How To Have Gay Sex Without Embarrassing Yourself

October 1, 2015 — 16 Comments

Sometimes I wish I could forget my first time. He was my first boyfriend, the person who introduced me to sushi, and the handsome man to whom I chose to lose my gay virginity. I was more anxious and excited than nervous, almost hungry for it. By the time I finally came out at the age of 26, my sexual tension was wound so tight, it required all of my self-restraint not to instantly bend over and bark, “Get inside of me” from between my knees when we first discussed intimacy.

Resting on my back in his bed, I remember thinking, ‘Oh my God. This is happening. This is finally happening.’ And when it did, it felt right. It felt natural. I didn’t feel ashamed or dirty.

After we finished, I held his tender gaze with mine. It was beautiful. My heart continued to race as I regained control of my heavy breath. I still recall the thin layer of sweat that gleamed on his naked shoulder from the street light outside that shined through the closed slats of the blinds hanging from his bedroom window. It felt better than I ever imagined. I knew it was a moment I would never forget. Unfortunately, it would be remembered for the wrong reasons.

As he slowly withdrew, the romance was rudely interrupted by the obscene chattering of a whoopsie cushion under my hips, its rubber lips flapping together vigorously as air escaped from its inflated body. The longer it lasted, the wider my eyes grew as my face gradually collapsed into an expression of 24-karat horror. I didn’t understand. This vulgar, staccato gush of wind blasting from my posterior never happened in porn, so why was it happening in real life?

It happened because I was never learned how to be a bottom. My parents lacked the necessary experience to tell me to keep my sphincter tight on the dismount. During my closeted years, my straight peers were more focused on big titties than discussing anal sanitation. I could have learned about it on my own. The internet provides the information if you ask for it; however, I was too eager to just do it.

Don’t let your first bottoming experience be a bad experience. Before you dive into bed (or kitchen counter or backseat of a car or under the bleachers of a circus tent, whatever), it will benefit you to keep the following in mind:

Keep it clean – Nothing will repulse your prince of penis more than a filthy anus. Prepare your cave of love with an enema and keep it clean with sanitary wipes. Planning a rendezvous may not be romantic, but your partner will appreciate the effort.

Be comfortable – Some positions will feel more comfortable for you than others. Sideways. Cowboy. Spread eagle. Upside down. This is different for everybody. If it’s uncomfortable in one position, try another. Some people even prefer to be eased into it with their partner’s fingers first (for the record, I am not one of those people). Whatever you prefer, just by all means, relax. Just don’t relax when he pulls out!

Don’t go in dry – Ever had an Indian burn when you were a kid? We all did. Now imagine it on your butthole. I strongly recommend lube. NOTE: Crisco is not lube.

Take your time – You may be a bottom, but that doesn’t mean you can’t be in control. Taking it slow in the beginning will be the difference between having pleasurable sex and feeling like you ass is being split open by a jackhammer. Besides, dominant bottoms are hot.

Stay safe – As my grandmother told me just before I got my driver’s license, “Boy, I know what you’ll be doing Saturday night. You better wrap it up!” Don’t do anything you’ll regret later.

I have learned a lot about gay sex since my first time, but I’ll never forget my first lover. He proved he was a gentleman after my ass blew as a warning to nearby ships sailing through a fog. He spread a gentle smirk across his face, looked into my eyes, and said, “Nobody ever said gay sex was pretty.”

16 responses to How To Have Gay Sex Without Embarrassing Yourself

  1. 

    This Cary, was to the same time educational, informative and hilarious. It’s a great piece of blog post and I as well admire your first partner for taking it easy and relaxed.
    Sometimes the hottest things aren’t the nicest… what do you think women are going through their first time? 😉 It might be hot, it might be romantic, it might be loving and caring and everything – but hell… nobody tells you that afterwards the bed is going to look like a murder scene…? I think you’re doing it right. You remember it with humor. 😉

    Liked by 1 person

  2. 

    Imaging your 24-carat look of horror had me hiccuping trying not to laugh at my desk. I’ve learned so much today!

    Liked by 1 person

  3. 

    Soooo what you’re saying is that much like hetero sex, gay sex is equally awkward and embarassing at times. Got it.

    Thank you for the laugh and the info. On a semi-serious note: I’ve been told gay men get offended when a straight person asks about gay sex. Do you know why? Why be offended at such curiosity? Granted, for most of us, our sex lives are generally never discussed so I get that aspect, but I don’t see the point in getting offended.

    Liked by 2 people

  4. 

    Look at you, being funny AND informative. Seriously, though. Well done, you.

    Liked by 2 people

  5. 

    Wish someone had shown *me* this post back then. I’d like to add tht some materials when used as lubes actually help destroy the condoms, so go n buy lube don’t just use anything.

    Liked by 1 person

  6. 

    Dear Cary, I forgot how much I love you. LMAO

    Imagine the WTF look on my face as I woke up and sleepily checked my inbox only to see this as the subject line on the first email I came to. You, young man, made my day.

    Liked by 1 person

    • 

      First of all, I love that you called me “young.” May I please use this on any future resumes? Also, next time, can you use “stunningly attractive”? I would like to include this with the “young.” And when people don’t believe me, I can just show them your comment. And then they can eat a bag of dicks.

      Mmmmm….diiiicks…

      Liked by 1 person

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