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K R I S T E N' S C O L L E C T I O N
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WARNING!
This text file contains sexually explicit
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Baby Sitting Ryan
by Paul Wilson (paulwilson45@hotmail.com)
***
I was really excited when Ryan's mom asked me if I
would baby sit Ryan for the weekend while she went to
his older brother's parents weekend at college. I had
just turned 14, and Ryan was 10. The family had known
me for years, and trusted me to make sure Ryan was OK
for the weekend. (mm, youths, 1st-gay-expr)
***
Ryan was the cutest kid I knew. I met the family when
they moved in when Ryan was just 6, and he attracted me
from the beginning. He was a lively little towhead,
slim as a beanpole, and best of all, loved to skinny
dip. His family had a pool in a well protected yard,
and they all swam in the nude. Especially Ryan.
The other members of the family would cover up when I
came over, but not Ryan. It was almost as though he was
showing off. He had the cutest little uncircumcised
penis, and his balls hung free. I loved to watch them
bounce when he jumped around. I had skinny dipped with
Ryan several times when I babysat for him, but this was
to be the first overnight.
When I arrived that afternoon, Ryan and his good friend
Paul were in the pool, skinny dipping of course. I'd
never seen Paul naked before, but though he was cute,
Ryan was better to look at. His mother saw me looking
out the sliding glass door, and said, "If it bothers
you, I'll tell them to put on suits."
I said, "No, that's OK, let them have their fun." In my
mind I was thinking what a waste it would be to cover
that beauty up.
His mom left saying that Paul had to leave at 5 pm
sharp, since his family was going out. After she left,
I went out and said hi, and undressed, figuring I might
as well get naked, too. I lay back on a lounge chair
just watching the two boys frolicking. Every so often
one of them would go up to the pool jet and hang in
front of it, enjoying the water pressure on his penis.
I'd seen Ryan doing this before, so it didn't surprise
me. But it did excite me, and I got a partial hard on.
When I did, they both got out of the pool and lay back
on lounge chairs, obviously eying my partial erection.
They both had little boners of their own, and giggled
as they wagged them at me.
I knew they were interested in my penis, since it was
larger than theirs. It wasn't big; maybe 4 1/2 inches,
and I had just a little bit of pubic hair.
Pretty soon Paul had to go home, so I told Ryan to get
out while I cooked a frozen pizza. He ran into the
house still naked, and put on a pair of shorts and a
tee shirt.
After dinner Ryan played video games for a while, and I
settled down into the one comfortable chair in the
family room to watch TV. Pretty soon Ryan said he was
going to get ready for bed, and went upstairs. My heart
jumped, since the last time I'd sat for him he'd worn
only very thin and flimsy summer shortie PJs, and he
liked to crowd into the recliner with me. Tonight was
the same. He came back down in just his shortie pjs,
looking cuter than ever.
And sure enough, he climbed into the recliner,
scrunching in beside me. His slim body felt so warm and
comfy against my hip and legs. I put my arm around his
shoulder, and my hand rested on his hip. Ryan just
relaxed, with his arm in my lap. I could feel the
pressure of his arm in my crotch, and I knew that if I
got hard he'd feel it. That didn't take long.
With my hand on his hip, I couldn't help rubbing my
fingers lightly up and down his hip. He seemed to like
it, so I did it more, running my hand down to his
thigh, and brushing the fine little hairs softly. I
brushed first on the outside of his thigh, then across
the top, to the inside. The muscles felt firm, but the
skin was soft and silky. I found my fingers at the leg
opening of his PJs, just below his balls.
By now I was fully hard, with my penis straining in my
pants. Ryan's arm was still there, right up against my
hard penis. No way could he not feel that I had a
boner. He even moved his arm slightly, stimulating my
penis.
I couldn't resist the temptation, as I slowly slipped
my first two fingers under the leg band of Ryan's PJs,
moving upward until the rested on the underside of his
balls. He did nothing to stop me, so I caressed them
lightly, then used all my fingers to roll them around
gently. They were loose in his sack; little egg shaped
that felt firm in the softness of his nut-sack. Then I
moved up, and brushed his little penis. It was hard as
a rock, sticking straight out. I took my first two
fingers and encircled it, and rubbed gently up and
down. Ryan just sighed with pleasure.
I began playing with his foreskin, something I had
wanted to do for a long time. I was surprised at how
easy it was to pull back; it just kind of rolled back,
and I could feel the head, which was very warm and
damp.
Just then Ryan moved, and I was afraid he was going to
stop me, but instead he put his hands on the waistband
of his PJ pants, and pushed them down while raising his
butt up. Then he kicked them off, and when he lowered
himself back down, he did so right in my lap, so my
penis was right under his butt. He kind of jiggled back
and forth, so it rested in his butt crack. That felt
really good, and I resumed playing with his penis.
After a minute or so, Ryan whispered, "Here, I need to
go get something. Take off your clothes while I'm gone.
He hopped up and left the room quickly, tossing his PJ
top on the floor as he went. I did as ordered, and
stripped naked, sitting back in the recliner wondering
what was going to happen next. Ryan came back in a
second, with a small tube in his hand, and resumed his
position laying on top of me with my penis in his butt
crack.
"What's that?" I asked, looking at the tube.
"My brother's lube. You'll see what its for."
We both lay there for a little bit, just enjoying the
feelings, then Ryan moved up, freeing my penis. "This
is how my brother does it," he said, and he squirted
the lube on my penis and rubbed it in so it was all
very slick. That felt good, but I didn't know how much
better it was about to get.
Ryan then moved back down, but was reaching down to
hold my penis, and he guided it to his butt hole. I
started to get the idea of what he was doing, and was
shocked and excited at the same time. He was going to
push my penis into him! And this is what his brother
did with him? Wow. I was in disbelief.
Sure enough, when Ryan had my penis right on top of his
hole, he began to slide down onto it. Even though I
wasn't all that big, I doubted it would fit into him,
at least not without hurting him. But he showed no
signs of pain, though he went slowly and carefully. The
hardest part was getting the head in. From there it
just slid on in, and I felt my penis engulfed in a
warm, soft, but tight grip.
He pushed all the way down, and my penis was all the
way in him, feeling great. He was able to move up and
down on top of my, and I matched his movements, so my
penis was moving in and out so that it was getting
stroked good. I reached around again and grabbed his
penis, and started jacking him off while he impaled
himself on me. Ohh, it felt soooooo good. I never
expected anything could feel as good. I could feel
myself coming close to orgasm, then suddenly Ryan
tensed, and I knew he was close, too.
I pulled his foreskin all the way back and gripped him
harder, just moving my hand a little, and then I could
feel a pulse in his penis, accompanied by a clamping of
his butt muscles around my own penis, then a little
delay and a second pulse, then a series of fast, strong
jerks in his penis and equally rapid clamping in his
butt. That pushed me over the edge, and I came, too,
with my own throbs matching the timing of the clampings
of his ass muscles. It was like he was milking me, as I
shot 5 or 6 strong jets of jism into his butt.
When it was all over, we both lay panting, and for the
first time, my penis didn't get soft after an orgasm.
It stayed hard and lodged inside Ryan, and felt great.
After about 5 minutes Ryan started to move again. I
thought he was going to pull off of me, but no, he was
going at it again, moving my penis back and forth in
his butt. I still had his penis in my hand, and it,
too, was still hard, so I started stroking it again.
This time it took a little longer, but felt just as
good. Again, his orgasm triggered mine, as his ass
clamped around my penis really hard. And again we lay
panting.
When he got his breath, Ryan whispered, "That was a lot
better than when my brother does it. He is rough, but
you're gentle."
"Do you do this with him much?"
"Yeah, whenever he comes home from school."
"How long have you guys been doing this?"
"Five years or so. He started doing me when I was
little, even before he could shoot sperm. I like it a
lot, but he has started to get rougher. I need to get
him to calm down."
"Think he will?"
"I think so. He loves me and tells me he doesn't want
to hurt me, but he just can't resist doing me whenever
he can. I like it a lot, so don't try to stop him. Just
last weekend he was home from school and we couldn't
get alone all day, so he sneaked into my bedroom after
I was asleep and did me. I woke up, and it felt great.
But then he get going harder and faster, and it hurt a
little. But I think if I ask him he'll slow down."
"I hope so, I'd hate for him to hurt you."
Then Ryan pulled up, and my penis popped out of his
ass.
"I'm really tired," Ryan said. "I'm going to bed.
Thanks for the fun."
"Seems to have been your idea, but I enjoyed it, too."
"You want to sleep with me? Then you can do me in the
morning if you want."
"You bet. Lets go."
Neither of us got dressed again, and I crawled into
Ryan's bed with him. We went to sleep intertwined, and
it felt great to feel his warm little body next to
mine. And he was wrong; we didn't wait till morning for
me to 'do him;' I woke in the middle of the night with
him playing with my penis, and we did it again right
then. And again in the morning! What a little horn-
ball.
Since his parents were away until the next day, we
never got dressed, and he had me 'do him' on the lounge
chair by the pool, the same way we had done it the
night before. He told me this was his brother's
favorite way of doing it, and he liked it that way,
too.
I asked him if he ever did this with his friend Paul,
and he admitted they did it a lot.
"How about your brother; does he do it with Paul?"
"No, Paul wants to try it with him, but my brother
won't. He says he only loves me." A long pause, then he
added, "Paul and I have talked about doing it with you.
Would you like to do it with him, too?"
I was surprised by that, and thought about it a bit.
"Yeah, that would be fun. And I'd like to watch the two
of you do it."
Ryan laughed, and said he'd see what he could do.
END
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This story was written as an adult fantasy. The author
does not condone the described behavior in real life.
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Kristen's collection - Directory 56