Date: Fri, 24 Jan 2020 18:59:45 +0000 (UTC)
From: Mike Simmons <illuminati12353@yahoo.com>
Subject: It was always about the bets 84

Once at home, I immediately started packing for the trip and just started
laughing as nothing from last time remotely fit. Well I guess new ski pants
and a coat were in order. That could easily be fixed at the resort. The
rest was easy and as I was just about to shower and shave Carrie called.
She said Mike thanks for the best Christmas ever. She said that here
parents are no longer stressed over us and that she loved me and hoped I
had a great time on the ski trip. We exchanged I love yours and hung up.

I took a shower and jumped into bed set the alarm and struggled to fall
asleep. I don't know when I drifted off but was startled when the alarm
woke me and I quickly changed into warm clothes loaded the car with my
clothes and some beer and went to Jim's. He was ready and had two cases of
beer and we loaded the car and it was off for some fun. We talked about our
day yesterday and he said he got a gold necklace from Ashley and I laughed
saying I'm betting it matches the one I got. He said Mike no way so it's a
bet.

I reminded him about the rules going forward and that there always had to
be a real bet. Then I mentioned Ryan and his friend from high school would
be up today for one night. He said, shit that will be interesting. The ride
was 90 minutes and was uneventful as we listened ot some rock music and
chatted. At the lodge, I checked in and they said the condo would be ready
at noon, so we bought 3 day lift tickets, rented skis and I went and bought
a new jacket and pants, changed in a rest room and hit the slopes. We
started on an easy trail and after a few times Jim said he thought we were
ready for something more difficult. We got off the lift and started down an
easier slope but no trail and it was a bit of a challenge but reasonable.
After two trips down I suggested a break and we secured the equipment and
went inside for some coffee.

As we were sitting there I noticed a couple of girls looking at us and
trying not to be obvious. I mentioned that to Jim and he said, dude I saw
that as well but be cool, let's ski some more. We got on the lift and tried
a couple of different slopes and I was getting tired and I said Jim, how
about another break and then to the condo? He said great and we went inside
had another coffee and decided to explore the joint. We found the swimming
pool and checked it out then checked out the restaurants. With that all
done I got directions to the condo and the keys. As we were driving, I
called Ryan and it went to voice mail and I left a message asking where he
was. As we were pulling into the condo Ryan called back and he said they
were taking a break and had been skiing all morning. I gave him the
information and said bring you skis with you and said we would be there for
an hour or so.

We unpacked the car, refrigerated the beer and chose the biggest room for
the two of us. That left a smaller but adequate room for Ryan and Jason. I
opened a beer and and said so Jim where are with girls and sex and he said
Mike like you that's complicated, but it will be what it becomes and I said
well I bet judging from this morning we will both be unfaithful. He said we
already have one bet but I'm not taking that one. So let's compare the
necklaces. Damn, I was right they were identical. I said wingman we need to
control our woman, but perfect you owe me a task and I have not shot a load
in three days. He said shit.

Just then Ryan and Jason came in and we each had a beer and I told them
what room they had and that if that was uncomfortable there were sofa beds
that would work. Jason looked at Jim and I and said fuck Ryan why didn't
you tell me we would be with two ripped dudes. Ryan said Jason cool it,
they are both 17 so slow down. I took that as a hint to get out of Dodge
and said Jim let's find the slopes. Outside we put on our skis and shit we
were at the top of one of the more difficult slopes and I simply started
down going a good bit sideways making slow big turns. Once at the bottom we
went back up to the easier slopes and around 3:00 I was beat so it was
another break and a hot dog and a soft drink. The same girls were there and
two came over and asked if they could have a seat. I said sure and that I
am Mike and they said we know you picture was all over the sport pages the
other day. Jim introduced himself and they were Alisa and Madison. I asked
where they went to school and they both said Pitt. I thought good at least
they are legal. We chatted a while and I said Jim let's get a few more runs
in before dinner and he said great. On the way out he said what's with the
quick exit and I said dude it is two early and they will follow us the
whole time we are here and I don't want to be the jock fuck of the week,
well at least not on day one. We did three more runs and took the lift
nearest to the condo. Going inside we found Ryan and Jason sitting on the
sofa making out. I just walked past and went to our room and changed into a
tee shirt and shorts and Jim did pretty much the same. Jason looked and his
eyes got real big. I said guys don't let us stop you and Jim and I opened a
beer and sat down like they were not in the room.

After a few minutes Jason asked, so what the deal with you two? I said we
are each others wingmen. Jim looked at me and I nodded and he said Ryan, I
believe you owe me a task, your room now please. Ryan and Jim left the room
and it was me and Jason. I said dude here is the deal, we bet on almost
anything and the looser does whatever the winner wants and it goes from
tame sex to very wild sex. He smiled and said so Mike what's the bet? I
said flip a coin.

He did and I called heads and it was tails. I said Jason there is a condom
rule so be warned. We went into the empty bedroom and we both stripped and
he was running his hands all over me. Then he pulled me into an embrace and
started to kiss and I returned the kiss and then he put his hands on my
shoulders and pushed me on my knees. He just stood that and I waited and he
finally said for Christ sake suck my cock. He was about 6 inches so I
swallowed him hole and he was moaning and after a while he pushed me away
and said where are the damn condoms and I produced the condoms and lube and
he put a condom on and said I'm not using lube and he said on your back on
the bed. He lifted my legs and spit on my hole and drove it home to the
hilt and I grunted and he started pounding my ass, hard and fast. Then he
pulled out and just stood there and then dove in again and really pounded
me. Finally he screamed, fuck I'm going to cum and he filled the condom and
collapsed on me. We kissed and made out some and then he stood up and I
removed the condom and got up and took a shower.

Back in the common room Ryan and Jim were there and Ryan said so I guess
everyone is good? I said, guys, I'm good and I'm going for a swim and Jim
said he was in. Ryan and Jason were staying in.  Jim and I drove to the
lodge, found the pool changed into swim trunks and a tee and found a lounge
chair and were just chatting and damn every woman in the place was looking
at us. I got up took off my tee and jumped in and started doing laps,
something I had not done in ages. Jim joined me and was also doing laps. I
was watching him and he stopped and we were standing there talking. I got
out and walked to the lounge chair I looked at every chick in the place and
then just sat down, Jim was watching and did the same. I had to piss so I
got up went to the changing room and again looked at every chick in the
area. When I came back there was a girl chatting with Jim. I simply sat in
my chair and listened. Then I heard Jim say babe, you up for a three way
with my buddy? She looked at me and said with him as the third and Jim said
yes. Damn he is every much as ripped as you. Well, how about a 4 way? I
asked a real 4 way or individual couples and she said a real 4 way with
cock and pussy in every mouth. Then she said we are both bi and I asked
what school they went to and she said we both go to Penn State in State
College and we are both bi. Jim said well he goes to CMU and I go to
Pitt. I said so our condo or your room? She said our room it is closer, she
gave us the room number and we said we would be there directly after a
quick shower.

I said wingman, do we have condoms? He said Michael I got it covered and we
both laughed. We found the room and another hot chick answered the door and
she said damn Tracy chose well and she grabbed Jim and started taking his
clothes off. Just then Tracy came in and started on me and before I knew
what was happening she was sucking my cock. Then there was 4 of us on the
bed and there Wes pussy eating cock sucking and switching and it was
intense and hot and then Tracy said ok dude fuck you friend and I said I
want you and she said eventually but him first and I'm eating your ass and
he his getting sucked while you fuck him. Man that was intense and Jim
produced a condom and lube and it was game on. I was pounding him good and
and it was awesome to have my ass licked and sucked and I was betting Jim
was going to shoot in her mouth. We were a sweaty mess when it was over and
I looked at Tracy and said your turn and she smiled and said guys that was
fun but we are done get dressed and get out of here, our boyfriends are due
back in 30 minutes. I said shit and we dressed and out in a flash and did
not say a word until we were in the car. I said wingman did we actually
have sex with a chick or each other and he said, who the fuck cares that
was awesome.

Back at the condo Ryan and Jason were watching TV and Jim and I got a beer
and joined them. Ryan asked how was the swim and Jim said it was great, all
eyes were on the two of us. He laughed and said so you two are either used
up or horny and Jim answered yes and lit a cigarette. I got up went into
the bedroom and called Carrie, she answered immediately and said I was
hoping you would call. She asked about my day and I said we were on the
slopes all morning, lunch, back to the slopes, swimming and I was about to
go to bed. She laughed when I told her about the clothes. I asked about her
day and she said Mike, it is family shit and it's ok. Then she said Sam and
Jennie broke up and he is a mess and said it was your fault as you told him
not to have sex. Well tell him to call me around this time tomorrow. Good
night and I love you.

Then Jim got up went into the room and was gone about 10 minutes and I ask
if was checking in as well and he said yup. Jason said you guys must have
had fun to hurry back and check in with the woman and he laughed. With that
I lit a cigarette and thought he was right, but I didn't have sex, with
another woman, I just fucked Jim. I said so when you two leaving tomorrow
and Ryan said well after dinner as Jason has to be back the next day and it
is a long drive. Since nothing seemed to be going on I got another beer and
lit a cigarette thinking damn I'm tired. Just then Ryan said, guys Jason
and I want to have a 4 way with both us serving you two, how do we get to
do that? I said lose a bet. They talked for a few minutes and Jason said
Mike, why bother we both want fucked so let's just do it. I looked at him
and said because Jim and I are not gay and I need the cover. That's how it
needs to be and a real bet. I got up went into the bathroom and
pissed. When I came out Ryan and Jason were nude. I laughed and said what's
the bet and Ryan said that you will be unable to look at us nude and not
touch us. I looked and Jim and we both stood up and stripped and said well
here we are and no touching. Jason asked and if I do? I said Jim and I will
deposit you outside and lock the door. I looked at Jason and said dude you
better hurry as you are hard as a rock. I'm betting you can't not touch it
for 30 minutes and if you do we all go to bed and sleep. If you go hands
free you win and you can set the task. Oh and Jim and I are going to
everything we can to keep you hard without touching you. He said deal. Jim
and I stood got real close to him and started to make out and I was wagging
my cock in his face. We kept this up and he was leaking but not touching. I
finally gave up rubbed his head and said nice job and her shot he shoe a
load all over the place and I laughed.

I said ok Jason, I cheated by rubbing your hair so if you want you win and
we can do whatever you decide. He said I want you to fuck me while Ryan is
fucking you and Jim is fucking Ryan. And to get that done sucking all
around. Do we have enough condoms for that and Jim said absolutely. He got
up pulled my shorts down and got on his knees and started suckling. Jim got
the rubbers and the lube and Ryan started sucking him. They were apparently
ready and hard as a rock. I pushed Jason away and had him lean over the
table, lubed him up and at the same time Ryan and Jim were doing the
same. I figured what the hell and just went balls deep and soon enough Ryan
was in me and getting a rhythm was hard but interesting. I had never fucked
before while having a dick in my ass. It went on like that for a while
until I heard Ryan say shit I'm going to cum. It was only a minute before I
shot a load and Jim having the advantage of being the last in line shot
last. It was fun but the gils were better. We got dressed and I had two
more beers. I was pretty beat so announced that I was done for the day and
said that I was going to bed and we could all go to breakfast, just ski to
the lodge. Jim said good night and we both went to our room. In the room he
stripped and said that we were both sleeping nude and that if there was sex
during the night it was bareback and no bets. I stripped, climbed into bed
and was almost instantly asleep. I woke at about 3:00 needing to piss and I
thought what the hell and grabbed the lube and carefully and quietly lubed
his ass and slowly entered is ass. He moaned and said please just do me and
let me sleep. I was slow fucking him and he was moaning saying wingman
shoot that load and he reached for my nips and I shot instantly. He rolled
over and said dude in the morning I will not be so nice in the morning. I
kissed him and said dude, I've done you twice tonight it's your turn and I
fell asleep.

True to his word, he was up early and I woke to a cold feeling in my ass
and damn he went right to it. It was hard, fast and intense and very
physical and he even spanked my ass. It was soon followed by a big load. I
rolled over kissed him and said, wingman I bet you had fun. He said that no
bet but it was fun. Then he said, Mike I like the wingman thing where there
are no bets and just as needed. Jim, please bets always. It has to be
always about the bets.

Ok Mike, I'll agree to that but I need something from you? Jim for Christ
sake just ask and I'll do it. Mike, when we go to VT can I please leave my
dad at home? Jim, that's your call and my dad will be there to help and can
spend time with him to keep him occupied. Jim and you rooming with a
player? He said yes the starting QB he will be a senior next year and
thought damn. Oh, Jim congrats on being 2nd team all state. That was a big
deal. So your dad and should go, separate cars and my dad will occupy him
and keep him out of your way, does that work? Jim said sure, that's
fair. Then I asked if he was going to visit Michigan? He said, Mike it
depends on this trip. It was my turn to say good enough and that I would go
to Michigan with him no matter what. Dressed for skiing I pounded on Ryan's
door and said breakfast at the main dining room at the lodge in 30 or eat
alone. Jim and I grabbed our skis and managed that tough slope secured our
skis and went to eat. I asked for a table for 4 and Jim and I sat down and
ordered coffee.

We were about half way through breakfast and Ryan and Jason appeared. They
looked a little out of sorts and I asked guys, what's up? Jason said, well
we were up most of last night fucking and we are both tired. I laughed and
said join the club. Jim and I finished and I added the bill to the condo
bill and hit the slopes and it was a perfect morning and the lift lines
were a little long so we stopped for coffee. The girls from yesterday
stopped by and asked if we were up for more fun this afternoon and Jim
said, that depends on who is getting fucked. They said well like yesterday
and Jim replied no thanks and went to the men's room. They asked me what
was his problem and I said, girls like me he want pussy so unless you are
willing to provide that we are not interested, enjoy your day. Then I got
up and joined Jim in the rest room.

We were back on the slopes and having a blast, raced some, spent time on
the more difficult slopes and after a couple of hours, I said Jim I need a
break, condo or lodge and he said definitely the condo. We sat on the sofa
and put some music on and fell asleep. I looked at Jim and said, wingman
dinner and then slopes or pool and he said pool. We got in the car drove to
the lodge and ordered the buffet. We finished and Jim producer credit card
and paid for dinner. He looked at me smiled and said dude, I have money
too. I gently punched his arm and we went to the pool. It was pretty much
the same scene as the chicks and a few guys were eying us. I said, Jim what
do you think? Guys, girls or neither? He said wingman, just you. I laughed
and jumped into the water and was doing laps when I bumped into something
and it turned out to be a hot check. I apologized and she laughed and said
dude you can bump into me anytime.  I started to swim away and she said
Mike, don't you recognize me, I'm Samantha? I just looked and she said
don't you remember the fun we had with Jeff? I laughed and said yes, I do
so how is Jeff? Mike, he is out of the reform school and was in a gang and
was drunk and in an accident and is paralyzed and in a wheelchair, unable
to walk. I said, shit I didn't know all that. Where is he? She replied
Butler with his dad. Then I asked, Sam where are you and she said we moved
to the north hills, want to party? I laughed again and babe I have become a
one trick pony. She laughed and said damn Carrie is a lucky bitch,

Back at the lounge chairs, I told Jim about Jeff and said damn, that sucks
and jumped in the water. About 5 minutes later he came back asking if I was
up for a three way and I said, dude I'll pass, but feel free and off he
went. I was laying there and drifting off and this girl came up and ask if
the chair was free and I replied sure. A little while later she asked me if
I wanted a drink and I said, I'm fine and under age. She laughed and said
well I have beer in my room. I looked at her and thought she must be mid
20's and I said so what else is in your room? She said whatever you want, I
like young ripped jocks and you and you friend are every bit of that. She
tossed me a room key and said I'll be there for an hour and if you chose
otherwise, return the key to the desk. I sat there for a few minutes and
decided to change and go to the arcade, in the changing room I found a not
in my jeans with a room number and a few condoms. I looked at the key I got
and saw that it was s the same room number as the note and figured what the
fuck. I simply used the key and found Jim and this woman sitting on the bed
talking.

I looked at Jim and said ok, what's up? Mike she likes it tough and wants
one her ass and one in her cunt, you chose? I looked at her and said how
about we each do you twice? She laughed and said if you two studs are up to
it, great. I said bitch where is the beer? She got up and I grabbed and
said so bitch how rough? She went to the closet and produced cuffs, a
flogger and a ball gag and tossed them to me and said so tough guy, you
know how to use those. I grabbed her and said wingman help me get this
bitch naked. I threw her on the bed and Jim yanked her pants and g-string
off and I tore her top off and cuffed her hands in front of her. Threw her
back on the bed and said no where is my beer? She indicated the
refrigerator and I grabbed two beers and Jim and I sat in the bed and
drank. She laughed and said is that all you wanted is beer? I got up found
and inserted the ball gag and opened another beer.

We just sat talking and there was a knock on the door and I looked at Jim
and went and answered the door. There was a dude there and he laughed and
said you guys have fun? I said no she isn't our type and we simply
undressed her and got her ready for you, mind if we watch? He said sure,
flipper her over and started with the flogger and fuck her back was red and
her ass was black and blue and he was crying. I motioned to Jim and we got
up and left? He followed and in the hall asked, Mike how did you know? I
said wingman, I didn't and was flying by the seat of my pants, let's get
out of here. On the short drive to the condo we decided that the pool was
off limits for the rest of the trip.

Back in the condo I stripped to my boxer briefs and lit the fake fireplace
and turned on a college football game. It was a meaningless game and we
watched with little interest. I stood up stretched and said wingman, I'm
bored! He laughed and said bedroom. On your stomach and he started to give
me a wonderful back rub. Then he said your turn and I returned the
favor. We just laid there in our underwear talking. I said wingman you
having fun? He said Mike, I am but to be honest I miss Ash. I laughed and
said dude I miss Carrie as well. I'm guessing that's why we have not had
sex with a girl, even though we thought we did.

We got dressed and went back down to the lodge and were walking around, got
a apple cider and were sitting by the fireplace and the dude from earlier
said guys her door is unlocked and she is still cuffed and now tied to the
bed you should go deposit a load or two I her cunt. I looked at Jim and
said wingman no way and he laughed and then two chicks very near our age
came up and started chatting. They asked how long we were staying and I
replied two more nights. They asked if we wanted to ski together tomorrow
and I said how about breakfast at 8:00 in the lodge and we could ski all
morning. They said well 8:30 and they would see us then. I said, sit a
while and let's chat? They sat down and we found out they were seniors in
high school in a neighboring district. I said so I'm guessing you know who
we are and they both laughed and said yup, QB and mister everything. I
laughed and said that's Jim and Mike and you are? They said Jane and
Melissa. I asked where they were staying they said with their rents and
would be here till New Years. We talked for a while and then they said
goodnight and walking to the car Jim said damn that was different and I
said wingman, they will be naked in the condo by lunchtime tomorrow, if we
are up for it. Back in the condo, I grabbed a beer and lit a cigarette and
said, so Jim you up for fucking one of those girls? He changed the subject
and we talked for a while and out of the blue said Mike, I don't know. Jim,
neither do I but it will be what it becomes, I'm going to bed. You can
sleep in Ryan's dirty sheets or sleep with me and I mean sleep. I got up
went in the room stripped naked and Jim joined me a minute later.

Comments are encouraged as this is my first story.

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