I often get requests from guys beginning "I'm straight, I've never been with a guy before, and I want to try it out with you."
No way! If you're straight, why would you even want to be with a guy? And if you're bi, gay, on the downlow, or "not into labels," shouldn't your first time be with just one guy, not a group?
They often counter with: "Ok, then, can I try it out with you?"
No way! Get yourself a boyfriend, not some random hookup. What if we don't find each other attractive?
But I agreed to a guy who just went by the initials CJ, mainly because he was so skittish and had so many requirements, I took it as a challenge.
1. "How do I know you're not a cop?"
What would the crime be? Same-sex activity is legal in this state.
2. "How do I know you're disease free?"
How do I know you are?
Why, what do you think will happen?
"You'll tell someone about me, and he'll know who I am."
Right, I know all your friends.
4. "I don't want you to know where I'm from."
Same town as me, right?
"No, I live far away. I could never do anything in the town where I live. Someone might find out."
5. "I don't want you to know where I work."
Why? Do you have a homophobic boss that will fire you for being gay?
"No, I'm afraid you will come to my job and try to talk to me."
6. "Can I come late at night, so there's no one on the street? They might see me."
Yes, the "I'm here for a hookup." sign blazing on your chest might clue in the passersby.
7. "I don't want to do anything that I don't want to do."
He sent me three pictures of him with his face cut out, standing next to other people. Their faces were still visible.
Thanks, that is so helpful.
By this point, I was pretty sure that CJ was a time traveler from the 1950s. Who was so skittish about being gay in this day and age?
First meeting: a no-show. "Sorry, a friend dropped by, and I couldn't get away."
Second meeting: a no-show: "Sorry, there was somebody on the street, so I was afraid to come in."
Usually you just get two chances, but he kept emailing me: "I really want to do this." So I agreed.
Third meeting: He showed up an hour late. "Sorry, I've been sitting in the car, waiting until there was no one around."
CJ was a twink, about as tall as me, very athletic, with a long face, small nose, and dark blond hair.
"Since you don't want to talk about biographical details, let's go right into the bedroom," I suggested.
We went into the bedroom and faced each other. "I'm really nervous," he said. "I've never done this before. I'm straight. Um...what do gay guys usually do?"
"We start with a kiss."
Soon we were making out vigorously on the bed.
CJ took his clothes off. He was very large beneath the belt, a Kielbasa+, and shaved.
Since when do straight guys shave their crotches?
He started to work on me. He didn't do a good job -- he sputtered and choked, and kept finding hairs. "Sorry -- I've never done that before -- I'm straight."
I started working on him. He was done almost immediately.
"Sorry...no one's every done that before. I'm straight."
Didn't he know that women were just as capable of oral sex as men? Or had he never been with anyone before, male or female?
"So, now what? Do we do anal?"
"If you've never done it before, how do you know you're into anal?"
"I've seen it in porn. And I've fantasized about it. One guy at work is huge -- I saw him in the john -- I fantasize about him all the time."
"So you watch gay porn and have fantasies about men topping you, but you're straight?"
"Yeah. You can't tell that I like guys, right? I mean, not by looking, like you can tell gays?"
"So many gay books!" he exclaimed. "Aren't you scared to buy them? What if you get arrested?"
"Gay books are legal," I said, shocked. "There are courses in gay literature and culture at most colleges. You can major in Gay Studies at the University."
He grinned. "You joking, right? Who would major in Gay Studies? They'd get beat up!"
"The Prairie isn't nearly as homophobic as you think. You have to take a few minor precautions, like not holding hands in public, but other than that, there's really no problem. I belong to a Gay Men's Group that meets at a different restaurant every month. We never even get stared at."
"A Gay Men's Group! In public and everything! I can't believe it!"
"Come to it sometime. I'll show you around."
"Do you use real names?"
"Yes. We even know each other's jobs."
"Sounds interesting...we'll see. I'll email you." He kissed me and left.
He hasn't made it to a meeting yet. But he keeps asking questions. He now knows about Stonewall, the Metropolitan Community Church, Lawrence v. Texas, and Gay Pride Festivals. It's a start.
See also: My First Grindr Hookup; The Teenager at the Bear Party; a Hookup from Hell on the Plains.