My best sex ever was... with a holiday rep

Sarah’s* sun-soaked holiday was all-inclusive in more ways than one…

I met Paolo* on a family holiday to Crete. I’d just turned 18 and was lying by the pool when his tanned figure cast a shadow across my suntrap. He was just my type – cheeky, shaggy hair, lean body. And the water dripping from his clinging trunks onto the terracotta tiles didn’t exactly hurt.

As part of the resort’s entertainment team, it was Paolo’s job to make sure all the guests had fun. My days soon filled with the sporting events he led, like beach volleyball and water polo. We got competitive and began to flirt. I regularly floored him in volleyball and among the scuffles, sand and endless quips, his once-demonstrative hands started to linger. Our constant competing was exhausting bliss – I even smashed him at archery. And with winning comes reward. At night, in the resort’s club, we’d dance a little too closely, his fingers roaming as we moved to noughties R&B songs.

I could feel the sexual tension rising and thought it would remain just that. But on the penultimate night of my holiday, Paolo performed in a staff striptease to crown the day’s sporting winners. His cockiness turned me on, and his eyes devoured me as if I were the naked one. I stubbornly held his gaze until the finale.

When he was decent again (and my giggles had subsided), we went outside for some air. For the first time, we were entirely alone. He pushed me against the wall and we kissed hungrily. As his lips grazed my jaw, he asked if I’d like to meet later, when everything had closed. I agreed.

We reconvened by the staff changing room, behind the stage where he’d performed earlier. Hastily, he unlocked it and guided me past hanging costumes and glittery props to a dressing table. He sat me on its ledge and slipped his hands under my dress, sliding my knickers off. Grabbing my thighs, he crouched down and started sucking my clit. He was commanding and didn’t need me to tell him what to do. He prioritised my satisfaction over his own, and I climaxed before he’d even taken off his shorts.

My body was so fizzy with pleasure that I hardly noticed him fumble for a condom and reposition me into missionary, let alone the hard surface below. Wrapping my legs around him, I couldn’t take my eyes off his muscular body as he entered me. Gasping, I dug my nails into his back, but he moved them to his bum, in case people noticed the scratch marks when he was working. I pulled him in deeper and arched my back. He went faster and, as I tensed, finished loudly.

We collapsed in delight and joked about what it would be like tomorrow, hoping things wouldn’t be awkward. He escorted me to my room and disappeared to the staff quarters. My heart was pounding with adrenalin as I got back into bed.

The next day, the last of my holiday, he greeted me with a wink. We added each other on Facebook, but nothing came of it, although our flirtation was all I could think about for weeks after.

“I climaxed before he’d even taken off his shorts”