This Hurts // 0:23 – 0:38

Let me start off by saying, there’s been no real system or list of boxes to check with who we go out on dates with. If they trip my trigger enough to want to fuck them, for whatever reason AND they can stay within the boundaries we set, it’s all but certain I will be scratching graffiti into their back eventually. And with that loose, literal “Fuck the World” attitude we found Good Christian Boy. Or rather, he found us.

After making a post to a certain front page of the internet that had a local forum on it, he was one of the first to take real interest and initiative. A 24 yr old from a tiny town in the Midwest with a small masochistic streak who was the first genuine freak we’d met, even if he didn’t have much real world experience under his belt.

After chatting for a few days & showing him we are very real and I am very fuckin’ horny, he offered to drive an absurdly long way to fuck my brains out. What actually happened was me fuckin’ his brains out, but if I’m honest is totally fine too. The whole thing was like an all you can Chinese buffet, even if you get full there by the time you get home you’re fist deep in a bag of Lucky Charms.

After seeing some pictures of what he had to offer, it quickly went from the on-site messenger to text & Snapchat. Eventually leading to a video chat where W laid in bed next to me as we discussed all number of ungodly things. I showed him my toy collection (cackled at his recoiling from my crucifix dildo) & let him pick my dress for the night we were meeting him. Of course he picked the most conservative dress I own, rightfully dubbed the Easter Dress. I have nothing but curiosity for people who find and keep religion & he was definitely playing into that whether he knew it or not.

The night finally came and I had to find a way to sneak an entire small child sized purse full of dildos, vibrators & lube out of the house and into the tiny car sitting in our driveway. If it wasn’t for W being my partner in crime with the sexual shenanigans I’ve done (and he’s watched), there’s no way I could successfully pull this off.

We piled ourselves and our equipment for the evening into the car & started towards our date for the evening as I sent him some texts to try to make sure he made it to the bar in one piece and gotten himself comfortable. Once we walked in, it was pretty clear he had. I walked up and following through on (almost) exactly what I said I would do planted a big, lip gloss filled kiss on his confused face. We made our way to a booth, dragging him along with us & sat down to get the night started.

Now that I’ve rudely set the tone for this entry, come with me if you would to a dimly lit dive bar (again) somewhere in South Lite™, USA. I had spent the last 36 hrs or so sans panties or a bra (harder to get away with in my house than you’d think) and showed up to our little date still abiding by the rules set before hand. Understandably, he wanted to get to know us (explain himself?) a little before we did the deed. Nervous small talk & drinking go hand in hand after all. All I could think to do is try to keep teasing his hand up my skirt.

This is where I got to really *meet* GCB, a truly heartbroken, repressed slut who really, really needed a good distraction. As it so happens, that’s my main talent. I had decided on maybe my second drink that if he agreed I was going to give him (almost) everything he’d asked for in the last few days leading up to our meet up. I made it my mission to reign good sexual karma down on him and get out some of my pent-up aggression from the last week of being someone’s digital fuck toy.

We headed to the hotel & I quickly jumped on top of GBC, letting W figure out what to do with all the stuff we’d just hauled up here. I was on top & riding his dick like I’d wanted to all night within a matter of minutes after the room door closed behind us. I started getting close to cumming for the first time pretty quickly as I felt my nails dig into the soft flesh on his chest. I pumped myself up and down on his cock, feeling my cum build up on his balls in a little puddle until he came. I rolled off & tried to sort out exactly where I’d thrown my dress so I could grab my drink & go out for a smoke with W to gaze cum drunk at the sunset.

This is generally how the rest of the evening went until I had completely worn GCB out and drained his balls to the best of my slutty abilities. But a few notable firsts were: he was the first *male* ass I’ve eaten, finger & plug fucked. While I’ll admit I probably came at the opportunity that is similar to the same blind enthusiasm a teenage boy has when presented with a consenting hole for the first time, but I maintain that my ass eating skills has only gotten better with age.

And riding someone while knowing they have roughly the same sized plug in their ass (although notably less profane in design) is a lot hotter than I imagined it would be. And how much guys can CUM with someone or something playing with their ass is another thing I wasn’t aware, but am now in total awe of. Mother Nature really played a sick joke on y’all when she put your g-spots in your assholes and then set you up to have the mind frame that playing with it was bad or weird.

His choking skills were what impressed me the most & his love of doing it probably what got me to cum so many times. He fell somewhere between “he knows what he’s doing” & “this is totally the move Ted Bundy used to incapacitate women…” Which, come to find out for me is the perfect Goldilocks zone of breath control. Turn me into your’ human squeaky toy by wrapping your hand *just like that* around my throat & shoving your cock as deep into me as you can, fuck yes. That’s as close as my sinful ass will even get to Heaven.

After fully exhausting my Good Little Christian Boy (who is actually like 6ft something), we left him to guilt scroll through his phone & sleep it off in the room for the night. We headed back home, earlier than usual to the surprise of The Old People™ & I hopped in the shower. I got all myself (and my toys) all squeaky clean and we headed upstairs so W could fuck my sloppy little pussy to sleep for the night.