Exploring Anal Play for the First Time As a Bottom
A practical, human guide to prostate massage, strap-on play, and preparation
So. You’ve decided to explore anal play.
Maybe that looks like prostate massage, strap-on play, or another form of anal play with a professional. Maybe you don’t have perfect language yet — just a clear sense that this is something you want to experience properly, with someone who knows how to guide it well.
You did the smart thing and researched instead of winging it. That already puts you ahead of the curve.
This guide is here to do a few things:
clear up common myths about anal play
help you prepare physically and mentally
set realistic expectations for your first experience
It may feel awkward in places. You may (and should) laugh. That’s normal.
Anal Play Has Nothing to Do With Sexual Orientation
Let’s get this out of the way early.
Enjoying anal play does not define your sexual orientation.
People of all identities — straight, gay, queer, non-binary — may enjoy anal play, or not enjoy it at all. Liking certain sensations simply means your body responds to them.
Toys and techniques don’t belong to one group of people. Butt plugs, strap-ons, prostate massage, and anal toys are tools — not identity markers.
Releasing that mental baggage makes the physical experience easier.
How to Choose the Right Professional for Anal Play
If you’re looking for prostate massage, strap-on play, or anal play with a provider, you’ll notice different styles of work.
Some professionals approach anal play within a traditional dominatrix framework, with specific boundaries around intimacy and touch. Others — fetish providers or specialized escorts — offer experiences that are more sensual and body-focused.
Neither approach is “better.” What matters is fit.
Read websites carefully. Pay attention to:
how a provider talks about boundaries
whether they emphasize structure, care, and pacing
how they describe first-time experiences
Respect screening policies and communication guidelines. This isn’t about jumping through hoops — it’s about setting the tone for a safe, intentional experience.
Preparing for Anal Play: What You Actually Need to Do
Preparation matters.
If you’re planning anal play, cleanliness and comfort are essential — not because bodies are “dirty,” but because preparation supports ease, confidence, and enjoyment for everyone involved.
Ideally, you’ll prepare before arriving. If privacy is an issue, talk to your provider in advance and book enough time. Preparation time usually counts unless stated otherwise.
It’s also normal to be asked to shower before play begins, even if you’ve prepped.
Here is an excellent, straightforward guide that explains how to clean safely and effectively for anal play.
You’ll note there are two methods; for strap-on and beginner anal play, the quick method with an enema bulb will be just fine. The hose method isn’t always appropriate based on your living situations (apartment-dwellers may have significant issues with this), and the bulb is practical and economical.
Some people alter their diets for a few days prior, increasing their fiber and water intake. This is very helpful, as is eating light the day-of. Some people also take an Imodium after they’ve finished cleaning as an option.
When to Reschedule: Hemorrhoids and Anal Fissures
If you have:
inflamed hemorrhoids
an anal fissure or tear
Anal play is not advised.
This isn’t about toughness or pushing through. Anal play will not help these conditions heal. Take the time you need and reschedule when your body is ready.
What to Expect During Your First Anal Experience
Once things begin, your job is simple: breathe.
Slow breathing helps the pelvic floor relax, which is essential for anal play to feel good. Nervousness is normal. Excitement helps. Let yourself feel it.
You are always allowed to communicate:
if something feels off
if you need more time
if you need more lubrication
Anal play should not feel sharp or alarming. Communication improves everything.
Let go of performance expectations. Erections may come and go. Orgasms may or may not happen. Porn is not a guidebook.
Focus on sensation and curiosity rather than outcomes.
If You Don’t Love It Right Away
This is more common than people admit.
Sometimes the body needs time to learn new sensations. Sometimes something simply isn’t for you. Both outcomes are valid.
Curiosity does not obligate you to enjoy everything you try. You’re allowed to explore and decide.
If you’re intrigued but unsure, patience often makes a difference — whether alone, with a partner, or with a professional.
After Anal Play: What’s Normal
After prostate massage or anal play, you might notice:
stronger or longer-lasting sensations
a shorter recovery time before arousal returns
differences in ejaculation
Or you might not. Bodies vary.
Take time afterward. Toy removal should be slow and intentional. Minor messes occasionally happen even with good preparation. That’s anatomy, not failure. Shit literally sometimes does happen.
The Point of Exploration
The goal isn’t perfection.
If you leave feeling more aware of your body — whether you loved the experience or decided it wasn’t for you — that’s success.
There’s no rule that says your first experience defines everything that follows.
Explore with intention. Choose providers thoughtfully. Give yourself time.
And if you want guidance from someone who takes this work seriously, you know where to find me.
Erin
