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.

Make Me Cum // 0:12 – 0:19

After the dizzyingly good experience that was B, I was anxious to see what else was out there. If I could find one of him, I could find more just as easily, right? God, I’m a fucking idiot sometimes.

Enter the very big dicked Mr. Mackey. We met him on our usual site & chatted for an evening the same week we were due to meet up with B. Set a meet up date for the following weekend & once the day came I got all prettied up and we headed out the door. No real communication or interest shown on his part (or mine really). Big dick meet eager, free pussy. You know the drill.

After the first person to random ditch out, I was nervous. I knew that was just part of doing this, most people talk a big game and very few can back it up. Not everyone can fuck a total stranger while her happy husband watches and that’s okay, we’re not expecting everyone to. But let me say this now, if it isn’t something you think you’ll be okay with or even get into, do not fuckin’ do it. You’re gonna have a bad time even if you are able to cum and I think Mr. Mackey is a prime example of that.

The first half of the night is honestly the most interesting or it was for me at least. We showed up at the spot he was meeting us a couple hours early & had dinner and drinks. Eager to test out my new found freedom and not thinking Mr. Mackey would actually show, I stumbled my way to the brave/stupid level of being drunk and started to eye fuck anything in the room that seemed of interesting. But I’m sure it came off more Ted Bundy than Peg Bundy because I’m a little rusty from years in monogamy. Up until a month or two ago, I didn’t even pick up on when I was being checked out in public.

The night wears on, I realize to my dismay I’m bad at IRL hitting on men AND women & Mr. Mackey keeps pushing us off. He’d been at work all day before and then was meeting us so we tried to cut him as much time slack as possible. Finally, he shows & seems…completely unsure of what he’s doing there with us. I ask him what has become the standard test questions: who is your favorite comedian and least favorite serial killer. He gives me what I’d now consider non-passable answers, but I’m drunk enough & he’s cute enough to where I don’t care.

We move from the original bar to one that’s has extremely unique décor that I love. Dollar bills stapled everywhere & a dive bar vibe to die for. I sip my drink occasionally looking up into a sky full of capitalism and excess while we exchange some awkward small talk. The night wears on, he tries his best to keep up in conversation, but extremely apparent (to me) if we were meeting up for a normal date, I’d have called it quits by now. But I’m more than willing to put aside almost any personality flaws for a big dick or pretty lady. I’d like to say this isn’t a mistake I’ll make again, but I think we both know that’s a fuckin’ lie. To put a spin on the immortal words of John Waters: sometimes boring & cute is enough.

Sipping on the last of my Screwdriver from the Dollar Den, I ask if he’d like to get a hotel & have some fun. That was the whole point of this exercise, wasn’t it? He agrees and we stumble out the door. I pull him to the side and step up on my tippy toes to make out with him while W walks off to get the car ready. I’ll give Mr. Mackey props, personality wise we were the non-attracting kind of opposites, but the way he kissed made me dripping wet. Any apprehension I had left my head & off to the hotel we went.

He was gentlemanly enough to stop by & grab some more booze for him and me. And decent booze at that. We meet up and crash into the room, W getting his normal spot ready and turning on the TV. After the first experience W had, he knows now that every hotel I’m in is going to get the full vocal effect of me getting my brains fucked out if it’s done right and he wants to make sure none of our temporary neighbors think I’m being murdered. He wisely turns on the TV to Comedy Central a.k.a. The South Park Channel & cranks the volume. I was so ready to finally be fucked senseless that I didn’t even notice at first.

Clothes were thrown to the wayside, & I finally got to see what I was working with in person. It’s glorious. A fat, long, meaty cock for me attempt to wrap my holes around. Wrapped & ready to go I climb on top & squish it into me. I start riding away, grinding my hips until I get closer and closer to cumming. I’ll admit, at this point, I’m not really paying attention to him. It’s very clear, this is a O.a.D experience, but if you’re this far into it & the only problem is the guy seeming vaguely uninterested, you got to see that shit through. I pound my way to loud, orgasm on top, thumping my ass into his thighs while cartoon Mr. Mackey lectures the boys about some dumb thing or another on the TV. I feel the familiar wave of good brain chemicals sweep down my spine & into my needy little body and I start urging him to cum. Begging for it. He grabs my hips & pushes into me, I can feel the little condom nub rub against the bottom of my clit. I giggle & climb off, out of breathe after having given my thighs the work out of their life.

I collapsed on the bed besides him, took a sip of my drink and realized: this guy is definitely out of his element. Post-nut clarity as it’s finest. I do my best to work another play session out of him, but either the beer he grabbed hit him harder than he thought or the fact another dude was watching him pound a chick finally crept it’s way inside of his head and took root. Maybe it finally dawned on him that he was balls deep in a girl who’s test questions had been: his favorite comedian and least favorite serial killer & maybe, just maybe, post-cum he realized that was definitely not his bag.

After a small break, I had him gloved up again & back on top. From W’s account of things I was moan-yelling at him to go harder/faster (which with that cock, he definitely could have) & he just sorta…didn’t. W thought it was hilarious, my pussy on the other hand did not. After that I threw in the towel & accepted my fate of a single orgasm. I mean, it was a good one, but I’m greedy. Even if he just wants me to use him like a human dildo & starfish the whole time, I’m still down to try and get mine more than once.

Playtime ended disappointingly fast after that. I gave him one more regrettable kiss goodbye & made an attempt to make nice then we got the fuck out of dodge & snuck back into the house around 3-4 am. The next day I went to send him a thank you message & found us blocked. Everywhere. I laughed my ass off and went about the rest of my day secure in the knowledge that while he may not have said anything, I successfully picked up on the vibe that he was not interested. Kudos to my socially delayed ass on that one to be honest. From the being a woman who can’t pick up on when men are hitting on her to being able to vibe check a casual sex encounter, I’d like to think I’ve come a long way for such a short time.

Like I said earlier, now a days I try to look less for dick size & more for personality. Try being the keyword, I’m still a dirty size queen slut at heart. However the knowledge I had before this still stands true: sex is so much better when you can at least tolerate each others company outside of fucking. And casual fucking is way more fun when both people are completely totally into.

Left Brain, Right Brain // 1:47 – 2:21

We quickly (and excitedly) made our way to the dive bar Mr. Martini had in mind for the evening & took our seats towards the back. I anxiously waited & sipped on my Screwdriver while eye fucking the gorgeous waitress and complimenting her/her tattoos any chance I got. After 10 minutes inside with the music & drunken yelling, I realized I wasn’t tipsy enough to be exist in the dimly lit booze den so we made our way to the patio to finish our drinks and wait.

After sitting out in the sunshine for a few minutes, admiring the sheer amount of dogs people bring to this place we see Mr. Martini strolling up, looking fairly determined and confident. Quite the change from the puppy dog I saw in his car at the gas station parking lot a few evenings before.

He walked up, found us & got himself (and me) a drink from the bar. We sat as the sun sank down behind the shimmering, ugly buildings surrounding us, shooting the most casual of shit considering the intended outcome of the evening. W & Mr. Martini discussed work, I made dick jokes whenever the opportunity presented itself & went on a full spiel about how if Martini wants a dog & can afford a dog, why not get one.

Dusk drops around us as I suddenly put the night’s most important question on the table: are we getting a hotel room or can he host? Because I’m mostly certainly down to fuck.

Mr. Martini pipes up that he can host & his apartment is just down the street from where we were sitting. We gather ourselves together & head his way as he does the same.

We pull up to what I can only describe as something that looked like dozens of aluminum shipping crates stacked on top of each other to make a building with windows & sliding glass doors installed. We make our way through the lobby & up to his place, my eyes burning at the sudden and intense brightness with which everything inside this opulent abode is lit. A quick knock on the door & we’re inside being greeted with the perfect thing: an offer of a dirty martini (with delicious jalapeno olives) & the sound of quiet music.

I slip off my shoes and marvel my way to his living room, noticing YouTube music playing some John Popper (ew, but whatever) jam session video. I take my seat on the couch as W spies a big, single seat chair & plops down in it, taking it as his own.

Mr. Martini brings me my drink & sits down on the couch next to me with his own. W being the smart man he is realizes, not a lot is going to start with him in the room. Both of the people expected to fuck are pants shittingly nervous & while there’s no real tension in the room regarding his presence, I’ve been monogamous for well over a decade – I had no idea where to even start.

He excuses himself for a cigarette & the next thing I know, I’m kissing and groping on Mr. Martini, pulling his pants down/off. I don’t even hear W come back in, but after we take a quick breathing break from stripping down and sucking face I notice him sitting in that big, poofy chair, watching the night unfold & smiling ear-to-ear. I took this as a big, beautiful green light to proceed however I wanted to…and I did.

Most of what happened next has been lost in a blur of time, excitement & alcohol.

I remember hearing him (Mr. Martini) gasp as I took his dick in my mouth, sucking & licking it like the last popsicle of my favorite flavor from the freezer.

I remember riding him and trying not to laugh because he was very much trying to bring male porn star energy and very much had no clue how to do that.

I remember cumming at least twice. Both times from his awesomely attuned hands.

I remember taking a smoke break & having him play with my pussy as I looked out over the balcony railing to the two big, gawdy Catholic churches that faced his place. I laughed at the lovely coincidence of it all and pushed his hand deeper into my cunt.

I remember him licking my armpits & sucking on my toes. My first fetish fun in forever.

I remember him asking (very nicely) for a spit-covered handjob and realizing he’s found the ONE thing I’m not at all skilled at sex wise.

And I remember us both deciding mutual masturbation was the best way to end this night. I laid back on his couch as I cranked his cock, fingering and eventually fisting my pussy as I watched. Having done live cams for years on end, I always wondered how I’d feel if someone was to give me a show in real life and as it turns out, it makes me cum just as hard if not harder than being on cam.

Mr. Martini and I collapsed in a pile of sweat and cum, opposite each other on his fancy couch. I played with his feet & traced his birthmark that looked a bit like Orion Belt sans the belt as the music played in the background & I finished the last drink he’d made.

We said our goodbyes & made our way back to the car, W & I all too excited to get home and jump all over each other again. I got him home and immediately let him dive into my ass, bouncing up and down on his cock, trying not to scream-moan the whole house awake.

The first one’s always the hardest, but Mr. Martini made it pretty damn easy and fun.