Send comments on this story to jakerandy204 at gmail.com. Standard 18+ warnings apply, of course. Based on real people and real situations, but many parts are obfuscated.
I'm a late-30s, professional gay guy, divorced a few years ago from my husband after he decided to quit his job and move to another state (long story), and it's been a dry spell since. Dating at this age is the worst, and I am not interested in hooking up because I require a connection. Plus, I'll be honest, I only like normal guys - when I meet someone too traditionally masculine or feminine, I just don't find them interesting. I detest social media and I got over my "going to the bars" phase when I was 20. Plus I have a degenerative disability. All of this makes dating brutal for me - even though I know it's partly my fault. And then, sometimes it's easier to want what I can't have.
I'll get to the point, I promise. (If either of them read this story, by the way, they would know it's about them. I'm not really hiding a lot. If you're reading this and you think it's about you, please reach out, buds.)
I have two male friends, early 40s, that I find to be just stunning. They're each married to great women (so I presume they're straight, though they could be bi but haven't said it), and both are the perfect kind of average in their personality - fun to joke around with, progressive and polite, but they are still completely men. They each have kids, but even if they didn't, they'd be total dad types, in the best way.
One I'll call Rick. Rick is six feet tall (actually six feet, not by online dating standards) and has a hipster/cyclists body - lean and muscular. I can see heavy chest hair spilling out of the top of his dress shirts. And when he wears short-sleeves, his arms are very hairy as well. One time, without knowing what it would do to me, he flashed his pits and flexed his arms on a video meeting, just while we were talking casually, and I got raging hard. As soon as we were done, I had to go jerk off thinking about it. Unfortunately he has no ass, but sometimes still he will wear tight pants and I love walking behind him and seeing his cute if tiny buns move.
The other I'll call Brad. Brad is closer to my height, 5'10" or so, and has the same lean and muscular body type, but a little broader. His skin tone is more olive, and he also is fairly hairy, though less than Rick. Brad is a little submissive sometimes, maybe I'd call it overly deferential, and that can be a real turn on. One time we went on a hike together right after he had gotten off the stationary bike and he smelled great, even though I couldn't get too close.
I don't bike as much as them, but they occasionally go on rides together. They'll get into their tight bike shorts or bike bibs (even fucking hotter), and go off on 40-mile rides. I can only imagine what kind of sweat they are building up in their Lycra. I wish I could really smell it.
One Sunday they go out riding and stop by my house near the end of the ride. They've worked up a sweat and they knock and say that Brad got a flat tire and they happened to be nearby, so they stopped in for my fix-a-flat gear. I let them in, and as they pass, I can smell that raw masculine power. They bring their bikes in as I have a huge open-plan living area, and an area where I keep my own bikes. They take off their clippy shoes, and I spend time watching them bend and stretch in their lycra.
They're both out of breath and their tight clothes look amazing. I point Brad towards the tire repair gear in the hall closet, and he gets to work while I offer them something to drink. Rick says he could use a beer since it's the basically the end of their ride, and Brad chimes in and asks for one too. I grab us all three beers and crack them open.
We shoot the shit while Brad works on his bike. He's bending over a lot, and I'm standing fairly close to Rick at the kitchen island overlooking the living room, but I notice that Rick keeps getting closer and closer as we finish our beers, until we're joking around and he is close enough to just knock his shoulder into mine when he makes some reference. I'm a bit lost in revery and enjoying the show Brad is giving me, as he sweats and strains to remove his tire, repair the inner tube, and put the tire back on with clear efficiency.
After a brief pause in the conversation as Brad cleans his hands of the tire grease, Rick says, "I'm starting to get a little cold in my gear," and gestures to his cycling bib and now-open cycling jersey. "I was really sweating on that ride."
"Oh?" I ask, just a tiny bit tipsy.
"Yeah, man. I bet Brad is feeling the same. What do you think Brad? Did you sweat a lot in your gear?"
Brad, his hands clean and now just making sure his tire is aligned, is squatting down facing us, the bike in between, but his crotch is clearly visible. He reaches his right hand down and cups the front of his cycling shorts, his fingers stretching to his underside. "Yeah I'm still pretty sweaty. But I've been moving a lot getting my tire fixed up, so I haven't cooled down yet."
I gulp as I watch this show. I start to stiffen a bit, which is a problem in my loose yoga shorts, which I'm wearing without underwear because I didn't expect visitors mid-day on a Sunday. The beer, the intoxicating sweat, the tight clothes, and the raw energy is really getting to me. I know I'm about to make some bad - or great - decisions.
Rick, now close enough to me for me to feel his warmth, gently grabs my arm and says, "Here, feel mine - am I dry yet?" And he pulls my right hand to his crotch, and slightly under, until I cup him myself. I can tell he is starting to get stiff, and I can feel damp, warm, and masculine shapes. I tighten my grip slightly and can feel his balls under the Lycra, and under that, his hard, lean muscle.
"Oh fuck," I say, involuntarily. I'm now stiff as a board and dizzy with lust.
"Do you want to get closer, Jake?" Rick asks me, and I immediately drop down and bury my face in his shorts. He smells incredible. It's like all of the good smells of a real man - fresh sweat from a great workout, all testosterone, salt and musk. And down here, something else too - it's a warm and humid smell that makes my eyes roll back in my head. I'm only sniffing and rubbing with my face at this point, as I don't want my saliva to mix into what is too perfect. I can feel his bush under the lycra, his stiffening cock, his muscles and bones. Soon, Brad appears next to me, and I turn and press my face into his shorts while I keep one hand on Rick's now-hard cock sheathed in Lycra. Brad smells even stronger, somehow, and his scent mixes with Rick's on my face, and I can feel their sweat sticking to my nose, beard, and cheeks. Brad's cock is thickening in his gear, but I barely notice as his huge balls are my focus, their scent making me leak, I am sure.
Soon I hear and see cycling jerseys drop onto the floor, and bibs coming loose from shoulders. I stop them both with a gesture and turn to Rick, where I finish peeling off his bib until it's bunched at his hairy thighs, and I stop because I can't be bothered to finish the job. His fantastic cock juts up from a perfect, dark bush. It is perfectly average in thickness, but at least 7" long, maybe 8". It is sticking straight up, and from my knees I look up at this hairy, lean hunk and dive onto his balls, licking and sucking them, my chin resting on the sweaty bib still stopped at his thighs. I'm in heaven. But quickly I turn to Brad and strip his bib all the way off, so he is standing naked. I barely have time to notice his incredible cock because Rick tells Brad, "Get down there and help Jake." And Brad drops to his knees too, and we work Rick's sweaty bib off of him. I move on to Rick's dick while Brad is sucking on Rick's balls. Given Rick's length and how his cock points up, we don't get in each others' way. Too soon, I taste precum and pull off with a pop.
I lead them both over to the couch, and push Rick to sit down. I then guide Brad down to his hands and knees in front of Rick and push Brad's head to Rick's crotch, in order to worship his dick. Brad figures it out quick and starts to suck on Rick's long cock, or at least the first few inches. I get behind Brad and start eating out his ass. It tastes incredible - sweaty, musky and clean at the same time, and when my tongue gets a little ways into him, I can tell he cleaned and lubed himself up. Knowing he was prepared makes me moan very loud. I pull up and say, "Brad, you devil. You were ready for this. Did you know that, Rick?" I start fingering him, jumping straight to two fingers as he clearly has stretched himself before today.
Rick is breathing heavily, and he huskily says, "We had talked about stopping by your place sometime, as we both have had a dry spell with our wives, but that's as much as we discussed." His head falls back and he sighs. "I didn't know he was ready to get fucked. Brad, you sly guy, you'd been wanting this, hadn't you?" Rick asked. Brad responded by moaning something like "yes" as he continued to try to fit as much of Rick's long cock in his mouth as he could, gagging often. Rick starts taking charge more and grabbing onto Brad's head and guiding him up and down on his cock, as I start stretching Brad's asshole by scissoring my fingers open and spitting into his hole. He's a natural and takes it well, though the gagging may hide any protests, not that I care that much. His gagging is producing quite a bit of spit on Rick's cock, which I know will come in handy.
I run to my bedroom and grab some lube and return, with just enough of a break to cool my jets. I'm still hard, and now lubed, and I get behind Brad and try to push in. Now, the head of dick is very thick, and my 6" length isn't too far behind in its girth, so Brad doesn't take it well at first. Rick holds Brad's head down on his cock to keep him from being too dramatic about it. Clearly he wanted this, even if he didn't know how stretched he was going to get. It works well enough (even if Brad keeps choking and Rick has to pull him up for air), and eventually he's loosened up enough to enjoy it. I reach around and I can feel his semi-hard, but still-sweaty cock swinging between his legs as I really give it to him hard, with steady strokes. I'm holding his hips with my hands most of the time, but occasionally pulling on his balls too. But I'm getting too close.
"Your turn," I say to Rick, and pull Brad up a bit by the torso to show him it's time for him to sit down on Rick's dick on the couch. He seems dick-drunk already as he somewhat stumbles up onto the couch to straddle Rick, who scoots down to make room. Brad sinks his hairy ass nearly all the way down onto Rick's spit-covered dick, not realizing how much longer it is, as his sighs turn into a more painful sound as Rick's dick goes deeper than mine had. He pulls up, I add a tiny bit of lube (more for the psychology of it) and Brad sinks down again as I push on his shoulders and Rick grabs onto his Brad's thighs and pushes down.
Brad sinks down easily this time on Rick's thinner dick, but moans excessively. He's hard again right away, so he must like that prostate stimulation of this position. I stand up and hover over them, rubbing Brad's back as he takes that long cock, and running my hand along Brad's hairy crack and ass. He's starting to pant and moan, and I can see drops of precum flowing from him and onto Rick's hairy chest. I grab some poppers from my stash of weed and mushrooms in a living room drawer, and I uncap the bottle and press it to one of Brad's nostrils, closing the other, and tell him to inhale. He does and I watch as his eyes dilate. One hit should be enough for this newbie.
I go and grab Rick's discarded cycling bib and take a huge sniff and almost pass out from the pleasure of it. I get the sweatiest part and bunch it up a bit and hold it in my hand, and return to where my two married hunks are moaning and fucking. I get behind Brad, and make eye contact with Rick. I put two fingers up, like a peace sign but the fingers pressed together, and push up in the air. Rick's eyes widen and he nods yes. I add more lube to the mushroom head of my cock, already swollen and red with excitement.
"I have a surprise for you," I huskily say into Brad's ear. "Open your mouth." He opens up and I shove the sweaty bib in. He struggles a bit and moans, clearly into it but confused and surprised. I look at Rick, "You're going to want to hold on to him for this," I say, and Rick grabs Brad tight, bringing him down so they're chest-to-chest.
I aim my cock at Brad's entrance and push, and he growls and shouts into the bib, and struggles against Rick's tight grip. "It's ok bud, you can take it. I know you can. Just relax." I pet his back gently and push a little more, finally making a tiny bit of progress, my thick head squeezed very tight into the first few centimeters of his ring. "You were made for this bud. You feel so good already. Do you want me to stop?" I ask. He nods his head yes vigorously, so I pause. "Are you sure?" He pauses and he shakes his head a tiny bit. "I knew you'd like this, but let's make it a little easier this first time." I back off and start slower, adding fingers along with Rick's slow-thrusting cock. Eventually I'm able to get three fingers in, which is a start. Brad continues to moan into the bib and sweat is starting to run down his back, and I can see he is drenching Rick below him in his sweat. His arms are around Rick's neck, and I can his hairy pits are leaking onto Rick's shoulders. They both smell incredible when I get close. I can't help it, and I bite Brad's shoulder, not very gently. I reach between them and Brad is mostly soft at this point, and I cup his semi-soft dick and huge balls, which for some reason really turns me on. I'm ready to try again.
Rick, meanwhile is continuing to slowly thrust and moan, trying different angles, and on one of his upward thrusts, my dick joins his and I make it about half of an inch in. Brad really shouts and starts crying now, my thick head being more to handle than the three fingers. I don't know if he's been fucked before - but he certainly has stretched his ass in preparation for today at least. But I am certain right now, he is being double-penetrated for the first time in his life, and I know he will remember this forever. The two men he is closest to in his life are now inside him, together.
"Think of it like a long climb, where you just need to push through the pain," I huskily say as I feel him shivering and spasming. I'm trying to hold back, but I growl out when I realize I can feel the underside of Rick's dick massage the underside of my dick as he thrusts in. I'm just barely inside still, maybe an inch now, but I can't hold back anymore, and his ring has already been breached, so on Rick's next slow thrust in, I push in more, basically all the way. Brad really must feel it, as his back arches and his head flies back and lands on my shoulder. I start sticking my tongue in his ear, which makes him moan like crazy. I stay embedded in him deep as Rick's longer cock thrusts out and in, deeper than mine can go. I'm the steady stretch in Brad's ass, and Rick is the thrusting force.
I can still smell their full-strength sweat on my face, and I can smell the sweaty bib in Brad's mouth, and I can feel Rick's cock massage mine on his thrusts into our friend's hole, and his balls hit my balls when he gets all the way in Brad's stretched ass. All three of us are hairy men, and I feel the scratch of real mean taking their pleasure. I pull out about halfway and slowly push in, and soon both Rick and I are slowly thrusting in and out, not even bothering to match rhythms in the frantic chaos of double-fucking our friend. I reach between them, my two hairy, married men, and I can feel a mix of sweat in their hairy chests and then Brad's precum on their stomachs before I reach Brad's completely engorged dick. It's a shame he's such a great bottom, because his dick is like the combination of the ones ruining his hole right now - long and thick, perfectly proportioned head. I start to jerk him off and he goes crazy, and within a few seconds he is coming so hard that his ass and body pushes me out with its twitching, and he goes practically feral on top of Rick's dick as his whole body spasms, and shouts in pleasure into the bib in his mouth.
As he cums, I grab the head of his cock and catch his cum in my hand, cupping as much of it in there as I can for a final surprise, though the remainder mixes in with the sweat on Rick's torso. All of the force of his orgasm made Rick close, I can tell from his now-frantic thrusting, so I start massaging his balls with my free hand, which are now covered in sweat and lube, and he makes an obscene growl and buries his cock as deep as it will go into Brad and I am pretty sure I can feel the pulsing of his balls as he releases his cum into Brad. I don't let him enjoy it for too long as I pull his cock out, spread Brad's own semen on the fat head and first two inches of my cock, and thrust into his loose, dripping hole as fast as I can, so more cum doesn't leak out. I want him to feel three men's cum in his ass today - mine, his own, and Rick's, and that thought, plus the scents of three masculine men fucking their brains out, and the loose and cum-lubed hole of one of my two favorite men, makes me quickly shoot my own huge load into Brad, who has basically stopped responding, panting and still moaning on top of Rick.
After I unload and stop my own twitching, we help Brad lay down on the couch, and I grab Rick's lazy hand and push three of Rick's fingers into Brad's hole. They're both sorta out of it - likely because it's their first time with the pleasures of sex with men. I run to my bedroom and grab a medium-size butt plug. I lube it up on my way back, using the mix of cum, lube and more that's on my dick, and Rick removes his fingers and grabs Brad's legs as I insert the plug into Brad, still fairly out of it. I don't want him leaking everywhere, of course, and he's filled with at least two and a half loads.
We watch TV for a bit, close to each other but not cuddling, under some throw blankets I have on the couch. Brad comes to his senses again after a few episodes of a sketch show, but they both seem to be rather shy all of a sudden. "Off to the showers," I say, and I pull them both up, acting as normal as I can. I end up walking behind Rick, who so far has only received head and fucked, but not yet taken a man, and I watch his hairy crack and think, "I bet I can get Brad to hold Rick down as I take his ass for the first time, whether he's ready or not." I stop by my stash and grab something to make that go a lot easier, as soon as we've showered.