My Best Friend (Cuntboy/Dickgirl)(More tags inside)

Story by Darkflight

Alright, so a bit of a preamble here. I stopped writing for awhile, like over six years since I posted anything here, tho still been lurking and reading. This story has been bouncing around my head for a couple years at least, and has gone through some changes, to what it is now. Like ages, jobs, what they like to do, like at first, Casey was into playing baseball in high school, and Jack ran the family pizza parlor. The dynamic is a bit different for any kind of story, like stating some things up front, and the tense is unusual, like it's all from the future, but also told in real time. I hope people like it of course. And there's some more to tell, but it was getting so long so I'm gonna split it into two-three parts at least. I don't think it's gonna go on forever, but as you'll see, there's to the dance at least, and then getting them to where the 'movie' can end and there's only to say "and they lived happily ever after" It's also not 4th wall breaking exactally, but it is self aware and talks to the reader, but not in the usually 4th wall breaking sense, at least in my opinion.

Hope you enjoy

(Also, you can thank vacuran, his (her?) Ashley and Jake story got me to think of this and got me writing again)

So there I was, an elf ranger by the name of Elorrian, I was hunting down a group of mind flayers, squid guys with nasty mind powers, but I had a Rosee with me, a Halfling rogue and sorcerer, helping me out as we tried to stop them from gaining a foothold on the surface world. It had been just the two of us for a long time now. We had killed several of their mind slave servants so far, but then we walked right into a few of the Flayers themselves when we were a little less stealthy then we had hoped to be. Rosee blasted one with some magic, she got a critical hit and blew its head off, Woo Hoo! But then got herself mind blasted and fell down off the ledge and into darkness. I think I Forgot to mention we were a little underground. Not miles or anything, just a 100 feet or more probably. I shot one with an arrow right in the eye, but didn’t kill it which sucked, and got the other one in the heart, critical hit, so two dead, but then the last one got their turn and mind blasted me. Two out of three ain’t bad, but then I failed my saving throw and blacked out.

I woke up in a cell. No sign of Rosee, she prolly survived the fall and only took half damage if that. Hopefully she’d show up soon. I looked around saw all my equipment in a corner out of reach on a rickety old table. I had a rock for a pillow in my cell. It took me a minute to figure it out, but I did and threw the rock at a table leg, NAT 20, YES!!! The table then fell over towards me and my stuff rolled a few feet and was just in reach for me to hook it with the sleeping blanket which was also in my cell, and I pulled it all closer and started getting dressed.

Everything was there as far as I could tell, but when I got to my Belt of Giant Strength, the Mind Flayer must have switched it, it turned out to be a Belt of Masculinity/Femininity and I got turned into a female elf. Just then I heard some laughing as the surviving Mind Flayer came out of the shadows, who I somehow couldn’t see earlier, despite my heat vision, wearing an eyepatch, her robe open while she, yeah she, I could see her double D sized breasts, and she was stroking a thick 10 inch cock where, well, nothing should be, but no biggie I guess really, who doesn’t paly D&D without a ton of homebrew stuff?.

“Ah, Ellora should I say now, so nice to meet you, I think we’ll be having great fun together” she said with an evil grin, though I’m not sure how I was supposed to know she was grinning under her tentacles.

***

“Ah, man, Casey, now you’re just being gross,” I lied, it was kinda hot, though not so much the tentacles, not that it was more hot become of them, just not actually gross either. “I told you it’s not some new fetish, I got redirected when looking at some… other stuff” I said as I turned red.

“So you’re really not into dickgirls and tentacles?” Casey said as she mock pouted at me. She might even had been a little disappointed if I wasn’t imagining things.

***

Casey was my best and only friend really. Close friend that is, there were others at school we hung out with there and always said ‘hi’ too and ate lunch with. But she was the coolest person I knew, and I’m sure glad we stayed friends even in high school. She was still growing, like 5”8’ now. Would probably grow to 5”10’, dark green eyes, long blond hair in a ponytail and small size C breasts which would probably grow to a good D eventually. I really had a huge crush on her, but I’m sure she didn’t think of me the same way. Me? I’m Jack, we moved here to Littlevale in time for 5th grade, and now we were now seniors, both 17, almost 18, a small midwest town, just 30 minutes from the big city with the medical doctors I started needing to se

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