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Casey Boy’s Drawing Of The Infamous Shirley MacLaine + Motorcycle Sex Dream

Our apologies to the very talented Shirley MacLaine for the story that we’re about to tell.  Usually on April 24th, Preston announces Shirley MacLaine’s birthday during Preston & Steve’s Entertainment…

Shirley MacLaine CENSORED

Our apologies to the very talented Shirley MacLaine for the story that we're about to tell. 

Usually on April 24th, Preston announces Shirley MacLaine's birthday during Preston & Steve's Entertainment News segment. The show discusses a few of her accomplishments and their favorite movies. Then, without fail, someone brings up the time Casey had a sex dream about her.

This year, we completely skipped the career part and went right into talking about the dream. That's what lead us here and maybe lead you to coming here. As we promised on the air, the photos are below. But first, take a walk down memory lane to refresh yourself on how this story came to be:

The exact date of this dream is up for debate. The earliest reference to the dream on record is June 2011. Casey Boy was taking a medication to help him quit smoking, and it gave him wild dreams. We'll let him pick up the story from there:

I don’t know how long ago it was…but the memory is still so fresh in my mind. I am talking about my sex dream about Shirley MacLaine. This wasn’t just any old sex dream…this was the most vivid and weird sex dream, and it didn’t last very long. It all happened on the back of a motorcycle. Shirley was driving the motorcycle, and I was riding bitch. Obviously, we were both naked. My dream started with me doing things from behind while she drove the motorcycle on West Chester Pike and ended as she was turning onto Lawrence Road in Broomall, PA. That’s when the dream ended. This was well over 10 years ago…and I will never forget it. Happy Birthday Shirley!

Not only did we get the story, it came with an illustration as well to help us visual the aforementioned "things". Sixty-eight years of acting, and Ms. MacLaine will also be synonymous with cruising braless through Delco!

Thank you, Casey Boy, for sharing this vivid memory and detailed drawing. Oh, and another thank you to the fan art this story inspired.

Pencil drawing of Casey Boy's Shirley MacLaine sex dream

Tattoo artist & friend of the show, Bob Dodge, created a beautiful interpretation of Casey Boy's Shirley MacLaine sex dream

fan art of Casey Boy's Shirley MacLaine sex dream

Unknown fan art submitted after Casey's original telling of the story.

The Preston & Steve Show has been a staple of Philadelphia’s morning radio since 1998. Hosts Preston Elliot and Steve Morrison lead the show alongside Casey Boy Foster, Marisa Magnatta, and Ryan Shuttleworth, bringing laughs, interviews, and unforgettable moments to weekday mornings from 6:00 to 10:30am (give or take). Listen live on 93.3 WMMR or the MMR App, watch the daily YouTube livestream, and subscribe to The Preston & Steve Show’s full-show podcast to catch every moment.