Date: Fri, 15 Jun 2018 22:06:46 -0400
From: Thomas Abrams <thomasabr17@gmail.com>
Subject: The Straight Massage - Part 4 and the end

The Straight Massage is a Gay High School story.

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The Straight Massage - Part 4

It took Simon a minute to figure out what Thomas was doing.  Right after
Thomas pulled his ass cheeks apart, Simon knew that Thomas could see his
hole.  He really was conflicted at the thought.  He was totally exposed to
his friend.  He also didn't know exactly what was about to happen.  He
figured that Thomas was going to massage him there.  Then it dawned on him
what to do.  Simon reached down to the front of his briefs and slipped them
over the head of his dick.  He gently pushed them down so that they were
now as low as the top of his knees.  There was no doubt now that he had
totally and purposely exposed his entire ass to Thomas' view.  He never
said a word, but by pushing down his briefs, he clearly signaled to Thomas
that he was okay with what was happening.  Or at least if he was not okay
with it, he was not going to object.

Thomas was stunned when Simon pulled off his underwear.  He never expected
to get this far much less get a clear signal from Simon that he could
continue.  But given the signal, he definitely was going to take full
advantage.  He made sure that his finger had a lot of oil and reached right
down the middle of Simon's crack.  He did not actually push his finger in,
but played with the edges of the hole for a while.  He held his ass cheecks
apart so that he had a good view.

Each time he brought his finger back to Simon's hole, he made sure to rub
it over the hole.  He also made sure to have a lot of oil on his slick
fingers.  He did not want to hurt Simon even a tiny bit.  He was sure he
had been touching his hole for several minutes when he finally pressed the
tip through the opening.  Because he had so much oil, there was almost no
resistance.  He kept doing this and each time he returned with his finger
tip, he pressed it in a little further.  He kep his tip flat so that he was
rubbing more along the opening rather than just going straight into it.

He knew that this would take him longer, but would also have the effect of
opening Simon up wider.  He was not in any rush, and was really enjoying
the veiw.  Before he realized it, he was in up to the first knuckle.  That
was far enough that he could feel Simon's interior ring holding him back
from going in further.

Simon was really having a hard time.  The feelings were intense.  He knew
that he was on the verge of cumming.  He did not want to do that and have
Thomas see it happen.  He knew he would have to do something especially
when Thomas got right to the opening in his ass.  Those feelings were
intensely hot.

Thomas could not hold back any longer.  It was time to go for broke.  With
one hand, he removed his shirt, shorts and underwear.  He put oil all over
his dick and lots on his dick head.  He slowly removed his finger and
poured a couple more drops of oil right in his opening.  That was the most
lube he tought he would ever be able to get inside Simon.

Simon did not have any way to stop it when Thomas grabbed both sides of his
body and flipped him over.  Again, before he realized what was happening,
he had been turned over onto his back.  His six inch dick was totally
dripping and covered with precum.  And the worst part of all is Thomas
could see him.  As he glanced down, he had another huge shock.  Thomas was
totally naked and had his dick pointing straight out.  He was a good seven
inches and very very hard.

He was almost in shock seeing it.  The veins were poking out Thomas was so
hard.  He felt like he was in a trance as Thomas slowly guided it to
Simon's ass.  He became keenly aware that Thomas' dick head was about to go
in has ass as soon as Thomas touched it to Simon's hole.  Thomas was going
so slow that Simon could have stopped him at any time.  To this day, he
really does not know why he didn't stop him.  He had never even considered
gay sex at all, much less being the bottom.

Thomas did not even press in at first.  He simply made sure that the head
was lined up properly and resting against Simon.  He left it there for
about ten seconds to make sure that Simon had every chance to make him
stop.  When Simon did not do anything, Thomas becan to apply a small amount
of pressure.  With all the inital work he had done with his fingers,
Simon's outer ass opening was very oily and relaxed.  The entire head of
Thomas' dick went inside with no resistance.  After about an inch got
through the opening, he felt Simon's ring blocking further entry.

Thomas did not want to hurt Simon.  He wanted to make sure he enjoyed this
because he really wanted to do this more than once.  It took the greatest
of control, but he pulled back about one half of and inch so that just his
head stayed in and then pushed back in slowly.  Only about one half to
three quarters of an inch was going back and forth.  The feeling was
amazing to Thomas.  He had done some gay stuff before but never had been
able to fuck a guy.

He almost could not keep from cumming.  Twice he had to stop moving or he
would not have been able to stop.  He was making a ton of pre-cum and knew
that a lot was going inside Simon's hole.  The third time he started back
moving, he could not believe that Simon's inner ring just let him go right
in.  There was no resistance at all.  It was as if Simon's ass wanted his
cock to hit bottom.  He kept going slowly, but never stopped until he was
all the way in.  All seven inches was totally inside.

When he pulled back out this time, he started going much faster and harder.
He knew that he could make it in and not hurt Simon so he sped up to enjoy
the feelings even stronger.

Simon never said a word, but just was trying to feel the dick in his ass.
Thomas was clearly enjoying what he was doing.  So much so that he had to
stop.  Simon knew that meant that Thomas was on the verge of cumming.  He
wondered if Thomas would pull out and shoot on Simon's stomach.  Thomas
stopped moving once and then again.  Simon was guessing that Thomas had
been inside his hole about five minutes or so.  He really had no idea.

When Thomas started moving for the third time, Simon just felt the dick
keep going in and in and in.  He didn't hurt, but was definitely full.  As
Thomas pulled back and started back in, he felt Thomas speed up.  Simon
lost track of time as he was overwhelmed with the feeling of a dick in his
ass.  Until finally it happened.  Thomas pushed in and stopped moving.

It was not because Thomas was about to cum. It was because he was already
cumming.  Simon could actually feel every spurt and throb of Thomas' dick.
And right after the throb, he could feel the warm liquid going into his
ass.  He guessed he received a total of five or six spurts before Thomas
stopped cumming.

As soon as Thomas finished, he slowly pulled his dick totally out of Simon.
It was as if a chill entered the room at that point.  Simon became very
self conscious about knowing that he had let his friend fuck him.  He also
knew that it was something he had never wanted, but it was also something
that he had allowed to happen.  All kinds of feelings were going through
his head.

Thomas could tell that Simon was coming down from the sexual bliss.  Thomas
was also, but was incredibly satisfied.  When he looked Simon in the eyes,
Simon looked down and would not keep eye contact.  So Thomas did what
typically happens after awkward sex.  He said, "Thanks.  That felt great."
And then quickly added that he needed a shower.

As fast as he could gather his clothes, he went to the bathroom and took a
shower.  When he came out, he was fully dressed including his shoes.  Simon
was not in the room.  Simon had also gotten dressed as soon as Thomas went
into the bathroom and left the house.  He did not return until very late
that night.  He quietly came in their apartment and went to bed.  He made
sure that he was quiet so that he would not have to talk to Thomas.

End of part 4. End of story.

Author's note: This story is slightly changed from what really happened to
me a few years ago.  It is as close to how I can remember the details.
Maybe I can get up the courage to share the next few weeks after the
encounter with Thomas, but even after several years, it is still a very
painful memory.

I have reconciled myself to know that I am not as straight as I thought I
was.  Other than a second event with Thomas, I did not have another
encounter with a guy for almost three years.  As a piece of advice for
anyone who is struggling with their sexuality, I would strongly ask that
you think things through before you act.  I did not and it caused me a good
deal of pain.  I am very comfortable with myself now, but it has taken a
while.  Enjoy your self, enjoy your life.  Be happy.

Thanks for reading my story.

Simon