It was mid-March and the weather in Milan was colder and greyer than I was expecting. I mentioned this to my sexy, mature next door neighbour Daniella—the lady that I had been having a complicated affair with for the last three months—and she suggested that we get out of the city for a long weekend to find some sun.
A couple days later we found ourselves in a pair of sun loungers near a pool overlooking the ocean at a fancy resort on a small isolated Greek island. The place was amazing and, since it was still early in the season, there weren't many other tourists around.
Given my pasty white American skin, I was doing my best not to get skin cancer by hiding under a sun umbrella, whereas Daniella lay fully exposed to the sun next to me. Since we arrive yesterday, her skin had turned from a soft mature brown to a full golden Mediterranean bronze, and given that this was Greece, she insisted on tanning without her top on. I could almost see her nipples and areolas growing darker by the second.
As I was there trying not to stare at her breasts, a cool spring breeze blew in off the ocean and over the top of us. Instantly her nipples grew erect, standing a good centimetre or two in the air. In my red swim shorts, my cock gave an involuntary twinge and began to get hard. The sexually repressed American in me quickly looked around in fear half expecting some old woman with a goat to scream in horror at the growing bulge in my shorts. It must have be too early in the season for morality police to be out on patrol, for no one screamed. In fact, the only other people out at the pool were two much older German women, who were also topless, who clearly couldn't care less about the state of my erection. I turned my attention back to Daniella's breast.
The last three months with Daniella had been strange. First, I had to think of what I meant by the word 'with.' From the very beginning we both made it very clear that we weren't dating, seeing each other, or any other of those happy, couple euphemisms. I just got out of a bad divorce and still wasn't ready to start seeing other people, and Daniella was cool with that. And Daniella made it clear that she had other commitments and 'hobbies' that made seeing another person hard.
And then there was the sex. We had sex. Lots of sex. Good wholesome, knees trembling sex, but it was pretty clear from the first moment I found her tied to her bed with the naked guy knocked out cold on the floor next to her, that sexually she was in a different league than me. She had certain appetites that either I couldn't fill, or, at the very best, would kill me if I attempted to fill them. But to her credit, she never demanded that I fill them, so in a way it never became a problem.
Then there was the age difference. She was somewhere between 10 to 20 years older than me, depending on who she was talking to or what story she was telling. I suspect that it was closer to 20. However maybe because she was older, I never had that ego driven, hormonally induced, cave man response to dominate her. She was in charge and we both knew it, but she was a benevolent dictator. She never humiliated me. She always kept me involved in what ever see was doing. And I always got to cum as much as I want.
In short, yes, this is a fucked-up situation, but there was a part of my brain—or maybe my penis—that kept whispering, 'let's see where this goes.'
"Let's see where this goes," I mumbled to myself.
"Cosa?" Daniella asked in Italian before remember that I was crap at Italian and switched to English, "sorry, I was asleep. Did you say something?"
"I was just thinking of getting drink. Do you want one?"
Daniella sat up in her sun lounger and turned towards me. With one hand she readjusted her sunglasses and then soothed down her curly auburn hair. With her other hand she absentmindedly pulled at her still erect left nipple. "Yes please, you know what I like."
I stood up and started to turn towards the bar.
"Theo!" Daniella shouted to get my attention.
I spun around to see her smiling, "be careful at the bar. They may see your erection," as she pointed at the bulge in my shorts.
Like a horny teenage boy in swim class, I did my best to physically shove it back down which only made it worse. Eventually I snatched the beach towel from my sun lounger and was off. Ten minutes later I returned with our drinks. While I gone, she had moved both of our sunlounges under the big umbrella and was now sitting up, gazing out on the nearly empty pool.
"Here is your drink."
"Grazie," she smiled before grabbing the ice cold and sweating glass and took a drink. "Did they see your erection at the bar?" she asked casually.
