Daddy Tim's Gangbang

I’ve known Daddy Tim longer than I’ve known just about any other sex buddies online. We met on gay.com over a decade ago, back in the service’s good years. We hit it off immediately. I’d travel out to Ann Arbor, where his executive’s salary afforded him a beautiful house on a double lot near one of the city’s more extensive parks. I’d enter through the rear porch. Then I’d jaunt down into his basement bedroom, where I’d find the latest boys he had to share. Sometimes they were tied up. Sometimes they were just lying there in the dark, waiting. Once in a while, there’d be two or three of them.

Daddy Tim has a way of attracting college boys. He lives in one of the state’s largest college towns, after all, and every year there’s a new crop of freshmen, free for the first time from their family and old friends, and anxious to learn from a mature top. And sometimes the top’s buddies. That’s where I come in. I’ve always been the buddy who gets to sample the holes after Daddy Tim’s trained them. Then I get to give a blunt evaluation. Something like, “Yeah, he’s good all right.” Or maybe, “Damn, you’ve trained this boy well.” Once it was, “This one needs a little more breaking in before you let the real rodeo cowboys ride.” That went over well.

Daddy Tim is a good fifteen years older than I. He’s actually a granddad, several times over. I think even he’d agree that he’s not the most typically handsome guy in the world, but in Ann Arbor, he’s like two hundred pounds of ground round thrown into the tiger cage. The young cats are all over that shit. Tuesday he messaged me in the middle of the morning to ask if I wanted to come over to his place:

daddytim: cum and fuck the trainer today with me and my buddy bill...the trainer wants lots of cock...its been 2.5 weeks since he was fucked

The trainer is his nickname for his latest obsession. That’s the guy’s profession; he’s a personal trainer for one of the larger and pricier gyms in the area. Daddy Tim has turned the guy from a total top to a whore bottom in the space of less than a year, ever since last July when he first convinced the guy to give up his hole. All I knew about the trainer is that he was supposedly gorgeous, built, and totally insatiable when it comes to getting fucked. He’d also never been shared, so getting an invitation made me sit up at attention:

thebreeder: what time?
daddytim: 12:30
he would have no idea another guy was showing up.....
he is obsessed with getting cock today
and u would like to be around my other buddy he is 60....very hot....and sexy...i know u lke older men....
this is the trainer’s email to me...10 seconds ago
I'm beside myself with lust that I'd probably almost fall into the "menace to society" category.  Like I said-good thing you've arranged backup for today.  Insatiable doesn't even begin to cover it.  I hope Bill doesn't feel rushed.  I want to walk out of there completely filled up with cum, and your friend satisfied with my performance that he wonders when the next time will be.
thebreeder: 12:30 is good with me.
daddytim: now i will be presenting him as my pussy boy
so just call him fuckboy or pussyboy or anything with boy in it
he wants to be fucked silly
his last email to me:
I need an uninterrupted, complete dicking that only you can provide.  I'm telling you, when I leave there I want to be so worked over that I can't even complete a simple sentence
he doesn’t know I’ve invited you
you will be the star of the show
you have the biggest dick
I want you just to walk in and surprise him with how big your dick is, ok?
thebreeder: Can do, man. It’s a date.

The drive to Ann Arbor is nearly an hour for me, but the meeting was early enough in the day that I could slip away without much hassle. After I parked in Daddy Tim’s driveway, I let myself in the porch door, kicked off my shoes, and made my way downstairs. It took a minute for me to blink the sunlight from my eyes and adjust to the darkness below, but when finally my vision cleared, I could see enough to remove my clothes and join the party in the bedroom next door.

When I walked in, I saw that Daddy Tim had managed to round up a fourth top—a skinny younger guy I recognized from online but whom I’d never actually encountered in the flesh. The kid was finishing up as I stepped into the bedroom, pulling his condom-covered dick out of the bottom’s ass. I couldn’t tell much about the trainer from his position, and how crowded it was around him. All I could really tell is that he had a narrow waist, broad shoulders, and a perfectly round, muscular ass. Daddy Tim stood at the bed’s far in, plugging the trainer’s mouth, while another man referred to as Daddy Bill was taking the place that the skinny guy had just vacated. The skinny guy yanked the rubber off his little dick, threw it in a waste can, and scampered out as if he had somewhere to be. So much for meeting him.

“Oh look,” said Tim when I started stroking myself to hardness. “Your other daddy’s here. Daddy Mike.” I’m still not sure why Tim was introducing me with a name that wasn’t my own, but for a shot at that muscular ass, I was willing to go along with it. “Daddy Mike’s got a big dick for you. Bigger than you’ve ever had,” he said. All the trainer could do was grunt and choke on Tim’s cock.

Bill turned around to look at the eight inches I was stroking. His eyes widened. Like Daddy Tim had said, even at sixty-one or sixty-two he was a handsome fucker; he had a furry chest and a body that was still muscular and athletic. As he slid back and forth in the trainer’s hole, his head tilted and leaned to mine. I met his mouth in a kiss. The guy kissed well. Well enough, in fact, to distract me from the fucking at hand for a few moments. I ground my hard dick against his thigh, and ran my hand up and down his ass and back. He thrust back and forth while we made out, then abruptly yanked himself out.

From the bedside table, Bill grabbed at a container of lube. He squirted some onto his hand and then slapped it onto my dick, rubbing the cold good up and down my inches. “Your turn,” he said at last, nodding at me to take his position.

Daddy Tim had been keeping up a running commentary while he fed the trainer his dick. “You should see your daddies making out while they use your little boyhole,” he growled. “Yeah, they’re all turned on and shit while they’re fucking you. Now it’s Daddy Mike’s turn.”

I’d forgotten that my name was supposed to be Daddy Mike, frankly, and I’m afraid I actually paused and looked at the other guy. Then I remembered. “Yeah,” I said, trying not to laugh at myself. “Daddy Mike’s ready to fuck this hot boyhole you’ve been telling me about.” I crouched slightly to get at the right height, and slid inside.

For someone who was a total top nine months ago, the trainer was remarkably loose. Then again, he’d already had three tops inside him by the time I got there. He felt slick and hot and great around my meat, though. For the first time I was able to get a good look at the guy’s body—it was fucking fantastic. He couldn’t have been any taller than five-foot-five or so. He was a compact, tiny-waisted fucker with shoulders so broad that he looked like he’d stepped out of a Tom of Finland cartoon. Though his chest was relatively smooth, his legs and enormous calves were bristling with thick dark hair. When he turned his head back and forth on Daddy Tim’s dick, I got the impression he had a short goatee.

That was then I felt the coldness in my crack.

While I’d been accustoming myself to the trainer’s ass, Daddy Bill had squirted more lube into his hand and began rubbing it into my hole. He kissed my neck and shoulders, which is always something guaranteed to reduce me to a puddle of Jello. His bearded lips traveled up to my left ear. He growled, “You are so damned sexy, boy.” I murmured thanks, still fucking as he worked a finger into me. “Maybe it’s your hole I should be fucking.”

I had two thoughts at that moment. One was panic, because I wasn’t at all prepared to be fucked. Not mentally, and certainly not from a standpoint of cleanliness—at least not beyond the depth of an inch. The other was a flattered pleasure in having a handsome and unfamiliar daddy growl obscenities in my ear about how fuckable he found me. I let him continue to explore until he had his index finger up to the second joint. It was at that point, with him creating sensations I hadn’t felt in a very long time, along with the gentle nibbles he made at my earlobe and neck, combined with the sensations of my dick slipping and sliding in and out of a very wet and cummy ass, that I lost it.

“Fuck!” I said. My hips shot forward, carried by my orgasm. I plunged all the way in to my nuts, shuddered and shook, and shot my load as deeply into that muscular butt as I could.

When I was done quivering, Daddy Bill removed his finger, pulled me out, and pushed me over to Daddy Tim. “Make that pussyboy clean your dick,” he said. “My turn now.”

Tim stepped out of the way so I could feed the trainer my dick. Even though it had been in his ass only seconds before, he gobbled down with a hunger that astounded me. Meanwhile, at the trainer’s other end, Daddy Bill was fucking in the load I’d just left. His eyes were half-closed as he slipped in and out. “He’s a good boy, isn’t he, Mike?” asked Tim.

Once again, I didn’t remember my fake name at first. “Oh yeah,” I said eventually, once recognition set in. “He is one good pussyboy. You’ve trained this one right.”

The trainer grunted and groaned at the praise. His back arched and he thrust his butt higher in the air. Bill couldn’t contain himself any more. When he shot, it was with a spasm so powerful that he pushed the trainer onto his stomach. I pulled my dick out before he could chomp down on it. Then Daddy Bill fell atop the trainer and writhed around like a freshly-landed fish, as he finished coming. “Jesus,” he whispered, at last.

“I told you,” said Tim, smirking. “This boy is good.”

While I relaxed on the mattress and stroked myself, Tim took the trainer to the foot of the bed’s frame and made him clutch the curved iron railings. He bent him over and began fucking. “Jeez, boy,” he snarled. “You’re nothing but a little cum whore.”

“Yessir,” mumbled the trainer. His eyes were shut tight. “Daddy’s little cum whore.”

It was the first time I had a direct look at the trainer’s face. He was a handsome, handsome man. His chin had a cleft with a dimple. His nose was so blunt and flat at its end that he looked like an Art Deco Mercury, or the Leyendecker Arrow Shirt man. I already knew he was older than most of the twinks that Daddy Tim usually attracted, but now I could tell that he was no older than thirty-five at most. He could have had any man he wanted, but at that moment all he wanted were the cocks that his Daddy Tim gave to him—and he was willing to take them all without question. Daddy Bill got onto his knees and began twisting the trainer’s nipples to make him cry out. “Look at your Daddy Mike,” said Tim, as he slammed in and out of his hole. “He’s hard again. Did you like your Daddy Mike’s dick? You want more of it?” The trainer nodded his head.

“Make him sit on it,” I declared.

Tim withdrew from the hole and guided the trainer over to me. Obediently the muscle man hopped up onto the bed and straddled me. His head jerked back and he let out a moan as he lowered himself on me. “Come on,” I urged. “You know you want it. Take it all the way.” We both gasped as he sat all the way down. I noticed for the first time that the trainer’s dick was rock-hard, and dripping all over my stomach. “Yeah. Take it.” I let my head sink into the pillows.

Daddy Bill wrenched my legs apart, and pushed the trainer’s torso down. He was trying to enter him with me, I realized. He wasn’t hard enough, or big enough, to accomplish the deed. So after a couple of minutes of trying, he settled on jamming his thumb up my ass as deeply as he could, while maintaining eye contact with me beneath the trainer’s armpit. “Goddamn,” said Tim. “I was hoping to get my fuckboy opened wide with two dicks at once. It's his final frontier. Right, boy?”

"Final frontier," echoed the trainer in dazed agreement.

“Yeah?” I asked. I pushed the trainer up and off my dick, and rolled out from underneath him. “Then make Bill lie down.” My hole was getting a little sore from the unexpected invasion, I had to admit. Even in the days I was an avid bottom, decades ago, I never liked fingers very much. “I’ll double penetrate the little bitch.”

Bill immediately hopped into the hollow in the mattress I’d just vacated. His dick wasn’t big, that’s for certain. The trainer sat down on it and jerked around as if it were a foot long, though. I pushed his V-shaped torso down, spat on my dick to reactivate the lube and cum drying on it, and began to fuck it in. To make sure that Bill and I were both in the hole, I held onto his dick with my fingers, and kept my thumb atop my own as I poked at the hole. First I stabbed with my head. When I felt the ass open to take in with Bill, I thrust in another inch, and then another. Three inches was about all I was going to be able to get in, I could tell, but it was enough, both for my pleasure and for the trainer to know he'd been double-penetrated. “Yeah, boy,” I growled in the muscle bottom’s ear. “You’ve got two dicks in you at once. That boyhole's been DP’ed. How’s it feel?”

The trainer was in heaven. He couldn’t believe how slutty I’d made him. “It’s . . . my final frontier,” he finally said.

“You love being a little bitch for strange dick, don’t you?” The trainer nodded at my question. “You want another load?” This time, a nod wasn’t good enough for me. “You want another load? Tell me.”

“I want another load,” he whispered. “I want another load.”

“What'd he say?” I said to Daddy Tim in a regular voice, “I can’t hear your boy.”

“I want another load,” said the trainer, more loudly.

“Still can’t hear you!” I snapped.

“I want another load!” he shouted, filling the basement with a bass roar. “I want your fucking load, daddy!”

“I didn’t hear you say please.”

He began yelling at the top of his frenzied lungs. “Please! Please give me another load! Please gift your cuntboy with another load! Please! Please! Just fucking breed my hole, please!” Over and over he repeated his pleas, until I couldn’t take it any more. Bill’s dick slipped out when I shoved mine all the way in. I unloaded again with grunts and shoves so hard that the trainer’s head banged against the iron headboard.

There was a moment of silence in which I clung to the trainer's waist. Daddy Bill sat up and stared me in the eyes. His hand reached out, and then pushed the hair back from my face. Very tenderly, he stroked his fingers through my hair.

I was still panting when I nodded at him, turned on by that simple gesture. My vision hadn't even completely cleared. “Now what?” I said to the trainer. “What do you say?”

“Thank you,” he said. “Thank you, thank you, thank you.”

“What was that?” I asked, raising my voice.

“Thank you sir!” he yelled.

I pulled out, wiped the still-leaking tip of my dick on his butt, and got to my feet. I rendered my verdict. “Yeah. You’ve trained this one pretty well.”

I had to wash up before I left. Daddy Tim followed me to the bathroom, grinning at me. “You always put on a good show,” he said. He wasn’t far wrong. I didn’t need any of that shouting stuff for my pleasure, but I knew it would excite the trainer. And keeping a hole excited is sometimes what it’s all about, especially when it’s being fucked by multiple men. “What’d you think?”

“He’s good,” I admitted. “Very good.”

“You’ll come back again for him another round?”

“Anytime,” I promised, as I finished washing off my dick and hands. “You know you can count on your buddy Mark.”

“Mike,” he corrected, leaving me once again to wonder why he’d picked a doofy alias for me to begin with.

It wasn’t until I got home and had been relaxing for an hour that I realized when I’d dressed again in the dark, that I’d accidentally come home wearing someone else’s sock. Ah well. A small price to pay for a hot piece of muscle ass.