A gay sex stories: The Milking Den Ch. 09: Chase Meets Max
Chase and Max’s beautiful, perfect bodies gleam on the couch. They stare at me, seated on a chair across them, like bunnies about to be devoured by a wolf.
I lean forward, sinking my elbows into my knees. We’d worked so hard to make today happen and I wanted everyone to have a good, wet time.
“Boys. The two of you will become very, very good friends today.”
Chase and Max’s oiled arms slide against each other.
“You will be edged until you cry. You will be totally used inside out.”
“But only one of you will get to cum and enjoy it.”
Chase and Max’s eyes widen. I imagine their jaws would drop if they weren’t strapped snugly closed with my ball gags. They glance at each other, whimpers catching in their throats. The reality of their predicament hits them: these boys are trapped in straight hell. Bound side by side with another nearly naked man, their thighs open, their bodies spread out for feasting. The only way out is to lean – physically and metaphorically – on each other.
And they signed up for this. Behind their outward terror, a dark and sweet longing unfolded inside their loins.
Chase and Max tremble as I waltz up to them. Time slows down in the long seconds that I take to cover this short distance. Mounting my prized stallions, I straddle their thick thighs, rubbing my thumbs on their bulges like ripe fruit. Against their manly self-restraint, my hands erode their pride and coax out soft, hushed moans. They dread how I’ll torture them, but they love that I make them ache so good.
“Who will the lucky fucker be?”
***
Chase is no stranger to you and me. He was my roommate for a while and had some issues with rent, so we had to figure out a payment plan that both of us enjoyed (The Milking Den Chapter 3). He then came back for a bit and stayed with me again, and we also had a lot of fun milking him in exchange for cash (Chapters 6 and 7). Now, he’s back visiting family and friends, and we just had to meet once more.
After all, I let him cum the last time – after being edged, objectified and used for a whole week – on the condition that we play with another one of my boys.
Chase had been hinting at it for a while too. In fact, he was the one who sparked off the topic. He kept dropping references about wondering how he stacked up against other men, and the way his cock stiffened in my hands when I mentioned it last milking was proof.
Max, too, is a bicurious muscle stud that wants to be worshipped. Last time, the personal trainer hit me up for a final hurrah to singlehood before getting married. Seems like the pleasure of being praised with word, hand and tongue was too sweet to resist. He’s here for a “private coaching appointment”.
Chase and Max moan softly, as if reluctant to intrude upon the straight space of their fellow prisoner, as I knead their full and thickening bulges. Chase looks up at the ceiling and Max down at his crotch, their gazes avoiding each other like repelling magnets.
“Come on, boys. You’ve already touched each other all over just now.” Chase sniffles. “Oh, wait – almost all of each other. Why stop now? You have so much to learn about each other.”
Max blushes a deep, potent red, intent on keeping his eyes off Chase.
“Do you boys want me to take your briefs off? Play with your cocks instead?”
Chase sniffles and manages a “yes” over his gag, and Max nods as his face tries not to crumble. My groping gets harder and stronger and both sets of hard, chocolate bar abs contract with longing.
“I’ll do it if you look at each other.”
Chase begs me with his puppy dog eyes and Max scrunches his face up in agony. This is torture for the hetero ego – it’s one thing to play captive straight boy with me, but to acknowledge that they’re lying side to side with another naked man?
“Come on, boys. Here, let me help you.”
My hands trail up from their bulges, sliding up their well oiled torsos to cradle their heads and turn them towards each other. Chase’s face quivers anxiously and Max’s eyes crack open with bitter acceptance. They share a poignant, pained glance, powerless to resist the stripping, denuding and total milking of their bodies and minds.
“Good boys. Now, who’s gonna get edged first?”
Max is the first to crack. He shuts his eyes in denial and makes a soft howling sound.
That’s my cue – it’s always more enjoyable to break the tough ones first. I pull Max’s snug blue briefs down to let his cock spring up happily. He might be doing his whole reluctant macho thing, but his dick is saying something else.
***
“Hey guys!” Max and Chase flash their winning smiles as I let them both into the Zoom room, but they both look a bit too formal as they meet each other for the first time. Which is to be expected, right? It’s not everyday you have a Zoom call with another straight-curious guy because you’re planning a milking date at a friend’s.
“Sup?” Chase grins, and Max waves back.
“How’s your dog?” I ask Chase, who told me about his pet the last time he came over for his week-long torture marathon.
“Aww, you remembered! He’s great, thanks!” Chase beams, a stiff weight releasing itself from his shoulders.
“That’s awesome! Yeah, so, shall we get started?” I respond, glad they’re both settling in. “Chase, Max. Max, Chase. Both of you told me you’d like to play with another guy, and I thought you’d be a good match for each other. I wanted to meet together so we could get to know each other, and maybe talk about what you want the session to look like. Chase, do you wanna start?”
“Yeah, sure!” I can see Chase lying back on his bed, holding his phone above him. “This was my idea, so, haha.” Chase ruffles his bedhead hair. “Yeah, I guess I’ve always been kinda interested in being captured and tortured?”
“And you like it when your captor forces you to perform, right?” I suggest, and Chase chuckles as he blushes. He does! He loves it when I make him flaunt his muscles and fuck for me. “Max, are you into this too?”
“Yeah, in a sense,” Max joins in, his eyes pointed upwards thoughtfully. “I’m a sportsperson, right? I’ve always wanted to be forced to compete sexually against another guy. It’s just different, you know? When it’s a man? You just feel like you can go all out and push, and not hold back!”
“Yeah, I get you, man!” Chase chips in.
“I’m so glad the two of you get along!” I gush, and Chase and Max whoop along. “I guess we’re doing this, then!”
***
I text them later on Monday.
“Hey boys.
We’re meeting this Saturday. Report at 2pm. We will be done by 10pm.
No cumming from now till then. You know I’ll know.
Report in tight briefs.
Douche first.”
***
Society demands a lot from men. Being powerful, confident, brave is not negotiable – men need to be this way or they are judged as weak. Chase and Max, and so many of my boys, are like that. Influential people in business and leaders of families, they invest so much energy into keeping up this facade of strength.
That’s why Chase and Max keep coming back. I give them this space to be unapologetically vulnerable. To beg, moan and weep as I torture them with pleasure.