Dear Gay Dude: Should Gay Guys Hook Up With Straight Dudes?

Dear Gay Dude,

As if being gay wasn’t gay enough, I’ve gotten myself into quite a hole (metaphorically, not sexually, I’m a total bottom). I’ve started the complicated procedure of talking to a “straight” guy. I’ve never dated, or fucked, a straight guy before and therefore I am totally lost here. What complicates the issue further is that said “straight” guy has fucked one of my gay friends before and thinks no one knows about it. My gay friend doesn’t care about this “straight” guy, who at the time was still dating a girl when he stuck his dick out of the closet and into my friend, and the subject is obviously not something I want to ask him about; so I come to you. He seems into me, talks to me throughout the day every day, and I know that all its takes is for him to get drunk one night and come over to fool around; but is it a good idea? What experience can you share about fucking “straight” guys?

-New at this

Hi New at this,

I feel like we’ve talked a lot about the interesting dynamic between straight and gay men. In fact this actually seems like a reversal of the question I answered a few weeks ago. I know I’ve made mention of my sexy past with straight dudes, but let me just break down each encounter for you.

Straight Boy # 1: The first straight guy I ever hooked up with happened to be the first boy I ever did anything with. I had been out of the closet for three days and wanted to smooch a boy so badly so I called up an old childhood friend who I figured might be into boys. I was basically like, “Hi. I’m gay now. Wanna come over and make out on my mom’s king-size bed while she’s at work?” Surprisingly, he said yes. Wow, I seriously can’t imagine doing this now, but never underestimate the power of a teenage boy’s libido. Anyway, he came over at, like, the most unsexy time—3:00 in the afternoon—and we went into my mom’s palatial palace of a room and started making out. I hadn’t seen him in awhile and I remembered him being sort of chubby, but when he showed up on my front door, he randomly was really ripped and in shape so I was super excited about that! After smooching on the bed for a bit, I started taking off his underwear when lo and behold, there was the biggest penis I had ever laid eyes on. Mind you it was the first penis I had ever seen, but even seven years later, it holds up as one of the biggest penises I’ve ever had to work with. You would think a porn star dick would be a teenage wet dream, but it was actually a nightmare. If you’ve never given a BJ, it’s best to start out small because they’re obviously easier to work with. But no, I got Dirk Diggler’s dick. I tried going down on it, but I kept gaging instantly. I was NOT ready for this. In the words of Destiny’s Child, I wasn’t ready for his jelly. His body was too dickilicous for me, baby. I basically gave up on it and then he jacked me off, went home, and got a girlfriend two weeks later. When you’re 17 and gay, hooking up with straight guys is really your only option. With that in mind, I don’t regret it.

Positive Straight Boy Experience: Yes.

Straight Boy # 2: This whole experience can be read about it here. Basically it was fun until it wasn’t, until it ruined friendships and became traumatizing. When hooking up with straight men, it’s important for you to realize how fragile they are. Be prepared for them to lash out at you and cut all ties because they aren’t ready to deal with same-sex intimacy.  If you have a strong friendship with someone, I would vote no on getting all gay with him. As soon as the orgasms fade, shit can get harsh real quick. And if you want to be his BF, you shouldn’t even think about smooching him. Chances are he will not come out of the closet and hold hands with you in the Castro.

Positive Straight Boy Experience: No.

Straight Boy # 3: I can’t get into specifics about this one because I’m still in contact with the dude and its sort of a big secret. But what I can say is that this was the most fascinating of the straight boy encounters. Out of the three, this guy was actually for real straight. He just got super turned on by being desired. Regardless of the gender, he enjoyed people wanting him.  The first time we hooked up, it was super porn fantasy and fun.  The second time, however, I stopped it halfway through because I was over it. He wouldn’t even kiss me and I felt so degraded. At 19, I’ll give you a blowjob because you’re hot and I’m horny and oh my god it’s freshman year. But at 22, the thought of giving someone who wasn’t even into me a blowjay, hurt my gay heart and soul. This put the nail in my straight boy coffin. After this, I said never no more to straight dudes. Even though it could be exciting, I felt like I was always getting screwed (in the bad way} in the end.

Positive Straight Boy Experience: No.

All of this being said, here’s my advice. Only hook up with this guy if you a} have no romantic BF feelings for him and b} can handle him getting weird and deleting you from his life. Really wonder what you want from this straight guy. If it’s just sex and a story to tell the grandkids, I would say go for it. But if you want something more, I would say don’t do it. It’s not worth getting emotionally attached to. Closeted gays are just too cray cray. Good luck in making your sexy decision!

Love,

Gay Dude

Ryan O'Connell

I'm a brat.

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