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Didn't See It Coming  

TrucknLuvn 59M/41F  
678 posts
4/24/2016 1:28 am

Last Read:
7/20/2020 3:47 am

Didn't See It Coming


"So there I was..."

Why is it all of the best stories start that way?!

And that is where I am heading with this particular blog entry. New beginnings, a first time, making a first impression... You know, that terrifying list of firsts that we all go through over and over again in our lives.

You always hear the stories of those firsts that end up being perfect. But what about the other times? We never hear the stories of a first that was off to a good start, but ended up being disappointing, disastrous, or dare I say, straight up embarassing.

And that is precisely what I am about to do! Here are two of my own personal tales of when a good start goes completely awry by the end of the night. 

--------------------------------------------------------------

Story 1

This took place about seven years ago...

So there I was, hanging out with a decent sized group of people. Some were my friends, others were friends of friends, and there a few that I didn't really know. We were partying and having a good time, typical for a Friday night at the club.

At the time, I was interested in this guy, Wes, and he happened to be there that night. He and I were dancing, flirting, and just having a great time together. As the night carried on, Wes and I continued our flirtation. We were both too drunk to drive, so a friend of mine, Kim, offered to let us crash there.

Kim took Wes and I back to her place and showed us to her guest room. As soon as she left the two of us alone, we were all over each other. It was getting hot and heavy and it was time to go for it!

I unzipped his pants, hoping for a nice big surprise...

Instead, I was surprised with the smallest erect penis I have ever seen.

Considering that my brain to mouth filter is nearly nonexistent when I am sober, it was completely gone that night. I started giggling and before I knew it, the most horrifyingly hilarious thing popped out of my mouth...

"Aww! It's cute! It's like a penis, only smaller!"

Needless to say, Wes was not exactly thrilled and he voluntarily spent the night on Kim's couch. I never saw him again. Whoops!

Honestly, I didn't miss out on much. Trust me, I saw it... I think?

-------------------------------------------------------------

Story 2

This was about ten years ago...

So, there I was, camping out with about thirty of my closest acquaintances. We had a few kegs of beer and tequila shots were being handed out like water. Everyone was nice and intoxicated. Good times.

It was a pleasant summer evening and we had a good camp fire going, so most of us decided to ditch our clothes. I was hanging out with this guy named Tony and things were... Well, they were looking up.

Tony and I excused ourselves back to his tent. We were taking our time, a kiss here, a lick there, a nibble here and there. After getting thoroughly turned on, I was ready for him! I needed to be fucked hard, right then and there!

Unfortunately, Tony slid it in, gave me about two and a half thrusts, and boom! He finished. Just like that. And he didn't even offer to help me get there. He just rolled over and passed out.

Gee thanks, Tony the twenty second wonder. You sure know how to please a lady! Jerk.

-------------------------------------------------------------

There ya have it! My two absolute worst sexual encounters. Both took place with good looking guys that I enjoyed spending time with. Everything seemed like it would be great!

But there was nothing but disappointment. Well, for me anyway.

♡Jess: The Trucker Babe

♡♡♡

Want more? Be sure to check out my blog: TrucknLuvn!


moonfish 56M  
466 posts
4/24/2016 2:19 am

Made me smile. But the same holds true for women. Some of the most gorgeous women I ever slept with were wet blankets in bed.


TrucknLuvn replies on 4/24/2016 2:29 am:
I fully understand where you're coming from! I'm openly bi and have had a couple of those myself. It happens!

SingleItalianGy2 52M
1205 posts
4/24/2016 1:45 am

OMG...You might have been one of my friends from some of the details in these story's. I have a friends that has teenie weenie syndrome....its a horrible disease. Sucks to be him......

Thanks for sharing


TrucknLuvn replies on 4/24/2016 1:54 am:
If Wes the Weenie Whistle would have explained his situation beforehand, I most likely would have kept my comments and giggles to myself.

Who am I kidding? I would giggle for certain. It was a nice thought though.

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