This erotic literature contains explicit sexual 
content and should only be read by adults. If reading 
descriptions of explicit sexual activity would in any 
way be offensive to you or illegal for you to do, you 
must stop reading this immediately. Continuing to read 
beyond this point is your agreement that you are aware 
of what lies ahead and legally allowed to read this 
material. Thank you.  
 
The author of this story (Mikes_Fantasies) reserves 
all rights to this story--reproducing this story 
without the author's permission is prohibited



The Usual Wager (MMM, cons, anal)

Author:  Mikes_Fantasies

July 2004

While we were young and in college in the early 70's, 
my roommate, Jimmy, and I had a standard wager.  The 
bet could be on anything, from a which elevator would 
arrive first to a football game to an athletic 
contest.  The winner had his choice of the loser's 
mouth or butt, on demand, for sexual satisfaction.  We 
considered ourselves basically heterosexual, but 
enjoyed pleasing each other.  Being very competitive, 
we used this wager often and for convenience we just 
called it "the usual."  The "on demand" factor meant 
anywhere, anytime the winner wanted it and led to some 
interesting payments.

In those days, before racquetball became popular, we 
played a game called handball.  The concept and the 
court were the same but, instead of racquets, we wore 
leather gloves and hit the ball with our hands.   The 
ball was slightly smaller and more solid to slow it 
down a bit.  Jimmy and I were both pretty fair players 
and pretty evenly matched.  We often bet the usual.  
Handball is usually played one-on-one but can also be 
played with two-person teams or three people can 
compete in a game called cutthroat.  One day we played 
cutthroat with a mutual friend named Jack.

The courts are completely enclosed.  There is a door 
at the back of the court, flush with the wall, with a 
small window for viewing.  It was a hot day and we 
quickly worked up a sweat.  Our shirts came off after 
the first game.  I enjoyed watching Jimmy and Jack's 
trim bodies as their muscles worked and sweat made 
their skin shine.  Jack was also a pretty good player 
and after three games, it was one win each.  

As we were about to start the last game, Jimmy glanced 
over his shoulder at me and asked, "The usual?"  

"Of course," I said.  

Jack looked confused, but didn't say anything.

The game was close all the way to the end, with the 
lead changing hands several times.  After the final 
serve, Jimmy won with 21 points, Jack had 19 and I 
trailed with 18.  We shook hands and I went to the 
back corner to pick up my shirt.  In my wildest 
dreams, I never expected what happened next.

Jimmy said to Jack, "Mike and I had a small wager on 
this last game and he lost.  Since you came in second, 
that means he lost to you too.  Would you like part of 
the payoff?"

My eyes got wide as I looked over at the two of them. 

Jack said, "Sure, what did I win?"

Jimmy explained that our standard bet included anal or 
oral sex, on demand.  Jimmy said, "I intend to get 
mine now.  You're welcome to join me if you want."  

From the way Jack was looking at me and smiling, I 
could tell that he definitely wanted.  

"Why don't you hit the ball around while Jack and I 
decide how we want to collect," Jimmy said to me.  The 
sound of play would keep other players from entering 
the court.

As I hit the ball against the wall, I listened to 
Jimmy and Jack discussing my payment.  I knew what 
Jimmy wanted.  He always wanted my ass.  He and Jack 
debated the merits of taking me together, one in my 
mouth and one in my butt, or separately.  

In the end Jack said, "I want to fuck his butt, too.  
Let's play one volley to see who goes first."

Jack served but Jimmy won the volley.  Jimmy said, 
"I'll go second.  He's all yours.  There is KY in my 
bag.  I'll keep the ball bouncing while you're 
collecting your debt."

Jack and I went to one of the back corners of the 
court, out of sight of the window.  As he pulled the 
lube from Jimmy's bag, he said, "I've been watching 
your butt all afternoon.  I can't wait to sink my cock 
into it."  

He pulled his trunks and jock off, displaying his cock 
and low hanging balls.  "Alright Mikey," he said, 
"Let's get those shorts off, but leave your jockstrap 
on."  

I saw Jimmy smiling as he continued to knock the ball 
against the front wall.

I was getting pretty excited by this point and when I 
pulled my shorts off, it was obvious that I was coming 
to attention in the pouch of my jock.  Jack gave me a 
slap on my right butt cheek and said, "I know I chose 
your butt, but you are going to use your mouth to get 
me hard.  On your knees my boy."

I lowered myself to my knees and took Jack's cock into 
my mouth.  I just held it for a moment and felt him 
begin to stir.  I rubbed my tongue back and forth and 
the stirring immediately turned into serious growth 
and I had a mouth full of hard cock in no time.  Jack 
moaned quietly and pulled himself from between my 
lips.  Without saying a word, he motioned, with the 
tube of KY for me to stand up, turn around and bend 
over.  I placed my hands against the wall and bent at 
the waist, fully offering my ass to Jack.  This was 
well before anyone had heard of AIDs and HIV, so there 
was no fooling around with condoms.  Jimmy squeezed a 
healthy glob of KY onto his fingers and spread it 
between my cheeks.

I sighed as I felt him insert one finger into my anus.  
He moved it in and out slowly then added a second 
finger.  I was breathing heavily when Jack pulled his 
fingers out of me and grasped both of my cheeks, 
spreading them widely.  I felt the head of his cock at 
my anus and, with a smooth but gentle stroke, Jack 
slid it into me.  I tensed slightly but immediately 
relaxed as he held it still for a moment.  When I 
fully relaxed, Jack started pumping, sliding his six 
inch cock in and out of my slippery asshole.  I was 
into it, arching my back and moving back against him, 
taking it all the way into my butt.

After a few minutes, I felt Jack begin to tense.  I 
knew he was going to come soon and I used my sphincter 
to grip his cock even tighter as he worked it in and 
out.  Jack moaned loudly and I felt his cock twitch 
and jump as he shot a load deep into my willing ass.  
He continued pumping until he was totally drained 
inside of me.  

As Jack pulled out of me, Jimmy yelled from across the 
court, "Don't move Mike, I've got something for you, 
too."

Jack pulled his shorts on as Jimmy came over and 
dropped his.  I looked behind me and Jimmy was already 
hard as a rock from watching Jack fuck me.  Let me 
tell you a little about Jimmy's cock.  Fully aroused, 
it is just slightly over seven inches long.  It has a 
huge mushroom shaped head.  This is why Jimmy almost 
always chose my butt as his payoff.  He liked fucking 
me because of the way that big head popped past my 
anus on the way in and out.  I liked that too and I 
also loved the way it felt as it moved back and forth 
against my prostate.

Jimmy came up behind me and placed his hands on my 
shoulders and his cock against my back door.  "I think 
that between the KY and Jack's load of cum, you should 
be pretty well lubed, don't you?"  

"Yes, Jimmy," I managed to gasp.  "I'm ready for you 
to fuck me."  I heard Jack stop hitting the ball in 
order to watch Jimmy slip me his big cock.

"OK then," I heard Jimmy say as his cock head popped 
past my anus and into my willing butt.  I gasped as he 
kept pushing, all the way in, until his balls slapped 
into mine.  

"Oh Jimmy!" I moaned as he pulled back and I felt his 
head massaging my prostate.  

My cock got harder and began twitching wildly.  Jimmy 
slapped my ass a few times as he found his rhythm and 
pumped smoothly in and out of my ass.  After several 
minutes I couldn't take any more and came in my jock 
pouch.  I shot a big load as the spasms continued to 
come from deep inside of me.  The contractions set 
Jimmy off and I felt him come and come deep inside my 
ass.  It felt like the hot jets of cum were shooting 
way up where my stomach should be.  Jimmy always shot 
a big load, but this one seemed even bigger and 
judging from his reaction and the sounds he was 
making, he enjoyed it as much as I did.

"It was a pleasure doing business with you Mikey boy," 
Jimmy said.  

"As always," I replied after I caught my breath.  I 
felt Jimmy's erection starting to fade and he pulled 
it out - the head making another satisfying pop as it 
slid out of my ass.

Jimmy pulled his jock and shorts back on and I slid my 
shorts on as Jack gathered our gear.  I had a wet spot 
on the front of my shorts from where I came in my 
jock, but it was hard to tell it wasn't just sweat.  
We left the court sweaty and tired and began the 
quarter mile walk back to our dorm.  All of that 
humping had pushed some air into my ass and as we were 
walking I felt a little fart coming on and let it go.  
My mistake!  Along with the air came some of the cum 
that had been following gravity lower and lower.  I 
felt it run out of the legs of my shorts and down the 
inside back of my thighs.  Once it started, there was 
no stopping it - my ass was a little stretched at that 
point and I couldn't squeeze tightly enough to stop 
it.  Jimmy and Jack laughed at my predicament and told 
me to just keep walking as we approached our building.

I began getting embarrassed as we walked past guys and 
girls we knew.  Not very many noticed the creamy 
liquid running down my legs, but a few did and I can 
still hear the quiet laughter and see the surprised 
looks when they realized what it was.  

Just "the usual" I thought.