Dom's Little Black Book: Fiveway (Patreon)

As a gay man, I can tell you that receiving an invitation to a friend’s pool party is a fairly common occurrence. It is also pretty common for that pool party to be clothing optional. And it’s certainly not uncommon for the people at these clothing-optional pool parties to pair off and find a room somewhere to have some fun. Like the room with the sling set up in it, if they bother to get out of the pool at all (silicone lube is handy, y’all).

On this particular Saturday, the party I was at was beginning to wind down. It had started in the early afternoon, and as the evening drew to a close, guests began slowly leaving the pool and hot tub. The hosts were friends of mine, and I would be crashing there for the night - something I usually do if I know I’ll be drinking late into the evening. By 10 p.m., the only people left are me, the two hosts, and another friend of theirs. I specify “of theirs” because, for whatever reason, this individual did not seem particularly into me.

One of the hosts was Daddy M, who I previously wrote about tag-teaming the sexy Bartender with. At this time, he was living with his then-partner Kev, and I would frequent their place often to enjoy their pool, hot tub, and sex with the both of them. The three of us had been chatting up a boy online earlier and made plans to have him come over once the party was done. The aforementioned sling was set up in the bedroom, and we were looking forward to getting him strapped in it.

Their friend was pretty drunk, and all three of us were wondering why he was still there. It became apparent that the reason he was sticking around was that he knew about the fun we had planned and wanted to join in. His desire to stay was more than a little strange to me, as I had the impression that this person - we’ll call him Jerk - did not like me in the slightest. He was always finding ways to be rude or a smart ass and enjoyed acting like he was better than me. Just an all around douche. Then it clicked – the reason this guy didn’t like me was because he like-liked me - or at least was jealous enough of my sexual relationship with Daddy M and Kev that he wanted a piece for himself.

I’m game – hate fucking can be just as much fun as the regular kind, sometimes even more so. At this point in my life, I had never been involved with more than two other people at the same time, and even that was still fairly new. Five people seemed like it was either going to be amazing or total overkill. Either way, it was certainly going to be an interesting night.

We all move into the bedroom once the boy arrives. Kev and Jerk are on the bed while Daddy M and I help the boy undress. Manhandling him between us, me at his front and Daddy at his back, we strip him slowly, turning him around to trade off kisses as we get him naked.  He paws at our dicks, which were never put away from the pool party, before we help him into the sling.

Daddy decides to go first and has me grab him a condom and a numbing lube. He rolls the condom on, applying the lube to his cock and Sling-boy’s hole before wiping his hands off on a towel. If you’ve never used numbing lube before: be careful. If you get any of it directly on your dick, say goodbye to cumming anytime soon. So when you use it, make sure you clean off your hand before you forget about it.

Daddy M starts fucking the boy slowly, waiting for the lube to take effect and allowing him to get used to the thick beer can of a cock in his ass. Seeing as it’s available, I move around towards the top of the sling so I can get my cock in the boy’s mouth. I hold the back of his head steady while I feed myself to him, fucking the first few inches of my dick in and out of his mouth. Eventually, Daddy starts thrusting hard enough that the sling is moving too much for me to continue, but thankfully there are other people in the room I can enjoy. I climb onto the bed on the other side of Kev and join him and Jerk.

So like I said before, in literally every interaction I have had with this guy up to now, he has been nothing short of a complete asshole to me. But as soon as I’m on that bed, he swallows my cock straight down to the root before I can so much as say, “hey.” I also hate to admit it, but he‘s talented too, with no gag reflex in sight. Now, I’m not someone who complains about a good blowjob, so while Jerk gorges himself on my dick, I lean over and start kissing Kev. I’m more than a little tempted to get rough with him - need to see about putting him in his place for how he was acting at the party earlier -  but I don’t want to kill the mood in the room, at least not before I’m finished. Let him hate me all he wants, but he’ll never be able to unsuck my dick.

Once it’s my turn to fuck Sling-boy,  I pull my cock out of Jerk’s mouth to roll on a condom of my own. I lube up the same way Daddy did and get in position, pushing the head of my cock into his hole. Daddy is right behind me, his mouth kissing my neck while his hands touch my chest and stomach. I start to relax and take the whole scene in. It’s my first orgy - anything more than four people is an orgy, right? - and I’m in my early 20’s, just starting my sexual journey. Who knows what kind of things I’ll get into one day? Well, you guys know.

I look down and watch as the boy swings in time with my thrusts, the chains of the sling rattling against its frame. Sling-boy’s eyes are closed, and he moans softly each time my dick slides in and out of his hole. I try to vary my strokes, aiming for his prostate but also trying to keep him from expecting what’s next. I stop pumping my hips and instead grab the chains and use them to pull the boy on and off my cock while I stand stationary. Once I’ve figured out the rhythm, I start to pump Sling-boy on my cock hard and fast, leaning back and kissing Daddy M at the same time. This is great.

I look over to the bed, and see Jerk sitting up against the pillows, with Kev’s head in his lap, sucking him off while sticking his ass in the air. I pull out of the boy to give Daddy another turn; I think I’d rather get inside someone else for a bit. I remove my condom – again making sure not to get any of the lube on myself – and climb back onto the bed, behind Kev. I grind my cock against his ass, and on instinct, he pushes back against me, gurgling a moan out around the cock in his mouth. Seeing as I know Kev and Daddy M so well, there are fewer concerns when it comes to protection. I grab some regular, non-numbing lube and slick my cock up before pressing in raw.

Kev can’t seem to suck and get fucked at the same time, so while I’m fucking him, he’s got his head to the side of Jerk’s lap, stroking his cock with his hand. I make eye contact with Jerk and give him a cocky smile while I fuck Kev into the mattress, the older bottom groaning with each snap of my hips. He gives a meek smile back, and I start to fuck Kev even harder. I’m still not entirely sure what’s going on in this guy’s head, but I don’t care anymore. I know he’s into me, and now I’m just wondering what else I can get him to do…

I can hear Daddy still banging away at the boy in the sling behind us, and I move so that Kev and I are both lying on our sides. Jerk is still watching us intently, playing with his own cock now that Kev has become too engrossed in getting his ass reamed. Kev reaches down to grab himself, any other cock aside from his own and the one in his ass long since forgotten. I pick up the pace, slamming myself into him, trying to push him over the edge. Just a few minutes later, Kev shoots his load all over the bed and collapses on top of it, incoherent and out of breath. Job well done, me.

Unfortunately, that also means I’m going to need to find someone else to help finish me off – Kev is the type of bottom that needs a break after he’s spent himself. I can see Jerk staring at me as I start to stroke myself for a moment. I move Kev out of the way and pull Jerk over, kissing him fiercely. I’m not interested in being sweet or sensual, I just want to cum, and he’s going to get me there.

I don’t get any complaints, and eventually, he takes some initiative and starts to knead my balls. Should have seen that this bitch was into me sooner. I bite at his lip and kiss him harder, inching closer and closer to cumming. To my right, I can hear the loud slams from Daddy and the boy in the sling, the clangs of the chains only barely drowning out the slapping of skin on skin. I growl into the Jerk’s mouth, and then I’m cumming all over my stomach, gripping him tightly to my side.

I flop back and relax my hold a little, catching my breath and savoring the warm afterglow. I look over at Jerk, hard cock bobbing free in his lap. Looks like he could use a hand.

Meh. ¯\_(ツ)_/¯