The Castaway Hotel: Book 4

Watching Kevin and Brent, however, was quite a different matter. They were growing closer every day and it seemed as if they couldn’t keep their hands off of each other. It wasn’t anything overt or obscene, just that they constantly seemed to be reaching out to touch the other’s hand, arm, face, knee or other exposed part, but not in a sexual way. When they sat together, it was done so their legs were touching or their arms were brushing each other, and it seemed as if they just needed to make contact to be sure the other one hadn’t left without them knowing it.

I was glad to see Kevin happy again and it was nice to see that Brent had found some happiness too. In talking with some of the other boys, I discovered that Brent and Kevin had been spending a great deal of time sleeping in each other’s rooms, so I figured it wouldn’t be long before they would probably be moving in together. A little later I pulled Kevin aside, to ask him how things were going.

“I notice you and Brent seem to be getting close,” I offered.

Kevin’s face lit up, before he responded. “Yeah, I guess we are,” he agreed. “We really get along great and he was kind of lonely too, just like me.”

“Well, I’m glad you found each other and hit it off,” I told him, sincerely. “Is there anything more going on?”

Kevin looked a little sheepish, but did answer me. “I think I know what you’re asking, and we have done some things together, but not a lot. Mostly just getting to know each other better.”

“Hmmm. What exactly does that mean?” I pressed. Kevin didn’t respond right away, so I asked another question. “Kevin, you know I don’t mind if you do things like that, as long as you both agree to it.”

“I know, and I know the other boys talk to you about things like this,” he replied, “but I just feel kind of funny telling you about Brent and me. I hope you’re not mad.”

“No, Kevin, I’m not mad. I was just curious,” I told him.

Kevin looked at me for a few seconds, saying nothing at all during that period of time, and then he let out a big sigh and spoke. “I don’t know why I worry about it. I know I can tell you anything, so I will. Brent and I have done some things together, but only with our hands and mouths. He said he wasn’t ready yet to try anything more.”

“Kevin, I thank you for trusting me with that information,” I responded, “and you know I won’t say anything, as long as you were both willing participants.”

“Oh, we were,” he enthused.

“I’m sure of that,” I confirmed. “It’s just nice to know who’s doing what and how much you boys are into. It helps me make decisions later, when other things come up.”

“I know and I’m sorry I didn’t answer you right away,” he confirmed, while looking a bit sheepish about his hesitance. “You’ve always been there for me, it’s just I guess I still worry about people reacting like my father did when he found out about us.”

“I can certainly understand why that would concern you,” I assured him, “but I promise you not everyone is as narrow-minded as your father.”

“Especially not you,” Kevin gushed. “I know that, but sometimes I can’t get past the other stuff.”

“You don’t have to explain or apologize,” I told him. “I’m asking you for personal information and I realize sometimes there are things you might not wish to discuss. I would never force you to divulge those things you aren’t comfortable with telling me.”

“That’s okay, Dad. You didn’t force me,” he confirmed. “I just finally realized you wouldn’t get mad if I told you and I understand you don’t know that much about Brent and are just trying to find out. I don’t mind if you know and I don’t think he would either.”

“I’m glad to hear that,” I said with a smile. “Now, why don’t you run along and join the others.”

“Thanks, Dad, I will.” Kevin made his way toward the door, but then stopped and turned to face me again. “You know, Brent’s going to stay with me tonight,” he added.

“I didn’t, but it doesn’t surprise me,” I conceded.

Kevin smiled at that statement. “He also said he might be ready to try something new tonight, if you know what I mean.”

“Well, from what you just told me, I think I have a good idea about what you’re referring to,” I stated. “You know where everything you’ll need is kept, don’t you?”

“Yes, Dad, I do, and we’ll be sure to use it, if we do anything,” Kevin agreed. “I’m so glad I live here and you’re my dad now,” he added, before jogging the few steps back to me, so he could give me a hug. I kissed him on the forehead and squeezed him back.

“Well, I’m very glad about that too,” I told him. “You’re a fine young man and I’m proud you’re my son. I trust you, and I’m reasonably sure you wouldn’t do anything you shouldn’t. I just want to warn you to be gentle with Brent, since he’s pretty new to all of this. I have a pretty good idea how he feels about you, since I’ve noticed the adoring looks he flashes in your direction whenever he sees you, so please don’t hurt him. I know you would never do it on purpose, so just go slow and follow his lead.”

“I understand and I’d never hurt him, Dad,” he confirmed. “I know what that’s like, remember?”

“Yes, Kevin, I do, and you deserve to be happy this time, so go enjoy yourself,” I encouraged, before kissing him on the forehead again. As he turned around to run off to find Brent, I gave him a playful smack on his bottom, to send him on his way. It was nearly time for them to take their showers anyway, and I soon saw them heading up the stairs together. Kevin gave me the account of what happened next, a couple of days later.

Kevin and Brent went up to the second floor bathroom, stripped down and jumped into the shower together. This wasn’t the first time they had done this, but this time was a little different and special for them. As soon as they were both under the showerhead, Kevin kissed Brent passionately, before he started to wash Brent’s body. He ran the soap over and around his chest, neck and arms, lathering him up well and scrubbing him thoroughly, before rinsing him off under the warm spray. He made Brent turn around, so he could wash his back using the same procedure, carefully making sure he was thoroughly clean. When Kevin got down to Brent’s butt, he rubbed soap all over both cheeks, ran his soapy fingers down the crack, swirled them around the tender opening to his love tunnel and then carefully slipped a finger inside, to clean it out as well.

Brent jumped at first, as the finger moved inside and began to probe him, and his sphincter muscle instinctively clamped down on Kevin’s intruding digit. Once Brent became accustomed to what was happening, he began to relax and let Kevin continue his actions without interference. As Brent began to enjoy the sensations and revel in the feeling of places being touched that had never been touched before, Kevin withdrew his finger and quickly replaced it with two fingers, before starting his ministrations over.

Brent suddenly began to thrust his butt backward, in an effort to urge Kevin on and give him better access to the unexplored region. He was thoroughly enjoying Kevin’s stimulation of his inner sanctuary and would never have believed it could feel so good. Getting lost in the new sensations coursing through his young frame, he threw his head back and let these feelings consume his mind and body, while he began to pant and his heart beat quickened.

He literally jumped when Kevin’s fingers hit his prostate and caused tingling sensations to pulse from the leathery button and shoot throughout his entire body. It almost felt as if an electrical current had just zapped his frame, but it was Kevin’s actions that had sent the sparks flying. Brent moaned slightly and his body trembled, as Kevin began to massage the sensitive area even more, and Brent grew even hotter as the action continued. He was also rock hard, and Kevin hadn’t even touched his penis yet, when suddenly his cock erupted, spewing out thin streams of nearly clear cum, just from the stimulation on his love button. He almost collapsed at this point, as his knees buckled from the powerful and unexpected release, since he had never had an orgasm before without his or someone else’s hand or mouth touching his dick.

“How did you do that?” he gasped out, as he began to regain his composure.

“Dad calls what I touched in there the prostate,” Kevin told him. “He says it’s one of the most sensitive sex organs a guy has, but I guess you just found that out.” Kevin then chuckled briefly, before continuing. “You shot your load and I never got to even touch your cock.”

“You still can, if you want,” Brent teased, “but that was pretty awesome. I didn’t know anything like that could even happen.”

“Well, you do now, and sometimes something like that can happen when someone has their dick up your ass too,” Kevin informed him. “If he is able to get the right angle as he pumps in and out, his penis will rub against your prostate and can cause you to shoot your load without touching your dick too.”

“Really? That sounds great,” Brent told him, while looking dreamily in Kevin’s direction. “Maybe we should try that tonight.”

“If you really want to, I’d love to do that with you,” Kevin agreed, “and you could do it to me too, but that’s all up to you. We’ll do whatever you decide, but first we have to finish cleaning up,” Kevin reminded him.

Having said that, Kevin bent down and finished washing Brent’s legs and then he turned him around, so he could wash the front of him too. Carefully, Kevin worked his way up to Brent’s genitals, which he washed thoroughly and took great pleasure playing with his penis in the process. Once Kevin had finished washing Brent, Brent was eager to return the favor.

Brent was overly excited and tended to hurry through washing the chest and back, so he could work his way down to Kevin’s firm, small butt. Brent immediately worked his fingers into and along Kevin’s crack, since he was eager to get to his anus, and quickly worked a finger up and inside his partner. Brent asked how to find the prostate and Kevin tried to explain how it was done. Brent was having a difficult time at first and was becoming frustrated, but finally he found it and began to stroke the leathery nub, which caused Kevin to moan and writhe in delight.

Even though he didn’t cause Kevin to ejaculate from his efforts, Brent still brought Kevin plenty of joy. After tiring of that activity, Brent asked Kevin to turn around, so he could wash Kevin’s front, moving from his chest, then the legs and finally to his groin. Once he had Kevin fully aroused, Brent rinsed him off completely, before grabbing Kevin’s stiff rod and sucking it into his mouth. He began to bob on it and gradually brought Kevin quickly toward the brink, but Kevin made him back off before he finished and explained he thought they should save the rest to do in their room. Reluctantly, Brent agreed, and the boys finished their showers, dried and padded down the hallway toward the bedroom they had been temporarily sharing.

Once inside, the boys got on the bed and Kevin asked Brent if he was sure he still wanted to try this. Brent told him he was, so Kevin got a condom and the KY out, greased up his fingers and began to work them into Brent again. Brent seemed to be enjoying this even more than he had in the shower, as Kevin gently probed him with first one and then two fingers. When he thought Brent was ready, he put on the condom, covered it with lubricant, laid Brent on his side and lifted his upper leg. Then, he moved forward, lined his torpedo up with Brent’s launch tube and used enough pressure to push it past the resilient guardian.

Brent’s body tightened slightly, as it instinctively tried to resist the intruder, but then he relaxed and the head of Kevin’s weapon slipped inside. Kevin stopped once he reached that point, so he could check with Brent and make certain he was all right and wanted him to continue. Brent quickly assured him he was fine, so Kevin began to slide the rest of his weapon into Brent’s sheath. Once he was fully seated inside him, Kevin waited again, to allow Brent time to become accustomed to the new sensation. However, it wasn’t long before Brent was urging him on again.

Slowly, Kevin began to withdraw from that warm, moist cavern only to ram his rod back in, and then repeated the process over and over again. Kevin kept adjusting his angle, trying to get it right, until he could tell from Brent’s response that he was hitting Brent’s prostate. Once he was positive his target had been located, he continued to bump and rub against Brent’s love button, until Brent was groaning in pure ecstasy.

As Brent began to get the hang of what was happening, he started thrusting his backside into Kevin, as Kevin thrust forward, making the experience even more pleasurable for both of them. After a couple of minutes of this action, Kevin began to feel his seed coming to boil in his groin, as it prepared to make its escape up his tube. Sensing the culmination of their coupling speeding toward him, Kevin began to assault Brent’s rectum harder and faster, as he sought his release, while still bringing Brent pleasure. Within moments, he was at the point of no return and rammed his penis deep into Brent’s passage and left it there, as several volleys of hot cum exploded from his tiny slit and filled the reservoir at the end of the rubber.

Kevin stayed buried inside of Brent for several minutes more, since he didn’t want to vacate that warm haven of pleasure any sooner than he had to. Although he didn’t know it at the time, Brent didn’t want him to pull out either, as he had totally enjoyed what they had just done and loved the feel of Kevin inside him. Before long, Kevin began to slowly lose his erection and his penis slid out of Brent’s chute, until it finally pulled free of its own accord. Brent suddenly felt empty and experienced a sense of loss, now that this newfound pleasure had ended.

The boys lay on the bed together for many minutes afterward, stroking each other’s bodies, kissing and thanking each other for the wonderful feelings they had just enjoyed. Kevin spun Brent around, so they were facing each other, and then hugged him tightly, while also smothering him in kisses. He was doing this to let Brent know how much he had enjoyed what they had just done, while showing him how much love he could feel from this very special act, but Brent already realized how wonderful and exciting it had been.

After they had fully recovered, Kevin asked Brent if he wanted to try being the pitcher, instead of the catcher. Brent chuckled at the play on words, since he’d never thought of this as a sporting event, but rapidly agreed that he’d like to try it too.

Kevin immediately began to explain to Brent what he should do, as he wanted to make this experience good for each of them too. First, he had Brent grease him up and work the KY inside of him, and then he unrolled a condom over Brent’s stiffy and added lube to the exterior of it once it was on. Seeing Brent was already lying on his back on the bed, Kevin just straddled his hips, lined Brent’s throbbing rod up with his hole, and then sat back on it, allowing it to slide completely inside of him. Once he felt his butt cheeks hit Brent’s pubes, he bent forward and kissed him, before asking him if he was ready to begin.

Brent never hesitated and exclaimed he was, since he was looking as eager to do this, as a puppy might be to begin chewing on a new bone. Having received his confirmation, Kevin began to repeatedly raise and lower himself on Brent’s crotch, willingly impaling himself over and over again on Brent’s rigid tool. As Kevin worked at maintaining a steady rhythm, he also watched Brent’s face. He instantly noticed Brent’s eyes were glazed over, his mouth was hanging open and his chest rose and fell dramatically due to his labored breathing.

As Kevin began to notice the signs of Brent’s impending climax approaching, he sped up his pace, clamping his ass muscles around Brent’s cock each time he lowered his body, to intensify the stimulation to Brent’s throbbing prick. As Brent began to moan and tell Kevin he was about to cum, Kevin lowered his body onto Brent’s tool, completely swallowing it with his rear end, and felt the pulsing sensations as Brent’s semen erupted and filled the tip of rubber. Without withdrawing, Kevin bent forward and kissed and hugged Brent, before thanking him for letting him be the first to experience this simple joy with him.

After they recovered from this effort, they went and cleaned up a bit, before returning to their bed and cuddling together for the rest of the night. They stayed wrapped in each other’s arms until morning, using that bond to remind themselves of the wonderful feelings they had just shared. I could tell when they came down to breakfast the next morning that they had indeed done what Kevin had suggested they might do, just from looking at the fulfilled and satisfied expressions on their faces. I was glad that I had some knowledge this might happen in advance, because now I could better understand how they were reacting to each other and how it had been for them, now that it was over.

Other than that experience, nothing much of interest happened to any of us until Dion had his first actual date with his new girlfriend the following Tuesday. The two of them spent most of the afternoon wandering around the mall, talking and getting to know each other better, before taking in a movie. I heard later that they did engage in some kissing at the movie and Dion seemed to have a good time, but it was primarily just your fairly typical first date. The other boys were trying their best to keep much of this information from filtering down to Trey, as they were worried he might get depressed from the news, but I knew it would be difficult to keep him from finding out about what was going on for very long. Sooner or later he would hear something from the girl’s friends or others they knew, but I also felt Trey had already prepared himself to deal with whatever happened.

I later learned that Dion had made another date with this girl for the following Monday and they were planning on doing a repeat of their previous date, plus maybe stopping to get something to eat together. I hoped Trey would be able to keep the same positive attitude about Dion’s attempt to find himself as he displayed when we talked the other day, but I knew the longer this went on, the harder it would be for Trey to keep his emotions under control.

I spent a good deal of my time that week with Frankie and Kevin, giving them extra driving lessons and trying to get them ready for their fall road test. Frankie was doing an excellent job behind the wheel, proving to be a very capable driver, and Kevin was also doing very well, but he was not as comfortable with this task as Frankie was. Neither boy should have any trouble passing his test when he took it in September, thus giving me two more drivers to split the taxi duties with. I did tell them they could do most of the driving when we went places as a family, providing I was with them at the time, and this would give them plenty of practical experience before their test. They seemed pleased with that announcement and my other drivers understood why I was going to let the beginners have this time to drive instead of them, since they still remembered how they wanted the extra experience before they took their road tests too.

I also had to change the time I was planning on going to the driving range with Jake, from Saturday morning to Thursday afternoon, after he got out of work. I had forgotten this was the weekend we were scheduled to go visit the Beckers’ farm and didn’t want to disappoint Little Ricky. He was very excited about our going there and had even called me Wednesday morning to see what time we’d be arriving. At first, I told him early Saturday morning, but he suggested we come Friday night instead, as he wanted the boys to be there so he could show them more about the farm. I finally agreed and told him we’d arrive on Friday and leave Sunday afternoon, and that seemed to satisfy him. I had originally planned to leave after church, but I figured I’d take everyone out to dinner first, to show them our appreciation for their hospitality, and Little Ricky was even happier to hear we wouldn’t be leaving until mid-afternoon. It was obvious he had all kinds of plans for us.

Thursday afternoon I met Jake at the driving range and we each hit a couple of buckets of balls. Jake gave me some pointers, to polish up my swing and get rid of the bad habits I had acquired after such a lengthy time away from the sport, and I got progressively better the longer I practiced. By the end of the session, I was hitting my drives straight, although not as long as I would have liked, and I was also doing fairly well with my irons. He complimented me several times on how quickly I was regaining my form, and then we decided to stop and have a couple of beers on the way home.

Jake was easy to talk to and I enjoyed his company. He even asked me if I’d like to fill out his foursome a week from Saturday, since they were currently one short. He explained that if I agreed, he and I would team up against two of his co-worker friends, since their usual fourth partner had other plans that day. I told him hitting a few balls was one thing, but I didn’t know if I was quite ready to actually play a round of golf again. Jake suggested that next Wednesday we’d hit the putting green and Thursday we could hit a couple more buckets of balls, and then I’d be ready for Saturday morning. I told him as long as he and his friends didn’t mind my rustiness, I’d be happy to join them, so the outing was confirmed.

The boys had dinner ready by the time I got home, and they peppered me continuously during the meal with questions about how I had done. For some strange reason they seemed pleased that Jake and I had stopped for a drink after we finished at the driving range, and they seemed even more thrilled to hear about our plans for the following week.

At this point I still didn’t know that some of them had suggested this idea to Jake in the first place, since I thought only Shannon had been involved in trying to set this up between his dad and I. However, I was to discover later that Jake had no idea his son had made similar suggestions to me, but that’s when we started to figure this whole little conspiracy out, but Jake and I will get into that in more detail later.

That evening, the boys even offered to clean my clubs and polish my old golf shoes for me by next Friday, so I’d at least look good when I went out Saturday morning, even if I didn’t play very well. I thanked them for their generous offer and graciously accepted, thinking their hearts were in the right place. Little did I know how instrumental they had been in arranging all of this in the first place!