This story took place a few years ago when I traveled for work heavily. I had to attend a conference in Hawaii (tragic, I know) and I was planning on bringing along my girlfriend at the time. After the conference we were going to extend our stay and meet two of our friends, a couple, for a duo vacation island hopping.
Unfortunately, my girlfriend had a medical emergency (non-life threatening if treated) and had to go to the hospital a couple of days before we were slated to leave. We were all very bummed. I offered to stay with her and cancel the whole trip but she declined and told me to go and have fun without her.
I left for the trip quite happy and looking forward to experiencing the natural beauty of the islands again. I'd already been to most of them a few times before this and they were (and still are) my favorite places on the planet. Conferences in general can be boring, but I'd managed to have fun at them in the past when I was single. Something about being away from home really awakens the animal in people and in the paradise of a place like Hawaii, double so. I'd slept with many women that I either knew were taken or found out were taken later. And many of my married male colleagues indulged in similar levels of depravity on the road.
But I was on the straight and narrow at this point, leaving behind the flexible morals of my youth to strive for a more stable future. My girlfriend at the time, Elizabeth, was gorgeous. She had wavy dirty blonde hair that fell to the middle of her back. She was a former track athlete with thick legs that went on for days. Her ass that was so perfectly shaped even my closest friends had a hard time politely avoiding looking at it. This combined with her slightly aloof but flirty girl next door vibe had men falling for her constantly. Sexually we were more than compatible and at 18 months into our relationship we still fucked constantly. She wasn't the most over-the-top lover, but she had a high sex drive, an incredible body, and was kind of addicted to my cock.
As for me, I'm 6'2, muscular, athletic, and of Italian and Dutch heritage. Tall dark and handsome, some would say. I don't work quite as hard on my body as I did in my early twenties so the abs come and go. But I am an animal in the gym and women have always enjoyed my powerful body. My dick isn't as massive as some porn stars but he's brought joy to many of my lovers. A little over 7 inches in length, plenty of girth, and perfect symmetry. Ever since I realized what I had I became very grateful for him.
Elizabeth and I had been faithful for the entirety of our relationship so far and I had no secret agendas now that I was alone. I just wanted to get through the conference and go explore the islands with my friends. Despite maintaining a high level of physical intimacy Elizabeth and I weren't without our struggles. We had fundamentally different beliefs about the world and our divergent life goals reflected that. We had both been looking forward to the trip as being a way to reconnect and establish some intimacy beyond the physical. A death throw, in retrospect, but still we had hope.
At this particular conference a few years ago (when I was single) I stumbled into a FWB/semi-committed relationship with a young graduate student named Leah. Leah was Colombian and French. As you could probably guess from that combo, she was an absolute work of art of a woman both inside and out. Charming, sweet, incredibly intellect, and a body you could spend a lifetime trying to artificially recreate and never succeed. Our flame burned out due to unmanageable long distance, but we maintained occasional contact. When both of us were single and near each other at industry events we would rendezvous for some casual fun and relive a bit of the spark we shared.
I was her first big cock and helped her discover she could orgasm from penetration; she was my first "younger" woman by an age gap of 7 years and we both found the dynamic kinda hot. When we first started seeing each other she (23) loved to tease me about my age (30), calling me "Old man" to get a rise out of me. She must have seen me at the convention center because I got a text asking if I wanted to meet up for some fun later. I told her I was in a relationship and wasn't sure it was a good idea. She said, "No problem" and offered to instead meet up for a casual drink just to catch up.
I don't know if it was naivety or that I subconsciously lied to myself in the moment, but I agreed to meet her. It seemed so harmless, and I'd been in plenty of tempting situations before and stayed faithful. That night I spoke to Elizabeth on her hospital phone and she asked if I had anything going on. I lied and said I was just going to go to my hotel that night to lay low and get some rest.
I felt the push and pull of my emotions physically while we were on the phone. It was like my stomach was vibrating inside of me, warming me with anxiety and anticipation as my limbs went cold. But I just couldn't say no to meeting Leah. Besides, it was just a catch up and Elizabeth needn't get jealous over something as harmless as one drink.
Smash cut to the bar and a few quickly consumed cocktails later and Leah and I were right back to where we started. Our eye contact refused to break and we were fully in our own world. I was well off my game and telling bad jokes due to my nerves, but she was laughing at them anyway. Her jet-black curls were twisted up in a neat bun with a few strands of hair dangling in front of her perfect tan dimples.
My stomach played host to a war of excitement and guilt. She was such a knockout that even her modest outfits couldn't conceal her figure. I tried to blink away my eyes retracing the curves that I had once freely explored and couldn't forget. My heart was thumping in my chest but felt like it was only sending blood to my slowly swelling dick. I tried to fight it. I really did. But her sing song vocal tones and musical Latin cadence... the way she trailed her hand across my broad shoulders when she was flirting... I couldn't take it anymore. "I have to leave." I thought.
I was about to say it out loud when she put the final nail in my coffin. "I'm going to smoke a joint on my balcony before I crash. Want to join me? No pressure." I froze. My eyes were trapped in hers. I opened my mouth and closed it, then looked away. A flash of Elizabeth's face appeared in my mind's eye. I looked back up. The soft dimples. The kind, inviting brown eyes. The sensual lips. "I uhm... I... yea. Yes, let's do it." On the walk back we couldn't stop laughing and tipsily stumbling into each other.
Lianna put her arm through mine to stabilize herself and we were both grinning ear to ear. The elevator ride up was quiet and tense. We could both sense what was happening and neither one of us could stop it. Back at her room we both used the restroom, freshened up, and then made our way to the balcony. She pulled out a fat pre-roll and sparked it. We talked about life and family a bit and caught up on more serious topics.
As the joint burned our conversation made its way to pleasantly recollecting the memories of our short-lived situationship. Our voices and soft laughter carried in the clear ocean air. The unmolested night sky and the whisps of smoke dancing around her stunning profile had me totally in awe of her. She had become quite the woman since our first romps years ago and I wished she was still mine.
I felt the pulse in my crotch travel up my spine and ring like a bell in my head. The heat in my balls heralded the last releases of testosterone that would spur me on to complete my ancient duty as a man. I told her to shotgun me. As she raised her hands to blow the smoke into my mouth, I grabbed them, pulled them aside, and leaned my face into hers. We held the kiss and she dropped what was left of the joint, frozen on each other. Neither of us said a word and immediately we started to make out slowly and sensually.
