Tales from the Tail — Poking Holes in the Gloryhole Fantasy

Dr. Evan Goldstein
4 min readDec 8, 2020

Client’s Tale.

I dreamt every night over the past week of experiencing a glory hole. I guess it’s been on my mind since this is one of the recommendations for a safer COVID-19 sexual experience. I’ve been seeing states and the media pushing it out a lot. What’s weird (and honestly quite disrespectful) is that any time it’s brought up, it’s focused on hetero sexual practices, especially women, which leaves us gays to once again fend for ourselves. Fortunately, I wasn’t about to let this get in my way.

I tend to see my dreams as some sort of parallel for what happens in real life and having never experienced a glory hole before, I thought — now’s as good a time as ever to live out my dreams. So I conjured up enough confidence to strut down to the local glory spot. The door was being held open by a big daddy type who eyed me up and down. I made my way past the usual fare to the back room and holed myself up into a dark old cubby. At first, I honestly couldn’t tell if there was a mouth or an ass on the other side, but I really didn’t care — my pants were down around my ankles faster than you can say “blow me”. My cock was already throbbing (I had been leaking precum all day due to a combination of mental ecstasy and a slight bit of nerves from the anticipation) as I slowly inserted myself into him, realizing almost immediately that it was in fact a mouth. Warm and wet, it was just like my dreams.

But at that exact moment, it all started to change. That feeling of excitement and desire almost instantly turned into disgust. I felt dirty and full of guilt. Then, my hard cock became totally limp. I was completely defeated. I quickly pulled up my jockstrap and pants and darted the fuck out of there. I never looked back as tears started streaming down my face as I made my way home. Back in my small apartment, all alone, I wept. But why? What was the difference between my dreams and this real life experience?

In the days that followed, I continued to experience high levels of anxiety over, so much so that I decided to get a full panel of STD screenings just to prove to myself that I was fine. Everything came back negative, though I shouldn’t have been surprised since I only had my dick sucked for about five seconds. But still, the image I had concocted in my nightly dreams were nothing like reality. Maybe, sometimes, sexual fantasies are only that — a fantasy…

My Discussion.

This topic is a departure from my usual Tales from the Tail, but I felt it was super important to discuss how our sexual desires and/or dreams affect or influence our reality. I’m confident we have all been in situations before where we have walked away feeling “dirty” or ashamed. Butt I am here to tell you it’s okay. It’s because of these life experiences that we figure out our preferences. It’s like when we’re kids and our parents tell us: how do you know you don’t like something if you haven’t even tried it? The key is to learn from everything we do and everyone we encounter. Don’t think of it as a negative experience — think of it as a learned experience.

Our dreams are powerful experiences and most are very hard to replicate (and some shouldn’t be replicated at all). But sometimes it’s good to try. As in the client above, now he knows that the randomness of the situation, location, and hole was simply too much for him to process or absorb all at once. Perhaps starting slower (like going with a FWB so you know who’s on the other side of the hole or setting up a DIY gloryhole at home) would have allowed him to explore his fantasy in a more controlled environment and given him the flexibility to take things at his own pace. It’s easy enough to build one or set one up on your home or apartment, recreating this dream-like fantasy in real life.

Glory holes are hot, but why they’re hot varies person-to-person. For some, it’s the total anonymity of who is on the other side. For others, it’s just not being able to see the other person. If it’s the randomness of the person on the other side of the hole, I recommend taking precautions, like PrEP, TaSP, and prophylactic antibiotics or antivirals.

I’ll finish with another cheesy idiom — if at first you don’t succeed, try, try again. I think it’s important to analyze your preconceived notions and then the actual play-by-play to understand what would or could help improve your experience. Desire is fascinating to explore, especially when it’s outside of what our generally heteronormative society deems “conventional”. As long as it’s consensual and safe, who the fuck cares what others think? The first person you need to get on board before turning a sexual desire into a reality is yourself. Then, your partner(s) need to get on board. A hole is a hole is hole is not always true. Each person provides a different experience, some positive and some negative. It’s what we do with them that matters. And whatever that is, shame has no place in the bedroom (or anywhere else).

Don’t forget to stay in touch on Instagram: me and Bespoke Surgical.

--

--