I met MegaDon on an online dating app that predominantly attracts older men and younger women. It works equally well for 40-something men and 20-something women as it did in my case – just add 20 years to both parties.

When he sent me his photo, he looked familiar, but I couldn’t place how or why. 68, 6′, the sexiest waves of white locks combed back but still fluffy and full, matching beard, wide smile with a body built by swimming, the sun, wine and a privileged life.

Once I recognized who he was, I was shocked and excited all at once. A local celebrity for sure and, within the family business, he was famous internationally for the industry-changing impacts his father and grandfather made. Truly his father was MegaDon – Don being a reference to the “Boss” in the Italian mob hierarchy. The family wasn’t mafia as far as I knew, but they ruled the land I now called home for many, many decades. With his father passed on (and my personal neglect for his older brother), this new sexy man who walked into my life took the naming rights. I’ll just call him Don for short.

Don first asked me to come to his house for drinks and dinner. After I explained my safety rule #1 – first dates always in public – he made us a reservation at a nearby Italian restaurant with a famed chef at the helm.

“I believe that the chances of us getting through drinks and a meal together, and then wanting to get together for even more is quite high!”

We were seated at a cozy crescent moon-shaped booth and sat at the 11 and 1 positions quite close for a first date. It was December and I wore black jeans, black boots and heavy but fitted grey sweater. He wore the mature man’s dressy casual – khaki slacks, button down long sleeve and V-neck sweater.

The sommelier addressed him properly by Mr. ‘Last Name’ and Don approved of his choice of a 2012 Grand Vin Pomerol for us to enjoy over our meal. There wasn’t a pause in our conversation all evening except when a random man heading toward the bathroom recognized him, stopped and said, “Hello ‘Don’ – great to see you. I enjoyed my recent visit to your ‘business.'” Don acknowledged him with a nod, thanked him and the man continued on.

We talked about the local industry, music, food, travel, family. He told his story quite modestly. Don was an alumnus of the local university which boasts a top tier program in our industry. Following, he was sent by his father abroad to learn more before returning home in the early 1970s to help run the family business. I actually felt lucky that I personally did not know the story (there are books about his family) and I could hear it firsthand in his own words and through his own experience.

At the end of the meal, he tried, tried again and invited me back to his house for a night cap. I reminded him of safety rule #1, but I didn’t want the night to end. I suggested a night cap at the bar and we enjoyed a fantastic Amaro – something I had neither heard of nor tasted previously.

As the evening wound down, he walked me to my car and we paused to next to it to continue our conversations. It was hard to say good-bye.

By his smiles, laughs, casual brushes and touches against my arm all evening and well of course the invite back to his, I knew he was into me. When he leaned in and only gave me a hug, I was a bit bolder than usual and asked him for a kiss. He smiled, placed his hand on my upper back and affirmed my request.

It will go down as one of the most bizarre first kisses I had ever experienced.

It had no natural rhythm or cadence. I couldn’t figure out the timing of when to open and close my mouth. And his tongue was beating to its own drummer. I learned during subsequent meetings to just give up on the rhythm and let him lead the lip locking party. Sometimes committing to awkward lengths of an open mouth, eventually I figured out his style.

As strange as it was, I was intrigued – I’ll admit slightly star struck as well. I was curious about a man 25 years older than me (he was and still is the oldest I’ve ever dated), but also genuinely interested in him and wanted to spend more time together. He was sexy as hell, interesting to talk to and I was already learning a bunch – and drinking practically untouchable wines (by their price points).

It wasn’t long before I got the second date invite to his house or rather his estate. It was tucked behind some high rolling hills – a solid 5 minute drive from the main road – through vineyards and olive groves. I passed land worker housing and a production facility led by periodic posted signs with his house number. It eventually took me to a one lane drive, which climbed and wound passed thick tree growth. The coded gate was open for me and when I crested the final hill the view that was unveiled was amazing to behold.

I could see the eastern mountains in the distance. Vineyards flanked the long drive on either side and the asphalt turned to tan and white pebbles, lush grass to the right and a house all on one level spanning in both directions. I wasn’t exactly sure where the front door was.

I parked, and collected myself and my belongings. Since Christmas was near, I brought him a Christmas Cactus. I wouldn’t dare bring wine but it felt fitting, respectful and grateful to bring something. I wanted it to be thoughtful and personal.

My mom had bought me a Christmas Cactus when I was little. It sat on my bedroom window sill all year long and had thick green leaves – a bit holly-like but with rounded edges rather than pointy ones. Only in the winter did beautiful deep pink flowers emerge and this one I gave him was in bloom. He was outwardly appreciative, but I had a lingering thought that my $8 gift fell short.

He asked me if I would like a Negroni. I was embarrassed that I had never heard of the drink. This offer started at least what is now a four year obsession. I only drink them the way he made them – Bombay Sapphire with a fresh orange juice splash. Bitter sweet.

He had started preparations for dinner – what he termed his “Man Meals.” This was a random collection of one protein plus whatever veggies and starch was in season from a local farm market stand at the indoor culinary hall in town. He had known the owners, his contemporaries, for decades – naturally. He would typically throw everything on a sheet tray, drizzle with olive oil and salt and roast.

He had also laid out a simple array of local cheeses, crackers and nuts to nibble on.

It was dark and cold outside so we sat by the fireplace in the large expansive kitchen that included a well out fitted cooking area. Indoor grill top, two sink areas, built in wine fridge and counter tops that went on for days. This all opened to a dining area – rustic circular table which could seat eight comfortably plus wood fireplace and seating area with a long white couch, two individual chairs, coffee table and work desk in the corner. There was a butler door leading to the formal dining room, walk-in pantry and the longest sliding glass doors that accordioned open to bring the outside in during warmer months.

We sipped our Negronis and enjoyed the hot fire on our backs. He looked so handsome by firelight – glowing embers reflecting on his face. I can hardly remember what we talked about.

Each time he crossed and uncrossed his legs, he used it as an opportunity to move closer in until finally he leaned in to kiss me. Still just as strange, but I was starting to get the hang of it. He paused and pulled back for a moment.

“Ohhh baby!”

I smiled. “Why thank you!”

I was helping him finish up dinner and get ready to plate everything when he told me he needed to go and check on the trees outside, talk to them and see how they were doing that day. I was puzzled because he told this story with such a serious, straight face. He opened the sliding door at the farthest end and disappeared into the night. After hearing this story several times over the next few weeks, my brains synapsis finally connected that he was going outside to pee.

He came back in.


He disappeared down the hall and then down a set of stairs. After a few minutes he reemerged with a bottle of 2008 Nebbiolo. He popped it and poured it right into our glasses set at the table.

Then he joined me in the kitchen, pulled the plates from the warming drawer and plated salmon, leeks, carrots, broccolini and fingering potatoes. Dinner always included an unusually large selection of vegetables.

We ate, we talked, we drank, we listened to music playing on the speakers mounted across the room. The fire in the distance kept the space cozy and the light dim. We sat there for a long while enjoying each other’s company and finally the last drops of wine went in to each of our glasses. He invited me back to the fireplace to enjoy it only we didn’t do much talking after that.

He sat right next to me in front of the fire and picked up my legs to drape over his. He put his hand on my cheek and gave me a very deep, very open mouthed kiss. I let him lead and I was getting more than hot from the fire.

“Would you like to continue this in my bedroom?”

I nodded.

He led me down a long corridor passed the formal living room, formal dining room, and the front door which I had entered when I arrived. Then passed perhaps three or four or maybe more closed doors, which I assume were bedrooms. When the hall took a sharp left, we took a right through slightly open double doors, down three steps to his sunken master bedroom. It had large floor to ceiling windows, a fireplace and a king bed. He sat on a chair to remove his boots and clothing. I did the same at the edge of the bed.

He was slim and quite toned – a swimmer’s body. Moderately hairy chest with salt and pepper fuzz. He had pecs, bis and I could even see definition in his abs. His cock was quite long and slender.

He met me where I sat, bent down slightly putting both hands on either side of my thighs and began kissing me while pushing me backward on the bed. I laid down and started to slide backward toward the top of the bed when he put his hands on my thighs and squeezed gently to signal me to stop.

He knelt on the floor at the edge of the bed, coaxed my hips to the edge and buried his beard in my pussy. A little forceful at the start, he read the movement of my hips and my breathing and found his rhythm there. I was concerned about all the wine and gin being an obstacle to my orgasm, but his dedicated efforts were quite successful in the end.

After several minutes of grinding my hips to the tune of his tongue on my clit, I could feel the rush of my orgasm coming. I pressed forward into his face, arched my back and exploded. I kept my expletives G-rated this evening not knowing how he might react. He hadn’t really thrown out many F- or S-bombs since we met.

As I was coming down, writhing and twitching, he pushed me slightly forward so I was fully on the bed, climbed on top of me and thrust his hard, long cock into my soaking pussy. He laid his chest on mine and I put my arms around his back to pull him close. His groans were guttural and deep. His cock was so long that with his most enthusiastic thrusts he could go no further inside of me – an instant of enjoyable pain I had never experienced.

He didn’t hold back verbally when he came – rose up off my chest and with one last enthusiastic pump, came, screamed wordless noises from the depths of his insides. He pulled out and flopped next to me on the bed. He pulled the blankets down and we tucked in. He put his hand on the side of my head as I was adjusting so it lay on his chest.

“My god, you sexy woman!”

I smiled and we sat there quietly enjoying our skin contact and heavy breathing coming back to normal.

Eventually he asked if I’d like a rinse. He led me to his bathroom which was up three steps on the other side of the bed from the three steps leading into and out of the bedroom.

It had two sinks, master jacuzzi tub that would easily fit two, a toilet room with a door, a glass shower and doorway leading to his walk-in closet. He turned on the water in the shower and invited me in. He picked up a shower sponge, pumped some lavender soap on it and began washing me from head to toe. He pressed his chest to my back, reached around and washed my chest with the sponge while kissing my neck.

I felt like I had stepped into a sexy movie scene.

We finished up, dried off, redressed and he walked me out to my car. He told me what a lovely time he had and that he hoped we could do it again soon. I agreed. He knelt down to give me a quick kiss while I sat in the driver’s seat of my car with the door open.

I drove home in a fog.

“The moon is rising above the mountains. Your parting kiss raises my hopes of seeing you again.”

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