One for the Road

It sucks being hundreds of miles away. More than that, it really sucks being in love with a man insisting on a no-strings situation. But Mr. Miles - Dan - was my best friend's dad and things were,  well, complicated.

I told myself I wasn't going to put my life on hold or sabotage my chance for a relationship. But when Dan sent me a text saying he was coming to Boston for business again and was thinking of tacking on an extra day to his trip, I knew I'd be skipping my Thursday class and taking the bus down.

The second I showed up I knew I'd made the right decision. Mr. Miles answered the door in just a towel, his 49-year-old dadbod looking incredible with just the right amount of hair and that thick muscular daddy bulk that showed the man had been putting time in at the gym lately.

"You're a sight for sore eyes, Jeff," he said as he ushered me in.

"I'll say the same," I replied, brushing my knuckles flirtily along his furry belly as I walked past him into the generic business hotel room. I took a look around and saw an open suitcase, a folded shirt laid out and a couple of Dan's items on the desk. Otherwise, the room looked neat and unlived in. I set down my backpack and turned around.

I watched my friend's dad walk in, a horny smile on his face and a hardon showing beneath the towel. Mr. Miles wasn't overly hung, but he had a nice thick tool, hard and symmetrical in shape with a proportioned rounded head. "You're looking amazing Dan," I added, knowing the man didn't like it when I called him Mr. Miles when it was just us.

He unknotted his towel and let it fall. There it was, that daddy body I still jerked off to regularly. Dan used to be self-conscious about his body with me, but he'd grown to embrace how I loved every bit of it. Even before he lost weight, but even more now, the man was just so fuckable. I was chubbed walking to the hotel but I was full-on hard now.

"Sex before dinner?" he asked.

"Fuck yeah," I hissed, pulling off my sweater and T-shirt and making quick work with my jeans while I kicked off my sneakers.

Mr. Miles seemed to get a kick out of my excitement as he grabbed the lube and went to pull the bed covers down before plopping down on the mattress. His hardon stood up from his hairy crotch and he reached down to tug at his balls playfully. "Fuck, you've bulked up, stud...."

I smiled, making a show of yanking down my briefs and letting my erection plop up. I was hung pretty well, more long than thick, and Mr. Miles seemed to be really into my endowment. Even when I was a scrawny high school senior, that desire made me feel like king of the roost.

"I've been trying to make sure my Freshman 15 is going to the right places," I boasted, taking wide steps toward the bed to make my hard dong sway for him. I'd been putting in a lot of time at the campus gym and eating as much protein as I could. I was glad the dividends were paying now.

"I'll say, Jeff," he hissed, naturally parting his legs as I crawled up on the bed to join him.

I could have fucked Mr. Miles right then and there, but I had waited eight long months for this chance, and I was going to make the best of it. We kissed, and I was surprised how much Dan responded to it, not just a lusty sex kiss, but something softer, more romantic, though just as needy. This was gonna fuck with my head for sure, but I went with it, savored it. I kissed Mr. Miles with every bit of romantic finesse I could muster as a still inexperienced 19 year old.

Then I kissed down his body. I think Dan was annoyed at first - his nipples aren't an erotic zone, even though I loved sucking them. But he warmed up as my tongue traced along his belly and around his the base of his prick. Soon laving his daddy balls, before I nudged his legs up.

I'd never actually rimmed Mr. Miles before but I'd seen it a lot in porn videos and was way curious to try it. Thankfully, the man went along with it, giving me access and urging me softly to eat him out. It was addictive, that furry daddy hole, and the more I licked the more I wanted it.

I don't know how long I ate Dan out but I felt a tap on my shoulder. "Buddy, you're killing me... you gotta fuck me."

I leaned up and wiped the spit off my chin as Dan handed me the lube.

"I know..." I said as I flipped the cap, repeating his instructions to me the first time I boned him. "Put a lot on."

Dan looked at me with an almost shy look. "Actually, Jeff, you can go easy on the stuff.... I've been practicing a little since the last time."

"Yeah?" I asked in surprise, though I took his word and put just a thin drizzle before spreading the lube all along my length with my fist.

"I bought a toy, about your size," he admitted with embarrassment.

I got into the saddle, nudging my prick at his pucker. "The real thing is even better, Mr. M," I teased taking the liberty of using my preferred name for him. And I pushed in.

I expected tightness, particularly after months apart. Maybe Dan was getting nailed by some other dude, though my instinct told me he wasn't. But, fuck, it was like his hole was swallowing my stick right up.

"Shit, Jeff... fuck me buddy..." the man hissed, his strong arms reaching up to hold me and even pull me into him.

I went with it, not spearing the man, but pushing right up into his ass. "Oh fuck I love your ass, Dan," I growled, taking advantage of his horned up state to start pumping him. I wanted to say I loved him, but I kept the energy on the fuck bud side.

It helped that Mr. Miles was humping his hairy ass up a little to meet my strokes, signaling his need. We clenched at each other's bodies and I fucked harder, more excitedly. We traded simple sex talk between kisses, feeding off each other.

It was getting too much for me. "I know you want me to last longer, Dan," I said with exasperation. I was right on the cusp of my orgasmic plateau. Not there yet, but close.

The man nodded. "Stop for a second."

I did, feeling my chest heave with deep breaths. My prick actually twitched in its stationary position buried up Dan's guts.

"Fuck," I hissed. I wanted to cum, but I didn't at the same time. Not yet.

"Lube," he instructed simply, his own baritone voice hoarse with sexual need.

I gave him the bottle and watched him squirt some right onto his fat dick. He'd barely tossed the bottle aside and gripped his boner when he looked back up at me. "All right, stud... fuck me off."

Even with his instruction, my fuck thrusts caught him off guard. I went at that ass in rapid fire, deep strokes, making his eyes go wide.

"Oh fuck!" Dan cried. "Pound me, stud. Nail my fucking ass!"

I did and watched the man enter a toe-curling, face-reddening orgasm. Heavy shots of his daddy cum all over his body. It was beautiful and it was hot. My O wasn't simultaneous but I shot inside him in pretty short order. Sex with Mr. M had been hot before, even naughtier since I was doing it under my friend Zach's nose, but this time had all the previous times beat.

Mr. Miles seemed to think so, too. He was chuckling at how out of control we'd gotten. "Seems like you've learned a few moves at college, stud... that was fucking hot."

***

The sex was great but it was awesome just to spend quality time with Dan. The man took advantage of his expense account and took me to a really nice restaurant. "For the record, you're my client tonight," he winked.

When we got back to the hotel room we were both tired and just enjoyed some cuddle time in the bed, watching some TV and enjoying each other's bodies.

We may have gone to sleep early, but I woke up in the middle of the night to find Mr. Miles' strong body pressed back against mine. As I stirred I ran my hand along his flank and felt him hump against me. Oh fuck, he wanted sex again. I don't know if I had a boner in my sleep but I was certainly erect now.

I'd have to go to therapy one day to figure out my attraction to daddies. To figure out why I got such a rockhard bone with men like Mr. Miles. But right then, I knew in a gut way why this appealed to me. Here was the man who was a paternal figure in my life, the kind of man who could have been my protector. And here I was being his protector, running my fingers affectionately in soft caresses of his chest and stomach. Letting him know his Jeff was here for him. It was a fucked up psychodrama and probably in my head only but it turned me on like mad.

Particularly when I felt the man's strong hand reach back and grip my prick, guiding it between his buns and he shifted his body to line me up.

I don't need an invitation like that personally engraved. I fucked back into Mr. Miles. It was probably a little after midnight and we were both still in this sleepy state still - the kind of in-between state where your horniness is keeping you from the sleep your body wants. We clenched and rutted side by side, until I rolled him over for more leverage.

We hadn't fucked like this much, Dan face down, me mounting him, but I loved it. I loved the physicality of the sex and the thrill of topping this hot 49-year-old dad. I entered that weird headspace again, that psychodrama. Imagining Mr. Miles divorcing, imagining me taking this ass every single night, imagining becoming my friend Zach's daddy by fucking his father.

I came first, hard. I kissed the back of Dan's neck and rolled off, letting him flip over on his back to jerk off while I fingered his cummy, used hole. His orgasm wasn't as big as the earlier one, but he seemed to need that release. I was glad to give it to him.

We quickly rolled to different sides of the bed and went back to sleep.

An alarm jolted me awake. 5:30 was early as fuck, but Mr. M had a flight to catch and I had a morning bus back to my college town. I almost slept in until the last minute but I felt my dick bone up remembered our night time fuck. I'd have to store the memory of that for my JO sessions until my next time with Mr. Miles. If there would be a next time.

I slipped out of the bed. The shower was running, but the bathroom door was cracked open, maybe to give just enough light to wake me up.

I pressed on the door and saw him there. I'd never get sick of Dan's body. Full, meaty, just the right amount of hair, just the right amount of dad beef. I hadn't even planned to ask him for sex again, but there I was, standing feet away with my morning wood sticking right up.

The man just gave a slight smile and turned off the water. With a simple but lewd motion he raised his left leg and put it on the shelf of the shower-tub, revealing his meaty buns for me.

"One more for the road, stud?" he asked.

"Yeah," I croaked in my morning voice and stepped in to join him.