This story contains gay sex between consenting adults. If this story offends you or it is illegal for you, please leave this site. If not..enjoy and let me know what you think!
The characters and events in this story are fictional. The story may portray some real people, events, or places.
This story follows two of the characters in Mr. Shepherd series. You can find the other stories here on Nifty.
1 - https://www.nifty.org/nifty/gay/adult-friends/mr-shepherds-summer-vacation/
2 - https://www.nifty.org/nifty/gay/college/go-gv/
3 - https://www.nifty.org/nifty/gay/adult-friends/mr-shepherd-moves-to-dallas/
4 - https://www.nifty.org/nifty/gay/adult-friends/mr-shepherds-friends/
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Winter Break
Ryan and Jimmy were having a great time learning about each other's likes and dislikes. Jimmy was the more mature of the two and made sure Ryan maintained focus on school and that he focused on his culinary school. Ryan wanted to spend more time together, but understood and just enjoyed when they could be together. They would video chat every night which often led to mutual jacking off. Ryan had given Jimmy one of his dildos and they would use those to fuck themselves as they watched the other.
Between school, work, swim meets and squeezing the last bit of warm weather out of the wave runners the boys kept busy. Ryan was taking a more active role at school and with the support of Jimmy, Thomas, Lucas and Mr. Shepherd was more confident. The end of the semester came and the class was voting for the President for the next school year. Ryan was surprised when he was nominated and even more surprised when he won! Many of his classmates said he changed their thinking about homosexuality and he was just an overall nice guy.
Jimmy's program ended at break and he was looking for a job. Thomas and Lucas offered him a job, but as this was the slow time of year could only offer him part time. He had other offers and said he really needed to consider them because his parents were moving and if he wanted to stay in the area would need to find a place to live and didn't think he could afford anywhere without a full time job.
Thomas and Lucas closed the restaurant over break and decided to take a vacation. They worked it out with Jimmy's parents and invited him along. Jimmy's parents said they were fully aware of Ryan and Jimmy's relationship and agreed that teens were going to have sex and that if Jimmy ever did the math would realize his mom and I were still in high school when he was conceived.
Thomas and Lucas surprised the boys with the news. They would be going to a surprise destination.for two weeks and would celebrate Christmas and New Years there. Ryan and Jimmy couldn't stop smiling. They were to leave the following morning so they needed to get packed up and Thomas suggested they bring some sunscreen and swim suits.
The flight was early the next day and when they received their boarding passes they saw the destination of Aruba! Lucas said this would be a relaxation vacation with a few adventures along the way. The boys pulled out their phones and started looking at different places on the island and started suggesting things they could do. Thomas and Lucas loved seeing their excitement and just listened to all their ideas.
When they arrived at the resort the boys were surprised to see so many same sex couples and were even more surprised when they were handed their own set of keys to their own room. Thomas explained they were across the hall, but they felt each couple having some privacy would be a good idea. Ryan and Jimmy had huge smiles and hugged Thomas and Lucas. They all headed to their rooms and Lucas suggested resting up from the trip and they would meet for dinner in a couple hours. From the sounds that echoed through the halls there wasn't much rest.
The foursome enjoyed a nice dinner then went for a walk along the beach. It was very romantic and Ryan loved being able to openly hug and kiss Jimmy. He watched Thomas and Lucas and was always very aware that Thomas' cock was hanging between his legs. He had fantasized about it since he caught Lucas sucking it and had even told Jimmy about it. Jimmy laughed and said he had heard rumors at the restaurant about his size and that he and Lucas might have sex with other men. Both boys agreed they would love to have sex with Thomas and Lucas and see what a foursome would be like. Ryan whispered in Jimmy's ear and Jimmy looked down at Thomas' crotch which was experiencing some movement from his kisses with Lucas.
The men walked back to the resort and as they rode up the elevator Ryan said that he learned that the age of consent for sex in Aruba was 16. Thomas and Lucas were curious about this statement. Ryan continued and said that so really he wasn't a minor the next two weeks. Thomas and Lucas looked at each other. Jimmy shifted uncomfortably. Then Ryan blurted it out. Jimmy and I talked and we know you have sex with other guys and we want to have sex with you both. The elevator chimed and the doors opened and two other couples entered. They rode in silence the rest of the way and when they got to their rooms Thomas and Lucas said they needed a minute alone.
Thomas and Lucas admitted they had been turned on by Ryan's dick and listening to the two of them have sex. But, aren't we technically his parents? Thomas said they were guardians, but Ryan had said he considered them more to be mentors than parent types. Thomas thought back to when he and Erik first met and how he looked to him to explore his sexuality, but they had waited until he was 18. But, technically, 16 was the same thing on the island. They went to the bar and poured two very stiff drinks to match their stiff cocks. They down the drinks and Thomas looked at Lucas. Are we doing this? Lucas grabbed Thomas' cock through his shorts and tweaked a nipple. Thomas grabbed Lucas' hand and the two crossed the hall and knocked on the door. Ryan was naked when he answered the door and Jimmy was naked in bed. Both fully erect. The door closed and that night Ryan learned why sometimes Thomas sounded like a beast. Neither were able to take Thomas in their ass, but loved watching as Lucas was pounded by Thomas. They both did work on Thomas' cock and enjoyed feeling it pulse a load between their mouths. Ryan made the move and pressed Lucas on his back. He crawled between his legs and and looked down at the hunk of heat in front of him. Jimmy came up next to him and lubed up his cock and Lucas' ass. Jimmy held Ryan's cock and aimed it into Lucas' hole as Ryan pressed forward. Lucas let out a low moan and Thomas bent down and kissed him as he took Ryan's cock up his ass. Ryan didn't last long and when he was finished Lucas looked at Jimmy. Jimmy smiled and quickly replaced Ryan's cock. Feeling the warm wetness brought him to a quick orgasm. Lucas smiled at Thomas. Thomas moved in and emptied another load into Lucas.
The men all collapsed together and Thomas and Lucas began to feel a bit of regret for what they had done. Ryan sat up and thanked Thomas and Lucas. You guys keep helping with my exploration! Thomas looked at Lucas. Thomas smiled and said they did have fun, but this couldn't happen back in the states. It was illegal. Ryan agreed quickly and said he would never want to do something that would put anyone at risk. Ryan held Thomas' cock and said he couldn't believe how big he was. Thomas smiled and said he should meet his friend Travis!
Lucas suggested he and Thomas head back to their room and shower and head to bed. Ryan hugged them together and said he was the luckiest guy in the world to have such incredible men in his life! Then leaned over and kissed Jimmy. Their kiss grew along with their cocks. Lucas and Thomas took this as their cue and grabbed their clothes and walked naked back to their room. They showered and fell asleep hearing Jimmy's loud growls. Lucas rubbed Thomas' nipples and Thomas' growls matched Jimmy's.
The men met for breakfast and then Lucas told them they were all headed out for a horseback ride. They had booked a private tour with a guide, Levi. They headed to the shuttle and a little while later were pulling into the facility. Levi greeted them. He was 5'10 with a very dark complexion. His teeth were so white against his skin. His smile had an effect on each of the men. He shook all their hands and definitely lingered with each. He walked them over to the horses and explained how the ride would go.
They were having a great ride along the beach and then through a wooded area. They came around a few trees that opened to a clearing and an incredible pool of water. The men all dismounted and tied off their horses. Levi showed them an area that was set up for a picnic lunch. They enjoyed the food and then Levi said it was time for a swim. He jumped up and stipped off his clothes. We are alone, so we go au natural! He stood naked with a beautiful uncut cock hanging between his legs. It wasn't huge, but his balls hung low! He grabbed a rope with a disc on the end. He stood on it and then as he swung over the water did a back flip into the water. Grabbing his crotch as he hit the water.
The men all looked at each other and jumped up and stripped off their clothes. This was an impressive view to Levi. He had never seen so many well hung men together. He smiled and his dick started growing. He planned on having a very good afternoon! One by one the men entered the pool. They swam for about an hour when Levi climbed out of the water. His erection stood straight out from his body. He smiled and said the horses aren't the only thing they could ride today. He moved over to a flat area, layed on the ground and folded himself over and started sucking his own cock. This was a huge turn on for all the men. Thomas and Lucas looked at Jimmy and Ryan and nodded toward Levi. The boys swam over and stepped out of the water. Their dicks were ready to play. Levi pulled a satchel out of nowhere and a bottle of lube appeared. Levi pointed to Jimmy. Levi wet Jimmy's cock and then rolled onto his knees. Levi pressed back onto Jimmy's dick and moaned, fuck me! Jimmy started thrusting and moments. The men took their turns and then Thomas stepped forward. Levi moaned just looking at it. He handed Thomas the bottle of lube and told him to be generous. As Levi felt Thomas enter him his cock pulsed and he came. Thomas was shocked at the convulsions he felt around his cock and even more surprised that his cock reacted so quickly and his balls emptied.
The men all jumped back in the pool and then sunned themselves dry. Levi looked at Ryan's boner and the shadow it cast on his stomach and said according to Ryan's sundial it is time to head back. The men chuckled a bit. They dressed and rode back to the facility. Thomas gave Levi a generous tip and they headed back to the resort. The driver about lost control when Ryan made the comment that he couldn't believe they all just fucked the same guy! Thomas, Levi and Jimmy all gave Ryan a look.
When they got back to their rooms they showered and wanted to get something to eat. Ryan and Jimmy were ready first and went over to Thomas and Lucas' room. Ryan asked if Thomas and Lucas had sex with a lot of guys? Lucas responded and said their sex life was their sex life. Ryan nodded, so that's really a lot! Lucas shook his head. Ryan said that he and Jimmy liked it and wanted to try some more before they head back to the states. Thomas said it can be fun, but be sure you two communicate and have some boundaries set. You both have to be having fun or it will destroy your relationship! Ryan nodded. Also, Jimmy wants you to fuck him. Jimmy winced hearing Ryan out his desire. Noticing his discomfort Thomas joked. Right now or do you want dinner first? The men all laughed and headed to the restaurant.
Jimmy wasn't talking much during dinner. Thomas leaned over and said he would love to fuck him and would make sure it was enjoyable for him. Jimmy grinned a bit. Then Thomas told Jimmy he was fired from the restaurant so he couldn't file sexual harassment charges afterwards. Jimmy started laughing. The men finished dessert and headed back to the room. This time they were in Thomas and Lucas' room. Ryan was blunt and said let's get the ball rolling! Thomas told Ryan to relax. Jimmy doesn't need to be stressed. The more relaxed he is the more enjoyable it will be.
Lucas took Ryan to the balcony and Thomas wrapped his arms around Jimmy. Are you sure you want to do this? Thomas asked. Jimmy nodded. Do you think you can handle it? Jimmy took a deep breath and then said that he had been using two dildos in his ass for a few weeks and really loved how it felt. He can't get fucked enough by Ryan and has even used a dildo with Ryan in him. Thomas thought about his ex-boyfriend Sean. Thomas kissed Jimmy passionately and they removed each other's clothing. Thomas worked Jimmy's body and spent a lot of time at his nipples. Jimmy moaned loudly and he spread his legs unconsciously. Thomas pulled a bottle off the nightstand and poured a generous amount in his hand. He pressed his fingers in and Jimmy moaned in delight. By time Thomas had 4 fingers in Jimmy was reaching full volume begging Thomas to fuck him.
Thomas added lube to his dick and pressed the head in Jimmy's hole. Jimmy's volume increased. Inch by inch Thomas slid in. More and more Jimmy moaned. Two more inches, 3 more inches. Jimmy couldn't stand it and wrapped his legs around Thomas and pulled him all the way in. Thomas was surprised but loved being buried in Jimmy's ass. Jimmy panted and told Thomas to do it. Fuck him. NOW! Thomas started thrusting and Jimmy was in heaven. He accepted he was 90% a bottom. This feeling was what he wanted to feel. His head was thrashing back and forth and at one point he noticed a naked Lucas and Ryan. They were stroking each other as they watched him get fucked.
Thomas was pounding hard now. He could feel his balls starting to tighten and he pulled Jimmy's legs higher to give him better access. The slap of skin on skin was intense and his last thrust echoed. His moan was matched by Ryan and Lucas who had moved over Jimmy and shot their load on his face and chest. Jimmy's ass felt the pulse of Thomas' cock and he reached down and stroked his dick once causing him to shoot his own load over his body. Thomas began to slide out and Jimmy shook his head. Not yet! Thomas smiled. Thomas felt Jimmy massaging his cock and slowly he felt his cock pushed from Jimmy's hole. Jimmy exhaled and grabbed Ryan's hand. Ryan leaned down and kissed Jimmy tasting a mix of multiple loads on his face. That night the four men slept together. The connection the four had developed extended beyond sex. Thomas felt as close to them as he did Javier and Erik.
The next few days were spent poolside. Ryan and Jimmy felt as though they were being watched. They saw two men smile and wink at them and then another guy and even a waiter. They knew they were good looking, but had never drawn this much attention. It was a turn on, but also a bit strange. They decided to enjoy the attention and would even put on a bit too much PDA when they noticed these men watching them.
Christmas morning they had breakfast and then Thomas and Lucas surprised the boys with gifts they had placed under a palm tree. The boys opened them and Jimmy loved the knife set. He said this was the best on the market! He hugged Thomas and Lucas. Ryan opened his gift and it was a framed picture of Thomas' convertible. When he pulled the frame out of the box there was a ribbon with the keys attached to it. His eyes bulged out of his head! Thomas said it was time for him to get a new car and couldn't think of anyone more deserving to give his car to. Ryan teared up and then said he can't wait to drive the convertible around with his dick out like Thomas had shown him. Lucas was shocked and then laughed.
Jimmy and Ryan told Thomas and Lucas to stay put. The boys took off and returned a few minutes later. They held out a bag for each. Thomas opened Jimmy's and found a piece of paper. It was the signed job offer that Thomas and Lucas had given him. They had done it as a joke so they would look like the other offers he had received. Jimmy said he had gotten a phone call from some guy named Leo who had gotten my name from the culinary school. He was looking for a personal cook and to ensure I would be available whenever he was in town, which isn't often, he had a small apartment above his garage I could stay at rent free! Lucas smiled at Thomas who shrugged his shoulders.
Lucas opened the other bag and found a puzzle. He laid the pieces on the little table between him and Thomas. As the two put it together they saw it was a picture of Ryan. They were missing one piece. Ryan handed them a card. When they opened it they found the final piece. It was a picture of the two of them and the note inside said that his life had been a huge mixed up puzzle, but since meeting the two of them his life has come all together. They placed the final piece in the puzzle and wiped the tears from their eyes. Ryan nugged Jimmy. I told you mine would make them cry!
Ryan asked what they were doing for New Year's Eve? Thomas and Lucas smiled devilishly. Let's just say we will bring the new year in with a bang! The boys were excited and then took off to the pool. The waiter brought Thomas and Lucas a round of drinks and gave each man a wink. A couple hours later the men all headed back to their room to shower and get ready for dinner.
During dinner Thomas told the boys that the next day they were going to spend the day on a catamaran and snorkeling. The boys were very excited as Thomas and Lucas described the tour. After dinner Jimmy asked if he and Ryan could take a walk alone along the beach. Thomas and Lucas agreed and they went their separate ways. Thomas and Lucas actually were hoping for some alone time as well so they could put the final touches on their New Year's Eve celebration.
Ryan loved that Jimmy wanted to spend alone time with him. They walked along the beach and held each other's hands. Jimmy stopped and turned to Ryan. He kissed him deeply. It was here with the surf at their feet that Jimmy told Ryan he loved him. He couldn't imagine not having Ryan in his life. Ryan teared up and said he loved Jimmy too. Both boys knew they were young, too young to be thinking about the rest of their lives, but in this moment with this person they were in love. That night their love making was quiet and passionate. When they finished their final orgasms they fell asleep with Ryan's cock still inside Jimmy.
The next morning after breakfast they headed to the marina. They were taken to the catamaran by a little rubber boat and greeted by Dane and Levi. The men all were surprised that Levi was part of this adventure. Levi explained that he works multiple excursions and it keeps his life interesting! Levi turned to Dane and explained that these men went on one of his horseback riding adventures with a wink. Dane smiled and said just wait till you are in the middle of the ocean without another soul around! The men all smiled and Dane openly rubbed his crotch.
The sails were lifted and sped across the ocean. The feeling was amazing. The ocean was like glass. A school of dolphins joined them and were racing along beside them. The men watched as the shoreline disappeared. Dane slowly lowered the sail and the catamaran slowed. There was barely a sound. The water splashing against the side of the boat and wind.
Dane and Levi handed out snorkeling gear and pointed off the boat. They showed them where they would be snorkeling and they would have as much time as they wanted. Lunch would be ready when they finished. They all jumped in the water and spent a couple hours just floating around and looking at the amazing life under the water. They swam back to the boat and were welcomed back with a tray of drinks. He went to hand one to Ryan and Jimmy. Ryan looked at Thomas and Lucas. They shrugged their shoulders. What happens at sea, stays at sea! They all raised their glasses and relaxed. Dane brought out a platter of island food. It was incredible.
Levi appeared with another round of drinks and was naked. Dane quickly joined him and said there was nothing better than being naked at sea. Well, except for fucking at sea and stroked his cock to it's full 8". The men all watched as Levi's cock grew. Levi leaned over to Dane and then Dane looked at Thomas and smiled. Are you boys going to join us or do you just want to watch me fuck the life out of Levi? The men were only wearing swim shorts which were quickly shed. Dane was correct. The feeling of being naked at sea was incredible! The breeze across their bodies and the anticipation of this encounter had them all erect in moments. Dane smiled and told Levi he wasn't lying. These are some of the biggest cocks he had ever seen, especially Groot over there. Levi explained that Groot means large in their language.
Lucas smiled. My husband, Groot. Thomas grabbed his cock and slapped it back and forth across his thighs. Lucas leaned in and let it hit him in the face. Then took hold of it and began sucking the head. Ryan and Jimmy smiled and Dane and Levi stepped over in front of them and presented their dark uncut cocks for sucking. Cocks were sucked and drained and asses were fucked and filled. Fucking was beyond incredible on the boat. The hammocks that hung on the front of the boat made incredible sex slings. Jimmy couldn't get fucked enough.
Levi climbed in the hammock with Jimmy and moved underneath him. Levi slid in his ass and the swinging caused the fucking to just happen without either moving. Dane stepped up to the sling and Levi raised Jimmy's legs. Ryan watched as Dane stepped between Jimmy's legs and pressed his cock alongside Levi's and double penetrated Levi's ass. Ryan looked at Jimmy's face and watched his eyes roll back in his head. Ryan stepped up and bent over and took Jimmy's cock in his mouth. The amount of precum oozing from Jimmy's dick filled Ryan's mouth as if he had shot a load! The amount of cock in his ass and the sensation of Ryan's blowjob was too much. Jimmy grabbed ahold of Ryan's hair and actually screamed as he shot his load into Ryan's mouth. Dane and Levi's cock were squeezed together with each pulse into Ryan's mouth and then began shooting. Jimmy almost passed out from the heat of the sex and the sun.
The foursome disentangled and noticed Thomas on top of Lucas grinding his hips back and forth as Lucas sucked on Thomas cock as he filled his ass. Thomas was the last to unload and Lucas swallowed every drop! The men all found a spot and laid back on the boat. Dane let out a howl and said this was one of the best cruises he had ever done! He and Levi pulled themselves together and they began the ride back to the marina. They all stayed naked until Levi instructed them to get dressed. Thomas handed Dane an envelope and thanked him for the incredible day. Dane and Levi wished them all a Happy New Year.
New Years Eve was upon them and the resort had an incredible event to celebrate. The event was listed as Black Tie. However, at the beach that rule looks different. Lucas pulled out some skimpy black speedos and handed them to the boys and Thomas. Then pulled out four bow ties. Thomas' speedo hid nothing. He would surely get a lot of attention tonight. When they arrived at the party it was a LOT of skin and skimpy swimsuits. Lots of assless and a few frontless! Ryan and Jimmy stare with amazement!
They found a table and enjoyed the music and food. It was midnight soon enough and they all raised a glass of champagne to toast the new year. As they finished their glass Ryan noticed a few men approaching their table. He bumped Jimmy and they both noticed these were the men that had been checking them out all week. Thomas waved them over and shook all their hands. Thomas introduced them all as the New Year's Eve Bang. Ryan and Jimmy both rubbed their crotches and felt their dicks respond. There were 6 men altogether. Lucas raised his hand and the waiter came over. He told him they were ready for their room service. He smiled and said he would meet them all at their room.
The group of men entered Thomas and Lucas' room and all immediately stepped out of their suits. Ryan and Jimmy looked at all the different cocks. These men all ranged in sizes. Some were uncut, shaved, big balls, and one pierced and a few with different style cock rings. Thomas stepped between the two boys. They are here to let you experience many different things. Ryan and Jimmy stared and didn't say a word. Thomas looked at Lucas. Finally, Ryan is speechless. There was a knock on the door and the waiter wheeled in a cart. He pulled the sheet off it and the men quickly assembled a sling. Jimmy wiped drool from his mouth.
Several hours passed and one by one the men left. When the sun rose it was just the four men. Jimmy was the first to rise. He told himself that last night he got enough! He rubbed his ass. Thomas stirred and rubbed his cock. He stood and walked to the bathroom to pee. Jimmy came in and watched. Thomas took hold of Jimmy's hand and pulled it towards his dick. Jimmy could feel the pee flow through his cock. Jimmy slid his hand down Thomas' shaft and felt blood surge to Thomas' cock. Thomas stepped into the shower and turned it on. The water warmed quickly and he pulled Jimmy in with him. Thomas turned Jimmy away from the spray and adjusted the shower head and Jimmy felt the warmth flow between his cheeks. It was just what he needed. Until the warmth had another effect. He had to pee. He moved to step out of the shower but Thomas held him in place. Jimmy looked panicked until Thomas smiled and told him to relax and let it happen. Jimmy exhaled and his cock released a heavy stream of pee that sprayed over Thomas' cock. He couldn't believe what he was doing.
His stream finished and he looked in Thomas' eyes. Thomas leaned in and kissed him and moved the shower to spray down their bodies. The warmth was nice and now they both were erect. Thomas lathered up Jimmy's cock and stroked him to completion. Jimmy did the same except made sure to swallow Thomas' load. Thomas turned off the shower and the two stepped out and dried off. When they returned to the room they found Lucas and Ryan in a 69 just in time to see each fill the other's mouths.
On New Year's Day they recovered poolside. The men they had met all stopped by to thank them for ringing in the new year! None of the men moved all day. Their waiter/friend brought them whatever they needed. Late in the day they went back to their room and showered for dinner. This was going to be their last night and planned on a quiet evening. Jimmy was grateful as his ass was still throbbing. The next day they were packed and headed back to Dallas. They were all very tan and tired. They all climbed in their beds and slept through the night and late into the next day.