The Road Trip

June 2002

I met Casey at just before 9 AM. He was the last person we were picking up on our road trip to a comic book convention. In the front seat of the 4Runner were my friends Donny and Phil. The trip from where we picked Casey up on the north side of Milwaukee to Indianapolis was supposed to be just about 5 hours, so I'd probably get to know the guy.

At 9:45 we stopped for traveling drinks and snacks. By then, I knew Casey was 22, a student at UW-Milwaukee going for Veterinary Science. He lived with his older brother and his wife, was interested in Marvel comics and old Sad Sack strips. He wanted to get a vet practice in the small northern Wisconsin town he'd come from.

10:00 or so Donny and Phil had both started to give Casey some good-natured crap about how he still wasn't out to his brother and the guy's wife. His retort was that he would when he'd start to bottom. Donny said, "Joe'll show you how to bottom...he's the best bottom in the vehicle."

10:25 the razzing had stopped and we'd started talking in general about experiences, some general, some sexual, some very explicit.

11:00 Casey and I were talking one-on-one. "So, are you one of those serious...what...power bottoms?"

"No," I replied, "Not at all. I'm a bottom when I need to be a bottom. I top when I need to top. I keep myself open minded as much as I can." I smiled.

11:15. We'd finished some of our chat and were chilling out. Casey slid back in his seat, and I side-eyed his crotch. There was an impressive bulge. I noted it.

Five minutes to noon we started playing a road game, sort of a truth or dare thing. Phil, 32 years old, slender in a wiry, runners build had gotten the first 'sketchy' dare and was now sitting nude in the passenger seat. He'd also mouthed Donny for a few moments.

12:05 I got my first dangerous dare, which was to also undress. Casey paid a great deal of attention to what I was doing. I was solid at the time, a bit of extra padding in spots that would be worthwhile when I was climbing glaciers. He was watching pretty intently as my pants and underwear slipped off, my six and half inches most of the way to erect.

12:15 Phil was leaning over in Donny's lap, mouthing his reasonably thick six inches. I'd seen it before, done a bit with it before. Uncut, with loose skin surrounding a rock-solid core of power. I'd felt it in both of my holes, finished it off in both. Casey was glancing around the seat, leaning on the center console and watching the action, inadvertently leaning on my leg, periodically brushing up against my own cockhead.

I glanced at my watch at 12:20. Casey was out of his pants now, jacking a very nice amount of meat, close to seven and a half or so. Circumcised with a somewhat off-angle scar that had the effect of making him look slightly bent about two inches from the end. He was squeezing hard, wringing on himself.

12:25. Phil showed us that he had a fresh load in his mouth, with no corresponding traffic accident. He flipped it around with his tongue before swallowing. "That's how you do it." He said, "OK Joe, Truth or Dare?"

12:25 plus a few seconds, I had answered for Dare. "Have Casey fuck you back there."

"Kinda cramped dude." I answered. His guarantee it could be done was little reassurance.

12:27, Casey's lubricated knob pressed at my ring as I knelt on the back seat. I felt the heat of him on his crown, clearly wanting this. I was ready for him, so I bore down and felt the first part of his head enter. I bore down lightly to let him slip in further. A small push and a pop, then the head was inside.

"You sure you're not a hundred percent bottom?" He asked as, less than a minute later, three more inches of him rolled inside me with little difficulty.

I chuckled, "I just prepare, you know? Now let's get to this, alright?" I pushed myself backwards on him, feeling another couple inches come inside.

12:30 I checked my watch. There wasn't much time. I slammed back on him for every time he started forward, feeling the stubble of his groin against my asscheeks. "Fuck, man...I'm gonna cum pretty quick." He muttered between his teeth, his hands on my hips, pulling me back as hard as I was pushing.

12:33. "FUCK! FUCK ME! I'm gonna cum FUCK!" I felt him slam inside me and an alternate pulsing/deflating against my rectum.

12:34, He slid out of me, a wet line from his head flopping down along my perineum, hitting my balls on the way past. "Don't sit on my upholstery!" Donny said as I grabbed a handy beach towel behind the seat.

"Fuck man, that was amazing. We should do that again later." Casey gasped.

I smiled, "Oh, We will."

Phil glanced back at me, "So?"

"Near as I can figure he came at 12:33. We met at 8:54 this morning. That's 3 hours, 39 minutes, right?" I said, checking my math.

Phil just hissed between his teeth, "Fuck you. If we hadn't fucked around this morning, you would've taken longer."

"What are you guys talking about?" Casey asked, wiping himself with a napkin from the Kwik Trip we'd stopped at.

I replied to Phil, "That's $210 bucks dude. I'll expect payment at the Con." I then looked at Casey and said, "We had a bet based on something Phil had said. He said you were a horndog, and I said if that's the case, I'd have you fucking me within four hours. Donny said it would take longer. So for every minute before four hours, they owed me $10. For every minute over four, I owed them $10."

Casey looked at me somewhat concerned, "You mean...you weren't into it?" He was sort of dejected looking.

I turned my ass back towards him, "Hell, you can fuck me all the way to Indy...I loved it."