Oh shit it hurts but it also feels like I need to shit at the same time
it feels awesome.” Conner mumbled. I waited for Conner to settle down and then I started to thrust my shaft
in and out of his lubed up hole. “Oh fuck that feels great Jackson, move faster dude, fuck me, oh shit I
feel your cock rubbing inside me.” he gasped as I hit what was his prostate and give a grunt as it rubbed
my wiener over his button again and again.
“Holy fuck my wiener is so hard I need to jerk it off.” Conner groaned as he flicked his tongue out like a snake.
“OH god you’re tight Conner, you have to try this after I have finished fucking you.” I quoted. I had never swore
that bad before until I started hearing my brother swearing when he was fucking or getting fucked. I didn’t
know what he and his friend were doing as he only did this fucking thing when our parents were not in the house.
Now I knew how he was feeling when I started to pound my friends butt.
Slapping his butt with my balls as I rabbit fucked Conner’s hole soon put me over the edge and I gave Conner one
last jab before I cummed into his moist bottom. “I’m Cumming Conner, take my seed and join our bodies together.’
I yelled as I fell on top of my best friends back. Sweat was falling off our bodies as we lay on the bed panting
and sucking in air as my orgasm settled down.
“Jackson, if you had d asked me to do this with you earlier on I would have caved your head in and would have
told you to fuck off but now I am glowing like a bright light and it was an awesome feeling I truly enjoyed.’
Conner said surprising me with a kiss. I gave Conner the lube and he in turn lubed my hole after waiting
to get his sexual feelings back so that he could do me.
I felt his fingers enter my hole and soon found my butt hole open up to his fingering. I let out a gasp of air
as he hit my prostate, I didn’t know what he hit but my wiener boned up in a flash as he rubbed my young button.”
Whatever you did just then don’t hit just yet or I will squirt myself.” I groaned. Conner had three fingers up my butt
and I told him to enter me. I felt his hot circumcised head push into my sphincter and slowly enter my deep tunnel.
‘Are you alright Jackson.’ he asked me. I just nodded my head as he continued to drill me.
“Go for it Conner, fuck me, fuck me hard.’ I yelled out. I hope my brother could not hear us as we fucked one
another, I bet he didn’t care as he would be doing the same thing to his pal. Conner started slow and then
he started to rabbit fuck me pounding my hole with all the energy he could muster. He was now drilling
that little button inside my tunnel and soon I was gasping for air as he squirted into me. My memory
is fading so I needed to write this down and send it to Conner who is now living on the other side of the
world and I hope he too remembers the fun we first had together as cum buddies.
Love
Jackson.