Date: Fri, 9 Sep 2016 02:47:15 +0200
From: Kevin Blake <bigblake27@gmx.com>
Subject: Greater toronto Area Adventures 4

Greater Toronto Area Adventures
By: brownlover
Bigblake27@gmx.com

The following is the events of how my cherry was popped lol. But seriously
this is to my best memory what happened. I know it may surprise you that a
guy that currently lives a predominantly straight life today would have
allowed a guy to fuck me but I was young at the time and curious and wanted
to experience more. To be honest I do enjoy bottoming but most of the tops
I've found to be mind blowing were generally one time hookups. Mainly
through their decision to not wanna meet again but hey cruising and hookups
isn't for the faint of heart if you are gonna catch feelings you are bound
to end up pining for some guy who will never feel the same way you do.

Chapter 4 - the cherry buster

This was back when I was 21 I would say six months after I met that first
Arab guy I told you guys about in chapter 1. I for whatever reason whether
it was years of curiosity or the need to try it once decided during a cold
January/February night that I was gonna get fucked. It wasn't long till I
found a willing guy on a website.

He was black, Jamaican actually we decided to video chat on MSN messenger
since neither if us wanted to send face pics. Wherever happened to msn and
yahoo messenger i guess Facebook and Skype took over. I digress. So he
chatted with me face to face at the time I was a bit pudgy around the waist
but otherwise a pretty slim guy. I think he fell in love with my face
because the moment he did he went into charm mode. You know leaning in
those angles and always making sure to smile this guy was trying to impress
me but little did he know I had already decided he would be the one he
could have been a jerk and I might still have spread my legs for him.

He was about 5'9 and 30 years old a solid muscular yet average build and
8.5 inches which I was to learn later was thick as fuck. I told him I was
thinking about bottoming truth was that I was super nervous and he wanted
to exchange numbers so we could talk and then meet. I explained how I
couldn't how my mom would hear me leave the apartment no way was I gonna
get up out in the cold either.

For some strange reason I sent him my number before I closed the
messenger. He didn't waste time and called right away.

"Hello," I said picking up my cell before the second ring being sure not to
speak too loudly and alert anyone.  "Sup , so you said you were never
fucked before?" He asked

"No" I responded "And so you looking to take it now hmm" my heart skipped a
beat he was so forward and the dirty talk was making me hot. Did I tell you
guys that's my weak point nothing gets me turned as much as hot dirty talk
any man or woman (and I haven't met much of either) who can master this can
make me cum without touching myself.

Back to the story I told him yea and then somehow agreed to meet him at the
end of my street. He drove from Jane and wilson to Malton and picked me
up. he was surprised that I was a taller think build guy which was strange
because I showed him my body on msn but he seemed eager though and we drove
off to his place.

He lived in a basement and we had to be quiet cause he had roommates the
first thing we did was turn the TV on to help cancel out any noise. We
stripped I started to get hard but he was fully hard and ready his dick
curved just a little to the left but looked ferocious.

I put my hand on it, it was thick to this day I have only met one guy who
was thicker but that's another story for another day. I was gonna go on my
knees and suck him off but he just wanted to get down to business. He put
in a condom and pressed me backward till I was on the bed on my back legs
up by his side ready to offer myself to this complete stranger . I think he
was kissing my neck a little to relax me. He really did have a hard
muscular body I was pretty soft then hardly worked out. He attached for
lotion at the bed side. Yup spit and lotion was the lubricant the night I
took this horse hung stud.

Now I tried things before like fingering myself but I never adventures into
anal toys. So I was as tight as any virgin was gonna be, I had also take
the time to clean my hole really well I didn't know about the whole
cleaning or giving oneself an enema with water at the time so there was the
potential for him to literally fuck the shit out of me.

Anyways I think he rubbed the lotion on my hole which felt good, then he
rubbed some on his dick. I braced myself although now I know the best thing
to do is relax and breather and push like you're taking a shit.

He put a pillow under my butt and put both his arms under my knees as he
held my legs up.  He pushed forward several times but still nothing this
went on for about 3 minutes or so, he just kept putting more lotion.

Finally I was getting second thoughts.

"Maybe I'm just too tight" I said nervously. I just wanted to get out of
there now he was incredibly large and no way was I gonna take that thing in
me.

He tried one more time pushing extremely hard when I felt my hole give way
and his head popped in. Just the head but in that moment I feel felt like
half of it hard been shoved right in.

He stopped for a sec and asked if I was ok I said yes.  He slowly eased
that thing in me and I know I should have felt amazing pain but the shock
around the nerves in my hole gave me more of a numb feeling and I felt
stuffed more than anything else. He did a back and forth motion for a
couple minutes and I though I was doing quite well.

I was giving out a few "ohs" but had to be quiet cause if the roommates.

He leaned over me and asked "you ready for the rest?"

Holy shit. What the fuck I thought I had taken him all. I said "yeah sure"
and he slid the other half in this time I could feel his pubic hair against
my ass. Fuck was he deep.

He really picked up the pace now and that numbness turned to a bit of
paid. I tried giving out a few groans and and "uhs" but he keeps saying
"shhhh shhhh shhhh". How could I be quiet when he was driving that thing
into me like a bull.

"Oh yeah give it to me" I said. Not because I wanted it but because I
thought that was what I was suppose to say. In truth I felt like I as
getting rapped like I want ready for it. But I was getting fucked anyways.

My tight hole must have been taking effect because he was heaving like a
sprint runner and sure enough fell onto of me full weight as he came into
the condom. I kinda liked this moment his weight actually felt comfortable
on top of me and I ran my hand over his back and was pretty glad it was
over.

He pulled out and I saw a bit of blood on the condom not much but enough to
know he had opened me up a bit. We got dressed quick and soon we were out
the door.

On the car ride home I was pretty quiet.

"So the sex was good?" He asked

Had he forgotten I had never been fucked before? What was I to compare it
to?

"Yeah" I said.

He dropped me off where he picked me up.

My hole was throbbing since he was done with me and it felt tender as I
laid in bed and tried to sleep. In the morning it had ballooned like a
hemoroid I felt extreme pain and it was hard to walk for the next three
days I had to put effort into making walking look effortless for fear
someone would know I was fucked.

But I survived and my hole didn't get back to normal for at least a week. I
got fucked a few times after that but never took to bottoming besides most
guys preferred for me to be the top anyways.

I never saw him again despite what the experience was like I did try to get
with him again. He replied to a few messages but dropped me like an old
rag. I felt used but that's the way it goes.

Anyways the experience made me who I am for better or for worse.