My Night With Hef

By Destiny Crystal Amber

I stepped into the Playboy Mansion expecting a wild party with exotic dancers and endless streams of champagne. Instead, I found myself sitting across from the one and only Hugh Hefner in his dumpy living room, sharing a Miller Lite while he reloaded a pistol. The place was like so rad..thus began my night with Hef. That’s Hugh. Hugh Hefner.

my night with Hef

Hef was dressed casually in cut-offs and a ratty old Mickey Mouse tank top, a far cry from the suave and sophisticated image he portrayed in public. We struck up a conversation, and I was surprised to find Hef to be a somewhat peculiar and eccentric person. We talked about everything from the size of his naked feet to the roaches that were everywhere in the room. The hours just flew by. I was living in a dream, and I just didn’t want to tryna wake up.

Hef’s Shooting Range

I was amped when Hef took me out to his backyard. He had set up a haphazard shooting range with like rusty tin cans perched on top of some concrete blocks. It was sick to see that Hef was a hella marksman-dude. He hit the cans every time. We spent an hour like old brah’s, shooting, chatting, and drinking lots of Miller beer. Hef even had me shoot an old dried-out GMO-free California Inland Empire corncob off the top of his head with an assault rifle set to full auto. I heard some neighbors yelling at him a couple of times to keep the noise down. He playfully yelled a few curse words back at them. I loved the way he was like so dope about life, as he staggered downrange to reset the tin cans, spilling his beer on his cutoffs.

Hef’s 4-Wheeler

After we had fired about 500 rounds, Hef suggested we take his noisy 4-wheeler out and go for a ride around the neighborhood. I was stoked and for sure down with that, and hopped on behind him. We cruised through the mansion-packed Beverly Hills and into WeHo while the fragrant SoCal beachfront winds coursed through our hair (well, my hair). I wore a floral print puff sleeve kimono cardigan loose cover up. Hef’s driving was sick as his muffler-less quad growled like the Indy 500. He slugged back his Miller Lites and blasted noisily past the various affluent landmarks and nearby star homes. It was so dope to be out on the open road with the gnarly Playboy mogul as he lived out his dream of being a regular guy.

We were hot and sweaty when we got back, but Hef refused my entreaties to take a bath or go for a dip in the California Grotto. As the night wore on, Hef’s bodily oddities became more and more legit. He like burped a lot and scratched himself without a second thought. Despite his apparent reluctance to maintain decorum, I found myself enjoying his company more and more with each passing moment. Here was a man with like absolutely no pretense, and I was like more than ready for what I expected to be the best part of my night with Hef.

Hef’s Bedroom

I have to admit I was like a little disappointed when I entered Hef’s famous bedroom. The room was pretty small, and the ceiling was falling down in spots. There was a single naked light bulb hanging from the ceiling. It was a heavy scene. There were two double beds covered with ancient ragged quilts done in the mid-California Mission Revival style. Neither bed looking very clean. Hef explained that we would each like have our own bed, as he didn’t believe in premarital sex or any kind of fooling around before marriage. It was a surprising statement coming from someone who had built his empire on the supposed allure of sexual fantasies. But Hef was unique; he was his own man, and he was still a lifelong bachelor and a virgin at the age of 66.

The beds were a key feature of Hefner’s Cali-styled bedroom, and his whole philosophy of romance was so down. He believed that keeping separate beds for potential sexual partners was an important aspect of maintaining independence and a healthy relationship. According to Hefner, the beds represented like everything that was American. He carefully outlined his Playboy Philosophy. One of the points was the freedom to do exactly as you pleased, both inside and outside the bedroom. So we each like stayed in our own beds all night as a demonstration of our sexual freedom.

I eagerly watched Hef undress before he got into his own bed. Instead of seeing boxers by Ralph Lauren or Calvin Klein, I watched Hef strip down to a pair of tattered, yellowed Fruit of the Loom briefs. “You’re like so lucky, Destiny,” I said to myself. “Not many girls have ever like had a chance to like do this – like experience like a whole night with Hef.”

As I lay in my own bed alone, I could hear Hef delicately farting between snores. I couldn’t help but feel a bit bewildered as I took in this heavy arrangement. But, since Hef hadn’t bathed after our sweat-soaked road trip, I was like a tiny bit thankful. My night with Hef was over far too quickly as I drifted off to sleep, with an odd, restless feeling of un-fulfillment.

The Morning After

Hef had promised to take me “out” to breakfast the next morning, and I waited patiently in the driveway while he dug around in his ripped cut-offs for an Arby’s coupon he was sure he had. He finally pulled a crumpled two-for-one coupon out, covered with pocket lint. He romantically insisted on walking the two miles to Arby’s, which was hella uncomfortable as I was like wearing heels. It was June gloom, and the marine layer was like for real. But, like being with Hef is what like counted.

Since we were using a coupon, I only had a choice between the Special Gigantic Breakfast Biscuit Duo with Jimmy Dean Sausage or the French Toast Cream Gravy Bowl with a side of Arby’s Pork Sticks. I would normally prefer the Deluxe Gluten-Free Croissant with Free-Range Natural Sea-Salt Plant-Based Country Bacon and Fresh Farm-to-Home California Avocado. But that like wasn’t an option with the coupon. Hef was so best-coast when he ordered it California-style: “I’ll do the French Toast and Pork Sticks.” No “please” or “thank you” or ‘I’ll have the…” You know, like the way we ordered back home.

Hef was stoked, sweet, and chivalrous. He used his senior discount to get me a small regular brewski, and then he like wrangled some free-range California Agave sweetener from the cashier (she greeted him like she knew him). He got a complimentary agua cup for himself, which he then proceeded to fill with Pepsi while furtively glancing around. We dined out on the Arby’s veranda, like right by the 405’s Wilshire exit. The gentle California shine glared off the parking lot of the adjacent Hyundai dealership. I mooned for real at my date as my ears were like flooded with the swinging California sound of the dealership’s thousands of colorful plastic flags flapping loudly in the gnarly Santa Ana winds.

Final Thoughts

Reflecting back on the night, I was struck by the contrast between Hef’s public image and his private self. He was like so much more than the caricature of a handsome, suave playboy mogul portrayed in the media. Rather, he was like a somewhat weird person who was a little smelly, with a unique perspective on life.

While the memories of that night have like faded with time, I’m like grateful for the opportunity to have spent my night with Hef at the Playboy Mansion. It was an amped-up experience that defied my expectations, and it was a dope time I will treasure for years to come.