I Had a Skype Hook Up with a Closeted Gay Trump Supporter

closeted republican

The worst part is that I didn’t shut off the camera after I found out.

By: Anonymous

I want to preface what I am going to share here with a confession. I’m one of those guys who likes to do the whole video thing because I’m super shy when it comes to meeting people, let alone sex. And so as an alternative, I’ve become somewhat addicted to Skype and Facetime hookups with guys that I meet on online. And since I discovered this site from the infamous Data Lounge, I figured why not share my shit here.

So this past February, I was on the hunt to find a guy who was interested in having a little live camera fun, if you know what I mean. My regular online F-Buds were offline and it was slim pickings on the haunts that I usually hit up for partners, like Craig’s List.

But then I got a message in response to a post I had placed on a site for guys looking to meet other guys with a focus on BDSM. Suddenly, things were starting to look up.

His called himself Trent*. We chatted for a bit through messages and discussed the different things we were into. He lived on the other side of the country and claimed to be nearing 35. While he was careful not to share too much personal information, he did mention that he was married to a woman and that he considered himself to be “slightly bi”.

Translation: I’m a closet case.

You meet all sorts of people online so it wasn’t a deal breaker. He wasn’t the first guy I had met who was living a secret life. In fact, I’d say that’s kind of the norm with video hookups.

Once we unlocked our profile pictures, I could see that he was nice looking; athletic build, some tats and semi-hairy. Going by his photos, I could also see he had a lumber-daddy quality about him, which I admit has always been a major turn on for me.

Some of the stuff he was into wasn’t really my thing. For example, he told told me he liked using toys and hinted that he sometimes he got turned on by doing video shows for groups. Not that I am a prude but I’ve never been into the multiple viewer thing. I shared with him that I was basically just into JO and some dirty talk. “Are we a good match for this?” I asked.

As we continued the messages back and forth, he tried to be charming and threw out a bunch of compliments. “Hey, you have an amazing body,” and “Come on man, you have to let me see you for just a minute.” It had been awhile since anyone had said those kinds of things to me and to keep it real, I was vulnerable because I had recently hit the big four-oh.

One of the reasons I like using Skype and Facetime (with people I know) for virtual hookups is because either party has the option of ending the session at any time. And depending upon the conduit of communication, you can also block the person if things get kind of creepy.

Look, I won’t BS you. I was caught up in the attention he was giving me in an obsessive way, similar to what you might find from an older guy getting fawned over by some young stud. Pathetic perhaps but I’m giving it to you straight.

And so over the course of the next few days, our messages continued until I finally gave him my Skype handle. I was reluctant to do this because I knew from experience that when a guy mentions the things he likes, there’s a good chance he will try to make it happen.  But as his charm offensive continued and my walls came down, I figured: What do you have to lose?

Just before we “went live”, he sent me an electronic message with a question.

“Would you be cool with just watching me stroke it as I play some music in the background?” he asked. “It’s up to you but it helps me to get going.”

I responded by letting him know that while music is all fine and good, I’d rather focus on the sights and sounds of the moment and could do without the special effects. He said he understood and that was the end of that.


It was early in the evening and when we turned our cameras on. As he adjusted his lens while seated in front of his computer, I could see he was wearing a pair of blue jeans and a black t-shirt. I couldn’t get a glimpse of his face and I am pretty sure the obscurity was by design, given the way he was positioning his camera. Here and there, he’d sip from a coffee cup.

I was on my futon in jeans and a hoodie and unlike my video chat partner, my entire face was in full view, thanks to the way I had my tablet resting on nearby table. Why hide it, you know?

I tried to talk with him for a bit with questions like how are you and where did you get that shirt? I don’t know, I guess I was just trying to soften the awkwardness of the moment. But Trent wasn’t looking for chit-chat.

“Strip down.”

His forceful request took me by surprise and at the same time, turned me on. I started off slowly but eventually stripped down to my underwear. As the compliments came in about my chest and abs, the pair of Andrew Christians eventually came off too. And I of courses mouthed by my own kind words to encourage him on.

Intermittently, he stand up and then sit down, with a stroke here and there for good measure.

But then he started to say what he wanted to do to me and produced a toy. Like I said before, I’m not a goody two-shoes but honestly, I really don’t get into props when I’m on video. I tried to direct the conversation elsewhere and asked him if I could see his mug.

“It really helps to get me going if I can check out the other person in full view. Can you take your clothes off and back up a bit so that I can see your face?”

trump supporter

Like a true showman, he started to slowly comply. The shirt went first and then the jeans. He wasn’t wearing any underwear. For a good 2 minutes, he yanked on his chain until it became fully aroused. Everything I saw was pretty hot and to his credit, the pictures he had sent me earlier matched what I was seeing on camera.

But his face was still out of view.

It took some cajoling but he eventually pushed on his desk, rolling it forward. I could see everything now. Trent had a well-kept beard, high cheekbones and short, brownish hair. He wasn’t model material or anything – there were lines and creases – but he was a very handsome guy.

And so as we did our thing and continued or commentary back and forth, something caught my eye. Hanging on the knob of a cabinet off to his side, I could see a red cap with white lettering. And honestly, I wish I hadn’t have seen it.

TRUMP: Make America Great Again

You would think that would have been a major buzzkill for me but it wasn’t. I guess I was so caught up in the moment that I purposely fooled myself into a place of denial. Maybe I’m not reading that right I thought to myself.

He eventually gave me the order to release for him and like an idiot, I complied. Our timing wasn’t exactly the same but he ended up doing the same a few minutes later. In between the wait time, I was starting to feel disgusted at what I was doing.

Before we closed our cameras, I remember him saying something like, “Hey, that was fun, wasn’t it?”

I couldn’t help myself anymore and so I just came right out and asked: “Hey, is that a Trump hat you have behind you?”

“You mean this?” he said as he reached for it. Like it was some kind of badge of honor, he put it on and added, “Yeah. What’s the problem?”

I didn’t have much of a response – “Just curious” – or something like that. He asked if I wanted to do it again in the future. “I’m not available next week because my wife is working from home. But after that we can,” he mentioned.

“Maybe, let’s see what happens,” I said, just before closing Skype.

To this day, I can’t shake the fact that I actually got off to someone I knew was a Trump supporter. It’s kind of like hooking up with a right wing evangelical. The whole time you are doing it, you know he hates himself and you.

Part of me wonders if he was one of those people you see on T.V. at Trump rallies. You know – the ones who unabashedly carry signs about making America great again and using dog whistle messages against minorities. Was he a bigot?

It just churns my stomach.

Since then, I’ve blocked him from Skype. I don’t regret engaging in video play but I’m deeply ashamed that I didn’t have the balls to turn the camera off as soon as I realized this guy was a birther loving, misogynistic supporter of the Donald.


*Name changed by request

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1 Comment

  1. “You know he hates himself and you”? Off, that took kinda hard. Ima muslim and I’m stuck in a dilemma of revealing or hiding my true self (have finally accepted that I’m gay after many years).

    Something I fear is that no one would take me as a boyfriend if they knew I’m a muslim since it is widely known that Islam and LBQT cannot be in harmony. Would you think so of a muslim too, that he hates himself and you? If so, could you cope with it?

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