Date: Sat, 22 Oct 2016 01:52:38 +0000 (UTC)
From: ShortStories@PlayTime69.e4ward.com
Subject: Babysitting Job Chapter 2 - (b/B/F, Bb, BF, 1st, anal,  ped, Teen2)

(b/B/F, Bb, BF, 1st, anal,  ped, Teen2)

	This story is 100% fiction and is for mature readers only. It is a
fantasy involving sex acts of children and an adult. You can see a list of
all my stories on the authors page under the author, Playtime69.  Comments
are appreciated at ShortStories@PlayTime69.e4ward.com.

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                                   Babysitting Job
                                (Losing My Virginity)
                                   by: Playtime69


	Dave's mom was so glad I had been watching him after school, when
there was no school, and some Saturdays that when summer came she wanted to
do something special for me. It was about the same time summer vacation
started the apartment complex they lived in opened their swimming
pool. Cathy, that was Dave's mom's name, invited me over on a Saturday for
a swim and dinner. She had already asked me to stay with Dave each day
during the summer so she could keep her job. She was going to pay me more
but not near what she would have to pay for a day care center.

	Let me take a break from the story to describe Cathy. She was only
27 years old. She had got pregnant when she was 17 but Dave was born just
shortly after she turned 18. She was better looking than a lot of the girls
at school and a whole lot easier to talk to. Her breasts were a nice 36C
and very firm. She had long light brown hair usually pulled back into a
pony tail. She was a nice 5'3" tall with a small hot looking butt.

	I was now 16 years old with Dave being 9 and still very cute for a
boy. We continued to play with each other masturbating, oral sex, and he
even fucked my butt hole from time to time. I was still a virgin because I
did not have time to date. I was now allowed but watching Dave each day I
did not get out much and since my sexual appetite was being quenched by
Dave I really did not care. I did on the other hand enjoy seeing Cathy each
night when she got home. She was always dressed nicely and just the look of
her body gave me something to dream of when I was in bed at home. I would
jack off to the thoughts of what her pussy looked like and wondered if she
shaved her pussy hair or if she let it grow. I would masturbate each way
but found her hairless pussy got me off faster.

	"Do not forget to be here about 10:00 tomorrow morning and do not
forget to bring a swim suit." Cathy said with a smile.

	"Ok. I cannot wait. It has been a while since I got to swim in a
pool and really miss it." I responded as I left their apartment Friday
night.

	That night I showered and masturbated in bed dreaming of Cathy's
shaved pussy and wondering what kind of a suit she would be wearing the
next day. Saturday morning I was up and dressed in my swimming suit under
my shorts as I sat in the kitchen eating breakfast.

	"I see you are ready to have some fun today for a change. I am glad
you have been helping Cathy out and am really glad she is letting you be
her guest at their apartment pool."  My mom said as I ate.

	"Me too. I am glad I can help and Dave is fun to be around
anyway. I think he likes having another guy he can talk to about things." I
replied.

	We talked about school and other things as I ate. It was getting
late so I finished up and headed out the door. I got to their door right at
10:00. We all headed out together with towels in hand to the pool. There
was a few other people in the water and some just laying out. We picked
some chairs to put our stuff on and off came the shorts and shirts. Dave
was wearing a little pair of spandex swimwear and I had mine on but since I
was older and bigger mine was not quite so small or tight.

	Cathy slipped her shirt off and then her shorts and for the first
time I got to see what a real woman looked like up close. She had on a pink
two piece bikini. The top covered her pretty well and the bottoms covered
her slit and butt crack but not much else. I could not help but stare at
her body as she stood in front of me. I am sure my mouth was open as my
pecker started growing.

	"You might want to think about something else before you show more
than you need to in public." Cathy said as she looked at my crotch.

	"Oh, sorry. I. Ummm..." I mumbled as I turned and jumped in to
pool.

	I quickly found Dave and started playing with him with some of the
toys floating in the pool. We talked about how hot his mother looked and
how much I wanted to cum in his mouth. I think he knew I really wanted to
cum in his mother's cunt but was afraid to say so. It was not long before
Cathy jumped in the pool and was playing with the two of us. I could feel
her brush up against my cock from time to time but was not sure if it was
on purpose of just by accident.  It did not matter as I enjoyed it either
way. We were at the pool until about 3:00 when we decided to go in and
eat. We were all pretty much red from the sun and all wrinkled from the
water but we all had a lot of fun. We all showered at the pool before
leaving so when we got back to the apartment we were all still wet.

	"Let's all get into dry clothes and eat. It will not take me long
to fix dinner then maybe we can watch a movie together if you want to
stay." Cathy mentioned as she headed off to her bedroom to change.

	I went into Dave's room where we both stripped. My cock stiffened
up as I looked at Dave's naked body. He saw my cock and smiled and said he
wished we could play but with his mother in the next room it was too
dangerous. We got dressed and went to help in the kitchen.

	When I walked into the kitchen I must have had the same look on my
face as when I saw Cathy in the swim suit the first time because she made a
comment about my cock busting out of my shorts. She was now wearing the
tiniest white shorts I had ever seen. There was almost nothing to them. Her
top was simply a half shirt with no bra. Dave paid no attention to what she
was wearing like it was normal. I was able to get him out of the room so I
could ask him if what she was wearing was normal. He giggled and told me
that what she had on was more than what she normally wore around the
house. When I heard that my mouth dropped open figuring Dave might just
know if her pussy hair was shaved or bushy but before I could ask we hear
his mom call that it was ready and for us to get in the kitchen to eat. I
ran in and sat down to eat.  The meal was plain but very good. We chatted
about different stuff but eventually got to a discussion of what we did
after school each day. We just said the normal stuff leaving out the sex
part. We finished eating and had desert and once that was done we headed
off to the living room.

	We were on the way when all of a sudden Cathy asked, "Mike, what is
your favorite position to fuck Dave?"

 	I must have turned white as I could feel all the blood rush from my
head. I could not say anything even if I wanted to. I just froze and stood
there in the hall like a deer in headlights.  Cathy asked if I was ok. I
just mumbled something not sure what but she finally let me know that it
was ok. She told me she had found dried cum on some towels and some of
Dave's underwear. She also told us she figured Dave was not shooting cum
yet so figured it was mine.

	When I finally figured out I was not in trouble I said, "Um, well,
I really like it when my cock is between his legs and his cock rubs my
skin. I like shooting my cum on his back and butt crack. I guess it is a
feeling close to having sex."

	"That sounds like fun. Are you still a virgin?" She asked.

	I looked down not really wanting to answer but finally did. I told
her I was still a virgin and figured Dave's butt hole was too small to put
my dick into. I explained how we like sucking each other's cock and how
Dave had not started shooting cum yet. I told her how he did have the
feeling of cumming just not the cum yet. I admitted we did have sex in one
form or the other most every day. I could tell she was enjoying my talk as
I saw her hand slip to her pussy.  During this talk we moved slowly to the
living room and sat on the couch. Dave was not saying much but I could tell
he too was enjoying the talk as I could see a little bulge in his shorts.

	Finally Cathy said, "Mike, how would you like to fuck my pussy?"

	"I. Um. Well, um. I guess so but what about Dave? Dave is that ok
with you?" I asked.

	"Can I watch?" Dave then asked.

	I looked at Cathy to see if it was ok with her. She nodded her head
yes saying she would love for him to watch. Then she did something I
thought would only happen in my dreams. She reached up pulling her half
shirt off revealing her perfect breasts. My mouth opened as I could feel my
cock jump to attention. She smiled at me as she pointed to my shirt. She
told me I was way over dressed and for me to strip naked. I went for it
taking my shirt off first then my shorts and underwear. I was totally naked
in front of an older woman. Dave too was naked without being told. The only
thing left was Cathy's shorts and panties and in one swift move she was
bare and for the first time I have the answer to my question. Her pussy
hair was not shaved but was not hairy either. It was trimmed very nicely in
a wide strip but yet the pussy lips were shaved as close as a new born
girl's pussy. My cock was straining against its own skin to get larger as
it grew bigger than I had ever known. Cathy told me to lay down on the
floor where she have placed some blankets and pillows. She then mounted
me. My cock slowly entered her steaming hot snatch and her eyes glued to
mine as we faced each other. She was watching to see what gave me the most
pleasure. When my cock disappeared inside her cunt I instantly felt my cum
wanting out. I had to tell myself not to cum at least not just yet.

	"Fuck me back as my pussy sucks the cum from your balls." She
demanded as she pumped her pussy up and down on my dick.

	I did as requesting only making it harder not to cum. I thrust my
hips up forcing my dick to penetrate deeper into her pussy hole. I looked
over to see Dave intensely watching as I fuck his mother. He did not look
upset matter of fact he looked like he was enjoying the show. His little
cock hard as a rock and sticking straight out in front of his body. I
reached up taking hold of his little cock where I started stroking it to
make him feel good. The more I fucked Cathy the more she fucked me back and
the more she fucked me the faster I jacked Dave's little cock.  This was
just a fucking frenzy as I could no longer hold it.

	"I am going to cum in your pussy." I said out loud to Cathy.

	"Yes, fuck my pussy. Give me your virgin cum! Make me your little
slut girl. Come on and blast that load of yours inside my pussy." Cathy
yelled as she watched me fondle Dave's cock and balls.

	With that I blew my load. Cathy put all her pressure on my body as
she sat on my cock.  She wiggled her butt which ground her wet cum filled
cunt into my privates. I could feel her pussy contract around my shaft then
all of a sudden I could feel wetness from her hole as she expelled her own
liquid orgasm all around my cock.

	"Wow, that so sooooooo good." I mentioned as my breathing was
returning back to normal.

	"I am glad you liked it but now it is Dave's turn. Do you mind if
he fucks your butt hole while I watch?" Cathy instantly asked.

	It did not even take a minute before I was on my hands and knees
ready to accept his dick in my ass. I looked around to see Cathy sticking
her fingers inside her cunt then taking the cum and sliding it inside my
hole. She did this several times before telling Dave to enjoy fucking my
butt hole using mommy's cum as a lubricant. Just hearing what she was
saying was getting me hard again and I already was hoping to fuck her again
before I had to go home.

	I felt a little pressure then pleasure as Dave's cock penetrated my
puckered butt hole.  He pounded me hard for a few minutes then his little
body shook and tensed up. He had just had another dry orgasm and was loving
the afterglow. When he pulled out I immediately asked if I could fuck Cathy
again.

	"I guess you liked it the first time?" She replied.

	I nodded my head, 'yes'. She laid down on the floor and I climbed
on top forcing my hard again cock into her soaking wet snatch. I pounded
hard and fast and within five more minutes I had cum a second time. We got
up then all went to the bathroom together to clean up. She washed my cock
and dried it off then she did the same to her son. She then forced us to
watch as she cleaned the cum from her own pussy. When we were all done I
got dressed and left hoping this was going to be a normal thing to happen
each night. It did not happen every night as she was usually too tired but
on occasion I did get to fuck her. I did get all the sexual activity I
wanted from Dave, her son. We even played together from time to time. The
one thing I never got to see and am not sure it even happened was Dave
fucking his own mother. If he did I never found out about it.

                                       The End