Date: Wed, 14 Aug 2019 16:29:25 +0000 (UTC)
From: Mike Simmons <illuminati12353@yahoo.com>
Subject: It was always about the bets 5

I woke up early as usual got dressed and went for my morning run. The whole
time thinking about my day and how I was going to change things. When I got
home dad was leaving for the office and mom was, well wherever the fuck she
was. I grabbed a glass of juice and went up to shower and tried to figure
things out. Fuck that did not last long as my phone rang and it was Ray
asking me to come over and complete my task. I told him I was busy, told me
I needed to bring my enema equipment and to get here as soon as I could. I
said fuck dude this has to stop and he said cut the crap and let's get this
done, I'm alone for a while.

I dried off put a pair of shorts on and a tee and started over. I walked in
and he asked for the enema stuff and told me to get into the bathroom and
undress, which I did. He said he was going to give me the same enema I gave
him and that then he would then shove a butt plug up my ass and that I had
to hold it sitting on the commode for 5 minutes while he watched. I looked
at the butt plug and fucking freaked out, I had never seen one and it was
fucking huge. I started to get dressed. He started to get physical and
grabbed my hair and I took a swing at him and hit him in the stomach. He
laughed and said really dude, just fucking stop and get to it. The bet was
I had to hold all that in for 5 minutes while sitting on the toilet. Just
like I did he lubed my ass and stuck a finger in then started with the 5
enemas. When that was complete he said get up on all fours and now the fun
starts. He put more lube on my hole set the plug in place and said breather
fucker this is going to hurt and he pushed and I screamed. Get that sorry
ass up and sit on the commode. He started a stopwatch and the agony slowly
built. My ass hurt and was stretched and the fucking cramping started at 3
minutes. He could see I was struggling and was laughing at me. Then he
reached for my nips and squeezed, I slapped his hands away and told him
that was not part of the deal, but the distraction helped. At 4 minutes I
was really suffering but was determined and Ray was starting to get
nervous. Finally, it was over and the plug and the enema was still in
place. I told Ray to reach behind me and pull the plug out, he laughed and
said I'm not getting your shit all over my hand and left the bathroom. I
pulled the plug out and fuck did that hurt and the enema squirted all over
the toilet. I cleaned up got dressed and went to Ray's room to find him
sitting on the bed with his hands covering his face sobbing. He looked up
and asked, what's the next task. I told him there would be one and he would
not like it as he totally wrecked my ass but I needed a couple of days to
sort things out in my head. I pulled him to his feet gave him a hug and
said dude " BIG GIRLS DON'T CRY" and I hope you are a big enough girl to
deal with what you will have to do next. Enjoy the three or four day
reprieve. Oh and clean the bathroom before you parents come home, laughing
I left.

I barely made it home when I had to shit again and now I was really pissed.
My hole was so stretched I was leaking. Not exactly the start of the day I
had planned but it was time to deal with Tammy. I called left a message and
she called right back. I told her we had to talk and asked when she would
be free. She replied somewhere private and be prepared. I said somewhere
public would be better and she said fine, but was clearly unhappy. I
suggested Barnes and Noble's at South Hills Village. She reluctantly agreed
and said noon which was great as I could get to the weight room at school
mid afternoon. When I arrived she was at a table drinking iced coffee, I
ordered juice and sat down. She said what up and I said we needed to talk
about the other night and your new interest in getting into my pants. I
told her I thought that out of the blue she was moving pretty fast and ask
why the change. She said because she was on the pill now and everyone was
doing it and she wanted it with me. I said what if I wasn't ready and her
reply was you are the only 16 yeas old guy who isn't ready. I told her
besides my car was not where I wanted to have sex for the first time. She
said fine my place tonight the rents are going out and the bratty brother
was at a friends place for the night. I told he no, I was not up for that,
she quietly said fuck off fag and stormed out.

I was actually relieved. I went to school and worked out and was pleased
that Ray was not around. In the shower our QB, Jeff, came buy and asked if
I was free for a while and he wanted to chat. I was glad for the change of
people around me. We went to McDonalds, I had a salad and he had a Big
Mac. We chatted about things football, girls, school, very low key and
relaxing. On our way out he said there was a party at his place Friday
night and asked if I wanted to come and bring Tammy. I said I would be glad
to come but someone else would have to bring Tammy as we broke up this
afternoon. He slapped me on the back and said dude there is a line of
chicks waiting for that to happen.

I had a few calls from Ray but was ignoring them and even though I knew it
was probably too late I called the school guidance office, I wanted to set
up an appointment. To my surprise the secretary answered and I told her who
I was and that I would like an appointment. She said Mr. Durham would be
available tomorrow in the morning and if I could stop in around 9:30 that
would be perfect, she would pull my records and have that ready for him in
the morning. Just two thing more to do, Coach and Ray. I called coach first
and told him I had talked with my dad and that football next level was an
interesting thing, but that education was the priority. I asked which
schools had contacted hi, and he said WVU, Pitt and Penn State, IUP and Cal
I was blown away, local interest and that made sense for an unproven
junior. I asked that he refer all that stuff to my dad and provided his
work number. I told him I was all about having fun working hard and having
a great season. He said one mort thing, think about moving to linebacker,
fuck the gremlins keep coming without stopping. Coach why would we do that?
His reply was that the interest was because of size and physical play not
my running ability, I was very fast for a linebacker but only fast for a
HB. I asked what's best for your team and he said we will see.

Now I had to deal with Ray. I called and he picked up on the first ring,
dude where have you been. I replied busy what's so fucking important. He
said we have to talk and I said I have been doing a lot of that today and I
needed a break. If he wanted to hang out and chill I was cool but nothing
serious. I told him my parents were home and we had to cool the drinking.
He said fine and I told him I was not discussing anything serious,
especially the stupid fucked up bets. He agreed and I told him I had a
Tammy story to tell hi. He said he would stop over after dinner.

Ray came around 7:30 and we just sat and had a friendly chat. I told him
About Tammy and he laughed out loud. So you turned down sex with her
tonight to be with me, you are a sick puppy, I laughed and said I was just
not into her that much. We played videos for a while and around 11:00 he
got up to leave. He said he enjoyed the stress free night, but that we
needed to talk, I said I know and we will but you started this shit with
the uncomfortable bets. He smiled and said I know but on a weird and sick
level it is fun. I had to agree on some level but I needed a break and it
was going to get real serious. I told him I had a 9:30 meeting at school
and we could talk after we worked out. I told him I would be there earlier
around 11:00. He said that worked and we could go somewhere where we would
not be disturbed after the workout. Dude, just pick a place and let me
know, I can't deal with much more.

The next morning I ran ate breakfast and went to meet Mr. Durham at school.
When I got there he came out from his office to greet me and said damn,
what happened to you your so much bigger. He open my folder looked over my
grades and activities. He said excellent grades, football and not much else
you need volunteer work and extracurricular activities. Basically you can
do whatever you decide. He ask about my interests and I discovered I am
very limited. He suggested we schedule an aptitude test first week of
school and go from there. I thanked him for his time and left for the
workout.

Ray and I drove each other hard and pushed each other, I was fucking
exhausted. We showered and Ray suggested we just sit in the stadium. We
were alone, most certainly, and he asked what his next task would be. I
stopped him and asked how comfortable he was so far and did he want to
stop. He replied he didn't. I asked again if he wanted to end this and
simply have sex. He said no that would not work for him. I said fine but
after the butt plug thing, I was raising the stakes quite a bit. Romantic
sex would be easier on him but I was willing to just do it and not care
about his feelings or comfort or lack of comfort. He said fine but that
would also apply to you, Mike. I told him I was less comfortable with these
games and I understood but needed to slow the tasks down time wise, once a
week at the most. He agreed, I asked agin are you sure and he said yes
what's the task. I told him he would be naked on all fours on a bed or on
his back holding his legs up, I would lube his ass and fuck the shit out of
him. He would have to give himself an enema to clean out and I was not
using a condom. Finally, when I shot my load in his ass my cock was going
right to his mouth. He just sat there a minute then said when and where. I
reminded him he needed to be sober. Then I asked what his thoughts were.
His reply shocked me, dude I knew it would get to that eventually and as
long as it is something I have to do to keep my word and not my choice, I
am good. So I said you are going to just take it hard up the ass when there
were other options. I asked, what if the task was romantic sex and he said
the same thought process applied. Time and place to be determined.j

To be continued and please provide some feedback.


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