Date: Sun, 24 Jul 2005 04:11:30 -0500
From: None Given <nwmnboy@gmail.com>
Subject: On a Bet

Warning

The following story is true. This story contains graphic descriptions
of sexual acts between 2 teen boys. If such material offends you or is
illegal in the location from which you are reading it, please seek your
reading enjoyment elsewhere.

This story is copyright protected under the name "nwmnboy". This story
may not be redistributed in whole, or in part, without the expressed written
consent of the author. This story may not be used by anyone in the pursuit
of monetary gain. If you want to post it on your website, please email me
first and ask. You must give me full credit for the story if I decided to
let you use it. Thanks for co-operating; I hope to release more stories if
this one is well received :)

Authors Notes

Your comments are eagerly appreciated at nwmnboy@gmail.com. All emails
will be answered except flames - they are deleted when received.

This is my first publicly released story.



I'm not sure what anyone else's real first time was like, but I'll share
mine.  I had recently moved from a rural area to one of the northern
suburbs of Minneapolis.  It was the summer of 1977 and Star Wars was the
big thing that year.  We moved as soon as school ended in the spring, so I
couldn't even meet anyone new at school before it ended.  I had left all of
my old friends that I had known all of my life and moved the 50 miles into
town because my mother and step father needed to find a cheaper place for
my sister and I. I was faced with changing schools, moving into a new
neighborhood where I didn't know a soul, three long months until school
started, turning 14 soon, and the onset of puberty.  As it turns out, this
was one of the best times of my life and I'll always remember that summer.

 I stayed in the house for the most part, aside from going outside to do
yard work and the occasional run down the street to the convenience store
for my mother or step father.  I would sometimes see some of the local boys
playing across the street in a big field, or riding their bikes down the
street, but I never approached them.  Part of it was my insecurity, part of
it was that I didn't know how to start.... I'd lived in the same place all
of my life and didn't have any idea how to be the "new kid".  One day I was
out mowing the lawn and one of them rode up to me on his bike and
introduced himself.  His name was Jerry and he was my age and would be
going to the same school as I would in the fall.  Jerry was about 5'4,
black hair, brown eyes, and thin at about 100 pounds. We talked for a while
as I finished mowing the lawn and he helped me rake up the grass.  My step
father was a real hard ass and I was guaranteed an ass whipping if I didn't
get the yard to look immaculate.  Anyway, I got the yard finished and Jerry
asked if I wanted to play baseball with the other guys across the street.
I asked my mother and she approved wholeheartedly.  She knew how difficult
the move had been for me and almost seemed relieved that I was meeting
people finally. I went across the street and Jerry introduced me to the
others.  There was Paul (5' 7", blond, blue eyes,huskier than Jerry or I at
about 140 pounds), Todd (5'4, Brown hair, green eyes, and about 110
pounds), Jimmy (4'10, brown hair, brown eyes, and 85 pounds), Greg (5'4,
brown hair, green eyes,100 pounds), Jeff (5'11, brown hair, green eyes, 150
pounds), and Derek (4'8, blond hair, green eyes, 75 pounds).  They were all
my age except Jeff who was a year older and Derek who was a year younger
and all lived on the same street as I did.  We played 500, where one guy
hits the ball and you catch it for points (fly balls are 100, one bounce
75, grounders 50) and the first person to 500 gets to bat.  I was always
very poor at sports, being 5'2 and weighing in at 95 pounds.  We played for
a couple of hours and I never once got to bat.  I was certain that the
others were thinking that I was a complete moron, but I kept at it and got
to 425 once.  As we played, Greg and Jeff kept picking on each other a lot,
and I thought that they were going to start fighting a couple of times.  It
turned out that they were brothers and did that all the time.  Throughout
the game, the guys kept asking me questions, getting to know me, and just
basically accepting me.  As 5:00PM rolled around, the game broke up as
everyone had to get home for dinner and their chores.  They told me that we
would play again the next day and to be there at 10:00.

 I went home and ate dinner for the first time in weeks with a smile on my
face, much to my mother's relief.  Of course, being a mother, she wanted to
meet my new friends.  I got up the next morning, did all of my chores, and
left the house at 9:55 to go across the street. Jerry and Paul were there,
so we warmed up a little and they gave me some pointers, and by the time
the others showed up I felt a little more confident in my skills (for want
of a better term..lol).  We played until about lunch time and I actually
got to bat once.  We decided to break for lunch and be back in an hour.  We
were all starting to leave and I noticed that Jerry was just standing
there.  I asked him why and he said that he didn't feel like going home
since his older brother and his girl friend were there and the last time he
walked in on them he got his ass kicked.  I invited him for lunch at my
place... A coup for me, my mother gets to meet one of my friends, and it
shouldn't be too embarrassing.  We had sandwiches and chips and, to my
relief, my mother was quite well behaved.  We went back out to play ball
again after we were through eating and Jerry thanked my mother for
lunch. As we were leaving my mother told me what a "nice young man" he was
and seemed quite pleased.

 We played for a few more hours and at about 4:00PM we saw Jerry's brother
and girlfriend leave his house before his parents got home.  We were
winding up for the afternoon and Jerry asked me if I wanted to come over
for a coke and to meet his mother and father when they got home.  I went
over, and he confessed that he dreaded me meeting his parents as much as I
did him meeting my mother.  I was amazed at how well we got along.

 We got to his house and hung out for a while.  He showed me his room and
the house and just as the tour ended his parents arrived.  He introduced me
and we made casual conversation for a few minutes.  Then, I noticed that it
was just after 5:00PM and I told them I had to get home.  Of course, I was
late getting home for dinner.  I explained to my mother that I had met
Jerry's parents and that was what delayed me.  She accepted my explanation
and I thought that all was well.  Then my step father announced that one of
the lids was off on the garbage cans and that he had found a spot in the
yard that hadn't been properly raked.  He told me that as soon as dinner
was over I would need to go out and take care of these problems.  I ate
dinner and then rushed outside to take care of the "problems".  I came back
into the house and was told to go downstairs to my room and that he would
be right down.

 Head hung low, I went downstairs wondering what the asshole was going to
do next to torment my life.  I waited for about 15 minutes and heard he and
my mother arguing about me being responsible or careless, the fact that he
was raising her kids and that they would start to behave, etc..... I knew I
was in for it.  When he came downstairs, he told me that just because I was
making friends was no reason to neglect my responsibilities around the
house and that I had a choice to make.... I could either be grounded for
two weeks or he would get the belt and it would be over with tonight.  He
left me alone and told me to come upstairs when I had decided.  I thought
about it for quite a while.  I didn't want to lose my new friends or two
weeks of summer vacation, but getting a bare assed whipping when you're 14
is degrading.  Not to mention the fact that if I took the whipping it would
be because I "asked" for it.  We were supposed to meet again at 10:00 the
next day to play ball and hang out again, and I didn't want my new friends
to think I didn't like them, so I gritted my teeth, went upstairs and told
him that I was going out to play ball tomorrow.  He told me to go
downstairs and get ready and he would be down shortly.

 The last time he had whipped my ass it was sore for a week.  Getting ready
consisted of getting the belt out of the closet and laying it on the bed,
taking my pants and underwear off, and when he arrived I had better be bent
over the bed waiting.  He didn't usually talk much before the beating, just
how many and that I should count them off.  I sat on the bed thinking that
this would be the last time I sat comfortably for a while when I heard him
coming down the stairs.  I quickly stood up, went to the end of the bed,
and bent over waiting for his arrival.  He walked into the room, picked up
the belt, commented that it was a good thing that I hadn't forgotten how
this was done in the past six months.  Using some mathematical formula that
eludes me to this day, he decided that I would get 12 swats.

It seemed that he had no sooner given me the number when the first swat
landed..."One, Sir!", I almost screamed.  A few moments later, the next,
"Two, Sir!", I said through gritted teeth. He always paused a bit between
each swat so the sting would set in, then several seconds later as the pain
of the first two was setting in.. whack!  "Three, Sir!", I blurted, and
then to my suprise.. Smack! "Four, Sir!" and then smack "Five, Sir!" and
whack "Six, Sir!" and then the pause... I used to think that the pause was
the worst thing.. Taking three in a row almost as fast as I could count was
way, way worse.  He had changed his strategy and paused every three swats.
The pain was intense and I had tears in my eyes.  We were only half done
and I was already regretting my decision. Nothing could be worth this
pain.. Whack..."Seven, Sir!", Whack.."Eight, Sir!", I
cried.... Smack... "Nine, Sir!", I said through my tears. Whack.."Ten,
Sir!" Whack.. "Eleven, Sir!", WHAP!... "Twelve, Sir!", I bawled...  As was
the custom, I stood up, thanked him for correcting my behavior, he threw
the belt on the bed, and I started to wipe the tears from my eyes.  He told
me to get dressed and come upstairs.  I dressed pretty slowly, the pain
coming in waves from my knees to my back though every swat had landed right
on my ass.  I put on my underwear and a pair of soft,cotton sweat pants and
went into the bathroom to look at my ass.

 I stood in front of the mirror and looked over my shoulder at the welts on
my ass. The belt was two and a half inches wide and very thick, so it left
wide marks and deep welts. He and I made a special trip to the store to buy
it just after he married my mother, and it had only one purpose. I wiped
the tears from my eyes again, pulled up my pants and headed upstairs for
the humiliation that inevitably followed a spanking.  As I walked into the
living room my sister giggled to herself and my mother looked away.  My
step father sat impassively watching the television.  I started to pull
some pillows over so I could lay on my stomach and watch tv and he just
looked at me and shook his head.  With a grimace, I went to the couch and
gently sat down.  Usually, I had to sit and watch tv for at least an hour
after a spanking so he could see how uncomfortable I was.. I watched for
exactly one hour and excused myself to go to bed.

 I went to my room, laid down on my stomach and fell asleep.  Tomorrow was
Friday, so the weekend was coming.  My last day of rest with my step father
gone to work.  When I woke up, the sting was gone, but the ache had really
set in.  My ass felt raw and lumpy to the touch.  Cold water, warm water,
nothing helped in the shower.  I wondered how I would be able to handle a
day of playing baseball with my friends without them knowing what happened.
I got dressed and put on some loose pants and headed out to play ball.  At
about 2:00PM it started to rain, so since his brother was gone, Jerry
invited us to his house to hang out.  We drank some cokes and watched a
little tv and then he suggested that we go downstairs to the basement where
it was cooler and in case the storm got bad we'd be safe.  Greg and Jeff
decided to go home,and Derek had to go grocery shopping with his mom, and
Todd had gone on vacation for the weekend with his parents.  Paul and I
called our mothers to let them know where we were and that we were safe in
the storm, and downstairs we went.  We watched the tv downstairs for a
while, and then a bright flash, a big boom, and the power went out.  It was
dim, but there was still enough afternoon light to see, punctuated by
occasional flashes of lightning.  We turned on an old battery powered
radio, tuned it to a rock station and discussed what to do.  Jerry finally
broke the ice and grabbed a deck of cards from the table next to him and
suggested that we play cards.  We tried some crazy 8's and then he
suggested that we play poker.  None of us had any money, and just as we
were going to end that idea, he said we could play strip poker.  Knowing
the condition of my ass, I was very reluctant to play.  Paul seemed kind of
hesitant too, but Jerry had the dominant personality and he prevailed.

 We decided to make sure that everything was even.  We each had on a pair
of socks, a shirt, shorts, and underwear.  We decided to play five card
draw, nothing wild.  We got out the Hoyle book to make sure that we had the
order of the hands straight, and we counted the cards to make sure that we
had a whole deck.  All of that being done, we started playing.  Since there
was no money, folding wasn't an option, so whoever won, the other two lost.
Paul was the first winner, so Jerry and I each took off a sock.  I won the
next hand, Paul lost a sock and Jerry was barefoot.  I won the next hand
and Paul was barefoot and Jerry decided to take off his pants instead of
his shirt.  His T-shirt was long and covered almost down to his knees
anyway.  Jerry won the next hand and I lost my other sock, and Paul took
off his shirt.  The storm continued raging outside, but the flashes of
lightning and booms of thunder were almost forgotten for the three of us.
This was getting to be a serious game.  Paul won again, and being the
chicken that I was, and knowing the condition of my ass, I took off my
shirt.  Jerry reached up under his T-shirt and took off his underwear.  I
still don't know what he was thinking, but it sure was a turn-on for
me. Jerry won the next hand, and Paul and I took off our pants.  We were
both a little boned up and that was obvious from the tents in our
underwear.  Here we were... two of us would be naked at the end of the next
hand.  We dealt the next hand and were just about to the draw part when we
heard noise upstairs.  We quickly got dressed and climbed onto the couches
and hid the cards.

 After a few moments Jerry's mom yelled downstairs to see if anyone was
home.  He answered and told her we were in out of the storm.  She told Paul
and I that we should call home and tell our mothers that we were going to
stay for dinner and that we were welcome to stay for the night.  My mother
said it was OK, but Paul's mom told him that he had to go home because his
father had visitation that weekend and would be there any minute.  Jerry's
mom gave Paul a raincoat and he headed home.  She fired up the gas stove
and made cheeseburgers for everyone.  Jerry and I headed back downstairs to
set up a bed for me.  Using flashlights we went into his room and he got an
old camping cot and put it on one side of his room for me.  Once that was
done and he had gotten a pillow and a blanket he closed the door and we
talked a bit more with the flashlight pointed straight up at the ceiling.
We talked about girls and other stuff.  Then after about 15 minutes of
talking he reached into his pocket and pulled out the deck of cards from
earlier.  He asked if I felt like playing again and I said yes.  We agreed
to the same rules as before, and We counted the cards again to make sure
that we didn't lose any of them during the quick cleanup earlier.

 We sat on the floor between the bed and the cot facing each other and cut
for the deal.  He got the high card, so he dealt the first hand.  He won
that hand with a pair of sevens; I had a pair of fours.  Off came my first
sock.  I dealt the second hand and he won again with a pair of Kings to my
ace high.  I was barefoot.  He dealt the next hand and I had an open ended
straight.  I filled it out with the draw and he lost with a pair of nines.
Off came his first sock.  I won the next hand and he lost his second sock.
I won the next hand again, we joked about stacking the deck, and I laughed
because he dealt.  He once again chose to take off his pants under his
shirt.  I lost the next hand and took off my shirt.  I lost again and off
came my pants with the tent in my briefs like the last time.  He lost the
next hand and took his underwear off under his shirt again.  Throughout the
game we had talked about how far we had gotten with girls and what we had
done.  We both lied our way through everything, but it was most likely to
cover the fact that we were getting pretty boned up during the game.

 So, here we were at the last hand.  He shuffled and I cut.  We both knew
someone would be naked this hand.  He dealt the cards and I couldn't
believe it.  I had three sevens before the draw.  I put down two cards for
my draw and he put down three.  I joked to him and told him that I had
him.. he may as well take off the T-shirt now.  He gave me my two cards and
I watched him take three from the top of the deck.  He looked at his cards
and then he asked if I wanted to make it interesting.  I looked at my draw
cards and had a tough time keeping a poker face; I had drawn the fourth
seven.  I confidently said, "Sure, what do you want to bet?"  He said,
"Loser has to do whatever the winner wants."  I thought about it for a
minute, weighing the four sevens in my hand, the boner in my shorts, the
hormones in my bloodstream, and thinking that the highest hand so far had
been a straight.  I knew that I had won, I was sure of it.  The only
question in my mind was what would I make him do when he lost.  I said,
"OK, that's a bet.  Are there any things that are off limits?" And he said,
"No, whatever the winner wants - anything!"  I agreed and we each laid our
five cards face down.  This was big, so we decided to flip them one at a
time taking turns.  I flipped the first card, the queen of spades.  He
flipped the nine of diamonds.  I flipped the seven of hearts.  He flipped
the queen of diamonds.  Seven of clubs.  Ten of diamonds.  Seven of spades.
Jack of diamonds.  I was nervous now... he had 9-10-J-Q of diamonds... and
didn't seem nervous about my three sevens.  I flipped the last seven -
diamonds.  Then he said, "OK, I think I'll take a blow job after you take
off that underwear!", and flipped the King of diamonds up.  My heart and my
boner sank.  I couldn't believe it.  What were the odds?  He just grinned
and waited for me to take off my briefs.  I slowly pulled them down and off
my feet until I was naked.  Then he said, "I think I'll just lean back here
and let you suck my cock.  I'll tell you when to stop.  Now, go to it!" and
he lifted his T-shirt up and spread his legs apart.  His cock was only
about five inches long.  Mine was about five and a half.  We both had a
nice patch of hair above our cocks and some hair on our legs and under our
arms.  He saw the stripes on my ass and asked me about it.  I told him
about it and he felt bad for me.  Then he reminded me that I lost and owed
him a blow job.

 I asked him if he was serious, and he said, "Yes, now go to it!"  So, I
leaned forward on my knees and leaned down and just barely put the head in
my mouth.  My mouth was so dry from nervousness, I almost choked. I kind of
open mouthed it and then sat back up.  I said, "There, I did it." , and
took a drink of coke to wet my mouth a little, and he said, "No, you have
to suck it until I tell you to stop."  Well, I figured that since he didn't
make fun of me for doing it the first time, I'd go ahead and do it the
right way, so I started sucking his cock good.  I did it just like I'd
imagined since the first time I'd ever heard of a blow job.  I sucked him
good.  After about two minutes he told me to stop.  Then he leaned forward,
picked up the cards, and said with a smile on his face, "Want to keep
playing?  If you lose you do what I want you to, and if you win I still
have one piece of clothing to lose. Then we can keep playing doing whatever
the other one wants.".  I said, "OK, I think I've already done the worst
thing, so what the hell."  We played until about 4:00AM, I sucked him when
I lost, he sucked me when he did.  Suddenly, while he was sucking my cock,
boom the lights came on and scared the hell out of us.  We thought we'd
been busted, but then we realized that it was just the power coming back
on.  We relaxed a little and decided we had just had too close a call and
we should get some sleep.  We later discussed it and it was the first blow
job either of us had ever had.  Jerry and I continued this relationship for
several years until I moved again.

We eventually got all of the others into it too, but those are other
stories.....  Shall I tell them too?