Date: Wed, 12 Feb 2020 12:09:14 +0000
From: Strange writer <Strangestorywriter@protonmail.com>
Subject: Surprise at the Pool Chapter 9-14

This is a continuation of a story that has been floating around in my head
for awhile. In this section there is one encounter with a girl, thus the
bisexual category listing.

I would love to know if this story appeals to readers, and if I should
continue to submit these chapters and further stories. Please send any
feedback to strangestorywriter@protonmail.com.

This story describes sex between adults and children and is a complete
figment of my imagination. All of the characters are fictional and not
taken from real life in any way. If reading this type of story is illegal
where you live, please stop reading.

Lastly, if you enjoy reading stories on the archive, and can't imagine the
archive disappearing one day, consider making a donation.
http://donate.nifty.org/donate.html

Thanks, Strange Writer


Chapter 9

If I was smart, I would have planned out the following day before he ran
off. Would we go about the usual swim and go our separate ways? Would Robby
be overcome with guilt and not want to see me? Or, would it be another
ball-draining meet up? One of those things sounded awesome to me!

Since no plans were made, I headed over to the pool to wait for his
appearance. I swam my laps when he hadn't shown up, then took a seat in my
usual area. Eventually he showed up, running out with another boy giving
chase. They sprinted to some lounge chairs, drawing a whistle from the
lifeguard telling them to slow down. They threw their stuff down, and then
Robby gave his friend a "follow-me" wave.

They headed out, when I quickly realized that they were headed toward
me. "Oh, no," I thought, "this is a bad idea."

Robby was in the lead, sashaying between chairs until they got close enough
for him to say, "Hi Mr. Lucas."

I answered with a friendly, "Hi, Robby, hows it going?" but was thinking
that Robby was exposing me to unnecessary danger.

"Good," he said, "I wanted you to meet my friend Adam," he gestured to the
skinny boy 1/2 a step behind him. We exchanged greetings with small waves.
"He's on the swim team with me, and when I moved into a faster lane he
asked me what I'd been doing. I told him about you helping me with my
stroke."

"I've sure been helping with your stroke," I thought, "just not the one
that you're talking about."

I took a look at Adam and noticed that he was very thin and a little taller
than Robby. He had long eyelashes and very pink lips. As he stood with a
tilt to his hips, I realized that his gaze was traveling over my body while
I was checking out his. What had started as fear of Robby doing something
irrational and dangerous, turned to a realization that he had picked up on
something with this kid, and maybe saw a co-conspirator. When I looked at
Robby, he was smiling away. What a kid.

After exchanging pleasantries, the boys decided to go swim some laps. As
they headed to the pool, I stared at Robby's Lycra covered butt, unable to
believe that 24 hours ago I had my tongue digging into that hidden asshole.
I guess there's no such fun today.

When my time at the pool was done, I headed over to the main pool area
where the boys were splashing. Now that I was introduced and my presence
explained, I felt like I almost needed to say goodbye in order to keep up
appearances. The boys had finished swimming laps and had been splashing
around in the main section for almost an hour. Adam was sitting up on the
side of the pool as I approached with Robby holding on to the wall. "I'm
heading out, have a good day, it was nice to meet you," I said, nodding
toward Adam.

"Nice to meet you," he said blocking the sun with his hand as he looked
up. He then returned to his activity, which was picking something out of
his toes. Something seemed off, then I realized that he was bending his
knee back so that his foot came behind him for inspection, like a girl or a
little boy may do. A boy Adams age would normally do it the opposite way,
looking at it between their legs. Yes, I think that Robby may be even more
clever than I thought if this is the only person that he's introduced me
to.

"See you later," Robby added, and gave another megawatt smile. Usually it'd
be tomorrow, so maybe he had something else in mind.

After getting home, I worked out the last few arrangements for the
vacation. We were leaving on Saturday and it was already Wednesday, so it
was getting down to it. I started packing my bags, made sure that I had all
of the ship's forms filled out, passport found etc. Later, when I went out
to grab the mail, I found a small blank envelope. Once I was back inside
the house, I opened it to find a hand written note in terrible print that
said, "Leave your garage open at 1," and then a smiley face.

"Risky," I thought, but looked at the clock anyway. It was 12:40 already.
Do I play this game? Could I come up with a cover story? After ruminating
for awhile, I decided that I could come up with a cover story for just this
one occasion. "I'm an English teacher, he asked me for tutoring after I got
to know him at the pool." It wouldn't set aside all suspicion, but if
someone saw him come to my house once, it would work; with the kid's
cooperation. It wouldn't work if he was there every day, his bike was
always in my driveway, or I became the neighborhood hangout for 11 year old
boys. It wasn't that hard to talk myself into these things when a gay
preteen wanted to sneak into my house to have sex with me! At 12:55 I
opened the garage door and left the door to the house unlocked.

Like clockwork, I heard noise in the garage promptly at 1, followed by the
sound of the garage door closing. Robby burst through the door with his
patented gleaming smile. He was wearing loose basketball shorts and a tank
top and seemed sweaty and out of breath. "I'm playing basketball until two,
so let's not waste time," he said as he kicked off his shoes without
untieing them. He then started to shake his hips and his shorts slid right
off his hips, falling to the ground and revealing his lack of underwear.
His cute little pecker was flaccid, hanging down over his sagging,
overheated balls, and he was a gleaming beauty as he removed his shirt
while he moved into the house. He giggled at my shocked look, then took off
running to the stairs, his naked ass flexing and jiggling with each stride.

I quickly gave pursuit, trying my best to grab at him, even making slight
contact with a cheek as he bent slightly at the top of the stairs using his
hand for balance, but he scampered away laughing. He sprinted to my
bedroom, jumped in the air, doing a spin, and landing with a thud on his
back, scissoring his legs before pulling them back and wrapping his arms
behind his knees. This left the obvious view of his pink wrinkle of a hole,
and his balls squeezing out between his closed thighs. "Lick me!" he
demanded, "I've been thinking about it all night!"

I stopped dead in my tracks and stared at the spread cheeks and exposed
asshole so freely displayed in front of me. Then I dropped down onto my
knees and grabbed his cheeks, diving in without hesitation. He was riper
today, no clean chlorine smell, more musky and sweaty. The smell was
stronger too. Still not a shit smell, but not clean. It was the scent that
I'd learn could only be boy ass.

His legs relaxed when I dug in. He slid his hands out to hold his knees,
but let the legs split and spread himself wide open for me. I slid my hands
from his butt cheeks up to the where they connected to the backs of his
thighs and held him in that wide open, relaxed position as he melted under
the pleasure my tongue was providing. My palms held his legs up while my
thumbs pulled the skin around his hole gently wider. Yet my attack on his
hole was anything but gentle, it was all strong strokes and long licks with
insistent probing into the center of his starfish.

Robby let out a sigh that indicated a total relaxation of his body, letting
his hands release his legs and his arms lay by his side limply. His eyes
closed and he turned his head to the side, laying fully back like he was
asleep. Once again I was thrilled by the way he gave himself over to me. A
show of complete trust. At the same time, his little cock was standing
soldier straight, pulsing with his heart beat and twitching when I hit a
good spot. I licked up onto his perineum and reached up to stroke him a
couple of times. I used the opportunity to wet a finger, then brought it
down to his hole while I sunk my lips over his cock.

My finger traced a couple of circles around his hole, which had opened up
slightly under pressure from my tongue. Then I added pressure to the center
as I began to pry on the tight wrinkled muscle, twisting and pulling on the
sides, while continuing to go to town on his dick. His hole easily gave
way, and suddenly my index finger sunk right into his hole up to my second
knuckle. Robby flinched but didn't pull away, instead reaching down and
grabbing my wrist to hold me in place, no further and no less. His eyes
were shut tight and he slightly winced, "it's ok," I reassured him, "just
keep relaxing and it will make you feel great." Then resumed sucking.

His ass was squeezed tight around my finger and felt warm and squishy. We
stayed locked in that position for several seconds, my finger just inside
his ass and his hand holding my wrist. Finally the stalemate ended when his
body relaxed, he sunk back into the bed and loosened his grip on my arm. I
gently began to twist my finger, circling in one place, then slightly
pulling at the sides of his anus. I was well past both of his sphincters,
and my fingertip was inside his warm rectum. With these same circling
motions, I sunk my finger slowly deeper, then pulled back slightly before
sinking to a new depth. The hot, soft sponginess of the inside of his
rectum got me so excited that my own erection was pushing uncomfortably
against my shorts.

I focused pressure on the front wall of his rectum, trying to find his
little prostate with some success, as periodically I'd hit a spot that made
his cock jump in my mouth. A second finger was out of the question without
some lube, so I kept up the pace with my single digit fucking in and out of
him, while trying to gently open his little rose. Robby was responding more
and more actively, thrusting his penis through my lips up to the root, with
his pubic area pressed against my face. He had opened his eyes and grabbed
onto my head as he fucked into me, and actually rotating his ass around on
my probing finger. The build up was quick from there until Robby gave one
last thrust and then held me tight as he let out a squeak and started
throbbing in my mouth as his orgasm overtook him.

I knew that it may make him uncomfortable, so as his climax hit, I slowly
slid my finger out of his chute. He let out a sound that was closer to
"Ahh," then any other sound as I did it. He then grabbed my head and rolled
onto his side, wrapping his legs around my head and bending forward over
the top of me. When he released his grip, I slid up the short length of his
penis, and gave one more lick, which caused a flinch, then moved up onto
the bed with him, gathering him in my arms, one hand under his butt,
keeping him curled up and the other around him from underneath holding him
to me. He turned his head to me, and we fell into a deep open mouthed
kiss. No hesitation this time over where my tongue had been. As he finally
stretched out of the fetal position, I finally had the use of both of my
hands, and used them to somewhat awkwardly slide my shorts down while still
maintaining contact with his soft lips. When I was naked, I started
stroking myself with one hand while rubbing Robby with the other. Robby
reached down and grabbed my cock and broke the kiss to look down at it,
"Somebody wishes he was your finger," he said with his usually lower lip
bite that signaled his naughty thoughts. I could only groan.

I used my weight to roll Robby onto his back, and resumed devouring his
little mouth while I began humping against his smooth groin. He wrapped his
hands around my neck and really got into the kissing, while I picked up the
pace, loving the feel of his smooth pubic area, softening cock and loose
ballsack against my seemingly huge cock compared to his young body. All of
the stimulation brought me to the edge in no time. I broke the kiss and
lifted myself off of him. Pushing myself slightly onto my knees, I started
frantically jerking off, staring down at the gorgeous body laid out below
me. I fully got onto my knees, my legs inside of his, holding him apart,
while I used my free hand to stroke all over his torso, tweaking nipples
and running down to his half hard prick. Letting out a roar, my orgasm hit,
and I aimed my cockhead at the top of his penis. The first spurt coated his
shaft, then I moved up onto his bare stomach, shooting ropes that reached
from his groin to his chest. As I came, I rubbed my cum into his body,
leaving a gleaming sticky mess.

I let my weight rest into my right elbow, and with my left index finger
touched a dollop of my cum that was nestled between Robby's balls and
thigh, then brought the finger up toward Robby's lips. I raised my eyebrows
in a "how about it" expression, and he surprised me by grabbing my wrist
with both hands and guiding my digit into his mouth while he sucked it
clean. He made some smacks of his tongue as if trying it out, then wrinkled
his nose,

"It tastes sweeter than last time, but still kind of gross."

"They say that if you try a food 10 times you will like it," I offered,
"plus they say that what you eat makes it taste different. I'll work on
eating more citrus."

"Ten times?" he replied with a frown, "hmmm."

"What did you think about having my finger inside you?"

"Um...I actually kind of liked it," he admitted, "it made me feel better,
and I actually liked being connected to you like that, if that makes any
sense."

This was the best thing that I could hear. It wasn't just the physical
sensation, but the mental attachment to me. "That is exactly how I feel," I
said, "it makes me feel like I'm part of you." Robby smiled up at me,
"there's lots of fun things that we can do back there," I added.

"I know what you want to do back there!" he blurted out with a laugh.

I looked down at him, "What do you think about that?" I asked.

He looked down over his body, "It kind of makes me excited, but I don't see
how it's possible, and it would hurt."

"It doesn't have to hurt, and you ended up liking what we've done. If you
continue to trust me we will have tons of fun with that whole region," I
said, reaching down and grabbed a handful of ass from underneath, giving it
a squeeze to emphasize my meaning. This elicited a torrent of laughter and
feet kicking. I rolled over so that I was on top of Robby and began giving
soft kissed all over his face which caused him to quiet back down.

"Emmm," he moaned, "Do you think that you could ever fit there?"

"I know that I could," I answered, "just takes patience and lube."

"I think that I want to try," he said as he started rubbing my arms and
looking at my body, "maybe we can make it happen on the ship."

My dick started clubbing up, "I like that idea a lot, we can work on it a
little before we leave."

"Oh," he started with a concerned look, "I meant to tell you, we're leaving
tomorrow. My mom wanted to surprise us, and we're going to visit my
grandparents for a few days before we head to the ship."

I was dejected, "Oh, so this is it huh? Until Sunday?"

"I guess so," he said.

"Well then, you'll have to work on it by yourself, and I'll get some things
to make it easier. Maybe I'll look at getting a small plug for you to
wear," I said, "the first days on the ship."

"What is that?"

"It's like a little cock-shaped thing, a dildo, but it's got a base so that
it only goes in so far. You wear it while you're doing other things and it
helps to loosen you up. It can feel good too, and kind of naughty," I
smiled.

"Maybe," he said, "I've heard of a dildo, I didn't know that people said
that!" he laughed.

"I guess it is pretty stupid sounding," I agreed, "anyway, you can use your
fingers like I did, just use something slippery like vasoline or
lotion. That will help you get used to having things up there and it'll be
easier to open you up when we get together again. I'll get some toys that
we can use on the boat."

I looked at the clock, it was 1:55, "Shit, you need to get cleaned up and
go home! I'll run the shower." I leaned down and gave him another kiss,
then ran to the bathroom to warm up the water.

Robby followed me in, and hugged himself to my side as we waited on the
water, "I'm going to miss you," he said.

"Me too buddy, but we're going to have the time of our lives starting
Sunday."

Robby did a quick rinse to get the drying cum off of him. Any more and it
would be suspicious that he smelled so rosy after a basket ball game. He
got dressed, we said our goodbyes, then he did a quick escape back out of
the garage.


Chapter 10

I spent the next several days getting ready for the trip. I spent some time
researching the anatomy of anal sex and the best ways to get ready. In
addition, I found an online sex toy store that sold smaller sized sex
toys. I ordered a couple of sizes of butt plugs and did the same with
dildos as well as some lube. To get it in time I had to pay extra for rush
delivery. It made me laugh, wondering how many people need their sex toys
expedited!

On Saturday I traveled to Miami to meet the boat, staying in a nice place
on the beach so that I'd be ready to board on Sunday.

On Sunday I went through the cattle call of cruise ship boarding, thinking
how funny it will be if my luggage gets searched before it's delivered to
my room, it looks like I'm a traveling dildo salesman!

I was in a low stateroom, but it was actually nicer than I expected, with a
real double bed, not the bunks that fold down from the ceiling, and a real
bathroom, not the kind where you have to close the toilet lid to take a
shower. Progress.

Like everyone else who boarded early, I headed out to get some lunch, and
like most, ended up at the buffet. It was crowded enough that I had to make
a lap trying to find a seat. As luck would have it, toward the back of the
ship, I passed by Robby, sitting with his mom and sister.

Deciding that I needed to stay in this area, I hung out until a couple left
a small table within eye site of Robby. After settling in, I spent the
whole time staring over, hoping that I'd get his attention. The girls were
both intently pecking away at their phones while Robby just sat looking
bored, until eventually he started scanning the room. I perked up, trying
to be visible without waving or looking crazy. Eventually his scan came my
way, initially passed, then jumped back, realizing what he saw. Then my
happy moment came, his beautiful permanent smile broke out on his face,
followed by his usual tell, biting his lower lip, subconsciously giving
away that he was thinking of doing naughty things with his body.

I looked around, but no one was paying attention to us. I noticed that
there was a sign for the restroom pointing just out of sight near the
entrance to the buffet. Robby was still subtly glancing my way, so I gave
the slightest head gesture, trying to indicate the bathroom. He just looked
confused. I gathered my things and got up from my table, and tried this
time to use my eyes as a signal, indicating the sign, again being as
inconspicuous as possible. Luckily the girls at his table hadn't looked up
once. Walking toward the exit, I actually reached my hands up as if I was
stretching, the gave a quick point to the bathroom sign above my head as I
walked away. As I turned the corner, I looked back and saw Robby talking to
his mother, and I got a cold chill as I noticed his sister looking my
way. Quickly I looked the other way and hustled around the corner,

I waited around the corner, but didn't go into the bathroom. An
excruciating 15 seconds passed, when finally my happy, sexy boy rounded the
corner, giving me a 1000 watt smile. We headed into the restroom without
interacting. Once inside, it was crowded and loud, with a line for the
stalls which we joined. The volume gave me an excuse to lean down close to
Robby's ear to talk. No one would give it a second thought, a dad talking
to his son, "I'm so happy to see you!" I said, not even needing to whisper,
"this is what we can do; right after the boat sails they will do a safety
drill. As soon as it's over, tell your mom that you want to go explore the
boat. Come by my room," I gave him the number, " the door will be
unlatched. Just let yourself in, ok?" Robby nodded his head and bit his lip
again.

"Say the room number back to me," I said.

Robby leaned in, and whispered it back to me, so close that I felt his
breathe on my skin, "I can't wait," he breathed out.

The line wasn't moving, so I said loudly as if I was talking to my own kid,
"let's just go back to the cabin," and started to leave, directing Robby
ahead of me. As we walked out of the entrance, Robby had moved a couple of
paces ahead of me. My breath caught as his mother and sister were right
outside waiting. I turned the opposite direction and walked away, but again
I felt like the sister looked my way. I heard his mother ask, "everything
ok?" as I moved out of earshot.

I returned to my room and started making arrangements for our rendezvous. I
organized all of the new toys, and had the lube within reach. The room had
robes available, and I decided that I would wear that when the time
came. If I had gauged Robby's expression correctly, nothing between us had
changed in our four days apart, and he would be turned on by the near
nudity. The boy loved being naughty.

I went out exploring and watched the ship leave port. There were several
announcements, Then everyone was ordered to go to their muster area for the
safety drill. I may have been the first person ever to get an erection from
that announcement!

The whole thing took about fifteen minutes, after which I hustled back to
my room, able to make quick time since I didn't have to gather and account
for my family like everyone else. I initially closed my cabin door so that
I could change, or undress as it were, but then popped the door, leaving it
unlatched. Since we weren't far out to sea yet in rough water, it stayed in
place. Then I waited.

Sitting on my bed, I started sporting an erection under my thick robe. I
sat for about 5 minutes, drumming my fingers, when I finally heard a rustle
in the hallway, followed by my door being pushed open. I jumped up and
Robbys face popped around the door, giving me a big smile. He slammed the
door as he kicked his shoes off, then ran at me while tugging his shirt
over his head. He jumped into my arms, but he was still a stocky kid, so he
knocked me right over and back onto the bed. He fell on top of me and
knocked the wind out of me, then mashed his lips onto mine, seeking my
tongue with his. The feel of his small mouth under mine made me moan and
sigh. It seemed like years since we had been together, and I wanted to
devour this beautiful boy.

My hands roamed all over his bare torso, feeling his broad back and soft
sides. I continued down, running my hands straight under the waistband of
his shorts, finding no underwear to impede my progress as my hands slid
right onto his ample soft buttocks, which flexed and released as we kissed
and Robby ground his cock into my belly. I grabbed and kneaded two big
handfuls of asscheeks, letting my index finger run up his crack, and stroke
across his sweaty hole.

Keeping my hands inside his shorts, I cupped the bottom of Robby's cheeks
and tried to gain some leverage, then, holding him tight, I sat up
slightly, picked him up, turned us around and dropped him onto the bed. As
his legs kicked up, and with my hands still in his shorts, they slid right
over his butt and I pulled them completely off in one motion.

His nail was as hard as I'd ever seen, and I dropped down onto my knees,
bringing him to my lips. He slid right through my lips and I dragged my
tongue across the underside of his cock as it came close to the back of my
mouth. On the upstroke, I released him and twirled my tongue around the
tip, causing Robby to let out an, "Oh yeah." His sexual need was like a
physical presence in the room. It made me hard as a rock, and as I sucked
his magnificent cock I undid my robe and stroked myself. This wasn't the
time to stretch things out, both of us needed release, so I didn't hold
back at all, quickly increasing to a rapid pace, Robby matching me with hip
thrusts slamming his pubis against my face. His cock was coated in my spit,
with more pooling on his groin, making his penis feel silky smooth as it
pistoned in and out of my lips.

Robby started a rhythmic series of, "Oh, oh, oh's," as his passion rose to
the breaking point. I was reaching a peak myself as I stroked myself
frantically, my mind overheated by this boy who so freely gave himself up
to his sexual needs. Robby's breathing became more ragged and his thrusts
lost their rhythm, pushing up into me in a more forceful but erratic
pace. His dick amazingly became even stiffer, literally feeling like a
piece of unbendable, skin covered metal in my mouth. Finally with one last
upward thrust, Robby held onto my head and held his groin flat against my
lips. His cock began to flex strongly against the roof of the mouth as he
let out a loud groan of release. I ran my tongue around his dick, buried in
my mouth, when suddenly I had a different taste hit my tongue. It was
sweet, and I recognized it as similar to precum.

Robby's entire body was held rigid as he stayed in a sort of half sit-up
position using my head as leverage as he rode out his climax. Finally he
released my head and collapsed back onto the bed, throwing his arms off to
the side, his chest heaving. I got up onto my feet and stood over his
gorgeous body, stroking myself. His body was laid out in front of me
completely naked and splayed out. His eyes were closed and his head turned
to the side with such a relaxed expression he could have been sleeping. On
top of the visual stimulation below me, his small emission had left a taste
in my mouth that was making me crazy.

I bent at the knees and reached my left hand out to stroke his belly,
feeling it's soft ample texture, and stroking up to his chest. Robby opened
his eyes and turned to look at me, giving me a smile, "Cum on me," he said
as if it was the most normal thing ever. That was all it took, I let out a
roar and began to unload all over Robby, covering him from cock to neck,
each shot landing with a forceful splat. I planted my left hand on the bed
beside Robby, panting through the last spasms of my own orgasm, then used
my right hand to rub my cum into Robby's torso, giving it a smooth, sticky
sheen. Robby grabbed onto my arm and followed my motions around his upper
body, sighing and encouraging the massage.

Eventually I collapsed onto the bed beside him, turned to my side and
wrapped my arms around him. Robby also turned and we began another kissing
session, less urgent, more loving. It wound down to gentle kisses, leaving
space for Robby to giggle between pecks. "What's so funny?" I asked him.

"It's nice to see you," he said flatly, reaching his hand out as if to
shake, then broke into a fit of laughter. I finally caught on, Robby
recognizing the absurdity of us not saying a word before exchanging sexual
favors! I reached over and started tickling him as we both burst out in
laughter.

"What did you tell your mom?" I asked as we settled back down.

"I said that I wanted to explore a little. I have to meet her at five at
the kids club to get signed up," he said. "But this is cool, my sister and
I are sharing a room and my mom has her own," he added excitedly, "I think
that she's out looking for a boyfriend and doesn't want to be bothered. And
Sophia could give a shit what I do, she's only worried about herself."

"Wow, that could work out great for us," I replied selfishly. I shouldn't
be excited about absentee parenting, but it was working in my favor for
sure.

"Once I get signed up, they let me check myself in and out of the club, so
my mom won't ever know where I am. I can pretend that I'm there all day,
even late at night because they do sleep under type of things until one
am. I know from before that my mom will just text me on the ship WiFi, she
never calls the kids club."

This was going to work out great, I even started chubbing up a little
thinking about the possibilities. I turned to Robby and he was biting his
lip, and still sporting a rock hard erection. I'm not sure if it had ever
gone down. "I think that this is going to be a great trip!" I said, pulling
Robby back into my arms and rolling him on top of me. I could feel his hard
poker hitting just above my groin, and my drying cum sticking us together
as I stroked down his back and over his butt. My index finger trailed back
down his crack and onto the outside of his hole, "Do you want to see some
of the toys that I got for us?"

He popped his head up, "Sure! I've been using my fingers a little like you
told me, I like how it feels."

I lifted Robby's naked body off of me, and tossed him off to the side as
best I could then went over to my suitcase and grabbed the plastic grocery
bag that held my stash. I laid out each item on the bed; lube, a dildo with
beads that consisted of a series of knots increasing in size, two butt
plugs, one small, one medium, three regular dildos, gradually increasing in
size, the biggest wider then my own erect penis. Lastly I laid out a medium
sized vibrator.

Robby picked each item up in turn, examining and asking questions, "What do
the balls do?" he asked, holding up the beads, "Is this the butt plug? This
ones hard?"

"The little balls get you used to the size increasing, and they feel good
going in and out," I explained, "it's a good place to start. The hard one
is a vibrator, lots of people like the sensation when it's inside, and it
always feels good all over on the outside." I turned it on, causing him to
jump, then gently stroked it over his back and butt. He laughed at the
sensation, then grew silent when I settled over his anus.

"And these are butt plugs," I finished, holding the smaller one up, "these
feel good going in and coming out, but they're designed to stay in place
either during playtime or, if you're up to it, you can keep it in under
your clothes and wear it around. That way you get used to having something
in your butt." Robby wrinkled his nose, "It feels naughty too, knowing that
you are the only one who knows that you're pleasuring yourself. Or you and
the person who helped," I winked. "Do you want to try a little before you
have to go?" I asked, noticing that his spike had returned to full mast.

Robby, paused for a second, then dropped onto the bed and unconvincingly
said, "ok."

"It's the same as always buddy, you have to enjoy what we're doing. I'll
tell you everything that I do before I do it, we'll take it slow, and we
won't do anything that you don't want to do, ok?

"Ok," he said perking up, "what's first?"

"First, lay back and let me get you ready," I said, with a bit of a growl
to my voice.

Robby's erection had subsided a bit as he lay on his back waiting for me. I
started at his face and stroked his jawline, down the side of his neck,
across his chest, paying attention to his nipples, down over his pudgy
belly, finally stroking the forbidden zone above his cock before settling
onto his hardening rod. A few strokes caused it to pop right back to full
size, then I rubbed the area where his legs joined his groin, slid my
fingers under his thighs and gently bent his legs at the knees so that his
feet were flat on the bed. This gave me access to his sack, which happened
to be one of the few areas not coated in my dry semen. I got back onto my
knees and drew a firm lick across his scrotum, then held his balls out of
the way so that his taint came into view. This was my next victim as my
tongue traced the edge of his sack, feeling it's firm wrinkles, contrasted
with the smooth skin below. Robby sighed as the area from balls to hole was
coated in spit and treated to a warm tongue bath.

I used my hands on the back of his thighs to gently push his legs up
further to open his asshole up to me, "Hold your legs for me baby," I
said. He spread his legs more and held with his hands behind his knees. His
hole looked clean and as I got closer, passed the sniff test. "When is the
last time that you pooped bud?"

"After we got on the boat, I had a good one," he giggled, "then I used some
wet wipes to clean up before I came over here." He gave a guilty look.

"Doesn't hurt to be prepared," I laughed. "Ok, time to enjoy." I leaned
back in, and enjoyed the mind blowing taste and texture of his ring. When
it was dry, I loved the feel of each bump of his anal muscle, when it
seemed impossible that it would ever yield. Robby started relaxing and
sighing. As I dug in, he started to lose his grip on his knees, letting his
legs fall individuality before catching them. It was time for a better
position, "Let's try something else," i said getting up. Grabbing a pillow,
I placed it next to him and patted it, "lay across that with the pillow
under your belly," I instructed.

Robby scampered over, and lay down as told, presenting his sexy big cheeks
to my view and his hole clearly on display between them, "that's better."

I had more room, so was able to get on the bed to kneel behind my sexy
boy. I grabbed his cheeks to spread him out, then went back to work on his
anus. After several minutes, I actually felt a loosening of the outer
sphincter. It was time to introduce the finger, so I sucked on my index
finger, then placed it on top of him, making small circles with slowly
increasing pressure. I used the freedom to drag my tongue all over his
cheeks, back down his taint, bathing the backs of his balls, then taking
them fully into my mouth.

Before we started I had moved the items that we might use within reach, so
I was able to grab the bottle of lube. Popping it open, I generously coated
my index finger. I spread the excess onto his hole, causing him to yelp
about the cold, "It'll warm up in no time," I assured, bringing my finger
back and resuming the gentle prying. This time, the lube did its work and
the tip of my finger popped in and slid straight to the second knuckle.

"Yeow!" he let out, "not so fast!"

I left the finger where it was, just slightly turning it, "Sorry buddy, the
lube made it too easy, I'll take it slower." I started a slow in and out
stroke with the first 2/3rds of that finger. I lifted his hips slightly off
of the pillow then added some lube to my left hand, I started giving him a
slick, squelchy hand job, squeezing and pulling his dick like it was an
udder.  Robby was already heated up, laying his head flat, ass high, and
basically panting. Eventually I reached full depth with my finger, and left
it buried while twisting it around and pulling on the walls of his warm
rectum.

"Time to try something else," I said, slowly sliding my finger out, causing
his hole to clamp back down. Robby popped up onto his hands to look back,
so I held up the rubber dildo made of beads. It was very long, so Robby
looked a little fearful, "you only go through a few beads pal, I'm not
sticking anything a foot inside you. Remember to stay relaxed and
everything will go 100 times better and feel 1000 times better," I added as
I lubed up the first 5 beads.

"I want you in a different position for this. Lay on your left side flat on
the bed, you can put your head on the pillow if you want." Robby did as he
was told, "Now let me move your right leg up," I bent his knee and brought
the leg in front of him, causing him to roll slightly toward his
stomach. "This position lines everything up inside you, so that if
something is a little longer, it won't be uncomfortable." Robby seemed to
take it at face value, and just laid his head down, closing his eyes as he
waited for me. "That's perfect," I said, stroking his side and ass cheek.

Spreading his cheeks with one hand, I grabbed the lubed up beads. They
started very small, much smaller than my finger, so it would be awhile
before anything caused discomfort. Bringing my fingers to each side of his
asshole to spread him open, I began to insert the flexible bead line. The
first couple popped in without comment, but as I slowly pushed the third
in, Robby gave an "umph" sound.

"Doing ok?" I asked.

"I'm fine, it surprised me," he said flatly, "it feels funny when it goes
in." Funny is better than bad, I thought.

"I'm going to go in and out with that one a few times," I told him.  He
just grunted. I slowly pulled the last bead until it pushed his sphincter
open, slowly widening it as it came into view, then popping out as his lips
closed behind it. I added a little lube to the bead, then began pushing
back in. Watching the tight lips spread as the bead pushed in was a sight
that I'll never forget. Robby had begun to let out a mixture of a sigh and
grunt when the bead slid in, and a squeak when it came out. We repeated the
cycle a couple more times before trying the next bead.

The forth bead still went in easily, but got a nice groan out of
Robby. Again I slowly pulled it back out, then watched his hole expand
wider as to take it back in. The next bead was wider than the smallest
dildo that I had, so I planned to switch if he could handle it easily. With
another dollop of lube, i increased the pressure and watched his ring widen
again, with little reaction from him, the fifth bead slowly slid through
the muscle until it snapped tight around the backside trapping it inside of
him. Robby moved his legs around to get in a more comfortable position, so
I decided to help him roll onto his back. We used the pillow again to angle
his hips up, displaying the obscene scene of the sex toy dangling out of
his tight eleven year old ass, his prick standing stiff above, "Oh my god
is that hot," I moaned, causing Robby to lift his head and look down
between his legs and smile.

Using more lube, I started jacking his cock. He lay back again and started
squirming, lifting and lowering his hips. Then I began to pull out and
reinsert the last bead, causing him to lift his legs, giving me more
access. Still moving slowly, I pulled all of the beads out, then back in,
while I grabbed the smallest dildo. For the last time, I pulled the beads
slowly out all of the way, and saw his anus quiver then shut after the
smallest bead left. I used the lube already on my left hand as well as the
coating around his asshole to insert my index finger straight into
him. Robby gave out an "ooh," sound but then settled back down.

With my right hand I poured lube over the dildo, then spread it all the way
around it, coating the whole thing. At the same time I was fucking Robby
with my finger, pistoning in and out and twisting my finger. On one out
stroke, I brought my middle finger next to the index and slowly let it
slide in. Robby gave several uncomfortable grunts, but the two fingers slid
home until they were fully buried. I hooked them upwards to get into
contact with his tiny prostate and that caused a new set of leg kicking and
"ahh"ing. With the dildo at the ready, I removed my fingers and followed
immediately with the sex toy. With all of the lube and stretching, the
silicone dick slipped right in, so I immediately began fucking his ass with
it.

Robby took to this anal play so readily, that I decided to move onto the
next step. I brought his hand down to the plastic cock and encouraged him
to continue the thrusting. He latched on, and actually increased the speed
of the insertion. With this amazing visual, I began lubing the smaller butt
plug. It was shaped like an upside down light bulb, with a flat base to
keep it in place. The whole top was designed to stay implanted inside his
ass.

Taking the dildo back from him, I slowly removed it, followed by
introducing the narrow, rounded tip of the plug. It immediately flared out,
until it became the widest toy he had taken thus far. Robby bore down, and
had to be reminded to relax. "You can try pushing out, sometimes that opens
you up a little," I coached. His hole began to slowly slide open, stretched
over the ever widening toy. As his ring stretched open across the widest
flare of the toy, it slipped in, his ass pulling it in as his hole closed
around the plug, the handle settling into his crack.

Robby gasped, then shifted his legs and butt, trying to get a comfortable
position. "How does it feel?" I asked

"Full," he answered, "not bad."

"Do you want it out or do you want to try keeping it in for a few minutes?"

"Let's leave it in," he said, "see how it goes."

His cock was as hard as a rock, and I couldn't resist taking his slim penis
back between my fingers. Robby bucked his hips up to meet me, and seemed to
squirm and rotate with the small plug stuffed up his ass. Lots of little
moans and yelps escaped his lips, and he quickly approached an intense
climax. Sensing that he was close, I took hold of the plug, ready to slide
it out to avoid discomfort after his peak, at the same time applying
pressure and motion to the toy. The added stimulation was all that he could
take, and his little dick began to rhythmically pulse in my lubed up hand
as his orgasm overtook him. Slowly I eased the plug through his ring as he
road out his climax, letting out a yelp as it slid past the widest point.

I lay the plug next to us, and took slow strokes along his wilting cock and
balls. When he started to jump at the contact, I let him rest, but gently
pushed his legs back up to look at his anus. His ring was gaping, randomly
opening and closing slightly. The gape surprised me, and made me realize
that real sex was only a matter of time.

I let his legs rest back on the bed, and crawled up to give him a quick
kiss, "That was great," he said, "I like that one," he added, gesturing to
the plug.

"You really took it well," I answered, "I think that you and I are going to
have some great times this week! You should have seen how wide your hole
got. When you want, there's no reason that you couldn't take me inside
you."

Robby considered, and gave me his "I don't know about that" sneer, but with
a quick lip bite that gave me hope.

He had to get going, so we cleaned up, and I sent him away with his plug to
try if he wanted, with a caution to use lots of lube, we didn't need him
hurting himself and needing to seek help!


Chapter 11

The plan for the rest of the day was for Robby to spend the evening with
his family, pretend to go to the kids club for a sleep under, then swing by
my room around 9.

I spent the evening exploring the ship, doing a bit of gambling, and
grabbing a quick meal. Otherwise, I was mostly occupied with counting the
minutes until I saw Robby again. Even though I had cum with him earlier,
our time had been mostly about him, and my orgasm had just been a release
of the built up tension from the past weeks anticipation. So I was still
ready for a long session with my sexy boy.

Shortly after nine I heard a soft knock on the door, causing me to jump up
and let him in before someone noticed a pattern here. Luckily I wasn't in
the type of room that had a "butler" monitoring the comings and goings of
my room. Robby popped inside, and fell into my arms.

We waddled over to the bed and I lay him back, leaning over him and
bringing our lips together, "How was your night?" I asked between smooches.

He put his hands behind his head, "Fun. I spent some time at the club and
met a kid my age. But he's not going tonight, so I don't care that I'm not
there," he added.

"I'm glad that you had a good time, and more glad that you came to see me!"
This respite couldn't last for me, I was already hard just being in his
presence, and needed him to please me. I ran my hands under his shirt,
rubbing from his belly up to his soft chest, then leaned back in for a
kiss. He took my tongue between his lips and wrapped his hands around my
neck, pulling me as close as possible. I rolled us over, pulling him on top
of me. Grabbing his ass, I began grinding my cock into any part of his body
that I could reach. My shorts were loose elastic, and I reached down and
hooked the elastic under my balls, leaving my naked cock pushed against
him.

My little head was taking control, and I applied pressure to Robby's
shoulders, encouraging him downwards while we broke our kiss. With a smile
he wiggled his way down my body, rubbing himself against my dick from his
crotch up to his chest as he went. When he was met with my penis face to
face, he grabbed on and stroked me, no hesitation. With his other hand he
worked my shorts down over my ass and I helped slide them all of the way
off. The freedom of being naked below the waist caused me to spread my legs
wide, letting him lay on the bed between them, leaving me completely spread
before this beautiful creature.

He continued to stroke, looking up at me with an evil grin as he watched me
squirm. Not able to take it any longer, I used my hand to guide his head
closer to my cock. He took the instruction and started with a long lick
from the base just above my balls all of the way to the tip, then twirled
his tongue around the tip, taking any precum that was spilling out. "Oh god
baby," I moaned as he returned to the base and started to lick my balls,
causing me to spread out even more and hold his head down there as the
rough sensation of his little tongue bathed across my whole sack. I reached
down to lift my balls and he didn't hesitate to drag his tongue along my
perineum, sending a chill up my spine. My need was rising, so I grabbed him
under his arms, pulled him up to face me, started making out again as I
flipped him over so that he was beneath me.

We broke the kiss and I pulled my knees up until they were under his
armpits, leaned on my left hand above his head and used my right hand to
guide my cock back between his red lips. Full of passion, the time had come
to take charge, and I started fucking his mouth, sending my pleasure
through the roof. He struggled slightly to keep up, but made no effort to
escape as I pumped into him. It came to a boil quickly then, as I started
to moan with each thrust, "I'm cumming!" I shouted, and after two more
thrusts across his tongue, I froze as my orgasm slammed into me, unloading
into his mouth. Robby's eyes widened, but he took the first blasts right
into his mouth before it was too much and he pulled me out as the next
shots hit his face, running down his cheeks to join the semen spilling from
his mouth.

The last spasms hit me, and Robby pushed most of the cum out of his mouth,
but no gagging, then he closed his lips and surprised me with a swallow! He
was a mess, cum dripping down both cheeks. I used my hand to wipe it up,
then got up to seek out a towel. "You swallowed!" I announced as I came
back wiping my hands off, " was it better than before?"

"It was alright," he said, "it's definitely growing on me. I get excited
when you're excited, so it makes it more fun and makes me want to taste
it."

That statement made my dick twitch and start to harden slightly. But it was
Robby's turn, not that I would stay soft pleasing him!

"I get excited when you do too, buddy," I said, then pulled him by his legs
until they were over the edge of the bed and he was laying back. I grabbed
a pillow for his head, then when down on my knees and started sliding off
his shorts. Robby lifted his hips to help me slide them off, and I hooked
my fingers inside to take the underwear with them. His erection popped out
of the waistband, pointing back up at his face with the firmness of solid
steel. Sliding the shorts and undies off of his feet, I reached back up to
grab his rod, but caught a glimpse of plastic peeking out from his butt
cheeks. "What do we have here?" I asked rhetorically, "someone has been
playing," I added as I touched the buttplug.

Robby giggled while biting his lip, "It was pretty easy, andI I like that
no one knows that it's inside me!"

I reached back up and grabbed his dick, "You're a naughty boy," I said with
a smirk, drawing out a smile as I jerked him. After a few strokes, I leaned
over to give the head a few licks, then took him to the root. A sigh
escaped him, and he sunk back into the bed. I used a slow pace, no sense in
finishing this too soon, as I slowly slid up and down his entire length,
using lots of tongue in the underside and tip. At the same time I reached
back and took hold of the plug, gently working it side to side. I wasn't
sure how easily it would come out.

After a minute or so of slow sucking, I switched to his little pouch while
stroking his hard cock. I loved the tough texture of his ballsack when he
was retracted, feeling the firm folds against my tongue until I had warmed
him up enough for his balls to descend and loosen the skin. This let me
take one nut at a time wholly into my mouth, bathing it with my lips and
tongue. Then I moved down to his taint, moving his feet up onto the bed to
give me better access. In short order we arrived at the wrinkled gateway to
his tunnel stretched around the narrow neck of the toy. "I'm going to take
it out," I told him and he just nodded, not even tensing up.


"It will be ok," he answered, "I've put it in and out a few times today,
I'm used to it."

Imagining that activity caused me to stiffen significantly. I returned to
his pucker and did my best to tongue the stretched asshole. Wiggling the
plug gently, I began to pull and his ring started to stretch. Checking
Robby's face, I saw no distress, and even heard a few moans. As the plug
withdrew his wrinkle stretched impossibly wide as the wide base emerged,
then slid down the reverse flare of the head and it popped out, leaving a
wide gaping hole. "Oh man are you stretched out!" I blurted out in
shock. His hole was easily wider than my shaft, which is the first place my
sick mind went, "I could slide right into you you're so wide."

Robby sat up slightly and reached between his legs to touch his hole, "oh
man, did I hurt myself?" he asked worriedly.

"No baby, you just relaxed your hole. It will close back up, but having it
relaxed is good for us to play." I leaned in to take a closer look as his
hole started to close up, but he was still open enough that I could see
inside and see both sphincters. Stretching out my tongue, I gently licked
around his ring and made my way inside his gorgeous asshole. His wrinkle
closed around my tongue tip, but I was able to keep that tip inside and
stroke in and out and around inside of his sphincter. Robby was squirming
above me, obviously loving the analingous.

Finally sliding my tongue out, I licked my index finger and began sliding
it easily into his hole while I returned my lips to his unbelievably hard
shaft. He had taken the finger so readily that I switched back to sucking
on my own middle finger, slathering it with saliva, then brought it
alongside the finger in his ass on an outstroke, holding them tightly
together and twisting them into his hole. Robby winced once and let out a
gasp, but then relaxed as the two fingers slid all of the way into his ass.

Working my fingers as I sucked him off, I could tell that Robby was getting
close as his legs kicked, hips thrust and moans and groans peaked. I rubbed
the fingers up against his immature prostate and Robby cried out as his
shaft began to spasm and a sweet fluid shot across my tongue. After a few
slow licks, I released his shaft and slowly withdrew my fingers from his
butthole. They came out clean, surprising me. I had a discarded towel next
to us, so used it to wipe the fingers off, then moved up on the bed to lay
next to Robby.  He had his eyes closed and looked blissful. I just lay and
stared at his cute face. Eventually he opened his eyes and looked at me
with a smile, "That was intense," he started, "having your fingers in me is
way better than the toys. They're warm and alive!"

"I have other living parts of me that would fit nicely in there."

"You're a pervert!" he said, "that's all that you think about."

"Can I help it that I find you so sexy that all I can think about is being
with you? That's not a bad thing, and let's face it, you like having things
in your butt, and it's definitely been open more today then it would ever
be with my cock. You just have to decide that it's what you want." Robby
was giving me a bored look that I couldn't figure out, but then I noticed
that he was starting to get a boner.

"Let's do it," he said.

"What? Now?" I asked.

"Yes, I want it, and I can do it. I'm ready, it's ok."


I didn't know how much to question. After all of my nudging, now I was
worried that I'd talked him into something that he'd regret. "Sweety, you
don't have to do this, I'm sorry if I've made you feel guilty."

"You haven't, I really want this," he grabbed my semi-soft rod and gestured
with it, "I want to feel this inside me," he said then began stroking me to
hardness.

"Ok, look, I want this more than anything, just please don't do something
that you'll regret, ok," I asked, "and I'll stop asking if it's ok."

"Cool, it's ok," he said, then leaned down and took my cock into his pretty
mouth. I gave up resistance, and vowed to enjoy this experience. I helped
Robby spin around and pulled his renewed boner into my mouth. He was again
as hard as nail and I soaked his cock with spit before working to his balls
before moving up to reach his hole. As I dragged my tongue across his
pucker it actually loosened, giving me purchase inside. This seemed to turn
Robby on, as his work on my cock went into overdrive, pausing to lick
across the head or even reach down to the topsides of my sack before diving
back down, taking me to the edge of his throat with rapid strokes.

Bringing some fingers into play, I lubed up my fingers and brought them to
his loose hole. He was opening right up for me. Before he sent me over the
edge, I stopped licking his taint and said, "Baby, I think that you're
ready." He brought his head around to smile at me, and then rolled off of
my chest. "Lay on your side away from me," I instructed him. I was going to
need to be in charge of this to ease Robby's mind and let him savor the
experience without having to worry about what to do. I lubed up my dick
liberally, then took his top leg and bent it up toward his chest, opening
his ass to me.

Touching his hole, it still was relaxed and I easily slid three fingers in,
proving that it was finally time. All of the prep leading up to this giant
moment had kept the significance from hitting me, but as I lay next to this
sexy boy, preparing to line myself up with his asshole, the realization
that I was going to fuck an 11 year old boy smacked me over the head and I
couldn't hold myself back. "You're wide open for me beautiful, I'm going to
try to put it in, ok?"

"I'm ok," he answered. Moving closer, I opened his cheeks, shifted his ass
to lean slightly toward the bed, then brought the tip of my rod to connect
with his ring. With all of the lube, his asshole didn't resist me at all,
sliding over the head of my cock and enveloping me in his tight hole. The
sight of my cock stretching his hole mixed with the slick sensation of his
ass was mind blowing!

"I'm inside you sweety!" I said, before pushing more of myself into him,
getting no resistance from his inner sphincter. Robby let out a grunt as I
slid further inside, then an "oof" as I sunk deeper. After about half of my
shaft was inside, I backed off and took an in and out stroke. Feeling no
resistance, I was able to sink more and more shaft with each stroke. Robby
let out small squeaks with each in stroke and a moan with the out stroke,
"are you ok?" I asked while continuing the rhythm.

"Ooh," he let out as I sunk three quarters of my shaft into his welcoming
ass, "how far are you in?"

"I'm almost all the way in you."

"Uh," he said as his breath was forced out of him, "its good, I'm ok," he
spit out quickly. I had continued to fuck him, an inch more shaft going in
each time before finally, taking a last deep stroke, he took me all of the
way inside and my pubes pressed up against his soft ass. He twitched a bit
with this last inch of cock, and let out an "ah, ah," as a small bit of
pain hit him.

"I'm all of the way inside you," I said, "you feel like heaven baby." I
wrapped my arms around him and Robby felt behind him to prove to himself
that he had done it as I held myself fully inside. "I feel so connected to
you."

"It hurts a little, but good," he told me. I pulled out and slowly sunk
back inside and received a familiar grunt from Robby. Starting a steady
rhythm, I pushed my upper body away so that I could watch myself stretching
his tiny hole. I picked up the pace and Robby started squirming and
moaning. Staying inside, I put some pressure on his shoulders to encourage
him onto his stomach. We rolled together until I was hovering over his
prone body between his spread knees, still half impaled by my cock. Slowly
I slid back in to the hilt and Robby responded with a twitch and louder,
"ah, ah," sounding a little more like he was struggling.

This position seemed like maybe a bit too much, so I pulled him up by the
hips until his knees were under him, while he left his upper body collapsed
on the bed with his arms stretched out in front of him. I cupped his
delightful, chubby butt cheeks as I resumed fucking his velvety ass. This
position was easier on him, and his moans returned as "oh's" and "ooh's" as
I again sunk fully into him until my pubic bone was pressed between his
cheeks, sending shivers up my spine. We started a gentle pace, with Robby
even pressing back to me on the in stroke, seeming to enjoy the whole
experience.

This slow fuck was sending me over the edge, but not wanting it to end yet,
I pulled out of him for the first time. Robby let out a shocked groan and
dropped onto his side. I pushed on his upper leg to encourage him to
continue to roll onto his back. He looked up at me with glazed eyes as I
pushed his knees up toward his chest. His cock had shrunk into a tiny hose
above his loose balls. Surprisingly, his ass ring had returned to a normal
size, not gaping open. In order to let me cool down slightly, I leaned
forward and brought our lips together in a passionate kiss. Robby grabbed
me behind the neck and pulled himself up off of the bed as he thrust his
tongue into my mouth seeking me out. He was so passionate that he was
letting out muffled "mm's" as we made out.

This wasn't having the cooling off effect that I had planned, so I broke
the kiss and rocked back until I was sitting on my feet between his
knees. I pushed his knees back up toward his chest while bringing my dick
back against his hole. With a couple of runs across his asslips with the
spongy tip, his hole actually loosened again and opened slightly. I applied
slight pressure and easily began to slide in. Robby's eyes were shut tight
as he braced for the new intrusion into his most private place. As I slid
further, his lips parted, his tightly closed eyes relaxed, and he let out a
long moan until I was once again completely inside him. Again we started
into a rhythm as Robby rotated his hips to get more comfortable. I grabbed
his thighs to pull myself into his ass.

As I sat back toward my heels, I took hold of his shrinking worm. It gave
no response, but Robby reached down and began fondling himself, so it must
have felt good. Stretching my legs out from their squatting position, I put
Robby's knees behind my arms and began thrusting harder from this prone
position. Robby was gasping and crying out with each thrust, and I heard my
own voice blurt out a series of, "oh gods," and, "yes's," as the strokes
sped up and I started pounding into his upturned anus. Barely registering
how well Robby was taking his first try at anal sex, I leaned forward and
again began kissing him. He immediately grabbed onto my neck and pulled his
upper body against mine. I brought my right arm around him to hold him to
me as I balanced us with my left, all the while slamming into him. The
tight ass, beautiful boy and delicious mouth were too much and I was sent
over the edge with a loud, "Oh baby, I'm cumming inside you," and pressed
my groin tight against his ass as I unloaded what had to be a torrent of
semen deep inside his ass.

Frozen in place for a few seconds, it was suddenly silent as I finished
spending my load, the only sounds were our panting breaths and occasional,
"oh," and "oh man." Then I lowered Robby back onto the bed and carefully
withdrew, this time his ass gaping open after his long first fuck.

After I pulled out, I dropped onto the bed, pulling Robby against my
side. He lay across me, his head nuzzled against my neck, his right leg
pressed along my side, his left thrown across me, smashing his soft prick
and little balls against my upper thigh, and the back of his left thigh
pushing down onto my spent, lifeless and equally soft cock. Robby was
giving me small kisses on my neck as I rubbed his back with my right hand
and held him close with the left. I let my hand wander to his butt, and
dipped my fingertip into the cummy mess down there. Robby held onto me as
if he couldn't get close enough, occasionally shifting his groin and legs
to regain purchase on top of me as he pressed his lips to me over and over.

No post-coital glow had ever felt like this in my life, male or female, The
passion from this sweaty little boy was palpable, as he squirmed against
me, pressing every possible inch of his body into contact with mine.

I diddled with his well fucked hole, feeling it close up slightly as he
recovered, my cum oozing out occasionally. Eventually he popped his head
up, lifted his body slightly and put his hand on his stomach. "You may
feels cramps, it's a good idea if you go let my cum drop out of you into
the toilet," I said, guessing his predicament. He got up gingerly, grabbed
his cheeks together, and started shuffling to the bathroom, his other hand
holding his tummy. I got up to follow, but before I even got there I heard
the bowel sounds as he expelled any left over contents. I watched him for a
second, his grimace relaxing, "feel better?"

He nodded his head, "yeah, that came out of nowhere."

"It's your body reacting to something being inside. It feels the cum and
eventually tries to get it out. Everybody reacts a little different. I
should have had you come empty out right away, I just couldn't not snuggle
with you," I said with a poke to the ribs. Robby giggled then looked up at
me with glazed eyes, a goofy grin on his face. He reached over and grabbed
my hand, pulling me closer to him while he sat on the toilet, slowly the
gap closed between us and our lips met in a loving series of kisses, pecks
and occasional open mouthed tongue duals.

Robby let out a loud wet fart that echoed in the small room, causing us
both to laugh out loud. "Feel like you're done," I asked. Time had gotten
away from me and Robby was expected back in ten minutes, "we need to get
you back to your room."

"I feel like it," he said. He wiped up any left over mess and got up. I ran
a shower and quickly rinsed his body and ass off, trying to quickly get any
left over semen. We did a quick towel dry, then pulled his swimsuit and
T-shirt back onto him. Fully dressed, I held him in my arms again, his head
against my chest, arms wrapped around each other, holding tight as Robby
softly breathed against chest, again trying to melt into me.

"This was the most amazing experience that I've ever had buddy," I said ,
rubbing the back of his head, "thank you for giving me the gift of
tonight."

Robby lifted his head, glassy eyes looking up at me, "I loved it, I love
everything that we do."

We shared one last kiss, then said our good nights. I sent Robby away with
a swat on the butt. As he closed the door, I couldn't help think about the
fact that I was sending this kid home with a belly and ass full of my
cum. "My boy," I thought, almost like a possession, as if I had marked my
territory. I knew better, but the connection that I felt that night was
like nothing that I'd ever experienced, and I couldn't wait to see my boy
again.

Chapter 12

I felt great the next day. Relaxed and satisfied, on top of the world. It
was fairly early, so I decided to go out by the pool and read before the
crowds picked up. Since I was seeking shade instead of sun, the seats that
I wanted were wide open at this hour. All of the sun seats were being
commandeered with towels and beach bags as people headed to breakfast. I
settled in and started a new book, sipping a latte, feeling great. It was
about 15 minutes later that I noticed motion in my seating area. I didn't
pay much attention, until a towel was thrown onto the chair next to
me. Glancing up, I about had a heart attack when I saw that Robby's sister
Sophia was setting her stuff on the chair next to me!

My breath caught, and I quickly looked away, I'm sure turning bright
red. Looking around, I realized that there must have been 10 empty seats
around me, "what the fuck!" I thought. I felt a full on panic attack
coming.

Pretending to read, I finally glanced up over the top, hoping that my
sunglasses would hide my gaze, and slowly tried to look her way. She was
starting right at me! It made me jump slightly. Couldn't have played it
less cool. Looking me right in the eye, she spoke, saying, "How did you
like fucking my little brother?" I'm sure that I turned white as a ghost,
choked a little, then looked around us to make sure that no one heard
her. There wasn't a soul around.

"What did you say?" I finally found my voice.

"You heard me," she said, "I know who you are. You hang out at the pool at
home. I knew something was up when he was trying so hard to be alone, it's
not really like him. And I saw you go to the bathroom with Robby at the
buffet. So last night I followed him and saw him run into your room with
you. Then this morning, I thought that he had dried toothpaste on his face,
but realized it wasn't likely way over on his cheek. It didn't take a
genius to figure out it was dried cum." My eyes had to be the size of
saucers, "Then I saw his swimsuit laying on the bathroom floor, and guess
what? Same crusty stuff on the back of his suit. Not a lot of guessing
needed to figure out how that got there."

"Kid, I don't know what you're talking about," I started.

"Don't worry, I don't care. He can do what he wants as long as he's
happy. And we can help each other," I stared at her in silence, "you need a
way to be alone with him, I need a way to be alone with a man that I
met. Robby isn't the only one who likes grown-up cock. So this is what we
do; he starts staying with you at night, then I'll text him when it's safe
to come back in the morning. My mom never just stops by, she texts about
breakfast, so we won't be caught. Even if she came by, I could say he took
a walk. Today she knows that he's sleeping in because he's so tired from
his sleep under," she made air quotes with her fingers while she rolled her
eyes at me, "you must have given him quite a workout, he's dead to the
world."

I couldn't have been more stunned. What she said wasn't sinking in, the
only thing that registered was how accurately she figured out the things
that could send me to jail! "I don't know who you're talking about," I
tried again.

"You have an easy decision," she went on, ignoring my plea of ignorance,
"get exactly what you want, or live in fear of what I might do with this
knowledge." This was a pretty savvy 13 year old. I shouldn't be surprised,
knowing her brother so well.

"Ok," I said flatly, fessing up and agreeing at the same time.

"Great," she said, "you just made two kids very happy!"

"How did you figure this out?"

"I remember you from last year, I hoped that you were interested in me,"
she said, "you didn't seem gay to me."

I leaned closer, "I'm bi, I was married before. The truth is, since
everything is out in the open, I'm mostly a bisexual pedophile," it felt
weird to say that out loud, "but I do prefer boys. Which doesn't mean that
I don't have feelings for young girls."

She gave me a look over and said, "So would you like to have some company
this morning?"

"I don't think that your brother would love that idea," I answered, not
really taking her seriously.

"He would never know, and I'm a lot more experienced," she said with a wry
grin.

I couldn't help look her over. She was still the same girl as last
year. Though she had leaned out a bit, she was still chubby, wearing a too
tight bikini being stretched by he pudgy belly. She wasn't overly developed
for her age, not having huge fat girl breasts, still sporting smaller
mounds. Was I better than this? I had just fucked her brother 10 hours
earlier, was I really considering risking his feelings, and my safety, by
messing around with his sister?"

"And I'm on the pill," came out of nowhere, "you could cum inside me, just
like you did to my brother."

"How many times have you done this?" I asked, not believing her confidence.

"Not enough. And I haven't gotten anything since we left port. The last
time that I screwed around was a kid at home a few weeks ago, and he's just
a boy."

"How many men have you been with?" I asked.

"Just two, and only one fucked me," she answered, "and a few boys."

I looked around, the chairs were starting to fill in, this conversation
wasn't going to be ok for long, "We can't keep talking about this, let's go
to my room and we can figure some stuff out."

She smiled, "You lead, I'll be there in a minute, I know where your room
is."

If I wasn't going to screw around with this girl, bringing her back to the
my room wasn't going to make that easy. But now that the cat was out of the
bag, we needed to work out some logistics. I gathered my belongings without
saying anything else, and headed out, ignoring her, knowing that not a lot
was going to stop this kid. When I got to the room, I left the door open,
similar to the first day of the cruise, sitting on my bed, just waiting for
a different guest.

She arrived not 30 seconds later, a pool towel wrapped around her, and
closed the door and locked the latch. I tried to steer us toward a cleaner
(at least in the immediate situation) discussion on how we were going to
get all of the pieces together so that everyone could get laid, "So we have
to work out how to work out the night," I started.

"It's simple, he comes here after dinner and comes back for breakfast," she
said with exasperation in her voice, "I want to talk about now," she said
with lust in her voice. She dropped her towel, showing off her
underdeveloped body, then shocked me by grabbing her bikini bottom and
pulling them completely off, standing in front of me in just her bikini
bra. Her pussy had a lighter coating of pubic hair than I would have
imagined on a thirteen year old. The lips were still hidden between her
closed thighs.

"Oh my god are you sexy," came out of my mouth before my brain could stop
me. She smiled and walked over to me, then made me jump when she bit her
lower lip, reminding me of her brother, I had a moment of guilt, but before
I could reconsider, she had closed the distance and jumped into my lap,
forcing her lips to mine. We fell into a passionate make out, and I ran my
hands up and down her back, stopping at her bathing suit strap. It was easy
to unsnap, and she leaned back hunching her shoulders and letting the
straps slide down her arms, exposing her little tits. They were two sexy
handfuls with stiff nipples that looked like over sized erasers poking out
of quarter size areolas. I groaned at the sight, and flipped her over onto
the bed. I kissed down her neck, massaged her breasts while I kissed and
licked my way around the tops and base of her tits, licking under her tits
where they met her body, then making ever tightening circles until I got to
her nipples, taking the first into my mouth and suckling, causing her to
start moaning and groaning, while she held onto the back of my head,
holding me to her chest. I switched sides, then worked my way down.

I moved across her stomach, dipping my tongue into her belly button, then
dragging my lips and tongue into the grooves between he pubic hair and
legs, her musky aroma working its way up to my nostrils. With a tiny bit of
pressure from my hands on the back of her legs, she lifted them up and out,
opening her young pussy to me.

It had been a long time since I stared at a vagina, and then it had been a
grown woman. This was a sight of beauty, the outer lips swollen and
opening, and with a slight pull from my fingers, exposing her wet inner
layers, and the hole in the lower middle. I dove in, holding her open,
licked from the hole up to her clit, pressing my tongue against the top of
her clit and rolling it side to side, eliciting squeals and screams from
her. Then I went back straight into her hole, extending my tongue as far
inside her as I could get it, while using my thumb to roll her clit. Her
pussy was so wet, pouring out her tasty, girlish nectar, so different from
a grown woman. My tongue went so far that it began to hurt me where it
attached to the bottom of my mouth.

Finally I put my fingers to work at her hole, slowly inserting my index
finger inside of her tight young pussy. My tongue went back to work on her
clit, while I began a steady fucking motion with my finger inside her
tight, warm, moist pussy. She was rolling her hips in time with my thrusts,
and I was quickly able to introduce another finger. After continuing to
buck against my hand for another thirty seconds, she asked in a stunned
voice, "Do you have two fingers in me?" I stopped my work on her clit to
let her know that I did, then went back to work while she dropped her head
back.

Her peak came quickly, as my fingers plunged in and out at a rapidly
increasing pace and I pushed back and forth on her clit as fast and as hard
as I could, alternating with sucking it into my mouth like a miniature
cock. She started bucking her hips up to meet my fingers, moaning and
repeating, " Oh yes!" over and over until finally she grabbed tight to my
head and held me in place as she let out a last "oh" and I knew that she
was cumming. I pushed my fingers in as deep as they could go and held them
in place as her legs twitched and shook, until finally she relaxed and I
slid them out to avoid over stimulating her.

She lay back as her body released all tension, but she grabbed my head and
pulled me up her body. She brought my face close to hers and started taking
breaths through her nose, smelling her scent that was smeared across my
face, "That was insane," she said, "nobody has ever done that for me," she
was still breathing heavy, "I can smell my pussy on you." She kissed me
with lots of tongue, tasting herself on my tongue. She reached down and
grabbed my cock through my swimsuit, "Take this off," she said, "I want you
to put it inside me!"

I scrambled out of my shorts, kicking at them as they got stuck on my
feet. I kneeled between her thighs, and looked over her, her spread legs
opening her wet pussy to me, her small underdeveloped tits exposed to my
touch. I ran my hand over her upper body, then held my cock in my right
hand, rubbing it up and down her pussy, spreading her lips and making a wet
squelching sound. She relaxed more and sighed as I centered my dickhead at
the entrance to her vagina and applied pressure.

I was immediately surrounded by a velvety, wet, squeezing tunnel that was
at least 4 times tighter than any pussy that I'd ever fucked. Still, she
yielded, allowing my cock to make a slow, steady inch by inch entry into
her. As I progressed, she let out a series of "oh ho ho ho" sounds. A combo
of pleasure, surprise and pain. She took my whole length in one steady
stroke, and when I bottomed out, I paused, pressing myself deep inside
her. "Oh my god, oh my god," she said quickly, gasping, "you're so big!"

I was surprised by her reaction, and wondered if maybe her experience was a
little bit of big talk. "Are you ok sweety?" I asked gently.

"Yes!" she almost screamed, "oh my god, it's so good."

I leaned down and put my arms around her, and brought my lips to hers. With
her small tits pressed against my bare chest, I pulled out about two inches
then slowly pushed back in. She broke the kiss and again let out a throaty,
"Oh god," and gasped with the new depth. Her vagina gripped me as I pulled
out again, it was the tightest pussy that I had even been in, but she was
so wet that it was easy to slide out. I started stroking about half of my
cock into her and she kept letting out the same half cries, "ah, ah, ah, oh
god!"

I pushed myself onto my arms and started fucking her with longer strokes,
then got up on my knees, pushed her legs back and started to really pound
into her. Everything that I did seemed to increase her pleasure. Her little
belly shook with each thrust, her tits moving in time.

After a few exquisite minutes, I pulled out. She gasped, and looked up at
me, "Roll over," I said, pulling her right leg over as I said it. I grabbed
a pillow and placed it out so that she could bend over it, and for the
first time remembered her brother in the same position last night. Her arms
were down on the bed with her ass propped up by the pillow, her glistening
sex opened up for me, her musky aroma filling the room. I lined up and slid
back inside her, pressing my pubis against her ass. She let out a sound
like an "umph," then said, "Oh, it's too deep" I backed off, thrusting into
her with shallower strokes. I leaned back and grabbed her plump ass as I
fucked in and out of her tight wet cunt. Again the view of her ass jiggling
below me reminded me of her brother.

I grabbed her leg and pulled her back over on to her side, leaving my cock
inside her. Holding her right leg up, I pulled the pillow out, placed her
leg on my shoulder with her left leg on the bed and started to pound away
again in this scissor position. She was almost completely limp, letting me
move her as I pleased, but still moaning, gasping and sighing, eventually
building to a high pitch that told me another orgasm was approaching. I
flipped her leg the rest of the way back over, getting us back in the
missionary position.

Again able to sink to the hilt, I lay down on top of her, shifted my hips
high on her so that I was grinding the top of my dick into her clit as I
thrust and fucked her by moving my hips while staying in contact with my
hipbones. She started to cry out, with some "oh fucks" and "yes, yes's"
repeated at increasing volume. I felt myself start to boil over and as she
froze in climax, twitching through her orgasm, I went over the edge,
slammed into her one more time and held myself tight, groaned loudly, and
unloaded deep inside of her, my whole body wracked by each surge of
ejaculation.

We were left panting, me still laying on top of her, both out of breath and
spent. Slowly I rolled off of her, my deflating cock sliding out and
leaving a slimy trail across her right leg. She was splayed out, arms and
legs still where they fell after her orgasm. The reality of what had just
happened came back to the surface, I couldn't believe that I had fucked two
underage siblings in one twenty four hour period. And they were absolutely
the two best sexual experiences of my life.

She finally turned her head to me and smiled, "That was something," she
said, continuing to smile.

"Something tells me that you haven't been completely honest about your
experiences," I replied, "have you really slept with lots of men.

Her eyes were downcast, "I let a 10th grader fuck me," she admitted, "and
blew a ninth grader on vacation last winter break. The rest were boys my
age, but those were nothing like this!" she added, "this is why I wanted a
man.

"You and your brother are something else," I said, "this has been the best
couple of days in my life."

"Didn't you do stuff at home?"

"We did a little, but we didn't fuck until last night."

"So who was better?" she asked.

"Totally different," I answered honestly, "it was his first time, so that's
exciting but makes things harder, I told you that I prefer boys, so he's
got that. But this was the best sex that I've ever had with a woman. You're
such a sexy kid, and you fuck like a champ." That seemed good enough for
her, as she smiled a little.

Just then her cell phone chirped, and she rolled over to lean off of the
bed to grab it from the floor. It gave me another view of her plump ass and
leaking cunt as she stayed like that while she typed on her phone, "It's my
mom, we're meeting for breakfast in ten minutes. I need to get going."

"You can use the bathroom to clean up," I said, "if you need to shower
quickly, go ahead."

She jumped up, and cupped her hand under her vagina, catching any of my
semen dripping out, and ran into the bathroom, closing the door. I heard
the toilet flush and shower start up. This wasn't the loving clean up that
Robby and I had enjoyed, she was a more experienced kid who'd taken care of
her needs and was able to take care of herself. It was kind of refreshing.

I laid on the bed naked, contemplating my good fortune for a minute, then
got up and put my suit on. The shower stopped after a couple of minutes and
she came out with a towel over her shoulder, accidentally giving me a last
view of her naked body before pulling her tight suit over her wide hips.

She offered to teach me how to use a disappearing text app, so that we
could communicate, which we set up.  "So I'll arrange it with Robby that he
stays here tonight, ok? I'll text you and let you know."

"That would be perfect," I answered, trying not to sound too eager, lest I
hurt her feelings, "you still going to meet your guy then?"

"Jealous?" she raised her eyebrow, "it could be you if you want," she said
questioningly.

"That wouldn't work, but you are tempting and I am jealous," I told her,
"thanks for a great experience."

She softened a bit, "You too," and headed out of my door.

Chapter 13

I'd love to be able to say that I felt guiltier than I did, but in reality
I felt only about 30% guilty toward Robby. The guilt was low enough that I
actually went to the buffet to spy on the two of them, since I was so
turned on by the idea that these kids were sitting eating breakfast with
their mom while my cum sat inside of them. The naughtiness was just too
much. After getting dressed and heading up to the restaurant, I saw them
almost immediately, but neither kid saw me.

After grabbing some food, I found a seat far enough away to not be noticed,
but gave me a clear view of their table. The distance allowed me to stare
the whole time, watching my conquests. Robby seemed antsy, I assumed from
the excitement of last night and the good nights sleep. His sister, on the
other hand, was slouched in her chair, relaxed with her legs spread open,
her crotch hidden by a cover up that she must have put on after leaving my
room. I was glad that I didn't need to worry about any wet spots giving her
away.

Staring at them, I realized that I needed to have a talk with Robby. I
wasn't going to admit my indiscretion, but we needed to lay out
expectations. I had real feelings for him, and didn't want to lose him or
hurt him, but he needed to know that I had a wandering eye, and it was
necessary because he wouldn't be 11 forever and we'll both be ready to move
on someday. Needed to figure out a meeting.

Her mom walked away, so I took the opportunity to message Sofia about
setting up a meeting with Robby, just to talk things over. I asked her to
have him meet me at an out of the way restaurant that served coffee in the
morning. It shouldn't be too crowded so that we could talk. We arranged to
meet just after breakfast, so I decided to head down. The restaurant was
designed for the dinner crowd, so I grabbed a table well away from anyone
else. The volume was quiet enough that we were going to be able to talk,
but noisy enough that we wouldn't be heard at other tables.

Robby appeared shortly after I got a table, a huge Cheshire grin on his
face. He was dressed for swimming, so that must have been his get away
excuse. He plunked down across from me, and I was struck by how natural it
would have felt to give him a kiss in greeting as if he was my
boyfriend. "Good morning," he chirped.

"Good morning, did you sleep well?"

"I did," he answered smiling, "I had quite a workout yesterday," he joked
while biting his lip.

"Everything feel ok after your `workout'," I joked back, "no sore muscles
or anything?"

"Everything is fine!" he said, "I'm kind of surprised, but I feel like I
could workout again right away!"

I almost did a spit-take when he said that, and my dick lurched in my
shorts, "That's very good news!" I told him lasciviously, with an
unmistakable leer in my gaze. He responded with his sexy lip-biting grin.

"So I asked you to come here because we need to talk about some important
stuff, and if you came by my room, I'd be too interested in working out." I
stated, eliciting an eye roll from my overuse of this new euphemism. "It's
important to me that you know how much I care for you and feel really close
to you," this drew a genuine smile, "but it's also important that you
understand that I won't stop looking at other people, and I can't promise
you that I won't do anything with someone else."

Robby lost his smile a little, and replied, "Its ok. I feel really close to
you too, but I know that we are having fun, not dating!" and gave a little
chuckle. "I haven't thought about it, I'm just happy around you, and you
make me want to do dirty things," he said in a lower voice, "that's enough
for me."

I was relieved that this went so well. I added, "I also understand that you
may meet someone that you want to be with, and that can be ok, it doesn't
have to mean that we can't be together, especially if you find someone your
own age that you want a relationship with. You and I can't relate like you
could with a boyfriend your age, You may still have needs that require
someone older to fulfill, or maybe teach you." He watched me without
reacting, "So I guess that I just want you to know that I still care about
you, still find you incredibly sexy, and will continue to, even if I look
at, or even play with, someone else. Can you understand that and be ok?" I
finished.

"Don't worry, I may look too!" he said with a laugh, "Its ok, I get it, and
I won't freak out if you play with someone else. I'd like you to keep
playing with me though."

"Oh, don't worry about that," I said, "I'm so turned on by you, you're
lucky that I haven't torn your clothes off."

"Remember that I like boys too, I don't mind sharing."

My cock lurched imagining this cutie sucking my cock with another
boy. "Then we're all good. Now we need to figure out how to see each
other."

"Oh, it's all set," he told me, "we are going to the captains dinner, then
I'm going to pretend to go to the sleepunder, and my sister will cover for
me the rest of the night. By the way, how did my sister get involved in
this?"

I panicked for a second, but realized that he had no idea what went on
between us. "She recognized me from home, saw a little white residue on
your face and shorts," I raised an eyebrow and Robby bit his lip, "and put
two and two together. She's helping us because she wants the room to
herself."

"Cool, then after I change, I'll come to your room tonight."

"Why do you have to change?"

"It's the fancy night, so I'm going to be wearing a suit."

This brought an incredibly erotic vision to my face of me fucking him with
just his suit pants pulled down and his jacket pushed up, "can you wear
your suit? The idea of you half in it and half out of it makes me excited."

He laughed, "I'll figure something out."

We finished up our drinks, and said our goodbyes until the night.


Chapter 14

I spent the rest of the day relaxing around the pool, working out and
enjoyed a nice meal, even though I skipped the fancy dinner. As the day
wore on, I returned to my room to await my little lover.

At around eight o'clock there was a soft knock at the door. I made no
pretense toward coolness, and jumped up, hustling to greet my boy. When I
opened the door, he was standing there, still in his suit from dinner as I
had requested. He was still young and chubby enough that his shirt was
pulled loose from his pants, but not out, and his slacks had slid down to
his hips. His face was pure mischief, and I stood aside to let him in.

As soon as the door was shut, he turned toward me and jumped into my arms,
mashing his face to mine in a deep, tongue-filled kiss. We made out as I
carried him into the room and dropped us both onto the bed. I was
immediately as hard as a rock, and both of us were thrusting into the
other. When I broke the kiss, both of us were panting, the excitement
spiraling out of control.

I took ahold of his hips and turned Robby onto his stomach, then pulled him
up onto his knees. His suit coat hung over his ass, so I flipped the bottom
half up onto his back. Rubbing his globes through the silky material, Robby
squirmed and pushed back against my hand. I hooked my fingers into his
waistband, and found that the belt was loose enough to pull down without
unbuckling. Pulling on alternating sides, I slid the slacks down past his
buttcheeks. He was wearing boxer briefs, and I noticed an unusual bulge in
his ass crack. Sliding his undies down under his ass, the largest butt plug
stared back at me. "Look who's all ready," I said with joy.

I was so excited to see him in this position, still mostly dressed with his
big, round globes sticking out. My fantasy from earlier today was coming
true.

Robby giggled at my discovery of the plug, "I thought that you'd appreciate
that," he said with a wicked smile.

I realized that we may be able to dive right in, so I loosened his belt and
undid his pants so that his legs could spread a little. I ran my hands over
his smooth cheeks, then took ahold of the plug and began twisting it
around, eliciting a moan from Robby. "Do you think that you're stretched
enough for me?" I asked, since both of us seemed to be overheating. "Im so
turned on, I want to get inside you just like this."

"I'm pretty stretched out, go ahead and try," he answered, wiggling his
butt a little, "I don't want to wait," he almost panted.

While twisting the plug, I started to pull out, and watched the incredible
sight of his asshole being stretched around the wide part of the buttplug,
then close back down as it came out with a squelch. He was glistening with
lube, so I slid my finger straight up his hole. He just sighed, no pain or
flinching. I knew then that we didn't need to wait and quickly unzipped my
pants and pulled my cock out. I had the lube laying on the bed, so I
reached over and squeezed a big glob into my hand and stroked it along my
dick, with a generous amount on the head.

"I'm going to put it in," I told him, "you sure that you're ready?"

"Yes, go ahead," his voice was a mix of lust and fear, "go slow," he added.

I lined myself up, and rubbed the head around his dilated hole. Robby let
out a "mmm" sound and his breathing became deeper. The view of his ass
sticking out of his pants and his dress shirt and suit coat pushed up on
his back turned me on like crazy. Something about taking this kid right
from a dressy dinner into my bed and not taking the time to disrobe made it
feel like some sort of fantasy. I felt like he had snuck up to his room to
be with me while a fancy party was going on at his home.

After teasing his hole for a few seconds, I put pressure right at the
center which immediately spread to accommodate the head. As I continued to
push, I slid in with little resistance, while Robby let out a half pained,
half joyful, "ho, oh, oh, ah," as my pubes hit his ass cheeks and Robby
offered no resistance as he let me continue to push into him and let
himself sink into the bed so that I was laying flat on top of him with my
complete weight on the boy. This was greeted with an "oomph," as we hit the
bed.

Robby's legs started spasming and shaking as he lay flat on the bed, a
sensation that went up to his asshole and squeezed delightfully around my
penis for several seconds until finally his whole body relaxed as he
exhaled and freed my cock from his anal grip. I stayed fully implanted up
his warm ass, loving the squishy feeling of his rectum, until I felt he was
open enough for me to start fucking him. As my first thrusts began, I
rolled us onto our sides for a more comfortable spooning fuck, when I
realized that the dress clothes had served their purpose and were now an
impediment to our coitus.

I let myself slide out of Robby's asshole and asked him to take off his
coat while I rid him of his pants and undies. I stopped him from removing
his shirt and tie, because I was still turned on by the juxtaposition of
his naked lower body with the fancy clothes. I turned him onto his back and
pushed his legs up to expose his hole. Under investigation his hole had
closed up, but easily accepted my finger. I had one hand holding back
Robby's right leg, while I guided my cock back to his hole and applied
pressure to his hole with the other hand. I was able to release my cock
once it slid past his asslips and push Robby's left leg back too, opening
him up to me and my cock began to slide back in.

When my pubic hairs were again pressed against Robby's cushiony cheeks, I
released his legs and leaned down to bring my lips to his and we started a
passionate kiss. After letting Robby get reaccomodated to my dick in his
ass, I began to slowly fuck him. He moaned into my mouth and let out
squeals and "umphs" each time that I bottomed out. His tight hot asshole
was the most pleasure-giving place that my cock had ever been.

As I picked up the pace and thrust harder into his warm hole, I began to
feel his dick poking into my lower belly. I separated from his lips, and
pushed myself up onto my knees, hooking my arms around his legs and
grabbing his prick with my right hand. I had come to realize that there was
little else that was as hard as a pre-teen erection. Stroking him quickly,
I was luxuriating in the steel hard under soft skin texture of his
beautiful cock.

The pace and force of my thrusts began to increase as I simultaneously
stroked his hard nail. Robby was becoming more and more vocal, letting out
loud "ohs" and "umphs" with each thrust interspersed with squeals. I was
afraid to ask how he was doing, but decided that I needed to protect him
from my basest instincts. "Are you okay," I painted as I continued my
assault.

He half yelled in a slightly pained way, "Yes, I love doing this!" That was
all that I needed and resumed my pounding. I wanted to switch positions, so
I pulled out and threw him onto his stomach, pulled him onto his knees, and
not so gently thrust my cock back into him doggy style. "Oh, god!" he
yelled as I resumed banging away, my body pounded into his ass making a
loud slapping noise as my abdomen hit his asscheeks and my balls smacked
against his taint. Then we moved onto our sides as I continued to fuck him
in a spoon position, allowing me to turn his head toward me and lock lips
as we passionately made out while I thrust into his rectum.

I was getting close to the edge, but didn't want to cum yet, so I slid out
of Robby, "I want you to try being on top," I said as I moved onto my back.

"Do what?" he looked at me questioningly.

"You get on top of me and sit on my cock," I told him, "just take it slow,
you're in control."

Robby pushed himself up, and put his knees on either side of my legs, but I
could see that he didn't have the height to be above my dick. "You probably
have to stand up," I instructed him, "then squat down." He got up on his
feet and began to lower himself. He still had his white shirt and tie on,
sticking to him in spots from sweat. I raised the front of his shirt so
that I could see him try to the insertion from this angle. He dick was
completely soft but he didn't seem any less enthusiastic about the act.

My dick looked huge compared to the young boy as i held it straight up for
him and he moved down to meet me. He instinctively grasped me as he lowered
his pucker onto the head of my shaft. Again he opened right up for me,
allowing me to luxuriate in the intense pleasure provided by his warm
hole. He somewhat clumsily lowered himself little by little, adjusting his
angle as he went, grimacing on occasion, letting out a few "Aye" sounds
when it became painful. Eventually his butt landed on my groin, and I was
once again fully inside the sexy boy. He stayed in place for several
seconds, panting and grimacing. When he seemed to relax slightly, I gave a
small upward thrust. "Move onto your knees now," I told him, "and lean
forward a little, it will feel better." He complied and his face relaxed
noticeably.

I started unbuttoning his shirt so that I could see our jointing, the
visual part being such a turn on for me. Robby helped by loosening and
pulling off his tie while he sat impaled on my rock hard cock, then helped
with the last few buttons and shrugged off his sweaty dress shirt. After
being so excited by fucking him when he was all dressed up, seeing him
completely naked upped the anti again. I grabbed onto his asscheeks and
encouraged an up and down motion. He quickly got the idea and started
fucking me at his own slow pace. It was just the break I needed to cool
down but stay completely stiff inside his warm ass. This relaxed position
was awesome for me, seeing his beautiful chubby belly, his limp little
penis, his ballsack flattening on my abdomen with each insertion, and the
appearance and disappearance of my penis as it smoothly slid in and out of
his relaxed hole.

I ran my hands over his sexy belly and up over his soft chest. I thrust
upward to meet Robby, which caused him to fall forward, his hands landing
on the bed outside of my chest. This brought his face much closer to
mine. I studied the look of concentration on his face until he looked up
and caught my eye. He smiled down at me in an almost embarrassed way, as if
I was disappointed that he had a dick shoved up his ass! I smiled back,
bringing out his naughty lip bite. I reached up behind his head and gently
pulled him down to me, bringing our lips back together. As our tongues
began to intertwine, I started to take over the fucking, holding him in
place while I thrust my hips up into his open ring. He moaned and squealed
into my mouth as we kissed.

As the speed of my thrusts picked up, Robby disengaged from my lips, but
kept his head lowered in concentration, and began to push back into me in
time to my thrusts. He was letting out low, excited sounding "oh's" with
each stroke, when I noticed that I felt his hard penis poking into my
belly. The realization that he was into this enough to have a hard on made
me double time my fucking, causing his "oh's" to increase in speed and
pitch, until it was a continuous staccato of high pitched, "oh, oh, oh,
oh."

His squeals paired with his active plunging of his ass onto my cock was
quickly bringing me toward resolution. I grabbed Robby in both of my arms
and flipped him onto his back, staying inside his hole. Once we were in
this missionary position, I resumed slamming into him, telling him, "I'm
going to cum inside you, I'm going to fill your ass up."

Robby answered with a loud, "Yes!" and reached behind me to pull my ass
into him, encouraging the ravaging of his little butthole.

The feeling in my balls began to rise, and I continued pounding while
Robby's vocal utterances continued to increase in passion and decrease in
intelligibility. I felt my orgasm coming upon me, and finally shouted, "I'm
cumming, I'm cumming up your fucking ass!" and froze, fully implanted in
his rear end, and unleashed what felt like a weeks worth of cum deep into
his bowels.

Robby was screaming too, "Yes, Yes," as I unloaded into him. I leaned back
enough to see his little spike spasming and a small bit of dampness appear
on the head. I grabbed ahold of his penis and gently stroked, keeping my
hand between us as I leaned down and kissed him hard, once again dueling
with our tongues. Finally I broke the kiss and slowly withdrew from his
anus, causing a sigh from Robby as I collapsed beside him.

"Oh my god, baby," I said, "that was unbelievable! Did you cum too?"

"I think that I did," he panted, "toward the end you started hitting
something inside me that made me feel so good! I couldn't control myself, I
just wanted more until I went over the edge when you were cumming."

"You are a pretty good bottom," I said, causing him to frown, "i think that
it's a compliment; you like the sensations that you get from having your
butt stimulated, that makes it good for someone who wants to help you get
those good sensations. It's a symbiotic relationship." Robby rolled his
eyes. Symbiotic must be in the sixth grade curriculum.

I lay stroking Robby's chest and belly, and occasionally fondled his wilted
penis and loose sack. "You probably should go to the toilet," I advised,
hoping to avoid the emergency cramps from last night. Robby hopped up,
holding his hand under his ass as cum dropped out and hustled to the
bathroom, followed by the echoing sounds of him emptying his bowels. He
returned to the bed and jumped on top of me. I stroked his back and ass as
he lay his head on my chest. He practically purred as I stroked his naked
body. This was the most comfortable, relaxed and satiated that I could ever
remember feeling.

After several minutes of wrapping my arms around my boy and alternately
stroking his smooth naked skin, I noticed that his breathing had slowed and
was much deeper. I cranked my head to try to see his face and realized that
he had fallen asleep laying on top of me. I chuckled to myself, and slowly
rolled him off of me onto the bed. He curled up into a ball in his sleep,
so I pulled the covers over his beautiful naked body.

I busied myself shutting off lights and setting an alarm to get him back to
his room in time before settling back into bed and pulling up the covers.
Again I wrapped my arms around the sleeping boy in my bed and held him to
my chest. In his sleep he grabbed onto my arms and sighed, breathing
contentedly. Soon enough, sleep overcame me as I basked in the afterglow of
this wonderful night and the warm smooth body of the naked boy in my arms.