The Hookup Contest, Part 2: Gabe's Date with the High School Boy

The Plains, January 2016

Remember the hookup contest Gabe and I had before Christmas?

We each chose someone for the other guy to try to hook up with on a dating app. I had to approach the 18-year old Bastian, a high school senior whose profile said explicitly "no older guys" and "no hookups -- dating and relationships only."

So I offered to set Bastian up on a date with Gabe, and tag along "for moral support."

All's fair in love and cruising.

The date was scheduled for December 20th, but Bastian cancelled. He said we could reschedule for after Christmas.

I figured that was the last we would hear of him-- younger guys wimp out all the time.  But he did text me a few days after Christmas, asking for the date to be scheduled on January 3rd, a Sunday night: dinner at a Mexican place, then the new Star Wars movie, The Force Awakens.

He didn't want his parents to know he was gay, so he arranged to spend the night at a friend's house.  We had to pick him up and drop him off there.

Bastian was slim, a little shorter than me, with sandy-blond hair, blue eyes, and sharp features.  He was wearing a sweater, no coat, and carrying a backpack.  "In case we spend the night," he said, sliding into the back seat next to Gabe.

Driving to the restaurant, I kept mostly quiet.  It was their date, after all.  Their conversation consisted of:

Gabe:  So you're a senior in high school. What are your college plans?

Bastian:  I applied to UCLA, Columbia, Florida State, and the University of Hawaii.  I'm going to wherever the guys are the hottest.  Boomer, you lived in California.  Were the guys big there?

Me:  Well...um...

Gabe:  What do you want to major in?

Bastian:  Art.  I want to start a fashion blog.  I'm really big into fashion.  Like, do you shave your pubic hair?

Gabe: [Embarrassed pause].  Um...no, I never tried that.

Bastian:  Oh, it's great!  It makes your penis look a lot bigger.  Here, have a look.  You too, Boomer." [A cell phone is shoved at me, showing Bastian nude, aroused, very big, with shaved pubes.]

The questions continued at the restaurant, including the sort of questions one doesn't ask in public in a small town on the Plains:

"Have you ever been topped by a really big one?"

"Do you know any guys with big ones?  I mean, really gigantic ones, like in porn?"

"Have you ever been with a black guy?  Do they have big ones?"

"Have you ever been rimmed?"

"Who's the youngest guy you ever let top you?"

"What does 'golden showers' mean?"

And, he was rubbing his leg against mine under the table!

When Bastian went to the bathroom, Gabe turned to me: "I thought this was a quiet, shy, conservative guy who wanted to date and get to know you.  Sounds like he won't even make it to the end of the movie!"

"I know, it's weird. He was brushing my leg under the table.  And I thought he didn't like older guys."

"Consider yourself lucky.  He was trying to grope me!"  Gabe laughed.  "Man, this aggressive bit is a big turn off.  We should take him home, so he can take a cold shower!"

"No, let's go to the movie, and see what happens.  Maybe he'll calm down.  Besides, I've been looking forward to seeing it for weeks."

At the movie, Bastian sat between us and held the popcorn, so we would reach in to get some and grab his hand instead.  Plus he used his free hand to brush against my thigh. He tried to grope me through my pants, but I pushed him away.

And he kept peppering us with comments.

"I bet Finn has a big one!"

"You think Finn and Poe are together?"

"Han Solo is one hot Daddy! I'd do him in a minute!"

I shushed him, but the comments continued.

Afterwards we walked out into the lobby and then into the mall parking lot.  Bastian linked arms with both of us.  "Hey, let's get frozen yogurt!" he said.

"Well, I'm a Vegan," Gabe said.  "They probably won't have anything I can eat."

"Ok...so then, back to your apartment?"

Gabe flashed a "no way!" look at me, and said "Well...I have a roommate, so I can't bring anyone home."

Bastian's grip on our arms tightened.  "Then let's go back to Boomer's place.  He can watch.  Or join in!  I've never been with two guys at once before!"

We got to the car.  Bastian climbed into the front seat, next to me.  Gabe climbed into the back.

"Ok, your place, right?"  he asked, putting his hand on my knee.

"I'm a little tired," I said.  "We'd better just take you home.  Or to your friend's house."

"But...you know, it's a date," he said in a small voice.

"We should just take you home," I repeated.

"I thought...but aren't we?"

Was the kid starting to cry?

I put my arm around him.  "What's wrong, Bastian?  You've been on dates before.  Sometimes things happen, sometimes they don't."

His shoulders were trembling.  "No, I haven't.  I've never been on a date before. Or had sex.   I never even met anybody gay before. Everybody at my school is straight.  Church, too.  I download porn and get hit on by Creepy Old Guys on that dating app, and that's it."

"So why all the questions about rimming and golden showers?"

"And the hands everywhere?" Gabe added.

He looked up teary-eyed.  "That's what gay guys do, isn't it?  I didn't want you to think I was just an ignorant kid..."

"That's not at all what gay guys do," I said.  "What they do is this."  I wrapped my arms around him and hugged Bastian, and kissed him on the cheek.  He didn't want to let go.

"Maybe I'm up for some frozen tofu, after all,"  Gabe said.  "Then we'll see what happens."

This is what happened:

Kielbasa, ok with kissing, mostly into anal.  But, with a 37 year age difference, I've now officially been with someone young enough to be my grandson.

See also: The Hookup Contest; a Boy for Valentine's Day