Date: Sun, 12 Nov 2006 11:17:51 +0100
From: Expat Stud <expatstud@gmail.com>
Subject: Kathy's Boyfriend II

My best friend Kathy's boyfriend Simon had just shot a
huge load in my mouth and I had shot my own load all over
my chest. Simon had fed that to me as well, scooping it
up and rubbing it along his cock, then sliding it into my
mouth. His cock did not deflate slowly, and I was over
the top in the scene of it all. Simon was a hot guy,
really masculine and just oozed sex appeal. He had a
great cock-long enough to make sucking on it a challenge,
and REALLY fat. There was no way that I would be able to
drive him back home-the roads were getting bad from the
snow, and my little Tercel would not have managed it. And
besides, the night was still young and I had a horned-up
man in my room.

As I had mentioned before, Simon was really interested in
exploring my ass with his hog of a cock. It was not the
type of cock that became more narrow as it got to the
shaft; rather, it started out fat and just continued that
way up to his bloated head, which was long with a slight
mushroom to it.-it had an acorn look to it And it wasn't
perfectly round-it was more flattened along the top and
the bottom (cannot think of the right word for it.) It
wasn't particularly veiny, I recall, and he had plenty of
skin to spare. I didn't know how I would accommodate it-I
had been fucked many times before this by a professor of
mine in university whose dick was longer, but his cock
was not nearly as wide as this one.

We went into the kitchen to get something to drink, with
Simon not able to keep his hands off of me-rubbing my
ass, my chest, kissing me. He kept saying how he had
wanted this for a long time, that he had wanted to play
around with me but he had never found the right moment,
how he wanted to take me to a club called The Dock down
on the waterfront and show me off to people. How much of
this was the weed and alcohol talking I will never know,
but my body responded in kind to all of the flattery
(hey, we all have egos.) He sure was a sweet talker,
because in no time I was horned up again, eager for some
more play. Simon of course was as hard as ever (did his
cock ever really go down???) and he kept rubbing his cock
on mine, rubbing it against my thighs, sticking it under
my balls and slowly gliding back and forth. He was
leaking everywhere, and we were both getting really
turned on. He was a kisser, and his tongue kept exploring
my mouth. What can I say, it was hot.

He asked how long I had had the hots for him. In
hindsight I think it was a bit of an arrogant question to
be asking me-he's the one who initiated all of this,
after all-but then Simon always had an arrogant attitude.
I mean, he was a gorgeous man with a nice piece of meat
hanging between his legs (not hanging anymore, but still
pumping between my thighs.) I told him that I had not
necessarily thought of him in that way-he was Kathy's
boyfriend after all, and she was my friend. He laughed,
grabbing his cock and gently tapping it against mine,
saying that everyone wanted a bit of what he had and that
he was okay with it-he was an equal-opportunity lover,
that he was just doing his bit for the betterment of
society. Cocky, yes, but the guy did have a point.

'I really want to fuck that ass of yours, I could do a
lot with something like that to play with.' Simon placed
my hand on his cock and then started kneading my ass
cheeks. He put his mouth to my neck, kissing softly, then
put his lips to my ear and mumbled, 'I promise you won't forget it.'

I was hesitant, though. His cock was really wide and
thick, and it would have been like riding one of those
freakish dildos you see in sex shops. How that thing
would feel good I had no idea, but I wondered if I would
ever have the opportunity again. I hate to live my life
with regrets, and I wondered if I would have regretted
not giving it a try.

I suggested we go back to the bedroom and just see where
things went, that I needed to think about it some more.
We got into my bed and he asked me to suck on his cock a
bit while I thought it over, that he was really horny and
needed to feel my mouth do what it was obviously born to
do (and now it is my chance to be arrogant-I've always
been told that I give great head!) He sat up on my chest
and let me lap at his leaky knob-he was like a leaky
faucet (a tired cliche, I know, but I do not know how
else to describe it.) Soon he was feeding me his pipe,
telling me how great I was, how glad he was that I was
hot for his cock, that we obviously needed to become
better friends, that he seriously liked me. It was just
this steady stream of dialogue coming out of him, and it
really encouraged me-I was greedily sucking away as he
pumped my mouth, grabbing his cheeks trying to get him to
fuck my face faster, but he just kept up a nice slow
rhythm, telling me not to worry, that he had plenty of
jizz stored up, that I would get it soon, and for all he
was concerned I could have as much of it as I wanted
moving forward.

To my surprise Simon switched around and we were now in a
69 position. He pulled his cock out of my mouth and told
me to eat his ass, to really rim him good. I love rimming
guys, so I happily obliged. And to my delight I suddenly
felt Simon take my dick into his mouth. Damn, but it felt
good-I love getting blown, and he was pretty good at
it-obviously not his first time. He would go down to the
root, then slowly pull back up, all the while varying the
suction. His saliva was dripping down onto my balls, and
it felt like I was just bathed in lube down there. I was
in heaven. A gorgeous ass in my face, balls rubbing
against my chin, a fat leaky cock tapping steadily just
below my neck-what was there not to like?

With Simon's spit lathering up my balls, it inevitably
made its way down towards my ass (probably his intention
all along.) Soon one of his big fingers began to rub
around, gently applying pressure to my hole. In no time
it made its way through and he slowly started to pump it
in and out of my chute-not all the way, I don't think,
but just up to maybe his second knuckle-all the while
keeping rhythm to his sucking. Soon he had worked his
finger up all the way and he gently massaged it back and
forth. His fingers weren't terribly long, I don't think,
but they were long enough to find my prostate. Damn, but
he knew what he was doing! He kept it up for a bit,
poking at my prostate, until I got incredibly close to
cumming-he must have recognized the signs, as he gently
pulled his finger out, pulled off of my cock, and then
gripped my prick really hard-the same effect as a good
cock ring.

I kept lapping at his ass, moaning, writhing on the bed.
He would back up on occasion and tell me to lick his big
nuts for him, occasionally lifting up to stick his cock
in my mouth, telling me to 'suck my fat dick.' I happily
obliged.

Simon lifted himself off of me, telling me he wanted to
eat my ass before fucking me (a bit presumptuous, I
thought, but we both knew that this was going to happen.)
He moved down the bed and pulled me forward until my ass
was hanging off the edge, then he lifted me up, bending
me over so that my rear was completely exposed and in
position for him. My god, he was ravenous-he licked and
slurped and lapped and poked and prodded until I was
delirious, tingling all over. I couldn't help myself, I
just had to jack my cock. I was moaning away, letting him
know that I loved what he was doing. I was totally lubed
up, my hole opening and closing, opening and closing for
him. I was at his mercy at this point.

'Simon, will you fuck me?' I had crossed that line again.

'Tell me what you want, buddy, tell me what you want me
to do and where you want it.*

'I want you to fuck me,' I pleaded as a finger speared
me.

'Where do you want me to fuck you?'  Simon was teasing me
at this point. God, he was good.

'Simon, if you don't stick your cock in my ass now I am
going to spray all over the place.' I was desperate at
this point-I was about to blow and Simon was making me
beg for it. He would alternate between fucking me with
his finger (and sometimes fingers) and rubbing his cock
on my hole. He seemed to like rubbing the underside of
his dick just against the opening that was gaping in and
out.

'Did Kath ever tell you how she wouldn't let me fuck her
in the ass because my cock was too fat for her?' He kept
rocking his cock against me, teasing me. 'You know I will
split you open, don't you?'

I didn't care at this point, I needed his log up my ass
so I could get off. I was so close as it was, I was ready
to cum, and his cock was what I required. I was pushing
myself back on his dick, hoping to suck it into me.

'My god, I had no idea you were such a slut for my fat
cock. I warned you, buddy.' And with that he hoisted my
legs up onto his shoulders and plunged his dick into me.

Dear lord, I thought I was ready for what greeted me.
With all of the fingering and rimming, with all of the
fucks I had received from my professor Dr. Paul, nothing
prepared me for what just popped into my ass. I honestly
felt like I had entered another world, one with
indescribable pain. Women talk about how much childbirth
hurts, and that men cannot relate. Well, I felt like I
had a baby arm shoved into my ass all at once and trust
me ladies, I think I was able to relate at that point.

Simon just shoved his cock all the way up my ass until he
couldn't shove any more. I couldn't help it-I started to
cum all over the place-all over my chest, my face, my
hair, the bed. My ass was on fire and spasming like
crazy, milking his cock as though it were a teat or
something. My body was heaving like mad. Simon just held
his cock in place, telling me that I really knew how to
welcome a cock like his into my ass, that it felt like my
ass was kissing him. He was the cock of the walk at this
moment, totally preening in his masculinity. I was the
one speared on his cock, and I just happened to cum the
moment he shoved his dick into me.

'Fuck man, you really get off on my cock in your ass,
don't you?' Boy, Simon was really getting off on my
unabashed display of his overwhelming sexuality-it just
oozed out of every pore of his body. He kept rocking me
back and forth so that I could not forget what was lodged
in my butt. At this point I was almost convulsing, my
body was shaking so much. The air felt cold, my skin felt
cold. I had shivers pulsing through my body.

I readily admit that once I cum I completely lose
interest in sex, at least for a brief spell, and this
time was no different. I really needed time to recover my
senses and deal with what I had just allowed to happen-my
best friend's boyfriend had his cock in my ass. I told
Simon that I needed a break, that I needed to recoup, but
he didn't see the situation the same as I did; he was
just getting started.

'I warned you, man. And you asked for it. It's time to
fuck.'

And with that Simon started to pull his cock out, slowly,
rocking me all the way, shaking me up and down so that my
swollen rectum could squeeze him from every angle. You
know how it feels when you put on a pair of jeans that
are too tight, how at first it seems like it fits but
that the longer you have them on it just feels
uncomfortable? That's exactly how it felt. Simon's dick
was not necessarily long, it was not the 10- or 11-incher
that you so often read about, but boy it was fat. And my
ass, at least at this point just after I came, was too
tight.

Simon started scooping up the jizz that was on my stomach
and chest and suddenly yanked his cock out of my ass.
Goddamn, it hurt-I almost felt like it made an audible
pop, although in hindsight I am sure it didn't. He rubbed
my cum on his dick for a second time that night and then
pushed his cock into my bum again in one single instant.
My god, it burned, but I did feel incredibly full.

'Man, you really like this cock, don't you? I always knew
you would.' At that Simon started pumping my ass, slowly,
giving me time to come down from my high and get
accustomed to what was in there. 'I'm going to give you a
fuck you will never forget.'

Simon's pace quickened, and I was slowly regaining my
senses (it's hard not to regain your senses when a dick
like that is in your bum!) He developed a pace that was
good for him, that would keep him on the edge, and he ran
with it.

'My fat cock is fucking your ass, you should thank me for
it. You've wanted this for a long time, haven't you?'

My god, he was calm throughout all of this, and a bit
cocky. Maybe the weed and beer was wearing off and he was
going back to his normal self.

'Tell me you like it, tell me how much you want me to
fuck you.' At this point I could not contradict him, his
cock did feel good in my ass, albeit a bit crowded in
there. It was stretching me in ways I had never been
stretched before, opening all new sensations. Your ass is
filled with nerves for a reason, and I am convinced that
being rubbed by a big fattie is one of those reasons. I
pushed back on his cock just a bit, to let him know I was
still in the game. I wasn't ready to roll over yet and
submit, though.

'You little slut, you like my cock, don't you?' I just
looked at him, starting to feel lust again, starting to
feel that magic. God, he was gorgeous. 'Yes it is then.
Remember, you asked for it.' And then all hell broke
loose. It's almost as though a switch just flipped, like
when you turn the food processor up, and he started to
plow my ass, plowing it hard. In and out,  in and out. I
had no choice but to accommodate his girth, really. With
all of my jizz and his leaking cock lubing the way, he
really did not have much resistance. The human body can
take a lot, and mine was taking more than it had ever
encountered.

Kath was right: this guy knew how to fuck. No wonder she
put up with him and his antics. He was able to make a gal
(and guy!) feel incredible, and he knew how to use his
cock to maximum effect. He pumped me as though he had a
mission, and then he pumped some more. He yanked my legs
from his shoulders, pushed them together and flung them
to the side-as though he needed me to be tighter (how
could that be? I was already stuffed to capacity here!)
He would yank his fat cock just to the edge of my hole
and then plunge back in, and then do the same again and
again and again. And then he would jab at me, all the
while moving me around to get maximum pleasure from my
ass.

'I need to lie down.' And Simon yanked out suddenly (he
seemed to know the effect of yanking his cock out of a
hole, because he sure liked to do it. It made a person
gasp.)  He tossed my legs down and splayed himself on the
bed, spreading his legs out. 'I want to see you ride me.
Show me how much you want my cock.'

I was totally turned on at this point and really wanted
his cock like crazy. It was heaving there in the middle
of my bed, pulsing back and forth, driving me crazy.
'Suck me' was what I heard from Simon, and I went mad on
his cock, slurping and licking, longdicking as much as I
could. I had to have it back in my ass, so I climbed atop
him..

Simon pulled his dick down, denying me access.

'Tell me how much you want my cock in your ass.' For some
reason Simon really needed a lot of reassurance, but at
this point I was desperate to be as persuasive as
possible.

'Simon, I need you to fuck me hard.' I relented. I was
now begging for him to fuck me. I would deal with the
guilt in the morning.

Simon released his cock and told me to act like it was
the last cock I would ever ride, and I took him
literally. I bobbed up and down every which way for as
long as I could stand, and my own cock was like a hot
swollen iron-it was just incredible. I rode up and down
him the way any young, unjaded cock fucker would do. He
slammed in to meet my thrusts, all the while voicing how
great his cock felt in me, how I really knew to treat a
cock like his, how he always knew I wanted his cock.
Simon loved his cock, obviously, and loved the power it
had over other people. I happily went along with it-I was
near delirious.

I begged Simon to fuck me hard, to fuck me harder than he
had ever fucked before, to make certain I remembered his
cock, to sear it into my brain forever. And boy did he
deliver. He lifted me up and down on his cock repeatedly,
spearing me from as many angles as possible. I was going
crazy with heat-how lucky had I become?

'I'm going to cream in your ass, you fucker.' It was
difficult to hear Simon from all of the grunting and
panting going on. 'Do you want me to cum in your ass?'

Of course I wanted him to shoot in me-I was young,
caution thrown to the wind. I told him what I wanted,
that I wanted to feel him shoot in me, that I needed a
piece of him. He pushed me down onto my back, lifting my
legs up in the air, and started plowing away. He started
screaming at how horny he was, at how much I loved his
cock, at how he needed to cum.

'Tell me you want me to cum in your ass, man. Tell me!'

And I did, I told him that I wanted him to cum inside me,
that I needed him to cum inside, that I had wanted him to
cum in me for a long time. And then he unleashed. He
fucked my insanely, moaning, at times almost shrieking
(the neighbors must have heard it all, there's no way
they did not.) And he started to shoot. He trembled a
lot, he shook, his cock kept swelling in my ass. I have
no idea how much he shot, but it was a lot. And he kept
fucking away. As I said, his cock did not deflate
quickly-he had this amazing stamina that you don't
experience often.

I couldn't help myself-I was spewing all over (oh, to be
young again!) The room had that sharp, pungent smell of
raw sex--not a bad smell, one that I find quite pleasant.
Cum was flowing all over and once again I was beside
myself. What a night.

Simon slowly pulled out, making lots of noises-what a
vocal man he was! He gently lowered my legs and climbed
above my cum-covered body. 'Here you go-there's more
there, you just have to get it out.' And he pushed his
more-than-half-hard cock into my mouth and slowly pumped
away. I could tell when he would squeeze, as I got a
little dollop of leftover cock juice.

He finally pulled out of my mouth, slapping his cock and
remnant junk across my own chest. We were both in bliss.
Simon smiled down at me and collapsed by my side,
exhausted. He caressed my chest, telling me how much he
really liked me, that he hoped I could see through his
posturing and see how sincere he was.

The sex did not end there-he fucked me hard again that
nite before we crashed from lack of energy, and then we
repeated it for a good 45 minutes in the morning with a
nice slow fuck. My ass was tired and his balls had
finally run out of cream. The roads had been plowed and
salted, and I jacked his cock as I drove him back to his
parent's house. He told me how we were meant to hook up,
that it was the best sex he ever had, and that hopefully
we could continue exploring.

Kathy's street had not been cleared that day and she
could not make it into the shop, so I worked a bit late
until we could get another person to cover. Simon kept
calling me, and I never could talk to him. I was either
too busy or torn over my friendship with Kath. At one
point I looked up from the counter, and there he was,
smiling at me. I was a bit annoyed-I totally get into my
work, even today in the corporate world (yes, I finally
found a job that could use my degrees), and I wanted to
keep play separate from work. And that's when I uttered
the words I regret to this day.

'Simon, I like you and all, but don't get obsessed with
me, okay?' And that is the last I ever saw of him. I'll
never forget the look on his face when I said that-he
looked so sad, almost teary eyed.

I've often wondered whatever happened to Simon-we would
have been a good team-we both fed off of the other's
personality. I've tried finding him over the years (even
tonite I've tried to Google him, to no avail.) Kath got
pregnant with yet another man's baby, and she never knew
whose it was-maybe this produce guy, that UPS guy. I was
disgusted with her antics. Simon was cocky, but he was a
good guy, And I let him slip through my fingers.

Christine Lavin has a song entitled 'The Kind of Love You
Never Recover From'. It's about a woman who is happily
married, but she occasionally wonders about what life
would have been like had she married that other guy
instead. I'm happily partnered right now-11 years,
actually-but I occasionally wonder what life would have
been like with Simon.

Simon, in the off chance that you would read this, know
that I still think of that night. You know who you are,
so ping me at expatstud@gmail.com.