The Vetaran

"Hey buddy," Jim Bowers said as he ushered me inside. I didn't always come over to his place. Sometimes the legendary veteran would swing by my condo for some no-strings fun before work, or after playing golf. I'd enjoying giving him a nice BJ - it was kind of my big challenge and thrill, getting used the girth and length of Big Jim's meat and getting off on our age gap. The latter was just as thrilling when Jim would have me kick back for his turn at reciprocating. 

We even snuck in a BJ in a parking lot once, but while the risk felt fun, it was, well, risky. 

I'd worried this would mess up things at work. Bowers wasn't my boss, but he held a senior position in the front office org chart, an advisor to my big boss. Yet the man was completely normal after our first hook up. It relaxed me for when he hit me up for a second time. Then another.

Sometimes it felt like a booty call, sometimes we grabbed a bite and a beer after sex. It was all good.

But today was different. Big Jim said he wanted to fuck me. 

He was looking incredible now, shirtless and showing off that mature muscle, dusted with silver hair.

"Hey Jim," I said, stepping in. We met for a quick kiss, which became not a quick one. I could tell the ex-pro was really worked up today, and despite my nervousness, I was, too. We laughed a little at how horny we were when I finally broke the connection and stepped back. 

"You look amazing," I said. 

He flexed a little. Best of all, I could see that heavy dick in his mesh shorts. Not hanging either but boned up into a hard ridge. The man was in heat.

"How much you work out?" I asked. It had been on my mind for a while. For a man his age, Bowers was very well preserved.

Big Jim didn't miss a beat. "A hell of a lot, Moneyball," he said with a smirk. He cocked his head back toward his bedroom. "Feel like getting down to it? Or you want a drink or something?"

My heart fluttered a little bit. "I'm horny as fuck," I replied. "But I won't lie: I'm a little scared."

"Scared? Why?" Jim asked. I realized he was sincere in his question. Like it hadn't occurred to him.

"For starters, I don't bottom much," I said, then nodded down to his crotch. "And then there's that beast you got between your legs."

That made Bowers smile. I probably wasn't the first to compliment his endowment and wouldn't be the last. But the ego boost was appreciated. "You seem to like it."

"Hell yeah I like," I said. "I love it," I added in admission. "But that's a lot of dick to take."

He chuckled, stepping up to me, and running his fingers along my cheek. "You're overthinking it, Ackerman. Let's just enjoy this."

Easy for him to say, I thought. But something about him was charming me. The weathered face, the sea blue eyes, the craggly voice. I was gonna go with it. "All right, lead the way," I hissed.

I peeled off my T-shirt and shorts as I stepped into his bedroom. I'd learned to go commando for these hookups and as I freed my meat, my dick firmed up quickly as Jim pulled down the sheets and then slid down his shorts. 

I saw one reason for that massive hardon. Bowers had a cock ring on, which made that dick firmer than normal. He saw where I was looking. "Hope you don't mind the ring, bud. Just gives a little more insurance at my age."

I crawled on the bed and showed how little I minded it. Scooting forward, I let Big Jim guide that hard meat to my mouth. 

"Yes...." he grunted as I sucked in a few inches, then choked down another. I was getting better at this. My face blushed as I sucked, my bare ass up for Jim's gaze. I wasn't used for being so bottomy, so open in servicing with a guy, but it was a fun new mode. Particularly as I smelled Bowers' clean soapy scent and could see the silvery crotch hair in front of me. 

He put his hands on his hips and let me do the work. The man loved a BJ. I mean, who doesn't? But Jim seemed to really crave oral sex. I half thought he'd change his mind today and let me get him off with my mouth. I'd cleaned myself out and prepped for anal, but a part of me wouldn't have been upset with a change of plans.

But I felt his hand on my head, nudging me back. 

"Lie back," he urged. 

I scrambled back, letting Big Jim see my naked body. The man got off on my youth, on the fact he had a 20-something stud in his bed. He'd told me as much, but his eyes confirmed it now as he stood next to the bed and pumped some lube into his hand, fisting that rock hard granddaddy meat. 

"I hope to god you don't think you're just gonna ram that thing up me," I said in a nervous joking tone.

He grinned and shook his head. "Relax, Ackerman, I know what I'm doing." He got on the bed, his core contracting as he shifted his weight forward. Our lips met for a second and I took a moment to feel up that mature brawn. It was still a head fuck that I was having sex with THE Jim Bowers. Even if he wasn't quite my main childhood idle or on my favorite team growing up, I used to watch watch him play all the time, and it felt like I was in the presence of a legend.

He leaned up and I took in that view of Bowers's strong shoulder muscle and thick arms. He gave a couple of soft kisses along my abs as he scooted down. "Lift 'em up, buddy," he urged.

I was nervous but I wanted this, I decided. It had been a solid year since I'd bottomed, but I was getting in the mood now. As I pulled back my legs, Big Jim was gonna get me all the way there. He leaned in and I felt his breath and his five o clock stubble before his tongue darted out to lick me. 

Here was a man of surprises, all right. Jim Bowers was really into eating ass. It tickled at first, and I fought to keep the tickling sensation from overwhelming me. It was just my body's defensiveness. It was half mental, but also the unfamiliarity of having my ass stimulated. But Jim's tongue pressed deeper in, and the feeling changed. Rawer, more overtly sexual. 

"God," I grunted. It was a mind fuck, too, looking down at this older man, almost 70, going to town on my hole. And me letting him. 

He took his time but I could tell he was horny now. After a minute or so he leaned up and let out a soft growl of approval. "Hot hole, Dave," he said, timing the pressing of his first finger perfectly. It was lubed, and I enjoyed the thickness of his digit entering me. He dug around some, worming my sphincter open more before diving in for another rim job. 

"You got nice and clean for me, buddy," he said with approval.

"Yeah," I replied, holding my legs back and letting him prepare me. Alternating rimming with more fingering. Pretty soon he was focused on the latter, two then three then two then three fingers, drizzling more lube at the connecting spot.

He looked down at me, horny. Maybe that cock was viagra-ed up or maybe the cock ring was doing all the work. But it was steel rigid. 

He pulled his hand back and lined up that heavy, hard meat. "You got this, man..." was all he said, before I felt that dull stinging of his penetration.

"Fuck!" I cried. Not in pain but more in fear. 

He held steady, an inch of that fat dick wedged in my ring. "You're tight as hell," he observed. "Just relax, Ackerman."

"I'm trying!" I laughed. 

Jim smiled. God he was so handsome and sexy. I didn't think I'd ever be into a guy pushing 70, but at that moment I knew I really was. He pulled back and fisted that big meat. I felt bad I was extra work to get in. But he leaned in and kissed me some. Sensual, tongue-heavy kissing while his fingers went back down to work my hole again. 

I was ready this time. He broke the kiss but didn't pull back entirely. Deftly he placed that dong at my hole and applied just the right amount of force. And like that I had three solid inches of Jim Bowers' fatness in me. 

I clenched my teeth and gripped his biceps in automatic response.

His eyes challenged mine. "You got this," he assured me. More confident than I was. More pressure was pushing that very wet, very lubed phallus into me. I was tight but also enjoying that stretching feeling. Maybe because Big Jim was going slow. 

He nodded at me, his face now serious, not very sexual and horny. "You feel SO fucking good on my dick buddy," he growled in a low voice. That gravely Bowers voice. "You gonna make your Granddad feel good?"

We'd tossed back the granddaddy term. For me it was an extension of "daddy" - a daddy with a few extra years. Mature like Jim. But now that term hit me in a pervy place. My bowels unclenched and welcomed all of that magnificent cock into me. 

"Yeah you are," Big Jim hissed. 

"God, Granddad..." I moaned, hesitant at first, trying it out. 

"I got ya, boy," he said, more aloud as he began his first thrust. Not hard, but a real fuck thrust into me. With Jim's size, it felt like a lot and was rapidly rearranging my previous assumptions - of being mostly top, of not being into grandpas. 

His hips swiveled slowly as I held his muscular body and welcomed him into me. I felt like we weren't just having sex. We were mating. I was being owned from the inside out. I didn't normally feel whorish with a guy, but Big Jim was pushing some button deep inside me. Physically and psychologically.

"Fuck me, Jim!" I said, more assertively now. "Fuck me, Granddad."

His lips curled up and he threw more force into his thrusts. I was ready for it now. Unbelievably I was enjoying this. It was intense as hell, like it could become uncomfortable at any moment, but my ass felt alive, and I felt alive beneath this man, who was fucking for his pleasure. The lube on his cock kept my guts from clenching down too hard on his pistoning shaft, or when I did they didn't have anything to grip onto. The man was fucking me unimpeded.

I looked into his wrinkled, weathered, handsome face. Imagining how many groupies he'd nailed over the years. How easy it must have been for him to get laid in his prime. How easy it was for him now.

I didn't think a hands-free cum was a possibility for me. Maybe technically it wasn't since Big Jim's soft belly fur and belly were rubbing against my rigid cock. But I started cumming hard. 

"Jim!" I exclaimed, feeling that immense pleasure rising up from deep within me. 

That excited him all right. He fucked me and fucked me hard. Fast even, eager to maximize the sensations on his mature cock. "Right behind ya, kid," he grunted. 

The idea he was gonna nut in me thrilled me and made another shot of cum push out of my cock. 

I love watching men cum and seeing Big Jim in full orgasm was incredible. His older muscle tensing up and his voice sounding older as he cried out. Then him relaxing in tired stillness on top of me for a second before he moved his head to give me a soft kiss and pushed up to relieve the brunt of his bulk on top of me. 

I felt that thickness retreat and plop out of me. I felt slutty and maybe not in a good way as Big Jim's cum ran out of my used hole. But in every other way I felt happy and satisfied. Especially seing the smile on the man's face as he rolled off and lay next to me, nudging my chin playfully. 

"You were a trooper, Moneyball," he said finally. 

"I don't know if I should have enjoyed that so much," I admitted.

"Why the hell not?" Big Jim challenged me.

"Long answer or short answer?" I replied.

"Let's start with the short."

"Maybe I'm a little kinkier than I realized."

Jim shrugged and leaned up, sitting back against one of the pillows. "Nothing wrong with that, fella."

I copied his move, but not before shaking out the cramps from my legs. My ass hole felt loose and wet but the new sitting position made it less exposed. "So the Granddad thing..." I didn't even know what I wanted to ask, but I knew I had to check in with Jim.

He chuckled. "Seems to get you going, buddy. It's a little weird, I guess," he added. "I mean, I have grandkids and all. But I figure this is something different altogether."

"It is," I assured him. I looked down at my body. Dick well sated, cum smeared on my belly and chest. "I'm a fricking mess."

Jim agreed. "Let's get you cleaned up, Moneyball." He slid out of bed and extended his hand to help me up. At that moment, despite being much younger I felt weaker from the sexual exhaustion. "If you have evening plans, that's cool, but I feel like I owe you a nice dinner for putting out like that."

I enjoyed this camaraderie and enjoyed the shower we shared together. A chance to soap up his mature body. A part of me worried if I should be seen in public extensively with Bowers, alone with him, but we did work together and I'm sure could come up with a reason if anyone saw us.

Then as Jim soaped me up from behind and pulled me into his sudsy wet body, that fat dong there, the one that had given me what felt like a second deflowering... I realized Big Jim was right. I was overthinking it.