Prostate Massager Experience from a Top's Perspective

At a Glance

• Who this is from: Gay rapper and performer Big Dipper, a GIDDI brand ambassador, writes about his first experience using a prostate massager as someone who identifies primarily as a top and had avoided anal play.
• The barrier he had to get past: Past bottoming experiences hadn’t worked for him, so he’d written off prostate massage entirely. This post covers what changed his mind and what the experience was actually like.
• What made it work: The TOMO’s shape, controllable come-hither motion, and adjustable vibration settings made it comfortable to use on his own terms. He could move it where he wanted and adjust intensity throughout — that control made all the difference.
• The takeaway for tops: Prostate pleasure doesn’t require being comfortable as a bottom during partnered sex. Solo exploration with the right toy, at your own pace, is a different experience entirely. His verdict: top approved.
• Who this applies to: Prostate stimulation isn’t orientation- or role-specific. Straight men and couples can benefit just as much — the anatomy is the same regardless of who’s in the room.

In this post we'll hear from GIDDI brand ambassador, Big Dipper. He will dive into his prostate massage experience and what makes TOMO the best prostate massager.

Hi, I'm Big Dipper — a gay rapper and performer living in Los Angeles. You can find me @bigdipperjelly on Instagram and Twitter or search "big dipper rapper" on YouTube to see my music videos. My music is fun, upbeat party music with a focus on celebrating all bodies and sexualities… but mostly my body and my sexuality lol.

On stage, I wear outrageous outfits: spandex jumpsuits, thongs, and sparkly harnesses, and I rap about sex, queer identity, and all around bedroom kink. In my life, I'm a little more subdued. You won't find me at the grocery store wearing a neon g-string and rhyming about how to take a dick.

That being said, there are parts of my personality that translate into my preferences in the bedroom. I like being in control, and though I have experience bottoming, I am way more comfortable as a top. I like the feeling that I'm the one "doing the fucking" not the one "getting fucked".

I've bottomed a few times and it didn't really work for me. That's why I've shied away from prostate massage and prostate massagers in the past. However, recently I've been very interested in exploring my bottom side and learning about the ways a prostate massage benefits your health.

I was introduced to the TOMO and asked to be a GIDDI brand ambassador by its founders. I loved the concept of it being an intimate health and wellness brand, and the sleek, professional aesthetic of the branding, but I had to try the product before I agreed to promote it, obviously.

So a few weeks ago, I decided it was time for me and my new TOMO to get to know one another. I grabbed the bottle of Ride Bodyworxx Lube, and convinced myself everything would be okay lol. Let me tell you it was way more than okay. Honestly, I was very pleasantly surprised.

Up until this point, I just thought my body wasn't really set up to receive anything…if you know what I mean. The TOMO was the perfect shape and fit in comfortably, and almost immediately I began to feel the positive effects. And I loved that I could control it. I could move it where I wanted, turn the "come hither" motion on and off, and change the vibration settings. It's perfect.

If you're a top like me, my recommendation is try the TOMO and don't be scared. But keep in mind that prostate pleasure isn't just for gay men. Straight men and couples can also enjoy the benefits of prostate massage!

It was a really special moment to have with myself, to reveal another layer of my sexuality. And I look forward to sharing the TOMO with a partner. It's totally top approved.