He initially spotted her, on line, checking in well ahead of him. First glimpse was from behind but spectacular. Fitted shorts and comfortable looking 3 inch heels beautifully highlighted gorgeous, shapely legs, and a terrific rear. Streaked, shoulder length blonde hair came to rest on a tight, semi-sheer white halter top. He figured she was probably about 5'8" tall, obviously in great shape, and likely in her early 40's.
Spinning away from the desk she was all he could have hoped for and more; quite beautiful, with a radiant smile, and sparkling eyes. Her genuine warmth, mixing deliciously with a powerfully confident sensuality, began drawing him in.
Given all that "upside" he began looking for the boyfriend, lover, or hubby lucky enough to be sharing the next week with this very hot lady. Seeing nary a one gave him some hope that starting a relationship was, however unlikely, possible.
The odds were not made better by the fact guests at this expansive, beautiful Caribbean resort each got their own cottage, with a deck, hot tub and small pool. It's not like a hotel, where things are designed to give folks increased opportunities for interaction. Here you could just choose hanging out "close to home".
Maybe that's why she picked this particular vacation spot. It's not the worst place to go if you're traveling solo, and need to get away. It's also not the worst place to go if you're alone and looking to meet someone. He's done it before and found, for the most part, the ladies to be intelligent and attractive.
Even while unpacking and admiring the lovely accommodations, that woman's stunning image remained. He felt like a school boy with a crush, doomed to have blown the only opportunity to connect with this goddess.
Then came the formulation of a plan. That gal didn't get such a sensational shape by sitting on her butt all day. She must be big into tough workouts, which means there will be trips to the gym. Now it was just a matter of "running into her" at the facility. It's not like he was a couch potato. Exercising was split pretty equally between swimming, weight lifting, light running, and working out on a speed bag. It's not like he wouldn't look good on any of the machines.
First day, no luck. But on the second day she was heading out as he was walking in. Even after a workout the woman was a vision. Having to say something, out tumbled the words, "Wow, you must have begun awfully early if you're leaving before 9 AM."
Graciously ignoring his awkward attempt to start a conversation, she smiled broadly and said, "I'm used to getting a very early workout in. Actually, this is late for me. Gotten all lazy down here in the tropics."
Feeling more comfy now he smiled back saying, "Well it sure looks like it's paying off for you. Hope I didn't overstep there, but facts are facts."
"Not at all. That's very kind of you to say. Sweet."
"You made it pretty easy really. My name is James...Jim or Jimbo if you'd prefer."
Chuckling she responded, "Hope those aren't all aliases. I mean you seem kinda nice. I'm Jean, Jeannie if you'd like."
Well, how about that. This gal's quick with a genuine sense of humor.
Glancing at her watch, "Oh. Gotta run James."
"Hold on Jeannie. You can't run off like this. It's not fair. When can I expect to see you again?"
Laughing out loud, "About anytime I guess. We're sorta neighbors."
How could he have missed that? Maybe Jean was just being a tease. God, how Jim loved a good teasing, and his bet, was she was great at it. Kidding or not, his fire for her was stoked even more.
Taking a run on the beach helped him better sort through that brief conversation, but unanswered remained the whole neighbor question. If Jean wasn't just playing that means she'd seen him before he'd found her. And if she was playing, it proved she really enjoyed the idea of "arousing" his curiosity. Either way it was a win, win. But the idea Jean had thought enough of him to take notice, without him knowing, really was encouraging.
Arriving back at his cottage, Jim scanned the landscape. It was thick with lovely trees and high, flowering plants. And up until Jean mentioned her alleged proximity, he'd never really considered seriously scouting houses surrounding his own. It seemed too much to ask she'd be so close.
But now things were different, so let the reconnaissance begin. There were three possibilities; bungalows on each side and one in the back. By virtue of an older couple settling in, the latter mentioned was eliminated. Ditto the cottage on the right, for a similar reason. That narrowed the focus to uno. James found a relatively comfortable spot, grabbed a cold beer, and began to observe.
Around dusk he saw movement. A form walking into the cottage, became clearer when she turned on the light. Jim could hardly believe his eyes. It was Jean. Wearing her hair down, sporting heels, and a lovely, form fitting dress, it looked as if she'd just returned from dinner.
After lighting some candles, and turning out the light, Jean began undressing. Ever so slowly, leaving on her heels, she slipped out of that skin tight garment, revealing a low cut, black, push up bra, and a dark, barely there thong. Jeannie was simply remarkable. Jim wanted to think she knew he was watching, but that seemed especially immodest. Still he couldn't help but remember her gentle taunt about them being kinda neighbors. Given that, it appeared, from the lighting of the candles, to the terrifically sensual disrobing she might truly be aware that he couldn't take his eyes off her.
She moved towards the hot tub and started the jets. Kicking off her heels, she stepped into the swirling water. Next item of clothing to come off was the bra. Jean's breasts were lovely and full. No sooner had Jim begun processing that wonderful eye candy, then he saw her remove her thong and wade directly towards one of the pulsing jets.
Her back towards him, she lifted an ankle out of the water, next running her hands along that gorgeous leg until they disappeared. Head back, perhaps emitting a slight moan, she continued to explore. He grew hard watching, trying to imagine, what she was fantasizing, and longing to replace her skilled fingers with his talented tongue. Jim stroked his throbbing erection gently, silently hoping she would notice how much watching her fantasize under the stars was arousing him. Realizing she may be aware and even excited by his voyeurism he became increasingly erect, stroking himself more quickly.
Completely hard, he now wanted her to see the powerful affect her masturbating was having on him. She teasingly traced her lips with her tongue and repositioned herself. Moving to the edge, obviously exploring further, Jean seemingly lost in her own passionate eroticism appeared, to partially muffle a carnal cry, shook, and then began a powerful, extended orgasm.
Jim wanted to cum right along with her, but held back. Perhaps he thought it best to demonstrate the kind of control expected to satisfy a woman like this. What if the entire scenario was geared to test his "staying power". How would it look if he couldn't last 10 minutes just watching Jeannie masturbate?
