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This work is copyrighted to the author © 2008.  Please
don't remove the author information or make any changes
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My Sexuality 5: A Well Needed Vacation
by Sassy Spank Meh (vicentevaltieri@gmail.com)

***

Part 5 of the My Sexuality series has Vincent enjoying 
a brand new boy whilst on vacation in Florida. (mm-
teens, mast, oral, anal)

***

George contacted me about two weeks after I started 
writing this saga. He and I were chatting over Instant 
Messenger, or as the children of today call it, "AIM." 
Our conversation went something like this (V denotes 
me, Vincent, and G denotes George):

G: "Hey Vin."

V: "Yo. Whats up?"

G: "Not much. You?"

V: "Not much at all..."

G: "Hey, I saw your story on the archives. Those sure 
were the good old days, huh?"

V: "Hellz yeah, man..."

G: "Hey, aren't you gonna write about that time Jeff 
and I got together?"

V: "Which time was this?"

G: "Oh...shit. Forget I said anything."

V: "Not gonna happen. You will tell me. Right. Fucking. 
Now."

G: Fine...I know what happens if I don't listen to you. 
It started off a couple weeks after we got back from 
Jeff's house..."

I had called Jeff up and asked him if he wanted to 
spend the night. He said yes, and sure enough, he came 
over within a half an hour. We killed time doing 
normal, non-erotic guy things. We watched TV, browsed 
the computer, played video games, and then ten o clock 
rolled around. We went back upstairs to my room, and I 
shut and locked the door behind me.

I reached down and undid the zipper on Jeff's shorts. I 
pulled his shorts off of his waist, and pulled his 
shirt up over his head. He did the same to me, and we 
sat there together: I in my boxers, and he in his 
briefs. We reached out to each other, and took off the 
other's underwear at the same time.

I went into the bathroom and grabbed a tube of baby 
oil, and I rubbed it all over my cock. Jeff bent over 
on top of my bed, and I shoved my lubed cock inside of 
him. God, did he feel amazing! I know why you loved 
that boy now!

V: "...I love him for the heart, not just the body."

G: "Er...um...yeah. Anyways..."

I rode him for a little while, pumping into him as 
quickly as I could. I shot off and pulled out of him. I 
laid down on the bed, and he came and laid next to me. 
I put my mouth down on his cock, and I started to blow 
him. Within about thirty seconds, he blew his load in 
my mouth.

We waited for about ten minutes, and then I stood up. 
He got up behind me, and then he grabbed me and pushed 
me into my closet. I couldn't see a thing, and then I 
felt his cock enter my anus. He was rough, pushing in 
and pulling out. I yelped a little bit, and then I 
heard him sigh and I felt a warm stream enter my ass.

He pulled out of me, and then I turned around and 
pushed him into the bathroom. I turned on the shower, 
and we grabbed the soap and lubed each other up. We ran 
our hands over each others penises, masturbating each 
other until we shot off in the shower. We washed off, 
and then we got dressed for bed. I lay in my bed, and 
he offered to sleep on the floor.

We went to bed for the night. We woke up the next 
morning, and we sixty-nined each other. I kept rolling 
my tongue over his cockhead, and he kept groaning as I 
did. Finally, we got dressed, and he went home.

V: "...and you did all of this behind my back?"

G: "You wouldn't have let us do it if we told you."

V: "Good...freakin... point!"

G: "What's done is done, right?"

V: "I suppose its ok. I was banging Billy that day =D."

G: "Billy...oh god! That Billy?"

V: "Yep."

G: "I honestly didn't think he was... I could've sworn 
he was straight."

V: "In that case, your gaydar isn't as good as mine. 
That boy was freakin hot..."

G: "So, you gonna tell me how all this went down?"

V: "If I must..."

Back in the spring, before the fourth marking period 
had started, my parents had begun to plan our yearly 
trip to Florida for vacation. They asked me if I wanted 
to take a friend. I gave my friend from high school, 
Billy, a call. I asked if he wanted to go, and he said 
of course!

So, about three weeks after finals were over (about two 
weeks after going over Jeff's house), Billy, my parents 
and I all flew to Florida. We have a timeshare down 
there at Sheraton Vistana resorts. My parents obviously 
took the master bedroom, leaving Billy and I to share 
the other bedroom. 

Billy and I walked into the room, and we each took a 
bed. He took the one closer to the door, and I took the 
bed in the opposite corner of the room. We threw our 
suitcases down, unpacked, putting our clothes in 
drawers, etc. It was early, so he and I threw on some 
swimsuits and went down to the pool. We swam around in 
the pool, under the waterfall for a while. Well...he 
swam. I mostly admired his body, trying to keep up with 
him.

We went back to the room, ordered dinner from Pizza 
Hut, and then called it a night. We hopped into our 
respective beds and watched TV for a little while. We 
covered up, shut the TV and the lights, and we planned 
to go to bed. I should say, he planned to go to bed. I 
wasn't done that easily.

"Hey, Billy?" I asked.

"Yeah?" he replied.

"I just have to asked to satisfy my sick and twisted 
mind. Are you straight?"

He sighed, and drew a deep breath. "How obvious is it?" 
he asked.

"Not very," I said. "I'm bi, so I have great gaydar."

"Are you really?!" he asked me, almost shouting.

"Calm down! Yes, I am! I have been for a couple years."

"Oh my Go... I thought I was all alone!"

"Billy, why the hell do you think I invited you to come 
sleep with me in Florida?"

There was a pause. "You have a point," he said after a 
minute. "Why, do you have something for me?"

I blushed in the darkness. "Well..." I said quietly. "I 
don't know if it's a thing for you or not, but I 
definitely think you're hot."

Now it was his turn to blush. "Y-you do?" he said 
hesitantly. "T-thanks!"

He was a pretty shy boy. I think that may be what 
attracted me to him. He continued, "You... you wanna... 
you know, do something?"

"When? Now? In the morning?"

"Whenever," he said.

I thought for a few minutes. I had actually been 
fantasizing about doing something to someone in one of 
Vistana's room for a good long while now. Then it hit 
me: there was a private beach within walking distance 
of Vistana. Allow me to correct myself: a private 
nudist beach.

I told him my idea, and he said yes. And so, a new saga 
began to unfold...

We went to bed, for the time being. Allow me explain a 
part of the layout of a typical Vistana room. You open 
the door, and you are in a transitory space between a 
living room and a kitchen (technically, you are right 
on the tiling of the kitchen). From there, the kitchen 
is two your right, and the living room and patio to the 
left. If you head straight, you reach a hallway.

At the hallway, there is a door in front of you that 
leads into a generic bathroom (sink, commode, shower). 
To your right was the door that led into the smaller 
bedroom. To the left was the master bedroom, with a 
door that led to the patio, and a door to the master 
bath. In the smaller bedroom, there was also a door to 
the generic bathroom.

When we woke up in the morning, we locked the door to 
the bedroom and the door that led from the bathroom to 
the hallway. We left the door from the bedroom to the 
bathroom open, and I started to run the shower. Billy 
and I both stripped, and got into the shower. He was 
new to actually doing something with another boy. 
Fortunately for him, I had been around a couple blocks 
with George and Jeff.

I grabbed the bar of soap and lathered up my hands. I 
stood behind Billy and reached my arms around his body, 
cuddling him to me. I slowly reached down, and finally, 
I found the shaft of his cock. At that point, he was 
still flaccid and only about 2 inches, but it didn't 
take much to change that. I slowly stroked him and 
watched as his erection grew to four and a half inches. 
I saw his eyes widen, and then he closed them as he 
stood there in bliss. I heard him start to pant, I felt 
him moving in rhythm with my hand, and I saw the smile 
spread across his face.

Within another minute, he moaned, "Ooooooh... Vinny... 
don't stop... it's coming right now!" Right as he said 
that, I felt his body tense, and his penis spasmed as 
he shot four globs of semen all over the shower wall. 
He took a second to rest while I made sure the wall was 
cleaned up very well.

Now it was his turn to try something with me. Billy 
wasn't exactly among the tallest of boys. I think that 
this also contributed to my attraction to him. He told 
me to close my eyes and that he was going to try 
something new (new for him, anyhow, I didn't know 
whether or not it would be new for me).

I did as he asked and I shut my eyes. I heard something 
hit the floor of the shower, and then I gasped as I 
felt him take my penis into his mouth. I asked if I 
could open my eyes, and I felt his head bob up and down 
on my cock, which I took as a nod.

I opened my eyes, and saw that he was kneeling on the 
shower floor with my erection ramming against the back 
of his throat. I knew he was small, but...what a 
perfect height! Not to mention the fact that he was 
extremely good for his first time.

I felt the pressure begin to build up in my balls and 
at the base of my cock. "Billy," I breathed, "if you 
want a mouthful of sperm, keep going. If not, s-stop 
now." I felt him sucking harder, so I guessed that I 
knew what he wanted. I groaned as I felt the sperm 
making its way towards the opening of my penis, but I 
felt Billy pull off of my cock at the last second, 
leaving his face right in the way of the exploding 
volcano of semen.

I looked at him, five seconds after I had finished 
orgasming. His entire face was covered with cum. And he 
was positively glowing. I grabbed him by his ass with 
both hands, pulled him towards me, kissed him, and then 
I licked my sperm off of his face.

We got out of the shower, and we dried each other off 
with the towels Vistana so graciously provided. We 
walked back into the bedroom, shared in one final kiss, 
and then we got dressed. We unlocked the doors, and 
went out to the kitchen to eat breakfast.

After we finished eating, I told my parents that we 
were going to the pools. In my head, I was thinking, 
"Pools, beach...close enough!" I walked out with Billy 
close behind, and we made our way to the private beach 
three blocks away.

On the edge of the beach were small cottages that were 
used as changing houses. There were markers on the 
doors that indicated whether or not a cottage was being 
used, and Billy found one right away. We went into the 
house, disrobed, and went back out. I took a quick look 
up and down the beach. There was no one there. Thank 
God for Walt Disney World!

He grabbed two towels from his bag and spread them on 
the sand. He knelt down, and laid down face up on one. 
I reached into my bag and grabbed some sunscreen, and I 
knelt down next to him. He had his sunglasses on and 
his eyes closed, so he jumped when I grabbed his penis 
and started lathering him with sunscreen. My hands 
began to roam his body, ensuring that none of him would 
get burned: his chest, his stomach, his hairless legs, 
his baby-smooth ass...

I allowed myself to fall to the ground next to him, 
collapsing and reveling in the moment. I heard Billy 
shift a little bit, and I felt his tiny hands lathering 
up my body just as I had done to him. He finished up, 
got back down on his towel, and we lay there, soaking 
up the rays for a while.

Finally, when my erection began to hurt, I knew I had 
to do something to that boy before it killed me. I said 
to him, "Hey Billy. Horny yet?" I glanced down at his 
lap and saw his circumcised penis start to grow.

"Mhm," he replied.

"Good! Wanna do me a favor? Get on all fours." He did 
as I asked, kneeling on the ground with his hands 
stretched out in the sand in front of him. I stood up, 
got behind him, and said, "You ready?"

He took a breath, gulped, and said, "As ready as I'll 
ever be."

I smiled at his hesitance. He really was a small boy. I 
wondered if it would hurt too much, considering he was 
still an anal virgin. Ah, well. Too late for second 
thoughts now. I grabbed his sides and pulled him back 
towards me, slowly letting my cock sink, inch by inch, 
into his tiny ass.

I heard him gasp in pain, and I felt his anus squeezing 
against my cock. I pulled out for a second, grabbed the 
sunscreen, and re-lubed. I pushed back in, this time 
quickly, and I kept thrusting as rapidly as I could. I 
felt his hips start to sway and I saw his cock sticking 
out farther underneath. I lubed my hand and reached 
down, trying as best I could to jerk him off in rhythm 
with my thrusts.

After another twenty seconds, I felt the familiar 
tingling feeling. I whispered to him, "Get ready..." as 
I blew my load into his ass. I shuddered as the 
sensation that was so familiar, yet so new with each 
new boy, took over my body. Below me, I felt Billy's 
body tighten up, knowing that my orgasm had driven him 
into his own. I saw him shoot his load on the towel 
below him, and he collapsed right into it.

After we rested for a minute, we ran into the water, 
washing each other off and splashing each other with 
the warm ocean sea. We went back into our cottage, 
shared an embrace, and got dressed. We walked back to 
Vistana, and had lunch, with tall glasses of milk. I 
poured my glass, looked at him, and chuckled a little 
bit as I imagined him drinking even more white fluid.

We spent the rest of the day walking around the resort, 
enjoying our vacation. I vaguely recall holding hands 
with him a couple of times as we journeyed through the 
vast acreage of land that Vistana had. We stopped by 
Pizza Hut for dinner again, and we went back home. We 
sat in our room for the night again, and we played 
cards for a little while (no strip poker this time, 
just straight up Spades). Bed time rolled around, and 
after all that had happened that day, I was pretty 
wiped...I was ready to go to bed myself, but...I 
figured I would be abandoning him if I didn't at least 
offer to do something else.

"Billy?" I asked.

"Yeah?" he said back.

"Wanna sleep with me tonight?"

"Sure!"

We got changed into our pajamas for the night, and I 
threw back the comforter. I hopped in, and he hopped in 
and rolled the comforter back. I said my nightly 
prayers, and I felt him wrap his arms around me. I 
hugged him back, reaching down and squeezing his 
flaccid cock. "Night, Billy," I whispered.

"Night, Vinny," he whispered back. "I love you!"

"I love you too, Billy," I whispered back, and I fell 
asleep with those words echoing through my ears;

G: "Wow..."

V: "Yup. Hes a sweetheart."

G: "I guess so."

V: "Aight. I gotta take off. Time to write the next 
part of the story!"

G: Haha...see ya, man. Best wishes."

V: "You too, George."


~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life.

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Kristen's collection - Directory 57