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TMI Thursday: In the Out Door

September 15, 2011

It is with a heavy heart that I share this story of misdeeds I've done with my dick. No,'s okay.  I'll make it through.  I just have to be strong.  Like bull.

Yesterday, my friend Nick became dead to me advanced his career, taking a different position with a different company. Since I'm a jealous asshole, I shall miss his presence here within the hallowed halls of my main job, though I am happy for him.  As Nick is a regular reader to this blog--as regular as you can get for something that never updates--I thought I would finally piece together the story that I promised back in the dog days of summer. It's called that because I was as hot as dog balls on thigh humping night.

I'm not sure what that means, either.

Anyway, this one is for Nick, who not only is far smarter than I, but is also far better looking. Not to mention he's been banned from nude beaches because the other bathers are terrified of the beached sea serpent that unfurls itself when Nick lays out on his towel. I'm not saying he's massive or anything, but he's better hung than the jury for Phil Spector's trial.

Enough about Nick's anaconda (as a note, it don't want none unless you got buns, hon!); we're here to read embarrassing stories about what I've done with my pecker. And it certainly is interested, even if you don't got buns. Hon.

When it comes to sexual encounters, I've certainly had a few. Unless, for some reason you're my mother reading this. In which case, please, continue lying to yourself and believe that I've only had two. Ever. And none of them were upstairs in my old bedroom. *shifty-eyed*

While my encounters are many, it seems that the greater number of sexual foibles and/or follies took place with She-Who-Cannot-Be-Named, otherwise known as Sheila the Buxom The Ex.

If you haven't met The Ex before, feel free to peruse old TMI Thursday posts, as she and her lovely breasts and perfect ass show up there quite often. I feel that, if I compliment her, even these many years after the fact, it will soften the blow should she someday discover several of her sexual misdeeds have been recorded in electronic media. Because it's not like that shit's forever or anything. Oh, internet, what would we do without you? THANK YOU, AL GORE!

Anyway, let's cut to the chase. One night after working at the old bookstore, I went over to the Ex-Fiancee's house. Instead of watching a movie or going out to eat, we decided to probe each other's bodies with parts of our own. This happened on a fairly regular basis. You'd think that, with all the food I wasn't eating, I would have been thinner. Hmm. Go fig.

We were back in her bedroom and I had just worked her out of her clothing and, admittedly, I was had removed my own garments. We were making out pretty hard, hands and lips were moving over every part of each other's bodies. I cupped her breasts, ran my hands down her sides and slipped my fingers between her thighs and into her. Once I felt she was ready, I kissed my way down to her nipples and trailed my lips and tongue down her body as I slipped off the bed. I nestled between her thighs and went to town. After thoroughly enjoying a bout of oral, I decided that I'd try to last as long as possible and just enter her while she was moist and ready.

As a taller man, one of my favorite ways to do the deed is to be standing at the edge of the bed, clasping her thighs, and thrusting into her while her ass is essentially hanging off the edge of the mattress. As I had just finished cunning her lingus, not only was she basking in a post-orgasmic bliss, but she was wet and lubricated and ready. I stood, pulled her willing thighs apart and entered her. Her green eyes flared open as she gasped, she started moaning, and I was off.

Being a gentleman, I started slow, letting her natural juices envelope and lubricate me (this is an important point, so pay attention; re-read that shit if you have to), but as time passed and I things became slicker with her body's essence, I began to lose myself.

It's also important to note that the Barenaked Ladies song, "One Week", had been pretty popular around this time. If you're unfamiliar with the song shame on you!, it features the lyric "Like Sting I'm tantric!" It's a reference to a rumor that Sting is all about the tantric sex and can go on for something like four or five hours worth of sex. It's not so much that he's tantric; it's just that he's motherfucking Sting!

Anyway, this got me to investigate what tantric sex was. With all that "last as long as I can and unearthly glow of awesome sex" reading in my mind, I decided that this night, the night I was with my fiancee, I was going to try the tantric moves. So there I was trying the shallow, shallow, deep shit. And things were going well. This might be skewed slightly because I was having sex, which means that, in my mind, things were probably going pretty well to begin with.

All that aside, I was trying the alternating shallow and deep thrusts. As I mentioned earlier, my fiancee was pretty wet from our foreplay, and by this point all of me--shallow or deep, doesn't matter--was pretty well-lubricated. So I tried the shallow, shallow, shallow, shallow...thing when my mind was like "Put it in her! Hard! Motherfucker!"

Which is what I did. I was doing the shallow thing, not much of my penis was actually in her, so when I pulled back for a deep, hard thrust, I kind of slipped out of her. This did not deter me when I went for the deep thrust.


I was in her.

Guaranteed to satisfy
Except...I wasn't in her. When I went for the deep thrust after all the shallow bullshit, I kind of forgot to aim. The next thing I knew...I was in her ass, buried up to the hilt. I knew this because those green eyes that had gotten wider when I entered her now goggled out of her head in a fashion that can only be described as "cartoonish". Her body also started contorting and shuddering in a not good, not so sexy way.

Oh, and she screamed.  Loudly.

Unsure of what was going on, I looked down as she was rolling onto her side and feeling around her ass with her fingers to see if she was bleeding. Me, being the suave and debonair lover, did manage to ask if she was okay before I started giggling.

"Well, I'm okay. It's not that I'm opposed to's just...that was the first time...and I kind of wasn't ready for it."

And my loving and caring response?

"I understand. It sure did feel tight. But I understand."

I'm such a prize.

After I washed myself up, we resumed with normal, vaginal sex. However, the butt-cherry had been popped and it was only a few weeks until curiosity got the better of both of us and we returned to the tacitly taboo sport of anal rompage.

How very apropos
But (heh) that's a story for another day.


Moooooog35 said...

Nothing gets a woman going like accidental anal.

This reminded me of this post I did about a friend who had a less than stellar encounter.

Women. Can't live with 'em. Can't ram 'em in the ass by surprise without getting shit for it.

Sometimes, literally.

MJenks said...

That's not the guy with the celery clinging to his dick after he pulled out, is it?

Anonymous said...

Sounds similar to a story of my own. Except she was drunk, we were going fine, she stopped me, and stuck it in her ass and had me keep going. Okay, whatever.

Also, I'm really glad you said "celery" because I was about to click Moog's link.

SkylersDad said...

I'm with Louis CK on this matter. You are a few millimeters away from the greatest spot on earth. Why go for the butt?

Jill VT said...

I wish I liked it as much as my husband, but OY it just hurts.

Unless I am super inebriated. Then bring it on!

MJenks said...

@ Joshua: Yeah, someone needs to stop getting their wife drunk on bloody marys...

@ SkyDad: Disneyland?

@ Jill VT: *sets bottle of wine on counter*
*nods and smiles*