The First Time is Never that Good

Adam Baran

The Fun Stuff February 02, 2020

In 1986, Sade released “Never as Good as the First Time,” the third single off her band’s critically acclaimed sophomore LP Promise. “What could equal the bliss, The thrill of the first kiss,” she sang on the opening verses, before the famed chorus comes in, “It’s never as good as the first time.” One late night on VH1 during my horny AF adolescence in the 1990s, I remember watching the video for the song, where Sade rides a black horse through a small Andalusian village, smiling, exhilarated, perhaps on her way to meet her lover. “Is that feeling, that smile, that excitement, what ‘the first time’ feels like?,” I remember wondering, hopefully? 

15 years later, I got my answer: HARD NOPE. 

My first time

My first time bottoming for a guy was so unmemorable I struggle to even recall the details. I was 21, Gregory was 35. We had dated for a few months, and at some point I said I wanted to bottom for him. I’d never done it, but had watched plenty of adult movies and knew that I wanted to take it really slow. One night after a movie, we went back to his place. I put a condom on his knob, lubed up my hole, and started to slide down on it. What followed was a bit of pleasure, a bit of pain, and a quick climax. It was hardly what my queen Sade had promised and we didn’t attempt it again. I was glad I finally tried it, but also disappointed that I didn’t love it as much as I hoped I would. The next 13 years or so, I had very few positive experiences bottoming, and stayed away from it in my regular play sessions. 

Shoving it in

Most of my friends share stories like this. Whether disastrous or dull, they tell of the surprise when the loss of butt virginity left them with only disappointment and discomfort. My friend Simi and his boyfriend were both college freshman virgins who knew nothing about lubricant or going slow. “We were in a small hotel room in Vancouver on our winter break,” Simi explained, “I was on my back with my legs up by his chest and he shoved it in. I screamed and kicked him out of me so hard that he hit the wall behind him.” 

I was on my back with my legs up by his chest and he shoved it in.

Danny didn’t take a willy at first, just his much older partners’ fingers. “I didn't completely hate it, but it wasn't hot for me,” he said. “It was kind of irritating.”

My friend Vincent was 22 when he met a guy on an app who invited him over. Vincent cleaned out first, and was ready for his first real gay bottoming experience. But his partner was clueless. “He just wanted me to suck him off for five minutes,” he said, “then once he was hard, he just started shoving it in my butt.” Vincent remembered at one point being in a lot of pain and telling him to stop because it felt like his hole had been sprained. 

It gets better

Films, books, poems, songs, and authority figures extol the magic of “the first time;” so that whether you’re straight, gay, bi or queer, the experience carries so much weight that disappointment or trauma is inevitable. Luckily, it does get better. Today Simi and Vincent and Danny regularly bottom with ease, and both remember happily–as I do–the first time that they really enjoyed being the receptive partner. It wasn’t until I was 33 that a late-night lover suggested we try it. Relaxed and very turned on, I finally experienced the type of lasting, intense pleasure that hooked me ever since. The advent of PrEP has also changed the way a lot of people approach intimacy. “Having new ways to protect yourself opened a whole new world to me,” Vincent shared–an experience with a boyfriend that still gets him hot.

Only get intimate with people when you want to sleep with them. That took me a little bit of time to figure out.

Advice for first timers

“Learn how to relax down there,” Simi offers, when I ask what advice he would give his younger self. “Try to have good communication on speed of entry so it happens slowly. Maybe sit on it first rather than having no control over how fast and hard it gets up there.” 

Vincent’s advice is more nutritious, “Eat a lot of greens and maybe take some Metamucil one to two days before. Let the person who's talking to you take the time to finger you and eat your hole–it really opens you up. A prostate massager is also amazing.” Danny offers another helpful tip, “Use a lot of lube, and go slowly. And only get intimate with people when you want to sleep with them. That took me a little bit of time to figure out.”

F&*! the first time

If you don’t have a good first experience, don’t worry. You’re certainly not the only person disappointed by these dismal close encounters of the first time. It’s really the first time that it feels good that matters. That’s an experience you’ll remember forever, and the one that will hopefully set you on the path to kicking butt at taking it in the butt. Think of all the lead ups, the lousy first time, the slightly less lousy second time, as practice until it clicks. It may take a few months (or 13 years), but if you just go slow, you’ll get it in the end.

About the author

Adam Baran is a Brooklyn-based filmmaker, writer, curator, nightlife mensch, and pleasure activist. He served as the NY Contributing Editor of celebrated queer publication BUTT Magazine for many years, wrote the first season of the hit gay webseries Hunting Season, and produced the upcoming Netflix documentary Circus of Books.

The views expressed in this article intend to highlight alternative studies and induce conversation. They are the views of the author and do not necessarily represent the views of Future Method, and are for informational purposes only, even if and to the extent that this article features the advice of physicians and medical practitioners. This article is not, nor is it intended to be, a substitute for professional medical advice, diagnosis, or treatment, and should never be relied upon for specific medical advice.


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