Caribbean Getaway

Caribbean Getaway

Special thanks to Regina for the inspiration to make a terrific story where I get to molest Reggie once more.

Let's start with introductions. My Name is Dan. I'm 38, married with two kids. I'm taking a long needed week's vacation by myself in the Caribbean at a five star resort which my company is paying for.

I love being solo at these places. Plenty of pussy that needs attention. Milf's are my speciality. It's how I recharge my batteries.

I consider myself a stud. Fact. Not being cocky. Just stating the truth. My cock is a very thick 8 inches. I know there's bigger, but it's not always about size. Many guys with big cocks can't even get it fully hard. Me, I can stay hard and fuck for hours. Ok maybe not hard for hours, but I have stamina and always good to go after a quick break. I'm insatiable.

When I'm on the hunt, I take what I want and give them what they desire. They are always deeply satisfied and go back to their husbands, dreaming about what I did to them, maybe feeling a little guilty. Their husbands never measure up after I'm done.

Now don't get me wrong. I don't force any woman unless that's one of their fantasies. Sometimes the husbands don't know about what's happening, other times they encourage it and even watch.

So here I am. Evening time at the resort. I have my eye on this milf dancing with her husband. I saw her earlier today on the beach. Boy, she filled out a bikini. I don't mean the skinny boney kind either. This woman had all the right curves, and she knew how to show em. She was every mans walking wet dream. I wonder if her husband knows how lucky he is. Nows she's wearing a LBD. She has dark caramel skin, maybe she's a local. I would put her at about 5'5". A brunette with a killer ass that just screams anal whore. Perfect size breasts, maybe a C cup. The kind of tits that bounce nicely when you're pounding them missionary or sway back and forth when you take them doggy. I bet her nipples can cut glass. The picture of a milf.

Just so you know. When I'm at home or at work, I'm a prefect gentleman. I treat people like gold. People love me. Not the case when I'm on the hunt away from home. Now it's time to move in. She's dancing with whom I assume is her husband. Not a bad-looking guy, I guess. A little taller than her. Full head of hair. Let's see how things play out.

"May I cut in?" I ask politely, but firmly. More insisting than anything.

He stammers a little. Surprised, I guess. "Sure. If it's ok with my wife?" he says.

She looks up at me with those beautiful brown eyes. I can see mischief in them, not to mention the slight grin across her lips. "Sure, I guess that would be ok," she says as her grin widens into a smile. Her husband steps away as I move in and take her hand.

We danced three slow songs, lucky timing for me and, of course, for her even if she didn't know it yet. I kept her close. Her nipples were soon protruding from her tight fitting dress. I worked my hands over her ass and copped a feel or her breasts when we were pressed together. I whispered into her ear some very naughty things before she said she needed to get back to her husband. Her name was Regina. Friends call her Reggie. She told me some things about her life. I didn't pay attention to most of what she said. I was looking down at her, smiling, pulling her close. She never said no. She never said stop. I took that as encouragement.

Before she stepped away, I placed her hand on my bulging crotch. My semi-rigid cock jumped at her touch. I knew she was impressed. I told her my room number. "10 o'clock sharp." She never said no. Just smiled and walked away. This one wanted it badly. I could smell her arousal. She was trying hard to restrain herself for her husband, who was sitting at the bar drinking and waiting patiently. Maybe she was just a good little wifey. Maybe she wouldn't show. Maybe he was getting the benefits of my work. It happens.

I went back to my room. Took a shower and put on some nice soft music, not too loud, and then I got a drink from the mini-bar and waited. At 10 sharp, a soft knock came on the door. I smiled to myself, knowing she would show, and yet again I picked the right one out of the crowd. Deep down they were all sluts, wanting to get ridden hard and put away wet.

A second soft knock came on the door, slightly louder this time. I opened it and invited her in. She was still wearing her LBD. "Hello Reggie," I said. "Nice of your to come. What bring's your here this time of night?" I asked.

Reggie smirked, and for a moment I saw contempt, or maybe it was doubt at having come to my room. "You invited me," she stated. Now smiling.

"Where's hubby?" I asked.

"Sleeping, passed out." She stated.

I grinned at her. "Lucky for us both, I guess. But you haven't answered my question. Why are you showing up in a stranger's room at night all alone?"

After a long pause, she moved close to me and ran her hand down the front of my shorts. My bulge was quite prominent at this point. She lowered the zipper and reached her hand inside, wrapping her fingers around my rapidly hardening cock. "I want this to come out and play. I felt it on the dance floor and it made we wet. My juices are running down my leg," she whispered.

At this point, I removed her hand and took a step back. "Show me," I smiled.

To my surprise, she went over and put the chain on the door.

"That's not necessary. No one else has the keycard," I stated.

"Oh, it's necessary alright. You're not going anywhere." she grinned mischievously. Then she pulled down the straps of her LBD, letting the dress drop to her feet. She had nothing else on. She was all woman with a beautifully trimmed dark bush, glistening wet with her juices. I was beginning to think that the roles were reversed. This woman was a tigress and I her prey.

Reggie started towards me and shoved me back onto the bed, quickly getting on top. Reaching down, she finished undoing my shorts and started to push them down. I quickly rolled her over onto to her back as she screeched with a laugh. "You brute," she cried.

I pulled my shirt over my head, tossing it aside. I then bent down and kissed her passionately. She bit my lip and laughed as I pulled back, then pushing me over, she grabbed my shorts, pulling them completely off. Now I was naked.

She climbed back on top of me, straddling my hips. Reaching down, she grabbed my rock hard cock. Smiling at me as she leaned back, she started rubbing it on her cunt lips. She lifted herself up and aimed the head of my cock at her pussy. She started rocking back slowly, moaning. "So big," she gasped as it popped into her love cannel.

My cock was now partially inside Reggies cunt. She was rocking back and forth, trying to fit it all in. She was so tight. Reggie moaned as she slowly worked my bare, hard cock inside her. As she leaned forward, I grabbed her tits. Sucking her golden brown nipples into my mouth, first one, then the other. Fuck, they tasted fine. I reached down with my hands and grabbed her hips. I pistoned myself up, burying the rest of my thick cock into her cunt, not wanting to wait any longer. She screamed out loud, "Ohhh yes, fuck meee." I'm sure someone had to have heard that.

I drove my cock into her several times before I needed to change positions. I rolled her over onto her back, her legs wrapped around me. My cock never left her drenched cunt. Now on her back, I had control. With her legs clenched around my hips, I simply power fucked her. She was moaning and gasping. As she writhed below me, I leaned down and took a nipple into my mouth, biting it and sucking on it as she grabbed my head.

She was getting close and so was I. Moving up from her breasts, I kissed her hard again on the mouth. She took my tongue into her mouth as we both exploded into orgasm at the same time. I never came so hard in my life as she moaned into my mouth. As I finished dumping my potent seed into her cunt, she slowly stopped writhing below me, her legs still wrapped around me, panting.

A few moments passed as we continued to kiss passionately. "That was amazing," she said. "The best fuck I've had in a long time." She gasped. "I hope you didn't just knock me up. I'm not on anything."

If the slut got knocked up, that was her problem. I'm sure there were a few rug rats running around carrying my genes.

"I aim to please," I said. "I'm not done yet either," I grinned.

I slowly pulled my slimy, semi-hard cock out of her pussy and then moved back and started kissing my way down her body. "What are you doing?" Reggie asked.

Squeezing both her ample tits with my hands, I worked my way down until I got to her cunt. It was drenched and gapping wide. Our combined juices leaking out. Savouring the tasty treat ahead, I started to lick her clit and suck all around her cunt, and then drove my tongue into her snatch. I then began to lick and suck on her pussy. I could taste us both, and it was divine. She tasted like honey. "Ohhh my god," she screamed as she grabbed my head and pulled me into her cunt. She exploded again, screaming "Fuck," as she came again. I lapped up more of her juices.

As Reggie came down from her second orgasm, I licked her gently, enjoying the taste and allowing her a brief reprieve.

I slowly crawled back up to her breasts, kissing everything as I went. My cock naturally just slid right back into her sopping wet snatch just as I kissed her deeply. It was like our bodies were communicating with one another.

After I thrust into her a few more times, Reggie asked for a break. "My pussy has taken a pounding and needs time to recover," she sighed.

"How about a shower together?" I grinned.

"Oh yes, that sounds like a great idea," she giggled as I pulled out of her molested cunt. My cock slimy with our combined juices.

I quickly followed her to the shower. Her ass looked especially inviting. I needed some of that. Now to see if she was up for it. My cock was already well lubed from our juices. Whores were meant for my cock, and this one was no exception.

As Reggie turned on the shower, I came up behind her, pushing her against the wall. I started kissing her neck and reached around to finger her pussy. "I own you now, Reggie," I whispered into her ear as I nibbled on it. She moaned.

"Put your hands on the shower wall and stick out your ass, slut," I commanded.

Reggie didn't hesitate for a moment. "Yes sir," she giggled.

If this woman had any limitations, I hadn't found them yet.

She quickly leaned over, her hands on the shower wall. The warm water cascaded down over her body as she spread her legs wide apart. Getting down on my knees, I spread her cheeks, driving my tongue into her tight little rosebud. I licked down to her cunt and then drove my index finger up to the knuckle. I worked it around, coating it in her juices. Licking back up to her rosebud, I slowly inserted my slippery finger into her ass. She moaned.

I worked it around until I thought she was good and ready.

I stood back up, grabbing my now rigid cock in my hand. She looked back at me, smiling mischievously. "You gonna stand there all night or are you gonna take what you want?" she smirked.

Gripping my cock, I guided it to her puckered rosebud and started to push in. Surprisingly, the large mushroom head of my cock popped in without much resistance. Our dear milf Reggie wasn't new to getting fucked in the ass. Knowing I had prepared her well, I was still surprised none the less.

With the head of my cock now inside Reggie's ass, I began working the rest into her. Its thick veins made it look even more menacing as I kept working it back and forth. Her butthole puckered in and out as I continued to defile her. Once I got it all in, I smacked her ass hard, leaving a red print. She yelped in surprise and then, looking back at me smiling, she said, "Is that all you got?"

"Well now. I take that as a challenge. You might be the biggest whore I've ever had the pleasure of fucking." I said, smiling.

Now that Reggie was accustomed to my size, I began to really work my cock. I grabbed her hips with both hands and started to pound her. Her ass rippled as I slammed into her. She moaned louder and louder and I saw that she now had one of her hands down and was rapidly rubbing her cunt.

Reggie was looking back at me, pure ecstasy on her face. Her eyes were opening and closing as I drove into her. Her breasts were swaying back and forth as I gave her everything I had. We did this for several minutes. I was getting close. Then, without warning, she came first. She drove her ass back into me as she continued to rub herself vigorously.

She cried out, "Oh fuck, I'm coming again. Don't stop, you bastard."

I pounded her for several more strokes when I announced, "My turn, slut, here it comes."

What happened next I didn't expect? She spun around and got down on her knees. "Fill my mouth, stud. Coat my tongue. Give it to your slut!" Reggie yelled.

Now, with my cock in my hand, I stroked it rapidly. I put it right up to her face. "Here it comes, whore. Take it all." I yelled.

The first large spurt of cum went right into her mouth. The second coated her tongue. I kept cumming, letting loose several large blasts. More coated her face, it dripped down her chin and landed on her breasts. By the time I was done, she could only open one eye and was using her fingers to scoop it into her mouth.

"So much," she stated. "You must have knocked me up with that first load you put into my pussy."

I was pretty worn out now. That woman can fuck. I helped her up to her feet and kissed her passionately. Getting back under the shower, we made out like lovers as we soaped each other up and cleaned up.

At the end of it all, as she was getting dressed, she thanked me for a wonderful experience.

As she moved out the door of my room. She turned and winked at me.

"Next time, bring some help," she said.

My mouth just dropped open. That is one hell of a woman. I thought as I crashed into bed.