Date: Sat, 9 Mar 2024 13:07:19 -0500 (EST)
From: ShortStories@PlayTime69.e4ward.com
Subject: Jimmy Gives It a Try

	This story is 100% fiction and is for mature readers only. If you
are under 18 please leave now. Please note that all my stories are written
for enjoyment only and not intended to give anyone ideas on what to do,
what to try, or who to do things with. The actions taken in my stories
should stay in your mind only and not expanded to real life situations.

	This story is a fantasy involving a man and a preteen boy. You can
see a list of all my stories on the authors page under the author,
Playtime69. All comments are appreciated and can be emailed to
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	This story's general idea and information came from one of my
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here. I hope you enjoy this story about how a man and a preteen boy enjoy
each other's body while the boy's mother and man's wife watch from afar.


                    Jimmy Gives It a Try

                       by: Playtime69


	As soon as I had got home from a long day at work I jumped in the
shower. I then dressed in a thin blue tee shirt, short jean cutoffs, and no
underwear. My flaccid cock snuggly trapped between my skin and the front of
the jeans. Once dressed I made my way to the kitchen where I found my wife
and her best friend having a conversation. The problem was as soon as I
walked in their conversation stopped.

	Magdalene was my wife and her friend's name was Hayden. Hayden was
divorced and lived alone with her 12 year old son, Jimmy. My wife was a
very attractive 24 year old blonde with blue eyes. Hayden was older being
32 years old with long dark brown hair and brown eyes. Her son, Jimmy, was
a spitting image of his mother. He too had fairly long dark brown hair and
unusually seductive brown eyes. By looks, he could have been a cute girl
but was always dressed as a boy and more or less acted the same way.

	Hayden and Jimmy lived a couple houses down and since Hayden and my
wife were good friends she was normally at our house unless she was at work
or Jimmy was home from school. When Jimmy was not in school or at a
friend's house Hayden normally was at home with him but when they were
wanting to do something they came to our house. We were all friends and got
along great. I would help Jimmy from time to time with school work or by
helping out with problems he had from time to time.

	I could feel the girl's eyes following me as I walked across the
room to the refrigerator to get a cold drink. I filled my glass and turned
to see if they needed something. Our eyes met but they still were quiet.

	"You girls seemed to be in deep conversation. Everything alright?"
I asked.

	My wife looked at Hayden, smiled, and said "Well should we ask
him?"

	Hayden looked around the room and finally said "Yeah, I guess we
could."

	This conversation peaked my interest so I asked, "Well, what's up?"

	"I'll let Hayden tell you." My wife said with an unusually
seductive smile.

	This cat and mouse game was beginning to make me wonder if these
two women were plotting something. I looked down and found my cock still
covered. I could not think of anything about myself that was out of the
ordinary. Thinking back I had noticed these two had been dressed in sexier
clothing lately but figured it was just my imagination. Could it be...

	It was about then in my thought process that Hayden began to fill
me in with what I was being left out about. "You know my son, Jimmy."

	"Yeah." I said as I nodded my head thinking that was a really
stupid question.

	Taking a deep breath, Hayden quickly blurted out, "I am pretty sure
that he is gay." She then quickly added, "Well he might be bisexual but I
am pretty sure he is more interested in cock than pussy."

	I was surprised to the point I wanted to know why she thought that
her son liked guys more than girls. I looked at my wife with a stunned look
but turned back to Hayden to ask her why she thought such a thing. I was
even more surprised when I heard her answer.

	"Well, with no man in the house and it being just the two of us we
are quite open about things. I tell him things and he tells me things that
neither of us have told others. Last night Jimmy told me that he wants to
have sex with a man and that he was having really strong urges about it."
Hayden explained.

	I looked at my wife then I looked at her friend. I then looked back
at my wife before asking, "Well that is not the typical thing for a boy to
tell his mother. So...What do you want me to do about it? Talk to him?"

	They both looked at me with a strange look like I should be able to
know without them telling me. Hayden looked at my wife and my wife looked
at me and let out a loud sigh.

	She then looked at her friend and said, "Bob does not get it. I
guess you will just have to come out and ask him."

	"Ask me what?" I quickly asked.

	"Talking to him is not going to do any good. I have already got all
the information out of my son that he is willing to share. I know he has
not done anything with a boy or a girl. I know he does not seem to even
want to do anything with girls. I also know he is afraid to talk to his
friends about it because he is afraid of what they will say. This only
leaves me to find someone he can...well you know...with." Hayden pleaded.

	I got this blank look on my face when I realized what they wanted
me to do with this small 12 year old boy. The problem was when the
realization of having sex with a boy, especially a really cute 12 year old
boy, came across my mind my dick began to inflate in my already tight
shorts. This quickly became noticeable as I stood in front of these two
women with the front of my body unhidden. I stood thinking about it and the
more I thought the harder I got to the point both women could not help but
see my erection.

	When I was in college I had a few bisexual experiences and had
actually enjoyed them. I also enjoyed fucking lots of girls as I grew up so
was quite versed in sexual activities of both sexes. The more I fucked the
more I leaned towards women to the point I got married to one. I had never
had sex with or even messed around with a 12 year old boy before so was a
bit on the hesitant side. Knowing that his own mother was the one that
asked me to help out in this situation was a great relief and also a big
inspiration to me agreeing to help. I am not sure who was more grateful my
wife or her best friend. They both thanked me and each gave me a
hug. Before I could get the specifics of when, how, etc. I was blindsided
with something Hayden said.

	"Bob. We do have one condition." Hayden stated.

	"What's that?" I questioned.

	"Magdalene and I have to be there to see what goes on." Hayden told
me.

	"Sounds like fun to me but not sure how Jimmy will react to having
his mother watch the first time we have a sexual encounter." I
suggested. "I know if it were me I would not want my mother in the same
room as I was when I was having sex with another guy." I added.

	There was a lengthy pause as we all tried to figure out a solution
to my last comment. It was during this pause my wife had an additional
concern.

	"Hayden, have you seen my husband's erect dick?" My wife openly
asked her friend.

	I had not really thought of that issue and was a bit uncomfortable
with my wife bringing up the size of my manhood. I was also wondering if
she was fishing for some possible playing around between myself and her
friend. At least if that were the case I knew I was safe as we had never
done anything and other than a few minutes prior when I was hard standing
right in front of them, I knew she had not seen me hard before. I just
stood waiting for her to answer the question.

	"No. Why?" Hayden wondered.

	"Well let's just say he is not small. Maybe he needs to let you see
it before you talk to your son." My wife surprised me by telling her
friend.

	Just the thought of a woman other than my wife seeing my dick was
causing an instant erection. I was proud of what I had and did not mind
showing it off, especially if it was my wife's idea. I just stood there
waiting to be told what to do. There was no way I was going to drop my
shorts in front of my wife's best friend without her telling me to.

	Luckily I did not have to wait long because Hayden replied, "Ok,
let's see it."

	I turned and looked at my wife for her "Ok" before I dared to drop
my shorts.

	"Go ahead, big boy, show this nice lady what you have hidden under
your shorts." My wife teased.

	Being an obedient husband, I unbuttoned my shorts before pulling
the zipper down. I could feel my dick getting bigger and harder with each
tug on the zipper. I then began to wiggle my way out of them until they
fell to the. I briefly brushed over my cock and balls to 'fluff' them up as
it continued to grow. A few seconds later it was standing straight out as
it looked right at Hayden's open mouth. She was having a hard time
believing that I had this massive 8" not so thin piece of meat stuffed in
the little shorts. I could see in her eyes she wanted more than to look but
that was not an option. I was faithful to my wife and unless she instructed
me to fuck her friend I was just going to stand there and let them look at
my nearly naked body.

	"Ok. You are right. I do not think Bob's cock will fit up my son's
ass." She disappointedly said. Then after a pause she added, "What if you
shove it down his throat and then let him fuck you in the ass."

	Not waiting for my wife to agree I quickly answered, "That would be
fine with me. I can also fuck him between his legs. Better yet I can let
him be on top of me with my dick between his legs and he can dry hump
me. He might just cum too."

	By now my dick was dripping pre-cum on the floor and I could tell
my wife was getting wet. I am not sure but I think with my last comments
Hayden might have had her own orgasm as she thought of her son fucking my
cock. We continued to talk about the details but instead of letting my
pre-cum go to waste I scooped it up with my fingers and shoved them into my
mouth. What I was doing did not seem to bother either of the women so I
continued to pull on my shaft to drain it of its liquid gold.

	A few minutes later the plans had been made and Hayden was about to
leave when I brought up the issue with them watching. Eventually it was
decided that if he did not want them in the same room, I would set up a
camera so they would watch from the other room which in the end was
actually what took place as Jimmy did not mind them watching but he did not
want them in the same room while it was going on.

	The worst part of this whole set up was that it would not take
place for a little over a week from the decision. I had been told I could
not cum again until it was with Jimmy. This was going to be hard to do but
I figured it would be worth it.

	Hayden spoke to Jimmy later that night and he loved the idea,
especially knowing his asshole was safe from being filled with my big man
meat. We had discussed me fucking him with my wife's strap-on which was a
lot smaller than my cock. He said he would give it a try if I would stop if
it hurt too much.

	The night finally came and I set up the bedroom with everything
that was needed to give Jimmy his first gay experience. I also set up the
camera so his mother and my wife could watch from the other room. I took a
long hot shower and made sure I shaved my dick and balls nice and close. I
slipped on a pair of sexy underwear and waited for my boy toy to show
up. Jimmy also was to take a nice long hot shower and since he was still
naturally hairless he did not need to shave. He dressed to walk to our
house but once inside he stripped with the exception of a cute pair of boy
underwear that was pushed out in the front by his already growing 4.5"
cock.

	"Hi Jimmy. Are you ready for some fun tonight?" I asked as I took
him by his small boyish hand.

	"I think so." He quietly answered.

	We made it to the room where I was going to fuck his ass with a
strap-on and where he was going to fuck me in the ass with his little boy
dong. I closed the door once we were both inside and then led him to the
bed but before I let him lay down I pulled his underwear down freeing his
super hard dick. It was quite thin but looked really tasty. I then had him
finish undressing me allowing him to see my massive dick for the first
time. He stood amazed at its size for a bit before he reached out to touch
it. I let him do what he wanted as we slowly laid down in the bed.

	As he rubbed his small soft hands over my dick and balls I began to
play with his naturally hairless genitals. We both moaned until I leaned
over and gave him a loving kiss on the lips. This was like lighting
gasoline with a match. He instantly pushed his face into mine as his tongue
exited his mouth and forced its way into mine. Not that I minded in the
least. It was just not what I had expected. Soon I took one hand and
wrapped it around his small thin frame as we had one of the hottest French
kisses that I had ever had.

	It was not long before he took his hands off my baggage and put
them around my body as he held me tight. From time to time he rubbed over
by tight bare ass making me feel like he was ready to fuck and be fucked. I
could feel his small pecker oozing pre-cum and knew he was enjoying our
time together. I pulled my hand from his privates and grabbed hold of his
tender young butt cheeks. Pulling him into me, he began to move side to
side, in and out, and up and down as he tried to get as much pleasure as
possible.

	Before it was too late and he blew his first load of the night, I
pulled back from our kiss and moved my lips to the side of his face. I
gently blew in his ear and nibbled at his neck. He let out a calming moan
as goose pimples sprang up all over his upper body. Moving around I
lovingly kissed his neck, chest, and each nipple. As I paid his nipples
special attention he grabbed hold of the back of my head and pulled me into
him. I licked, sucked, and gently bit each one until he began to have an
internal orgasm from such an exciting ordeal.

	Moving down his hairless body I kissed his sexy belly button that
was still small and reminded me of a very young boy's anatomy. I continued
my path and kissed the base of his blood engorged penis. He began to purr
as I worked my way up the shaft.

	"Mmmm...Ohhh...Yesss..." Jimmy moaned as I worked my way to the
head of his dick.

	I crested his male member and gently kissed the tip sending him
into a tailspin of excitement. I could taste the preteen's pre-cum as I
lovingly licked his tiny pee hole. I took his small but exciting penis into
my mouth and sucked on it like it was a straw. My nose buried into his
flesh where his pubic hair would have been is he was older. I could smell
the scent of young virgin boy skin as I continued to suck, causing his
heart to pound and his breathing to increase. I am not sure who was getting
more enjoyment out of this but what I did know was if I did not stop
neither one of us was going to be able to hold back from an explosive
orgasm.

	 I opened my mouth and left his dick bouncing in the cool
air. Jimmy whimpered like a puppy wanting his belly rubbed. It was not that
I did not want to continue and it was not that I did not want him to cum,
it was because I too wanted to feel his soft young lips wrapped around my
older much larger cock.

	I sprang up onto my knees and spun around so fast that Jimmy had no
idea that I had moved. Before he knew it my pre-cum dripping cock was right
over his mouth and my mouth was hovering over his fresh young dick. I
lowered my body down to see what he would do as my dick approached his
mouth. He did just what I had hoped for. He grabbed hold of my shaft,
opened his mouth, and tugged on my dick releasing a stream of man
pre-cum. Aiming just right he drank my pre-cum and went back for some
more. Once he found I had no more pre-cum he pulled my dick into his
mouth. I could feel his young tender warm lips as they wrapped around the
head of my cock. As soon as the head was inside his mouth he began to suck
me like I had done to him.

	Not wanting to leave him hanging, I quickly sank his cock into my
mouth and began to suck him like he was sucking me. My nose rubbing his
small hairless balls as I sucked on his thin but tasty male member. After a
few minutes of pleasuring this young boy I could feel his dick begin to
swell and that along with his harder breathing and quicker heart beat I
knew he was nearing a super hard orgasm. I could not punish this young lad
anymore and just had to give into his need to cum. I took his entire length
into my mouth as my nose was pushed as hard into his ball sack as
possible. I sucked as hard as I could drawing the head of his cock into my
throat. I caressed his shaft with my tongue as I began to moan causing a
vibration to his dick head.

	Jimmy could take no more and released my dick so he could pay more
attention to his own pleasure. This was alright with me as I wanted him
have the best orgasm possible. I would later find out that this was his
first orgasm and that he had not even jacked off before which made this
extra special. Jimmy began to thrash around like a fish out of water. I
knew this was a sure sign of a hard orgasm about to take place. I held him
tight as I continued to pleasure this young boy. When he figured out he
could not get away from my tight grasp he calmed down a bit and enjoyed the
pleasure I was giving him. It was then I began to pump up and down on his
cock like I was fucking him with my mouth all while sucking and teasing his
shaft with my tongue.

	"Ohhh...Ohhh...Ohhh...Mmmm...Mmmmmm...Yesss..." He howled as I felt
the first ever squirt of cum escape his young penis.

	It was a small but forceful squirt that hit the back of my
throat. It was followed by two more smaller not so hard squirts then some
dribbles as he went over the top with a massively hard orgasm. Soon after
his orgasm had ended, he frantically tried pulling back from me. Thinking
back to my first time I remember how sensitive my dick was after that first
load was released and knew that by me continuing to suck and tease his cock
that it was probably getting painful. I let his dying dick flop from my
hungry lips allowing him to catch his breath.

	Still not saying a word I knew it was now my turn to be rewarded. I
again lowered my once again pre-cum covered dick head to his lips. This
time he was more hesitant to take it into his mouth but he did. Once it was
inside his young warm lips he was right back at it. He sucked and stroked
and prodded at my balls. I too began to breath heavily as my dick swelled
in preparation of a huge orgasm.

	"I am about to cum, Jimmy. Just relax and let it flow down your
throat. Take what you can and let the rest splash on your face. You are
doing great, Son." I encouraged him as I began my mental countdown to
blastoff.

	He took my cock as far into his young mouth as he could and began
to suck. He was a fast learner and was doing to me what I had done to
him. A minute later I exploded sending a week's worth of cum into this
little boy's mouth. He took about seventy-five percent of my load and then
let the rest land on his face. He rubbed my dick in my own cum as he
smeared it around his mouth and lips. When he had recovered from the big
blasts he opened his mouth and sucked my shaft and balls dry.

	When I had recovered I moved back up and licked my cum from his
face before kissing him once again with my tongue. We returned to our hot
French kiss as we hugged and caressed each other's body. We took a short
nap as we rested to regain some strength.

	Once we were both awake and ready to go again I asked, "How would
you like to give it a try and fuck me in the ass?"

	"Really? Can I?" He questioned.

	"Sure." I confirmed.

	I grabbed the lube and showed him how to lube up an asshole. Then I
put some on his once again hard cock and laid down on the bed face up. I
helped him get between my legs as I raised them over his shoulders. I
figured this first time I would need to see and help him get it in just
right. Later I would let him fuck me doggie style if he wanted but for now
I wanted to teach him some basics. I stuck a pillow under my ass and guided
him into my hole. Even though I had not been fucked in my ass in years he
still entered pretty easily. This was probably because he was so small.

	I had forgot how much I enjoyed being fucked in the ass by a real
cock. It was just the right size and shape to cause me exceptional
pleasure. I was sure he too was enjoying the tight fit of my ass around his
cock. I taught him how to pump his dick in and out of my ass and once he
had all the information needed I let him at it. At first he was a bit
awkward but given some time he managed to fuck me like a pro. He only
lasted about five minutes before I felt him quirt a load of cum into my
body. When he had finished he collapsed onto my chest where I held him like
a baby, his cock still inside my body.

	We laid together for some time before he raised up and asked if I
was going to fuck him in the ass with my big dick. I explained that I was
too big for him to handle but if he wanted me to fuck him so he would know
what it felt like then I could use my wife's strap-on. I told him that it
was a little longer than his dick but maybe not as thick. I told him I
thought it would fit but if it hurt too much then to let me know and I
would stop. He agreed and in a flash I had his asshole lubed up and once I
put the harness on with the dildo I also lubed it up. He got into position
where I slipped two pillows under his butt to raise him up.

	I slowly spread his legs as far as possible, lined up the dildo to
his hole, and lowered myself until I made contact. I slowly worked my fake
dick in and out of his slippery hole. He moaned from the pain from time to
time but never told me to stop. It was not long before I had the fake balls
pressed against his butt and he was begging me to fuck him.

	"That feels good...It filled my ass up. Oh yes..." He moaned as I
tested to see where and how he liked to be fucked the best.

	I sped up some while he held his ground and did not try to get away
from my strap-on pounding in and out of his ass. I was at just the right
angle that I rubbed back and forth against his prostate while I fucked
him. I watched as his cock began to grow to it full size once again. While
fucking his ass I reached down and began to stroke his hard dick.

	"Harder...Fuck me harder..." Jimmy begged.

	I did not want to hurt the boy but then again I wanted to give him
all the fun and excitement that he could stand. I continued to pound his
ass while stoking his preteen dick. My own super hard cock was rubbing
between his legs and from time to time I held his cock to where my rubbed
next to his as I pounded his ass with the dildo. I hit just the right place
and knew I was not going to be able to stop. I moved my hand, lowered my
body and paid more attention to fucking his dick with mine more than
fucking his ass with the dildo. Fucking his dick with mine also caused my
dido to fuck his ass at the same time.

	"Mmmm...Yesss...Pound my ass...Rub my dick...I...I...I am going to
cum..." Jimmy moaned.

	He was right and before I could stop him he squirted another load
all over my dick. This natural lube added pleasure to my own male member
and like it or not I could not stop and kept pounding his ass and rubbing
my dick on his until I too blasted a load all over his smooth belly,
hairless dick and hairless balls.

	I slowly pulled the dildo from his ass causing him to moan from a
feeling of emptiness. I knew that feeling well when I was in college. Each
time a dick was removed from my hole I was left with this feeling that I
was left empty, even if I had been filled with cum.

	I removed that harness and snuggled up close to Jimmy. Our cum
coated bodies now together as one. I kissed him on the cheek as he nuzzled
close to my chest. We again drifted off to a restful sleep. This time we
stayed this way the rest of the night.

	The next morning we woke to the smell of breakfast being
cooked. Not too much later the door opened and Hayden and my wife entered
the room. They were serving us breakfast in bed. When asked why we were
getting such treatment they said it was because of the fantastic sex show
we had put on the night before. This embarrassed Jimmy a bit but I found it
energizing. We ate our meal and once the women were gone with the door
closed I asked Jimmy if he wanted to cum again. He was more than willing.

	We discussed the possible ways to fuck and decided that he would
get on top of me. His dick and mine lined up side by side and after lube
being added he fucked me while not being in my ass. That turned me on to
the point that we both were supper hard almost instantly.

	Jimmy got on top and soon was fucking me with his hard wet hairless
dick. He rubbed my cock with his at just the right place. He humped me fast
and slow all while we were once again into a hot French kiss. I humped him
back and soon we spewed another load of cum on each other. We continued
until the cum was smeared all over our bodies.

	We eventually got up and showered together before slipping on our
underwear and going out to eat lunch with the girls. During lunch we all
discussed what had happened. Jimmy finally felt more comfortable talking
about gay sex and how he very much enjoyed what had taken place. He like I
wanted to do it more often but the girls were not so sure. It was
definitely a topic that would have to be taken up in the future. For now we
not only had the memories but the girls had recorded the entire show
putting it all on a disk for future excitement.

                              The End