Why Sex With a 50 Year Old Was The Best Sex I’ve Ever Had

What the 26 year age gap taught me

Matilda Swinney
Apr 12, 2020 · 5 min read
Photo by Jonathan Francisca on Unsplash

He was an imposing figure. His black suit was perfectly fitted and his thick set build made me nervous. He strode towards me and before I could protest, he kissed me hard on the mouth. We had never met in person. Kissing felt too intimate for a first meeting.

He smiled and didn’t say a word. As we sat together in the lobby of a five-star hotel (which he had booked), I felt sick with nerves. I hadn’t had sex for nine months. This was a long-awaited arrangement. And as much as I was horny beyond what felt healthy, I was apprehensive. Was I ready for this?

For my welcome back into the world of sex, I wanted to cut the ribbon with the best sex I’d ever had. And I believed this 51-year-old man could deliver the goods.

I had shared my fantasies of being dominated and his responses had turned me on.

I was 24 years old, still tanned from my solo-explorations around South East Asia and ready for some serious sexual excitement. Nine months meditating without any romance or sex, is a long time.

I was ready to ditch my sainthood for rough sex. That’s what I wanted — rough, breathless sex where the man took control and gave me pleasure beyond what I could ever imagine.

As he silently watched me, I surveyed his quiet confidence and self-surety. He was everything I thought an older man would be.

He had said 41, but he had to be 51. The lines on his face gave him away. I was only 24.

But, what did I care? He was handsome, confident and impossibly sexy.

I had always had a thing for authority. I enjoyed many a masturbation fantasy involving teachers, police or bosses. Plus, my boyfriends were always 2 or 3 years older, but 26 years? I was really pushing the boat out. I was in uncharted waters, and I hoped my risk would pay off.

“You’re very beautiful,” He said quietly.

I blushed instantly.

“You will get ready in the hotel room and meet me in 30 minutes. Remember to wear exactly what I told you,” He ordered.

I nodded silently and walked away in relief to our room. He made me nervous. Plus, I barely had any time to get ready. 30 minutes? Who could get ready that quickly? I had to have a shower, do my hair, do my makeup and get dressed. This was going to be a world record.

“Please sit.”

I had arrived in the plush bar of the hotel, only three minutes late. I sat down obediently next to my mysterious dominant man. Part of me was starting to regret my decision. I felt in over my head. The hotel was far too glamorous for me and the cocktail prices were more than I would pay for a whole new outfit.

Plus, nine months was a long time. Was I ready to feel the fingers of a man I didn’t know inside me? Did I want a cock stretching me open? My pussy pulsated at the thought. I smiled. The answer was a resounding yes.

In fact, it flowed. And so did the drinks. Within a few hours, I was ready. I craved the feeling of this man’s cock inside me. I sat closely, breathing in his heavy expensive fragrance. I let my glossy legs brush against the smoothness of his perfect suit trousers. I wanted him now.

“Stand with your back to the door, hands behind your back. Wait for me,” He said slowly, looking into my eyes.

I walked slowly to our hotel room, and did exactly as he had ordered. My heart was racing, but the multiple cocktails I had consumed over the past few hours, were numbing my nerves perfectly. I was ready.

The door clicked open. I smelt his familiar gorgeous fragrance. I felt his cold breath on my neck. I shivered. Before I could say or do anything, he pushed his fingers forcefully inside me.

“You’re wet,” He whispered.

I blushed in the darkness of the hotel room. His fingers felt strange. It was such an intimate act. He was invading me. I hadn’t even touched myself in nine months. It hurt. His fingers were thicker than I expected.

But, as I became more and more turned on, I moved myself against his thick fingers. I wanted them deeper and deeper inside me. I moaned softly and came helplessly on his hand. The pleasure had taken over without warning.

I hadn’t anticipated an orgasm so early on in our sexual experience together. Perhaps, it was the alcohol, the way he looked at me over cocktails, or his strong quick moving fingers.

The way he flung me across the bed and tugged my hair as he took me roughly from behind, made me dizzy with pleasure.

After nine months, the sensations were too much to handle. Plus, no man had ever pushed this deep inside me or been this rough with me before. No one, not even my five-year-long boyfriend, had known my body as intimately as this older man did.

He knew exactly where to finger me to make me squirt, how hard to pull my hair, how deep to enter me and the exact words which would melt me into the deepest orgasm I had ever felt.

I had never experienced such perfect sex. Our connection to each other’s pleasure, his intuitive knowledge of my boundaries, and his accurate pushing of my edges to immerse me wholly in a deeply carnal experience of sex, was out of this world.

Was his much older age the reason?

Or was it our natural energy together, and perfectly matched sexual desires? He wanted to dominate, I wanted to submit. But, it was more than that. There are many layers to each desire. And his layers matched mine exactly.

Sure, his many years must have given him practice, confidence and a self-surety within him. He was a man who knew exactly what he wanted. He moved without hesitation, talked only when necessary and allowed silence to be a third member of our conversation.

He was strong, peaceful and unbearably sexy.

I was wet. In fact, I was so wet I licked my finger to check it wasn’t blood. How could I be this wet still?

A lick of my own juices confirmed it was my horniness alone that was dripping down my thigh. I laid back in the four-poster bed and fingered myself to another final orgasm, before sinking into a deep sleep.

I enjoyed nine hours of the kind of sleep only possible after such wonderfully satisfying sex. My nine-month sainthood was over. I had cut the ribbon with a flourish.


Conversations about sex from all around the world

Matilda Swinney

Written by

Sex, life & mental health | P.S I Love You | Mind Cafe | Find out how to go from 0 to $1k on Medium with my free six-day writing course pages.matildaswinney.com


Conversations about sex from all around the world

Matilda Swinney

Written by

Sex, life & mental health | P.S I Love You | Mind Cafe | Find out how to go from 0 to $1k on Medium with my free six-day writing course pages.matildaswinney.com


Conversations about sex from all around the world

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