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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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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