David and I Pick Up a Hitchhiker

Key West, Florida, August 2003

A common porn scenario is picking up a hot hitchhiker, who happens to be gay, gifted beneath the belt, and interested in you.

I've only done it once.

In West Hollywood you saw guys hitchhiking all the time, but they were usually hustlers.  I never picked anyone up.

In San Francisco and New York, I didn't have a car.

In Florida I was too apprehensive, until David visited.

You remember David, the effusive, ultra-horny former minister who got me into lots of scrapes in San Francisco.  In August 2003, he flew out for a five-day visit.

I hadn't seen him for six years.  He was a little more bald, a little more chunky, but still a beefy, bearded, bear, and as effervescent as ever.

I asked "What do you want to do while you're here?" expecting him to say Disney World, but he said "Let's go to Key West!"

I love Key West, 120 miles off the coast of Florida on a highway that crosses the ocean.  A compact, small town of 20,000, one of the most gay-friendly resorts in the world.  But it's a four-hour drive from Fort Lauderdale, a bit much for a weekend.

"I'll help out with the driving," David said.  "I always wanted to go there."

So we made a reservation at a gay B&B.  We started out at about noon on Friday, and planned to stay two nights and return early Sunday morning.

On the way south, you take an Interstate to Homestead, but then it's a surface road, Highway 1.  Sometimes we saw pedestrians along the road, and occasionally a hitchhiker.

In Key Largo, David called out, "Hey, that hitchiker is cute! Let's pick him up!"

"Are you kidding?  That's dangerous!"

Hitchhiking was a common means of getting around for the hippies and bohemians of the 1960s.  But it fell out of favor in the U.S. during the 1970s.

 "Hitchhikers are all psycho-killers!" TV commercials screamed.  "They will rape, strangle, and eat you!"

There have been actually only a few cases of hitchhikers robbing or killing the drivers who pick them up, but it was a common theme in pop culture.

"Don't be silly," David said.  "It's a great way to meet guys."

"Hustlers, you mean?"

"Regular guys.  Straight, but available.  90% of hitchhikers will let you go down on them in exchange for the ride."

"What about the other 10%?  Raging homophobes?"

"Come on -- you're on vacation.  Take a chance!."

"Ok, ok.  Next cute hitchhiker, we pick him up.  But we're not coming out to him, just driving him into Key West, that's all."

We rejected the next two hitchhikers as not cute enough, but the third, was a lean, muscular twink with his shirt off, standing outside the Dolphin Research Center in Marathon with a sign reading "Key West."  He didn't have a backpack.

"Is he ok?"  I asked David.

"Ok?  He's perfect!"

We slowed down, checked to make sure he was alone, then stopped.  I moved into the back seat, and the hitchhiker -- his name was Jesse -- got into the front seat next to David.

He was eighteen years old, a few inches shorter than me, tanned, with short brown hair, a smooth chest, lean, hard muscles, and big hands.


Jesse told us that grew up on a potato farm in Aroostook County, Maine, farther north than Montreal or Quebec City, about as far north as you could get in the United States.  When it came time to choose a college, he wanted to go as far south as possible, so he decided on  Florida International University in Miami.

They held a Freshman Orientation before classes started -- a week of tours, lectures, workshops, and "ice breakers."  Boring!   And he was anxious to get as far south as you could go.

So yesterday morning he got on a bus to Key West.  But he missed his transfer in Homestead, and he didn't want to wait three hours for the next bus, so he walked out onto Caribbean Boulevard and thumbed a ride south.

No, he didn't take off his shirt to attract drivers -- it was just a hot day.

The first guy who picked him up was driving all the way to Key West, but Jesse asked to be let off in Marathon.

"Why'd you stop in Marathon, with your destination so close?" I asked.

"Oh -- I wanted to swim with the dolphins.  You don't get many opportunities to do that, up in Maine."  He paused.  "So, um, are you guys gay?  It's ok if you are -- I'm not prejudiced.  I watch Will and Grace.   I just never met anybody gay before.  We don't have any in Maine."

"There are lots of gay people in Maine," I said. "I visited when I lived in New York."

"You lived in New York?  Awright!"  He turned and gave me a "high-five" gesture.  "That must have been cool."

"And I'm from San Francisco."  David said..

"Oh, I heard all about San Francisco!"  Jesse turned back to me. "Are you guys like,  lovers?"

"No, just friends,  But we've been in bed together.  Gay friends like to share each other's dates and boyfriends."

"You kidding? Wow --  I wish straight guys would do that!"  He paused.  "So, what's it like?  Cornholing, I mean.  Does it hurt?"

"A lot of gay men aren't into anal sex at all.  There's lots of other things to do.  Like oral sex -- I'm sure you've done that with girl."

"Oh, sure, lots of times," Jesse said with a bit of hesitation, turning his head toward the road.   "But I'll bet guys do it better, since they know what a guy likes."

"Do you have a place to stay in Key West?" David asked.

"Not really.  I figured I would just go as far south as I could, then turn around and go home."

Jesse was apparently a big flighty.

"Better not set out until tomorrow morning," David suggested.  Was he fondling Jesse's crotch in the front seat?  I couldn't tell.  "You can stay with us, if you want.  Of course, the B&B just has one bed, but you can camp out on the floor."

"That'd be great, guys! As long as you don't try anything, of course"

We did some sightseeing, took Jesse to the Southernmost Point in the United States, had dinner at a Cuban restaurant on Duval Street, pointed out various gay men, and then checked into our B&B.

As we laid blankets out on the floor for him, Jesse said "Ok, now I've been dying to see what you guys do in bed."

"Not much," David said.  "We're just friends, remember.  Now, if there was a hot guy in the bed with us..."

Jesse blushed.  "Um..um...well, can't you just do a little demonstration?  Just so I know."



"Ok, but if we're going to be naked, you have to be naked, too."

We all undressed and lay on the bed, Jesse as far to the right as he could, his hands covering his crotch. David and I started to kiss.

"Holy cow!" Jesse exclaimed.  "I didn't know gay guys kissed!"

"Sure -- it's my favorite thing.  Don't you like it?"

"Yeah...um...I like it ok, I guess."

David moved down and started to work on me.  Jesse's eyes widened, and he started to squirm.  He moved his hands away from his crotch.  He was rather small, ruddy, and uncut.

I leaned over and pulled him close.

"Just to see what it's like?"  he said.  Then we were kissing.

In the morning we took Jesse to the Greyhound Station to get on his bus back to Miami.

"See?"  David said.  "Jesse turned out to be a nice guy, and super-hot."

We stopped for another hitchhiker on the way back to Fort Lauderdale.  Nothing happened.

See also: Waking up to a Straight Boy in My Bed; My 12 Porn Movie Hookups; and The High School Bodybuilder.