Mutually Beneficial BFFs


Oct 07, 2015

“Hi beautiful. I think we could make each other very happy. Hope to hear from you,” he wrote. His profile presented a divorced, 67-year-old businessman with a net worth of $5 to10 million. When the message ended with the words “Love, Michelle” I figured he was French.

After exchanging pictures and speaking briefly over the phone, Michelle and I decided to meet for dinner at a quaint Beverly Hills bistro.

At first glance, one would find Michelle to be your average 67-year-old man, dressed to the nines in a classic white button-down shirt. Yet as I continued the full-body scan, I found myself doing a double take.

“I like your…skirt?” My eyes did not deceive me. Michelle was indeed wearing a denim skirt, fringed at the hem, Abercrombie & Fitch style circa early-2000s. I think I wore the same one to an ‘NSYNC concert as a teen. Maybe he was just old and didn’t know that style of clothing is made for girls? I thought to myself.

“Order whatever you’d like,” said Michelle as I browsed the upscale seafood restaurant’s menu.

I wasn’t starving, but I ordered a salad and grilled salmon to wrap up for later.

“Do you have plain salt-less tortilla chips?” Michelle asked the waitress.

“Um, we have bread?” she responded.

“Michelle, we could have gone for Mexican,” I whispered.

“No, no, bread will do.” He was a frail man, arthritically thin. When the bread arrived, he nibbled at the crust and called it a day.

“So, Michael, or is it Michelle?”

“What do you want me to be?”

“Whatever you want me to want you to be,” I retorted.

“Michelle it is then.” He proceeded to explain his cross-dressing fantasies which he’d harbored since childhood, when he was scolded for fooling around in his mother’s wardrobe. Over the past year, he had finally begun to revisit these fantasies and explore his feminine side.

I was intrigued. It’s often the same old vanilla with Sugar Daddies. As of late, my world had grown tired and bland, and Michelle introduced exciting potential.

“So you’re not French?” I asked.

“I’m Transylvanian. Just kidding. I’m Jewish. And Russian,” he attempted to joke.

I mustered a chuckle at his awkward sense of humor. “Hey, whatever you are, I think you’re great. Next time we can meet at my place, feel free to wear whatever you want!” It would be an entertaining experience, if nothing else.

“Seriously?” He seemed surprised at my willingness to enter into this strange breed of relationship.


“You won’t be spooked?”

“Spooked? Me? Never.” We planned a date for the following week.

Usually when visitors came to call, there were three to four minutes between the ring of the building’s buzzer and the knock on my apartment door. Michelle wore heels, so it took a bit longer. While waiting, I poured myself a glass of Merlot and played a few rounds of Candy Crush. After 10 minutes, I heard a knock.

Behold Michelle, in all her glory. Wig askew, she wore cherry-red lipstick, aqua-blue eye shadow and hot pink blush – all applied with a shaky grip. The jean skirt was back and better than ever, paired with a midriff-bearing tank top and leather jacket.

“Tada! How do I look?” Michelle asked with gusto.

“Very nice, Michelle,” I replied. I loved the new look, but had to wonder – would the rest of the world be so accepting?

“Does it turn you on?” She leaned in for a kiss.

“Well…” I stammered. Perhaps turned on was not the phrase I would have chosen. I was honored that Michelle felt comfortable showing her true self to me, and I was interested in getting to know her further. “Wine?” I answered, pouring her a glass.

“Please,” she responded. As I handed her the glass, I noticed her manicure efforts – a Jackson Pollock splattering of Wet ‘N Wild red.

“We should go for mani-pedis sometime,” I suggested.

“You mean I didn’t do a good job painting them myself?” She said with concern.

“I didn’t say that! Look, I don’t know where these claws of mine would be without the help of trained nail professionals,” I reassured her.

Michelle looked in the mirror and sighed. “I look like a clown,” she said.

“Don’t say that, Michelle. Beauty takes practice, like anything.” I slid my feet into a pair of 6-inch stilettos. “Here, I’ll teach you to walk in heels.” I stood tall and struck a pose.

“Wow,” said Michelle. “You’re the perfect woman. I’m a joke.” Tearing off her wig, she sunk to the floor, defeated.

“Enough with the whole Debbie Downer thing.” I joined her on the floor. Her self-tanner smeared off her legs, leaving orange stains on my rug. “When I’m 67 years old I don’t expect to impress anyone with my looks, in any capacity.”

“I should stop this. I’m throwing everything away tonight.” She started crying, and my comforting efforts were proving insufficient.

“That’s silly,” I said, wondering whether she’d let me keep the fake boobs she had brought over. It would be a shame to dispose of such fine wares.

I consider myself to be a liberal-minded person. I believe in freedom of self-expression for all. It was sad to think someone could go through life without ever becoming or understanding who she was and what makes her happy. Then again, wasn’t it a beautiful thing that Michelle started now as opposed to never?

Over the next several months, I helped Michelle learn the ropes of femininity. We took field trips to Rite-Aid and Sephora, stocking up on everything from Lip Smackers to Stila liners and Urban Decay potions. Sometimes we bought matching outfits at the mall. It was a teenybopper’s dream – and I was getting paid for it.

Lest we forget, Michelle was still my Sugar Daddy (Sugar Mommy?). We never became “intimate” in the traditional sense. Instead, we became MBBFF4Ls. Mutually beneficial best friends forever for life.