The first time I bottomed (i.e., was penetrated) for a man was an epic disaster. Even though I liked and trusted the guy, I was still nervous, drunk, and had never put anything in my rear end before — not even a finger while showering. I kept asking if I was pooping on him because I was convinced that I was. (For folks unfamiliar with bottoming, newbies often feel like they’re using the facilities since it’s their only reference for having something inside of their anus.) Clearly my unsexy jabber was taking him out of the mood, so much so that he eventually said, “Zach, if you shit, you shit, stop asking!”
After that experience, I was convinced anal pleasure wasn’t for me. While some folks love it, I clearly wasn’t one of them. A year or so later, I had a girlfriend who really wanted to peg me with a strap on. I told her about my failed bottoming experience, but she said I should try again. She explained that I had pretty much done every single thing wrong as a first-time bottom. I didn’t prep (douche), I had never tried to stimulate my prostate on my own, and I was clenching for dear life.
I agreed to give it another try, and my girlfriend then coached me on how to bottom; slowly we worked our way up to using a dildo. At first, however, it started with me sticking a single finger up my bum, then a couple, then her sticking a finger, then two, and so on. While she and I are no longer together, I can say with confidence that it had nothing to do with our sex life, which was fantastic.
Exploring anal and prostate pleasure has increased my sex life tenfold. It takes my orgasms to new earth-shattering heights. That’s why even when I top (i.e., the penetrator), I often put a vibrating toy in my rear end to enhance pleasure.
I was lucky that I had a girlfriend who encouraged me to retry anal stimulation. After my initial experience, I’m not sure that I would have ever tried again (or it may have taken me a few more years to give it another go, during which I would have missed out on numerous exciting sexual pleasures).
Still, years later, I’m learning new things about my body, but these new revelations don’t happen during sex — they happen when I masturbate. While masturbating, I can really focus on my own pleasure (and not worry about what my partner wants). I can take my time. I can push myself to do (and take) more.
Masturbating with butt and prostate toys has revolutionized my sex life. For example, one thing I’ve learned through the use of b-Vibe’s snug plug, (which actually contains weighted balls inside of the butt plug) is exactly where I like my prostate stimulated. The weighted balls shift inside the plug ever so slightly. So I had the butt plug inside of me while masturbating, and was rolling a little side-to-side, and was able to find out that I like stimulation actually further inside of me. This wasn’t the groundbreaking revelation. Learning that I like stimulation in a flattened U-shape curve was. I now use this knowledge when having sex with others. For example, I love receiving oral while also getting fingered. Now I can tell my partners exactly where and how to stimulate my rear end during oral.
At the end of the day, prostate play has enhanced my sex life, but I wouldn’t have been able to really enjoy prostate play, or even known what the hell I was doing if I didn’t masturbate with anal stimulation and sex toys. Now I’m a goddamn pro bottom —- all thanks to the hours I’ve spent exploring myself during masturbation.
Zachary Zane is a sex columnist and brand ambassador for b-Vibe.