I will also be in town June 20-24 and have lots of experience with and passion for pegging!! I'd be happy to bring your fantasies to fruition.
xoxox
Harlowe

I absolutely love sensual strap-on sessions and have lots of toys for us to experiment with. You can take a look at my website and see in my photos and video just how much sensual strap-on play excites me.  

Harlowe Dahl abs Tori Valentine are also great touring providers who offer this, and I have quite a few other friends on my website that offer it as well.

 
Whoever you choose, have fun!

Erin Black, hands down. Or well, inside.

Seriously, I have sessioned with her in group scenes and she is the best I have ever seen.

And I have seen some women who are PHENOMENAL.

Its just not the act itself, its her incredible enjoyment of it.  Yes, she knows the techniques but its not that puts her over the top in my book.

I remember once when Betsy, I, and Erin were sessioning together - I think there is a review on here somewhere about it - and I slid my hand under her strap on cause I wanted to help her get off while she was going to booty pound town.

No need for my help, she was drenched and already almost there.

It was epic.

So, yes - Erin Black is a local Chicago treasure for sensual toy / strap play