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Nifty - Gay - Young Friends - Babysitting Ryan

Date: Wed, 06 Nov 2002 16:35:24 -0600
From: Paul Wilson <>
Subject: Babysitting Ryan

I was really excited when Ryan's mom asked me if I would baby sit for 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.

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

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

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

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
ballsack. 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

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

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
hornball. 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.

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Nifty - Gay - Young Friends - Babysitting Ryan