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A Series of Letters to the First Girl I Ever Fingered

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Dear Emily,

Hi! How are you? I hope this letter finds you well. I don't know if you remember me or not, but I'm the guy who fingered you at sleepaway camp.

Anyway, I was just thinking about that, so I thought I would write and see how everything turned out with you.

Your Friend (kind of),

Michael Ian Black

Dear Emily,

After not getting a response, I have become very worried that my last letter somehow offended you. Confused, I reread what I wrote several times, and finally came to the conclusion that, if you were offended, it was probably the part about fingering you that did it.

If so, I am very sorry. Not about fingering you (which was great), but about referring to it so candidly after not communicating with you in over 20 years. So, I'm sorry. In the future, if I refer to fingering you at all, I will try to be a little more discreet.

Very Sorry,

Michael Ian Black

Dear Emily,

Hi, it's me again (the guy who f-ed you). Still haven't heard back from you. Is everything okay between us?

Write Back,

Michael Ian Black

P.S. That's a rhyme - "Write Back/Michael Ian Black" LOL!

Dear Emily,

Oh my God! I just realized that when I said I "f-ed you" in my last letter, that easily could be read as "fucked you." God forbid your husband or lover (lesbian?) should read that! If that person IS reading THIS letter, I did NOT fuck your wife/lover. I just fingered her. I was just trying to be discreet about referencing it, which is why I used the initial "f" for "fingering." Total brain fart!

Please tell Emily to write me back. Or Emily, if you are the one reading this, sorry about calling you a lesbian in the previous paragraph (unless you actually ARE a lesbian, in which case I am TOTALLY cool with that) Did my fingering you turn you gay? I hope not.

Sorry Again,

Michael Ian Black

Dear Emily,

Still no word from you. I feel like maybe we got off on the wrong foot right from the get-go, and I'd like to try to make it up to you.

Let me start over, and if you still don't want to write back, I will definitely understand.

(Starting over):

Dear Emily,

Hi! How are you? This is Michael Ian Black. We went to camp together a long time ago. In fact, we kind of "dated" one summer. Pretty funny, huh? I don't know if you remember me or not, but I definitely remember you. In fact, I have many fond memories of walking around the lake with you, playing knock hockey with you in the canteen, and also finger popping you.

The truth is, you were the first girl I ever fingered, and I still think about it all the time. Please take that as the compliment that it is intended to be, and not as anything "weird" or "creepy."

(Believe me, I could easily see how receiving a letter from a 35-year-old man reminiscing about fingering a 13-year-old girl could be construed as inappropriate. It was DEFINITELY not intended that way)

Anyway, if you get a moment, I'd love to hear all about your life. Do you like dogs?

Your Friend,

Michael Ian Black

Dear Emily,

It's starting to become clear to me that you have no intention of writing back. At first I thought it was because you were shy, and didn't know what to say in your letters, which is why I ended the last one with a question designed to begin a dialogue ("Do you like dogs?").

However, now I'm beginning to think you just don't want to communicate. Maybe you told your husband that HE was the first guy who ever fingered you, and these letters are a painful reminder of the lie you are living.

If that's the case, I DEFINITELY understand. I was once in similar position with a girl who wanted to put something (a small jar of martini olives) up my ass. Of course, I told her she was the first. But believe me when I tell you, she was FAR from the first.

I lost touch with that girl a long time ago, but if she were to write to me today, I think I would at least have the courtesy to write her back.

I hope you die.

Michael Ian Black

P.S. If you do die, I'm going to go to the funeral and finger your corpse.




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46 Comments

funny stuff lol

Posted on 7/14/2008 1:46:52 AM

Seems more and more men have sexual drive for interracial beauty like me @ ___UKinterracialmatch.c o m____, where many interracial women, interracial men and their admirers meet and seek fun&love together! hi guys, am I right?

Posted on 7/2/2008 7:31:37 PM

Seems more and more men are attracted by sexy big curvy beauties @ hot dating club ____PlusMeet.com___, where many big boob women, big booty women and big manful guys meet and seek fun&love together!

Posted on 6/18/2008 11:33:44 AM

Story of my life

Posted on 5/18/2008 9:38:13 PM

The Mayor

I'd appreciate it if everyone referred to Michael by his proper title of "Dr. Michael Ian Black."
Thank you

Posted on 3/26/2008 12:11:22 PM

Hilarious!Does ur finger still smell?

Posted on 3/22/2008 4:35:26 PM

Bob

That wasn't funny

Posted on 3/16/2008 6:39:28 PM

Atlas34

Hysterical

Posted on 3/12/2008 3:54:10 PM

dude

that sucked

Posted on 3/6/2008 6:08:46 PM

M.I.B, You awkward comedic genius bastard!

Posted on 3/4/2008 5:57:53 PM

brit

LMMFAO wow that was the best series of letters i ever read. i especially like the last one haha.

Posted on 1/25/2008 1:59:03 PM

Michael Ian Black ftw.

Posted on 1/23/2008 3:47:56 PM

Me!

This has inspired me to contact the first girl I ever boinked. And by boinked I mean made love to (did it).

Thank you Michael Ian Black

Posted on 1/17/2008 7:25:25 PM

SnuggleBunny

oh i love michael ian black especially when he does the Vh1 shows ^_^

Posted on 12/28/2007 10:06:55 AM

bridget

he is so funny! but kind of creepy.

Posted on 12/25/2007 10:51:17 AM

Anonymous

Failure.

Posted on 12/14/2007 1:12:17 AM

sunny

haha so funny

Posted on 12/6/2007 10:01:49 PM

unknown

lame

Posted on 12/6/2007 10:00:09 PM

unknown

haha maybe it is helpful to date a girl

Posted on 12/6/2007 9:58:35 PM

unknown

haha How funny

Posted on 12/6/2007 9:42:56 PM

More Sex


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