Encounter at the Outrigger Resort

"It's my last night here," he says.

"It is." I agree.

"I need to get an early start."

"Probably wise."

"I don't suppose..."

"Then don't suppose. Just ask," I chuckle.

"Yeah, right," he says, glancing up at the door to his room. "It's been forever since I asked a woman to sleep with me."

"Yeah, I kinda stole that option from you yesterday."

I find this so freaking adorable. He gave me a pounding last night that left me sore, and today? Today he's bashful about asking if I want to have sex again.

"So...would you like to come up to my room?"

"I would. I need to drop these bags in mine first."

"Yeah, good idea."

"And I need to freshen up."

"Okay, so..."

"Gimme thirty minutes."

"Yeah, great! I mean, that's good. I'll see you then."

I give him a peck on the cheek and bounce off toward my room. When I reach my door, I look back. He's still standing by his car, watching me. I give him a finger wave and disappear inside. I drop my bags on the bed and strip down. I need to take a quick shower. Thirty minutes should be just enough time. I have to wash off the sheen of sweat and grit from our day outside. I'm ready with five minutes to spare.

When I exit my room I see him standing outside his. He looks freshly showered and is holding a glass of white wine. He watches me, smiling, as I make my way across the parking lot and up the stairs to his floor. As I approach him, I tell him that he'd better have a glass for me. He turns around and produces a glass that has been sitting on his air conditioner. I take it from him and melt against him for a kiss.

"Two things about tonight that you need to know. First, I'm in control, you made me sore, and second, I'm not spending the night, I hate long goodbyes," I tell him after a passionate kiss and a sip of wine.

"Fine, shall we stand here and make out, or take this party inside?"

"Well, if we stay out here we run the risk of being arrested for public indecency," I offer.

"Thought you are all about risky behavior."

"Things that might injure or kill me, not things that will get me thrown in jail."

"Well, that settles it, let's move this party inside."

I turn and walk through the open door. He follows me, unaware that I'm naked underneath the sundress I'm wearing. The thought of pulling it over my head and tossing it to the floor briefly crosses my mind, but that would make it too easy for him. We sit on the sofa and chat. His eyes roam over my body. I slip off my espadrille heels and turn toward him, placing my feet in his lap. I have to be careful to keep my knees together. I don't want my secret revealed too soon. He takes the hint and caresses my feet. He's trying to be witty, something about his travels, so I laugh a flirty laugh.

"This is a pretty dress you're wearing, Tiffany."

"Thank you."

He leans toward me and uses his free hand to reach toward the elastic at the top of the dress.

"I sense that you are harboring a surprise here. May I?"

I nod and he hooks a finger in the elastic, pulling the top of my dress down until my nipples are showing.

"My suspicions are correct."

He runs his fingers over my nipples, which were already hard but now feel as if they'll break if touched. I gasp softly as he takes one between his thumb and forefinger, then moves to the other. Back and forth he teases them. Then he stops and leans back.

"You have such pretty nipples."

"Pretty enough to kiss?"

"Mmm, later. I have a sneaky suspicion that you're not wearing panties either."

"There's only one way to find out," I grin behind my wine glass.

He slides a hand from my shin, up my leg, and under my dress. I part my thighs, and he reaches for my sex. Of course, I'm not wearing panties, silly man!

"Oh my! I was right! Sweet Tiffany, you're such a naughty girl."

"You're the one who invited me up to your room for sex. Am I here under false pretenses? Are you going to proselytize to me? Try to convince me to change my wicked ways?"

"Oh no, not at all. I intend to take advantage of your wickedness."

"Good." I purr and arch my back as his fingers find their way between my wet lips.

"Take off your dress."

"Excuse me? Are you telling me or are you asking?"

"I'm telling."

"Who did I say was in charge tonight?"

"You can be in charge of the sex, but this is foreplay. Take off your dress."

Okay, I kinda like this dominant behavior. Usually, my conquests are back on their heels from the beginning because I come on so strong. Of course, I usually don't spend the night with them, let alone spend two whole days. I stand and move around the table. It's between us now. I pull the top of my dress down to near my navel, fully exposing my breasts.

"So you like these?" I ask as I run my hands over them and pinch my nipples.

"Very much."

"Later, when we're actually having sex, you're going to kiss and suck them. That's not a request."

"Yes, ma'am."

I fondle myself a bit longer and then slip the dress off and toss it at him.

"And you're going to put your tongue between my lips. Again, not a request," I say as I slide a hand between my legs.

"Okay."

"And then I'm going to mount up and ride you off the edge of a cliff while you suck my titties and squeeze my ass."

"Yee Haw."

"And when we're all done, I'm going to leave a trail of your seed across the parking lot."

"That'll leave a stain. But enough of this, come sit again and let me play with you."

I return to the sofa and recline against the arm with my bottom shifted close to him. One leg is on his lap, the other behind his head. I'm spread for his and my enjoyment. He kisses the inside of my knee that's near his head while one hand roams up my other thigh. His fingers come to rest between my lips.

"Be gentle," I whisper.

He smiles and nips at my inner thigh while a finger enters my sopping-wet hole. Fuck yes! That's it, gentle, oh so good. His thumb finds my clit and softly strokes it. In no time my breathing speeds and I'm nearing an orgasm. And then he stops!

"What the fuck, Steve! I was going to cum for you!"

He sticks his wet finger in his mouth and moans as he sucks on it.

"I think you should cum for you."

"What?"

"I want to watch you touch yourself until you cum."

"Is this how you treat all your women? Tease them and make them finish themselves?

"I might...if I had sex with other women," he says, looking a bit crushed.

"Oh, fuck, Steve! I'm sorry. I didn't mean it that way! I was just being flirty. Please, I'm sorry."

Now I've broken the mood. Fuck! Here's this great guy, who hasn't had sex in years, whose wife doesn't take care of him, and I go implying that he's some gigolo. Great Tiff, just fucking great.

"Here, Steve, look. You want me to touch myself? Watch me cum? I'll do anything for you. Anything you want. Tiffany is here to satisfy you."

I start masturbating for him. Slow and gentle. Soon he's entranced by the way my fingers tickle and glide across my pussy, and how they pinch and dance across my nipples. In a few minutes, I'm nearing my release. I speed the attention to my pussy and moan as I spasm with him sitting so close between my legs. Fuck this is hot, having him watch me please myself while I'm totally naked and he's fully dressed. He begins to kiss his way down my inner thigh, so I spread my lips for him. Reaching my still-quivering pussy, he inhales deeply. A low rumble rises in his throat, and he flattens his tongue against me before taking a slow lick.

"I've missed the taste of a woman," he says into my sex.

One finger slowly slips between my lips, gently invading me. I moan my pleasure.

"May I try two?" he asks.

"Gently."

Another finger joins the first. He's being quite careful not to cause pain.

"Good?" he asks, once both fingers are buried inside.

"Good."

He begins to suckle my clit while slipping his fingers in and out. I sigh deeply. He moves his lips and tongue lower, licking around his fingers and rubbing my clit with his nose. The pressure is perfection.

"Yes," I moan.

"Yes?"

"I'm going to cum again."

"You cum a lot."

"You make me cum a lot," I giggle.

"I could stop."

"Don't you dare stop now!"

I moan my release as my hips spasm against his face and my core squeezes his fingers. It's not the orgasm that I need, but it does for now. I moan in post-orgasmic bliss, and he smiles up at me from between my legs. He withdraws his fingers and kisses my lips. I have to wonder what happened that ended with him and his wife growing apart, because this man is a skilled lover. If he were mine I'd make love to him daily. He's not yours, Tiff! I remind myself. He'll never be yours. You're a fuck 'em and forget 'em girl!

He retrieves a bottle of water from the refrigerator. How considerate. He twists off the top and hands it to me. I drink half of it in rapid gulps while he stands there laughing at me.

"One of us is inadequately undressed for what I have planned," I smile up at him

"So, I should match your level of undressedness?" he chuckles.

"Indubidably."

"You're an enigma, Tiff."

"True, but I have a sex drive that men love."

"I'll give you that. Have you always?"

"Had a high sex drive? Yes. Lost my virginity at fifteen. Fell in love with the feeling of a good stiffy inside me. Eventually, I learned to enjoy the taste of a man's seed."

"So you truly are the slut I picked up at the bar."

"Actually, I was the one pursuing. When I saw you on the beach, you intrigued me. Meeting at the bar was just a pleasant happenstance. I would have found you eventually."

"So I'm the slut?"

"No, I'm the slut. But tonight, I'm your slut, and I'm going to ride you if you'll just stop flapping your lips and get naked!"

He chuffs and rubs his forehead, muttering, "What have I gotten myself into?"

"You've gotten yourself into another damn fine orgasm if you'll just get naked!"

He undresses and I stand to wrap him in my arms. Our lips meet, and I grasp his ass, pulling his erection against my stomach. He's leaking and has been leaking based on the wet spot in his underwear. Our tongues dance for a few moments before I break the kiss.

"Wait here," I say as I press a hand to his chest.

I gather a towel from the bathroom and lay it on the sofa cushion.

"Sit," I say, pointing at the towel.

Once he's sitting, I straddle his hips and drag my wet lips up and down his shaft. He grows harder, no doubt eager for the penetration he knows is coming. I want this; want it so badly. But at the same time, I'm loathe to take him inside me. I know this will be, has to be, our last time. He's leaving tomorrow. We both have lives to return to, and he has a wife. As I look deeply into his eyes, I have to wonder whether our time will change things between them. If so, I can only hope it's a change for the better. Right now, I know what I need, what he needs. One more mind-blowing orgasm. He deserves it. After years without feeling a woman wrapped around him, he deserves one more great cum. Hell, it might be the last time he spills himself inside one. Like I said, I'm going to ride him over a cliff, but maybe we should go for a leisurely ride first.

"I need to feel you inside me," I whisper.

"You're in control."

I smile and wrap my hand around him, guiding him to my entrance. We both moan and our eyes roll back as I take him inside for the last time. There's a slight discomfort as he stretches me open, but it's just a pleasant burn, nothing that's going to deter me from my plan. I rise up and down on his shaft, coating him with my excitement. The burn fades, and I'm left with that feeling of having a good dick inside me. The feeling I love so much. I sit on him, rocking my pelvis as I fondle my breasts.

"You're going to kiss and suck them," I tell him as I place one nipple against his lips.

He eagerly laves my hard nub and then takes it between his lips. His mustache tickles my areola. I place my hands on his shoulders, close my eyes, and drop my chin. I'm focusing on the sensations his lips, tongue, and cock are creating. I don't recall ever enjoying a man this much. Of course, I've never enjoyed the same man this many times. Maybe I need to stop jumping from cock to cock. Take time to enjoy a few. Naw, what is it they say? Variety is the spice of life, and I like my life spicy!

"I want this time to last," I whisper.

"So do I."

"This feels so good."

"You're so wet."

"You're so hard."

"Oh god, I don't want this to end, Tiff."

"It has to. We are going to cum together one more time."

The rocking of my hips stirs his shaft inside me. Damn, it feels amazing.

"Thank you. Thank you for reminding me how amazing sex can be."

"Mmm, it's been a real pleasure."

"I'm going to miss this so much."

"Go home and remind your wife what it feels like to have your cock inside her."

"I don't think she cares anymore."

"She will after the first time. You are an incredible lover, Steve. Put your lips on her, remind her what it's like to feel your tongue between her lips."

"You think?"

I nod as I chew on my lip. I'm so close to cumming, but I want it to last. I ache to feel his cock throb inside me, but I also know I'll regret it. It will mean the end of some of the best sex I've had in a long time. I slow my hips.

"I know. Go home and make love to her."

"Oh god, Tiff. All I want is to be with you, make love to you."

"There's no room for that in my life, Steve."

But I wish there were.

"I wish--"

"No, you don't. You have a good life with her. It doesn't have to be dull. Don't let it."

"Oh, Tiffany. I'm so close."

"Let go, cum with me."

I rock my hips faster and pull his lips back to my tits. I am close--so close.

"I'm cumming," he gasps.

"That's it, stud. Cum in me. Put your hot seed deep in Tiffany's wet cunt. C'mon, do it."

"Oh, fuuuuck," he groans.

I feel him grow inside me, and then he throbs. The sensation pushes me over the edge. Rather than rocking, my hips are now jerking. I'm out of control now, cumming so hard. I keen briefly before I can't make another sound. My mouth hangs open in a silent scream. I thrust against him twice more, then collapse.

We're both panting and covered in a sheen of sweat. My heart is racing, and I'm sure that his races just like mine. As we sit in a sweaty embrace, his flaccid cock slips from me. I feel a glob of his discharge escape. After a few minutes, I rise off him. He stays seated, watching me. I walk to the refrigerator and grab two bottles of water, opening one for me and handing him the other. I reach for my dress and slip it over my head. I feel traces of him slowly trickle down my legs. I slip into my shoes and stand across the table from him.

"It's been fun."

"Definitely."

"Go home and love your wife."

"I'll never forget you, Tiffany."

"Or whatever my name is."

"Yeah."

"Goodbye, Steve."

I walk out the door. When I reach my room, I look across the lot and see him standing in his doorway; his flaccid cock hangs between his legs. I close the door, shutting out him and the last two days. I kick off my shoes, peel off my dress, and step under the cold spray of my shower, and I cry.

I never cry over a conquest, but Steve was different. He was part incredible lover, part father figure, and always considerate and respectful. I never get to know a conquest like I came to know him. This hurts. I vow to never do this again. Wham, bam, and gone--that's me.

Thank you for reading my story. Some of the locations mentioned did or do exist. For example, the Outrigger Beach Resort was a long-time fixture on the south end of Fort Myers Beach, Florida. It was wiped out by Hurricane Ian in 2022. Other locations mentioned in the area may or may not exist today.

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