All-Inclusive Vacation and Sex Ch. 01

As the plane approached the landing at the Caribbean Island airport, I quickly dismissed my disappointment with my former girlfriend Andrea. At the last minute she had bailed on me and I was headed to an all-inclusive resort vacation by myself. I didn't blame her for cancelling as the other guy she was seeing had put pressure on her not to go on the trip. I didn't lose any money as the resort was running a 2 for 1 special and I had booked her flight as refundable. At least it was not a couples resort and there was a chance that I might meet someone to my liking. If not, the diving was supposed to be great and I would take advantage of the lush coral reefs. Not in my wildest imagination would I have expected the sex filled week waiting for me on the island.

The plane landed and I made my way through customs and took the shuttle to the resort. I arrived on a Friday evening and planned to stay through the following Sunday. Some people arrived and departed on Friday, Saturday and Sunday. The shuttle arrived at the resort and after filling out some paperwork I was shown to my room. It was about 10:00 PM and I decided to have a nightcap at one of the bars. There was a DJ at the club but I was not in the mood for that so I located the piano bar. It was relaxing and a number of guests were decent singers. It was midnight when I finally turned in.

On Saturday morning after the buffet breakfast there was a resort orientation that was mandatory for all new guests to attend. An attractive island girl explained the amenities of the resort and laid out the entertainment schedule for each night. She explained the layout and the rules for the beach and swimming pools. There was a nude beach and swimming pool with a nude bar. She emphasized the importance of no public sex and that violators would be dismissed from the resort. On Sunday after breakfast there would be outfitters there to inform the guests about activities outside of the resort. Those activities were not covered under the all-inclusive cost but guests could deal directly with the outfitter.

I looked around at the other guests attending the orientation and saw mostly couples of all ages. There were a number of women traveling together but none that caught my eye although it was obvious they were checking me out. I noticed one couple with two teenage boys and I assumed that the boys were their sons. The wife looked to be in her early forties and was quite attractive and shapely however the husband was portly and out of shape.

After the orientation I walked around the resort and located all of the amenities and bars except I did not go on the nude beach. Lunch was also served buffet style and afterward I decided to hit the nude beach. I had never been on a nude beach before and I was curious and I hoped to shed my tan lines. I put on a pair of nylon shorts and flip flops; packed a tote bag with reading material and sun block and headed for the beach. I was proud of my 6'2" and 190 pound chiseled body. I had light brown hair, hazel eyes and kept my 28 year old body in good shape. I was also blessed with a nice cock that was 7+" long and a bit over 5" around.

That afternoon on the nude beach I got a lot of looks from girls, guys and couples. I sensed that there were also some gay couples at the resort that week. Every time I went to the bar to refresh my drink I could feel eyes on my body. I also did my share of people watching as a number of women looked good naked. They were all attached but still nice to look at. A number of women obviously had had boob jobs and they were flaunting their fake tits. They strutted around with their shoulders pulled back so that the firm tits stood out. Their husbands or boyfriends all had shit-eating grins as if to say eat your hearts out guys. I was never a boob guy as I had always been a leg and ass man. So I was more attracted to the women with curvy bottoms.

I spent the afternoon sunning, reading and enjoying frozen cocktails in addition to the people watching. Based on the calendar of events I had mentally planned out my week and determined that there was no reason to leave the resort. The Caribbean was calm and warm and I enjoyed swimming in it when I got too hot in the sun. That evening I returned to my room, showered and checked my body out in the mirror. I always picked up the sun fast and I was sure that my tan lines would be gone by the end of the week. I dressed in tropical slacks and a fitted shirt along with sandals and headed to the dining room for dinner.

The buffets were delicious as the food was plentiful and fresh. I enjoyed several glasses of wine with dinner and sat with two pleasant couples. They applauded my decision to come to the resort alone and enjoy my vacation. After dinner I went to the piano bar again and listened to guests sing their favorite songs as they passed the microphone around the bar. It was about 8:00 PM when I left the bar and decided to take a walk on the beach.

An hour later I returned to my room and on my way I heard a rustling sound coming from behind some tropical plants. I stopped walking and listened intently. Then I heard the sound again and some whispering too. My curiosity got the better of me and I checked out the area behind the plants. I moved quietly and peered into a small clearing. The two teenage boys who I had seen at the orientation were kissing and hugging each other. They were both very handsome boys but in fact upon closer inspection, I would have to say they were not handsome but pretty.

"I have to have you," one boy whispered.

I checked them out further. They were not only pretty but they had effeminate bodies and mannerisms. I couldn't help but look at the round asses in their tight khaki pants. I watched as they fished each other's cock out of their pants and stroked them as they kissed. Getting bolder they unbuckled their belts and dropped their pants and underwear down to their knees. They were indeed pretty boys with killer asses. They were both blonde with patches of blonde fuzzy pubic hair above their average six inch cocks. I guessed them both to be about 5'6" or 5'7" and weigh close to 160 pounds.

They continued to kiss and stroke each other's cock. Next they held each other by their buttocks and pressed their hard dicks together. By now my own cock was hard and I was thinking about fucking their sweet asses. It had been several years since the last time I fucked a pretty gay but I was not adverse to it especially being solo this week.

"You boys should be careful. Don't you remember what the girl said at orientation," I whispered to them.

Predictably they panicked and jumped back in surprise. They stared at me with their stiff dicks pointing out from under their shirts. "Why aren't you doing this in your room?"

"We can't. We are staying with my parents and they are in the room," one replied.

"But if you get caught they are going to throw you out. Then what would your parents say?"

"We didn't think we would get caught here."

"Well I caught you and your lucky it wasn't security. What are your names?"

"I'm Chris and my friend is Brent. I insisted on bringing him along because my parents wouldn't let me stay home alone."

"How old are you guys?"

"We're both 19."

"Do you guys want to come to my room and have some privacy?"

"Are you gay?" Brent asked.

"No but I guess you could say I am bi at times. I like getting blowjobs and fucking hot tight asses. Are you guys okay with that?" I asked.

"Maybe but we have to admit something. Chris and I have never made it with anyone else and we have never had a threesome before," Brent blushed as he spoke.

"I'm game if you guys are," I told them.

They looked at each other and then back to me and nodded their approval. They pulled up their clothes and redressed before stepping out from behind the plants. I led them to my room and I sensed their excitement. It wasn't what I had in mind when I thought that I might hook up with someone but hell they sure had sweet asses. We entered my room and I told them to relax as I handed them both a beer. They got comfortable in my room and then things got interesting.

"We need to ease into it. I want you to watch Brent and me make love first and then join in," Chris explained.

"Go for it," I said encouraging them.

Brent smiled and stood up from the sofa and I watched as Chris went about stripping Brent naked. He took his time and savored every moment of uncovering the effeminate body. He took Brent's shoes and socks off first and then he took off the shirt. He rubbed his hands all over Brent's chest and abs for several minutes and then he dropped to his knees in front of his lover. Chris unbuckled the belt, unzipped the fly and unbuttoned the pants. He slid Brent's pants all the way down to the ankles, lifting the feet one at a time to pull the pants free from his legs. Brent had a raging hard on and it was very obvious in his tight fitting underwear. Chris smiled when he saw the erection and hooked his fingers in the waistband of Brent's underwear and slowly tugged them down the shapely virtually hairless legs. I noticed that they were both breathing hard. My cock had hardened in my pants just from watching them.

Chris finally pulled Brent's underwear down past his cock allowing the elastic waistband to catch on the erect cock. He pulled the underwear slowly over the stiff cock and purposely let it snag in the elastic. He continued the downward movement and the rigid cock sprang free. Brent's cock bobbed in front of Chris's face but he was patient and finished removing his partner's underwear. Chris then reached up and caressed Brent's ass and thighs causing him to groan loudly. Brent looked as if he was in desperate need of relief. Chris then covered the twitching cock with his mouth and sucked it gently. Brent was so turned on that it only took a few sucks on his cock and he was ready to cum. Chris sensed this and stopped sucking him.

Brent looked confused but Chris spoke, "Let's take this to the bed. I want to be naked too," he said softly.

Chris walked over to the bed with Brent and I followed them. I watched Brent's ass as I walked behind him and I found myself wanting to fuck him. Chris took off all his clothes and told Brent to get in bed. Brent got in bed and lay on his back waiting for the next move. Chris took some lube from his pants pocket bag and then knelt between Brent's legs.

"You're look so beautiful that I just have to fuck you first," he announced.

Brent nodded in agreement and spread his legs. Chris fingered the taut asshole with one finger and then two fingers taking his time as he enjoyed playing with the lovely ass. He had Brent's asshole well lubed and then he added the lube to his own cock and moved into position. He lifted the legs up so that Brent's ass came off the bed and then he eased his cock into the anxious asshole. His cock slid in easily and I watched for the first time as two men fucked missionary style. Chris's arms were on the bed and the back of Brent's knees rested against them as he drilled the receptive ass. Brent's hard cock slapped against his abdomen as Chris fucked him. I then decided to take my own clothes off and join in when I felt it was appropriate.

"Oh my Brent, you are so hot. I can feel your warmth surrounding my cock. This is going to be a quick one," Chris gasped.

"Stay in me, cum in my ass," Brent called out.

I watched as Chris hastened his thrusts into his lover's ass and then his entire body went taut. He groaned as he unloaded in the pretty blonde ass. Brent moaned as he felt the warm cum fill his rectum and then the two of them embraced on the bed. They stayed in their embrace until Chris's cock softened and slipped from Brent's ass. They were speechless for almost a minute while I stood there with a rock hard boner. Chris spoke first.

"That was wonderful, now it is your turn, would you like to fuck me or should I suck your pretty cock?" he offered.

"I'd like to fuck you first," Brent replied.

He lay on his back but Brent told him to get on all fours. Next Brent picked up the lube and worked it in to Chris's ass. He then lubed his cock and knelt behind the pretty blonde gay to fuck him. I took this as my cue to get in on the action so I knelt on the bed in front of Chris so he could suck my cock. Brent eased his dick into the very curvy ass and once he was all the way in, Chris took my cock in his mouth.

"Oh good, I get to see you suck his cock while I fuck you," Brent said.

Brent was so hot that he came within minutes and flooded Chris's ass. He stayed hard however and kept right on fucking him. Chris was giving me a skillful blow jobs and I knew that I couldn't last much longer either. I felt my ball sac tighten and I knew it was only seconds before I would cum. He sensed my pending ejaculation and he reached down and caressed my balls and tickled my perineum which sent me over the edge. My body stiffened and my cock pulsated as cum jetted into the blonde's pretty mouth. He swallowed as quickly as he could and he kept right on sucking my cock. Soon the sensations got so extreme I had to push his head away from me. I was drained as I sat back to watch Brent as he continued to fuck his lover.

He really picked up the pace and he was relentless as he fucked the other blonde beauty. A few more frantic thrusts and then Brent plunged his cock all the way in and held it there as he ejaculated into the shapely ass a second time. I watched Chris clench and relax his buttocks as he milked the cock dry with his sphincter. Brent eventually softened and slipped out of the twitching ass. A large amount of cum oozed out of the dilated anus and I could only imagine how much cum had been dumped in Chris's ass. I was to learn later that Brent was a sperm producing machine.

"God it's always like a fire hose was turned on in my ass!" Chris exclaimed.

"Does he cum a lot?" I asked.

"Unbelievable and not just once but twice, Cliff please get me a towel."

I went into the bathroom and grabbed a towel for him as he asked. He took it and wiped his ass with it and then sat on it on the bed.

"God I can still feel it in my ass and I was afraid to get out of bed. I didn't want to be dripping cum all over the bed and the carpet. Brent can you possibly have anything left?"

"I'll be ready to go again shortly," Brent replied with a snicker.

Chris got up and went into the bathroom to clean up and then he returned to the bed. He lay down with Brent and they embraced again and stroked each other's body. Soon they were both hard again and they moved into a 69 position and sucked each other's cock. As they lay on their sides facing each other I felt my loins stir and my cock harden. I moved behind Chris and slipped my sizeable cock into his ass. I fucked him slowly as they continued to suck each other's cock. Brent reached between my legs and played with my balls as I fucked the other blonde. The three of us stayed in that position until everyone came again. I came in Chris's lovely ass as they came in each other's mouth. It was good that Brent had fucked Chris twice before I did as it helped loosen him up for my bigger dick.

The two boys got up, showered in my bathroom, dressed and returned to the parent's room. I was pleased with their receptiveness to a threesome and I liked fucking Chris's curvy bottom. As I dozed off on my bed I was thinking about fucking Brent's lovely bubble butt the next day.

ANOTHER BI SESSION WITH THE BLONDES

I was awakened early the next morning by a soft knocking sound on my door. I was still naked from the previous night's activities when I moved to the door.

"Yes, who is it? How can I help you?" I asked through the door.

"It's us, can we come in?"

It was Chris and Brent so I let them in and they smiled at my nakedness. "We told my parents that we were going for a jog on the beach and that we would see them at breakfast."

Their renewed confidence was obvious as they stripped and got in my bed. They moved into a spoon position with Brent fucking Chris from behind. My own cock stirred so I stroked it a few times and got it hard. Next I moved behind Brent and slipped my cock into his well-lubed ass. He obviously prepared himself to get fucked that morning. I didn't have to do very much since Brent was doing all the moving. When he shoved his cock into Chris's ass his ass moved off my cock a couple of inches, when he moved back toward me he impaled his ass on my cock. Brent came first so he stopped fucking Chris and then I picked up the pace and fucked him until I came in his ass.

They asked if they could use the shower and I agreed. I had to take a piss anyway and I too went into the bathroom. After I took my morning piss I pulled back the shower curtain and saw that Chris was fucking Brent in the ass. Brent had his hands on the shower wall with his back slightly arched emphasizing his shapely ass. Chris held to the hips as he drilled his lover's ass. I decided to join them.

I stepped in the shower and I felt my cock rising to the task. I grabbed the body wash and began to soap up Chris's ass and finger his asshole. Then I soaped up my erect cock and moved in close to him. He knew what was coming so he stopped fucking Brent long enough to let me slide into his ass. I pushed my soapy cock into the soapy asshole and then we both started to fuck. Once again I didn't have to do much work since Chris was in the middle fucking Brent. I came first and shot a big load into the enticing blonde ass. That seemed to set him off and I watched as his body stiffened and he came in Brent's ass. Chris's sphincter tightened around my cock as he ejaculated into his lover's rectum.

My cock slipped from Chris's ass and in turn his cock slipped from Brent's ass. Brent turned around sporting a hard cock and he reached for Chris. He put his hands on the other blonde's shoulders and pushed him to his knees. Chris went to his knees willingly and then took the throbbing cock in his mouth. Brent didn't last long and soon he was shooting into the warm wet mouth. The load was huge again and Chris pulled the spurting cock from his mouth after the first cum shot. He held the pulsating cock as it continued to shoot all over the blonde's face, neck and chest. Chris let the shower water wash the spunk from his body.

The three of us finished washing and then we all got dressed. They returned to the parent's room to get dressed for breakfast and later I joined them in the main dining room. The two pretty gays nearly panicked when I walked toward the table where they were seated with Chris's parents. I smiled and introduced myself.

"Good morning, you must be Chris's parents. I met these guys jogging on the beach this morning. May I join you?"

"Yes, please do. I am Peter and this is my wife Rhonda. You already met the boys, you say."

"Thank you, yes it was good to see young people out exercising early. I was glad to have the company."

Chris and Brent had relieved looks on their faces. It was clear that they were pleased with the way I handled the introductions. I looked at Rhonda and she was indeed a beauty with reddish auburn hair and with what I guessed to be a 35-28-36 figure. She seemed uncomfortable with me sitting next to her and I got the sense that she was not getting the loving her body craved. Peter was a portly out of shape man who had clearly let his body go. His wife however looked very fit and I sensed that she exercised regularly. I also suspected that she might have a lover or two at home if her husband wasn't keeping her happy.

"So what do you folks have planned for the day?" I asked.

"Rhonda and I are going to the National Park where they have the iguanas. After lunch we will do some shopping in town. The boys are not interested in that so they are hanging back for some beach time. What are your plans today?"