Date: Sun, 6 Apr 2014 09:32:32 -0400
From: Daniel1989a . <danielmatthews1989a@gmail.com>
Subject: Poker Boy-Part 5

Poker Boy-Part 5


This story, like all my other stories is FANTASY. I do not suggest or
condone sex with minors for any reason. Keep fantasy away from
reality. Please think about contributing to Nifty and help keep this
amazing site going.


     I stood watching the boys walk away, naked, my hands in cuffs behind
me and attached to the collar around my neck, making it impossible for me
to move my hands without causing the collar to tighten around my neck.  I
had lost everything it had taken me so long to win to Harry and since then
the women had removed all my body hair, I had just given a blow job and
been jerked off on by other boys I had just met, their cum still damp on my
body. And to top it off I had bet and lost, meaning that all five of them
were going to fuck my virgin hole tomorrow, unless I got lucky and came up
with a way of getting myself untied. I started walking slowly, the cock
ring keeping my erection painfully hard, towards where they said Harry
lived.

     As I neared the road I had to slow my walking as twigs and other
things were poking my naked feet, then as I got to the road I had to slow
even more as the pavement was now very hot. My feet could not take the heat
long so I I had no choice but to walk along the side of the pavement even
though it was covered with gravel and stones. My walking slowed even more
as the sensitive bottoms of my feet seemed to step on every pointed or
jagged stone. I was lucky at least that no cars were around and a few
minutes later I saw a few houses in front of me and realized I did not now
which one was Harry's. The boys had told me that his house was the only one
and now I had no idea what to do. It's not like I could go and start
knocking on doors, first I was naked and hard and second, my hands were
bound behind me. The cock ring they attached was doing a very good job of
keeping me almost painfully hard and every time I tried to struggle out of
my wrist binds the strap attached to my neck tightened and started to cut
off my air.

     On top of all that the wind was gently blowing over my now totally
hair free body, thanks to the women and I had the word slave written across
my front and back. I tried not to think about any of this and kept walking
forward. As I passed the first house I was happy it looked empty but as I
approached the second house I heard what sounded like a lawn mower. As I
got closer I heard that the sound was coming from behind the house, so I
took a deep breath and started walking faster to get past. I was almost
half way past the house when I heard the lawn mower shut off and when I
turned my head to look I gulped hard as I saw the gate to the back yard
opening. I looked around fast but there was no where for me to go, bound
the way I was I could not run and even if I did there was no where to hide
so instead I stopped walking and stood as still as I could hoping whoever
it was would not see me. I watched as a large man with no shirt on walked
through the gate and was turning to go into his garage and I figured my
plan had worked. When he entered his garage I would walk fast and be past
before he knew, but then his head turned towards me, then quickly back
towards his garage. I stood still, but then his head snapped back towards
me so fast that in any other situation I would have laughed.

     The man stared at me, then actually rubbed his eyes as he tried to
figure if he was seeing things. Then to my horror he started walking
towards me, a large smile spreading across his face as he got closer. As he
got even closer I saw he was larger than I had thought, tall and heavy, not
overly fat, but very stocky. His head was almost bald except for a very
little hair, he was clean shaven and wearing sandals and baggy shorts. His
body had a thin sheen of sweat as well as his head and his feet and the
lower parts of his legs had grass clippings on them. His smile widened even
more and my instinct was to run, but he was too close and there was nowhere
for me to run to anyways. Now only a few feet away I watched his eyes
slowly take in every part of my body, then they lingered on my very hard
cock. He looked like he was trying to think of something to say and his
mouth opened a few times, then closed again, then finally he smiled even
wider and stuck out his hand and said,

     "I'm Jason, nice to meet you."

     He then started laughing loudly, obviously finding my hands bound
behind my back very funny.

     "I guess shaking hands is out of the question. So kid, how did you get
yourself in this predicament?"

     I thought about lying, but then told him the whole story, starting
with Harry on the bus and ending with the neighborhood boys who had left me
like this. Jason's eyes widened with surprise as I told him everything, but
the smile never left his face as his eyes kept going from my head, down to
my feet, then back up again, soaking in my naked body. When I finished
talking his eyes met mine and he said,

     "Well boy, those ladies did a very good job of removing your body
hair, you look as smooth as any boy or girl I've ever seen, and I do love a
smooth body."

     My mind raced, trying to figure out a way of getting away from here,
but the more he stared at me the hornier I got, his eyes were not just
looking at me, it was like they were adoring me. I saw his face start to
redden slightly and when I looked down I saw that there was now a bulge in
the front of his shorts. I saw his mouth open as he said,

     "Yes, a very nice smooth body, why don't you just turn around and let
me get a look at the backside boy?"

     I had no choice so I slowly turned until my back was facing him and
heard him let out a low gasp of pleasure, then heard him say,

     "Damn boy, that is one tight smooth butt you got, almost as pretty as
a girls."

     Hearing him compare me to a girl made me speak before thinking as I
said loudly,

     "I'm not a fucking girl."

     Before I knew what was happening I felt his hand grasp my shoulder,
then he spun me around until I was facing him, his face now red with anger
as he said,

     "That was very rude boy, I didn't say you were a girl. I was just
about to undo your hands and let you go, but now you are going to have to
earn it."

     His hand lingered on my shoulder and as he pulled it away he let it
drop a bit and ran the back of it across my right nipple, which caused me
to moan lowly. His smile returned as he said,

     "You may not be a girl, but your nipple sure is sensitive like a
girls."

     I did not like where this talk was going so I asked,

     "I'm sorry I swore Sir, could you please just let me go?"

     He looked me up and down, then smiled and said,

     "No boy I won't. But, since you like gambling so much, I will give you
a chance to win your way out of your binds."

     Hearing that my mood cheered, but then remembering the losing streak I
had been on I cautiuously asked,

     "What's the bet Sir?"

     "Well boy, first lets get inside out of the sun, ok?"

     I hesitated, but then agreed and followed him across his front lawn
and inside his air conditioned house. He led me into the living room and I
was happy to see that although there were a few pictures of two girls who
looked to be around my age, it seemed like no one else was at home. He saw
me looking at the pictures and said,

     "Those are my daughters, don't worry, they won't be home for hours,
take a seat on the sofa."

     I awkwardly sat down, then listened as he said,

     "I'll give you a fair chance boy, one hand of poker. If you win I'll
untie you and give you a pair of shorts, a t-shirt and some sandals and you
can get on your way."

     The thought of finally having some clothes again was uplifting, but
then remembering my losing streak I asked,

     "And if I lose Sir?"

     "If you lose, you cut the rest of the grass in my backyard, and you do
a very good job, then I'll take you as you are now and drop you at Harry's
place, is it a deal?"

     My eyes lit up, I was going to Harry's anyways, the bet was almost too
good to be true so I agreed right away and watched as he got up and
returned with a new deck of cards. He opened the pack and took a few
minutes shuffling then said,

     "To speed things up we'll just play five card draw, one draw, no wild
cards."

     I agreed and dealt out five cards to each of us. After looking at his
cards he picked up mine and showed them to me, while looking away so he
could not see them. I had two tens, a king, a seven and a three, so when he
put my cards back on the table I told him which ones I wanted to throw
away, then watched as he dealt me three new cards. He looked at his cards
first again, then showed me mine, my hand had not improved, but I didn't
really care, all I would have to do is cut the lawn if I lost. He turned
his cards over and had two pair, which easily beat my one pair, so he
smiled at me and said,

     "Okay boy, let's go."

     I stood and walked behind him towards the back door of the house, then
as we entered the kitchen I stopped in my tracks, my eyes widening in
shock. Through the sliding glass door I could see that there were several
houses behind Jason's and to my horror, there were no fences and the house
right behind his had what looked like a bout 20 girls my age having a pool
party. The lawn between Jason's place and the house behind was big, but if
I walked out there, all those girls would see me. Jason turned his head and
smiled wide as he said,

     "Did I forget to mention there were no fences and a party going on?"

     He then grabbed my shoulder and started pulling me towards the glass
doors. I struggled as hard as i could then pleaded,

     "Please Sir, no, please, don't make me, please."

     His hand started to pull even harder, but then he let up a bit, smiled
even wider and said,

     "No, I think it will be good for you to be seen like this, I'm sure
the girls will love it, let's go boy."

     He then pulled harder and we were just about to go out the door when I
pleaded again,

     "Please Sir, please, give me a chance please, one more hand please
Sir."

     He was now outside the sliding door and was about to pull me out too,
but then he paused and said,

     "You don't have anything to bet boy, what could you possibly put up?"

     His hand tugged harder on my shoulder as my feet started to pass the
door I said,

     "Anything Sir, anything you want, please Sir."

     His hand slowed then stopped pulling me as he said,

     "Anything boy? You Sure?"

     I told him I was and a minute later we ere back in his living room,
this time he was sitting with me standing.

     "Okay boy, here's the bet. One hand again, but two draws this time and
you can raise on each draw. Since all you have to bet is your body, if you
lose, you're mine, if you win, I untie you and let you go, agreed boy?"

     I paused, thinking then said,

     "That seems unfair to me Sir. If I win I just leave, how about you put
up some cash too."

     "I don't have much cash on me boy, don't get greedy, I'll take you out
back right now."

     My eyes spotted his watch on a table and I could see it was very
expensive so I said,

     "Okay, how about you put up that watch too Sir?"

     He thought for a moment, then said,

     "That's a very expensive watch boy, you better be worth it, but, it's
a deal boy."

     He dealt out the cards, five to each of us, then looked at his, put
them back down and showed me mine. I watched carefully to make sure he
wasn't looking, and satisfied that he was being honest saw I had two kings,
an ace, a ten and a four. I watched as he took three of his cards and put
them on the table, then I told him the two cards I wanted to throw away,
keeping the kings and the ace. Before he dealt, he asked,

     "Any raises boy?"

     I thought about it, I had a strong hand but I shook my head wand
watched as he dealt the first draw cards. He looked at his and then showed
me mine and I had to control my expression when I saw that i now had three
kings, an ace and a ten. This time when he asked if I wanted to raise, I
could not hold back and said,

     "Yes Sir."

     He looked at me, smiled and said,

     This gold chain I am wearing is very expensive, I'll add it to the
pot, but, if you lose, you will do whatever I say, no exceptions for the
next two hours, agreed?"

     I knew this was a big bet, but his face was showing he did not have a
strong hand so I said,

     "Agreed."

     He looked at me and said,

     "I want to hear you say it boy,what you'll do if you lose?"

     "Anything you want for the next two hours Sir."

     He dealt the cards and looked at his, his expression changed, it was
hard to read but I was pretty sure he had not got the cards he had been
hoping for. he then showed me mine, my hand had not improved, but three
kings was a strong hand. He looked at me and said,

     "Well, time to show boy."

     He flipped his card over and my heart sank as i saw he had a flush,,
which easily beat me three of a kind. He smiled wide and said,

     "Looks like you are mine for two full hours boy, but, since I like
girls, I think we'll start by making you look prettier."

     He stood quickly and ran upstairs,leaving me alone, my heart pounding
wondering what he was doing. A few minutes later I heard him coming back
down the stairs and seconds later he walked into the room carrying what
looked like some clothes and what looked like a round suitcase. He sat on
the sofa beside me and his hand went right to the top of my thigh, then he
ran it around and down my leg then back up and said,

     "Damn boy, you're smoother than my wife, not even any stubble, this is
going to be fun, but you look too boyish so let's work on that. But we have
to be fair, don't we?"

     He pulled out an alarm clock and set it for two hours, then he opened
the round suitcase and pulled out a long blond wig, then as he started to
put it on my head I pulled back, but he grabbed my shoulder and said
loudly,

     "Boy, you lost and agreed to this, you pull away or disobey me again
and I will spank you raw and then chain you outside as close to the
neighbors as possible and let all those girls do whatever they want to
you."

     I knew he was serious so I relaxed and a few minutes later he had
applied the wig to my head, covering all my own hair, then adjusted and
brushed the long blond hair. He looked at it and satisfied said,

     "Stand up boy."

     I awkwardly stood in front of him, my erection throbbing and bouncing
up and down, then watched as he pulled a pair of nylons out of the pile of
clothes. It hit me then that he was going to dress me as a girl. My heart
started pounding and my face reddened more than ever before in my ,life. I
wanted to plead with him, but knew it would make things worse so I just
stood there. He told me to raise my right foot and when i did, he slipped
the nylon stocking on, then eased it up my leg to the middle of my thigh,
he then did the same to my left leg. I watched as he pulled a pair of small
panties from the pile and after making me raise my feet, he pulled them up
my legs to just below my cock and balls. He then looked at me and said very
firmly,

     "Boy, I'm going to push your cock back and underneath between your
legs, then pull these panties up. You will keep your legs tight together so
your cock does not bounce out at all, understand?"

     It took me a moment, but then I knew what he meant and that in that
position it would look like I did have a cock at all. It was a bit awkward
because I was so hard, but he got it out of the way and pulled the black
silk panties up. They were very tight and sheer, pretty much see
through. He then grabbed something I did not recognize, but then he
attached it around my waist like a belt, and as he attached the clips
hanging down to the top of the stocking I knew it was a garter
belt. Finished with that he sat back and looked me up and down, and seemed
pleased with what he saw. My humiliation was deeper than ever before, but
at the same time my nipples were erect and my cock throbbed between my
legs. He then looked at me and said,

     "Okay boy, I'm going to undo your cuffs, but don't even think about
moving, got it?"

     For a moment I thought I would run as soon as my hands were free, but
before he took the cuffs off, he attached a pair of cuffs to my ankles, so
there was no way I could run. He undid my hands and removed the collar from
around my neck, then took out a rag and some cream and rubbed off the word
slave that the boys had put on my chest and back. He told me to put my hand
son my head and when i did he gently ran his fingers up and under my arms,
then said,

     "Damn, totally smooth here too, you are starting to look like one cute
slutty girl."

     My face reddened even more as he tot my utter humiliation started
applying make up to my face. He started with lipstick, then eye shadow and
blush, mascara and other make up I had no idea what to call. He sat back
and said,

     "Long blond hair, bright red lips, stockings and a garter belt, now
you are looking very slutty girl, but something is still missing."

     He pulled something from the pile and then reached around my torso and
attached it at the back and when I looked down my humiliation was complete,
it was a very natural looking set of fake breasts. They were quite large
and looked very life like, smooth with very large erect nipples at the
end. They were attached tight enough that when I moved the breasts jiggled,
but the strap holding them did not move. He had me stand up, then looked me
up and down and said,

     "Now that is perfect, you look just like a slutty little whore."

     I caught a glimpse of myself in a mirror on the wall and was shocked
to see how much like a girl I really did look. I figured a lot of people
would not recognize me, even people who knew me. He pulled me from my
thoughts saying,

     "Get on your knees in front of me slut."

     Once I was on my knees he said,

     "Now use those sweet slut lips of yours and start sucking my cock."

     I reached out and pulled his shorts down, seeing his cock pop out I
was pleased it was not too large. I opened my mouth and took part of it
into me, running my tongue around the head and hearing him start to
moan. His cock was small enough that I could get it all into me with ease
and from the sound of his moans, I figured he would not last long. Almost
twenty minutes later my mouth was still working his cock and a minute later
he laughed and said,

     "I can last a long time slut, going to give you a real workout."

     Ten minutes later my jaw was getting sore from the effort and luckily
he told me to stop. He told me lay down on my back, which I did and watched
as he stood, then knelt down, straddling my chest. He ran his hair through
the long blond wig hair, then leaned down and kissed me on the lips, then
pushed his tongue through and into my mouth. He lowered himself more until
he was almost laying on top of me, his very hard cock rubbing up and down
between the tops of my thighs, his tongue exploring my mouth as his hands
ran over the breasts and down my sides. He started thrusting his hips up
and down, driving his cock up and down between my thighs as he started
moaning louder and louder.

     He pulled his mouth from mine, then said,

     "You love this slut, don't you?"

     I nodded my head but he yelled,

     "Say it whore, tell me how much you love it, beg me to fuck you."

     I took a deep breath and said,

     "Oh God, I need you so bad, please fuck me."

     He started kissing my lips again and knowing what he wanted I started
moaning loudly as his hips thrust up and down my thighs, begging him to
fuck me. I thought he had cum when he stopped thrusting, but instead he
said,

     "Okay slut, now it's time to really fuck you, gonna give your pussy a
real workout."

     He must have seen the fear and anxiety in y eyes, because he said,

     "Don't worry kid, not gonna use my cock."

     He reached up and put a medium sized dildo in front of my eyes, then
said,

     "Now, beg me to fuck you slut."

     I was still nervous, but more excited as I opened my mouth and said,

     "Please fuck me, I need you so bad."

     He raised himself up, then sat on the sofa and told me to stand up in
front of him. When I did he turned so my back was facing him and when he
told me to bend over I did, now every exposed and anxious. I felt slippery
cream on my hole and tightened out of instinct. I felt more being applied,
then clamped down even harder as I felt his finger pushing into
me. Suddenly his other hand landed hard with a loud smacking noise on my
right butt cheek as he said,

     "Relax slut, or I'll spank you so hard you won't sit for a week."

     I believed him and with pure will managed to relax my hole enough that
his finger slipped inside. It felt odd at first but as he started to move
it around the feeling changed to a very enjoyable, sexy feeling. His one
finger was soon replaced with two, which took a bit for me to get used to
but the two felt much better than just the one and soon i was moaning for
real as his fingers moved around inside of me. I heard him say,

     "That's it you slutty whore, moan as I play with your pussy."

     He did not have to encourage me, the sensation of his fingers in my
hole was driving me wild with passion as I moaned even louder. Suddenly his
fingers pulled out of me and a minute later I felt what had to be the dildo
pushing against my hole. I had seen it and knew it was smaller than my own
cock, but it felt huge and my hole muscles clamped down tight. I knew this
was going to make him mad so I concentrated as hard as i could and a few
minutes later felt the head of the dildo push inside me. My muscles clamped
down on it and I felt my cock start to throb harder than ever before in my
life as I heard myself moaning loudly. He slowly pushed more and more until
the dildo was all the way inside me, then he started slowly pulling it out
and then pushing it back in again. I knew what he wanted and I actually
wanted it too as I called out,

     "Oh yes, please fuck me, please fuck me, I need it so bad."

     I felt myself right on the edge of cumming, it was building up to be
one of the most intense orgasms of my life, but he must have sensed it and
quickly pulled the dildo out of me. He turned me around and showed me a
bigger dildo, this one was easily as large as my own cock, probably a bit
bigger, then he said,

     "Okay slut, I'm gonna lube this up and put it between my legs,you are
gonna turn around and slowly sit down on it, got it you whore? Then when
you get it all the way in, you're going to raise yourself up and down on
it, starting slow and then going faster and faster, until you are ramming
it in and out off that pussy of yours, while you moan like the whore you
are, got it?"

     I told him i did, but I was nervous the smaller dildo had felt huge,
but with no real way of getting away, and deep down, not wanting to, I
watched him lube the dildo and put it between his legs. I turned and slowly
backed up, then put my hands behind me on each side of his lap then lowered
myself until i felt the head at my hole. It felt absolutely massive as i
slowly started lowering myself onto it as I felt Jason's one of Jason's
hands reach around to play with the breasts. The head was big and I was
starting to think it would never fit, but then my left hand slipped and
instead of slowly, I fell down and the dildo rammed all the way inside of
me at once. There was a flash of pain, but it left and was replaced by
extreme pleasure. I felt so full as Jason continued running his hands over
the breasts and up and down my sides as he said,

     "I knew you would take it well, that pussy of yours was made to be
fucked."

     I left it all the way inside of me, getting used to ti then slowly
pushed myself up until it was almost all the way out, then slowly sat down,
pushing it back in. It felt so good I did not have to be coaxed to moan, I
moaned louder than ever before in my life and then started saying,

     "Oh God, fuck me with your huge cock, please fuck me."

     His hands played with the breasts, then he said,

     "Damn slut, if you think that's big, just wait till Harry gets you."

     I briefly wondered about harry, but those thoughts left as I started
raising and lowering myself faster and faster, driving the dildo in and out
of me as my moans increased in length and volume. I felt myself very close
to cumming and thought I would finally be allowed to shoot, but seconds
later the alarm clock rang and Jason grabbed me around the waist and held
me so I could not move. He whispered in my ear,

     "Well slut, looks like my time is up, you are one hot sexy whore."

     I said,

     "Please just a few more minutes, please!!!!!!!"

     He again whispeerd in my ear and said,

     "Awww, does the slut want to cum, forget it whore, I don't care about
your pleasure, now stand up."

     I slowly stood, the dildo making a low popping noise as it pulled out,
my legs a bit shaky and watched as he removed my ankle cuffs. Then before I
could react he cuffed my hands behind me again and replaced the collar and
atttcahed the cuffs with the strap to the collar. He then pulled off the
wig and other clothing, then wiped my face clean of make up, saying,

     "I'd like to leave you looking like a girl, but old Harry is only into
boys, and boy are you ever his taste. But, I do want to leave you with
something, bend over."

     I did what he said and felt what I thought was another dildo being
pushed into me, but when I stood back up it didn't push out at all."

     "That's a butt plug boy, it will stay in place and get you a bit more
open for Harry."

     The butt plug was driving me wild, my hole muscles clamped then
relaxed, then clamped as it forced my cock to stand almost straight up. He
led me to the door, then ran his hands up and down my back, then up and
down my chest, sighed loudly and said,

     "I would love to have you for a couple more hours, but, Harry's place
is two houses down the street, have fun."

     He pushed me outside and I heard the door slam and I was again bound,
naked, hard and alone, now on my way to Harry's place.


Authors note: I hope you enjoyed this chapter. Comments and suggestions are
always welcome. Right now I am thinking of one maybe two more chapters.