I never imagined this moment, kneeling in front of his exposed cock. My large, firm, naked tits brushed the inside of his legs as I moved in closer. I was going to devour him in a way beyond what he had ever experienced. I was determined. It was going to be the greatest moment his cock would ever experience between two lips.

But wait, I am getting ahead of myself. This only makes sense by setting up the moment with how we found ourselves there – with twists I never saw coming. The events in this story are absolutely true and actually happened.

~~~

“Fuck, I love this!” I said to myself, not realizing the others around me could hear.

A warm, summer, Caribbean breeze blew across the bow of the ferryboat, as it launched from St. Thomas island to make the six-and-a-half-mile journey to St. John, its prettier Virgin sister. Mild waves splashed against the boat, creating a light showering mist. Without an airport on St. John, ferries from St. Thomas are the only way to get to the island. Something magical happens in my soul every time we board the ferry and begin the journey, anticipating being delivered and left on the remote, tropical paradise for the next two weeks.

Michelle, the middle of us three sisters, laughed in response. She felt the same giddiness for this annual trip. This year, my mom, two sisters, and I were joined by seven others. As usual, we rented a villa on the beach that would become our shared home for the next fourteen days.

There is no place I love more than the escape of a tropical beach. I love the feel of the heat of the sun’s rays and the breath of warm breezes on my body. Tropical humidity moistens my skin. The rhythmic, repeating sound of waves crashing before rolling in to lap the shore recalibrates my soul. My toes instinctively bury themselves into the heated sand, like hermit crabs burrowing for home. All the cares and worries of my normal mid-western life melt away as if they never existed. It is my happy place.

I enjoy this most with my family. My sisters and I are best of friends, and love having fun together. We spend a lot of time with each other, especially on holidays and vacations. My mom, sisters and I travel for an island vacation almost every year, around my birthday. It is usually the four of us, sometimes with extended family. We rent a house and all chip in. We are usually there for two weeks.

 My sisters and I all share good health and beauty genetics with our mom. We also take care of ourselves, including regularly working out. We’ve all been told we look ten years younger than our actual age, which is fine with us. Melissa is a young in her early forties, Michelle is in her late thirties, and I’m the youngest, just over thirty. There is no mistaking us as sisters, with similar 5’8” height, shoulder-length, light brunette hair, glistening, devilish blue-green eyes and bright smiles. We also share similar fit bodies with nice asses. I am slightly more endowed than Melissa and Michelle with 34D tits.

This year, we decided to return to St. John, our favorite of the Virgin Islands, in the Caribbean. It is the most pristine of the islands, with its white sand beaches, warm water and a variety of things to do. This year my mom, sisters and I were joined by Melissa’s husband Greg, their two sons, Michelle’s daughter, an aunt, uncle and cousin. It was kind of a full house. It was an amazing time together. I was in my happy place. Yet, one afternoon and evening were especially – memorable.

Like other trips with my sister’s husband Greg along, it’s not unusual to catch them sneaking a fuck in when they can. It’s not easy for them with a crowded house, not to mention their two sons around. For example, when everyone is at the beach, they will often ask one of us to watch the boys while they run up to the house for a few minutes “to take care of something.” They often sneak touches when they think no one is looking. Needless to say, they have a very active sex life.

The first ten days of the trip were everything we expected and more. All cares of the world were lost to the relaxed joys of snorkeling, hiking, shopping, bar hopping and sitting by the pool at the rental. Our family is very close, making vacations like this comfortable and fun. There isn’t anything we don’t talk or joke about with each other. We love to play, tease and joke around, with few limits. There is an ease to our time together.

After a night of barhopping, I woke up feeling especially hung over. I decided it would be a good day to relax and lie low. There were no plans. I rolled out of bed and threw on my usual multi-colored, pastel-striped bikini, a loose tank top with large armholes, and small jean cut-offs. It was already mid-morning. The hot sun was climbing in the sky.

“Hey there,” my middle sister Michelle said, greeting me with her usual enthusiasm. With her daughter on the trip, she didn’t have the luxury of sleeping in as easily as I did, being single.

I put my hand up with a smile. “Mornin'.”

“A little hungover?”

“Yeah,” I answered simply. “That obvious?”

“Last night was fun,” she affirmed.

“Coffee?” I asked, with a nod of agreement.

“A fresh pot in the kitchen,” she said.

“Perfect.”

I poured a cup and picked up a small lone pastry left in a tin on the kitchen counter. I sat down at a small table just off the kitchen and nursed the coffee, watching the house gradually come alive with activity. Cobwebs slowly cleared from my head with each sip of black coffee, while dipping in the small pastry.

It was a slower start, but the same wonderful cycle that made days on the island different from all other days. Each morning usually began still feeling some of the aftermath of the night before. Each day held all kinds of possibilities, without any schedule or expectations. Drinks usually started with morning Mimosas or Bloody Marys, shifting in the afternoon to beers or other beverages, depending on the activities – or non-activities being enjoyed. Afternoons normally spilled over into evenings with dinner and evening entertainment. Night options together included playing games in the rental, going out on the beach, or bar-hopping. The fun usually lasts into the early morning hours before crashing in preparation for it all to start over again.

My body was familiar with the rhythm and was slowly moving toward its usual recovery, with the assistance of the second cup of coffee.

“Hey,” my older sister Melissa announced, appearing in the kitchen, behind the counter. She was wearing a brightly colored short sundress. Her brunette hair danced on her shoulders. Her husband Greg stood behind her, wearing a t-shirt, and I assumed his usual pair of gym shorts. The lower half of their bodies were hidden by the kitchen cabinets. His arms were wrapped around her waist affectionately. “We’re all going shopping. I’ve planned the whole day out. Want to join us?” Her enthusiasm and loudness of her voice were higher than necessary.

“Hmmm, that sounds tempting, but I’m tired,” I answered back softly. “I think I’m going to stay here today and relax.”

“You sure?” she asked, already knowing the answer. 

“Yes, thanks. You have fun. I’ll just hang here or at the beach.”

“I think I’ll hang back too,” Greg said into her ear, but loud enough for me to hear.

“Now, that’s a shocker,” Melissa said, feigning a look of surprise. Greg’s dislike of going shopping with the girls is famous, especially on vacation. “All you needed was one person to open that door.”

Greg smiled with a look of relief, mouthing the word “thanks” to me.

“I was looking forward to our day together with the kids,” Melissa whined teasingly.

“How can I express my thanks?” Greg asked. His right arm moved, hinting that his hand was sliding down below her waist, hidden from me by the counter. He leaned his face in, kissing her cheek, and then down her neck.

Melissa’s mouth suddenly gaped. Her facial response and body language revealed what the cabinetry hid. Greg’s large hand found its target. His kisses caused cold chills to emerge on her shoulder and arms.

“I know exactly how,” she said. She looked again in my direction with a wink. “Excuse us. Greg has something he wants to take care of.”

They disappeared as quickly as they had appeared, this time moving toward their bedroom. I smiled at their playfulness as I continued to nurse my coffee.

Twenty minutes later, Greg and Melissa emerged again from their bedroom, stopping at the door. Melissa’s face had a satisfied glow about it. Her nipples noticeably pressed through the thin fabric of her colorful sundress. “Fuck, that was good,” she said to him with a smile, stopping to wipe the bottom of his lip with her index finger. She gave him a little peck as her other hand moved to the front of his gym shorts to quickly grope his already semi-hard cock.

Greg just smiled, furtively reciprocating with her ass under her short sundress.

I looked down quickly from the other room, pretending I hadn’t seen the show of affection.

Melissa announced to the house it was time to head out for the shopping excursion she had planned. The house emptied, and the door closed behind them. I could hear the car drive away, offering a quiet respite. It was nice having the place all to myself, with the exception of Greg being there. It was pretty much the same thing. Greg and Melissa had been married more than ten years, and with our family being so close, he’s almost like an older brother or cousin. We are very comfortable around each other, and able to talk about anything. 

Greg is in his mid-forties. Like Melissa, he takes pretty good care of himself, as much as he can working full time, and being a family man. He’s nice and tall, just over six feet tall, with slightly graying hair, a warm face and a decent semi-muscular dad-bod.

“How are you feeling?” Greg asked genuinely, as he walked back into the kitchen area.

“Pretty good,” I answered. “Coming out of the fog.”

Greg laughed. “Last night was fun,” he said.

“It was.”

“Any plans for the day?”

“Nope. Maybe watch a movie.”

“Me too. Let’s go watch something.”

“Sounds great.” I got up and followed him to the media room.

Scrolling through options, Caddyshack came up. “A classic,” Greg said.

“Perfect,” I answered, genuinely.

We settled in on the couch, talking and laughing comfortably as we watched the movie. Our conversation covered the usual random topics like football, how the trip was going, our jobs, and if I had a serious boyfriend. As we watched the movie and talked, we polished off a couple of beers.

After the movie, Greg said, “I’m going to make lunch and grab another beer. Want something?”

“Sure, sounds good.”

We went to the kitchen, where Greg made a light lunch for both of us. We continued to talk and joke with each other.

“What do you want to do now?” he asked.

“I’m easy,” I replied. “How about a game?” Our family was big on playing games together. Suggesting it seemed like a natural, easy option. We are also known for our playful competitiveness.

“Great idea,” he said. “You pick it, and I’ll beat you.”

I slapped him on the arm. “Fuck you,” I said with a laugh. “There’s no way." 

The playful, verbal sparring continued as we called out different game options. Unfortunately, we realized most of the typical board and card games are boring with just two people.

“It has to be something good,” I said.

“How about truth or dare?” he volleyed.

The air suddenly thickened between us, from his suggestion. 

Normally, the proposal would be awkward for most people with those who are related. Even in our family, with being so comfortable with each other, it was not something we’d ever done. The beers had greased the wheels of inhibition and loosened the restraints of better judgment.

My mind raced through the relational calculations, as best as it could. I knew there would be boundaries to what would be expected. I mean, he is my sister’s husband. Those boundaries could make the game fun. I’ve also never been one to turn down a challenge. I was the one who said the game had to be good. “You’re on,” I said.

Greg smiled. “It’s decided.”

We took our beers and sandwiches back down to the media room. We started another movie to watch as we played. I looked at Greg a little differently as we sat down. He was wearing his t-shirt and gym shorts.

The game began with mostly softball questions and dares, that gradually escalated. The first questions were simple starters like:

“Who is your favorite in-law?”

“What is your favorite place to vacation?”

“What do you want your last meal to be?”

Dares began to enter the game with simple tasks, like:

“Do a handstand.”

“Shotgun a beer.”

“Run to the pool and belly flop, then come back.”

As we played, the questions and tasks became more personal. Every intensified question or riskier dare gave permission to reciprocate the escalation, requiring something more of the other. The drinks loosened our inhibitions further. The questions became more sexual in nature:

“What’s the first place you had sex?”

“What’s the biggest age difference you’ve had with a partner?”

“What’s your favorite thing Melissa does when you’re having sex?”

The dares did too:

“Recreate your O face.”

“Eat a banana in the sexiest way possible.”

“Sit topless for the next ten minutes.”

I reached back and unclasped my bikini top before pulling the shoulder straps forward, allowing my top to fall from my tits in front of me. Greg reached out his hand, and I tossed the small bikini top toward him. He put it out of reach.

The game reached a new level of intensity. I sat there, exposed to him. Do I reciprocate? Do I make my sister’s husband pull his cock out? My mind raced as we played a few more rounds. It was his turn to require a truth, or to take the dares to another level.

“Your turn,” I said.

“Truth or dare?” he asked.

I took another sip of beer. “Dare.”

“Suck my cock.”

“What?” I asked out loud.

“Suck my cock,” he repeated.

Greg already knew I liked to suck cock. It was no secret that his wife liked to as well. “You’re serious.”

Greg smiled. “Yes. I want to see if you’re as skilled as Melissa. If you don’t think you are, that’s OK. You can just lose or I can give you a different dare.”

He threw down the challenge, knowing it was as irresistible as it was unexpected. He crossed a boundary in a way that put the ball in my court. Yet, he also knew my competitiveness. He knew my inhibitions were down. My mind raced, anticipating any long-term consequences if I accepted the dare. “OK,” I said reluctantly, “on two conditions.”

“What are they?”

“Melissa can never know about it. This must always stay between us.”

“O.K.,” Greg said, surprising me a little. “I promise I will never bring it up to her. What’s the second condition?”

“This is a onetime thing. One time.”

“It will need to be good then,” Greg answered jokingly.

I cocked my head at the tease.

“But, deal,” Greg quickly added in agreement. “One time.”

Without saying anything more, I moved off the couch and onto my knees. I reached up and pulled his gym shorts down his long legs until they fell at his feet. I pulled them off and set them aside. I never back away from a sincere challenge. It was one thing for him to raise the intensity of the game with this dare. It was another to say he wanted to see if I was as good as Melissa.

I'd never imagined this moment, kneeling in front of his exposed cock. My large, firm, naked tits brushed the inside of his legs as I moved in closer. I was going to devour him in a way beyond what he had ever experienced. I was determined. It was going to be the greatest moment his cock would ever experience between two lips.

I licked my lips as I reached up and took his soft cock in my petite right hand and cupped his balls in the other. I leaned forward and kissed the tip of his cock before taking its entirety in my warm, moist mouth.

Greg moaned.

My tongue licked the soft skin of the captured snake, stirring it to life. I looked up at him, locking my wide eyes onto his. His cock instantly began to grow in my mouth. My tongue moved purposely over the surface of his expanding manhood until I could no longer contain its length.

“Mmm,” I smiled as my lips slowly pulled off its length, continuing my locked gaze on his eyes. I fondled his balls in my left hand. My mouth returned to work his firm, mushroomed head. My tongue emerged to lick and swirl around it, much like savoring soft serve ice cream. After circling it a few times, I let my tongue travel the length of his shaft to moisten it before returning to the sensitivity of his head.

Greg moaned again. I could tell he realized the determined look in my eyes. He could already tell this was going to be good, likely rivaling any other, including the masterful skill of my sister.

I took his head between my lips and sucked it in, just enough to capture it at the rim. My tongue circled it purposefully several times before pulling off with a popping sound. I did it again.

“Oh fuck,” Greg moaned. His large hands grabbed at the cushion of the couch.

Hearing the favorable response, I repeated the move four or five times before gradually taking the entire length of his cock into my mouth. I maintained the suction of my lips around his hardened cock the entire time....