The small rugged open-air jeep bounced down the dirt path, jostled back and forth by the rocks under a thick canopy of the remote Costa Rican rainforest. José was doing his best to keep up with Cliff in the jeep ahead. The moist summer air was as thick as the foliage. My skin was moist, mostly uncovered wearing only the tiny black bikini top and a short jeans skirt Cliff gave me. I did my best to hold on, grabbing the side of the jeep with one hand, and having no choice, the muscular leg of Lee with the other. He reciprocated, not to stabilize himself, but to take advantage of my naked leg pressed against his. My tiny skirt was hiked up from sitting down, offering glimpses of my bare pussy beneath. Lee’s thick fingers strategically moved up my leg with each bounce of the jeep, as if pretending the bounces of the vehicle were causing it. I looked down to see his pinky finger dangerously close to my still-wet pussy, and glanced over to see his cock straining the front of his shorts. It confirmed my suspicion.
My small 5’6” athletic frame was squeezed next to Lee in the back of the jeep. My shoulder-length blond hair blew in the wind behind me. Cliff’s words rang in my ears, “Ashley, you will do anything it takes to make them happy.”
Lee looked over at me the moment I glanced at his cock. I looked up at his eyes. He smiled devilishly. I offered a confident look. There was a brief awkward moment. I could tell he wondered what he could get away with. What would I allow? We had just met minutes before. He was a complete stranger, yet told by Cliff, I would do anything to make their stay pleasurable.
I only have myself to thank for being in this situation. A few months before, my friend Katie and I went to a wedding of another mutual friend. I bet her to see if she could get a stranger sitting at the bar to kiss her. She laughed it off and said she could get him to fuck her if she wanted. The bet was on, and she won. I told her she would need pictures to prove it. After the night, she found herself surrendered to him, partially due to the compromising pictures. She wasn’t complaining. He was by far the best sex she’d ever had, and that was saying something. The handsome mysterious stranger was Cliff.
Cliff offered Katie a proposition to win freedom of her willing obligation to him. It was a simple golf game, against me. If I won, she would be free; if he won, I would willingly agree to take her place: complete submission with no limits. Katie pushed that there was no pressure to the wager. I didn’t have to do it. She was secretly enjoying her submission to Cliff. She would understand if I felt unsure about my ability to win the golf match. She also knew I never back down from a competitive challenge. There was no way I would lose the game. Then I did.
Days later I received a text from Cliff telling me to pack for the tropics, bring my passport and be ready for his chauffeur Antonio to pick me up in an hour. Before I knew it, Cliff and I were on a private corporate jet to Costa Rica. The last two days have been strangely magical. My infamous strong will was melting like butter under the Latin sun. Cliff’s strong gentle confidence was addicting. The way he touched me was unlike anything I had ever experienced. And that cock. My stubborn competitiveness was turning in on itself. Rather than being determined to win for myself, I found myself strangely determined to be the prize he always dreamed of. I was willingly surrendering myself to him.
Now his clients and potential business partners had arrived. Cliff invited them to the all-expense-paid tropical paradise to work the deal and to do some team building that would be important for their future work together. He was determined to close this deal and have them leave with smiles on their faces. That was why he brought me.
Janice and Todd were a married couple from Tennessee. Janice was about my height and size but with brown hair. She had a warm down-to-earth smile. Todd was around 5’11” with an average build and dad bod. His light brown hair was receding, showing some balding up front, compensated with a mustache and beard shaved close. They were in the lead jeep with Cliff.
Matt and Lee were from Canada. Matt was about Todd’s height but looked closer to my age. He had dark hair and dark eyes. He was tan, fit and muscular. Lee was the oldest of the four, big. He had just retired as a firefighter. Despite being in his early 60s, he had a youthful demeanor that seemed always ready to play hard. He was easily the tallest of the guests, close to 6’3” with a big frame. His short greying blond hair was pushed up in front. He had a round jovial face and a big smile. His boisterous laugh and voice made it clear he was the life of the party in the firehouse. Matt sat in front of me in the front passenger seat of the jeep next to José. Lee was enjoying being crammed in the back seat next to me.
I looked back up at Lee’s face, and, with a sultry smile, moved my petite hand down his leg to the bulge in front of his shorts. It was hard to grab all of it through the material, but I gave him a firm squeeze. Lee gasped in surprise at my bold move that also gave him permission. His huge thick hand slid down my leg. The side of his pinky finger pressed into the length of my moist pussy. The bumpy movement of the jeep caused his finger to bounce up and down against my erect clit and the folds of my pussy.
José and Matt had no way to know what Lee was beginning to enjoy in the back of the Jeep. José’s eyes were on the road. I was sitting behind Matt, making it impossible for him to see what Lee was doing with his right hand.
With skill, I pulled down the zipper to Lee’s shorts and maneuvered my hand in to feel the massive pile of flesh packed beneath the fabric. Fuck he was big, I thought. I manhandled the hardening snake out of his shorts. I was stunned to see the monster I had just freed. Fuck!
I could tell Lee was pleasantly surprised by my bold response to his testing. I was too. Something triggered in me watching his wonder turn to glad surprise by my slutty sassiness. Deep down, I knew Cliff would be pleased too. I did my best to wrap my petite fingers around the girth of his cock. I palmed the head of his cock with my small strong hand, before gripping his cock again. The movement of the jeep provided a perfect rhythm to stroke him.
“Fuck!” he yelled.
Matt turned to look in response, thinking Lee was talking about the road. He wasn’t.
My pussy was getting wetter by Lee’s touch. In one quick smooth fireman’s move, Lee turned his body toward me, put his right hand on my left waist, reached his left hand over to my right waist and picked me up like a rag doll. He turned my body in the air and set me down on his lap, facing him. I reached above me and held on to the roll bar on the back of the small jeep. Lee’s hard cock pushed into the opening of my wet pussy, before burying his entire length into me.
I gasped. “Fuck!” I screamed. My skirt was hiked up, showing my ass to Matt, watching with envy from the front. My tits fell out of the small black string bikini top from the movement. They danced in front of Lee’s round face. I held on to the roll bar to keep from being thrown out of the jeep. My body bounced on top of Lee. God his cock felt good. His strong hands held my waist. His mouth savored my tits.
It didn’t take long before Lee’s body began to quiver beneath me. Thick cum poured from him into me. Feeling him under and in me brought me over the edge, soaking his long shaft. My body shook until I collapsed into his large frame. He held me tight as my body succumbed to the climax.
Just as easily as he had taken me, Lee picked me up and dropped me back into the seat next to him, like discarded trash. His cock still stood tall. My petite hand couldn’t resist stroking him softly, palming his head again.
Lee sat back with a vaunting satisfied grin. “This is going to be a good trip,” he said. Matt watched in desire before turning back around, wondering what might be in store for him.
After a couple of hours driving deeper into the remote jungle, we arrived at our base camp. There were three canvas yurts set up in a small clearing with a fire pit in the center. A picnic table with a stove and other supplies sat off to the side. It was remote and primitive. Rays of sunlight broke through the thick covering of trees. A creek flowed forty feet away. The air was thick with humidity. Sounds of toucans and other birds squawked from their perches high above, watching the intruders who had just invaded their piece of paradise.
We all poured out of the jeeps, eager to stretch after the long bumpy trip. I did my best to pull my short jean skirt down, and recover my tits under the tiny bikini top. Cliff smiled with approval. At his direction, Matt and Lee moved into the farthest yurt. Todd and Janice unloaded their bags into the middle one. “I’ll be in here,” he announced.
“Where will I be?” I asked.
“Depends,” he answered nonchalantly. “Wherever our guests want you.”
Shit, I thought to myself, realizing with new clarity why he'd brought me.
We didn’t stay at the base camp long. Cliff wasted no time making sure our first day in the jungle was filled with breathtaking adventures beyond anything I or our guests had ever experienced. Behind the yurts were six ATVs. We spent the day exploring the area, off-roading through the jungle, and hiking a nearby mountain. By late afternoon, we were all covered with mud and sweat. Cliff led us to a lagoon surrounded by thick dark green foliage. One end had a small beach, the other a cliff with a picturesque thirty-foot waterfall. It looked like a hidden paradise of storied legends.
“Time for a swim,” Cliff announced, as he stepped off his ATV. He boldly stripped off his clothes without any warning, showing off his tan sexy muscular body. “And there’s only one right way to get in this pool.” Cliff walked around to the top of the waterfall and jumped in. We all watched as he hurled his naked body off the cliff and into the water below. His head popped up in front of the waterfall. “Let’s go! Everyone, in the water! It feels amazing.” It was an order as much as an invitation.
Lee and Matt quickly followed suit, throwing their clothes off, climbing to the top of the waterfall and jumping in.
“Come on, Todd and Janice! The water’s great!” Lee yelled boisterously.
Janice looked nervously at Todd. She felt the peer pressure to strip in front of these men she’d just met that morning. I could tell she wondered what Todd wanted her to do. If she did take her clothes off and jump in the water, what else might happen?
“Come on, you three!” Matt yelled, cajoling us.
I looked over at Janice, giving a sheepish look as if I was feeling hesitant too. “I’ll do it if you do,” I said. “Let’s do it together.”
Janice’s nervous look on her face softened. She looked at Todd, and then again at me. I pulled my bikini top off my body, offering a smile.
Todd immediately pulled his shirt off too, almost to encourage Janice to go along. Janice looked at me, making a deeper connection. Whatever was about to happen, we would be in this together. There was strength in numbers, even though that number was two. Janice glanced back at Todd before pulling her shirt off over her head. We looked at each other’s bodies admiringly. We both knew the men were staring too.
“Let’s do this,” I said, pulling my skirt down. Janice and Todd both dropped their shorts at the same time. Todd’s cock was already growing, standing there naked with the two of us like a fantasy threesome.
The three of us ran to the top of the waterfall and jumped into the water. Despite the warm humid tropical climate, the water was cool and refreshing. The small lagoon gave plenty of space for us to spread out, but the group of skinny-dipping strangers stayed near each other. Janice at first tried her best to cover the view of her tits and body in the crystal-clear sapphire water. She stayed close to me and Todd. Our hands accidentally touched in the water. Our connection deepened. Not surprisingly, the clear water did nothing to hide the view the men’s naked bodies either, including the semi-hard cocks enjoying our naked presence with them in the fantastical tropical lagoon.
We stayed there for a couple of hours, openly taking in the magnificence of the place and secretly of each other. We swam, jumped off the ledge at the top of the waterfall and continued the easy conversation. As Cliff had hoped, the time at the lagoon raised the comfort level of the six strangers to new levels, like long-time friends.
We made our way back to basecamp just as the sun was setting over the western horizon. Everyone changed their clothes. Cliff had a small camouflage dress with spaghetti straps for me to wear. He was nice enough to include a pair of leather sandals, my perfect size. After dinner, the five of them sat around the campfire. I served drinks while the five of them casually focused on the details of their potential business venture. The day together greased the wheels of the negotiations. If the joint venture was finalized, it would be a significant risk for everyone, but the potential payoff was astronomical. They decided to sleep on it, and come to a decision the next day. Everyone retreated to their respective yurts. I followed Cliff into his yurt and began to take my dress off, anticipating enjoying the night in one another’s arms.