Strap-on & Pegging

Where Power Meets Pleasure—and You're Deliciously Caught in Between

You’ve been curious, haven’t you?

Maybe it’s a fantasy that’s lingered in the back of your mind, a secret desire you’ve been too shy to voice.

You crave it, don’t you?

The pressure. The stretch. The feeling of being taken from behind, firmly, slowly, completely, by a woman who isn’t asking permission. She’s telling you what you’re going to take… and exactly how long you’re going to take it.

Maybe you’ve dabbled. Maybe you’ve fumbled with a toy or tried it with a partner who was just as unsure as you were.
Or maybe this is the fantasy you’ve kept tucked away, behind passwords and blushes, waiting for the right person to make it real.

Well, lucky you. You’ve found her.

I’m Erin Black, a professional fetishist and Chicago’s unapologetic strap-on queen. I specialize in crafting sensual, filthy, body-and-soul experiences that leave you trembling, wide-eyed, and wondering why you waited so long to hand your ass over to a woman who knows how to fuck you like she means it.

When I put my cock on, it’s not just for show. It’s because I intend to ruin you—gently, beautifully, and thoroughly.

It’s time to stop wondering and start experiencing.

What is sensual strap-on play, anyway?

It’s penetration.

It’s role reversal.

It’s power exchange wrapped in lube and laced with pleasure.

Strap-on play (or pegging, if you like labels) is about giving up control. Not just physically, but energetically. It’s about opening up, both literally and emotionally, and discovering how damn hot surrender can be when it’s handled with skill and a wicked smile.

This isn’t about humiliation, unless you’re into that. In which case, I’ll make sure you know how much I’ll make you gape when I turn you into my personal cock sleeve.

Strap-on is all about permission. Guidance. Seduction. Pressure. Stretch. Release.

It’s about being seen, touched, filled, and fucked by someone who knows exactly how to handle your body and your nerves.

Whether you’re looking to explore your gender, do a little bit of role-reversal, get plowed into oblivion, or learn that you’re nothing but a power bottom with a hungry hole, I’ve got the skill, prowess and know-how that allows you to become that secret, wild, feral part of yourself that just needs their hole filled.

Strap-on FAQ

What you should know about booking a strap-on session with me.

How do I prepare for a strap-on session?

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 strap-on experiences to?

Literally anyone with a hole who wants to have it filled. This means women, trans men, and trans women should also come knock on my door (please).

Normally though, I session with professional men ranging from age 25-55 who want to explore this part of their sexuality and understand anal pleasure more thoroughly. Also keep in mind that strap-on sessions do not have to be anally focused, and we can concentrate on worship, oral training, and other configurations.

What does strap-on play feel like?

It honestly depends on your anatomy and where we’re focusing, so it’s going to vary from person to person. It’s immensely pleasurable for most people who experience it, both mentally and physically.

However, what you shouldn’t feel is pain. Strap-on play should never be painful or cause injury.

Will i be erect during a strap-on session?

Honestly, it depends. Some people with penises are incredibly hard during a strap-on experience, and others never get erect at all. There’s nothing wrong with either of these scenarios.

In fact, if you’ve had prostate cancer or have erectile dysfunction, there’s nothing to worry about. Strap-on play doesn’t revolve around having an erect penis; its about other parts of your body.

Will i orgasm solely from strap-on play?

You absolutely can! However, it can take some time in order for this to happen. The elusive hands-free orgasm doesn't come easily all the time, though.

Some of my clients experience orgasm solely from penetration, but this is an exception and not the rule. If your body isn’t used to orgasming solely from penetration, I wouldn’t expect this to happen right away.

What's the biggest/smallest toy you have?

Believe me, I can accommodate your size needs from the smallest to basically the largest toy you can think of, and then some. Don't worry about it. It'll be handled when you tell me your experience level.

What to expect during a Strap-on Session

We talk first. Always.

I want to know your limits, your fantasies, your comfort level, and your past experiences.

Then? You kneel, bend, or lay back. And I start getting you ready.

Your Experience May Include:

  • Tease and Denial: Building you up, only to leave you begging for more.
  • Sensory Play: Blindfolds, feathers, ice— heightening your senses by taking some away.
  • Prostate Massage: Warming you up is important. I only want to play with my toys; I’m not in the business of breaking them.
  • Edging: Bringing you to the brink, then pulling you back, again and again.
  • Verbal Control: Commanding your actions, your thoughts, your pleasure.

If you’re feeling adventurous, we can incorporate things like light bondage, roleplay, or another person. Generally, if you’re game, so am I.

Is sensual strap-on for me?

It doesn’t take a rocket scientist to know that if you’ve read this far, you’re definitely ready for me. 

Here’s a more specific list, though. A strap-on session with me is definitely for you if you fall into one or many of these groups:

The Curious: You’ve watched. You’ve read. You’ve maybe even tried. Now you’re ready for the real thing with someone who isn’t fumbling.

The Submissive: There’s nothing quite like being taken. Especially when you’re held down tightly, whispered to softly, and then slowly, relentlessly entered.

The Sensualist: You’re less about rough pounding, more about long, slow grind-until-you’re-drooling energy. (Trust me—I’m here for it.)

The Power Bottom in Training: You don’t just want to take it. You want to take it well. I’ll show you how.

The Gender Explorer: You want to explore power, submission, sensation, identity. Strap-on play can hold a lot of complexity, and I truly enjoy every part of it.

Why book a strap-on session with Erin Black?

Because I’m the real deal.

I’ve got the anatomy knowledge, the experience, the toy collection, and the hands to back it up. I don’t play just to play. I play because it turns me on. Because watching a man surrender—body, breath, and ego—is one of the hottest things in the world.

I don’t take a lot of clients. I don’t book five sessions a day.
If I choose you, it’s because I want to.
Because something about your desire, your curiosity, or your eagerness makes me want to put on my favorite strap and absolutely make you forget your own name.

I’ve also been told I have a toy collection that rivals The Sex Museum, so there’s also that.

Ready to Surrender?

If your heart is racing and your imagination is running wild, it’s time to take the next step.

Reach out, and let’s discuss how we can turn your fantasies into reality.

But be warned: once you’ve experienced strap-on play with me, vanilla will never taste the same again.

 
Book Your Strap-on Session

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.

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© 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.

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© 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.

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