The Dog, The Shirt, & The Wardrobe

By May 2007, the rope finally snapped. I broke up with Vanessa after five months. The sex was spectacular—the best of my life—but I couldn't live with the lies anymore. The mythomania, the secret phone calls, the constant drama... I was exhausted. Trust is the currency of a relationship, and we were bankrupt.

I lost contact with the first swinger couple (Paulo and Juliana), but I stayed friends with Nuno and Alice. Alice was eager to get me back into the lifestyle. "I want to fuck you again," she told me bluntly. "But you need a girlfriend to get in the door."

She tried to play matchmaker, introducing me to three of her girlfriends. None of them fit the bill. I was single and out of the game.

But as one door closed, an old one reopened. Helena—the "Classy Lady" with the nipple fetish from the beginning of the year—was single again. We met for coffee in the city. We bonded over our failed relationships. I complained about Vanessa’s lies; she complained about her ex. We decided we both needed an escape.

"Let's go on holiday," I suggested. "A week on a Mediterranean island." She agreed, with one condition: "Only as friends." "Of course," I lied.

A few days later, Helena came to my apartment in the city to plan the trip. The "Friends Only" rule lasted about fifteen minutes. The chemistry that had sparked months ago was still there. We started kissing. Her tooth problems were long gone, and she showed off her full skillset with a delicious blowjob. She was hornier than ever. Her pussy was soaking wet.

I moved behind her. She lay on her belly, and I took her doggy style, grabbing her big tits and pinching her hard nipples—her signature trigger. I exploded on her back. By request, I lay my full weight on top of her, continuing to pinch her nipples while she felt my hot cum on her skin. She came just from the sensation. So much for "just friends."

In June, we flew to the Mediterranean. I had booked a room with a double bed. She didn't complain... until the first night. When I jumped on her, she resisted. "I told you, I don't want this."

But I am a persistent man. I kissed her until the resistance melted. We had sex, and I thought the tone was set for the week. I was wrong. The next morning, the wall went up. She became distant. We entered "Real Friends Mode"—going to the beach, talking about our exes, analyzing our failures. It was frustrating. I was sleeping next to a woman I knew was a sexual dynamo, but I was living like a monk.

However, biology wins in the end. On the last night, the wall crumbled. I barely had to try. We shagged again, ending the trip on a high note.

Back in the city, things cooled off. The holiday had been a mix of good times and awkward rejections. I tried to reconnect with Vanessa (a moment of weakness), but she disappointed me again. I needed to flush Vanessa out of my system.

I called Helena. She was at a beach in the south with a girlfriend. I rode my motorbike down to join them, hoping for a repeat of the island. Nothing. She blocked every move. I drove back thinking the affair was dead.

Then came the dinner party. Helena invited me to her place with a group of friends. I accepted.

I arrived and saw her. She looked stunning, wearing a striking red dress with ruffles that hugged her curves and showcased her elegance. She was the picture of class.

I greeted everyone, and then I greeted her dog. The dog was apparently excited to see me too. He jumped up, claws out, and ripped my shirt right down the front. "Damn it," I cursed. "Come upstairs," Helena said. "I have some of my ex-husband's shirts."

We went to the first floor. She opened the wardrobe, searching through the hangers. The setting was too perfect to ignore. I stepped up behind her. I wrapped my arms around the waist of that red dress and kissed her neck.

It was a gamble. Her friends were downstairs. She could have yelled. Instead, she leaned back. We started kissing frantically, hands roaming, the danger of getting caught adding fuel to the fire. We wanted to tear each other's clothes off right there in the closet, but we had to go back down.

I spent the rest of the dinner making polite conversation, wearing another man’s shirt, waiting for her friends to leave. Finally, the door closed behind the last guest.

"So?" I asked, standing in her living room. "Do we sleep together?"

She hesitated, trying to hold onto her "classy lady" resolve. I kissed her again. The resolve vanished. We went upstairs—not to find a shirt, but to tear the sheets. It was a fantastic, unexpected encore.