Date: Sun, 26 May 2013 17:20:18 -0700 (PDT)
From: Nathan T. <pleasingtheboys@yahoo.com>
Subject: Slutty Ian is a Slut - Chapter 5

This
is an account of my first sexual experiences with an underage boy. Please feel
free to email me at the above address with any thoughts or comments you may
have about this series. Thanks.

Michael
and I have been best friends since we were juniors in high school, so going on
for about 6 years or so. We acted just like any other best friends would. We
went shopping together, went to the movies, gone out to eat, told each other practically
everything that was going on in our lives, the typical friendship between such close
friends. He was pretty cute. Tall yet scrawny, very pale skin, gray eyes, and
had longer than usual emo-style hair which he dyed jet black. Michael called me
up one day and told me about how he met this hot guy online. They have such great
conversations and could talk for hours upon hours, but the problem was, he
lived in Houston, Texas, which was three and a half hours away from our city. I
gave Michael the typical sigh and groan and totally dismissed it, telling him
that long distance relationships just don't work at all. But then he told me
that the guy wanted him to go up to Houston so they could meet. I instantly screamed
out with excitement, that he should totally go see the guy in Houston and that
I would go with him! Michael goes "you think?!..." "Would it be weird if I
actually went all the way there just to see him though?" I told him that as
long as I went with him it wouldn't be weird. If something bad happened between
them, we could still enjoy ourselves and explore the new city and just live it
up! The reality was however, I didn't really care about him meeting this new
guy nor did I care about what would have happened, all I wanted was to go on a
road trip! Of course I didn't tell him that though. I just really loved road
trips, especially when I wasn't driving. Anyways, Michael began to get excited
about the idea of driving up to Houston. I then told him that, "well since
you'll have your guy when we're there, I want to have my own so I won't feel
out of place, I really don't want to be a third wheel." I briefly told Michael
about Ian once a few weeks back but I didn't get too into it because I didn't
want the judgment. You see, Michael was the hopeless romantic long term
relationship type of guy; he wouldn't go for what I had been doing with Ian. So
I go on to tell him that I wanted to take Ian with us when we went to Houston.
I built Ian up so well, I said that he was so nice and sweet and he wouldn't
complain at all and that he would actually really like him as a friend. It
didn't take long for Michael to agree with Ian coming along, but of course, we
were already making plans for something that wasn't even in the works yet. So
Michael said he'd call the guy and then let me know what he thought.

Later
that day, Michael called me back and said that the guy was really excited to be
finally getting the chance to meet him. Michael also asked him if it would be alright
to bring along a couple friends, he was totally fine with it. So Michael told
me that we would be leaving Saturday morning and that to make sure that myself
and Ian would be ready to go, he really didn't want to be late getting on the
highway. It was only Wednesday so I said it was perfect and that I would tell
Ian about the trip to see if he wanted to come along. I'd then call him back so
we could be certain about everything. Now on this particular day, I had barely
spoken to Ian. There were a few texts in the morning but not really much else.
I ended up calling him instead of texting him just because of the importance of
the situation. It's not like I was asking if he wanted to go to the movies or
something, it was a trip in which we would be gone most of the day into the
night, so Ian had to get permission from his dad. So I called him and he
answered, I went on to ask what he was doing and all that nonsense, and then I
told him about my friend Michael and how he was going to Houston to meet some
boy and that I was tagging along and if he wanted to come along as well. Ian
was totally for it and actually got pretty excited about it, but he said that
he had to ask his dad if he could go, as expected. Ian said that he was going
to ask him right that very second and for me to hold on, and so I did. He put
the phone down and I waited for a little bit until I heard the rustling sounds
of him picking back up the phone. Ian said that he could go! But Ian then told
me that he lied saying that he was going to hang out at his friend's house for
some birthday celebration, but that they planned it for the entire day. His dad
wasn't too alarmed by it so he said sure.

So
this trip would be the first time in a few weeks that I would be seeing Ian,
and that made me very happy. I figured nothing would happen while in Houston so
I began to plan for us to see each other whenever we got back. In the days
before the trip, Michael and I were thinking of how to go about the whole
thing. First we settled that we would be taking his car, which was a white two
door sports car, a Mitsubishi Eclipse, but that we would both split the gas
money and he would drive there but I would drive back. We would be meeting this
guy at the Galleria, which was this huge high-end mall with multiple levels and
a skating rink, right in the center of downtown Houston. I thought it was a
good place for them to meet. I called Ian that Friday to remind him that he
needed to be ready by 10am, and he reassured me that it wouldn't be a problem. Friday
night I was far too excited, I couldn't even sleep. I get to finally see Ian
again and go on a road trip all at the same time?! It was such a good feeling.
Saturday morning couldn't come fast enough. I did end up sleeping for just a
couple hours and my alarm went off at 8am, so I jumped in the shower and got
ready and all that good stuff. I texted Michael to make sure he was getting ready
and of course he was. I texted Ian to make sure he was awake and he said he was
about to jump into the shower. At 9:45am Michael finally picked me up and we
took off to get Ian. He didn't realize how far Ian was until we were driving
for some time, the traffic made it a lot worse. He kept asking if we were close
to which I said yes, but we were still a ways away! We finally made it near
Ian's neighborhood, so I called him and told him to leave his house. I told
Michael that the street we needed to turn on was coming up but he was driving
too fast and we missed it. As we were driving past, I saw that Ian was already standing
right on the corner where I had been picking him up before. He was wearing the
exact same outfit he wore the first time we met, except without the scarf. He
was looking down at his feet kicking around something as we were passing and he
just looked so adorable! I playfully screamed at Michael about missing the
street and he started to jokingly freak out and I said "Ian is all alone and
probably thinks we aren't coming so hurry up!" Michael eventually turned around
and we picked up Ian. Michael then goes "omg he's so adorable look at him!" We
stopped and I had to get out in order for Ian to get into the backseat. Ian
spent the first half of the trip sat right in the middle leaning forward on the
edge of the seat talking to the both of us and they got to know each other.

I
eventually decided to climb to the backseat to spend some quality time with
Ian. I positioned myself so that my back would be on the corner where the seat
and the door met, right behind the driver's seat. I spread my legs so Ian could
scoot in between them and lay against my chest. I wrapped my arms around him
and held him. Almost instantaneously Ian turned his head back to me and we started
to make out. After a few minutes I looked over to Michael but he wasn't paying
attention. I began to grab on Ian's dick and balls through his jeans, making
him so horny, and Ian began to back his ass up into my crotch. I closed in my
legs a bit and positioned Ian on my lap and wrapped my arms around him again and
he just started to really grind on me. He was making me so horny my dick was
getting rock hard. I could have just made him ride my cock right then and
there! But I didn't as Michael began to realize what we were doing and started
to ruin the moment by talking. So Ian got back in between my legs like before
and I held him and we just talked and talked. We finally made it to Houston and
Michael had the directions of where the Galleria was so drove there. It was
such a big place I was surprised by the size of it. We drove around in circles
for a bit because all of the garages charged and Michael didn't want to pay. He
ended up calling the guy and he said to park at the strip mall that was across
the street from the Galleria and that we would all meet at the Starbucks there.
We went and found the strip mall and immediately saw the Starbucks, so we looked
for a space and parked. We all headed inside and figured we would kill time until
the guy showed up so we all ordered something. I ordered an iced green tea. Ian
wanted a java chip frappe so I got him that. Michael got a vanilla frappe.

It
was about 15 minutes until the guy showed up. Michael noticed him as he was
walking up so he stood up from the table we were at. Ian and I then both got up
and followed Michael outside. So Michael finally meets the guy, his name was
Ruben, a good looking muscular guy, somewhat tall, was obviously older than
Michael, maybe in his 30s, but still good looking. They hugged and all that
jazz, then Michael introduced Ian and I and we all shook hands, but I noticed
how this guy was looking at Ian. He seemed to of taken just enough time so that
he could take in what he could of Ian before having to break eye contact. It seriously,
thoroughly, annoyed me. But anyways, Michael and Ruben walked off to the
Galleria to hang out and Ian and I stayed at Starbucks to relax. After maybe 10
minutes, we decided to walk over to the Galleria to see what it was all about.
We had to cross a couple intersections but we finally made it and went in
through what I think was Macy's. We had made it to the mall, or so we thought.
There wasn't really anything around as soon as we passed through Macy's and we
didn't know where to go. There were these stairs with an escalator right in the
middle that went down for a bit, we figured we needed to head down to get to
the shopping area. We walked down quite a ways and what was funny was that
there weren't any other people around. We made it to the bottom and it was just
a big rectangle of walls. To the right were random custodial doors, but to the
far top right were big metal and glass doors. We went over to them and saw that
they led out to a level of a parking garage, which had maybe 3 cars in it.
Obviously we were lost so I just said that we needed to head back up. As I began
walking back, Ian stopped me and stood right in front of me, got in really
close and just looked up at me. I knew what he wanted, so we started to make
out right there, with no one around. I quickly got the idea that since there
were no people coming in and out where we were, that maybe I should stick my
dick in Ian's ass for just a second. I grabbed Ian's hips and crudely turned
him around to which he let out a sexy moan. I reached in front and started to
unbutton his jeans, I pulled his jeans and underwear down just enough so that
they rested just below his butt, then I unbuttoned my jeans and pulled them
down a little to take out my dick and balls. I spat on my hand and rubbed it on
the head of my dick and told Ian to bend over. I guided it to his little hole
and began to press it in, he moaned and moaned but I told him to be quiet, to
which he still moaned! I pressed my dick in enough so that the head popped in
so I began to fuck him with the head only, in and out, in and out, in rapid
motions. I finally let go of my dick and grabbed onto Ian's hips and just stuck
it all the way in! Ian let out a huge groan as I started to really plow this kid's
asshole.

I
couldn't believe what we were doing, and where we were doing it at! I quickly
got scared though that there were cameras around, so I immediately stopped and
took my dick out and told Ian to pull his jeans back up and I did the same. Ian
was annoyed that I did that but I told him we had to leave the area because
there might be cameras watching and I didn't want to get us into trouble! So we
made our way back to the stairs, but we chose to take the escalator instead. Ian
got on before me and I was a couple of steps behind him so his bubble butt was
right in my face, I actually leaned over and bit him on his butt! Ian giggled
and grabbed my head and shoved my face into his ass, it was so adorable! We
eventually found the actual shops and just looked around a lot of the stores,
and yes, it was a very high end mall. We walked all around and saw the skating
rink and all the restaurants. We ended up in Urban Outfitters looking at clothes
and apartment essentials, joking about how we should live together, when I got
a call from Michael asking to meet up. So Ian and I left to go meet them in
front of Chili's, and when we got there, Ruben said that he wanted to take us
all out to this restaurant he knew of that we would really enjoy. We said sure!
We ended up walking around the mall together some more before we left. There
was this instance where Ian was walking in front of us, and I leaned over to
Michaels ear and said, still loudly to where Ian could hear me, "look at his
ass, isn't it big?!" Then Ian proceeded to stick his butt out even more, making
him walk in a funny way, and we all started to laugh! Gosh, I just don't know
how this boy is able to get cuter and cuter. I actually leaned in to smack his
butt after he did that. So anyways, after about 20 minutes, Ruben said that he had
to go back to his apartment since he left his phone charger and credit card
there, plus he wanted to change outfits. So we left the mall and Ruben went off
to his car and the three of us left to Michael's car. Ruben came to where our
car was at and so we followed him.

We
headed to his apartment which was actually pretty close, only a few minutes
from the Galleria. When we pulled into the complex we followed Ruben's car all
the way towards the back and turned right to head to his building, and so he
parked and we parked right next to him. The plan was for all of us to wait in
the car while Ruben ran up to get his stuff, but as soon as Michael turned off
the car, Ian said that he had to use the restroom. So as Ruben was getting out
of his car, Michael, Ian and I got out of the car and Michael sort of hollered
at Ruben that Ian needed to use the bathroom and if he could use his, to which
Ruben said "yeah sure!" Ruben told Ian just to follow him up the stairs, and so
Ian walked off behind Ruben. Michael and I stayed by the car because we figured
they would only be a couple minutes. We weren't really too sure where Ruben's
apartment was at but we quickly noticed that the complex was four stories. We
saw them walk up the outside staircase to the third floor and they walked in through
the corridor of the building. To be very honest, as soon as Ian walked away with
this guy, I started to get really nervous and this sickening feeling began in
the pit of my stomach. Something just didn't feel right. But anyways, Michael
and I just talked about what he and Ruben were talking about earlier and the
vibes he was getting from the guy and just the whole situation. He asked me
what I thought about Ruben and I said that he was a good looking dude and
seemed cool, so if he liked him, I liked him. We talked for a few more minutes
to kill time, but then it turned into a lot of time that we had to kill. It had
been close to 15 minutes that they've been up there. Michael began to worry since
they were taking so long to come back down, and I was quietly freaking out on
the inside! I wasn't really trying to show my feelings at that moment but I'm
sure it was obvious from my face and body language. Finally, Michael asked me
if we should just go up and try to find his apartment to see what the hell was
taking them so long, as he was saying that I was already making my way up the
stairs!

Michael
followed quickly behind me and we made our way to the third floor. It was
obvious that it was going to be difficult to find where they were at since there
were maybe four to five doors on each side of the corridor, and nothing about
any of them indicated that it was Ruben's apartment. I don't know why but we
were hoping that one of the doors would have had like a rainbow or something
gay on it so we could quickly identify that it was his! But that wasn't the
case of course, so we knew we had to start knocking on doors to see where they
were. I knocked on the first door on the left and some woman answered after a
few moments, I figured it wasn't Ruben's apartment but I still asked if he
lived there and she said I had the wrong apartment. So Michael ran off to the
door on the right side of the building and knocked, and another woman answered
almost immediately, and he asked her if Ruben was there, to which she said that
she actually knew him and that he lived two doors down from her on the right.
We were so thrilled at that moment and we both thanked her and ran off down the
corridor to Ruben's apartment!

We
got there in just a few seconds and Michael knocked on the door and we waited,
but no one was answering. Michael knocked again and we waited, looking over at
each other, then we started to wonder if maybe there was another Ruben on the
floor and the woman got them confused, no one was answering the door! Being far
too nervous and anxious, I just reached out and grabbed the door knob and
twisted it, it was unlocked, so I opened the door ever so slightly and we both
peaked inside, making sure that no one we didn't know was in there. We didn't
see anyone, so I stuck my head in even more, and the sounds... the sounds I
heard, the sounds that quickly directed my attention to the right, down a
hallway, where I saw light beaming from a room, light that was ever so softly
brightening up the apartment itself... sounds of people groaning, moaning,
slapping sounds... I looked over and saw through the opening of that door was Ian,
he was slightly bent over a sink with both hands gripping it on each side,
wearing his shirt, but his jeans and underwear were down around his ankles, and
there was Ruben, behind Ian, bent over Ian holding him around his waist with
his left arm ever so tightly, with only his shirt on and his jeans and
underwear also around his ankles, he was pressing his chest and stomach right
on Ian's back, and his right hand, holding Ian's face and neck as it was turned
to the right, facing away from the opening in the door, as Ruben was hurriedly
kissing him and sticking his tongue down Ian's throat. Ruben was grinding Ian's
ass so hard with the occasional pulling out and slamming back in, that's where
the slapping sounds came from. I was watching all of this happen, but realize
that this was merely only a few seconds of what I saw. Michael came out front
behind me and saw what was going on, and let's just say, he flipped the fuck
out! He was screaming "OH MY GOD!" and "ARE YOU SERIOUS?!" and "WHAT THE
FUCK?!" He just kept repeating those phrases, pacing all around, while I just stood
there stunned, I couldn't say anything or do anything. Ruben and Ian were
caught so off guard by us being there so Ruben quickly shut the bathroom door
pretty hard and all you could hear from inside there was "OH SHIT OH SHIT" and
"OH MY GOD" and just a lot of gasps. I could hear them fumbling around trying
to put their jeans back on and saying stuff to each other but I'm not entirely
too sure what. I then sort of snapped out of it and walked over to Michael and
grabbed him by his hand and then by his shoulders and led him out of the
apartment back down to the car.

I
got Michael's keys and opened the passenger door and sat him inside, and I
walked around and got into the driver's seat. We just sat there. I sat staring
straight ahead while Michael began to cry his eyes out next to me. I mean he
was really sobbing. There was a lot of "how could he do this??" and a lot of "I
came all the way for that fucker and he does this to me!" phrases being thrown
around. I still couldn't say anything. I knew that I was sad, maybe a little
heartbroken even. I was trying to convince myself that I knew what kind of boy
Ian was, and that I shouldn't be sad or mad about what just happened, but I
was. A couple minutes later I saw Ian running down the stairs as fast as he
could, I guess he thought we were going to leave him, and he came up to the
car, looked through the windshield and saw where I was sitting, and he came up
to the driver's side window. I got out of the car and told Michael just to stay
in there. I walked to the back of the car with Ian and just stood there with a
blank look my face. He told me how he knew what he did was wrong and that he
really didn't intend to do what he did with the guy. Ian said that when he went
up to use the bathroom, as soon as they got into the apartment, Ruben shut the
door and simultaneously grabbed Ian's hand and pulled him in towards his chest
and wrapped his arms around him. Ian reacted by saying "oh... oh my god what
are..." Ruben cut him off by saying "what's up...?" with a devious grin on his
face. Ian said he was so confused about what was happening and that his heart
was beating so fast. He then told me Ruben started to grab on his ass, massaging
it over his jeans, saying that he had been checking it out earlier and loved
what he saw. Ruben even said that he wished that Ian was coming to meet him
instead of Michael! Ian then said he began to get really horny from Ruben
grabbing and massaging his ass, and also from being so pressed up against him, that
he started to moan in his little sexual way. Ruben took it as a sign, so he
moved in and kissed him pretty roughly. Ruben then dragged Ian off to the
bathroom and actually let him pee while he stood there watching, and that was
when it all started to go down. Ruben yanked Ian's jeans and underwear down and
got on his knees and started to shove his face right into Ian's butthole while he
was slightly bent over the sink. He said he knew he had to stop him but it felt
just too good. And so from then on Ruben got up on his feet and began stabbing Ian's
hole with his dick until it was able to go in without lube and just fucked him,
and minutes later that's when Michael and I walked in. Ian added that they both
actually heard us knocking, but Ruben was so intent on using his ass and
cumming, that he wasn't remotely worried about whoever was at the door. This is
something I know far too many guys will understand. Sometimes it's just too hard
to stop once you're in it.

Ian
looked so obviously flustered and really nervous, that I pulled him in close to
me and just hugged him. I rested my chin atop his head and he hugged me back.
But now I had quite the dilemma on my hands. We used Michael's car to drive
there, Ian was my friend/lover, Ian's now presumably on Michael's bad side, and
we all were three and a half hours from home. I really didn't know what else to
do or say, so I walked back to the car and told Michael that we should just go
home and that I would drive like we planned. He didn't say anything. I asked if
he was "good" and still he didn't reply. Then I told him that Ian was going to
get into the backseat, but surprisingly he still didn't say anything. So I told
Ian to get inside and so he did, ever so slowly, and we just drove on back home
at about 5:30pm. The whole ride there nobody said anything, just the music playing
softly in the background. The sky began to get dark with still the hint of sunlight
coming through. It was about two hours into the trip and I was driving like
usual, when out of nowhere Ian leaned up in between the seats and gave me a big
kiss right on my cheek, then he leaned back onto his seat again. I'm still not
sure to this day whether that was a kiss just to be a kiss, or if it meant that
he was genuinely sorry for what he did, or if it was his way of suggesting that
he thought of me as more than just some guy who fucked him. I don't know, but either
way it was really sweet. The road trip actually took an exciting turn with us
being chased down by the state police because I was speeding. It wasn't my car
and I didn't want to get involved with the police so I ran from the cop which
was so stupid. I swerved in and out of traffic like I was some stunt driver and
took the first exit that came up and stopped at a gas station that was full of
people, figuring that we would be able to hide out there until the coast was
clear. It really did make for quite the ride for Michael and Ian as they began
to speak, not directly to each other, but about the exciting incident that took
place while in the presence of each other, if that makes any sense. We bought
some sodas from the gas station, put some gas since we were running low, and
headed out after about 20 minutes.

We
finally made it back and so I dropped off Ian at the end of his street at about
9:30pm. I told him that I would come back to pick him up as soon as I got home.
I instructed Ian to tell his dad that he needed to come back home to shower and
change clothes but that he would be heading back out to the "birthday party." Ian
said "oh... okay" and walked off home. I quickly realized then that I never actually
told Ian about hanging out after the trip, I just figured it, but Ian didn't
say no or anything so it was a go. On the ride to my house Michael and I talked
about what happened as he was still angry about it all. I just told him that at
least now he knew not to waste his time on these out of town guys. I then told
him I was so sorry about Ian and that I wouldn't bring him around ever again.
So I finally made it home at about 10pm, Michael switched seats with me and drove
on home. Instead of getting into my car to leave, I went inside and took a
shower and changed since I wanted to be fresh for Ian, so I took a bit longer
than I should have. A while later when I was finally ready, I left to go pick
up Ian.