Date: Thu, 13 Oct 2016 02:37:40 +0000 (UTC)
From: ShortStories@PlayTime69.e4ward.com
Subject: Babysitting Job - Chapter 1 - (b/B, Bb, 1st, oral, anal, mast, ped)
(b/B, Bb, 1st, oral, anal, mast, ped)
This story is 100% fiction and is for mature readers only. It is a
fantasy involving sex acts of children. You can see a list of all my
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My First Babysitting Job
(Dave and I Become More Than Friends)
by: Playtime69
There are several things we remember as adults from our
childhood. One of those events is the first job. When I was 15 years old
there was a new employee where my mother worked. My mother became good
friends with the woman which had a young son. Her son's name was called
David but he went by the name Dave. Dave was 8 years old and a very cute
boy. His body was petite and had more of a feminine look than a masculine
look. Since his mother was not married he was growing up with only a woman
in the house so was brought up more as a girl than a boy. He did wear boy
clothes but that was the only way you could tell he was a boy. He had
fairly long light brown hair and a cute smile. He wore mostly light color
clothes like yellow, blue, and green unlike a boy wearing blue jeans.
My mother came to me not long after they had become friends and
asked me if I would be willing to watch her friend's son after school each
day so she could work later. My mother told me that I would get paid but
not as much as what I would be getting from someone else because she did
not have much money and was having problems being able to pay the rent and
buy food. I agreed and did not argue about the money as I felt sorry for
the woman. I really did not need the money anyway because I got whatever I
needed anyway. Things were set and I would walk over to their apartment
after school each day and would get there just as he got home from
school. I would then stay there until his mother got home and would walk
home. Good thing we did not live too far away.
Guess I need to add some information about myself. I am 15 years
old and my name is Mike. I have brown hair that is not long but not short
either. I was a typical teenager. I loved rock and roll, all sports, and of
course girls. It did not take much for my dick to stand at attention when I
saw a girl in a bikini. My dick was a respectful 7" long when I got hard
but was not too big around. It was not skinny like a pencil either. I was
about 5'6" and weighed 130 pounds with very good muscle tone. I did not
have a girlfriend but was not afraid to talk to them either. I was still a
virgin as I was not allowed to date until I turned 16. I had been jacking
off every day or two for the past two years and had no thoughts of
quitting.
The first few weeks were a lot of fun. I would get there right
before he got home and when he got home I would help him with his homework
then we would go outside and play ball. I taught him about baseball,
football, and some other sports. I would fix him a snack and we would end
up watching TV while snacking on chips, popcorn or other items I could
find. It was usually 2-3 hours before his mother got home and when she got
home I would leave.
Something came up at his mother's job that caused her to have to
work real late for a week. I am not sure what it was but I was just told
she would not be home until about nine at night. Dave was to be in bed at
eight so I was responsible to fix dinner and get him to take a bath and get
into bed all by his bedtime. It was not big deal as we had become good
friends and we were both guys so I did not even think there would be a
problem. It was only temporary so I was going to do my homework after he
got into bed. One good thing was my father would pick me up each night so I
did not have to walk home in the dark.
Monday came and I was at Dave's apartment just as normal. Dave got
home and I helped him with his homework. When we were done we went outside
and played catch a while and then back inside. I told him he was to take a
bath then we would eat and if time some TV but he had to be in bed by
8:00. He finally agreed and headed off to the bathroom. I ran the bath
water and he took off his clothes and got into the tub. I left him alone
and started dinner. When I got back to the bathroom I found him clean and
ready to get out. When he stood up I noticed he had a boner. His little
cock was sticking straight out from his small nut sack. His hard cock
looked to be a little over 3" and for an 8 year old that is pretty big. He
did not have a single hair on his body other than the top of his head. I
could not help but stare at his hard dick as he dried himself off.
"Mike. Mike!!" Dave yelled trying to get my attention.
"Huh? What? Oh. Sorry." I mumbled.
"What you staring at?" He then asked.
"I. Well. Ummm. I was just looking at your cute hard cock. I have
never been interested in guys before but your cock is so cute and without
hair it is really something I find interesting." I admitted.
Dave giggled then said, "Mom likes it too. She said I will make
some girl really happy when I grow up."
"Do you get hard in front of your mother?" I asked Dave.
He giggled again then answered, "It gets hard a lot especially when
I take a bath and when I get up in the morning."
"Can I touch it?" I begged not knowing what was drawing me to get
involved with another guy especially with one so young but I was somehow
attracted to him and his cock.
"I guess so. Never had anyone else touch me before." He answered.
I was amazed he was still hard after all the time we spent talking
and with him standing drying off. I reached down and put my hand around his
smooth hard little cock. He jumped just a little but quickly got use to my
hand as it wrapped around his shaft. I started stroking it like I did my
own cock when I masturbated. I was not sure what I expected but was
basically wanting to make him feel good. He moved around a little like he
was trying to get away. I asked him if he was ok and he let me know he was
it was just a funny feeling. He soon got use to me stroking him and was
soon pumping against my hands.
"Can I see your weewee?" Dave asked me.
"Sure. You can touch it too if you want." I replied as I dropped my
pants and underwear.
My dick started out semi erect but within seconds of my pants
hitting the floor and Dave's little fingers touching me I was hard as a
rock. He started out playing with my shaft and moved to my heavy balls. He
then progressed to stroking me like I was stroking him. He did as I did so
the faster I stroked him the faster he stroked me. Finally, I had hit the
point of no return and told him I was about to cum. Dave did not know what
I was talking about but he soon found out as I shot my cum across the
bathroom floor. I put my hand on his to stop him from stroking because of
the intense feeling.
"Are you ok?" Dave asked as he looked at his cum covered hand and
floor.
When I could speak I said, "Yea. I am fine. That was so
good. Thanks. But, I do not think we need to tell anyone what we did
including your mother."
"Ok. Can we eat? I am hungry." He replied.
We got cleaned up and dressed then went to the kitchen. While I
finished up dinner we talked about masturbation and what had happened in
the bathroom. We continued the talk while we ate and then cleaned up the
kitchen still talking about sex. We went to the living room to watch TV but
instead we talked about the ways guys have sex together. I made it clear
that I was not gay but was just curious and if he was interested we could
learn together. He was more than willing to play some sex games. I looked
at the clock and noticed it was time for him to get into bed. We went to
his bedroom and Dave got into bed. Without thinking I leaned over and
kissed him on the mouth while reaching between his legs giving his little
cock a loving squeeze.
"Sleep well. We will play some more tomorrow night." I said.
"Ok. Thanks for being my friend." Dave replied.
I smiled and patted him on the head to let him know I felt the
same. I closed the door then went to the living room to do my own
homework. I worked on homework but really did not know what I had done as
all I could think of was Dave's cock and what we were going to try the next
night. His mom showed up and my father came and picked me up. I got home
and finished my homework. I took a shower and got into bed. All I could
think of while in bed was Dave and his young cute naked body. My hand
slipped down to my dick and began stroking. Within minutes I came. I
cleaned up and fell asleep dreaming of what the next day would bring.
The next day started just like all the others. I got to Dave's
house just before he got home and when he got there we did his homework. It
was hard for me to concentrate as my mind was on his dick. He did not seem
to have any thoughts of sex as he was not saying anything and was able to
do his homework better than I was. My cock was up and down as I planned
what to do when I got the chance. I actually could feel the pre-cum oozing
from its tiny slit.
When we finished his homework I asked him if he would like to play
something new inside. He wanted to know what game so I said it was
something like what we had done the day before. For the first time he
smiled and was interested to hear more.
"The first thing is you will need to take a bath to get your little
pecker all clean. If you do not mind I will get in the tub with you so I
too can get clean." I suggested.
He smiled again and said, "Yes, that sounds like fun."
We headed to the bathroom taking our clothes off as we walked and
by the time we got to the bathroom we were both naked. I filled the tub
with warm water and we got in facing each other. He reached over and
grabbed my growing cock and I reached over and grabbed his. We rubbed each
other making each other's cock grow to their maximum length. I do not know
about Dave but I was so close to cumming I had to stop him before I
erupted. We finished up and dried off. I took him by the hand and led him
to his bedroom where I had him lay down on the bed. I then climbed on top
but placed my head between his spread legs and placed my cock above his
mouth. I told him to open his mouth and let my dick find its way inside his
warm mouth. I took his cock inside my mouth and lowered my dick into his. I
pumped his cock in and out of my mouth as I thrust my cock in and out of
his hot mouth.
We were pumping hot and heavy in the '69' position both enjoying
the feel of a cock in our mouth and also our cock in another mouth. It was
like having double pleasure. His cock being so small I was able to also
slide his balls in my mouth along with his cock. I sucked hard and in a
short time period I felt his body tense up and shake before going limp. He
had just had an orgasm. It was a dry one as he was not producing cum yet
but the feelings were still there. I was not far behind but I warned him to
relax and not to swallow. I told him to just let the warm liquid flow down
this throat.
I was pumping his face with my cock with my balls slapping at his
nose and face as I fucked his mouth. I could hold back no longer and let go
with several hot streams of cum. The little eight year old boy took all the
cum I had and did so like he had been having oral sex for years. Once my
balls were drained I dismounted his face telling him how much fun I had and
how I hoped he had enjoyed it also. He said he loved doing it and would
like to do more in the future.
We cleaned up a bit and walked to the kitchen to find something for
dinner. We both decided to stay naked until he had to go to bed. We ate and
then retired to the living room to watch some TV. We cuddled together as we
watched a show but our hands roamed over each other's body and before Dave
made it to bed we had both cum one more time. I knew it would be a few
years before Dave actually shot cum and was really hoping I was going to be
there the first time he did.
Dave got dressed for bed and climbed under the sheets. I too got
dressed and went to do my own homework. This time I was able to concentrate
better as I knew we were now on our way to an open sexual relationship and
that I was going to be able to do anything I wanted. His mother showed up
and I was home in bed before I knew it. I did not jack off again as I
wanted to build up some extra cum for my new sex boy toy.
Wednesday arrived with me at his place as he got home from
school. Dave went to the bathroom and then to his room before coming to the
living room to do homework. This was normal but what was not normal was he
was totally naked when he walked in. His little cock sticking straight out
as he bounced into the room. I looked at him and smiled.
"Cute, but we have to do homework before we 'play'." I said with a
tone of disappointment in my voice.
"I know. I just like being naked around you. If you want you can
take your clothes off too." He replied.
I could feel my cock pressing against my shorts and the thought of
letting it free was very inviting. The look in his eye told me he really
wanted me naked too so I pulled my shirt off and my shorts and underwear
came down in one swift move. We sat on the couch side by side working on
homework with our cocks rock hard. He would reach over and touch me and I
would reach over and touch him but we worked on homework until it was
finished. He took his books and put them away. He returned to the living
room to find me stroking my cock.
"Stand by the couch and I will be right back." I told him as I
walked to the bathroom.
I grabbed a couple towels and some lube and walked back to the
couch. I placed one big towel on the couch and laid down on it. I lubed up
my cock and then lubed his cock and added some between his legs.
"I want you to climb on top of me and I will put my cock between
your legs. Your cock will be rubbing on my pelvic area while my cock rubs
between your butt cheeks. You will need to put your legs together tight and
when I get it in position you will need to hump your cock against me." I
instructed him.
He did just as I said and was fucking my dick between his butt
cheeks. I could feel his hard little cock with each thrust he made. I am
not sure if I liked the feel of his cock or the feel of my cock on his skin
better. I put my hands on each side of his butt and helped him pump up and
down on my cock. I could feel my cum starting to flow from my balls and I
lost control. I started fucking him back. Our bare skin was slapping each
other and with the lube made a loud sexy sound. I thrust up as Dave thrust
down and his legs gripped my cock like a vice.
"Fuck, Dave, I am about to blow. Yes!!! I am
cumming...Fuckkkkkkkkk!" I yelled as my cum shot from my dick head.
My cum coated his back as I tried to catch my breath. His little
pecker to was throbbing like it had just shot a load as big as mine but
since he still was not shooting cum it was just going through the
motions. I could tell he had just had an orgasm even though he did not
shoot. When I could talk I told him to slide off me to the couch but to
stay on his stomach. He did and I cleaned up the cum from his back. I told
him I had about the best orgasm I had ever had. He smiled and said he liked
it too.
We got dressed and went outside for awhile. When we were tired we
went in to eat then a bath and to bed. His mother got home and my dad
picked me up. I got home and went right to sleep. Since I had taken a bath
with Dave there was no need for a shower.
The rest of the week went pretty much the same. We had a lot of
oral sex, masturbation, and humping. I was cumming on or in his mouth at
least once a night and sometimes twice. All week long I was sleeping really
well because I was so sexually satisfied. It was almost like we were a
couple. I was no longer looking for a girlfriend as I had no reason. I was
having all the sex I wanted, I was getting paid to have fun, and still had
all the freedom I wanted.
Thursday night when Dave's mom showed up I could see in her face
there was a problem. Thoughts raced through my mind like, 'Did she find out
I was fucking her son?', 'Did she smell the cum soaked towels?', and 'Had
Dave said something he should not have said?'. I did not know if I should
say something or wait for her to say it.
Finally, I said, "Is something wrong? You look like something is
bothering you."
"You are very observant. Yes, and I hope you can help me out. I
just found out today I am going to have to work Saturday. I have to be
there at 8:00 and will have to work until 4:00 or 5:00. I was hoping you
could watch Dave for me. If you can you can just stay Friday night." She
begged.
"I do not have plans for Saturday and Dave and I are really good
friends so, yes, I can stay Friday night and Saturday but I will have to
ask when my Dad gets here." I answered.
She looked relived giving me a big hug and kiss on the cheek. I
could feel her breasts as she pressed them into me. I could feel my cock
raising to attention as she hugged me and I was sure she could feel the
hardness grow as she took her time breaking the embrace. When we broke she
smiled at me and it was a different type of smile. It was an evil sexy
smile. Thoughts raced through my mind as where would I sleep Friday
night. Will she let me sleep with her or with Dave. Maybe she will just
have me sleep on the couch. My dad showed up and I explained it to him. He
told me it was fine so I went back in and told her I will plan to stay
Friday night.
"Where will I sleep?" I asked.
"Well since Dave has a big bed you can sleep with him if you
want. If not you can sleep on the couch." She answered.
Well that answers that question. I will not be sleeping with
her. Then I replied, "I do not mind sleeping with Dave."
I got home and went to bed dreaming about what it would be like to
sleep with Dave's mom and better yet sleeping with Dave and his mother at
the same time. Friday arrived and all I could think of was sleeping in bed
with Dave. When Dave got home I told him what was going on and he was as
excited as I was. We decided not to do anything but play until we were in
bed together. I explained that I was not sure we could do anything until
the next morning because his mother might hear us fucking. He understood
but still wanted to wait. That night we played outside and took a bath
together teasing each other's cock every chance we had. We were both so
excited it was hard to keep from getting right to the sex.
"I am not sure I want to wait till morning to fuck you." I told
Dave while we ate dinner.
"Yea, I agree." Dave replied as he got up from his seat and put his
face in my lap taking my full member in his mouth without any notice.
He sucked hard but not for long before he returned to his seat
smiling at me.
"Fuck you." I said in a teasing sort of way.
He just smiled at me and continued eating. I reach over and grabbed
his hard cock and started pumping on it with my hand. I jacked his cock for
several minutes and when I could tell he was just about to have an orgasm I
stopped. I just looked at him and smiled.
"Fuck you too." He then said in a playful tone.
I had him in bed at 8:00 and his mother showed up around 9:00. She
told me again how grateful she was and would make it up to me someday. I
just smiled telling her I was going to bed. She took a shower and headed
off to her own bed after checking on Dave, giving him a kiss
goodnight. Once I knew she was out of the room and was not coming back I
took off all my clothes and slipped in bed holding Dave. I reached over and
pulled Dave's underwear off leaving him too naked. I spooned him with my
dick pressed in his warm butt crack. I slowly fucked his crack. He did not
move much and the more I pumped the more pre-cum that leaked out which made
his crack even more exciting. This caused me to fuck harder and faster. He
had made me so excited from teasing me that there was no way I could sleep
until I came. I quietly fucked his butt crack as he slept. It took a few
minutes but I finally got to the point I could not hold back. I came
filling his crack with cum. I held him tight and drifted off to sleep as
the cum in his crack dried.
I am not sure how or when but sometime during the night we switched
positions. He ended up holding me with his hard cock in my butt crack. The
next morning when we woke up I looked at the clock. Without moving I told
Dave that his mother should have already left so we could do whatever he
wanted.
I then got an idea and asked, "Would you like to fuck my butt hole?
You know put your cock inside me?"
"Yes." He quietly answered.
I reached over and grabbed the lube that I had ready. I was not
sure what we would do but I wanted to be ready. I reached around with some
on my finger and rubbed it on my hole. I gave Dave some and told him to
lube his cock up and to press it to my butt hole. When I could feel it in
the right place I told him to push. I pushed back against him and it
slipped in without much pain or trouble. I told him to fuck me which he
did. He was pounding hard enough I could feel his balls slapping my
skin. His fucking picked up and at one point I thought he was going to push
me off the bed. He was really going after my hole and then all of a sudden
his body tightened up and he grabbed me tight and shoved his cock as far
inside my butt hole as he could. His body shook as I could tell he had an
orgasm harder than he had ever had one before.
"Thanks." Dave said as he backed out of my butt hole.
I wanted so bad to plug my cock into his butt hole but I knew his
was just way too small so I just had him give me a blowjob. I shot a huge
load down his throat which he really enjoyed. We got up and ate breakfast
staying naked until we knew his mother would be home. We got dressed right
before she got home. When I got home I took a nap because I was totally
exhausted from all the sex Dave and I had that day.
The next week things got back to normal except we had a lot less
time to fuck. We decided we would try to have sleepovers from time to
time. But then again that is another story.