Ever since I had a two week affair with the neighbor two doors down from my family’s beach house in NC two years ago, I’ve had a thing for older men. I mean older.
6′, white balding hair, British Canadian from Montreal, retired banker who still dabbles, not too big of a belly, flat ass, old man cologne, divorced, no kids, building a home in VT, globe trotter.
When I saw his picture on Tinder, it took me a minute to swipe right. This dude looked OLD…but my curiosity got the better of me. What would it be like to date someone who could be my dad, literally?
We matched. After some very proper introductory conversation via text, he invited me to dinner up valley. I felt compelled to wear something more conservative than usual to our first date.
I walked in to the bar and spotted him standing at the end looking like, well, a grandpa. We made eye contact and I walked over. As soon as I got close enough, I smelled stodgy old British man cologne. Yes, his teeth were f’d.
What the flying fuck am I doing?!?
He was drinking a lovely $20+ glass of Chablis. I ordered the second most expensive Zin.
I can only describe our initial conversation as exchanging pleasantries. But there was something there. My mood pivoted from dread.
We moved to a bar table for dinner. I ordered whatever the fuck I wanted. $14 cocktails. Sweetbreads. Lamb.
He had the waiter open and decant the 1995 bottle of Grand Cru Bordeaux he brought.
Ok, maybe I’m easily persuaded by expensive food and drink, but the conversation was on point. We clicked. We talked about great wine, great food, great travel. I was actually having fun.
Uncharacteristic of me, I accepted an invitation for a nightcap back at his house. He lived just around the block in what he dubbed, a “bungalow.” A $1.6M 2 bedroom, 2 bath house with a small guest house and garden in the back, which he had gutted and completely remodeled after his divorce two years earlier. The inside looked like no one lived there. I was afraid to touch anything.
He opened a bottle of vintage champagne. We talked through that entire bottle.
It was late and a “school” night, so he walked me to my car. Standing next to the driver’s side door in the blue moonlight, he went in for the first kiss. Very respectable, slightly opened mouth, no tongue effort.
We went on a few more dates. Some lunches during the week. Some dinners. It was going swimmingly and I loved being spoiled so much. He texted me love notes all the time. It was too adorable.
“I am a truly romantic man and hope to convince you of my attributes one of these days!”
“Yes, I was thinking about the weekends and maybe kidnap you once we get to know each other better and head up or down the coast.”
“There is no greater high for me than to make love to a woman you adore and spend long days and nights together enjoying laughter, great food and wine and unending passion!😋”
“I would like to kiss you well into the wee hours!💋💋💋”
The night before my birthday he invited me to a home-cooked meal at his house.
“Thinking rack of lamb, truffle mashed potatoes and green beans and you for dessert.”
He had chilled champagne and a handsome array of cheeses for me to nibble while he finished cooking dinner. We ate dinner at a very properly set dining table. He even got me a birthday card with a lovely handwritten note.
We moved back to the kitchen bar stools for strawberry shortcake, Sauternes and espresso. He moved his stool close to me and moved his hand up my thigh under my dress leaned in and gave me a long, deep kiss. It sent tingles all over my body that settled in my pussy.
I stood up and moved in between his legs. He surrounded me with his arms and hands moving them up and down over my back, ass, thighs.
He met my lips with his, and I could feel his cock getting hard against my thigh. It was full and long. He put his hand through the back of my hair.
Then I chickened out.
Oh, god, I can’t fuck a grandpa!
I made my excuses of work in the morning. It was a Tuesday after all.
“I’m home darling 😉 What an exceptionally fun evening, thank you!”
“Glad you are home safely. I want your affection and was afraid I pushed the limits a bit tonight!”
He called my bluff.
“I really wanted to take you to my bed and undress you slowly as I enjoyed every inch of you and then…”
I marinaded on the idea for a few days, and thought WTF. Maybe he’d be an amazing lover. Experience, focus on pleasing me, what more could I want?
We had another lunch or dinner or two, but alas he faded away.
I saw him recently at the bar of a restaurant where I was meeting a donor for lunch. I gave him a hug and smooch, and then rushed off to meet her.
I had hoped he might text me after that, but no. Guess I’ll have to keeping dreaming of grandpa.