Soundtrack: Boten Anna by Basshunter.
Whisky and I decided to have a big ol’ party to celebrate our engagement. We invited a whole bunch of different people (sans family,) from his work colleagues to people I hadn’t spoken to in months. One of the latter was The Prison Warden (no number just yet.) I’d met him through work and helped him out with my couch a few times after he divorced his wife. He was a funny character, and not someone that I found attractive in the slightest. Well and truly friendzoned. No more, no less.
Flirtier
We all got drunk at the party, of course, and The Prison Warden got flirtier the more he drank. That was no great surprise… but the fact that he was flirting with both me and my husband-to-be was quite interesting. Well, to me at least.
Still, we were all slutty idiots when we were drunk back then. Prison Warden was acting no differently to me (and a few others) once we’d had a few, you know? I just assumed that he was bisexual and chuckled to myself at the thought of him trying to hit on Whisky… who was not bisexual in the slightest. We had talked about it in great detail one night in bed.
Nothing really happened until the party was coming to an end and people started to either crash out or go home. Whisky slinked off to our bed as I pottered about and cleaned up some empty bottles and cans, and it looked like The Prison Warden had fallen asleep on the couch. Once I was satisfied with my minimal cleaning efforts, I took myself off to bed right next to my husband-to-be. I loved saying that.
An Almost Successful Threesome
Whisky and I had been in bed and had already dozed off when someone opened the bedroom door. It sent a beam of hallway light directly onto my face, waking me up.
“Hey… hey,” they said. It was The Prison Warden.
“What?” I whispered, trying not to wake Whisky up, too.
“Can I come in?”
“No, go to sleep. Goodnight.” I sighed. Tiredly.
I’d drifted off again when he woke me up again. Whisky was already awake and chit-chatting to The Prison Warden, who was now sitting on the edge of my bed… wearing just knee-high white socks and a pair of black boxer shorts. That didn’t bother Whisky much, what with him being a soldier and all. Those fuckers are always getting naked for some reason. It did bother me, though.
Somewhere along the way, a threesome was brought up. I don’t know how these things keep happening to me, but maybe sluttiness attracts slut, you know? It started as a joke, then moved on to rules, and the next thing I knew, Whisky and I were scooting over so that The Prison Warden could get into my bed.
Oh, to be a drunken fool again, eh?
I found myself in the middle of the two men. Whisky’s fingers drifted down to my clit as mine reached for his dick, and The Prison Warden (TPW from now on,) rolled on a condom. After that, I’m not really sure what happened. There was so dry humping from behind, and some playing from the front… but, well, I can’t perform for an audience like that, it seemed. Plus, I wasn’t actually sexually attracted to TPW. It was kind hard for me to get it up for him, so to speak.
TPW penetrated me for approximately two and a half minutes, then came. Whisky took a few minutes longer than that, and I faked my orgasm not long after. We shared a smoke together, then we all went to sleep – Whisky and I in my bed and TPW on the couch.
It had been a very short-lived experience, really. All of my threesome attempts up until that point (and beyond) had been utter disasters. I mean, at least there was jizz in this one, I suppose… but was it really too much to ask for, to just have one successful threesome?! How many failed threesomes can one person have?
Actually, you know what? Maybe this is a sign…?
*ignores it*
Sadly, friends, there would still be more failed threesomes to come.
Sigh. Girl, give it up now. You’re not good at it.
Oh, little side note: I went back and fucked The Prison Warden during a very short-lived breakup, a few years later. That wasn’t much of an experience to boast about, either.
The next blog post in the dating timeline is this one: The Canterbury Tales.
Thank you so much for reading my blog today! 🖤
Would you like to read all about The Ex-Husband’s story, right from the very beginning? You’ll find that right here.
You can also read all about my disastrous dating history, right from the beginning, right here: Table of Dating Contents.
Alternatively, why not have a little peek around here: