Prostate Massage

Come Curious, Leave Quivering & Shaking.

You’ve heard whispers. Maybe watched a clip or two. Maybe you’ve even tried it… tentatively, nervously, with a finger and a hope.

But let’s be honest: you didn’t really know what you were doing, did you?

That’s okay. You’re not alone.

Most men have no idea how much pleasure can be derived from their own holes. And frankly? Most of the people trying to show them aren’t exactly qualified.

Lucky for you, I am.

I’m Erin Black, professional fetishist, expert tease, and the woman your prostate has been waiting for. I offer exclusive, high-end prostate massage sessions in Chicago for men who are ready to discover what happens when skilled hands, anatomical knowledge, and a very dominant personality all come together for one unforgettable experience.

This isn’t “just a finger.”

This is a full-bodied, mind-wiping, breath-stealing reset button for your entire nervous system.

And yes, I’ll enjoy every second of watching you unravel.

So… What’s the Big Deal About Prostate Massage?

Let’s start your lesson.

The prostate, aka the male G-spot, the P-spot, the pleasure button behind your balls, is a small gland tucked just inside your asshole.

When it’s massaged correctly (and I mean correctly), it will make your cock leak like it’s never leaked before, can trigger full-body orgasms, hands-free release, and sensations that make your toes curl and your eyes roll back.

With me giving you a prostate massage, you’re not just getting poked and prodded. You’re getting stretched, teased, edged, and trained, and drained. You’ll feel things that make your knees weak and your brain melt.

And you’ll love every second of it.

Prostate Massage FAQ

What you should know about booking a prostate massage with me.

How do I prepare for a prostate massage?

The most important thing in regards to preparing for any anally-focused session, including strap-on play, is cleanliness. I've got a whole guide here. Read it, then read it again.

If you come unprepared you will be asked to leave and will not be issued a refund. 

Who do you offer prostate massage to?

Anyone with a prostate. This includes cis men and trans women.

Normally though, I session with men ranging from age 25-55 who want to explore this part of their sexuality and understand anal pleasure more thoroughly. 

What does prostate massage feel like?

I've heard from past recipients that it feels like their whole body is lit up and glowing. Someone once referred to feeling like his skin was sparkling, like one of the vampires in Twilight. 

Prostate massage is a different sensation from what you're use to, if you're just used to having your cock stimulated.

When you're in my hands, prostate massage will more than likely feel world-changing. but one thing that you shouldn't feel is pain.

Will i be erect during a prostate massage?

It depends. For some folks, they stay hard the whole time and for others, they don't. The same muscles that keep your dick hard are also the same ones you have to relax in order to let me in there, so it shouldn't be surprising if you can't stay hard.

What's great about prostate massage is it truly is not about your dick. Its about learning how to receive different kinds of pleasure and stimulation that aren't cock-centric. This means prostate massage is perfect for those who have erectile dysfunction or premature ejaculation issues.

Will i orgasm solely from prostate massage?

Maybe? It honestly depends. You absolutely can, but that ability normally develops over time. 

You may even be able to experience an anal orgasm, which is something different all together. Whatever sensations you're feeling, I'll coach you through them and get you where you need to go.

I'm brand new to this. Do you have toys for beginners?

I have toys ranging in size from small and narrow to bigger than my forearm. 

The last thing I'm going to do is put something in your ass that you're not going to be able to take. We're here for a good time, not a trip to the emergency room! 

I've been doing this a really long time. Generally speaking you have to take 2 of my fingers before I'll even consider putting a toy in you, so make sure to book appropriately.

This is my first time. How long should I book?

For first-timers, I recommend at least 90 minutes, if not two hours. This gives us time to get comfortable and also helps you relax. 

Generally speaking I don't take sessions over 2 hours unless there's another activity involved (dinner, cocktails, etc), or you're booking a duo.

Are there other benefits of prostate massage?

Beyond the moaning, gasping, and soaking-the-sheets kind of pleasure, prostate massage actually has benefits too.

Imagine that—kink that’s good for you!

Some perks of getting worked over by my skilled fingers:

  • Improved blood flow and reduced pelvic tension
  • More intense, longer-lasting orgasms (you’re welcome)
  • Deeper connection with your body and pleasure
  • A sense of total surrender—and complete erotic reset

Basically? It’s kind-of like therapy. But way more fun.

What a Prostate Massage with Me Looks Like

Let’s be clear: I don’t do cookie-cutter anything.

Your prostate massage session is built just for you; your limits, your body, your fantasies.

We’ll talk before we start. You’ll tell me what you’ve tried, what you’re nervous about, and what turns you on. Then I’ll take all that information and craft an experience that hits all your buttons—including the ones you didn’t know you had.

A Typical Session Might Include:

  • A slow, sensual external and internal anal massage and warm-up to ease you in (literally)
  • Skilled, targeted internal massage focused on your prostate
  • Edging, milking, or hands-free orgasm training
  • Verbal dominance, breathwork, and guided surrender
  • Optional elements like blindfolds, restraints, or cock-and-ball play
  • Me watching you fall apart with a smile on my face
  • Every twitch, every second, every sigh controlled by me.

Is Prostate Massage for me?

You literally typed in “prostate massage in Chicago” or some permutation of that phrase and ended up here. 

Of course prostate massage is for you.

Are you prostate-curious, aching to be teased, or tired of fumbling around on your own? Then this is definitely for you.

It’s also for:

  • Submissive men who love being controlled and opened
  • Performance-anxious guys looking to reconnect with their bodies
  • Pleasure-seekers who want to go deeper— literally and emotionally
  • Seasoned prostate players who are ready for someone who actually knows what she’s doing

Whether this is your first time or your fortieth, I’ll meet you exactly where you are, and then take you further.

Why book a prostate massage with Erin Black?

Because I’m not guessing.

I’ve trained in anatomy, breath work, and somatic kink. I’ve spent years perfecting the rhythm and pressure that gets results.

I know when to be gentle, when to be relentless, and when to whisper “good boy” in your ear while your whole body convulses under my hands.

With Me, You Get:

  • Clean, professional, private, upscale play space
  • Meticulous care concerning hygiene and prep
  • A kink-aware, judgment-free environment
  • Sessions that are safe, sexy, fun, and seriously intense
  • A woman who loves watching men surrender to sensation

I’m not rushing through this. I’m savoring it.

And I want to watch as I make you melt down in my sling or on my table.

Book Your Prostate Massage

Erin Black has been Chicago’s premiere alternative, BBW, Tattooed, and Kinky escort since 2011. Erin specializes in Kinky GFE, sensual domination, chastity, smothering, gender-based play, BDSM, pegging, prostate play, strap-on play, and dominant, woman-led experiences.

Instagram Twitter Film Envelope Phone Amazon Gift
About
Sessions
Rates
Contact
Newsletter Signup

© 2025 Erin Black. Designed by Black Ash Consulting.

Erin Black has been Chicago’s premiere alternative, BBW, Tattooed, and Kinky escort since 2011. Erin specializes in Kinky GFE, sensual domination, chastity, smothering, gender-based play, BDSM, pegging, prostate play, strap-on play, and dominant, woman-led experiences.

Instagram Twitter Film Envelope Phone Amazon Gift
Newsletter Signup

© 2025 Erin Black. Designed by Black Ash Consulting.

Most folks simply hope for what they want.
Not you, though. You get what you want.

My Summer Availability:

5-9pm, Monday-Friday
11-9pm Saturday and Sunday
I do require 72hr+ notice for all bookings.

I occasionally have daytime availability during the week! If you’re a current friend, please reach out via text message or direct email.

If we have not met before, please fill out my booking form for consideration.

Newletter Sign-Up
Enter The Website

Newsletter
Sign Up