Encounter at the Outrigger Resort

Olivia, from Encounter at the Movies, is at it again. But then, maybe Olivia isn't even her real name...

I'm 400 feet above the Gulf of Mexico, hooting and hollering and waving my arms and legs like a crazy woman. This is such a RUSH! The views up here are amazing. I can see the city, the ship traffic, and even the curvature of the earth. Above me is a parasail, and the bright colors add to my mood. Out front, looking like a tiny toy is the powerful boat that pulls on my harness. The line connecting us looks finer than a human hair where it meets the boat, but here at my harness, I can see how stout it is.

Fort Myers Beach, Florida, is one of my favorite places to visit. Everything a vacationer needs is here: beautiful ocean water, white-sand beaches, restaurants, nightclubs, and resorts. There are even a few secret places tucked away where you can escape all that if you need to. I grew up near the U.S./Canada border where it's cold as fuck. My parents are gone, and my siblings all moved away, so I never go back. There's nothing for me there. In fact, I only venture north of the Mason-Dixon Line from June through August. When I'm here, I'm as close to the 'real me' as you will ever find. I relax here, but that doesn't mean I stop playing my games.

My favorite place to stay is the Outrigger Beach Resort, a small place built in the 1980s. It's three buildings, two of which have only two floors of rooms and one with four floors. It has a pool, a tiki bar, and a small restaurant. The resort also owns an upscale restaurant across the street. It's quiet here. Being on the southern end of Estero Island gives it that laid-back vibe, in stark contrast to the north end which is party central. The south end also hosts an older crowd. Want a party? Hop on the trolley and head north. Want to spend a quiet evening on the beach or watch a movie at the theater? Come to the south end. Generally, the men here are divorced if they're not with their wives, and young single guys are the exception, not the rule. If you're interested in spending the night in bed with a silver fox or a guy with a dad-bod, come to the southern end.

Most nights, I'll take the Outrigger.

Many of the guys I pick up want to get to know me. Fat chance of that happening. Want to know my name? I'll give you one that suits my mood. Want to know my background? I'll change the subject and get you talking about yourself. Men looove to talk about themselves. For me, it's anonymous, wham-bam sex, and then I'm gone. Isn't that what guys fantasize about? That brief encounter that you'll never forget? I'm a woman who sees what she wants and goes for it, living life on my terms. Maybe the man I let eat my kitty in the parking lot of a restaurant just across the Matanzas Pass bridge last night thinks I will fall for him, but honestly, I'm just a woman who gets bored easily and likes to fool around with someone I find attractive.

For now, I'm just hanging out below my parasail as my tow boat runs up and down the beachfront. I check my diver's watch and notice that my time in the air is almost over. Soon I feel the tug on my harness lighten, and I sense that I'm descending. Sure enough, the boat slows, and within a few minutes, I'm nearing the stern platform. Before launching, I had asked for a couple of dips before they reeled me in. Sure enough, the boat driver accommodates me.

As I skim the surface of the water, screaming my lungs out, I look at the beach and notice a man watching me through binoculars. I wave at him, and he waves back. He puts the binoculars to his eyes again and looks at me. I blow him a kiss. He puts his hand to his face and flings a kiss back at me. He has possibilities. I wonder where he's staying. I should probably go looking for him. He must be a new arrival because I've been here for two weeks and I haven't noticed him until now.

I'm finally reeled onto the boat, and we head north to their dock. I gather my belongings from the locker they provided me, toss on a cover-up over my tiny bikini, and slip into my sneakers. Soon I'm on the trolley, heading back to the Outrigger. Once there, I make my way to my room to shower the seawater and sweat off. It's mid-afternoon by the time I'm dressed. Time for a cocktail at the tiki bar. I slip into another bikini, a leopard print 'cheekini' actually. Mama's on the prowl. I stand at the mirror and toss my raven pixie cut, giving it that 'just fucked' look. I love the new cut and color. I'm a chameleon.

The tiki bar is popular this afternoon, there are only a couple of seats available. I pick a seat and ask the two adjacent customers if it's taken. Fuck me, one of them is binoculars guy! He recognizes me.

"You're the parasailing adrenaline junkie!"

"You're the binoculars guy!"

We both laugh and say, "Guilty" at the same time.

He's good-looking, with blonde hair that's turning silver, a touch of a dad-bod, and yummy lips shaded by a pornstache. Yep, I might have just found my next conquest.

"Steve," he says, offering me his hand.

"Tiffany," I respond, and accept his handshake.

"So, do you keep binoculars around just to scope out crazy women hanging under parasails?" I chuckle.

"No, I enjoy birdwatching," he responds.

"What brings you here?" I ask.

"A retirement gift to myself, early retirement, I'm notthat old. I've invested well and decided to enjoy the rest of my life rather than be a slave to someone else. My last day of work was December 31st. It took me a couple of days to get packed, and then I drove down from Ohio. I've been planning this for a year."

"How long are you here for?"

"I'm here at the Outrigger for two more days, then I'm heading to Key West."

"Sounds like fun; the Keys are beautiful. While you're in Key West you should see Hemmingway's house and Truman's too. Take the boat to the Dry Tortugas; it's another thing you can't miss. Of course, there's plenty of food and nightlife."

"Sounds like you're an expert; are you from Florida?"

"Oh, no. I'm from the frozen North, almost a Canadian. I spend a lot of time here now that my parents are both gone. There's nothing for me back home. The Outrigger is kinda my home away from home when I'm not roaming the world."

"Wow, that sounds exciting! What's a girl like you do to support her travel habit?"

"Financial advisor. I can do that from anywhere." A lie, but he doesn't need to know that.

We sip our cocktails as we talk, then order another round. I excuse myself to the ladies' room, and when I return, I surreptitiously slide my stool a little closer to his. We chat about everything and nothing. I press my leg against his and tickle the hair on his arms as I laugh at his stupid dad jokes.

By this time, it's almost sundown, and the crowd is growing. As the sun slips below the horizon, a man blows three blasts on a conch shell, and the bagpiper next to him plays Amazing Grace. It's a tradition at the Outrigger. As the last notes sound, the crowd begins to disperse.

We order another round, some sandwiches from the restaurant, and chat some more. It turns out he traveled extensively for his job. We have a lot of destinations in common, though he's been to many more places than I have. He asks about parasailing, and he says it looks like fun. I offer to see if we can both go before he leaves for Key West. By the time we finish our food and cocktails, it's getting late. I find out he's in the north building; I'm in the south, where the kitchenettes are.

"I'll call the company when they open tomorrow and book us a double parasailing session if you'd like," I offer as we enter the parking lot.

"Sounds great," he says, looking deep into my eyes.

I sense that he wants to kiss me, but he hesitates. I don't even know if he's married. Not that it matters. I've fucked lots of married guys. Usually, they are the most appreciative. How could I not ask? I didn't notice a ring. I guess I was so lost in him that I let the questions slip my mind. Now's not the time to ask and risk ruining the moment.

"Let's meet for breakfast, and I'll give you the details. Good night, Steve," I whisper as I rise onto my tippy toes and give him a peck on the cheek."

"Good night, Tiffany."

I turn and bounce away toward my room, putting lots of spring in my step so my ass waggles and bounces. If he wasn't hard from the flirting at the bar, then I'm sure he's hard now.

When I reach the second-floor walkway, he's still standing in the parking lot, watching me. I pause at the rail, blow him a kiss, and kick a foot up.

"We'll have fun tomorrow, Steve. Just don't go ruining things tonight when you're alone!" Well, that was about as blatant as I could get in public.Don't go beating off tonight and waste a load of your yummy cum!

I wave to him as he watches me enter my room. It's obvious that he's interested, but in what? Companionship? Sex? Maybe he's a serial killer! I laugh at that last thought.

I strip down and crawl into bed. Lying there in the dark, I wonder why I didn't just jump him tonight. That's my normal modus operandi. Maybe it's because I'd have to avoid him for a few days until he leaves for Key West. Or maybe it's because I'm attracted to him in a way I'm usually not. I don't usually go after guys who are thirty-plus years older than me like Steve is. I find him intriguing; he's lived a well-traveled life. Most of my conquests don't have his life experience.

The next morning, I call the parasail company and book a double flight for mid-afternoon. Down at the deck, I spy Steve having breakfast, so I join him. I sense his excitement when I tell him about our flight.

"So, what are you doing until our flight?"

"I thought I'd walk the beach and do some birdwatching."

"Oh, no, no, no! You have to go to Lovers Key! It is one of the best birding areas in Southwest Florida." I tell him. "It's a very short drive; we can even rent bicycles and ride there."

"We? Tiffany... I need to tell you something."

Here it comes.

"I'm married."

"So where is your ring? And where is your wife while you're down here in Florida?"

This is excellent! If I can get him into bed, I know there will be no clingy goodbye. I won't have to worry about avoiding him. He'll either be so embarrassed by his infidelity that he will be the one avoiding contact, or he'll want to get as much of me as he can before he moves on. Either way, fine with me!

"My ring is on this chain," he says, pulling it up through the collar of his shirt. "In my work, I deal with live electrical circuits; jewelry is a big no-no. I guess I can start wearing it now. As for my wife, she had a work emergency come up. She's not the type that enjoys the beach anyway, she would have been miserable. In fact, I think she made up the whole work emergency story. That would be so much like her because she knows I'd be miserable if she were miserable."

"So she sacrificed a trip to sunny Florida just to let you be happy. She sounds like a great gal to me."

"She is," he said, looking down at his coffee mug.

"I sense a but," I whisper to him.

He looks up from his cup and into my eyes. He looks pained.

"She's worn down. Some would call her dull. She's been that way for a while. She's not at all like you. Used to be though."

I toss my head back and laugh. "Oh, my, Steve! There are very few women like me, and that's probably a good thing!"

He chuffs at that.

"In all honesty, I'm worn down as well. Neither of us is as adventurous as we once were."

"Well, I can't help her since she's not here, but I can help you. This parasail flight is a good step in that direction."

"I suppose you're right," he says softly.

"Excellent! So let's get started on the newly adventurous Steve. Shall we rent some bicycles at the office and ride to Lovers Key? It's less than three miles. Get your binoculars; I'll grab us some water and snacks. Let's meet back here when we're ready."

Less than fifteen minutes later, we're back on the deck. I take his hand, and we walk across the parking lot to the resort office. On the ride, we're both quiet. I'm not sure what's on his mind, but my actions are all that are on mine. There's something about this guy that hits me differently. Normally, I would have bedded him last night.

I've been thinking about that since we split after dinner and drinks at the tiki bar, yet I still haven't come up with a good answer for why I didn't. His behavior this morning might have been what I sensed last night. Like he said, he's worn down, and so is his wife. He had to have been adventurous when he was younger, based on the stories he told me about the places he'd traveled. And maybe stupid me thinks I can fix him.

Isn't that what women do--try to fix their men? But he's not my man, so if I fix him, she'll get the benefit. That's probably for the best anyway. He talked about her lovingly last night; they've been together for a long time. Oh, fuck, am I going soft? My pussy hums for him, and I'm thinking that maybe, just maybe, I'll be a good girl this once and not do my usual fuck him and forget him. Can I do that? Can Inot bed this guy? Do I have it in me? I guess I'll find out.

Less than thirty minutes later, we arrive at Lovers Key and spend a few hours birdwatching. Being close to him is all it takes to make me happy this morning and keep my kitty purring. Dammit, he's sexy. He's also kind and considerate. He's teaching me about birds! He's a dad, a DILF. Several times our faces are close, within kissing distance. He seems interested. Just ask, Steve! But he doesn't. I've never been so frustrated! My kitty is so wet that I want to scream, "Fuck me, Steve!" But I don't. Aaauuuggghh!

We wrap up the birdwatching and arrive back at the Outrigger in plenty of time to get to our parasailing reservation. Steve drives; he has a Camry; of course he does. As we board the boat and head out, he seems nervous. He's full of questions as the crew hooks us up and goes through their safety checks and preflight briefing. When our feet leave the platform, he tenses and grabs my hand.

"It's okay, just relax," I coo, squeezing his hand.

He looks at me with a nervous smile. I'm not sure that he's breathing.

"Relax," I say in a more demanding tone.

He finally relaxes...until he looks down.

"Oh, fuck!" he exclaims. "Fuck, fuck, fuck!"

"Look at the horizon," I calmly instruct him.

His eyes clamp shut, and his grip on my poor hand tightens. The safety monitor on the boat seems concerned, so I signal that we're okay.

"Steve, CHILL!" I growl through clenched teeth.

He finally comes around, getting his wits about him.

"We are fine. Everything is going normally. Take deep breaths and look at the horizon," I say in my best calming voice.

He starts to relax and finally smiles again. As the minutes go by, he relaxes further. Soon he's actually enjoying himself! Before our flight is over, he's giggling like a schoolgirl and yelling along with me. I think I've discovered the adventurous Steve that had been buried by dull. As the boat slows and we are reeled in, he turns to me with a huge smile on his face and tears running down his cheeks.

"Thank you, Tiffany," he says as he squeezes my hand gently this time.

"You're welcome; I'm glad you enjoyed it."

"You've helped me rediscover the old Steve."

"Good, dull Steve was okay, but I think I like the old Steve better."

We grab a quick bite at one of the restaurants just across the bridge and then head back toward the Outrigger.

"Sundown is about an hour from now; do you know any other good birding areas?" he asks

"In fact, I do! Turn left on Bay Road; it's just ahead."

That will take us to Matanzas Pass Preserve, a natural area with walking trails. It's marsh-like, so most of the trails are actually boardwalks. We park at the entrance; there are only a few cars in the lot at this time of day. I grab a map at the kiosk, and I take his hand as we enter the park. It's not long before he's in dad mode, pointing out birds and sharing his binoculars so I can see them up close. Parasailing with him and giving him that experience was a blast, but birding with him is when I can see the true man. He's not mentioned kids, but if he has them, then I'm sure they love him dearly.

It's been a while since we've seen anyone else, and they were all heading toward the park entrance. It's quiet here, just us and the birds. We stop again, and he leans on the railing, searching for the bird he hears. I lean forward too, being his extra set of eyes to help locate where the pretty little song is coming from. Suddenly, he catches sight of the bird and leans close to me, silently pointing into the brush. I see it. I also see him looking at me. He's so close. Kissably close. I decide that if he's not going to make a move on me, then I'll make a move on him. That's what I'd normally do.

"You want to kiss me, don't you?" I ask.

He looks at me, hesitant to admit that I am right.

"It's okay. I want you to."

"I shouldn't," he finally responds.

"Then don't," I reply, looking deep into his eyes. "But if you do, I'm afraid that one kiss won't be enough to quench the fire."

He raises one eyebrow and looks at me quizzically. I find it so cute, but is he truly so clueless?

"The fire between my legs."

"Oh!"

"I'm hot for you, Steve. And I think you're hot for me."

"I--, we--, uh."

"I promise that you'll enjoy it. You said yourself that I'm nothing like your wife. Or maybe I am. Maybe I'm like your wife used to be."

He looks at me and heaves a huge sigh.

"When was the last time you put this in anyone other than your wife?" I ask, stepping close and gently grasping his cock. It's hard.

"Oh, Tif--."

He loses his voice when I tug on his manhood.

"Of course, I can simply take you in my mouth."

I tug on the knotted drawstring of his shorts and kneel on the boardwalk. As I pull them down and take out his cock, I moan.

"Oh ffuu...uuck, that's a nice cock."

I dance my fingertips over him, and he sucks in a stuttering breath.

"Thank you," he sighs.

I lean in and kiss his crown. He's cut, so it's fully exposed, and wow, it is leaking with excitement. He's average, which is perfectly fine with me. He's also natural; there's no shaving or waxing for him. I run my tongue up the underside of his shaft, from his hairy nut sack to the rim of his crown. When I engulf the head, his knees buckle, and he supports himself with his elbows on the handrail. I drive my nose into his mass of hair and moan with his head at the back of my throat.

"Oh, god," he groans, "it's been a while."

My lips form a smile as I slide them up and down the length of him. I figured as much. Wifey has been neglecting him. I want to tell him that it'll be okay; Tiffany will please him, but I have a mouthful of him right now. Based on his reaction, I'm confident that I'll be getting laid tonight.

"Tiffany, I...not here. Someone might see us!" he whisper-yells.

"Then take me back to your room and have your way with me. You don't have to worry about me getting clingy. I know you're married, and I won't do anything to jeopardize that. We can just have a night of sex and then never see each other again."

"That sounds amazing," he groans as I wrap my lips around his shaft again.

"Who knows, maybe my real name isn't Tiffany?" I wink as I stand up and start to walk away, shaking my ass at him.

He fumbles with his shorts and then races to catch up to me.

"Your name's not Tiffany?" he asks.

"It's what I asked you to call me. Besides, does my name matter? My pussy has been wet for you all day, and I need to get fucked." I pause and look at him. "You can be the one to fuck me, or I'll pick another guy at the tiki bar."

We exit the park, and he's quick to get us on the road to the Outrigger. It's less than three miles away, but traffic is heavy, and the damn console in this car is too large. Instead of rubbing his cock, I reach my fingers up the leg of my shorts and swipe them in between my lips. Fuck, I'm wet and hot! He keeps glancing at what I'm doing. Traffic is slow enough that even if we bump into the car ahead of us, the accident won't cause any damage. I get my fingers good and wet, then raise them to his mouth. His lips part and his eyes grow large. He greedily sucks my fingers in.